Tropical MBA: Entrepreneurship & Founder Lifestyle

It’s an evolving economic landscape out there: interest rates are up, high paying tech jobs are down. One bank has collapsed and crypto doesn’t seem to be the panacea that some wished. On this week’s show we’re talking investing - the opportunities, possible pitfalls and safe bets. Travis Jamison is founder of the SEO agency Smash Digital, and also owns an e-commerce supplement brand. But in recent times, through his newsletter and online community Investing.io, he’s been focusing on investing in other online business opportunities and also assets like stocks and crypto. He talks to Dan about where he’s currently putting his money and who he sees as the winners and losers in the current economic situation. “Cash gives you optionality. People like to say that it allows you to buy deals when things are cheap. That's definitely true … but it also keeps people from making bad decisions. Liquidity is everything. You don't want to be forced to sell, especially when stuff is really bad. That's the worst time to sell. So keeping a cash, a heavy cash position, can just help you wait out the dips without the bad times and just stay invested in compounding over the long term. That's how you win over time.”

The story of how Property Hub, now a multi-7 figure online community and real estate acquisition and management business, was built from a podcast, a book, and a strategy of abundance. When Rob Dix started co-hosting The Property Podcast a decade ago he had no idea of the traction it was getting until they announced their first ‘in person meet-up’ for listeners and hundreds of people showed up. Today the show is downloaded by 400,000 each week. Rob Dix talks to Dan about the reasons he continues to create most of Property Hub’s content himself, and the schedule he uses to achieve it. They also discuss why Rob decided to sign a two book deal with a major publisher and why he believes their ultimate ‘competitive advantage’ is ‘giving more away for free than anyone else’.

The first quarter of the year has been volatile for many large US-based tech companies, with thousands of staff layoffs. Inflation and the collapse of Silicon Valley Bank have added to the sense of uncertainty. Yet, through all of this. bootstrapped businesses have proved remarkably resilient. On this week’s show Dan talks to Tiny Seed founder Rob Walling about how the economies of running smaller online businesses enable them to be nimble and resourceful in all circumstances. They also discuss Rob’s forthcoming book The SaaS Playbook, what it takes to build a Unicorn (and do you want to go there?) and the potential impact of AI: “It’s both over-hyped and under-hyped. Just like I think the Web was and just like I think with Web3, and crypto and blockchain … (they’re) not dead. Like I hear people saying, ‘Is crypto even worth anything anymore?’ It's still a thing. And I don't just mean Bitcoin as a currency but the idea of a blockchain, these have applications that will carry on. That's how I think of AI. I think if I was an employee today, or I was doing low skilled work, I would be shaking in my boots. For smart entrepreneurs, it is much like offshoring was - being able to hire a developer in the Philippines in 2009 changed the way I could operate business. I think AI is the same”.

The ‘Money Theory of Location’ argues that calculating 4x the average salary in the place you choose to live, whether that’s Mexico City, or Bangkok, or New York is a good indication for the amount of money you’ll need to achieve a great standard of living there, and a lot of potential for freedom in your life.. On this week’s show Dan and Ian talk location arbitrage, including their regrets about moving to San Diego and not San Francisco when they were straight out of college: “There's a little bit of naivete, a lot of naivete, in a 21-year old Dan saying, ‘Just because California is a state with opportunities, because there's a lot of big houses there and stuff, that that means that that has anything to do with you’. You have to decide what you're doing, and how that would align up with that small tribe of people that are doing those things, and where those people are”. They also offer some thoughts to a listener who has moved his freelancers to full time contracts. He’s seeing some decrease in productivity and is wondering what to do about it.

How one entrepreneur has achieved huge growth in his business by ditching the low-cost ‘productized service’ model and pursuing upmarket enterprise clients. That person is Harry Morton, founder of the podcast production service Lower Street. Harry talks to Dan about how pivoting has allowed him to reach a low to mid seven figure annual revenue, and grow a team of over 20. They discuss why building a network and evolving a strong company culture has been so crucial, the importance of getting a grip on your financials, how accepting who you are and what drives you is crucial, and the challenges and opportunities afforded by AI: ‘I think that while AI is coming for all of our lunches it's coming for the productised end first because you have a very clearly defined list of deliverables and you point Chat GPT or whatever at it and it's not going to take too long, I don't think, for that to catch up and make the make the drop the price even further. So I think for anyone in an agency business, certainly something I spend a lot of time thinking about is: How is AI going to affect us? How do we incorporate AI? How do we embrace it?’

Today Dan and Ian reflect on some of the key observations they’ve taken away from calls with over 50 business owners during the launch of their implementation program ‘DC Scale’. And, this being the TMBA, there are 5 categories: ‘The $500K Stall’, ‘The Solo Recording Artist Mentality’, ‘Pulling Punches’, ‘Grade A at Hiring But Grade B at Managing’ and ‘The Cloak of Invisibility’: ‘Even today, when there are more people to follow then followers, and everybody's a brand … Most of these entrepreneurs are just not brands. And they really don't need to be. The vast majority of people we spoke with have a personal network, they are using channels like events, industry contacts, and referrals to bring in the key relationships that they need in their business. They're not necessarily using internet marketing funnels to bring in customers’. Dan and Ian also give their take on how and why the ‘Visionary vs Integrator’ definitions came about, and how useful they are, and share thoughts on the pros and cons of the ‘4 Day Work Week’.

The story of Going touches on so many themes we’ve been following on this show for over a decade. Going’s original incarnation, ’Scott’s Cheap Flights’, came on the scene in 2013. And it started out mostly as a newsletter for digital nomads seeking the most cost effective ways to travel around the world, nerd out on ‘mistake fares’ by airlines, and other things of interest in the travel space. Today Going has over 60 employees and is a very substantial business, offering a range of options to its subscribers. On this week’s show Brian Kidwell talks to Dan about his personal journey from solopreneur to CEO of Going, the challenges of making that transition, the importance of seeking product market in whatever you’re working on, and finding time for ‘deep work’: “How can I have enough hours in the day to give the proper thinking, my best thinking, to the things that I need to work on? Because those things now have much more downstream impacts than before. It's like editing code, or responding to somebody - and I'm not trying to downplay them, because those are very important - but it was different for my brain … Now I can't work as long as I used to … I can't provide great thinking for 12 hours a day.”

TMBA has followed Tommy Griffith’s story for nearly a decade, watching his ‘dorky’ side-hustle teaching weekend SEO classes evolve into ClickMinded, a substantial online education portfolio. On today’s show Tommy talks to Dan about how ClickMinded has evolved further, with the help of a new CEO, to a white label documentation provider which turned over $2.3M last year. And he reflects on why he seems to have taken almost every ‘incredibly difficult and complicated option’ to get to where ClickMinded is today: “I think it was arrogance. We had this idea that we were an Ed tech company, that we were creating these online courses. I think there was also some sunk cost fallacy going on. I mean, we had 85 hours of HD videos, seven instructors, and some universities were using our courses … The product was great, we were super proud of it, and it took a lot of work to do. So the fact that people were saying, ‘Actually, can I just pay for all of these Google Docs’. It was a little hard to face that music.”

When starting a business or advancing your career, or even just seeking to increase your public profile, it’s a savvy move to build momentum through content, and specifically by focusing on a particular channel. Today’s guest is an expert at doing just that. Steph Smith is the author of ‘Doing Content Right’. She’s also the host of the a16z podcast and ‘The Sh*t You Don’t Learn in School’. Steph talks to Dan about the opportunities being a creator opens up, tips on how to choose the right channel for what you’re trying to achieve, and why being data driven is so fundamental to achieving growth: “If you are doing a good job with growth, data should rule the day. You should be able to clearly say, ‘here's an aspect of our funnel that we want to run a test on, because we believe it has this upside’. And you run the test …. I've gone on to other companies that were way less data driven. That's honestly something that I really struggle with because when you are in situations where you are having to kind of say, ‘hey, let's do this project, I think it'll maybe have some impact’. It's just not compelling to me. I think most things at a company should be pretty data driven”.

Today's guest has been massively influential on Dan and Ian from the very start of their journey. Seth Godin is something of a legend in entrepreneurial circles, and he hardly needs an introduction.His books about marketing, creativity, building companies and personal development include Purple Cow, Meatball Sundae, The Dip, and Linchpin. They are frequent recommendations on this podcast and have long been shared among our listeners. In addition, Seth has founded an intensive four-week alternative online MBA called altMBA. He has also created several podcasts including the popular Startup School and Akimbo. Today's show features a wide-ranging interview, which touches on a variety of topics including Seth's history as a writer and podcaster, what the business world can offer society and much more.