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 Kelly’s “100 True Fans” can lead to sustaina

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 meet your goals, and deliver on that plan. That’s it. A

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 strategies for founders, including recru

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 members more effectively”. They explor

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 comes to growing their business and that’s getting the

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 agency, a shift towards specialization in productized servic

Transitioning through the death zone requires careful execution and a focus on profitability. The $3 million dollar mark is a critical milestone for businesses, and many struggle to push through it. In this episode, Dan talks to Greg Crabtree, author of Simple Numbers, Straight Talk, Big Profits! about how founders can push through the death zone (otherwise known as the messy middl

This week Dan & Ian share a few thought experiments you can do to improve your business and reach your next breakthrough. They cover the value of a writing-first culture, the Queen Bee Role & how transparent should you be with your team? Plus, a ticket giveaway to one qualified founder. Dan & Ian’s Stuff: The Newsletter “The DC” DC Black Global events Hire remot

Going deeper on shiny object syndrome, Dan & Ian open the mailbag to read responses to last week’s episode. A listener shares his success story with shiny object syndrome, revealing how he pursues his entrepreneurial impulses without growing crazy. The listener emphasizes the value of muscle memory when it comes to going from zero to one successfully. Dan & Ian will also

Dan & Ian delve into the complexities of combating shiny object syndrome, a challenge that plagues all entrepreneurs at one time or another (or all the time). They’ll talk about six strategies for tackling “the syndrome” and how to harness your skill of going zero-to-one to grow your business to the next level. Dan & Ian’s Stuff: The Newsletter “The DC” DC Bla