Buying Online Businesses Podcast

Most people think buying a business is just about finding a “good deal.” Kevin Peterson has done over 50 acquisitions - and he’ll tell you that’s exactly how people lose money. Because what brokers don’t tell you…  is that the real risk isn’t the numbers? It’s what’s missing behind them. Like the SaaS deal that looked perfect on paper… until the entire team walked out right after closing. Or the “growth opportunity” that was actually just an audience no one had ever monetized. Or the biggest trap of all - buying a business without a clear thesis… and hoping it works out later. In this episode, Jaryd sits down with Kevin - founder of Webfolio Management - who’s spent the last 12+ years acquiring, operating, and scaling digital businesses across SaaS, content, and eCommerce. And this one goes deep. Into the real due diligence signals most buyers miss. Into how AI is quietly changing what businesses are worth buying - and which ones are becoming obsolete. Into the hidden risks inside “easy wins” like audience monetization and roll-ups. But more importantly… Kevin breaks down the exact thinking behind building a portfolio that doesn’t just grow - but actually survives. No hype. No shortcuts. No theory. Just hard-earned lessons from someone who’s done the deals, made the mistakes… and kept going anyway. 🎧 Hit play - this is what buying businesses really looks like.   Episode Highlights 02:27 The Career Pivot That Changed Everything – From 20 Years in Consulting to Buying Online Businesses 03:36 From $50K Deals to 7-Figure Acquisitions – How Kevin Built a 50+ Deal Track Record 06:08 The Hidden Value Most Buyers Miss – Untapped Audiences That Can Instantly Increase Revenue 09:22 The Deal That Looked Perfect… Until the Entire Team Walked Out After Closing 11:36 SaaS Due Diligence Simplified – The 4 Metrics That Actually Matter 17:01 The KPI That Signals It’s Time to Sell (Before the Business Declines) 22:14 What NOT to Buy in the Age of AI – And Where the Real Moats Still Exist   Key Takeaways ➥ The best deals aren’t found - they’re filtered. Without a clear acquisition thesis, you’ll chase instead of build. ➥ If the business can’t run without the founder, you didn’t buy an asset - you bought a job. ➥ The real cost isn’t the purchase price. It’s the capital required to grow the business after you own it. ➥ Conversion rate and churn will tell you the truth before revenue ever does - watch them closely. ➥ AI is lowering the barrier to entry. If your business can be easily copied, it’s already at risk. ➥ The biggest hidden upside in acquisitions is often an under-monetized audience. ➥ Most founders sell too late. The right time to exit is before growth starts getting harder.   About Kevin Peterson Kevin Petersen is a serial entrepreneur and founder of WebFolio Management, a portfolio vehicle that acquires and operates small SaaS companies on behalf of investors and himself.  Since getting started in the web-business market he has acquired dozens of internet businesses (including Picreel) and refined a deliberate, metrics-driven approach to sourcing, cleaning financials, and scaling recurring-revenue products.  Kevin focuses on building investor-grade units with clean books and repeatable growth processes, then deciding whether to hold, scale, or exit.  He frequently coaches other buyers and investors on building SaaS portfolios, and his playbook centers on deliberate deal selection, clean financial segmentation, and operational systems that allow multiple assets to be managed without chaos.    Connect with Kevin Peterson ➥ https://www.linkedin.com/in/kevinpetersen1/ ➥saastermind.net Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Most founders think selling a business is about getting the highest offer. Nathan Gwilliam spent 30 years learning why that belief is exactly what destroys exits. Three businesses built. Three exits are closed. And a front-row seat to some of the most painful – and profitable – lessons the entrepreneurial world rarely talks about out loud. Like the time Disney came knocking... and his partner wouldn't even let them see the financials. Or the earn-out that looked like a windfall on paper - until someone else was making all the decisions. Or the phone call on a Sunday morning, right before church, that changed everything about why he sold Adoption.com. In this episode, Jaryd sits down with Nathan – the founder behind the most visited adoption platform in the world – for one of the most honest, human, and genuinely surprising conversations we've had on this show. Because yes, you'll get the tactics. The roll-up acquisition strategy that turned his biggest competitor into his biggest asset. The 50/50 partnership trap that quietly kills deals before they ever start. The exact moment a founder should seriously consider selling – even if the timing feels wrong. But this one goes somewhere most business podcasts are too scared to go. Into the Sunday morning phone calls. Into making decisions from love instead of fear. Into what it actually costs – emotionally, financially, spiritually – to build something real and then let it go. Nathan doesn't dress it up. He doesn't hide the mistakes. And he doesn't pretend the journey was clean. And that's exactly what makes this one unmissable. 🎧 Hit play. This is the exit conversation nobody else is having. BONUS: Get a free 30-day trial of Nathan's all-in-one podcasting platform at PodUp, or head to podallies.com to book a free 45-minute podcast strategy session – directly with Nathan himself.     Episode Highlights 07:08 The $100 Million Yahoo Offer That Got Turned Down – And the Company That Was Dead 12 Months Later 10:31 The Sunday Morning Phone Call That Changed Everything About Why He Sold Adoption.com 15:00 How Nathan Bought His Biggest Competitor Without a Single Dollar Down 18:21 Built From Scratch in 24 Months – Then Disney Tried to Buy It 23:06 The Earn-Out Trap: Why Nathan Would Walk Away From Millions Before He'd Ever Sign One Again 27:17 The 18x EBITDA Offer a Partner Killed Before Negotiations Even Started 27:52 Why a 50/50 Partnership Is Quietly the Most Dangerous Deal Structure in Business 34:00 Love-Based vs Fear-Based Decisions – The Framework That Changed How Nathan Runs Everything 37:02 How Nathan Turned His Biggest Competitor Into His Biggest Asset (Without Paying Upfront) Key Takeaways ➥ When your business is worth more to someone else than it is to you - that's your signal to sell. ➥ Never sign an earn-out where the buyer makes all the decisions. You're handing them your money and your future in the same handshake. ➥ A 50/50 partnership sounds fair until you need to make a decision that actually matters. ➥ Your biggest competitor might be your best acquisition – buy them, absorb their traffic, and stop splitting the market. ➥ The best acquisitions don't require a big upfront payment – structure it right and the asset pays for itself. ➥ Businesses don't always go up. The founders who wait for the perfect moment often end up selling at the worst one. ➥ Brokers create competition. Competition creates leverage. Never negotiate a major exit one-on-one if you can avoid it. ➥ Lead with genuine value and build revenue around it – the freemium model is still one of the most powerful plays in digital business. ➥ The best business decisions aren't made from fear. They're made from love – for your partners, your customers, and the impact you're trying to create.     About Nathan Gwilliam Nathan Gwilliam is a serial entrepreneur who has created and sold three digital ventures, including Adoption.com, the world’s most visited adoption platform. He grew major online communities and digital properties, and later sold Adoption.com to the Gladney Center for Adoption. Today he leads PodUp, an all-in-one podcasting platform that recently raised significant funding. Nathan’s unique journey – building, scaling, selling and reinventing digital businesses – gives him deep insight into acquisitions, growth strategy, and what it REALLY takes to exit for maximum value.   Connect with Nathan Gwilliam ➥ https://podup.com/  ➥ https://podallies.com/    ➥ https://www.linkedin.com/in/nathangwilliam/    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-busi

What does it actually look like to buy a business with zero margin for error? No safety net. No backup plan. A full-time military career, seven kids at home, and a lender who pulled out mid-deal. That's exactly where Michael Simpson found himself. In this episode, Jaryd Krause sits down with Michael Simpson - a National Guard serviceman who bought an 18-year-old e-commerce business using SBA financing, survived a near-collapse due diligence process, and came out the other side with a real, running business. But he's not here to tell you it was amazing. He's here to tell you the truth. Here's what's covered: 🏦 How he lost his SBA lender mid-transaction - and saved the deal in 48 hours 💀 The post-closing liquidity trap that blindsides almost every first-time buyer 😬 Why buying slightly bigger might have changed everything 📈 The unglamorous growth playbook keeping a 20-year-old business moving forward This isn't a success story wrapped in a bow. It's something far more valuable - an honest account of what buying a business really costs you. In money, stress, and lessons you can't learn anywhere else. If you're thinking about buying your first business, this might be the most important episode you listen to all year. 🎧 Hit play. Real talk only.   Episode Highlights 13:32 The SBA Pre-Approval Myth That Almost Derailed the Deal 16:15 Lender Drops Out Mid-Deal - How Michael Scrambled and Saved It in 48 Hours 19:48 The $10,000 Non-Refundable Move That Kept the Seller at the Table 21:25 The 100-Hour Business Plan That Stunned Bankers on Million-Dollar Deals 27:58 The $30,000 Tech Migration Mistake That Still Haunts Him 33:45 The Post-Closing Liquidity Trap That Catches First-Time Buyers Off Guard 35:49 Why He Had to Stop Paying Himself -  And Go Back to Work Anyway 36:27 The Brutal Truth About Buying Too Small (And What He'd Do Differently)   Key Takeaways ➥ "SBA pre-approved" listings are a marketing tactic - the real approval depends on YOU as the buyer, not just the business. ➥ Losing a lender mid-deal isn't fatal - having two banks compete for your business can actually get you a better outcome. ➥ A non-refundable deposit signals serious intent and can keep a seller loyal to you when the deal gets rocky. ➥ Post-closing liquidity is the number most first-time buyers forget - 10% down is just the starting line, not the finish. ➥ Buying too small is a trap - if the business can't cover debt service, pay for growth, AND pay you, you'll end up working for free. ➥ A obsessively detailed business plan doesn't just impress lenders - it becomes your single biggest competitive advantage in a crowded deal. ➥ Technical debt is invisible until you own it - always pressure-test the tech stack before you sign, not after. ➥ Boring, stable, decades-old businesses with loyal customer bases consistently outperform shiny, high-growth ones for first-time buyers. ➥ The real cost of buying a business isn't the purchase price - it's everything that comes after the wire transfer hits.   About Michael Simpson Michael Simpson is a business owner, acquisition entrepreneur, and National Guard serviceman who successfully bought a business using SBA financing while balancing a full-time military role and raising seven children.  His acquisition journey included a near-deal-ending due diligence process and the challenge of replacing his SBA lender mid-transaction. Michael brings a rare, real-world perspective on resilience, risk management, and executing an acquisition under extreme personal and financial pressure.   Connect with Michael Simpson ➥ https://x.com/Michael_in_biz    ➥ https://www.discountcatholicproducts.com/    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

What if the thing standing between you and total lifestyle freedom… was just one business acquisition? A former respiratory therapist and a software developer – no entrepreneurial experience, no roadmap, no idea what they were doing – decided to bet on themselves anyway. And now? They're running a lean team of 11 VAs from wherever in the world they feel like being that week. Guatemala last month. St. Kitts for their anniversary. Belize next. You get the picture. In this episode, Jaryd Krause sits down with Alan and Mel, a husband-and-wife duo who tried every side hustle in the book – financial lending, credit repair, online teaching – before discovering that buying an existing online business was the shortcut they'd been exhausting themselves looking for. They used SBA financing to acquire a $1.2M business with just $65K out of pocket. They inherited 2 VAs and a chaotic operation. They were working 60-hour weeks at the start. And then – systematically, strategically – they rebuilt it, scaled it, and sold it. Profitably. Now they're already under LOI for their next deal. Here's what makes their story different though. Neither of them had ever owned a business before. One was in healthcare. One was in tech but still didn't think you could buy something you couldn't physically touch. They were scared, skeptical, and figuring it out in real time. Sound familiar? If you've ever wondered whether someone like YOU could actually pull this off – this episode is your answer. Hit play. You'll want to hear this one.🎧   Episode Highlights 06:09 The $0 Down Deal Structure Most Buyers Don't Even Know Is Possible 15:13 How They Bought a $1.2M Business With Just $65K Out of Pocket 18:26 Why Taking 6 Months to Close Was the Smartest Thing They Ever Did 24:09 From 60-Hour Weeks to 5: The Exact Strategy They Used to Replace Themselves 29:00 The Layoff That Forced Them All In – And Accidentally Changed Their Lives Forever 33:33 They Sold the Business… and Got Bored in Two Months. Here's Why They're Back 35:33 The Raw Truth About Mindset That Most Business Coaches Are Too Polished to Say 42:12 The Wealth Loop Nobody Talks About: How One Business Funded an Entire Real Estate Portfolio   Key Takeaways ➥ You don't need industry experience to acquire a business – the learning happens after you buy, not before. ➥ SBA financing can get you into a $1.2M business with as little as $0 down if you negotiate the deal structure right. ➥ The fastest way to scale an acquisition is to document every bottleneck, then hire to eliminate them one by one. ➥ A longer closing timeline isn't a red flag – it's free due diligence that lets you watch the business perform before you own it. ➥ The moment you stop working IN the business and start building a team around it, everything changes. ➥ Buying a business where the owner is burned out is a hidden goldmine – lower price, massive upside, ready to scale. ➥ Online businesses have no glass ceiling – unlike physical businesses, growth isn't limited by location, rooms, or geography. ➥ Business cash flow funds real estate. Real estate equity funds the next acquisition. That loop, repeated, builds serious wealth. ➥ Mindset isn't a buzzword here – it's the actual difference between people who pull the trigger and people who stay stuck researching forever. ➥ Freedom isn't something you find after you build the business. It's something you design into the business from the start.   About Alan & Mel Alan and Mell are a husband-and-wife duo who’ve turned online business acquisitions into a lifestyle of freedom and adventure. Alan, with a background in education and technology, and Mel, a former respiratory therapist with an MBA from Ohio State’s Fisher College of Business, combined their skills to acquire three online businesses—recently exiting one successfully. Their profits helped them purchase two Airbnb properties and build a third in Belize. Thanks to the flexibility of their online ventures, they recently spent a month in Guatemala and El Salvador with their daughters for a World School program. Now, they’re under LOI for their next deal and on track to acquire three new deals within the next year.   Connect with Alan & Mel ➥ https://risingphoenixfund.org/home ➥ AI content creation platform: https://wordgenius.ai/   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3w

Most buyers are still doing due diligence like it's 2015. And the ones who know how to use AI? They're finding better deals, faster, and you'd never even know they were looking. In this episode, Jaryd sits down with Haytham Allos, M&A strategist, AI specialist, and one of the minds behind one of the world's first AI-powered law firms, to pull back the curtain on what's actually happening right now at the intersection of artificial intelligence and buying businesses. And it gets wild. We're talking AI agents that evaluate deals. Smart contracts that close them. Fractionalised ownership that lets someone invest in a business for as little as $50. A future where your AI agent negotiates with the seller's AI agent, and a human just says yes or no at the end. But before we get there? Haytham breaks down what's happening right now. Why most buyers are still flying blind, why AI without the right prompting is actually dangerous in a deal, and the one thing that kills more mergers than bad financials ever will. You'll discover why prompt engineering is the most underrated skill in acquisitions today, how to use AI to get an unfair edge in due diligence without replacing your gut instinct, and exactly where the smart money is already moving. This isn't theory. This is where M&A is heading, and the buyers who understand it now are going to own the next decade. Hit play. Your competition probably already has. 🎧   Episode Highlights 05:45 The Chainsaw Analogy: Why AI Without Experience Is Genuinely Dangerous in a Deal 09:08 The Hallucination Problem: Why AI Can Lie to You During a Deal and How to Stop It 13:57 Where AI Creates the Biggest Unfair Advantage in the Acquisition Process Right Now 16:43 Prompt Engineering: The Most Underrated Skill Every Serious Buyer Needs to Master 19:44 The Rise of Agent-First Companies: What Cursor AI's $2 Billion Valuation Tells Us About the Future 22:31 The Mindset Shift Every Business Owner Must Make or Get Left Behind 28:16 AI Agents Buying From AI Agents: The Future of M&A Is Closer Than You Think 31:12 Smart Contracts, Crypto Wallets and the Death of Bureaucratic Deal Making 35:43 Fractionalised Business Ownership: How Anyone Could Invest in a Business for $50   Key Takeaways ➥ AI without experience is like handing a chainsaw to someone who's never cut down a tree. Powerful tool. Dangerous hands. ➥ AI will hallucinate during your due diligence. If you don't know how to configure it correctly, it will confidently lie to you about the business you're about to buy. ➥ Prompt engineering is the most underrated skill in acquisitions right now. The quality of your questions determines the quality of your deal. ➥ The number one reason mergers fail isn't bad financials. It's people, politics, and ego. AI is quietly removing all three from the equation. ➥ We are shifting from AI that answers questions to AI that takes actions. The buyers who understand that difference right now will have an unfair advantage for the next decade. ➥ Smart contracts, crypto wallets, and blockchain are about to collapse the layers of bureaucracy that slow every deal down. The merger process, as we know it is on borrowed time. ➥ Fractionalised ownership is coming to business acquisitions. You won't need six figures to get into a deal. You'll need the right agent and the right wallet. ➥ The future of M&A is two AI agents negotiating a deal, presenting it to their humans, and closing it on the blockchain before a bank even answers the phone.   About Haytham Allos Haytham Allos is an M&A and AI strategist focused on how artificial intelligence is transforming the buy-side deal process. He works at the intersection of technology, data, and acquisitions, helping investors and acquirers use AI to enhance due diligence, identify hidden risks, and make better capital allocation decisions.  Haytham specializes in applying AI tools across deal sourcing, financial analysis, operational review, and post-acquisition decision-making.   Connect with Haytham Allos ➥ https://vikk.ai/ ➥ https://finance.yahoo.com/news/vikk-ai-selected-prestigious-aws-141700773.html?guccounter=1   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnyst

Buying a $10M–$100M online business isn’t just about having capital. It’s about relationships, structure, leverage, and knowing how the game is really played behind closed doors. In this episode, Jaryd Krause sits down with Emmet Kilduff, founder of The Fortia Group and former investment banker at Morgan Stanley, to unpack how serious online acquisitions actually get done in the $10M to $100M range. After 25 years in M&A, Emmet pulls back the curtain on what separates institutional buyers from everyday acquirers, and why trying to “figure it out yourself” is one of the most expensive mistakes you can make. You’ll learn: The 3-stage “Flirt, Date, Marry” framework elite dealmakers use to build acquisition relationships years before a deal closes Why the best buyers pitch sellers, and how to create a buyer deck that makes founders want you The real funding structures used by strategics, private equity, aggregators, and search funds What’s changed since the 2021 acquisition boom, and why 100% upfront deals are basically extinct The truth about earn-outs (and why most are designed for buyers, not sellers) Why recurring revenue businesses command premium multiples, and how valuation arbitrage actually works How to transition from operator to owner so you can think strategically and fund bigger moves This is not theory. This is how real capital allocators think. If you want to understand how serious acquirers finance deals, structure terms, protect downside, and build relationships that lead to eight- and nine-figure exits, this episode is your behind-the-scenes briefing. If you’re planning to buy, sell, or scale an online business and want to understand how institutional-level M&A actually works, hit the “Play” button.   Episode Highlights 03:12 Why Even $10M Buyers Shouldn’t Go It Alone 05:08 The “Flirt, Date, Marry” Framework for Closing Bigger Deals 08:41 How Smart Buyers Pitch Sellers (And Win Trust Fast) 12:06 The Truth About Earn-Outs (And Why Sellers Should Be Careful) 18:47 The Three Types of Institutional Buyers in the $10M–$100M Range 23:55 Why Recurring Revenue Changes Everything in Valuation 28:36 The Strategic Conversations That Should Happen Before Price Is Discussed 35:44 From Operator to Owner: Making the Shift to Strategic Thinking 40:27 Building an Advisory Board That Actually Moves the Needle Key Takeaways ➥ Buying a $10M–$100M online business is as much about relationships and strategy as it is about money. ➥ Use the “Flirt, Date, Marry” framework: build trust early, share information progressively, and finalize only when both sides are aligned. ➥ Strong buyers actively pitch sellers—your experience, vision, and team matter just as much as your capital. ➥ Typical deal structures include 60–80% upfront with the balance via earn-outs, equity rollover, or milestone-based deferred payments. ➥ Structuring earn-outs around revenue, not profit, reduces disputes and protects long-term relationships. ➥ Recurring revenue businesses (SaaS, subscriptions, memberships) command higher multiples and offer more predictable financing. ➥ Advisory panels and mentors accelerate decision-making, reduce risk, and boost credibility with sellers. ➥ Transitioning from operator to owner requires delegation, trust, and strategic focus over day-to-day management. ➥ Patience, preparation, and network-building are the hidden factors that make or break acquisition success.   About Emmet Kilduff Emmet Kilduff is the Founder of The Fortia Group, an M&A advisory firm specializing in the sale of eCommerce brands and digital agencies. With a background at leading Wall Street investment banks including Morgan Stanley, Emmet brings institutional-level M&A, valuation, and deal-structuring expertise to small and mid-market online businesses.  Through Fortia, he has advised founders, buyers, and investors on acquisitions across the UK, US, and international markets, helping them navigate financing, positioning, and exits with professional rigor.  On this episode of the Buying Online Businesses Podcast, Emmet shares how sophisticated buyers think about funding acquisitions, structuring deals, and avoiding the common mistakes that derail first-time online business buyers.   Connect with Emmet Kilduff ➥ https://www.linkedin.com/in/emmettkilduff/ ➥ https://thefortiagroup.com/     Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empi

Online business acquisitions aren’t won by the highest bidder - and they’re definitely not lost for the reasons most buyers think. In this episode of the BOB Podcast, Jaryd Krause sits down with Ryan Condik - serial entrepreneur, M&A advisor at Quiet Light, and founder of Let’s Buy a Business - to unpack what actually determines who wins (and who loses) in competitive acquisition processes. Most buyers assume it all comes down to price. Just offer more and you win, right? Not exactly. In real-world M&A, things like certainty, speed, positioning, and creativity often matter more than a bigger number. Ryan shares behind-the-scenes stories from competitive deals, including why some buyers lost over small term differences, how one buyer won simply by building a genuine relationship with the seller, and why “certainty of close” can be far more powerful than offering an extra 10%. You’ll learn: Why sellers often choose lower offers - and what they’re really evaluating How certainty, speed, and clean deal structures give buyers a serious edge Why trust and relationships can outweigh valuation The common buyer mistakes that quietly kill deals How creative structuring (including equity rollovers) can change the outcome Why knowing your value-add before submitting an LOI shifts the entire negotiation Whether you’re buying your first online business or competing for premium assets in a crowded market, this episode breaks down what separates serious acquirers from hopeful bidders. In M&A, price gets attention - but certainty wins deals. 🎧 Hit play to learn how to position yourself as the buyer sellers actually want to choose.   Episode Highlights 02:53 Why Chasing Billions Is a Trap (And What Actually Builds Freedom) 12:42 The “Seasons of Life” Framework for Smarter Entrepreneurship 18:02 The Two-Way Door Rule: How Elite Entrepreneurs Make Fast, Confident Decisions 20:17 Why Most Aspiring Entrepreneurs Fail Before They Even Start 24:34 The #1 Mistake Buyers Make When Acquiring a Business 26:24 Why Most Buyers Lose Deals (And Don’t Even Know Why) 28:46 The $400 Move That Won a Multi-Million Dollar Deal 30:45 How Relationships Beat Higher Offers in Competitive M&A 32:04 The 10% Lower Offer That Still Won the Deal 35:45 SBA Buyers vs. Serious Buyers: What Sellers Actually Want 37:38 When Paying MORE Is the Smartest Financial Decision 40:01 How to Know When You’ve Found “The One” (And Go All In) 43:00 AI, Adaptation & Why Average Operators Will Get Left Behind   Key Takeaways ➥ Traditional SEO is still the foundation—AI and GEO optimization enhance it rather than replace it. ➥ Strong brand presence and mentions across multiple platforms are now more important than backlinks for AI visibility. ➥ Being associated with reputable brands or industry leaders boosts authority and trust in AI-driven results. ➥ Content hubs and semantically related pages improve AI discoverability more than focusing on keywords alone. ➥ Social media, forums, and niche communities (Reddit, Medium, Facebook Groups) contribute to AI recognition. ➥ Balance is key: optimize for AI while maintaining usability and experience for human visitors. ➥ AI content generators can efficiently create research-backed, brand-aligned, and contextually rich content.   About Ryan Condie Ryan Condie is a serial entrepreneur, M&A advisor and founder behind Let’s Buy a Business. He has built, bought, and sold multiple digital ventures including RentLingo via a successful acquisition. He now helps founders master deals, due diligence and exits. Ryan also serves as an advisor at Quiet Light Brokerage, where he guides buyers and sellers through evaluations, negotiations and growth opportunities that maximize exit value. His experience blends real-world deal execution with deep strategic insight.    Connect with Ryan Condie ➥ https://ryancondie.com/ ➥ https://www.letsbuyabusiness.com/   Other podcasts with Ryan; https://buyingonlinebusinesses.com/ep-149-why-buy-a-profitable-online-business-instead-of-staring-one-with-ryan-condie-part-1/ https://buyingonlinebusinesses.com/ep-150-title-how-to-get-started-buying-profitable-online-business-with-ryan-condie-part-2/   https://www.youtube.com/watch?v=hRv7UHDUjYA     Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors

The internet isn’t being searched the same way anymore—and most businesses haven’t caught up. In this episode of the BOB Podcast, Jaryd Krause welcomes back Rad Paluszak to explore the transition from SEO to GEO (Generative Engine Optimization) and what it means for founders, operators, and investors navigating an AI-driven world. Instead of ranking pages, AI answer engines are ranking entities, brands, and trust. Rad explains why traditional SEO playbooks are breaking down, how AI engines source and rotate answers, and why brand mentions across the web now matter more than links ever did. You’ll learn: Why AI engines rarely repeat the same sources—and how that changes traffic forever How brand authority is built through mentions, associations, and personal brands Why being listed alongside established brands can instantly elevate visibility The growing role of Reddit, social platforms, and communities in AI discovery How to structure content for AI without sacrificing real users What businesses should stop obsessing over—and what actually moves the needle Whether you run content-heavy sites, ecommerce brands, SaaS, or are evaluating businesses to buy, this episode offers a practical framework for adapting to AI without panic—or guesswork. AI is coming either way.The question is whether your brand will be visible when it does. 🎧 Hit play and learn how to stay visible before the rules change completely.     Episode Highlights 03:10 Pivoting from SEO to GEO: How AI is Changing the Search Landscape 06:00 The Growing Importance of Brand Mentions and Broad Visibility 10:00 Leveraging Listicles, Social Media, and Mentions for Authority 14:00 Optimizing Websites for AI Agents vs. Human Users 18:00 Content Strategy for AI: Hubs, Semantic Relevance, and Queries 22:00 Auditing Your Site and Competitors for AI Visibility 24:00 Using AI Tools: Visibility Reports and Content Generators 29:00 Incorporating Brand Voice, Contextual Images, and Internal Linking 32:57 Scaling Your Business with AI-Driven Content Strategies   Key Takeaways ➥ Traditional SEO is still the foundation—AI and GEO optimization enhance it rather than replace it. ➥ Strong brand presence and mentions across multiple platforms are now more important than backlinks for AI visibility. ➥ Being associated with reputable brands or industry leaders boosts authority and trust in AI-driven results. ➥ Content hubs and semantically related pages improve AI discoverability more than focusing on keywords alone. ➥ Social media, forums, and niche communities (Reddit, Medium, Facebook Groups) contribute to AI recognition. ➥ Balance is key: optimize for AI while maintaining usability and experience for human visitors. ➥ AI content generators can efficiently create research-backed, brand-aligned, and contextually rich content.   About Rad Paluszak Rad Paluszak is a digital marketing and SEO strategist focused on AI search, Generative Engine Optimization (GEO), and brand visibility in an AI-first internet. He helps businesses adapt beyond traditional rankings by optimizing for brand authority, entity mentions, and AI discovery across Google, ChatGPT, and social platforms. Rad specializes in visibility audits, content strategy, and future-proofing brands for generative search   Resource Links ➥ Ordering PROMO content packages (1 Free + 10 articles with images, internal linking and brand voice included): https://order.non.agency/content?referral_code=Buying_Online_Businesses ➥ Free AI Visibility Report: https://non.agency/en/service/ai-search-optimization-aio/?referral_code=Buying_Online_Businesses#ai_visibility ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Getting finance to buy an online business is no longer just about ticking boxes or relying on outdated bank formulas. Today, lenders are looking forward. They want to understand your assumptions, your go-to-market strategy, and how the business performs once capital is deployed. In this special episode, Jaryd Krause speaks with Ciaran Burke, COO and co-founder of Swoop, a global SME funding marketplace helping buyers access debt, equity, and grant funding across the UK, Australia, the US, and Canada. Ciaran has helped thousands of businesses secure funding by unlocking options traditional banks often miss. You’ll learn how buyers are funding ecommerce, SaaS, and media acquisitions, what lenders really care about beyond the numbers, and why acquisition finance is now easier to access in markets like Australia and the UK. If you are planning to buy an online business and want to understand how deals are being funded right now, hit the “Play” button!  BONUS: Explore Swoop’s free funding platform and see if your next acquisition qualifies.   Episode Highlights 06:00 Funding Options for Acquiring Online Businesses 09:02 Understanding Deposit Requirements for Acquisitions 12:05 Setting Up a Business Entity for Acquisition Financing 15:03 Navigating Interest Rates and Loan Terms 18:02 Refinancing and Its Importance for Business Owners 21:02 Key Requirements for Loan Approval 24:38 Navigating the Financing Landscape 30:00 Preparing for Acquisition: Key Documentation 36:03 Understanding the Acquisition Process 40:01 Exploring Financing Options and Strategies 43:53 The Importance of Credit and Sector Awareness   Key Takeaways ➥ The Australian market was targeted for expansion during COVID due to its strong SME financing landscape. ➥ Deposits for acquisitions can vary significantly based on the business type and trading history. ➥ New investors may need to provide a higher deposit compared to those with established businesses. ➥ A solid business plan and financial model are crucial for securing financing. ➥ Interest rates and loan terms can vary widely based on market conditions and business performance. ➥ Refinancing options can improve cash flow and reduce interest rates over time. Understanding personal credit scores is essential for first-time investors.   About Ciaran Burke Ciarán Burke is the COO & Co-Founder of Swoop, a global SME funding marketplace that helps businesses discover debt, equity, and grant options using integrated business data.He co-founded Swoop after a career at KPMG and building the creative network Hiive, and now leads the product & operations work that matches businesses with suitable finance solutions across multiple territories. Swoop’s platform has helped hundreds of thousands of businesses access funding and simplify options that traditional banks often miss, making it a powerful route for buyers who need acquisition capital. Ciarán frequently speaks about debt, equity, and grants to fund acquisitions in the UK, Australia, and the US.   Join Swoop Funding for free; ➥ https://swoopfunding.com/au/buying_online_businesses   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

In this solo episode, Jaryd Krause dives into a topic that quietly shapes success more than most people realize: relationships. While many know him for his business insights, fewer are aware of how deeply spiritual his personal development journey has been and how much those “non-traditional” practices have contributed to his financial and professional success. With nearly three decades of inner work and growth behind him, Jaryd shares what he typically teaches behind closed doors to paid clients. Lately, one theme has been impossible to ignore: the profound impact relationships have on wealth, confidence, and expansion. He explores how most people have three to five close relationships: family, partners, friends, or colleagues that unintentionally stifle their growth. Check out the full episode to uncover the relationship dynamics that may be quietly holding you back—and learn how to break free from them.   Episode Highlights 02:44 The Impact of Relationships on Wealth 05:41 Family Dynamics and Financial Mindsets 07:54 Navigating Friendships and Financial Advice 10:44 The Role of Intimate Relationships in Personal Growth 21:34 The Impact of Relationships on Personal Growth 26:46 Navigating Friendships and Family Dynamics 32:20 Auditing Relationships for Abundance 37:29 Re-engineering Identity Through Social Circles 42:21 Actionable Steps for Relationship Management   Key Takeaways ➥ Spiritual practices contribute significantly to business success. ➥ Relationships can unconsciously stifle personal growth and abundance. ➥ Family conditioning often instills a scarcity mindset. ➥ It's crucial to audit your relationships regularly. ➥ Intimate partners can influence your ambition and success. ➥ Friendships should be evaluated based on their alignment with your goals. Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

What does it really take to acquire 26 SaaS businesses—and keep them growing? In this episode, Jaryd Krause sits down with SaaS M&A professional Guillaume Lussato for a behind-the-scenes look at how successful software acquisitions actually happen. Guillaume breaks down his unconventional path from software sales at a cybersecurity company to sourcing and closing deals at Constellation Software, one of the most disciplined acquirers in the SaaS world. Guillaume reveals why the best SaaS acquisitions aren’t rushed deals but relationships built over years. He shares how patience, credibility, and consistent founder outreach led to his first acquisition at SaaS Group—a low-profile digital calendar tool called DacBoard—and why targeting under-the-radar SaaS companies can unlock outsized opportunities. The conversation dives deep into today’s hyper-competitive M&A environment, including how to stand out when every founder is being pitched. Guillaume unpacks the red flags most buyers miss, from risky customer concentration to weak net dollar retention, and explains SaaS Group’s clear acquisition framework—capital-efficient, product-led growth businesses with strong fundamentals. The episode wraps with a powerful discussion on how to balance organic growth with acquisitions, avoid overextension, and make smarter strategic decisions when scaling a portfolio of software companies. If you’re serious about SaaS acquisitions, this episode is a must-watch. Click through and watch the full video to learn exactly how Guillaume evaluates, sources, and scales SaaS businesses.   Episode Highlights 02:52 Transition from Sales to M&A Origination 05:52 The Art of Deal Sourcing 09:04 Evaluating Founders and Their Businesses 11:47 Understanding Acquisition Criteria 15:10 Growth Strategies: M&A vs. Organic Growth 18:00 Identifying Red Flags in Due Diligence 21:06 Navigating Operational Complexity 23:57 AI Risks and Opportunities in Software 27:06 Balancing Capital Allocation and Diversification   Key Takeaways ➥ You need to build relationships, build trust, build credibility. ➥ It can take a really long time to acquire a business. ➥ We try to identify red flags as early as possible. ➥ We don't manage our portfolio through spreadsheets; we're not finance people. ➥ Should we buy it? Why? For how much?   About Guillaume Lussato Guillaume Lussato is a senior business development and M&A professional at saas.group, where he helps identify, acquire and scale profitable B2B SaaS companies. He hosts discussions on SaaS M&A, growth, and founder transitions and frequently speaks at industry events about how to grow without VC and what makes SaaS acquisitions succeed or fail. Guillaume focuses on sourcing deals, operational playbooks for scaling post-acquisition, and practical insights that matter to anyone buying online businesses to replace income, scale a portfolio, or prepare for exits.   Connect with Guillaume Lussato ➥ https://www.linkedin.com/in/guillaumelussato/   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

What happens when a seasoned real estate investor steps away from physical property and into the world of digital acquisitions? In this episode, we sit down with Julien Jacques, who made the bold transition from building a real estate portfolio to acquiring online businesses—uncovering both the opportunities and the unexpected mistakes along the way. Julien shares his transparent journey, including his non-traditional Canadian financing strategies, the specific digital business models he targets, and the hard-earned “humble realist” lessons that came from both successful acquisitions and costly missteps. Whether you’re managing rental properties, exploring your first acquisition, or curious about “online real estate,” this conversation delivers a grounded, experience-driven look at what it truly takes to scale in the digital business landscape. Ready to rethink how you build wealth beyond physical assets?  Watch the full episode now!   Episode Highlights 10:51 Lessons Learned in Acquisition 13:28 The Importance of Relationships in Business 16:16 Structuring the Deal 21:01 Navigating Business Financing and Debt 22:11 The Dangers of Overdue Diligence 25:25 Making Decisions with Incomplete Information 29:45 Lessons from a Business Acquisition Failure 36:12 The Importance of Leadership and Networking 40:41 The Journey of an Entrepreneur: Risks and Rewards   Key Takeaways ➥ Real estate can provide passive income but requires management. ➥ Buying an existing business can be less risky than starting from scratch. ➥ Due diligence is important but can be misleading if overanalyzed. ➥ Networking is crucial for entrepreneurial success. ➥ Entrepreneurship requires resilience and adaptability.   About Julien Jacques Julien Jacques is a former real-estate investor and entrepreneur who pivoted into buying online businesses after a year-and-a-half of searching across franchises, retail, and other opportunities. He now owns Rocket Powered Sound, a digital products e-commerce business selling sample packs to music producers, and has firsthand experience in financing, acquiring, and scaling an online company in Canada. Julien’s practical transition from physical assets to “online real estate” gives him a unique perspective on acquisition due diligence, margin dynamics in digital products, and how to turn acquisition opportunities into reliable income streams.   Connect with Julien Jacques ➥ https://www.linkedin.com/in/juljacques/    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

What really kills business deals—without anyone noticing? Not the obvious red flags.Not the spreadsheets.But the quiet mistakes buyers make the moment they think they’ve already won. In this episode, Jaryd Krause sits down with John Martinka (aka The Escape Artist), who’s spent 25+ years advising buyers and sellers across 150+ real acquisitions. No theory. Just what actually happens in deals. You’ll hear why first-time buyers fall in love too fast, how stopping your search early weakens your position, and why relationships matter more than price once negotiations get serious. John also reveals how “great on paper” deals quietly turn into long-term stress, and what to do instead. Plus, what happens after the deal closes: how one small shift helped a buyer grow a business by 75% in under a year, and why growth often fixes problems faster than perfection ever will. If you’re buying a business (or even thinking about it), this episode will change how you see deals before it’s too late. 👉 Watch the full video now and get tips most buyers only learn the hard way.   Episode Highlights 02:45 – Buyer fever explained: why first-time buyers knowingly overpay—and how emotional attachment kills financing and post-close cash flow. 04:10 – Why stopping your search early weakens leverage, increases emotional risk, and makes buyers over-commit before a deal is real. 05:58 – A real $6M deal case study: how choosing the highest offer over the right buyer led to 12+ months of post-close disputes and massive stress costs. 10:05 – Why most deals do close after LOI—and the specific conditions that still quietly cause failures during diligence. 11:20 – Add-backs red flags: why too many adjustments signal risk, credibility issues, and potential tax exposure. 18:10 – Seller priorities revealed: why 90%+ of sellers care more about employee outcomes and legacy than price alone. 21:40 – Earn-outs unpacked: why earn-outs fail when used to justify overpricing—and when they actually make sense. 28:30 – How one compensation change drove 75% revenue growth in under 12 months after acquisition.   Key Takeaways ➥ Don’t fall in love with a business before due diligence. Emotional attachment (“buyer fever”) can lead to overpaying and unrealistic expectations. ➥ Keep your options open. Continuing your search until closing strengthens negotiating power and reduces risk. ➥ Choose the right buyer or seller over the highest price. Alignment of values, motivation, and vision prevents long-term disputes and stress. ➥ Customer concentration risk: Businesses with 2 customers generating ~60% of revenue are extremely vulnerable—loss of one client can collapse cash flow and valuation. ➥ Owner dependency is a hidden risk: Owners working 30–40+ hours per week without robust systems increase acquisition risk; businesses are more valuable when the owner can step away without disruption. ➥ Employee incentives drive growth. Strategic compensation and bonuses can unlock rapid revenue growth without heavy structural changes. ➥ Seller priorities often extend beyond money: Over 90% of sellers care about employee outcomes and business legacy as much—or more—than the final sale price.   About John Martinka John Martinka, known as The Escape Artist®, is a veteran M&A advisor and business strategist. As Co-Founder and Managing Member of Nokomis Advisory Services and Martinka Consulting, he’s guided over 150 business buy-sell transactions and analyzed more than 1,000 companies.  With more than 25 years of experience, John helps executives “escape” the corporate grind by buying businesses the right way, and he also coaches business owners to exit their companies with style, grace, and maximum value. He’s a prolific author (four business books) and speaker, passionate about reducing owner dependency, building systems, and setting up companies to scale or exit profitably.   Connect with John Martinka ➥ https://www.linkedin.com/in/johnmartinka/    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.

Most people don’t fail at buying a business because they’re not smart enough.They fail because—without realizing it—they’re setting themselves up to lose before they even begin. In this solo episode of the BOB podcast, Jaryd Krause goes off-script and gets brutally honest about the real reasons people struggle to acquire online businesses, and why these same patterns show up in money, business, and life. This isn’t a tactical “how-to” episode.It’s a mindset reset. Jaryd breaks down the five biggest reasons people fail at buying a business, drawing from his own journey, his work with buyers around the world, and the patterns he sees repeatedly derail otherwise capable people. You’ll learn: Why you don’t need to know how to run or buy a business before acquiring one How “good” advice becomes dangerous when you treat general guidance as personal truth Why most people are mentally unprepared for the acquisition process—even when they have the money How impatience and unrealistic timelines quietly sabotage deals The uncomfortable truth about why wanting a business isn’t enough—and when change only happens out of necessity Jaryd also dives into cultural differences, ambition, pain as a driver of success, and why some people push through every obstacle while others stall indefinitely. This episode is raw, reflective, and unapologetically real. 🎧 Listen in—and ask yourself whether you’re setting yourself up for success… or failure.   Episode Highlights 01:00 – Why most people unknowingly set themselves up for failure before they even start 06:55 – Myth-busting: Why you don’t need to know how to run or buy a business before acquiring one 10:45 – The danger of “bad” advice and why most guidance is general, not personal 13:55 – Why copying someone else’s timeline almost guarantees failure 18:30 – How unrealistic goals quietly destroy confidence and momentum 20:45 – The mental reality of buying a business and why most people aren’t prepared 24:30 – Patience vs. pressure: why counting inputs matters more than counting time 28:20 – Want vs. necessity: the single biggest reason people fail to follow through 32:40 – How pain, fear, and discomfort actually drive ambition and success   Key Takeaways ➥ You don’t need experience to get started. Most successful buyers had never run or bought a business before their first acquisition. Skills are built during the process—not before it. ➥ General advice becomes dangerous when taken as personal truth. What worked for someone else may not work for you due to differences in time, resources, credit, life stage, and risk tolerance. ➥ Unrealistic timelines create avoidable failure. Comparing your progress to others—or forcing artificial deadlines—leads to disappointment, self-doubt, and unnecessary quitting. ➥ Mental readiness matters more than capital. Buying a business requires patience, resilience, and the ability to handle rejection, uncertainty, and long stretches without visible progress. ➥ Preparation is psychological, not just financial. Due diligence, deal flow, and negotiations are mentally taxing—especially at lower price points where fewer systems and advisors exist. ➥ Stop measuring success by time. Measure inputs instead. Track actions like deals reviewed, conversations held, and due diligence completed. Progress compounds through consistent inputs, not arbitrary deadlines. ➥ Setting the bar too high too early damages confidence.  Low, achievable goals build momentum. Repeated “missed” goals—even small ones—erode belief and motivation over time. ➥ Wanting a better life isn’t enough—necessity creates action. True follow-through happens when change becomes non-negotiable, not optional. ➥ Pain and discomfort are powerful drivers, not problems. Ambition is often fueled by frustration, fear, or dissatisfaction. Learning to harness that energy is key to long-term success.  Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for p

How far can $100,000 really take you in business acquisitions? One deal?A small portfolio?Or a scalable acquisition machine? In this episode, Jaryd Krause sits down with SBA Business Development Officer Glenn Giro to break down the real math behind buying businesses with SBA financing, and why there’s technically no cap on how many businesses you can acquire, as long as you understand the rules that actually stop most buyers. They unpack how entrepreneurs are using up to 90% SBA financing, long 10-year terms, and no prepayment penalties to build portfolios most people assume are out of reach. You’ll discover: How $100,000 in cash can unlock a $1M+ acquisition The $5M SBA cap per NAICS code and how it impacts serial buyers Why banks love SBA loans (and why that matters to you) The real fees lenders don’t explain upfront How cash flow and debt service coverage are actually calculated What changes when you go from your first deal to your second, third, or fifth When 100% financing is possible and when it’s not Why do some high-multiple digital businesses get rejected The timeline lenders expect before approving your next acquisition If you’re serious about buying your first digital business or turning one deal into a portfolio of cash-flowing assets, this episode will completely reframe how you think about capital, leverage, and scale. Watch the full video to see the numbers, strategies, and acquisition pathways most buyers never learn about.   Episode Highlights 02:55 – Why a “simple” 10% down payment can still kill your SBA deal if you don’t understand total project costs. 05:08 – The harsh truth: why $100K is often not enough to safely buy a $1M business. 10:52 – How SBA’s 75% loan guarantee unlocks 90% financing—and why banks are eager to lend. 12:57 – The hidden cost most buyers miss: $20K–$30K in SBA fees on a $1M acquisition. 15:16 – The real reason most buyers can’t buy a second business right after their first. 23:59 – The quiet rule that caps portfolios at $5M per NAICS code—and how it blocks long-term scaling.   Key Takeaways ➥ SBA financing allows buyers to acquire businesses with as little as 10% down, but cash reserves and liquidity matter more than purchase price alone. ➥ The SBA’s 75% government guarantee reduces bank risk and unlocks long-term, high-leverage financing for profitable online businesses. ➥ Seller financing can help bridge equity gaps, but new rules requiring 10-year standby make it rare in competitive acquisitions. ➥ Most buyers need 6–12 months of successful operations before qualifying for a second SBA-backed acquisition—proof of execution accelerates approvals. ➥ Each business must support its own debt service; strong cash flow in one acquisition won’t compensate for a weak second deal. ➥ NAICS code limits quietly shape acquisition strategy—buyers who plan ahead can scale portfolios faster and avoid unexpected financing caps.   About Glenn Giro Glenn Giro is a seasoned SBA business development officer and acquisition financing expert who helps entrepreneurs buy and grow businesses using strategic SBA-backed loans. He hosts “SBA University,” a training series for business owners and aspiring acquirers, and regularly speaks about acquisition financing and business ownership strategies.   Connect with Glenn Giro ➥ https://www.linkedin.com/in/glenn-giro/➥ https://www.youtube.com/@SBAUniversity     Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

In this episode of the BOB Podcast, Jaryd Krause chats with David C. Barnett—author, educator, and all-around small-business acquisition pro. David’s spent 11 years making straightforward videos about buying, selling, and running small businesses, and he’s seen it all. They dive into what most first-time buyers totally miss—like how a “simple” service business pulling in $300–400k a year can still hit you with $10k in unexpected repairs, or how a business that seems hands-off can take up way more mental energy than you expect. You’ll hear things like: 💡 Why lifestyle buyers often crash and how to avoid turning your dream into a money trap⚠️ Even with a manager, some problems are just going to end up on your desk🔧 How one dry-cleaning shop kept a family afloat but still drained the owner mentally😬 What constant staff turnover really means—and the mindset that separates the quitters from the winners🧠 Why corporate experience doesn’t prepare you for small-business chaos📈 Why flipping businesses usually fails, but holding one for 5–6 years can pay off big🤝 Why you need real business friends, not just LinkedIn highlight reels David shares stories from owners who were totally blindsided by the day-to-day reality—turning neglected businesses into assets, and surviving the crazy, unexpected stuff along the way. 🎧 If you want the raw truth about buying a business—no fluff, just lessons you actually need—this episode’s for you.   Episode Highlights 07:07 – How overpaying and operational surprises can sink a business deal. 11:22 – The danger of buying based on emotion, not strategy. 15:30 – How “time on your side” strengthens your acquisition position. 20:15 – Fixing the “leaky bucket” of household finances before buying. 35:56 – Understanding your emotional drivers: lifestyle vs. self-actualization. 43:34 – Buying dreams vs. buying businesses: the B&B cautionary tale. 47:01 – Why running a business is harder than it looks: expectations vs. reality. 51:15 – The real value of small businesses is in long-term ownership, not flipping. 55:04 – Lessons from real owners: hiring struggles and the mindset of persistence.   Key Takeaways ➥ Know your motivation. Buying a business without understanding your emotional drivers — lifestyle, status, or security — can lead to overpaying or making misaligned choices. ➥ Cashflow and leverage are critical. Overpaying or using high leverage without accounting for operational costs and capital expenditure can sink even profitable businesses. ➥ Time is your ally. Build financial strength and patience first. A strong savings habit and a clear understanding of deals over time make you a stronger, less impulsive buyer. ➥ Due diligence saves you. Verify revenue, costs, and seller claims. Skipping checks or relying on emotion leads to costly mistakes. ➥ Lifestyle vs. business reality. Owning a business provides freedom and income, but it always carries operational burdens. Expect hands-on involvement, even with managers in place. ➥ Start with experience. Before buying a business in a new industry, work in it part-time. Real exposure prevents costly surprises. ➥ Value is in ownership, not flipping. Profit comes from running a business over years, not quick resale. Systems, marketing, and management improve long-term returns. ➥ Network with real business owners. Observing how experienced owners handle hiring, challenges, and growth teaches lessons no podcast or post can convey. About David Barnett David C. Barnett is a seasoned business broker, advisor, and educator who has helped aspiring entrepreneurs buy and sell small-to mid-sized businesses since 2009. He is the founder of the Business Buyer Advantage program—a comprehensive training system that guides buyers through finding, analysing, offering on, financing, and integrating a business. David’s background includes business valuation, deal structuring, and a passion for helping people escape the 9-to-5 by owning cash-flowing businesses.   Connect with David Barnett ➥ https://www.businessbuyeradvantage.com ➥ https://www.linkedin.com/in/davidbarnettmoncton    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain a

He’s bought over 15 digital businesses—and learned some lessons the hard way. In this episode of the BOB Podcast, Jaryd Krause sits down with Yury Byalik, a seasoned growth marketer, acquisitions strategist, and digital-business investor who has spent over 15 years building, buying, and scaling profitable online companies. Currently serving as Head of Strategy & Acquisitions at Onfolio Holdings, Yury has mastered the art of spotting opportunities, structuring deals, and growing digital businesses into high-performing assets. But here’s the thing: acquisitions aren’t as simple as signing papers. Mistakes happen—and they can cost you time, money, and growth. Yury shares exactly what to avoid and what strategies actually work. In this episode, you’ll learn:💡 How Yury evaluates a digital business before buying🔧 The most common mistakes first-time acquirers make—and how to sidestep them📈 The growth strategies that turn a purchased business into a profitable, scalable asset🧠 The mindset needed to build a successful acquisition portfolio🤝 Practical tips on integration, operations, and making your acquisitions work together Whether you’re considering your first digital business purchase or looking to scale an existing portfolio, this episode is packed with actionable insights and real-world lessons from someone who’s actually done it—15 times over. 🎧 Plug in and get ready to avoid costly mistakes while accelerating your acquisition journey.   Episode Highlights 07:07 – Why a strong team and legal safeguards can make or break a deal. 09:06 – A shocking story of hidden fraud and non-disclosure. 15:05 – Roll-Up vs. Independent Growth: Yuri shares his selective approach to merging acquisitions 19:00 – Why high‑volume acquisition strategies (e.g., Amazon roll‑ups) often fail. 20:54 – Why waiting 1–3 months can save millions before scaling. 29:41 – How AI commoditization is reshaping valuations across industries.   Key Takeaways ➥ Due diligence is non‑negotiable. Many sellers omit or misrepresent critical information (clients leaving, illegal kickbacks, contract terms). Without a strong legal and analysis team, even “profitable” businesses can become liabilities post-acquisition. ➥ Diversification of traffic and revenue matters. Businesses dependent on a single channel (SEO, ads, Amazon, Google Adsense) are exposed to high risk — a single algorithm or platform change can destroy value. ➥ AI has fundamentally changed valuations. With AI tools reducing the uniqueness of content, and enabling rapid replication of SaaS ideas, multiples on content- or software-based businesses have dropped significantly. That means both risk and opportunity for buyers. ➥ Patience and strategic focus beat volume-based roll-ups. Instead of snapping up every deal, it’s smarter to take time, understand what works inside the business, and selectively scale what’s already strong — especially if you plan to operate (not flip) long-term. ➥ Passion and niche alignment improve acquisition success. Businesses tied to hobbies, communities, or long-term interests tend to perform better when buyers are genuinely invested, because passion translates to better stewardship and resilience through ups and downs. ➥ In attractive niches, speed is everything. When a good business hits the market (clean model, diversified traffic, good margins), multiple buyers are often ready — meaning you need clear, fast decision-making if you want to win the deal.   About Yury Byalik Yury Byalik is a seasoned growth marketer, acquisitions strategist, and digital-business investor with over 15 years of experience building, buying, and scaling profitable online businesses. Currently, he serves as Head of Strategy & Acquisitions at Onfolio Holdings, a public company that acquires and operates a diversified portfolio of digital assets. Before that, Yury worked across digital marketing, SEO, and business law, giving him a unique blend of operational, legal, and deal-sourcing expertise. He is a recognized speaker and contributor on topics such as deal sourcing, acquisition evaluation, and value creation in the online business space.   Connect with Yury Byalik ➥ https://levelfield.io/ ➥https://bridgethegap.ai/   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAm

In this episode of the BOB Podcast, Jaryd Krause sits down with Nick Bradley, a world-renowned author, speaker, and business growth expert known for helping entrepreneurs, business leaders, and investors build, scale, and sell high-value companies. Nick brings more than a decade of Private Equity experience to the conversation. Throughout his career, he has completed over 50 acquisitions, sold 26 businesses, created over $5 billion in value, and played key roles in three exits exceeding $1 billion each. His expertise offers a rare, behind-the-scenes look at what it truly takes to buy, integrate, grow, and exit companies at scale. In this episode, listeners will learn: 💡 The criteria first-time acquirers should focus on 🔧 Nick’s Squared Management System—the four pillars and 40 essential elements that create a solid management foundation 🤝 How to merge two businesses, how long integration takes, and the steps involved in acquiring for growth 🧠 The mindset required for those building a portfolio through acquisition 📈 The characteristics of successful portfolio builders, including why “boring” businesses often become the most profitable For anyone considering growth through acquisition or curious about how seasoned investors strategically scale companies, this episode provides the insights and frameworks needed to navigate the world of M&A with confidence.   Episode Highlights 02:10 –  Why Founders Struggle? 04:41 – Strategic vs. Financial Value: Understanding "The Buyer’s Math"  07:00 – Build Your Business To Be Sellable 09:21 – What PE Firms Do Differently: Discipline, Detachment & Focus   Key Takeaways ➥ Most founders misunderstand what truly drives business value. They tend to focus on revenue or profit, but in reality, those are only about 40% of the valuation—60% comes from operational, strategic, and structural factors that founders often overlook. ➥ Sophisticated buyers play a different game. Private equity firms and large acquirers buy and sell companies constantly. They know the rules, the metrics, and the process far better than most founders who are going through a once-in-a-lifetime sale. ➥ Value is based on the buyer’s math, not the seller’s. Strategic buyers care about customer bases, distribution, systems, capability, geographies, and integration potential, not just financial performance. Founders must understand what their business is worth to the buyer. ➥ A business should always be built to be sellable—even if you never sell. A well-built business creates freedom, independence, and optionality. When a sale opportunity comes, you’ll be in the best position to maximize value. ➥ Private equity excels because of emotional detachment and absolute focus. PE firms operate with military-level discipline—no emotional decision-making, full clarity on end goals, and a strict focus on executing a plan that increases value fast. This contrasts with founders who are often emotionally attached to their business.   About Nick Bradley Nick Bradley is a world-renowned author, speaker, and business growth expert who works with entrepreneurs, business leaders, and investors to build, scale, and sell high-value companies. After spending a decade in Private Equity, Nick has seen the ups and downs of business growth and the key challenges that impact business performance. During that time, he completed over 50 acquisitions, sold 26 businesses, and created over $5bn in value. He has personally been involved in 3x exits valued at over $1bn each. Nick believes that scaling and eventually selling your business isn’t a “game of chance”. With guidance and support, your business can navigate the complexities of markets, scale efficiently, attain business goals that match your vision, and achieve an outstanding exit that reflects the hard work you have invested in your journey. He also believes in leveling the playing field with sophisticated buyers, such as Private Equity, equipping business owners with the strategies and tools to compete in the fierce world of M&A … and win the game.   Connect with Nick Bradley ➥Nick’s LinkedIn: linkedin.com/in/realnickbradley ➥ Exit Your Business For Millions - Download This Guide: https://go.highvalueexit.com/opt-in    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJA

Think a million-dollar online business is out of reach?  The real barrier isn’t the price—it’s everything you don’t see coming before you even sign. In this solo episode, Jaryd Krause pulls back the curtain on the part of buying a 7-figure business that almost nobody talks about—the real costs, the real timelines, the real competition, and the parts of the process that can quietly wreck your deal long before you ever get to the closing table. Most people assume a $1M acquisition is simple math:Find the business, put down the deposit, sign some papers, done. But behind every one of those deals are fees, structures, advisors, lenders, deadlines, and expectations that—if you’re not prepared—will eat your budget and your sanity alive. Here’s what Jaryd gets into: 📌 The actual line-item expenses of buying a 7-figure business (legal, advisors, due diligence,  escrow, lender fees—yes, all of it) 📌Why doing a smaller deal doesn’t necessarily make anything easier and why some “cheap” deals cost more in mistakes 📌How the right deal structure can turn upfront costs into credits that reduce what you owe at closing 📌 The role of buyer-side advisors —what they charge, what they’re worth, and when you shouldn’t hire one 📌 The hidden criteria lenders use to judge your deal that most buyers don’t even know they’re being evaluated on 📌 Why timelines are never linear and competition is always sharper at the top 📌 The mindset traps that sabotage buyers and how patience becomes the most profitable strategy you have   Jaryd doesn’t dress it up. He walks you through the real picture—what it costs, what’s negotiable, what’s risky, and what will give you an edge when everyone else is rushing and guessing. If you’ve ever wondered whether you can actually afford a million-dollar acquisition, consider this your roadmap—and your reality check. 🎧 Plug in. This one will change the way you look at buying a business.     Episode Highlights 01:15 – Differences between sub-$500K deals vs seven-figure acquisitions 02:24 – Key costs when buying a seven-figure business 04:52 – Why do you need a specialized M&A lawyer? 07:13 – How to structure legal packages for letters of intent, asset purchase agreements, and contract due diligence 16:56 – Why larger businesses can be easier to acquire despite higher costs, and how cash flow impacts returns 19:22 – How long it can take to close a seven-figure business deal and factors affecting timing 21:40 – Cash vs. financed deals: the impact on negotiation power and deal structure 23:55 – Setting realistic expectations and why compounding small wins builds confidence in acquisitions 26:17 –  Why do you need to work with experts?     Key Takeaways ➥ Legal fees for M&A lawyers usually run 1–2% of the deal, and using an experienced online business acquisition lawyer is essential. ➥ Finance broker fees range from $5K–$10K, with SBA or lender fees around 3.5–3.75% of the financed amount, often rolled into the loan. ➥ Buyer-side advisors (3–8% of deal size) can review due diligence, advise on deal structure, negotiate, and sometimes source pre-vetted businesses. ➥ Due diligence packages ($5K–$40K) and escrow (~1% of acquisition) are key costs, but many upfront fees can be credited toward your deposit. ➥ With smart planning, many upfront costs—legal, advisor, and broker fees—can be credited toward your deposit, allowing acquisition with just 10% cash down. ➥ The larger the business, the more leverage you have, and the more stable the cash flow. Entry costs scale, but ROI potential often increases with size. ➥ Acquisition timelines vary widely—sometimes months, years—depending on market availability, acquisition criteria, and competition. Patience is key. ➥ Set realistic expectations. Overly ambitious goals or standards can harm mindset and decision-making. Compounding small wins builds confidence and sustainable success.  Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAm ➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost

What if the one thing stopping you from owning a thriving online business isn’t money… but what you don’t know about SBA financing?  In this episode, Jaryd Krause chats with Ray Drew—aka SBA Ray—host of The Art of SBA Lending, the #1 podcast that pulls back the curtain on how SBA loans really work. Ray is the Managing Director at Truliant Federal Credit Union, a deal closer with hundreds of successful SBA-financed businesses under his belt, the man behind millions in SBA-backed deals, and the architect of SBA success stories nationwide. He’s seen everything—the smooth wins, the total nightmares, and the deals that fell apart days before closing. Most people think an SBA loan is simple: apply, get approved, buy the business, boom—you’re a CEO.  But the truth?  There are traps hidden in plain sight. And missing just one could cost you the deal—or tens of thousands in wasted time and fees. Here’s what Ray and Jaryd dive into: 🔥 The hidden misconceptions that trip up first-time buyers (even the smart ones)🔥 Why your “perfect” deal structure could actually kill your loan approval🔥 The truth about interest rates, balloon payments, and seller financing nobody tells you🔥 What really happens behind the scenes when lenders assess your deal🔥 The surprising reason your loan might get rejected even if you’re qualified 🔥 How long does the process really take—and what delays can quietly blow up your timeline🔥 Why the right M&A attorney can save your deal when everything’s on the line Ray doesn’t sugarcoat it—he breaks down exactly what’s going wrong in the SBA space and what you need to know before you sign anything. If you’ve ever dreamed of acquiring an online business but didn’t know how to fund it, this is your reality check and your roadmap. Because when it comes to SBA lending, it’s not just about money… It’s about knowing the game before you play it. 🎧 Grab your headphones. This one could save your next deal.   Episode Highlights 01:12 – What SBA lending is and why it’s a game-changer for business buyers 06:40 – Why buying a business often beats starting from scratch 09:24 – The most common misconceptions about SBA loans 12:10 – Key factors lenders look for before approving a deal 15:32 – The #1 mistake buyers make during the SBA loan process 18:46 – How to choose the right lender and build a strong relationship 21:55 – Real stories from hundreds of SBA-financed deals—the smooth, the messy, and the ones that fell apart 25:08 – How does the deal structure and negotiation impact loan approval 28:26 – Why preparation is the real secret to fast, successful closings 31:47 – Ray’s process for evaluating if a business is truly financeable 34:15 – Lessons from deals that went wrong—and how to avoid the same pitfalls 37:28 – What every buyer should do 6–12 months before applying for an SBA loan 39:52 – Ray’s best advice for entrepreneurs who want to acquire a business in 2025   Key Takeaways ➥ SBA financing is one of the most powerful yet misunderstood tools for buying a business—it lets entrepreneurs acquire profitable companies with as little as 10% down. ➥ Preparation is everything. Clean financials, accurate tax returns, and a solid business plan can drastically increase your chances of getting approved. ➥ The right lender matters more than most realize. Experienced SBA lenders can structure deals creatively, solve problems quickly, and close with confidence. ➥ Not all deals are created equal—lenders look for stable cash flow, strong management transitions, and businesses with proven profitability. ➥ Expect surprises. Even well-structured deals can fall apart near closing, so patience, flexibility, and expert guidance are essential. ➥ Buying a business with SBA financing isn’t just about getting a loan—it’s about acquiring a long-term wealth vehicle that can transform your financial future. ➥ Execution beats theory. Ray’s track record proves that the best buyers are those who take action, learn from each deal, and build relationships with trusted lenders.   About Ray Drew Ray Drew is the SBA Managing Director at Truliant Federal Credit Union, where he helps entrepreneurs buy businesses through SBA financing. With over a decade in the industry, Ray has closed hundreds of deals and is widely regarded as one of the leading voices in SBA lending today. He is also the host of the #1 podcast in the SBA lending industry, The Art of SBA Lending.   Connect with Ray Drew ➥ www.sbaray.com ➥ https://www.youtube.com/@SBA_Ray    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.c

Most people guess marketing tricks—but Andri Sadlik knows the shortcuts, the pitfalls, and the moves nobody talks about. In this episode, Jaryd Krause sits down with Andri Sadlik, a pro at scaling SaaS, AI, and e-commerce businesses. Andri launched his first business and exited successfully. After that, he scaled multiple Amazon FBA brands from $100K a year up to $1M, and finally over $10M. No gimmicks, no luck—just carefully built systems, a strategy that makes sense, and teams that execute like clockwork. He’s also the co-founder of ProductPinion, a SaaS company he’s planning to exit, and has been featured in top media outlets for his expertise in scaling businesses. In this conversation, you’ll hear how he: 🚀 Built and sold his first business—without repeating rookie mistakes 🚀 Survived a broker nightmare—and came out ahead 🚀 Took Amazon brands from $100K → $1M → $10M+ 🚀 Created influencer programs that generate real ROI 🚀 Scales multiple businesses by connecting teams, systems, and plans Andri shares the challenges, the wins, and the step-by-step strategies that helped him grow an impressive portfolio of businesses. If you want actionable insights on scaling, selling, or acquiring e-commerce businesses, this conversation is packed with value. Tune in and learn how to take your business from 0 to 8-figures—and avoid the mistakes that can cost you big.   Episode Highlights 01:04 – How Andri sold his 3-year-old Amazon FBA business in 2020 03:07 – How to vet brokers carefully 07:30 – How to prep for business exit prep 12:58 – The post-acquisition success story 16:41 – How to bring new customers with minimal effort while complementing existing PPC spend. 23:06 – Secret hack for driving real conversions. 27:36 – Why experience matters   Key Takeaways ➥ Selling a business isn’t just about the exit—it’s about preparation. Optimizing operations, cleaning up books, and systemizing processes can dramatically increase value before you sell. ➥ Choosing the right broker is critical. Some may prioritize buyers over sellers, so triple-check their process and talk to previous clients to avoid surprises. ➥ Price smart: list slightly higher than you expect to sell. Buyers usually negotiate down, and a higher starting point protects your upside. ➥ Post-acquisition growth thrives on systems and expertise. Optimizing listings, ads, inventory, and operations can double revenue—even for a brand bought for “super small” amounts. ➥ Recurring purchase models are gold. Consumable products, repeat buyers, and brand loyalty can accelerate growth faster than flashy campaigns. ➥ Leveraging influencer programs strategically—segmenting creators, VIPs, and deal groups—can drive 11%+ of sales without heavy spend. ➥ Continuous experimentation, collaboration, and smart use of customer feedback unlock unexpected growth. Even small tweaks to processes or partnerships can massively scale results.   About Andri Sadlak Andri Sadlak is the Head of Product & Strategy leader with a track record of building and scaling SaaS, AI, and e-commerce businesses. Scaled  8-figure portfolio, co-founded a Saas company called ProductPinion, and has featured in many media publications talking about scaling online businesses..   Connect with Andri Sadlak ➥ https://www.linkedin.com/in/sadlak/    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

What if you could turn a $5K/month business into $80K/month in under a year? That’s exactly what Chan Yuenenyi did. In this episode, Jaryd Krause chats with the founder and CEO of EssayGrader AI—the world’s leading AI grading platform trusted by over 100,000 educators. When Chan bought the business, it was generating only $5,000 per month. Fast-forward less than a year later, and he’d scaled it to $80,000/month, hitting $1M in annual recurring revenue. But here’s the twist: Chan didn’t chase shiny tactics or massive ad budgets.He used precision. Systems. Deep understanding of what users actually need. Before founding EssayGrader AI, Chan managed a billion-dollar product line at OpenText. So, he knew one thing most first-time buyers miss—buying a business is easy. Growing one takes vision. In this conversation, you’ll discover how he: 🔥 Spots red flags before closing a deal🔥 Turns customer feedback into a growth engine🔥 Shifted from “operator” to “owner”🔥 Discovered the single most powerful strategy behind his $5K → $80K leap🔥 Built what he calls “inside-out growth”—and why it changes everything This isn’t just a story about scaling. It’s about clarity, focus, and designing a business that grows because it serves people better. If you’re looking to buy your first SaaS—or scale the one you already own—don’t miss this one.It’s packed with real lessons from someone who’s actually done it.   Episode Highlights 08:08 – Chan reveals his process of evaluating 25–30 businesses over 90 days, learning to identify patterns, red flags, and what truly matters when choosing the right acquisition. 13:56 – Why product-market fit and traction matter more than polished features or perfect design when evaluating early-stage SaaS. 15:51 – Chan breaks down the valuation and deal structure—he bought SAGrader.ai for $125K in cash at a 2x revenue multiple. 19:46 – Red flags to watch for when buying a business—no traction, unclear customer base, lack of competitors, or overbuilt products. 27:42 – How involving users in building new features turned customers into loyal advocates and multiplied sales through word of mouth. 28:27 – The impressive growth story—from $5K to $80K MRR in a year—by focusing on fundamentals and customer insights over flashy marketing tactics. 30:34 – Why execution beats information overload: Chan’s advice to stop chasing every online guru and start acting on core business principles.   Key Takeaways ➥ Acquiring an existing SaaS business offers a faster, lower-risk entry into entrepreneurship compared to starting from scratch, letting you focus on growth instead of setup. ➥ Evaluating dozens of deals before buying helps refine your investment instincts—each review teaches you how to spot red flags, assess traction, and recognize scalable opportunities. ➥ Product-market fit is the single most important factor in acquisition success; without genuine demand and active users, no amount of marketing can sustain growth. ➥ Direct customer communication—through live chat, feedback loops, or support channels—unlocks powerful insights that shape product improvements and retention. ➥ Growth doesn’t come from adding complexity but from deeply understanding your users and iterating based on their real-world needs. ➥ Cash deals can streamline acquisitions and build seller trust, though they require strong conviction in your due diligence and vision for growth. ➥ Listening, testing, and improving continuously can turn a modest $5K MRR business into an $80K MRR success—proof that fundamentals and focus outperform flashy tactics. About Chanakya Yerneni Chan Yerneni who is Founder & CEO of EssayGrader AI, the #1 AI grading platform trusted by 100,000+ educators to save 10+ hours every month grading student submissions. Former Senior Product Marketing Manager at OpenText ($1B+ product). Connect with Chanakya Yerneni ➥ https://www.essaygrader.ai/ ➥ https://www.linkedin.com/in/chanakya-yerneni-338869378/   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Hostinger (Website Hosting) - https://bit.ly/3HUqW0s ➥ Surfer SEO (SEO tool for content writing) - https://bit.ly/3WWMKjM ➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3

It’s not the numbers that make a business thrive—it’s the people, the trust, and the purpose behind it. In this revealing episode, Jaryd Krause sits down with Antoine Minoux, Principal Product Designer at Yelp and a serial entrepreneur who has founded, grown, and sold multiple successful SaaS ventures, including Improvmx and VoilaNorbert. Together, they unpack what really happens behind the scenes of buying, scaling, and selling online businesses—and the emotional intelligence required to do it right. Antoine shares his candid reflections on navigating acquisitions, from spotting undervalued opportunities to balancing multiple ventures and knowing when it’s time to sell. They explore how trust and transparency form the foundation of any successful deal, why valuation isn’t just about numbers, and how emotional awareness can be the difference between a smooth exit and a painful one. Through Antoine’s firsthand experiences, this conversation provides a roadmap for entrepreneurs looking to grow not just through innovation but through strategic acquisition and authentic relationships. Together, they explore: ✔️ Why buying an existing business can be less risky than starting from scratch✔️ The emotional and relational side of business acquisitions most founders overlook✔️ How to balance multiple ventures without losing clarity or momentum✔️ The right way to approach valuation and negotiation in SaaS deals✔️ Lessons learned from multiple exits—and why selling doesn’t always mean letting go Whether you’re an aspiring acquirer, a seasoned founder, or somewhere in between, this episode will challenge how you think about growth, exits, and the role of trust in entrepreneurship. 🎧 Tune in to discover how Antoine Minoux built and exited multiple SaaS businesses by combining strategic thinking with human-centered design—and how you can too.   Episode Highlights 02:50 – Why acquisition can outperform starting from scratch: understanding risk reduction and leveraging proven systems for faster growth. 08:24 – Lessons from multiple exits: what Antoine learned about timing, valuation, and emotional readiness. 16:23 – Knowing when to sell: the strategic and personal factors that influence exit decisions. 19:26 – Balancing multiple ventures: how to manage creative energy, focus, and burnout when running several businesses. 22:02 – Smart valuation strategies: combining upfront cash flow with future performance for sustainable exits. 24:44 – Evolving as an entrepreneur: how experience shapes acquisition instincts and strategic clarity. 29:52 – Redefining the meaning of an exit: why selling a business doesn’t always mean walking away from your vision.   Key Takeaways ➥ Buying an existing business often offers a safer and faster path to success than starting from zero. ➥ Trust and transparency aren’t just values—they’re strategic advantages in high-stakes transactions. ➥ Emotional awareness is critical during acquisitions and exits; ego-driven decisions can destroy deals. ➥ A great valuation balances immediate returns with long-term performance and relationships. ➥ Experience in your industry dramatically improves your ability to identify and grow profitable opportunities. ➥ Exiting a business can be a transformation, not a goodbye—many founders stay involved in new, more strategic ways. ➥ Growth through acquisition requires both strategic thinking and emotional intelligence—one without the other leads to imbalance.   About Antoine Minoux Antoine Minoux is a Principal Product Designer at Yelp and an Indiepreneur currently living and working in Hamburg. He successfully founded, designed, grew, and sold multiple bootstrapped SaaS companies like Voilanorbert.com and Improvmx.com. He is now working on Fernand, the ultimate custom messaging tool for modern SaaS.   Connect with Antoine Minoux ➥ https://www.linkedin.com/in/antoineminoux/  ➥ ww.getfernand.com - Link to Ep 339 with Matthew Tse, the Acquirer of ImproxMX   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Cloud Ways (Website Hosting) - https://bit.ly/40tjyjG ➥ SEM Rush (SEO tool) - https://bit.ly/3lINGaV ➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small c

Business success isn’t just about buying the right company—it’s about building the right foundation. In this insight-packed episode, Jaryd Krause sits down with Brian and John, two entrepreneurs who’ve mastered the art of acquiring and scaling online businesses through mentorship, strategic planning, and sustainable growth. From their first steps into e-commerce to managing complex acquisitions, Brian and John share how having the right mentor, team, and financial structure can make or break a deal. They pull back the curtain on what it really takes to grow an online business—revealing how patience, education, and teamwork pave the way for long-term success in a fast-changing digital economy. Together, they unpack: ✔️ The role of mentorship in accelerating business growth and confidence✔️ How to build diverse revenue streams that stabilize your portfolio✔️ Financial planning fundamentals every buyer needs before acquisition✔️ Why a strong team and legal support system are non-negotiable✔️ The mindset shift from “buying a job” to “owning a business”✔️ How customer feedback fuels innovation and operational improvement✔️ Building systems that scale—and keep your business sustainable Through candid reflections and hard-won lessons, Brian and John offer a blueprint for entrepreneurs who want to expand strategically while avoiding the burnout and chaos that often follow growth. Whether you’re an aspiring buyer or already running multiple online ventures, this episode will equip you with the mindset and structure to scale with confidence. 🎧 Tune in to learn how to design your business for growth, master your numbers, and build a team that frees you to focus on your next big move.   Episode Highlights 05:31 – Navigating acquisitions: lessons learned from evaluating, negotiating, and structuring successful deals. 08:26 – Building your inner circle: why legal, financial, and operational support are essential for scaling. 11:23 – Overcoming acquisition hurdles: managing uncertainty, setbacks, and the emotional rollercoaster of business buying. 22:39 – Planning ahead: aligning goals, systems, and strategy for sustainable expansion. 34:30 – Systems thinking: creating repeatable processes that build resilience and scalability. 35:19 – The power of partnership: how trust and complementary skills strengthen business outcomes. 38:25 – Hard-won wisdom: advice for first-time buyers on patience, preparation, and perspective. 41:00 – Education as an edge: how continuous learning fuels smarter investments and growth. 48:12 – The road ahead: building a sustainable, diversified business portfolio with long-term impact.   Key Takeaways ➥ Mentorship accelerates mastery. The right guidance can save years of trial and error. ➥ Understand your numbers. Financial clarity is the foundation of every successful acquisition. ➥ Build systems, not chaos. A strong operational structure allows growth without burnout. ➥ Customer feedback is your compass. Listening to your audience drives smarter innovation. ➥ Teamwork scales success. A capable team frees you from the daily grind and fuels sustainable growth. ➥ Stay curious. A beginner’s mindset keeps you adaptable in an evolving e-commerce landscape.   About John & Brian John & Brian are BuyingOnlineBusinesses.com graduates, online business owners, and acquisition entrepreneurs. They have a high 7-figure ecommerce business and also acquired another 7-figure online business with Jaryd Krause as their M&A advisor to add to their portfolio of businesses. They are achieving great things and have even bigger goals that they are well on their way to achieving through business acquisition and growth.    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Surfer SEO (SEO tool for content writing) - https://bit.ly/3WWMKjM ➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P   Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Buying a business is one thing—but knowing how to actually grow it is where the real challenge (and opportunity) begins. In this episode, Jaryd Krause chats with Matthew Person, a corporate strategist, investor, and M&A expert who’s mastered the art of scaling through acquisition. With experience across investment banking, corporate development, and private equity, Matthew knows what it takes to turn good businesses into great ones. He’s the mind behind the Square Management System, a framework built to help entrepreneurs align culture, structure, and strategy so growth happens seamlessly—not chaotically. In this episode, you’ll learn: ✔️ Why understanding customer lifetime value is more important than acquisition cost✔️ How pricing and packaging decisions influence business scalability✔️ What makes the Square Management System a powerful tool for growth✔️ The critical role of cultural fit in M&A integration✔️ How to manage different revenue types and their impact on valuation✔️ Why boring businesses often yield the best returns✔️ The common integration challenges—and how to plan for them✔️ What successful portfolio builders do differently from the rest Jaryd and Matthew break down the real drivers of business success, from understanding customer lifetime value and pricing strategy to building systems that make integration smooth and scalable. Whether you’re eyeing your first acquisition or managing a growing portfolio, this episode shows you how to scale smarter, not harder. 🎧 Tune in to learn how to build, buy, and scale businesses the smart way—through systems, strategy, and structure.   Episode Highlights 09:17 – The Square Management System: Matthew’s proven framework for scaling businesses through structure, culture, and alignment. 14:10 – Lessons from investment banking: insights on spotting hidden value and capturing upside in every deal. 18:52 – Smarter deal structures: balancing growth potential with risk mitigation to protect your investment. 21:15 – The magic of recurring revenue: how predictable income streams boost valuation and stability. 23:38 – The art of integration: navigating the human and operational challenges that make or break acquisitions. 29:05 – Culture as the glue: why cultural fit is essential for seamless post-acquisition success. 33:37 – Scaling through systems: how effective management systems create control, consistency, and scalability. 37:38 – Portfolio builders’ mindset: the habits and principles of investors who consistently grow thriving portfolios. Key Takeaways ➥ Growth by acquisition starts with deep customer and market understanding, not spreadsheets. ➥ Retention drives profitability—a loyal customer base is the real engine of value. ➥ A clear pricing strategy can multiply growth potential without new customers. ➥ Culture eats strategy for breakfast—successful integrations start with people, not processes. ➥ Investment banking experience gives you the lens to structure smarter, safer deals. ➥ Different revenue types (recurring, transactional, hybrid) shape how your business is valued and scaled. ➥ The Square Management System offers a blueprint for scaling operations across multiple brands.   About Matt Person Matt Person is a seasoned corporate strategist, investor, and M&A expert with over 25 years of experience helping companies build and capture enterprise value. Currently SVP of Corporate Development at Quickbase (a Vista Equity-backed SaaS platform), he also founded Town Square Advisors, where he created the Square Management System: a proprietary framework that drives high performance through alignment, culture, and organizational design built on constrained independence.  Prior, he led global corporate development, deal execution, and growth strategy for enterprise SaaS firms like IDG and Green Street Advisors, as well as worked in investment banking and strategy consulting. Matt combines deep technical and financial expertise with operational leadership and a passion for building winning teams. On this episode of the Buying Online Businesses Podcast, he shares how you can not only buy and scale online businesses, but also structure them and your own mindset to replace your income and craft a life of freedom.   Connect with Matt Person  ➥ www.townsquare-advisors.com   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Surfer SEO (SEO tool for content writing) - https://bit.ly/3WWMKjM ➥ Ezoic

Success in business isn’t just about strategy—it’s about mindset. In this performance-driven episode, Jaryd Krause sits down with Itamar Marani, one of the world’s leading high-performance mindset coaches, to unpack why so many entrepreneurs unknowingly sabotage their own success when buying, growing, or scaling online businesses. A former Israeli Special Forces operative, the youngest federal agent and air marshal in Israel’s history, and a Brazilian Jiu-Jitsu black belt, Itamar has coached hundreds of six to nine-figure entrepreneurs, executives, and elite athletes to break through mental barriers, eliminate self-sabotage, and operate at their peak under pressure. His clients have exited companies for nine figures, raised hundreds of millions in capital, and ranked among the top performers in their industries. Together, Jaryd and Itamar dive deep into the psychology of performance, exploring: ✔️ The three biggest bottlenecks holding entrepreneurs back from success✔️ How to identify the most direct path to your goals—and stay on it✔️ The top three performance traps that stop business owners from scaling✔️ Why even experienced buyers struggle after acquisition—and how to fix it Through real-world examples from Itamar’s military and coaching experience, you’ll discover how to spot the patterns of self-sabotage that quietly derail deals, limit growth, and block financial freedom. Whether you’re preparing to buy your first online business, scale an existing one, or build a portfolio, this episode reveals the mindset frameworks that separate high performers from those stuck in perpetual struggle. 🎧 Tune in to learn how to master your mental game, eliminate hidden obstacles, and finally unlock the success that’s been just one step away.   Episode Highlights 02:41 – The most direct path to success: identifying high-leverage actions instead of chasing complexity or distractions. 08:12 – Common success killers: self-sabotage, procrastination, and the subtle traps that derail high performers. 13:51 – The fear of not being ready: unpacking the mindset that stops many entrepreneurs from taking bold action. 24:26 – Balancing emotional comfort with the uncertainty of growth and why detachment is a key entrepreneurial skill. 30:08 – Performance traps: the myth of “working harder” and how the go-harder mentality leads to burnout. 37:41 – Strategic approaches to business growth: recognizing emotional bottlenecks that limit scale.  48:08 – The mindset mastery framework: practical tools to overcome internal blocks and build resilience.   Key Takeaways ➥ The biggest limiting belief in business is the “I’ll be ready once…” mindset. You already have what you need to take the next step. ➥ Identify your most direct path to success by asking, “What would someone else—less skilled or experienced—need to do to achieve this goal?” ➥ Emotional detachment is a superpower; it helps you make clear decisions without fear or bias clouding judgment. ➥ Seeking approval is deeply human, but when unmanaged, it leads to poor negotiations, people-pleasing, and self-sabotage. ➥ Performance traps like “just push harder” often backfire. Sustainable success requires rest, recovery, and self-awareness. ➥ Self-sabotage isn’t a flaw—it’s a signal. The key is understanding which mental model or emotional loop is driving your decisions.   About Itimar Marani Itamar Marani Itamar Marani is regarded as one of the top performance and mindset coaches in the world. He’s a former Israeli Special Forces operative, the youngest federal agent and air marshal in Israel’s history, a Brazilian Jiu-Jitsu black belt who’s competed at a world-class level, and a mentee of the Mossad’s chief psychologist.  He has since coached hundreds of 6–9 figure entrepreneurs, executives, traders, and pro athletes to break through performance plateaus, eliminate mental drag, and operate at their highest level under pressure. His clients have exited companies for nine figures, raised hundreds of millions of dollars, and entered top ten rankings in the world, among other results.   Connect with Itamar Marani  ➥ https://itamarmarani.com ➥ https://itamarmarani.com/book ➥https://buyingonlinebusinesses.com/ep-240-how-emotional-intelligence-is-your-secret-weapon-to-unlocking-your-greatest-potential-in-business-with-itamar-marani/    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusiness

Scaling an e-commerce business from six to seven figures is an exciting milestone—but it’s also where many founders hit costly roadblocks. In this insightful episode, Jaryd Krause sits down with award-winning e-commerce mentor Jodie Minto, founder of the seven-figure fashion brand iland co., host of the Online Store Success podcast, and certified digital marketer, Meta Ads specialist, and life coach. Jodie built her global fashion label from scratch while raising a young family, working full-time, and living in the Middle East—before scaling it to seven figures with customers and stockists around the world. Together, they dive deep into what it really takes to grow an e-commerce business beyond six figures, avoid the biggest pitfalls along the way, and prepare for a successful exit. Jodie shares her unfiltered journey of scaling and then strategically de-scaling her brand, the lessons from her first failed exit attempt on Flippa, and how she ultimately secured an all-cash sale to an outside buyer. You’ll learn: ✔️ The two biggest mistakes brands make when trying to jump from six to seven figures✔️ Why scaling too fast can backfire—and how to know when to pull back✔️ The mindset traps that lead to burnout and how to avoid them✔️ What to expect when selling your business (and how to recover if a deal falls through)✔️ How to align business growth with life goals for long-term fulfillment Whether you’re scaling toward seven figures, planning for an exit, or simply want a healthier approach to growth, this episode is packed with practical insights from someone who’s been through it all.  🎧 Tune in to discover how to scale smarter, sidestep common mistakes, and set your business up for lasting success.   Episode Highlights 05:15 – The early challenges of manufacturing, distribution, and scaling operations in the fashion e-commerce space. 09:14 – Burnout, exhaustion, and the difficult decision to sell her business despite years of effort and growth. 25:06 – The costly mistakes founders make when scaling—such as overcommitting to leases, staff, or luxury expenses. 29:18 – Building systems that allow freedom: how to design businesses that thrive without the founder’s constant presence. 31:00 – Paid ads as gasoline on what already works, and why they can’t fix fundamental conversion problems. 34:35 – How to improve conversion rates by simplifying “click, click, buy” and removing common objections like unclear shipping, returns, or sizing. 38:00 – Product-market fit: why proven, desirable products should be prioritized before scaling ad spend.   Key Takeaways ➥ Building an e-commerce business requires patience, adaptability, and resilience—especially when scaling introduces new operational challenges. ➥ Burnout can be a signal that it’s time to reassess or even exit; knowing when to let go is as important as knowing when to push forward. ➥ Scaling too quickly with fixed overheads like leases, staff, or luxury purchases can cripple profitability; stay lean and flexible. ➥ Effective paid ads amplify what already works—they’re not a fix for poor products, broken websites, or unclear messaging. ➥ Strong ad creative is crucial; speak directly to customer benefits rather than product features to cut through the noise.   About Jodie Minto Jodie Minto is an award-winning e-commerce mentor, founder of a seven-figure fashion brand, iland co., podcast host, and speaker based on Australia's Central Coast of NSW. Jodie is also a certified Digital Marketer, Meta Ads Specialis,t and Life Coach. Jodie started her online fashion store from scratch while working full-time, juggling young kids, and living in the Middle East. Today, that business, iland co., is a seven-figure online brand with stockists and customers worldwide. Jodie sold that business in 2023 and now supports other women in growing their e-commerce businesses through her coaching programs. Jodie also hosts the popular e-commerce podcast Online Store Success, which reached number 2 in marketing podcasts in Australia for two weeks straight and frequently sits in the top 30 in Australia, Europe, the Middle East, and the United States.   Connect with Jodie Minto  ➥ https://www.jodieminto.com/  ➥ https://www.instagram.com/iamjodieminto/     Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Surfer SEO (SEO tool for content writing) - https://bit.ly/3WWMKjM ➥ Ezoic (Ad Network) - http

Get ready to discover a whole new way for people to find your business online at the forefront of the AI revolution in this insight-packed episode. Joining the conversation is Dom Wells, Founder & CEO of Onfolio Holdings (NASDAQ: ONFO), a public holding company for profitable online businesses. After acquiring an SEO agency, Dom turned it into a smart new service called Generative Engine Optimization (GEO) — helping businesses show up inside answers, tips, and conversations from tools like ChatGPT, Bing Copilot, and Claude. GEO is changing how brands get noticed in 2025 and beyond. Instead of just showing links, AI tools give people clear answers. GEO makes sure your business is part of those answers, so you’re seen where customers are already looking. In this episode, you’ll find out: How GEO is different from old-school SEO. Why AI search feels more helpful and personal than regular search engines. Simple ways to check and boost your visibility in tools like ChatGPT and Bing Copilot. Real stories of businesses getting fast results with GEO — plus how to grab free audits and tips shared during the show. 🎧 Tune in to explore how mastering GEO can position your business ahead of the competition and right into the spotlight of AI-driven discovery.   Episode Highlights 09:05 – Why GEO matters in 2025: AI assistants are replacing search engines as the go-to for answers and recommendations. 13:25 – How ChatGPT, Bing Copilot, and other LLMs weigh authority and context differently from Google’s link-based rankings. 22:30 – Building credibility for GEO: why brand mentions, authentic discussions, and trusted sources matter more than backlinks. 33:35 – Case studies reveal GEO’s speed: top AI recommendations and tripled Reddit traffic achieved in just weeks. 41:14 – Matching platforms to your niche—Reddit, Wikipedia, or forums—improves relevance in generative search results. 42:23 – Looking ahead: how GEO will evolve as AI search expands, and why staying agile keeps brands visible.   Key Takeaways ➥ Generative Engine Optimization is essential for brands that want to appear in AI-generated answers, not just search listings. ➥ Large language models reward credibility, context, and recency, creating new levers for visibility beyond backlinks. ➥ Auditing how AI tools surface your brand helps pinpoint weaknesses and uncover fast growth opportunities. ➥ Engagement on high-trust platforms—Reddit, Wikipedia, or niche forums—can strongly influence recommendations from ChatGPT and similar tools. ➥ GEO delivers results quickly, making it a valuable complement to SEO’s slower, compounding gains.   About Dom Wells Dom Wells is the founder and CEO of Onfolio Holdings, Inc. (Nasdaq: ONFO), a public holding company of small profitable online businesses.   Connect with Dom Wells ➥ Free Audit! - https://pacegenerative.com/prtnr/2538/➥ Onfolio.co    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Surfer SEO (SEO tool for content writing) - https://bit.ly/3WWMKjM ➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

This episode is an eye-opening case study where Jaryd Krause sits down with AJ, a Buying Online Businesses graduate who made the leap from running a large IT team at a global bank to building an online business portfolio. AJ shares how he went from launching a failing startup to successfully acquiring a $50,000 media and membership business that now generates $2,000 net profit per month—all within just six months. Inside this conversation, you’ll know: ✔️ Why AJ abandoned the startup path in favor of buying an existing business✔️ The exact business model he chose—and why it stood out among the rest✔️ How he saved money on the acquisition price (including what multiple he actually paid)✔️ The due diligence steps he took to minimize risk before signing the deal✔️ The hardest part of buying a business (his answer may surprise you)✔️ His best advice for first-time buyers—and what’s next as he builds his portfolio Packed with lessons from someone who’s navigated the challenges and emerged profitable, this episode is a must-listen whether you’re planning your first business acquisition or aiming to master your due diligence process 🎧 Tune in to learn how AJ turned a $50K deal into a reliable income stream—and how you can apply the same strategies to your own acquisition journey.   Episode Highlights 09:47 – Llearning how to properly evaluate businesses instead of jumping straight into a deal. 13:38 – Defining non-negotiables: valuing time, lifestyle, and family more than owning a “sweet deal.” 18:22 – How looking at hundreds of businesses sharpened AJ’s ability to spot red flags and opportunities. 21:14 – There are no unicorns—every business has cons; it’s about choosing what risks you can manage. 26:55 – Why the decision to “pull the trigger” is the hardest part of the acquisition journey. 35:52 – Advice for first-time buyers: don’t skip the learning stage—education reduces fear and regret. 41:55 – The difference between being a business operator and becoming a true owner with leverage. Key Takeaways ➥ There’s no such thing as a perfect business. Every deal has risks; the key is knowing which ones you can live with and mitigate. ➥ Start with education. Skipping the learning phase leads to regret; preparation makes the acquisition less scary and more strategic. ➥ Taking the leap is the hardest part. Eventually you must stop analyzing and trust your due diligence to move forward. ➥ Aim to work on the business, not in it. Leveraging teams and managers turns you from operator into true owner. ➥ Bigger opportunities become realistic after the first acquisition. The initial win builds confidence to pursue larger, even debt-financed, deals. About AJ AJ is a BuyingOnlineBusinesses.com graduate who went from being a corporate employee running a large IT team for a global bank. To now an online business owner and building a portfolio of businesses.    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Hostinger (Website Hosting) - https://bit.ly/3HUqW0s ➥ Rank Math (Wordpress SEO Plugin) - https://bit.ly/3Acyjf4 ➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

In this power-packed episode, Jaryd Krause sits down with serial founder and dealmaker Anthony Franco, a man who knows exits inside and out. Having built and sold seven companies—six of them successfully, including two to publicly listed firms—Anthony brings rare, battle-tested wisdom to the table. Together, they dig into what it really takes to engineer a successful exit in the $5M–$50M range. From preparing your business to maximize valuation, to structuring deals that minimize risk for both buyers and sellers, Anthony shares the strategies he’s used to navigate countless transactions. He doesn’t sugarcoat it either—every deal has “hair” on it, and this conversation unpacks exactly how to handle those messy, unexpected challenges that can tank a deal if you’re not prepared. You’ll learn:✔️ How to structure an exit so you walk away with more security and better terms✔️ Why taking your foot off the gas before closing can destroy your valuation✔️ How buyers can avoid catastrophic mistakes by spotting risk early✔️ What makes a business truly attractive to both strategic and financial buyers✔️ The evolving role of AI in business growth, exits, and even the future of work Whether you’re eyeing a future sale, planning to acquire, or just want to build a business that’s more valuable and resilient, this episode is a masterclass in deal-making straight from someone who’s been through it all. 🎧 Tune in now to hear how to prepare, structure, and execute smarter exits.   Episode Highlights 04:50 – Clean books, systems, and reduced key-person dependency: the essentials for any exit. 06:50 – Why every exit is messy—buyers always renegotiate during LOI. 08:30 – Sophisticated vs. inexperienced buyers: how the right questions signal experience. 09:35 – Knowing what really matters in due diligence vs. what’s just “wonky” small-business noise. 11:20 – Why trust and fairness between buyer and seller are critical when numbers vary near close. 12:50 – Sellers must keep operating like they won’t exit—taking the foot off the gas can kill deals. 18:00 – Why tax planning is just as important as negotiating the sale price. 25:40 – Selling fast matters—waiting too long risks copycat competitors and valuation drops. 27:40 – Regulation, trucking, and AI adoption: why safety perception, not data, drives adoption speed.   Key Takeaways ➥ Prepare early. Clean financials, diversified revenue streams, and reduced key-person dependency are critical to maximizing valuation. ➥ Buyers are risk-averse. Expect tough questions in due diligence—not personal attacks. Sophisticated buyers ask the right way, but all buyers are trying to mitigate risk. ➥ Deal structures matter. Cash is king for sellers. Earn-outs, seller notes, and rollover equity all come with risks—align them with your personal life stage and goals. ➥ Don’t take your foot off the gas. Deals can drag on for months. Keep running your business as though it won’t sell; growth during due diligence strengthens your negotiating power. ➥ Surround yourself with the right advisors. A good CPA and financial advisor can save millions in taxes and structure your exit properly. ➥ AI is changing the game. It will automate “crappy work,” commoditize parts of business, and put greater emphasis on distribution, brand, and audience trust. ➥ Faster is better. Once you decide to sell, speed matters—because markets and competitors don’t wait.   About Anthony Franco Anthony Franco is a seasoned founder, operator, and dealmaker who’s built and sold seven companies—six of them successfully, including two to publicly listed firms.  After working closely with the team at OneReach.ai, he realized traditional frameworks like Lean and Agile just don’t cut it in today’s fast-moving, AI-driven world. That insight led to the creation of the WISER Method—a new approach that helps founders build smarter, scale faster, and exit more strategically. He’s also a licensed business broker, and on his own podcast How to Founder, he shares real-world strategies for building businesses that are easier to operate and more valuable to sell. Connect with Anthony Franco ➥ https://www.linkedin.com/in/anthonyfranco/ ➥ https://www.aifirstprinciples.org/ Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Cloud Ways (Website Hosting) - https://bit.ly/40tjyjG ➥ SEM Rush (SEO tool) - https://bit.ly/3lINGaV ➥ Ezoi

In this raw and eye-opening episode, Jaryd Krause chats with Matthew Tse—a former Big Tech software engineer who ditched the corporate grind to buy his way into freedom through online business. Today, he runs ImprovMX.com, a SaaS business he acquired after sifting through countless deals, failed startup attempts, and plenty of trial and error. Matthew doesn’t sugarcoat it. He shares the highs, the mistakes, and the exact process that helped him land the right acquisition to replace his income and build a life on his own terms. In this no-BS conversation, you’ll discover: ✔️ How many businesses do you really need to analyze before finding “the one”✔️ The critical mindset shifts that help you push through failed deals and land a winner✔️ Why chasing small, cheap businesses can actually cost you more in the long run✔️ The price range Matthew now recommends for friends looking to buy online✔️ His top growth levers for scaling SaaS—starting with retention before expansion If you’ve ever wondered how long it actually takes to buy an online business—or what it feels like to transition from employee to owner—this episode pulls back the curtain on the entire journey. 🎧 Tune in now and learn what it really takes to replace your income with a SaaS acquisition.   Episode Highlights 09:21 – Learning from others’ success can inspire acquiring an existing business instead of starting from scratch. 14:16  – Defining an ideal business model and price range narrows the search effectively. 17:11 – Focusing on businesses aligned with personal strengths leads to better outcomes than chasing every opportunity. 20:35 – Studying case studies and industry insights accelerates learning and reduces mistakes. 26:37 – Audience trust and built-in channels are more valuable than the product itself. 43:20 – Avoiding small deals and aligning acquisitions with lifestyle and skills improves success. 47:38 – Buying the right SaaS can replace traditional income while leveraging personal strengths effectively.   Key Takeaways ➥ Acquisitions can accelerate entrepreneurship—buying an existing business allows leveraging capital and skills to bypass the hardest startup challenges. ➥ Understanding your strengths and weaknesses is essential to narrowing search criteria and finding the right business model and price range. ➥ True value lies in the audience, reputation, and established distribution channels—not just the product or code. ➥ Preparation and research, including learning from others’ experiences and industry content, reduce risk and improve outcomes. ➥ Mindset, persistence, and patience are critical when evaluating hundreds of businesses to find the right fit. ➥ Post-acquisition growth is most effective when leveraging existing channels, retention strategies, and organic traffic. ➥ Being selective and strategic—rather than opportunistic—ensures acquisitions provide both ROI and lifestyle freedom.   About Matthew Tse Matthew Tse was a career software engineer in big tech & quant finance. He decided he wanted a more free & fulfilling life, and eventually stumbled his way into acquiring improvmx.com, which he's now running and growing.   Connect with Matthew Tse ➥https://www.linkedin.com/in/matthew-t-15565736/ ➥matthewtse.com ➥https://buyingonlinebusinesses.com/ep-212-how-to-start-buying-flipping-small-saas-businesses-with-andrew-pierno/   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ GoDaddy (Website Hosting) - https://bit.ly/3YiRkWV ➥ Rank Math (WordPress SEO Plugin) - https://bit.ly/3Acyjf4 ➥ Active Campaign (Email Software Provider) - https://bit.ly/3DCwYQH   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

In this sharp and savvy episode, host Jaryd Krause welcomes M&A heavyweight Michael Vann—President of the Vann Group and Principal at Eaton Square—for a deep dive into the brilliant… and brutally expensive mistakes entrepreneurs make when trying to grow through acquisition. With 25+ years of deal-making, scaling, and succession planning, Michael’s been in the trenches guiding businesses to multi-million dollar exits across industries from manufacturing to online empires. He’s seen it all—and he’s here to share what not to do when chasing growth. Spoiler: Buying three businesses in six months with zero integration strategy? That’s not scaling. That’s self-sabotage. In this no-fluff convo, you’ll learn: ✔️ The explosive difference between a strategic buyer and a chaotic cowboy ✔️ Why some acquisitions implode and drain value instead of adding it ✔️ How to prep your current business to absorb acquisitions without blowing it up ✔️ The secret to thinking beyond the buy—to integration and exit strategy ✔️ How to build a business so irresistible that even your competitors want to buy it If you’ve ever thought, “Maybe I’ll just buy another business and double my revenue,” you need to hear this. 🎧 Tune in now to learn how to grow through acquisition… without blowing up your business in the process.   Episode Highlights 06:30 – The importance of understanding the buyer’s mindset, especially when preparing to exit your business. 08:45 – Common reasons businesses fail to sell — including overvaluation, poor documentation, and lack of transferable leadership. 11:20 – Why “deal fever” can cloud entrepreneurs’ judgment and lead to bad acquisitions. 14:10 – Cultural fit and leadership alignment: often the real reasons integrations fail after a deal. 22:50 – Lessons learned from failed deals and red flags to look out for before signing. 26:30 – Strategic vs. opportunistic acquisitions — why clarity in intent is key. 28:45 – How to prepare your business for exit years in advance, including systemization and leadership planning.   Key Takeaways ➥ Being selective is critical—just because an opportunity arises doesn’t mean it’s the right fit for your business or your life. ➥ The buyer’s perspective matters—sellers must see their business through the lens of the acquirer: is it transferable? sustainable? well-documented? ➥ Leadership and culture are make-or-break factors in post-acquisition integration. Without the right leadership in place, the acquired business often struggles. ➥ Deal fever is real—don’t let excitement override discipline. Stick to your acquisition criteria and due diligence process. ➥ Exiting a business is a long game—the most successful exits come from those who plan years, building systems and leadership teams that can thrive without the founder. ➥ Avoiding mistakes means preparation, patience, and perspective—take your time, ask the right questions, and align your acquisitions with long-term strategy.   About Michael Vann Michael Vann is the President of The Vann Group, a family-owned firm that provides strategic consulting and transactional advisory services to privately held businesses. With over 25 years of experience, Michael helps owners scale, plan for succession, and maximize value. He’s also a principal at Eaton Square, a global investment banking firm, and a certified Predictable Success Scale Architect. Michael has advised on deals up to $50 million across industries like manufacturing, services, construction, and hospitality. He’s the co-author of Buying Out the Boss and the forthcoming High Performing Value, and frequently speaks on value building and business transitions. Michael lives in South Hadley, Massachusetts, with his wife, two daughters, and one unruly pup.   Connect with Michael Vann ➥https://www.linkedin.com/in/michaelvann/  ➥www.vann-group.com   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Cloud Ways (Website Hosting) - https://bit.ly/40tjyjG ➥ SEM Rush (SEO tool) - https://bit.ly/3lINGaV ➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when yo

Exiting a business can be one of the most rewarding moments of an entrepreneur’s journey—or one of the most costly mistakes if handled poorly. Many sellers unknowingly leave hundreds of thousands, even millions of dollars, on the table simply because they aren’t prepared for the exit process. Jaryd Krause speaks with Domenic Rinaldi, a seasoned M&A advisor and owner of Sun Acquisitions, who has successfully guided over 500 business transactions. As the founder of K2 Advisor, Domenic specializes in helping business owners understand exactly what it takes to execute a profitable and stress-free exit. Together, they break down the biggest mistakes sellers make when exiting their businesses and how to avoid them.  You’ll discover: ✔️ How owner involvement and single-source dependencies can destroy your business valuation ✔️ Why many sellers are blindsided by market shifts, tariffs, and environmental changes ✔️ The critical role of value drivers and how to identify them before going to market ✔️ What can go catastrophically wrong during a deal—and how the right advisory team can prevent it ✔️ Why you should always be “exit ready,” even if selling isn’t on your immediate horizon If you’re preparing to sell your business—or simply want to protect the value you’ve built—this episode is packed with actionable insights to help you exit on top. 🎧 Listen now and learn how to exit your business the smart way. Episode Highlights 02:18 – Why most sellers leave money on the table when exiting their business 05:42 – How owner dependence and single-source revenue can destroy valuation 08:15 – Common risks in the current market, including tariffs and environmental changes 11:35 – Value drivers Domenic looks for when assessing a business for sale 14:50 – The importance of due diligence and how small oversights can become costly 17:30 – Why sellers must always be “exit-ready,” even if they’re not planning to sell soon 20:10 – Choosing the right advisory team: lawyers, accountants, and M&A experts who can make or break your exit Key Takeaways ➥ Seller mistakes are costly. Failing to prepare for an exit can result in leaving hundreds of thousands—or even millions—of dollars on the table. ➥ Owner dependency kills value. Businesses overly reliant on the owner, single customers, or single traffic sources are heavily discounted by buyers. ➥ Market conditions matter. External factors like tariffs, environmental shifts, or regulatory changes can impact valuation. Smart sellers plan for these contingencies in advance. ➥ Value drivers determine your sale price. Revenue diversity, strong cash flow, and documented systems all increase buyer confidence and the multiple you can command. ➥ Due diligence is non-negotiable. Small errors or overlooked liabilities can derail a deal. A proactive approach prevents last-minute surprises. ➥ Always be exit-ready. Even if you’re not planning to sell, setting up your business for a smooth exit ensures you’re prepared for unexpected life events or market opportunities. ➥ The right team is critical. Experienced lawyers, accountants, and M&A advisors can prevent deal disasters and protect your financial outcome.   About Domenic Rinaldi A seasoned M&A adviser, Domenic Rinaldi is the Owner and Managing Partner of the firm, Sun Acquisitions. He also founded K2Adviser to educate business owners on the requirements for a successful exit, acquisition, or scaling process.     Connect with Domenic Rinaldi ➥https://buyingonlinebusinesses.com/ep-087-why-you-need-seasoned-vets-on-your-team-when-buying-selling-businesses/ ➥www.sunacquisitions.com   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ GoDaddy (Website Hosting) - https://bit.ly/3YiRkWV ➥ Non Agency (SEO Audit) - https://bit.ly/3EPd7OZ ➥ Market Muse (Content Marketing Software) - https://bit.ly/3Me39L0   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Running a business is about building something that works without you, not just putting in the hours. But far too many entrepreneurs stay stuck in the weeds, overwhelmed by daily tasks and unclear on how to truly scale. That’s where systems—and now, AI—change everything. In this conversation, Jaryd Krause is joined by David Jenyns, founder of Systemology and author of SYSTEMology and The Systems Champion, to unpack how smart systems combined with the power of AI are transforming the way online businesses grow. David has built and sold multiple companies, helped hundreds of business owners systemize their operations, and now leads the conversation on how AI can be used not just to support teams, but to replace certain roles altogether. You’ll learn: ✔️ How to use AI to build and improve systems in your business✔️ Why experienced talent plus AI is replacing the traditional VA model✔️ How to step back from your business without losing momentum✔️ Real-life examples of AI replacing inefficiencies and boosting profits When it comes to growing your business, reclaiming your time, and creating something that endures, this episode is packed with useful strategies and steps to follow. 🎧 Tune in now and learn how to scale smarter with the systems + AI advantage.   Episode Highlights 01:44 – Why systemizing your business is critical for growth and freedom 06:15 – How to commit fully and overcome resistance when building systems 12:30 – The role and impact of a systems champion in scaling your business 19:30 – Where a systems champion fits in and how to identify the right person 22:00 – The transformative power of AI in systemizing processes and operations 27:30 – Real-life example of AI disrupting traditional business documentation 32:00 – How AI enhances the productivity of skilled team members and shrinks teams 35:00 – Using AI strategically to outperform competitors and grow faster   Key Takeaways ➥ Committing fully to systemizing your business culture is essential; half-measures lead to failure due to team resistance. ➥ Hiring a systems champion is critical—they drive the systemization process and embed a culture of repeatability and efficiency. ➥ Business owners need to shift focus from daily tasks to strategic growth, enabled by well-documented systems and strong teams. ➥ AI tools like ChatGPT and Google Gemini accelerate system documentation, process optimization, and strategic decision-making. ➥ AI adoption leads to smaller, more skilled teams who leverage technology to produce higher-quality results. ➥ Privacy concerns around AI data use require careful selection of secure platforms to protect business information. ➥ The systems champion role is evolving to include AI management, programming workflows, and ensuring the accuracy of AI outputs. ➥ Businesses embracing AI and systems now will stay competitive; those who resist risk falling behind in a rapidly changing landscape.   About David Jenyns David Jenyns is an experienced entrepreneur who sold the Melbourne Cricket Ground in his early twenties and founded Melbourne SEO Services. He systematized himself out of that business in 2016 and founded SYSTEMology to help business owners implement systems to scale their business. Today, he supports a growing community of certified SYSTEMologists, delivers workshops, keynote addresses hosts a podcast, and is on a mission to free business owners worldwide from daily operations.    Connect with David Jenyns ➥ https://www.systemology.com/scbook/ ➥ https://www.systemology.com/   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Rank Math (Wordpress SEO Plugin) - https://bit.ly/3Acyjf4 ➥ Convert Kit  (Email Service Provider) - https://bit.ly/3o10Xgx   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Understanding the fine print that could make or break your deal is just as important when purchasing a business with SBA financing as it is when obtaining a loan. All too frequently, buyers lose out on opportunities or become mired in transactions that don't fit the program because they are unaware of the nuances of SBA regulations. The CEO of SBA Loan Group, Yankie Markowitz, sits down with Jaryd Krause in this episode to discuss his extensive knowledge of SBA loans and how he has facilitated more than $1 billion in SBA and real estate transactions. Yankie explains which business categories are eligible for SBA financing, what has changed recently, and how to handle the complex world of debt ratios, deal structures, and cash requirements. You’ll learn: ✔️ Which businesses can—and can’t—be acquired with SBA loans ✔️ How much cash do you need to qualify ✔️ Why e-commerce fits well with SBA financing, and where it falls short ✔️ The ins and outs of seller notes, holdbacks, and loan terms ✔️ Real-world lessons from deals that worked—and ones that didn’t This episode provides useful, straightforward advice from one of the most seasoned SBA specialists in the industry, regardless of whether you're prepared to purchase your first company or want to improve your acquisition approach. 🎧 To learn how to make SBA financing work for you and get closer to financial independence, listen now.   Episode Highlights 06:15 – Eligibility requirements and the role of creditworthiness in SBA loan approval 10:30 – Structuring deposits and how larger down payments can secure better interest rates 15:45 – Differences in loan terms and amortization for business vs. real estate purchases 20:20 – Prepayment penalties and their impact on SBA loan flexibility 23:00 – Utilizing seller notes and financing strategies in SBA deals 29:50 – Debt service coverage ratios and the importance of consistent cash flow Key Takeaways ➥ SBA financing is highly versatile, supporting working capital, inventory, real estate, and refinancing, but buyers must understand eligibility and lender-specific nuances. ➥ Seller financing (seller notes) can be incorporated into SBA deals but requires careful structuring to meet lender requirements and ensure adequate cash flow. ➥ Business valuation multiples generally range from 3-5x EBITDA for traditional businesses; higher multiples (like software businesses) often require substantially more equity upfront. ➥ Owning an existing profitable business simplifies acquiring complementary businesses by leveraging combined cash flow to support additional debt. ➥ Sustainable growth beats rapid expansion; business owners must carefully manage operational costs and cash flow to avoid overextension post-acquisition.   About Yankie Markowitz Yankie Markowitz is the Chief Executive Officer of SBA Loan Group. Yankie has helped facilitate over $1 billion dollars in SBA and real estate transactions, and complex deal syndication. He is often sought out by bankers to help structure intricate SBA transactions because of his knowledge and unique experience with the U.S. Small Business Administration loan programs.  Yankie is an Executive Board member for the Regional Business Assistance Corporation (an SBA CDC) and has been on the Loan Committee which allows him to work on hundreds of transactions for SBA each year. He also serves as a Board Member of Crown Heights Young Entrepreneur, a non-profit that is a full-service business resource center specifically tailored to fit the unique needs for aspiring entrepreneurs that focus on promoting responsible business development and providing them with the tools and resources that they need in order to achieve lifelong financial independence.    Connect with Yankie Markowitz ➥ https://sbaloangroup.com/ ➥https://finwise.podbean.com/e/finwise-eye-on-sba-lending-yankie-markowitz-ceo-sba-loan-group/   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Hostinger (Website Hosting) - https://bit.ly/3HUqW0s ➥ Rank Math (Wordpress SEO Plugin) - https://bit.ly/3Acyjf4 ➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P 🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy inform

Buying or selling a business isn’t just a transaction — it’s a turning point. But too often, what buyers think they want and what sellers believe they deserve don’t line up with reality. The result? Stalled deals, missed opportunities, and plenty of frustration on both sides. In this episode, Jaryd Krause sits down with Matt Frisca, owner of Transworld Business Advisors of La Grange and Tinley Park, to unpack the biggest reasons deals fail—and what it really takes to make them work. With 20+ business sales closed annually and 50+ active listings, Matt shares real-world insights from both sides of the table. You’ll learn: ✔️ Why sellers struggle to exit cleanly✔️ Common mistakes buyers make (and how to avoid them)✔️ The truth about SBA financing and “no money down” deals✔️ What due diligence really looks like in today’s market Whether you're buying, selling, or just curious, this episode delivers raw advice and actionable strategies from a dealmaker who knows the game. 🎧 Listen now and get the inside track on what actually moves the needle in business acquisitions.   Episode Highlights 12:40 – Importance of motivated sellers and avoiding lead oversaturation 15:45 – The three biggest reasons businesses fail to sell: lack of motivation, messy financials, and unrealistic pricing 19:30 – Recent SBA lending rule changes and fees 22:45 – Why “no money down” deals are unrealistic 24:40 – Risks of inexperienced buyers buying big businesses 28:10 – How to be an attractive, prepared buyer 33:15 – Balancing due diligence and trust to avoid “paralysis by analysis”   Key Takeaways ➥ Motivated sellers, clean financials, and realistic prices are crucial.➥ Content marketing is replacing paid ads due to cost hikes.➥ Seller equity rollovers now carry higher risk for sellers.➥ “No money down” deals rarely work; buyers need funds and experience.➥ Private equity adds competition for deals under $5M.➥ Prepared buyers with financing and clear plans succeed more.➥ Avoid overanalyzing—take calculated risks to close deals.   About Matt Frisca Matt Friscia runs and owns the Transworld Business Advisors of La Grange and Tinley Park with his team of 9 agents and one administrative assistant, focusing on main street and lower mid-market business brokerage. Their office handles over 20 successful closes a year, and they typically are working 50+ business for sale listings at any given time. Before joining Transworld, Matt worked in media sales for 15 years. Ten of those years were with the Disney company within their ESPN, ABC, and Radio Disney brands. He bought his first business, which was a franchise in the senior care field, back in 2016. He successfully grew that company and ultimately sold it five years later with Transworld Business Advisors.  His passion is helping small business owners with their business exit transactions while helping to super serve the underserved community of small businesses. Besides having played music professionally for the past 28 years, he enjoys watching his two children play sports, traveling and learning languages.   Connect with Matt Frisca ➥ https://www.tworld.com/    Resource Links ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Cloud Ways (Website Hosting) - https://bit.ly/40tjyjG ➥ Link Whisper (SEO tool for internal linking on websites) - https://bit.ly/3l7K7Ld ➥ Convert Kit (Email Software Provider) - https://bit.ly/3o10Xgx   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Let’s be real — buying or selling a business is one of the biggest decisions you’ll ever make. Get it right, and it could be life-changing. Get it wrong… and the fallout could be brutal. That’s exactly why this week’s episode is a must-listen. Jaryd Krause sits down with Katarina Strandberg, a powerhouse Swedish business lawyer with deep expertise in venture capital, scale-ups, and M&A. She’s worked with founders, investors, and SME leaders across Europe, and brings not only legal chops but also perspective as an angel investor, published author, and university lecturer. Katarina has seen it all — and she’s here to share the real stories, the hard truths, and the clever strategies that can make or break your deal. In this episode, you’ll learn: ✔️ The biggest risks buyers face (and how to avoid stepping on legal landmines)✔️ What really happens during legal due diligence — and why it’s more than just paperwork✔️ How to deal with “deal fatigue” and who should keep cool when emotions run high✔️ Jaw-dropping stories of deals gone wrong — and the legal moves that could’ve saved them✔️ Clever deal structures and funding options that most people never think about✔️ How to avoid surprise legal bills (yes, it’s possible!)✔️ Why skipping legal help might be the most expensive mistake you ever make If you’ve ever felt overwhelmed by contracts, confused by due diligence, or just unsure about when to bring a lawyer in, this episode is your roadmap. 🎧 Tune in now and learn how to protect yourself, your deal, and your financial future — with smart legal strategy by your side.     Episode Highlights 02:50 – Why defining “online” vs “physical” businesses is crucial for strategy and contracts 07:10 – Ignoring a “change of control” clause led one buyer to lose supplier exclusivity overnight 08:15 – How proper due diligence helps uncover risks, negotiate price, and add protections 16:50 – Why non-compete agreements are critical to prevent the seller from becoming your competitor 21:40 – Managing emotions, trust, and “deal fatigue” is key to getting deals across the line 25:45 – Fixed legal fees and clear timelines reduce stress and prevent buyer fatigue 28:20 – Preparing buyers early for delays and emotional hurdles ensures smoother transactions   Key Takeaways ➥ Overlooking contract clauses (like change of control) can destroy business value overnight ➥ Buyers must normalize financials to reflect realistic salaries, working capital, and operational needs ➥ Strong non-compete agreements are non-negotiable to protect your investment ➥ Managing trust and emotions during diligence is just as important as the numbers ➥ Fixed-fee legal services and clear expectations help avoid surprises and fatigue ➥ Every deal involves risk — great advisors help you identify, price, and mitigate those risks effectively   About Katarina Strandberg Katarina Strandberg is a Swedish business lawyer specializing in venture capital, scale-ups, and M&A. She advises SME leaders and investors, drawing on her experience in deal structuring, fund law, and legislative work. A published author and angel investor, she’s also taught at Swedish universities and served on international advisory boards.   Connect with Katarina Strandberg ➥ https://www.youtube.com/@Businesslawtoolbox ➥https://www.stgcommerciallaw.com/    Resource Links ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Link Whisper (SEO tool for internal linking on websites) - https://bit.ly/3l7K7Ld ➥ Active Campaign (Email Software Provider) - https://bit.ly/3DCwYQH   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR     *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Strap in for a brutally honest conversation as Jaryd Krause sits down with none other than Elliot Holland,  a Harvard Business School alum, seasoned entrepreneur, and strategic founder. Elliot runs a seven-figure due diligence firm that performs "mini audits" on businesses, helping investors avoid being misled by clever sellers and slick brokers. With nearly 20 years of experience in small business acquisitions, Elliot has seen it all—and then some. From hidden red flags in financials to smoke-and-mirrors marketing metrics on Amazon and SEO-driven sites, he shares exactly where buyers get it wrong—and how those mistakes can cost you hundreds of thousands, or worse, your entire investment. This episode will pull back the curtain on how unsuspecting buyers get swindled into buying dud deals, all because they skipped real due diligence. Highlight the critical considerations buyers often miss in the acquisition process: ✔️ The most common (and costly) mistakes buyers make in due diligence✔️ Why relationships with sellers matter—and how they can go sideways fast✔️ How sellers can mislead or manipulate the narrative to close a deal✔️ Financial vs. marketing due diligence—what most acquirers overlook✔️ The frameworks Elliot uses to assess businesses like an expert This is not just theory—Elliot has personally helped countless clients dodge bad deals and secure multi-million-dollar wins, all by demystifying the due diligence process. With his signature humor, straight talk, and lived experience, he makes complex business buying principles not only clear but actionable. Whether you're a first-time acquirer or scaling your portfolio, this episode will save you more than money—it could save your sanity. Don’t even think about buying a business until you listen to this conversation.    Episode Highlights 04:15 – Red flags usually show as many small issues rather than one big problem 10:30 – Verifying seller’s time commitment by reviewing task lists and holding strategy meetings 18:45 – Wanting shortcuts in due diligence can lead to costly mistakes 23:00 – Sellers often resist reasonable buyer requests like strong non-competes and management interviews 26:10 – Negotiation is a strategic dance where sellers test buyer strength 29:15 – Cheaper advisors often bring higher risks and lower value on seven-figure deals   Key Takeaways ➥ Red flags are subtle and require a sharp, skeptical mindset to detect ➥ Sellers use stories and distractions instead of admitting flaws outright ➥ Due diligence takes time and can be uncomfortable but shortcuts are costly ➥ Experienced advisors are critical for high-value deals to avoid disaster ➥ Buyers need to be ready to walk away if sellers are not transparent or cooperative ➥ Emotional detachment helps buyers make better decisions and negotiate smarter   About Elliot Holland Elliott Holland is a Harvard Business School alum, former business acquirer & OG in small business acquisitions.  He runs TheBusinessBuyingMasterclass.com and a 7-figure business that does "mini audits" on businesses before clients acquire them to be sure they're not swindled.  With nearly two decades of experience, Elliott empowers everyday investors to acquire million-dollar businesses because he's been in their shoes and offers insight others cannot.   Elliott simplifies complex small business buying concepts with humor so that everyday investors can understand.   With over 100 podcast appearances and speaking engagements at top business schools, Elliott shares expertise on entrepreneurship, investing, and business buying.   Connect with Elliot Holland ➥ https://www.linkedin.com/in/elliottholland/   Resource Links ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Link Whisper (SEO tool for internal linking on websites) - https://bit.ly/3l7K7Ld ➥ Active Campaign (Email Software Provider) - https://bit.ly/3DCwYQH 🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

In this compelling episode, Jaryd Krause is joined by seasoned dealmaker and legal expert Jerome Fogel, partner at Fogel & Potamianos LLP, a boutique law firm specializing in high-stakes mergers, acquisitions, and capital raises. With a client list that spans venture funds, emerging tech companies, and elite athletes, Jerome offers a rare behind-the-scenes look at what it takes to structure smart, safe, and scalable business deals. Unpack the most critical questions aspiring buyers need to ask before acquiring an online business: ✔️ What are the hidden risks in buying or selling?✔️ How can poor team dynamics tank a deal?✔️ Should you use financing to buy a business—and what’s the best way to structure it?✔️ Where are the most promising online businesses being acquired today? Dive deep into the importance of due diligence, the common pitfalls buyers fall into, and how Jerome has helped high-profile clients—both on Wall Street and in the sports world—navigate complex transactions and build generational wealth. Whether you're looking to buy your first online business, scale your portfolio, or just want a masterclass in deal-making from someone who lives and breathes it, this episode delivers powerful insights and practical strategies. Don’t miss this one—it’s packed with value from start to finish.   Episode Highlights 04:45 – Current valuations explained, covering how tariffs and supply chain issues impact multiples and buyer decisions. 07:20 –  Typical ways buyers finance acquisitions, including credit lines, SBA loans, equity rollovers, and search funds. 10:55 – Major mistake buyers make by rushing post-acquisition integration without building trust within the team. 12:45 – What successful acquisitions have in common by retaining key team members and valuing the founder’s knowledge. 24:10 – Key risk prevention strategies involving thorough reps and warranties, clear earnout terms, strong IP protections, and precise legal language. 26:30 – Why clear definitions around risk and performance clauses are vital.   Key Takeaways ➥ M&A valuations currently range from 3–8x EBITDA for traditional companies and 10–15x for platform tech businesses, influenced heavily by tariffs and market uncertainty. ➥ Buyers typically operate in the $2M to $25M+ EBITDA range and rely on strong banking relationships, SBA loans, or creative financing like equity rollovers. ➥ Structuring deal terms clearly—especially reps and warranties and material adverse effect clauses—is critical to managing risk in acquisitions. ➥ Post-acquisition integration is one of the toughest challenges; involving existing teams and respecting founders’ knowledge leads to smoother transitions. ➥ Restrictive covenants are essential to prevent sellers from competing after the sale and protect buyer investments. ➥ Every deal is unique and requires customized, creative solutions; cookie-cutter approaches don’t work in M&A.   About Jerome Fogel Jerome Fogel is known as a dealmaker and innovator in the legal community. He is a partner with Fogel & Potamianos LLP and represents successful venture and hedge funds, corporations, and sports superstars.Fogel & Potamianos LLP is a boutique transactional firm that provides sophisticated counsel for buy-and-sell side mergers and acquisitions, fund formation, capital raises, and off-field sports transactions.Jerome has a 360-degree view of dealmaking, as he represents emerging companies raising capital, venture funds deploying capital, advisors and investors, and private companies in mergers and acquisitions.Jerome began his career in real estate finance at GE Capital. He is a graduate of the Haas School of Business (BS) and New York University School of Law (JD).   Connect with Jerome Fogel ➥ https://www.linkedin.com/in/jeromefogel/ ➥ www.fpgeneralcounsel.com   Resource Links ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Link Whisper (SEO tool for internal linking on websites) - https://bit.ly/3l7K7Ld ➥ Active Campaign (Email Software Provider) - https://bit.ly/3DCwYQH   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cos

What if you could skip the struggle of starting a business from scratch—and step straight into profit? In this solo episode, Jaryd Krause pulls back the curtain on everything you need to know before buying your first (or next) profitable online business. No guest this time—just Jaryd, and over ten years of real-world experience helping thousands of people build financial freedom through smart acquisitions. This episode is a deep dive inspired by Jaryd’s most-watched YouTube content and the questions he hears constantly from aspiring buyers: Why should you buy a profitable business? How much should you invest? Should you use your cash or finance the deal? And where are people buying these businesses today? Get ready for a no-fluff breakdown of: ✔️ Why buying a profitable online business can fast-track your path to income and freedom✔️ How much capital do you need to get started (spoiler: it’s not always as much as you think)✔️ The truth about financing a deal—and what creative structures work✔️ Where to find legitimate, vetted businesses for sale right now✔️ The rookie mistakes that could cost you thousands—and how to avoid them This isn’t financial advice—but it is packed with insights from someone who’s helped people go from browsing listings to building six- and seven-figure digital business portfolios. If you’re ready to move from dreaming to doing, this episode will show you exactly what to consider, what to avoid, and where the real opportunities are in 2025’s online business marketplace. Hit play and take notes—this one’s loaded.   Episode Highlights 04:17 – Why buying a profitable online business is better than starting one from scratch? 07:38 – The ideal type of online business to acquire as a beginner. 13:24 – How much money should you invest when buying your first business? 18:43 – Why must you understand the ROI beyond just net profit? 27:46 – Myths around no-money-down deals and what real financing looks like. 31:22 – Where to find online businesses for sale: brokers vs. off-market deals?   Key Takeaways ➥ Buying an existing online business is less risky and faster than starting fresh, as you inherit proven systems, traffic, and revenue, reducing trial and error. ➥ “No money down” deals are rare and mostly involve distressed or declining businesses; most require some cash upfront. ➥ Acquisitions usually need a mix of cash, lender, and seller financing, with 10-20% cash upfront to show commitment. ➥ Reliable marketplaces like Empire Flippers, Quiet Light, and Flippa are great starting points for sourcing online businesses. ➥ Sellers often move on not because their business is failing but because of personal reasons like boredom or lifestyle changes, emphasizing the importance of proper due diligence before buying.   Connect with Jaryd Krause ➥https://www.linkedin.com/in/jarydkrause  ➥ $240K Income When Buying An Online Business - https://www.youtube.com/watch?v=G3yja-KnZzA&t=105s ➥Why Size Matters When Buying An Online Business - https://www.youtube.com/watch?v=7OWdl_n9rZI   Resource Links ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Hostinger (Website Hosting) - https://bit.ly/3HUqW0s ➥ SEM Rush (SEO tool) - https://bit.ly/3lINGaV ➥ Convert Kit (Email Software Provider) - https://bit.ly/3o10Xgx 🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Buckle up for an eye-opening episode where Jaryd Krause is joined by powerhouse entrepreneur and investor Justin Williams—a man who’s navigated everything from crippling six-figure debt to building and selling a multimillion-dollar business. Justin’s journey is far from ordinary. After dropping out of college, he and his wife, Tara, left their careers to pursue financial freedom. Their first business left them $120,000 in debt, living in a shared house with a newborn. Instead of quitting, they shifted to real estate, flipping over 100 houses a year and launching House Flipping HQ, a real estate education company that helped thousands succeed. Justin revealed how he sold his real estate education business for over $3.5 million—covering the why, when, and how. They dive into the unconventional yet strategic deal structure when selling to an operator already in the business. Then he delved into wealth building through business and real estate. Justin explains if he’d buy an online business, how he’d finance it, and the math behind buying a $2M business, hiring an operator, and earning $300K net profit annually without running it himself.   Gain insights on: ✔️ When is the right time to sell your business?✔️ The differences between investing in real estate vs. digital businesses✔️ How to build sustainable wealth without burning out✔️ And most powerfully—how Justin got through the lowest points of his journey. If you're looking for real talk about business, money, mindset, and freedom, this is the episode for you. Don’t miss this raw, high-energy conversation that’s packed with strategy, real numbers, and heart. Whether you're planning your first acquisition, prepping for a sale, or just needing motivation to keep pushing, this one will hit home.   Episode Highlights 03:00 – The journey to selling a $3.5M+ online business and lessons learned 08:20 – Using SBA loans to buy businesses vs. buying without them – pros, cons, and examples 10:50 – Buying businesses you don’t operate: how Justin makes it work and what to look for 17:35 – How Justin handled $120K in debt and overcame early financial struggles 23:40 – Managing expectations: The reality behind case studies and quick success stories 28:20 – Balancing ambition with lifestyle: Prioritizing family, health, and business growth 38:50 – Building habits and mentality for consistent progress versus just grinding Key Takeaways ➥ Everyone’s journey is different—don’t let case studies make you feel behind. ➥ Selling his $3.5M business was a strategic move to gain freedom and shift into a new season of life. ➥ A clean, simple business model and solid financials were critical in structuring a successful sale. ➥ SBA loans can be powerful tools for acquiring businesses, but creative financing is often just as effective. ➥ You don’t always have to operate the businesses you buy—systems, leadership, and delegation are key. ➥ Real estate offers stability while business offers higher returns—knowing when to lean into each is crucial. ➥ Long-term vision and emotional resilience helped Justin overcome $120K in debt and build real wealth.   About Justin Williams Justin Williams dropped out of college with a bold vision, convincing his wife, Tara, to leave her teaching job so they could start their first business. But their million-dollar dream quickly turned into a $120,000 debt nightmare. Determined to turn things around, they hustled out of debt and pivoted to real estate, eventually flipping 100 houses a year. Their success led them to launch House Flipping HQ, helping others build thriving real estate businesses. After selling the company, they took time off to focus on investments and new ventures.Now, as the founders of Millionaire University, their mission is simple: help people "graduate rich, NOT broke." With over 600,000 monthly podcast downloads, MU is transforming how entrepreneurs learn, grow businesses, and create wealth.     Connect with Justin Williams ➥ https://www.millionaireuniversity.com/    Resource Links ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Hostinger (Website Hosting) - https://bit.ly/3HUqW0s ➥ SEM Rush (SEO tool) - https://bit.ly/3lINGaV ➥ Convert Kit (Email Software Provider) - https://bit.ly/3o10Xgx  🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3Zp