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.

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.