Cash Flow Connections - Real Estate Podcast

Evan Holladay was three months from closing a $120M affordable housing development... Then he got a tweet. A government agency had pulled the $7 million grant he was awarded. No phone call. No meeting. Just... gone. That’s the reality of building in the affordable multifamily space—a world filled with public-private partnerships, massive upside, and government curveballs. But Evan has figured it out. He's developed over 2,700 units and $626M in projects using tax credits, political strategy, and creative capital stacks most investors have never touched. In this episode of Cashflow Connections, we dive into: How the new “Big Beautiful Bill” could unlock 1.2M new units Why affordable housing offers permanent demand and less competition The exact 3-part funding structure behind every deal How to land your first tax credit project (even with zero experience) What politicians, syndicators, and students are now doing to get involved And why Evan is teaching others to build their own “mountains” and multiply their impact through his Affordable Development Mastery program. If you’ve ever wanted to create long-term cash flow and solve a massive societal problem… You need to hear this conversation. Take Control, Hunter Thompson Resources mentioned in the episode: Evan Holladay Previous episode: Looking Into the World of Affordable Development YouTube LinkedIn Instagram Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In this Topical Tuesday episode, I spoke with Bob Fraser who is the chief macro strategist of Aspen Funds. He's also a former tech founder and Ernst & Young Entrepreneur of the Year, and he's the author of - "Invest Like a Billionaire - Unlocking the Billionaire Model". Be sure to tune in if you’re interested in learning about: Why the traditional 60/40 portfolio is outdated and how it's failing today’s investors How billionaires allocate capital The limitations of public REITs vs. private real estate syndications Practical advice on how everyday investors can get started with alternatives and avoid common mistakes To your success, Tyler Lyons Resources mentioned in the episode: Bob Fraser The Billionaire Book Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In today’s Monday Minutes episode, I cover breaking news: the SEC is revisiting how capital raisers might legally get paid without going through a broker-dealer. This could be a game-changer for those who want to raise funds or compensate others to do so—legally and efficiently. Tune in to learn what this could mean for your capital-raising strategy. Resources mentioned in the episode: Hunter's Instagram Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In today’s RaiseMasters Radio episode, Adam sits down with Casey Stratton to discuss how his team is expanding beyond multifamily into new investment strategies—including a powerful joint venture with Aspen Funds and a tax-advantaged offering for IRA and estate investors. Casey shares how his vision for Tamarack Capital has evolved, what’s coming next, and the role RaiseMasters played in shaping his trajectory. Tune in to hear how one capital raiser is leveling up his business and helping investors do the same. Resources mentioned in the episode: Casey Stratton LinkedIn Website Book Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

When the U.S. bombed Iran, most people tuned into the headlines… But very few stopped to ask: What does this mean for the dollar? For interest rates? For inflation? That’s exactly why I brought on Kirk Elliott—a PhD in public policy with decades of experience studying geopolitical and economic shifts. Because this isn’t just about war. It’s about oil shocks, debt spirals, rate policy gridlock, and how your investment strategy could be blindsided if you’re not paying attention. In this episode, we dive deep into: How geopolitical conflict triggers energy inflation—and why it hits everything from gas to groceries Why the Federal Reserve may be stuck between crushing inflation and triggering a recession How Japan’s decision to end the yen carry trade quietly killed a major engine of global liquidity What a weakening dollar could mean for U.S. manufacturing, exports—and real estate Why traditional investment advice could be disastrous in today’s environment Kirk lays it all out in plain English. No hype. No political bias. Just clear cause-and-effect logic that every investor needs to hear. If you’re trying to make sense of what’s happening in the markets and how to position yourself for what’s coming next… This is the episode. Take Control, Hunter Thompson Resources mentioned in the episode: 1. Episode with Alex Epstein Anti-Science Claims About COVID & The Environment 2. Kirk Elliott X/Twitter Website Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In this Topical Tuesday episode, I spoke with Sam Morris who is a Partner at Lone Star Capital, where he oversees acquisitions, asset management, and investor relations. Be sure to tune in if you’re interested in learning about: The HB 21 legislation and how it affects tax abatement strategies in Texas multifamily deals The difference between in-jurisdiction and out-of-jurisdiction HFCs, and why the “traveling HFC” model is under fire Key investor concerns like the new rent reduction test and the lack of a grandfather clause The potential legal and financial ripple effects of the law—including lender lawsuits and risk to affordable housing supply To your success, Tyler Lyons Resources mentioned in the episode: Sam Morris Website Email Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In today’s Monday Minutes episode, I share two powerful lessons from my keynote at the Capital Collective Mastermind: why the trend is your friend—and why there's no such thing as a free lunch. These truths can help you avoid chasing short-lived wins and build something lasting. Tune in to gain the right mindset for long-term success. Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In today’s RaiseMasters Radio episode, Adam sits down with Marco Pfeiffer, a lifestyle investor who retired from his corporate CFO career to build a single-family real estate portfolio and never looked back. They discuss his journey to financial freedom, how he uses real estate as a hedge against currency debasement, and why cash flow is king. Plus, we talk about how he grew a loyal following on LinkedIn by being unapologetically authentic. Tune in to hear how Marco’s bold approach to investing and life can inspire your next move. Resources mentioned in the episode: Marco Pfeiffer LinkedIn Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

While most people are relaxing this summer… The smartest business owners are slashing their tax bills using strategies you’ve probably never heard of. That’s why I brought back Mark Kohler—CPA, attorney, and wealth architect—to break down the real summer tax moves investors should be making now. In this episode, we cover: Why “side hustles” and family barbecues can become powerful tax deductions How to legally pay your kids—and take the write-off The #1 LLC mistake that could cost you everything What board meetings with your family have to do with asset protection How to convert “summer fun” into a tax strategy And yes—this is all 100% legal and totally underused. If you’ve ever thought tax planning was boring… Mark will change your mind. Listen to the episode now. Take Control, Hunter Thompson Resources mentioned in the episode: Mark Kohler Personal Website KKOS Lawyers Website Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In this Topical Tuesday’s episode, I spoke with Dave McIlwaine who is a seasoned entrepreneur and successful executive with deep experience in business growth, scale and delivering results. He has 25 years of experience in the world of real estate and he is the Founding Partner of MAC Assets, where he acquires underperforming multifamily value-add properties with substantial opportunity to generate short and long-term gains. Be sure to tune in if you’re interested in learning about: The risks associated with W-2 employment and how it’s easy to underestimate those risks How he “broke the golden handcuffs” of his W-2 and what tactics he used to help him prepare for it How to think about timing the exit from a W-2 to become a full-time entrepreneur How coaching has been beneficial to him in both life and entrepreneurship What the difference is between a teacher, mentor and a coach To your success, Tyler Lyons Resources mentioned in the episode: Dave McIlwaine Website Podcast LinkedIn Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In today’s Monday Minutes episode, I break down whether you should go all in on YouTube to raise capital. I share what’s working, why I’m diving in, and how to decide if it fits your voice and audience. Tune in to hear what could be the next big unlock for your business. Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In today’s RaiseMasters Radio episode, Adam sits down with Shelon “Hutch” Hutchinson—Marine veteran, real estate syndicator, and co-founder of H² Capital. We talk about how he went from barefoot in Jamaica to building a fund of funds serving military investors, why mindset is everything, and how curiosity kills mediocrity. Hutch breaks down what it really takes to be a steward of capital and build a legacy that lasts. Resources mentioned in the episode: Shelon Hutchinson LinkedIn Website Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In 2021, you could close your eyes, hand a property to a third-party manager, and still double your money. Not anymore. Today’s market is a different beast—rising interest rates, valuation corrections, overbuilding, and tightening debt markets have completely changed the rules. That’s why I brought back Josh Welch and Mark Shuler—two operators with over 4,000 units under management—to unpack exactly how they’re navigating the storm. In this episode, they reveal: Why efficiency and process are the new unfair advantage How to scale property operations without losing control The hidden risks in today’s debt markets most investors are ignoring How top operators are buying deals at 2018 prices… and winning Josh also shares how his in-house team is turning struggling properties around, even ones with 30% delinquency. If you’re serious about navigating the next cycle and staying ahead of the herd…listen to the episode now. Take Control, Hunter Thompson Resources mentioned in the episode: 1. Josh Welch Website 2. Mark Shuler Website Email Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In this Topical Tuesday episode, I spoke with Scott Trench, who is the former CEO of BiggerPockets, and the author of Set for Life - Dominate Life, Money, and the American Dream. He's also an investor, a financial freedom advocate, and the co-host of the Bigger Pockets Money podcast. Be sure to tune in if you’re interested in learning about: How Scott built financial freedom through frugality, house hacking, and small multifamily properties Why many “FIRE” investors struggle to actually withdraw from their portfolios, and what to do instead Lessons from investing as an LP in syndications and how to assess operator credibility and deal quality Scott’s outlook on multifamily real estate and what to expect in the next few years To your success, Tyler Lyons Resources mentioned in the episode: Scott Trench BiggerPockets Money Podcast YouTube Instagram LinkedIn Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In today’s Monday Minutes episode, I share a tough truth: your current problems are small compared to the ones you’ll face if you keep leveling up. But that’s exactly why you need to keep going. Tune in to hear why growth demands heavier burdens—and why you’ll be ready. Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In today’s RaiseMasters Radio episode, Adam is joined by Dasha Beardsley, author of Maximizing Wealth Through Syndicated 1031 Exchanges. They talk about her journey writing the book, why syndicated 1031s are still a hidden gem for many investors, and what it really takes to publish a high-value resource in today’s AI-heavy world. Dasha also shares what Lone Star Capital is focused on right now and offers some insight into how RaiseMasters has helped her along the way. Tune in to hear how she turned an ebook idea into a true industry resource. Resources mentioned in the episode: Dasha Beardsley Book Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

The recession everyone feared in 2024? Taylor St. Germain says it’s not coming—not yet, anyway. In fact, he believes we’re heading into five years of aggressive growth…Before a major downturn hits in 2030. In today’s episode, we go deep into: Why capital markets are frozen by uncertainty (and how to play offense while others stall) How inflation, demographics, and rising labor costs are priming the system for a 2030 collapse What industries are most vulnerable over the next five years Why interest rates could climb to 9%… and what that means for debt-heavy investors How to read between the lines of media noise and identify the real economic signals This isn’t theory—Taylor’s firm has one of the most accurate forecasting records in the business. If you want to get ahead of the next economic cycle instead of reacting to it… Tune in to the episode now! Take Control, Hunter Thompson Resources mentioned in the episode: Taylor St. Germain Podcast Website LinkedIn Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In this solo Topical Tuesday episode, Tyler dives deep into a seemingly obvious, yet nuanced, topic: why occupancy is absolutely critical for multifamily properties, especially in today's competitive Sunbelt markets. Be sure to tune in if you’re interested in learning about: Why vacancies might be more expensive than you think — including some hidden costs that often go unnoticed The true cost of turning over a unit and why it’s not just about paint and repairs How a full building can quietly outperform aggressive rent strategies and what that means for your bottom line Smart, often-overlooked tactics for keeping residents longer and how timing plays a key role To your success, Tyler Lyons Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In today’s Monday Minutes episode, I answer a common question from capital raisers: Should you hire a closer to take investor calls? I break down when it makes sense—and when it’s just a distraction from the real bottleneck. Tune in to learn how to know if you’re ready. Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In today’s RaiseMasters Radio episode, Adam is joined by Jason Wright of Intentionally Inspirational. They talk about what it really takes to succeed in capital raising right now, why consistent relationship-building beats pitching deals, and how to adapt your marketing to match what investors are actually looking for. Jason also shares tactical tips on digital advertising, staying motivated during tough markets, and using tools like Grok AI for real-time insights. Tune in to hear why action beats perfection—every time. Resources mentioned in the episode: Jason Wright Website Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

Most investors think preferred equity is only for "rescue deals"... But what if that’s dead wrong? In my latest episode of Cashflow Connections, I sat down with Paul Moore—founder of Wellings Capital, $195M+ raised, and a two-time finalist for Michigan’s Entrepreneur of the Year. He revealed how the best investors are using preferred equity not as a last resort but as a strategic weapon in today’s market. We cover: Why preferred equity with a 17%+ return is still alive and thriving How “JV Hybrid Equity” is changing the capital stack game What Buffett got wrong about diversification—and how Paul fixed it Why floating-rate debt might actually be safer now than in 2022 This one is for serious investors who want to understand how capital is really moving in 2025. Take Control, Hunter Thompson Resources mentioned in the episode: Paul Moore Website Resources Previous Episodes: Speculating vs Investing The Ultimate Checklist for Self-Storage Investing Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In this Topical Tuesday episode, I spoke with Aleksey Chernobelskiy who advises Limited Partners (“LPs”) on existing and future investments. He writes weekly to thousands of investors at LPlessons.co to explain how to properly vet and think about LP investments in the grand scheme of their portfolios. Aleksey also helps General Partners on matters relating to LPs, such as capital calls or feedback on investment decks. Be sure to tune in if you’re interested in learning about: A practical breakdown of the three-part framework LPs should use to evaluate syndications Why track record inflation is common—and what investors should really look for when assessing experience Where LPs often underestimate risk and how to think clearly about capital calls and downside scenarios The biggest mistakes investors make when relying too heavily on IRR projections To your success, Tyler Lyons Resources mentioned in the episode: Aleksey Chernobelskiy LinkedIn Twitter Website Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In today’s Monday Minutes episode, I break down how to actually get the attention of billionaires and top-tier operators—without sounding cringey or wasting their time. It’s all about relevance, research, and real value. Tune in to learn how to stand out in a crowded room. Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In today’s RaiseMasters Radio episode, Adam sits down with Josh Washington, a long-time teammate at RaisingCapital.com and one of our top client success partners. From performing with acts like the Jabbawockeez to helping capital raisers raise millions, Josh’s journey is anything but typical. We talk about what separates elite capital raisers, the power of storytelling, and why your “who” is more important than your “how.” Tune in to hear how Josh helps new and experienced members alike build real momentum. Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

Every real estate investor has heard of bonus depreciation... But in 2025, the game has changed—and if you're not up to speed, it could cost you. In today’s episode, I sat down with Gian Pazzia, a cost segregation expert with a background in engineering and Big Four accounting. He breaks down exactly what’s changed, what’s staying, and how to capitalize on bonus depreciation while it’s still available. Whether you're holding small rentals or $10M commercial deals, this is a must-listen if you want to reduce your tax bill legally and massively. In this episode, we cover: How cost segregation really works (with simple math examples) When it makes sense to pay for a study—and when it doesn’t What “recapture” means and how it can ruin investor returns if misunderstood The political outlook for bonus depreciation (hint: it might return to 100%) How Gian’s firm is using AI to help smaller investors get in the game Listen now and make sure your tax strategy is 2025-ready. Take Control, Hunter Thompson Resources mentioned in the episode Gian Pazzia Website LinkedIn Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In this Topical Tuesday episode, I spoke with Pete Schnepp who is the founder of Asset Stream Properties and has leveraged over 20 years of experience in real estate and construction to build a firm that specializes in low-risk, high-reward investments in multifamily workforce housing. Be sure to tune in if you’re interested in learning about: How a lawsuit shifted Pete’s mindset from relying on a single business to building multiple income streams. How he started with one property per year and scaled to a multi-million-dollar portfolio using seller financing and creative deal structures. Off-market sourcing methods, including VA-led cold calling and targeting tired landlords for seller-financed opportunities. How his investment goals have evolved from covering living expenses with cash flow to building long-term wealth through appreciation and development deals. To your success, Tyler Lyons Resources mentioned in the episode: Pete Schnepp Website LinkedIn Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In today’s Monday Minutes episode, I share a mindset shift I’ve picked up from endurance training—and how it applies directly to business. It’s all about learning to treat hard work as an honor, not a punishment. Tune in to reframe your relationship with intensity. Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In today’s RaiseMasters Radio episode, Adam sits down with Tyler Goldman, a rising entrepreneur in the capital raising space who just locked in his first deal in Charlotte. We talk about his transition from institutional real estate to launching his own firm, what he's learned during his first fundraise, and how he's leveraging systems to accelerate his success. If you're building your capital raising machine, this one’s for you. Resources mentioned in the episode: Tyler Goldman Email LinkedIn Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

When Dr. Chirag Chaudhari started investing in real estate, he was just looking for a smart way to diversify… He didn’t expect to become a capital-raising powerhouse for hundreds of other physicians. But once he discovered syndications and joined a real estate mastermind everything changed. Fast forward to today: Over 20 LP investments 787 hotel-to-multifamily units as a GP An elite STR fund + ground-up construction in San Diego And millions raised from high-income professionals like himself In this episode, you’ll hear how Chirag went from “just a doctor doing deals on the side” to a trusted resource for investors across the country. Inside, we break down: How he overcame imposter syndrome and built credibility fast His methodical sponsor vetting process (including criminal background checks) The one email that sparked massive interest from his network Why oil & gas is his next big move—and what most investors miss If you’re trying to raise capital without sounding like you’re “asking for money,” this one’s gold. Listen to the episode now! To your success, Hunter Thompson Resources mentioned in the episode: Chirag Chaudhari Website Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre

In this Topical Tuesday episode, I spoke with Tait Duryea who is the CEO of Turbine Capital. He has over a decade of experience in single-family, multifamily, self-storage, industrial, mobile home parks, and short-term rentals. In early 2023, he co-founded the Passive Income Pilots, a financial education resource for aviators. Be sure to tune in if you’re interested in learning about: How real estate professional status (REP) can help offset active income with strategic tax planning. The short-term rental loophole and how it benefits high-income earners. Why oil and gas can be a compelling investment beyond the tax benefits and what risks to consider. How LPs should vet oil and gas opportunities, including operator experience and liability exposure. To your success, Tyler Lyons Resources mentioned in the episode: Tait Duryea Email Website Ebook Interested in learning how to take your capital raising game to the next level? Meet us at Capital Raiser’s Edge. Learn more here: https://raisingcapital.com/cre