Tropical MBA: Entrepreneurship & Founder Lifestyle

Thinking of selling your business one day? Or never planning to? Either way, this conversation could change how you build. Rob Walling has seen it all. He’s exited his own SaaS company and helped thousands of founders grow and sell through TinySeed, MicroConf, and his podcast “Startups for the Rest of Us.” In this epis

Is the “lifestyle business” still alive in 2025? Dan chats with longtime friend Jeff Pecaro about the evolution of internet business, what today’s solopreneurs get right (and wrong), and how constraints can lead to clarity. They dive into pricing mistakes, the pressure to grow beyond your goals, and how to use tools li

Many founders hit $3M in revenue and stall out. In this episode, Dan and Greg Crabtree break down why—and how to fix it. They discuss “profit truth”, how to spot financial red flags, and what metrics to track to scale beyond the messy middle. Plus: we’re looking for listener stories. Have you implemented a system or fr

What 160 founders taught us at DC Mexico—why deep customer engagement beats ads, how group workshops are replacing sales calls, what lifestyle entrepreneurs can learn from the FIRE movement, and how financial clarity and community still drive the biggest results. CHAPTERS (00:00:34) DC Mexico Recap (00:02:42) Why We Do

Dan shares how advanced digital nomads use geography as a lever for business growth—and why most people get it wrong. If you’re going to travel, do it with intention. This episode breaks down how. CHAPTERS (00:02:00) The Embargo on “Digital Nomad” (00:02:35) Why Most Nomads Miss the Point (00:05:38) 4 Ways to Travel Sm

Dan shares why most bootstrapped business partnerships go sideways—and what to do if yours already has. Resources Mentioned: ● When Partners Fall Out (HBR article) (https://hbr.org/1986/11/when-partners-fall-out) ● Tropical MBA financial dashboards (https://tropicalmba.com/resources) CHAPTERS (00:00:13) Why This Episod