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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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In this episode, we break down a powerful idea from Jeffrey Walker, a private equity veteran who backed thousands of entrepreneurs and watched success and failure up close. His conclusion is uncomfortable but freeing: the people who win don’t follow a path, they create one.
You’ll hear why talent is overrated, why “perfect careers” quietly fail, how one pathless founder built a $200M company, and a practical framework for building a career or business that actually compounds over decades.
TIMESTAMPS
0:00 The dangerous myth of “the path”
1:04 Jeffrey Walker’s core insight: there is no path
3:05 Talent is common, intentionality is rare
4:12 The banker assembly line trap
5:53 The perfect resume that led nowhere
7:01 The pathless entrepreneur who built a $200M company
8:34 Sponsor CapitalPad - Curated deal flow. Aligned sponsors. Simplified investing.
9:44 How building your own path changes everything
12:13 A practical framework for creating your own path
14:16 The real takeaway: paths only make sense in hindsight
Sponsors:
https://capitalpad.com/
Follow Mikk/PrivateEquityGuy on Twitter: https://x.com/PrivatEquityGuy
This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.
138 episodes
