Tropical MBA: Entrepreneurship & Founder Lifestyle

Latest Episodes:

TMBA566: Why Do SaaS Businesses Fail? Oct 08, 2020

Show notes

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.

TMBA565: The Origins of the 1,000 Day Principle Oct 01, 2020

Show notes

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.

TMBA564: The Knowledge Gap vs The Efficiency Gap Revisited (Again) Sep 24, 2020

Show notes

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.

TMBA563: How Software With a Service (SwaS) Startups Can Succeed Big in Traditional Industries Sep 17, 2020

Show notes

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.

TMBA562: Mailbag: Freedom, Location, and Love in the Age of COVID Sep 10, 2020

Show notes

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.

TMBA561: The Smoking Tire Sep 03, 2020

Show notes

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.

TMBA560: 3 Strategies for Acquiring Wealth Aug 27, 2020

Show notes

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.

TMBA559: A Summer in Review Aug 20, 2020

Show notes

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.

TMBA558: Are You Running the Wrong Kind of Business? Aug 13, 2020

Show notes

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.

TMBA557: Ascending the Staircase Aug 06, 2020

Show notes

Rob Walling is no stranger to many of the listeners of this show.

Rob is the host of a brilliant podcast called Startups for the Rest of Us, where he has shared stories of entrepreneurial ingenuity and struggle, and many concepts that we have discussed on this show have origins on that podcast.

He is also the co-founder of a conference called MicroConf, which is a community and conference for bootstrap SaaS founders.

After a rather impressive exit with his last startup, Drip, Rob has moved on to his newest project, an accelerator designed for early-stage SaaS startups called TinySeed.

Rob joins us this week to discuss some high-level concepts like the emotional challenges of entrepreneurship, to finer details like finding the right pricing models, and how they decided on the right deal terms for TinySeed companies.

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