Tropical MBA: Entrepreneurship & Founder Lifestyle

On today’s show, GrowthHit’s Jim Huffman talks to Dan about the pros and cons of running a successful agency, and how he’s recently been encouraging and enabling his team to create new products via an internal ‘startup studio incubator’. Interestingly, he’s done this, in part, to incentivise people, and offer a creative and rewarding work environment in this increasing competitive job market: “It’s potentially a path to allow really good team players and employees to make their own decisions and part carve their own path within a company, maybe without taking on some of that initial risk .. how can you create this hybrid that meets those people where they're like, ‘Hey, I want to work remote, I want to like do my own thing, but I'm down to have this structure’. It's like, ‘Ok, we need the agency work to get done. But we have a budget to allocate if you have a good idea and if that becomes something, then you have a significant stake in it.”

‘Side hustles’ are a long running theme on this show: those ‘weekends and evenings’ projects that many entrepreneurs have in their back pockets. Many don’t work out but when one does, it’s a great opportunity to run with something which has the possibility to evolve to the next level. But how do you decide when that tipping point is? In today’s show Ben Dowling joins Dan to describe how coding a simple API, to solve a problem he was experiencing while working as the CTO of Calm, lead him to found a Software as a Service called IPinfo, which create datasets about IP addresses: “So many projects I shipped .. felt sort of uphill pushes. And some of them had some moderate success, but it was always an effort. Whereas IPinfo, the traction was sort of straightaway .. And so I think if people are struggling with a project, ‘Hey, do I just need to keep working hard on it?’ It may be best to try something different .. I had no expectations for IPinfo .. but it very quickly sort of started going in that direction”.

Back by popular demand, Dan and Kyla Gardner blow the dust off their bookshelves, and fire up their Kindle and Audible libraries to share some of their favorite recent reads. In this episode, they’ll be talking about what sustained them through the long months of COVID containment. And Kyla also shares her experiences of writing fiction under her pen name Kyla Sharp. “There are so many people making so much money from fiction. Obviously, anyone can self publish, so it has a bad rap and there's a lot of junk out there. But sometimes you can't tell the quality difference because people hire professional editors, they get professional cover designers. They run it through their readers to make sure everything makes sense and they don't have typos. And then they self publish it and they get 70% of those royalties from Amazon instead of traditional publishing where you have to pay back your advance and you might be getting something like 5%”.

Affiliate Marketing businesses have been around way longer than this podcast, and it’s a model that receives its fair share of criticism, especially of those selling ‘courses on how to sell courses’ on the subject. However, one thing is for sure: thousands of entrepreneurs continue to support their families from income generated by affiliate marketing. On today’s show Dan talks with Niche Site Project’s Doug Cunnington about how the model has changed since the early 2000s, ways to seek out good niches and why, even if affiliate marketing isn’t your end-goal, it can be a great place to start: “For example, if you start a niche site, and you're not sure if it's going to work out .. you learn about setting up a website, you learn about keyword research .. and all these different skills that can be really helpful in the future. You may figure out that you're really good at hiring writers, and managing them. And that could turn into a whole different business.”

The ‘AntiWork Movement’ has been with us for decades but, through the pandemic, it’s gained a new traction over at the online discussion forum ‘Reddit’, where the r/antiwork subreddit group (slogan: “Unemployment for all, not just the rich!”) has over 1.7 million subscribers. Just recently, a controversial media interview by one of the moderators caused the thread to be temporarily locked. Today Dan and Ian discuss why, in some ways, they’re sympathetic to some of the AntiWork Movement’s points but not necessary the ways they go about addressing them: “We have a lot of the same founding premises, maybe in 2007/2008 timeframe, we'd say, ‘Hey, we're gonna quit our jobs and start a lifestyle business because we don't want to be subjected to the poor outcomes, and the poor treatment, a lot of the American workforce sees. But also, we saw a changing tide in technology and globalisation, and a necessity to employ a new strategy to be able to achieve wealth and freedom in this new environment”.

Tiny Seed co-founder Rob Walling joins Dan to share insights about why bootstrapped businesses, particularly Software as a Service (SaaS), are becoming increasingly desirable to investors, partly due to the ‘downside protection’ they offer. They also discuss the pros and cons of serving ‘two sided marketplaces’ and why Rob has recently updated his ‘Stair Step Approach’ to entrepreneurship: “One thing that has changed is that there are a lot more opportunities to do ‘step one’ businesses that are recurring revenue from the start, like Shopify add ons .. If there's already a marketplace in place, it takes a huge amount of complexity off your plate .. it allows you to build the business and then learn the other stuff as you go.”

In this week’s episode Dan and Ian respond to some listener questions, thoughts and comments, including: managing relationships within a team as it grows larger, some updates about Dynamite Jobs, and what’s involved in running masterminds and creating a community: “It's a really bad idea to copy something that's already successful but not copy what they did in the early days to be successful. When we talk about conception, we talk about what value it delivers to a small number of people today … and that value proposition is going to be clear to me on day one, so you got to start with a clear conception”.

Productized or Software as a Service? A hot topic often discussed on TMBA. Of course, there’s no right or wrong answer but on today’s show Brian Casel talks to Dan about the factors that contributed to him changing from one to the other by selling Audience Ops and starting ZipMessage and also the different challenges of the two: “With a productized service, it really was much more about the processes. And building a service that is highly repeatable … but in a SaaS, it's less about process, it's just much more about building. And every single month there's something new. It’s not only just building new features, but what's the next marketing channel that I can try to tap into and unlock a new pocket of customers.” You’ll also hear about Brian’s decision to take funding this time around, having always bootstrapped before and selling Audience Ops without using a broker. Plus, And the return of one our favorite participation games - ‘donate a business idea’.

For our first episode of the New Year Dan talks to one of our favorite writers in the investment space, Sam Dogen, author of Financial Samurai. Started in 2009, just as he was trying to dig his way out of losing 35% of his net worth due to the global financial crisis, Sam has been discussing investment strategies on his blog ever since. But ‘Financial Samurai’ is about so much more than that. In this episode Dan and Sam cover the importance of ‘parlay’ in your career, the downsides of ‘Financial Independence, Retire Early’, how he chooses topics to write about, and much more. “I try to write about stuff people care about. You can write about ‘The Five Best Travel Credit Cards’ but, come on, you just need one or two credit cards. Or you can write about ‘How To Get Paid Full Time While Working Only Two Hours A Day’. I mean, that's so much more interesting.” Disclaimer This episode is a personal discussion, it in no way constitutes financial advice - but you knew that, right?

In today’s show Dan talks to Jake Ryan, CIO of the crypto hedge fund TradeCraft Capital and author of ‘Crypto Asset Investing in the Age of Autonomy’, about why he believes the convergence of cryptocurrency and new technologies is creating a transformational environment as significant as the ‘Information Age’. “What we’ve seen, over the past decade or so, is innovation around automation. And that's been powerful, but it hasn't been transformational. It hasn't altered fundamentally how businesses operate. The last piece of the puzzle really was cryptocurrency, because it allows us to store, process and transfer economic value without human intervention … autonomy is the ultimate competitive advantage”.