Tropical MBA: Entrepreneurship & Founder Lifestyle

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.

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.

On today's podcast, we are sharing some personal updates, as well as three specific updates about our core businesses. We are also announcing that for the first time in nearly five years, we are hiring a Community Facilitator for our private membership group The Dynamite Circle. Later on in the episode, we'll be exploring the idea of the moment in a business that Seth Godin refers to as "The Dip". You'll hear why this "middle period" of running a business is so difficult, how it feels to be in that dip, and why so many people just can't get out of it.

Productized services have long been a subject of discussion on this podcast. They are a relatively attractive business model, especially among first-time entrepreneurs, and we've shared many examples over the years of how to create these kinds of businesses and scale them. Meryl Johnston, founder of the online bookkeeping firm Bean Ninjas, recently started a rather lively debate in the members' forum of our online community The Dynamite Circle with a post titled, ‘Are Productized Services Overrated?’ We've invited Meryl on to the show to find out why she decided to raise that question and to hear her thoughts on a business model that she has personally followed for the last five years. Meryl joins us today to discuss what a productized service really is, the strengths and weaknesses of the model, and why she's wondering whether her own company needs to evolve past it.

Christopher Gimmer is the Co-Founder and CEO of Snappa, a SaaS (Software as a Service) business that allows users to create online graphics quickly and easily. Christopher caught our attention recently when he opened up with a post on Twitter about the emotional cost of being an entrepreneur. We invited Christopher onto the podcast this week to discuss his own journey as an entrepreneur, how difficult it can be for entrepreneurs to find and maintain what he calls "a healthy equilibrium", and how he works to achieve his own balance. You'll also hear why Christopher feels that having a business partner has been key to Snappa’s eventual success and what he sees as the pros and cons of SaaS businesses.

It started with an innocuous-looking image of a yellow aeroplane and ended with a number of threatening letters from a law firm on behalf of the travel site Expedia. In today’s episode, we bring you the denouement of the story of why we decided to remove ‘that plane’ from our branding. And, to find out whether we really needed to do it, we’ve invited back our good friend and Intellectual Property (IP) attorney Sarah Kornblet Waldbuesser from Destination Legal. You'll also hear Sarah's thoughts on the best way to protect your brand or logo, how to differentiate between "trademark scams" and what should be taken seriously, and a whole lot more.

On today's podcast, we're excited to finally reveal that our remote jobs platform Dynamite Jobs is officially a ".com business". After three years of running the company with a .co domain, that .com marks a huge symbolic change for our company, but it didn't come cheap. Enter Rob Barbour of DomainSOS.com and DomainVIP.com. Rob has worked in the domain space for over twenty years and he owns a substantial portfolio of his own domains. He also specializes in helping people acquire domains that are difficult to obtain. In this week's podcast, Rob joins us to talk about his history as a domain broker, how the industry has changed over 20 years, and how he helped us secure DynamiteJobs.com for our business.

If we had to pick one word as our greatest motivation, it’s ‘freedom’. Freedom to live life on our terms, where we want, with the people we choose. Ali Marsland is the director of ‘The Effective English Company’. Ali began chasing her own freedom at the age of 18, as she traveled around the world for a year before embarking on a successful career in corporate communications. The corporate world eventually made her feel trapped, and when the opportunity arose to become a freelancer, she decided to chase that freedom once more. Ali joins us on this week's podcast to describe how she ‘stair-stepped’ her way into entrepreneurship by first becoming an on-site freelancer to outsourcing work, and eventually growing her own successful agency.