Tropical MBA: Entrepreneurship & Founder Lifestyle

Longtime listeners know that Dan and Ian have been business partners for many years, and sometimes it's hard for us to imagine what it would be like to run a business on our own. So many entrepreneurs do choose this path, though, and the quest of a "Solopreneur" can be a long and arduous one. Darren Joe is the director of TouchMBA, a service that matches prospective students with MBA programs. He is also the author of a new book called "The Fail-Safe Solopreneur", where he offers some insights and practical exercises to help navigate the journey of the solopreneur. Darren joins us on today's podcast to talk about his own journey as a solopreneur, what inspired him to write this book, why he has chosen to make Ho Chi Minh his home, and much more.

We aren't usually the type for navel-gazing, but this summer marks an important milestone for us. 10 years ago, our desire to "find our tribe" led us to form the Dynamite Circle, a private membership community of location-independent entrepreneurs. Since then, there have been dozens of DC events all over the globe, and it has truly become a life-changing adventure for so many of the people involved in the community over the last decade. We've invited our good friend Jeff Pecaro on to the podcast this week to look back on the ups and downs of the last ten years of the Dynamite Circle. We are also going to pull back the curtain a bit and discuss the behind-the-scenes details of what it's really like to run a private community and the unique challenges that these types of businesses present.

This week's episode was inspired by a question from a listener. Katie recently graduated with her master's degree, and while she appreciated the insight that we've shared in the past about how to get a remote job, she wanted to know more about what it takes to succeed at a remote position once you get it. This got our wheels spinning, and we put together a list of five important factors that can help employees become "A Players" in their remote positions. This conversation is of keen interest to remote employees and employers alike. You'll hear about the difference between good employees and great ones, why "B players" have been struggling with remote positions, and a whole lot more. We'll also be sharing some news about our first event in nearly two years.

Nick Huber has been on a wild ride since we last spoke to him in 2019. Nick is the host of a podcast called The Sweaty Startup, and at the time he was running a business called Storage Squad, a storage company that helped students store their belongings at universities all across America. Covid threw that business for a loop, but Nick was able to make some fast decisions that allowed him to sell that company and pivot into a new endeavor, a multi-million dollar real estate private equity company called Bolt Storage. Nick joins us on this week's podcast to share what happened when the coronavirus pandemic shut down most of his business, why he has decided to pivot into the real estate business, how he utilizes Twitter to help find investors, and a whole lot more.

Summer is here, and it's starting to feel like things are returning to "normal." For many of us in the community, that means that we're finally going to have the opportunity to pick up our backpacks and return to nomadic life. Jesse Schoberg is the co-founder and CEO of DropInBlog.com, a Software as a Service platform that helps users add blogs to their websites. Jesse has been a full-time nomad for over 7 years, and he joins us on this week's podcast to discuss how he was able to transition from running an agency to creating a product, and why he finds the nomadic life so appealing. If you're ready to get back on the road, or perhaps you've decided that it's finally time to double down on entrepreneurship and go remote, this is the episode for you.

A few weeks ago we said something on this podcast in jest, but one of our more attentive listeners latched onto it. "I find myself some days waking up and saying 'are we going to make it?'" Our good friend John Ainsworth heard this and he reached out to us with a little bit of concern, hoping to find out more. What exactly does it mean when we ask that question, "are we going to make it?" We'll be seeking the answer to that on today's podcast, as well as sharing five principles that we have been employing recently in our quest to grow an 8-figure business. Stick around to the end of the episode to hear a tribute to one of our dearest friends.

We've learned over the years that being a part of a community of like-minded people is one of the most valuable experiences that you can have as an entrepreneur. This was our core motivation for forming The Dynamite Circle, our own online community of location-independent entrepreneurs, back in 2011. We originally built that community on a platform called Ning, largely because it was the best option on the market at the time, and it served us well for many years. Gina Bianchini is the former CEO of Ning. She recently decided to leave that company to create Mighty Networks, a sophisticated platform aimed at helping creators build their own online communities. We've invited Gina on to the podcast today to talk about the challenges of building and running online communities in 2021, how communities on the internet have evolved over the past decade, how to grow an 8-figure remote business, and more.

This week's episode is full of so many recurring themes that we've seen over the years on this podcast, from the unique struggles that SaaS businesses face, to the decision between bootstrapping and funding, and much more. Derrick Reimer has had a long and storied career as a software entrepreneur, but he is perhaps best known as the technical co-founder of Drip, which he built alongside our good friend and former guest Rob Walling. Since exiting Drip three years ago, Derrick jumped headfirst into his next project: a team-chat software named Level, which he ultimately chose to walk away from in 2019. Today, Derrick joins us to talk about why he made the decision to shut down the product that he has spent a year building, as well as the details of his newest project, a sophisticated scheduling tool named SavvyCal.

We've shared a lot of stories on this podcast from entrepreneurs who have started their own businesses, but one strategy we've increasingly seen to accelerate the path to wealth is to purchase a business that already exists and to leverage debt to do so. Today's guest is an expert at that. Shakil Prasla has been acquiring businesses through his company SZ Ventures for nearly a decade. He started with a loan from the Small Business Administration and now has a team of roughly 80 people who are managing niche eCommerce companies. They are selling anything from high-end business cards to their most recent acquisition, Gloves.com. In today's podcast, Shakil shares the story of how he purchased his first business, how he has grown to where he is now, strategies for taking advantage of Small Business Administration loans, and much more.

Today's episode is all about creating content, in particular, how to create written content that people actually want to read. David Perell is the co-founder of an online writing school called Write of Passage, and he is an expert at teaching people how to cultivate ideas and distill them into writing. He's also an extremely savvy marketer, with tons of important insights into the future of social media and internet marketing. David joins us on today's podcast to share specific writing strategies that have worked for him, what it really takes to grow a Twitter account that has the potential to change your business, and a whole lot more.

This week's podcast is a little bit out of the ordinary. While we have been busier than ever this month over at Dynamite Jobs, we still can't help but find things on the internet to get worked up about. We thought it would be fun to take a look at five specific news items and ideas that have recently come across our desk that we just can't stop thinking about. These topics range from how to deal with FOMO, why it's important to get powerbrokers involved in your business, the "muddy middle" of freelancing, and so much more. We hope that these five topics can help inspire you to make the next great move in your location-independent business.

Welcome back to another episode in our long-running series The Re-Readables, where we revisit some of our favorite business books to find out if they stand the test of time. How to Get Rich was written in 2009 by author and entrepreneur Felix Dennis. Felix was the founder of Maxim magazine, and he aimed to create a book about getting rich from "someone who didn't need to write it". The result is incredibly funny, direct, and thought-provoking. Joining us this week is our good friend Coran Woodmass of TheFBABroker.com, who has just read the book for the very first time and is eager to share his thoughts. We'll be discussing the finer points of How to Get Rich, what we believe has aged the best and what has aged the worst, some of our favorite quotes, and much more.

This week's episode features insider knowledge on the processes behind hiring and recruiting remote talent from someone who has been deeply involved in the industry for over a decade. Greg is the Senior Recruiter at Dynamite Jobs, as well as one of The Bossman's closest friends. Avid listeners might remember his name from the "ferret story" that we've shared on this podcast in the past. (We'll touch on it again in this episode as well) His addition to our team has been pivotal as we've been developing our flat-rate done-for-you recruitment services. Greg joins us on the podcast this week to talk about his history in the job recruitment industry, how and where he finds the best candidates for jobs, which skills are in the hottest demand right now, and so much more.

This week's episode is another installment of "The Re-Readables", a series in which we revisit some of our favorite business books to find out if they stand the test of time. Greg Gerber has become something of a regular contributor here on the Podcast. Greg is the founder of BitLift, and he is our go-to guy for all things blockchain and cryptocurrency. Greg joins us this week to talk about a book that has become eerily prescient, particularly among the cryptocurrency crowd. The Sovereign Individual by James Dale Davidson and William Rees-Mogg was published back in 1997, but the insights and topics in the book were not only far ahead of their time, but they remain eerily relevant today. In today's podcast, you'll hear our thoughts on why this book is still so important, why it's important for entrepreneurs to be able to see into the future, and how we can consider the ideas within The Sovereign Individual when attempting to look to the future ourselves.

We've been seeing some truly explosive growth at Dynamite Jobs since the start of 2021, and we've been helping more businesses than ever find great remote talent for their teams. When our friend Brendan Tully reached out to us on Twitter recently with some suggestions on how we could help candidates find better jobs, we knew we had to talk to him. Brendan is the CEO and founder of Robotmedia, which helps small businesses get more traffic and better conversions. He has been doing quite a bit of hiring recently, and he has developed some strong opinions about the hiring process, particularly in how we can better educate job prospects who are applying for remote positions. Brendan joins us today to talk about what he looks for when browsing candidate resumes, what a great resume looks like, and what he believes that candidates can do to have a better chance of getting a great remote job.

What if your knowledge as an entrepreneur could benefit you as an investor? We've talked about cryptocurrency and unorthodox investments in the past on this show, but the traditional financial system is still something of a mystery to a lot of entrepreneurs. Enter Simon Stock. Simon is a longtime friend of ours, who cut his teeth as an entrepreneur running eCommerce businesses. These days, Simon is a full-time investor, and his approach to the stock market is not unlike the way that many of us have run our own businesses. Simon joins us this week to talk about what entrepreneurs can stand to gain from investing in the stock market, what investment strategies have worked for him in the past, and how our entrepreneurial skillset can help us when investing in the traditional financial system. Disclaimer: The ideas discussed in this podcast are for entertainment purposes only and should not be considered financial advice.

Our good friend Noah Kagan recently published a video that caught our attention. Noah is the founder of AppSumo.com, and his YouTube channel has been one of our favorite destinations as of late for thoughtful content about entrepreneurship and creating wealth. That video was called 10 Surprising Things About My Richest Friends, and in it, Noah outlined some specific habits that he has seen time and time again among the wealthiest people in his social circle. We were so enthralled by some of the unorthodox ideas that he presented in that list, that we knew we had to talk to Noah to dig a bit deeper into what he had learned. In today's episode, Noah joins us to discuss the types of habits that the super-wealthy have cultivated, how people become wealthy in the first place, and what we can do to emulate some of these behaviors ourselves.

We always love receiving thoughtful questions from Tropical MBA listeners around the world. A few weeks ago, a winter storm in Texas forced us to re-run one of our favorite episodes of this show called 7 Things to Consider When Selling Your Business, in which Dan and Ian describe the process of selling their eCommerce business back in 2015. Our decision to revisit that particular story elicited a ton of responses from those of you who had never heard it before, and from those who were listening to it with a fresh perspective nearly five years later. This week we are responding to several listener questions about that story, discussing our feelings on the exit nearly five years later, addressing how long it really takes to "fire yourself" from your business, and a whole lot more.

We've been devoting a lot of time on this podcast recently to SaaS or "Software as a Service" businesses. That's because we love the upside of SaaS, including the potential for generating recurring revenue and creating life-changing exits. But is it possible to create a software business without knowing how to code? Alan VanToai is the founder of CrewFire.com, a brand ambassador and influencer management platform. Alan has very limited technical expertise, but that hasn't stopped him from creating and exiting from multiple software ventures. Alan joins us on today's podcast to discuss how you can start a SaaS business without a technical partner, how to attract a technical partner when the time comes, and some personal feelings about one of our very favorite places in the world: Vietnam.

When it comes to entrepreneurship, failure can often be more important than winning. So many of the greatest success stories start with failure because it's what we learn from those failures that ultimately leads us to the success that we seek. Today's guest describes himself as "an expert at failure". Sean Markey started his career as a special education teacher and spent the better part of a decade bouncing between jobs and going into debt, all the while trying to find a way to earn a living online. Despite several high-profile failures, Sean managed to hone his skills at SEO and started creating and building websites that earn affiliate income. He recently sold one of those websites for what he described as "life-changing money". Sean joins us this week to discuss some of his greatest failures, how he was able to learn the skills that ultimately led to his success, and why failure itself is such an important part of the entrepreneurial journey.

When we received an email from today's guest, we were fascinated by his story and we knew that we had to speak to him. Curtis Boyd is the founder of two incredibly unique businesses. The first one is a bespoke consultancy for high-level service companies and the second one is a software as a service business called Objection.co. Both of these businesses were created with a singular goal in mind: to identify and dispute fake reviews on the internet. Curtis began by disputing a single review for his first client and soon found himself competing in an arms race with fake reviewers in what has become a multi-million dollar industry of deception. Curtis joins us this week to discuss how a chance encounter led to his unique consulting career, why he decided to go back to school to learn about artificial intelligence, tips for identifying fake reviews, and a whole lot more.

After a wild and dramatic week in Austin TX, we are excited to return to our regularly scheduled programming and to highlight an entrepreneur with a unique career trajectory. Casey von Neumann started out as many of us do, by freelancing, teaching music classes to students in Atlanta, G.A. As her client base grew, she began scaling her services into a full-blown music school called Eclectic Music and has since built multiple businesses in the education space. It wasn't long though before Casey discovered that she had trapped herself in the day-to-day operations of her business. She was forced to come to the difficult realization that she was a "bad boss" who needed to make fundamental changes to the way that she interacted with her team. Casey has recently begun sharing what she has learned from that experience by coaching entrepreneurs in an area where so many of us struggle - building, keeping, and managing a team. Casey joins us this week to share her entrepreneurial origin story, what it means to be a "bad boss", and how we as entrepreneurs can take steps at the onset of our business to create a better work environment for ourselves and our employees.

Austin, TX was hit by a very unique winter storm preventing the team from putting out a full episode this week.

This week's episode features a story with a lot of familiar themes. Today's guest started out as so many of us do, with a weekend side hustle. Amar Ghose is the CEO of ZenMaid, a niche scheduling software for maid services that he co-founded in 2013. When his first attempt at launching a maid services company failed, Amar was able to use what he learned from that experience to pivot into a software product designed for other businesses in the maid services industry. Amar joins us this week to talk about the origins of ZenMaid, what playing online poker has taught him about running a business, how he has applied digital marketing strategies to a blue-collar industry, and a whole lot more.

Today's podcast is about a topic that near and dear to our hearts and one that we've actually written a book about in the past. Longtime listeners know that roughly six years ago we sold our product business, and in the years since we have spent a considerable amount of time processing that decision and examining what happens not only at the core of successful exits but in the aftermath of them as well. John Warrilow is the author of a trilogy of books about this very subject, including Built to Sell, The Automatic Customer, and his most recent book The Art of Selling Your Business. He has also spoken with hundreds of entrepreneurs on his own podcast (including our very own Bossman) about their experiences exiting from their businesses. John joins us on this episode to discuss what makes a successful exit, how to build a business with the intention of selling, what he has learned from speaking to entrepreneurs about exits over the years, and so much more.

Since the start of the year, we've been focusing heavily on stories about starting new businesses as well as what we believe are the "fundamentals" of being an entrepreneur. When we received a video message from today's guest, who was telling us how excited he was to finally join our private membership group The Dynamite Circle, we knew we had to hear more about his story. In just a few short years, Sam Hill has grown his company E Comm CFO to nearly $300,000 in annual revenue, and he was able to do it by straight-up hustling on the freelancing platform Upwork. This week, we've invited Sam onto the podcast to share the origins of his entrepreneurial story, the nuts and bolts of how he was able to grow a business on Upwork, and some of his guiding principles for entrepreneurship.

We've been spending a lot of time over the past few weeks talking about the "business fundamentals", or the everyday habits that we believe entrepreneurs should be practicing. In keeping with that theme, we've decided to revisit some specific concepts that we've spoken about on this show in the past, and that we have seen at the core of so many successful entrepreneurial stories. On today's podcast, we'll be sharing four frameworks for how to get started with a profitable business idea in 2021. We'll be exploring each of these philosophies, as well as citing some specific examples of how each of these frameworks have been used successfully by the entrepreneurs that we have featured on this podcast in the past.

January is one of our favorite months of the year because it's a time for starting over, setting new goals, and making plans for how to achieve them. It's no surprise then that our inbox starts filling up with messages from excited entrepreneurs who are looking for new ways to push forward with their businesses. This week, we're reaching into the mailbag once again to answer questions submitted by Tropical MBA listeners around the world. We'll be discussing a series of topics specifically related to starting new businesses, finding new revenue streams, and making new moves in your business in 2021.

Every once in a while a book comes around that completely captivates us and leaves us with more questions than answers. When we discovered "The Price of Tomorrow" by Jeff Booth, we knew we needed to hear more from the man who wrote it. Jeff is a Canadian-based entrepreneur who has built and invested in numerous companies, including BuildDirect, which he helped grow to $220 Million dollars in annual revenue. We were absolutely taken by the ideas he presented in his book, as well as Jeff's perspective on the future of the global economy. Jeff joins us on today's podcast for what turned out to be an incredibly poignant conversation about the global financial system, inflation and deflation, technology, and so much more.

This is the time of year when so many people are making goals and resolutions. These types of things are great, but we've always believed that the best way to is to see real progress is to create healthy habits and practices. Successful athletes do this by continuing to practice their fundamentals, the core skills that are most important to their game. Today we're going to be looking at how we can practice our business fundamentals so we can improve our daily habits and set ourselves up for success in the new year. We'll be sharing some specific ways that you can improve your finances, your time, your relationships, and much more.

To say that the last twelve months were unpredictable would be a massive understatement. For ourselves and so many other entrepreneurs, the COVID outbreak not only threw a wrench into our plans for 2020, it completely changed the way that we did business this year. Many of us were operating in industries that were adversely affected by the pandemic on a profound scale. Others, particularly those in eCommerce, experienced one of the most successful years of their entrepreneurial careers. In today's episode, we are revisiting some of the highs and lows of a wild and unforgettable year. You'll hear our opinions on how the year has played out on a broader scale, some insights into how our own businesses have fared over the year, and some highlights from our favorite moments on the podcast in 2020.

Like so many other entrepreneurs, we are fascinated by cryptocurrencies. We are naturally drawn to the technology because we believe it has the potential to cause some serious disruption in the financial sector. You might recall a few years back that we interviewed Nathaniel Popper about his book Digital Gold, which chronicled the origins of Bitcoin. Today's guest has written what feels to us like the next logical chapter of that story. Jeff Roberts is the author of Kings of Crypto, a book that details how the cryptocurrency startup Coinbase drove crypto out of the shadows of the internet and into the mainstream financial industry. Jeff joins us this week to talk about how the book came to fruition, crypto's evolving place within mainstream finance, the ideological battles happening within the space, and so much more.

Even though 2020 has been a difficult year for some entrepreneurs, it has arguably been an all-time year for many people running eCommerce businesses. Longtime listeners know that we first cut our teeth in the eCommerce space, and we love keeping tabs on how that industry continues to evolve and innovate. It's no surprise then that today's guest made his way onto our radar. Aaron Rubin is a longtime veteran of eCommerce. Aaron's growing annoyance with the shipping costs related to his business drove him to create ShipHero, a remote company that offers outsourced shipping fulfillment services and warehouse management software to other eCommerce businesses. Today, more than 1 in every 200 eCommerce packages delivered in America are shipped through ShipHero. Aaron joins us today to share his story. You'll hear how his first eCommerce business nearly went bankrupt, how a need to "scratch his own itch" led to the creation of ShipHero, and Aaron's somewhat insider take on where the eCommerce industry is headed in the future.

We are reaching back into the mailbag this week to answer questions submitted by Tropical MBA listeners around the world. In this edition, we'll be focusing on three specific questions that we believe get to the core of what it means to be resilient as an entrepreneur. We'll be discussing how much money you should save as a "runway" if you plan on leaving your job, the fundamental differences between hiring freelancers and hiring employees, and how you can navigate questionable business advice on the internet. You'll also hear an update about the new products that we are launching over at Dynamite Jobs, and why we are somewhat optimistic about events returning in 2021.

This week's episode is about something that is incredibly near and dear to our hearts: personal blogging and what it means to write on the internet. To help us tell this story, we've invited two of our favorite writers who both have a long and rich experience in the blogging space. Taylor Pearson has been a frequent guest and contributor on this podcast. He is the author of The End of Jobs, and he runs an excellent blog over at TaylorPearson.me that has been required reading for us for quite some time. Amanda Cook is an author, a podcaster, herbalist, and the founder of a business called Wellpreneur. Over the years, she has published online about a wide variety of projects, but the one consistent thing is that she's always had an excellent blog, which you can find at AmandaCook.me. Join us for this round table discussion about the past and future of blogging on the internet, tips for those starting out with a personal blog, some of our favorite blogs to read today, and so much more.

We've been receiving a ton of requests recently from listeners who want to hear an "old school" episode, so this week Dan and Ian are jumping on the horn to talk about the progress that they've made with their remote jobs business Dynamite Jobs. Since the start of the summer, we've been building a new software platform designed to make the hiring process a whole lot easier for entrepreneurs. Just a few weeks ago, we finally started onboarding users into the platform. So far the results have been remarkable, but the challenges immense. In today's episode, we're sharing four specific things that we've learned from creating a brand new software product. You'll hear updates about some key figures in our business, how running a SaaS business has differed from a lot of our other ventures, and a whole lot more.

For our money, there is nobody quite like Kevin Kelly. Not only is he one of the co-founders of Wired Magazine, but he is also the author of some of our favorite pieces of writing about technology, including What Technology Wants, New Rules for the New Economy, and the brilliant essay 1,000 True Fans, which has been discussed countless times on this show over the years. This week, Kevin is joining us for a conversation about technology and how it informs our lives and businesses. On this podcast, Kevin shares his thoughts about why we have to stretch our imaginations more, what we can learn about technology from the Amish, why you should focus on "Being the only", and so much more.

Today's podcast is all about one listener of this show who took the concept of productizing and applied it incredibly well at a very high velocity. More than that, it's a story about endurance, applying systems intelligently, and the power of community. Ian Horley left a long stint at a successful corporate job in 2014 to create his own web agency, but he ultimately found himself incredibly stressed and unhappy. Today, Ian is the founder of HubSnacks, a productized service which offers unlimited tasks on the HubSpot platform for a fixed monthly fee. In this week's episode, Ian joins us to recall his tale of leaving the corporate world, why he struggled with the day-to-day of running an agency, and how productizing has finally allowed him the freedom to create a business on his own terms.

Longtime listeners know that this is typically the time of year that we host DC BKK, our annual Dynamite Circle event in Bangkok. Each year, hundreds of entrepreneurs flock to the capital city of Thailand for the chance to meet and share ideas with like-minded people from across the globe. This has always been sort of a magical time for so many of us in the community, and to say that we are disappointed that we can't take part in it this year would be a huge understatement. It has become something of a tradition that our good friend Jeff Pecaro sits down with us after the event to crack open a beer and talk shop. Jeff is an incredibly talented copywriter and the founder of MostlyStories.com. He is also the man behind the content at most of our in-person events. This year, Jeff is joining us virtually on the podcast to commiserate and share some of our favorite memories, thoughts, and insights into the history of DCBKK.

It goes without saying that as internet entrepreneurs, we are fascinated by the future of money, and it's hard to talk about the future of money without talking about cryptocurrency. Greg Gerber is our go-to guy when it comes to simplifying the complicated world of crypto. We've invited Greg back on to the show this week to talk about the state of crypto in 2020. As this conversation unfolds, you'll hear about the philosophical differences between Bitcoin and Ethereum, the emerging lending industry in the crypto space, and how Greg hopes to help more people go down the crypto rabbit hole with his newest venture, BitLift. Disclaimer: These are just our opinions, and are presented for informational purposes only. They are not intended to be considered as financial advice.

We've been devoting a lot of time to talking about software businesses in recent weeks. One of the reasons we are so fascinated by them is that despite how difficult it can be to start one, these types of businesses can have tremendous upside. Jordan Gal is the founder of CartHook, a software company that helps Shopify merchants present offers to shoppers at checkout. Jordan first reached out to us back in 2015 with an investment opportunity (and we turned him down!). It really shouldn't come as a surprise then that Carthook has grown exponentially in the years since, with its user base having made more than a billion dollars worth of sales. Jordan joins us on today's podcast to share the story of CartHook.

Today's episode is all about software startups, and there are very few people more capable or qualified to talk about them than today's guest. Simon Payne first joined us on this podcast back in 2016 to talk about his role as the technical co-founder of Leadpages. Since leaving Leadpages in 2016, Simon has gone on to found multiple software companies, including a video tool called Convert Player, and a ticketing tool that we regularly use in our own business called EventsFrame. But, as you will hear on today's podcast, the results of these endeavors have ultimately been a mixed bag. Simon joins us this week to share the details of his entrepreneurial journey over the last few years, to discuss how the relationships between developers and marketers can make or break a software business, and to explain why he's recently decided to help us build our own software platform at Dynamite Jobs.

Today's episode features a longtime friend and mentor who shared an idea with us many years ago that changed the way that we thought about entrepreneurship. David McKeegan and his wife Carrie are the founders of Greenback Expat Tax Services. David first joined us on the podcast back in 2013, and he is singlehandedly responsible for introducing us to one of our all-time favorite concepts, The 1,000 Day Principle. This idea that it takes 1,000 days of full-time effort to replace the income from your day job has since been dissected on this podcast countless times over the years. David joins us this week to fill us in on the many developments in his business, to share his personal tale of an entrepreneurial identity crisis, and to discuss the lasting legacy of The 1,000 Day Principle.

We talk quite a bit on this podcast about services businesses and the sorts of problems that they seek to solve for their customers. You may recall that Eagan Heath joined us to share his thoughts about this back in 2018 on an episode titled "The Knowledge Gap vs. The Efficiency Gap Revisited". In that episode, we spoke about whether it is better to serve your customers by filling a "knowledge gap" and teaching them why they need your services or to fill an "efficiency gap" by helping them optimize something that they are already doing. Since then, Eagan and his team have decided to move on from filling "knowledge gaps" for local businesses in Wisconsin and to focus on servicing "efficiency gaps" by providing digital marketing services to eCommerce businesses with his new company Caravan Digital. Eagan joins us this week to share the reasons he's chosen to change his approach to this philosophy and why he feels like the "efficiency gap" strategy has ultimately prevailed.

One of the promises of entrepreneurship is that there are opportunities to make money all around us if we can learn how to recognize them. Laurence Taylor has recognized some of them himself. Laurence and his wife are the founders of HipTen, a SwaS (Software with a Service) consultancy that works exclusively on the Salesforce platform for the insurance industry. Prior to getting into that niche, they were struggling, as many small startups do, to find their place in the market. Laurence joins us today to talk about the pros and cons of SwaS startups, what it's like working with your spouse, how they saw an opportunity work in the insurance industry, and much more.

We love hearing from listeners of this show. We put out the call a few weeks ago for listeners to send us your stories, and you responded to us in abundance. Our mailbox has been positively chock full of listener voicemails about all kinds of topics. In today's episode, we'll be listening to several of those voicemails and weighing in with our own thoughts and observations. The topics range from how much location really matters, why hustle is the ultimate entrepreneurial muscle, the value of being an "intrapreneur", and love in the age of COVID.

One of our favorite things about this podcast is that we get to talk to people who have inspired us and entertained us over the years. Matt Farah is certainly one of those people. Matt is somewhat of a pioneer in the automotive journalism community on the internet. His long-running YouTube channel The Smoking Tire and his podcast of the same name are both incredibly popular, and among our very favorites. Matt was gracious enough to talk to us on this podcast back in 2016 about breaking through on YouTube, and since we last spoke to Matt a lot has changed in his life. Matt joins us today to talk about how his YouTube channel and podcast have grown over the last four years, and why he is choosing to diversify the money that he earned on YouTube into a somewhat unorthodox brick-and-mortar investment.

A few weeks ago on this podcast, we mentioned that we had started writing a new book based around The 1,000 Day Principle, a recurring topic we've talked about many times on this podcast. In doing research for that book, a few common themes have started to become apparent to us. There are several different paths to becoming wealthy, some of which follow traditional social norms, and others exist in the fringes of society that many listeners of this show might find themselves in. On today's podcast, we are discussing three specific strategies for acquiring wealth that we have come across time and again. These are by no means the only ways to become wealthy, but they are three of the most common methods that we have seen people use to get there. Stick around to the end of the episode to hear some thoughtful and funny listener messages we received in response to last week’s call for ‘Coronavirus related stories’, including one listener who shares the very real challenges of working from home with small children.

As the dog days of summer are coming to a close, we've decided to address several interesting topics that have come across our desk throughout the month of August. One such topic came in the form of an article by entrepreneur and author James Altucher, who discussed why he thinks ‘NYC is dead forever’. He argues that COVID-19’s effects on the business and social dynamics of New York are so far-reaching that the city will never recover. But we see it a bit differently - less as a terminal decline and more as an opportunity for reinvention. We'll also be discussing some fundamental issues that we are seeing some remote job seekers face now that so-called ‘digital nomads’ have had their wings clipped. Finally, you'll hear some of our thoughts on the "new normal" and what the future might look like for digital nomads in the wake of COVID-19.

In past episodes, we've talked about "Founder Fit", or the idea that you should be running the type of business that is best suited to your own personality and lifestyle. But what happens if you're not doing that? It turns out that having a bad fit between you and what you're building can potentially lead to a whole lot of pain. Jesse Hanley is all too familiar with this experience. Jesse is the founder of an agency called TalentTree, and he recently made the decision to shift the focus of his agency to a productized service model in order to fund the development and growth of his new software company Bento. Jesse joins us this week to share the emotional toll he experienced running that agency, why he decided to make drastic changes to his business to improve his quality of life, and how he has been able to find a large portion of his clientele on a rather unexpected platform.