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.

Form: Share your story / sponsor the pod

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The Roadmap for Turning a Skill Into a $1M Business

The Unexpected Downsides of Selling Your Business

Success Without Sacrifice?

Shiny Object Syndrome

The Anti-Agency Agency + High ROI Customer Service Strategies

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)

(00:06:23) Deep Giveaways That Convert

(00:12:31) High Ticket Offers

(00:15:30) Lifestyle Business vs. FIRE Movement

(00:19:07) Masterminds as Money Makers

(00:21:08) The Real Challenge of Parenting?

(00:24:49) Pivots and Resetting the Vision

(00:25:58) Real AI Workflows Founders Are Using

(00:26:31) Clarity, Courage, and Deal-Making

(00:27:45) Nailing Your Best Marketing Channel

(00:29:00) Know Your P&L

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The Roadmap for Turning a Skill Into a $1M Business

The Unexpected Downsides of Selling Your Business

Success Without Sacrifice?

Shiny Object Syndrome

The Anti-Agency Agency + High ROI Customer Service Strategies

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.

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The Roadmap for Turning a Skill Into a $1M Business

The Unexpected Downsides of Selling Your Business

Success Without Sacrifice?

Shiny Object Syndrome

The Anti-Agency Agency + High ROI Customer Service Strategies

Dan shares why most bootstrapped business partnerships go sideways—and what to do if yours already has.

CHAPTERS

(00:00:13) Why This Episode Exists

(00:01:27) The Bootstrapper’s Dilemma

(00:03:07) The Gridlock Problem

(00:04:56) When Life Goals Shift

(00:06:32) The Ownership Trap

(00:08:04) Why Money Makes It Worse

(00:09:14) Identity, Resentment, and Role Confusion

(00:15:24) The Minority Partner Illusion

(00:17:26) Rock Band Rules

(00:26:53) How to Reset a Broken Partnership

(00:27:46) The Ultimate Test

(00:30:15) The Goal: One Plus One Equals More Than Two

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The Roadmap for Turning a Skill Into a $1M Business

The Unexpected Downsides of Selling Your Business

Success Without Sacrifice?

Shiny Object Syndrome

The Anti-Agency Agency + High ROI Customer Service Strategies

This week, Dan goes back to the basics—because that’s where the breakthroughs often live. This might be the single most important episode you listen to, especially if you feel like you’ve hit a plateau.

He lays out the fundamentals of crafting a compelling offer, why most founders avoid doing it, and how your aversion to rejection might be holding you back from growth.

Download Dan's Offer Worksheet

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(00:00:00) – The Biggest Lever Under $300K

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The Roadmap for Turning a Skill Into a $1M Business (https://tropicalmba.com/episodes/7-figure-productized-business)

The Unexpected Downsides of Selling Your Business (https://tropicalmba.com/episodes/exit-founders-disappointed)

Success Without Sacrifice? (https://tropicalmba.com/episodes/success-without-sacrifice)

Shiny Object Syndrome (https://tropicalmba.com/episodes/shiny-object-syndrome)

The Anti-Agency Agency + High ROI Customer Service Strategies (https://tropicalmba.com/episodes/anti-agency-high-roi)

Dan shares a relationship-first strategy for landing bigger deals—no funnels, no ads, just a focused system that’s often more affordable and effective than a social media strategy. He’s joined by agency owner James Feng, who’s using this approach to grow from $300K to $1M.

(Dan's template) The Rolodex Method + Marketing Tracker

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(00:00:00) Intro

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The Roadmap for Turning a Skill Into a $1M Business (https://tropicalmba.com/episodes/7-figure-productized-business)

The Unexpected Downsides of Selling Your Business (https://tropicalmba.com/episodes/exit-founders-disappointed)

Success Without Sacrifice? (https://tropicalmba.com/episodes/success-without-sacrifice)

Shiny Object Syndrome (https://tropicalmba.com/episodes/shiny-object-syndrome)

The Anti-Agency Agency + High ROI Customer Service Strategies (https://tropicalmba.com/episodes/anti-agency-high-roi)

What if your struggle to follow through isn’t a discipline problem — but a signal? This week, Dan unpacks why many entrepreneurs bounce between ideas early on, and how that phase might be necessary, not broken. He shares a simple framework for telling the difference between just another project… and a business worth going all-in on.

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(00:00:13) Intro + Listener Question

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The Roadmap for Turning a Skill Into a $1M Business

The Unexpected Downsides of Selling Your Business

Success Without Sacrifice?

Shiny Object Syndrome

The Anti-Agency Agency + High ROI Customer Service Strategies

Some of the “smart moves” founders make might be signs of hidden resistance. This week, Dan and Ian break down 10 behaviors that can quietly kill momentum, from expanding marketing channels too early to pausing sales during busy stretches. They also dive into why scaling too soon backfires, the hidden risks of declining assets, and what happens when you delay building management layers.

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(00:00:13) Introduction

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The Roadmap for Turning a Skill Into a $1M Business

The Unexpected Downsides of Selling Your Business

Success Without Sacrifice?

Shiny Object Syndrome

The Anti-Agency Agency + High ROI Customer Service Strategies

Dan shares strategies for creating value as an entrepreneur - from maximizing personal productivity to defending your creative space so you can build something meaningful. He breaks down the common roadblocks entrepreneurs face at the $300K revenue mark and shares practical wisdom for navigating difficult personalities in business and in life.

Book recos form the episode:

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Dan and Ian break down what makes a great lifestyle business in 2025—one that delivers both strong cash flow and location freedom. They dive into the nuanced tension between building a lifestyle-friendly business and “going big,” and share five essential design principles for creating a business that supports the life you want.

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