Tropical MBA: Entrepreneurship & Founder Lifestyle

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.

Greg Gerber, a cryptocurrency expert known for making complex topics accessible, joins the discussion on the current state of crypto. He delves into the philosophical distinctions between Bitcoin and Ethereum, shedding light on their roles in transactions and investments. The conversation highlights the burgeoning crypto lending market and potential passive income opportunities. Greg also shares insights on his new venture, BitLift, aimed at helping entrepreneurs navigate the evolving landscape of digital currencies.

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.