Dan and Ian respond to a series of spicy "unpopular opinions" about entrepreneurship, employment, digital nomadism, and lifestyle design, sourced straight from Reddit. They weigh in on whether boring businesses really win, if you can get rich working a 9-to-5, and whether meeting locals is overrated when traveling as a nomad. LINKS: 22 FREE busines…

We’re halfway through 2025! This episode is a raw look at what’s working, what’s not, and the experiments we’re doubling down on. From running premium events at zero profit to building lean teams with talent from Latin America, we share the trade-offs and results behind every decision. Dan and Ian open the books on DC BLACK and DC Accelerator, plus…

What happens when you’ve optimized everything… and growth still stalls? In this episode, Dan and Ian break down a powerful distinction most founders miss: the difference between optimization (making your business run smoother) and growth (finding and testing new paths to scale). They unpack insights from Growth Levers by Matt Lerner, a framework th…

What marketing strategies are actually working in 2025? Karla Singson shares standout tactics from a DC Mexico meetup she hosted, where 6- and 7-figure founders revealed how they’re landing clients organically through Facebook groups, trade show podcast hacks, and thoughtful LinkedIn comments (no ad spend required). We also dive into Karla’s own pl…

From hating life on a Sydney construction site to building a $57K/month agency from Bali, Tom Richards—founder of PlumbElec Marketing—has lived the remote founder arc. In this episode, he shares how niching into plumbing and electrical businesses helped him scale fast, why Google Maps still dominates local SEO, and how he balances agency life with …

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 episode, he sits down with Dan to …

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 like AI to think—not just automa…

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 framework that changed your busi…

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 This (Essay by Jeff Pecaro) (…

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 Smart and Build Faster (00:06:13…