Tropical MBA: Entrepreneurship & Founder Lifestyle

Is it possible to bootstrap a high-level business if you’re broke? Listen to Dan & Ian’s take on what kinds of businesses are best to start when you’re starting with basically nothing. Also, what the hell does a visionary do? Dan suggests that the best visionaries have integrator tendencies. They’ll consider how Kevin

The hard part shouldn’t be how to implement an OS in your organization. The hard part is answering the question: Are the right people in the right roles at your company? In this episode, Dan and Ian share their own OS that’s extremely simple. It’s called GPS. They’ll explain how GPS helps you put a plan in place to mee

In this episode, Ian and Dan discuss the concept of doing things that don't scale, inspired by Paul Graham's influential article 'Do Things That Don't Scale.' They explore the idea of taking risks and gambling in entrepreneurship, and how it relates to increasing one's locus of control. The conversation covers various

Dan and Ian discuss the different phases of bootstrapping a business and the common challenges that arise at each stage. They walk through three phases: Zero to $250k “Mindset”; $250k to 1 million "We're seeking a reliable/repeatable source of new customers"; and $1 million + "We need to hire, fire, improve/change team

Dan talks to Jordan Gal, founder of Rally and co-host of the Bootsrapped Web podcast about challenges in the ecommerce space, product-market fit and demand, partnerships and veto power, the quietness of crypto, risking other people’s money, and more… There’s one thing that founders tend to really struggle with when it

Dan & Ian talk to John Doherty, the founder of Editor Ninja, former owner of Credo, and cohost of the Working Sessions podcast about three major trends he’s seeing in the agency space that could impact your strategy and profitability for the year and beyond. John talks about the challenges of running a full-service age