Some entrepreneurs chase the money. Others chase the hype.

But the best ones? They build something awesome and build a life they actually want to live.

In this episode, I sit down with Kris Dehnert, the powerhouse behind Dugout Mugs, a wildly creative brand turning baseball bats into drinkware and generating $56M+ in sales along the way. Kris shares how a brush with death became the wake-up call that led him to bet big on a product fans LOVE, and a lifestyle he’s proud to model for his kids.

We go deep on:

Building an empire from a ridiculously cool idea ⚾➡️☕
Why freedom is the most valuable entrepreneurial currency
How to scale without crumbling your systems (or sanity)
Partnerships, pivots, and the power of “If this → then that” decision-making
Selling fun products that actually mean something to the buyer
Why chasing happiness often leads to more money — not less

And yes… we geek out on supply chains, Teespring glory days, Inc. 5000 wins, and what happens when baseball legends start repping your product without being paid a dime.

This episode is for founders who want BOTH:
A business they’re proud of.
And a life they’re excited to wake up to.

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Key Takeaways

Lifestyle by design > Hustle by default
Break systems once — then rebuild RELENTLESSLY for scale
Know your customer better than they know themselves
Momentum loves courage — but systems keep you alive
Happiness is a strategy, not a side effect