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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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What if the real path to success starts by choosing your life first — and trusting the business will rise to support it?
In this episode, Matt & Garrett sit down with Justin Roethlingshoefer, who walked away from a comfortable tech career to build a life aligned with purpose, energy, and lifestyle.
From surfing at sunrise to finding a community that fuels growth, this conversation explores the courage, curiosity, and discipline it takes to design a life you actually want — and then build the business to match it.
We talk about:
- Choosing lifestyle and fulfillment over titles and safety
- Identity shifts when you leave a “successful career” behind
- How curiosity, coaching, and repetition accelerate change
- Balancing discipline with joy, freedom, and play
- The surprising power of environment and community
- Why confidence follows action — not the other way around
This episode is a reminder: you don’t have to sacrifice your life to build success. When you get aligned, success shows up because of how you live — not in spite of it.
159 episodes
