From Childhood Best Friends to Top of their Fields with Greg Genske
August 18, 2026
AI Summary
5 min readFrom Childhood Friends to Top of Their Fields
When Ed Mylett sat down with Greg Genske, it marked the first time in 35 years the two childhood best friends had been in the same room. They grew up inseparable—playing wiffle ball, running track at six in the morning during summer breaks, trading baseball cards (Genske consistently won those trades). Then life pulled them apart. Mylett went into personal development and entrepreneurship. Genske became one of the most successful sports agents on the planet, negotiating over $6 billion in deals, teaching negotiation at Berkeley Law, and now serving as CEO of Vayner Baseball alongside Gary Vaynerchuk.
The Unlikely Path to Sports Representation
Genske didn't set out to be a sports agent. He was a business major at Pepperdine when a late-night viewing of A Few Good Men sparked something. Watching Tom Cruise and Kevin Bacon compete in a courtroom, he thought: "I can have a career where I get to compete on that stage." He decided on the spot to become a trial lawyer.
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What you'll learn
- 1 (00:00) **Advertisements** - Exxon Mobile Rewards Plus and First Citizens Bank / Silicon Valley Bank commercials.
- 2 (01:05) **Childhood Reunion and Introduction** - Ed Mylett introduces his childhood best friend, Greg Genske, whom he hasn't seen in 35 years.
- 3 (09:39) **Origin Story: From Trial Lawyer to Sports Agent** - Genske explains how a pivotal legal case led him to abandon a successful law career to enter the sports world.
- 4 (14:38) **Advertisements** - ButcherBox and Ro (weight loss treatment) commercials.
- 5 (16:39) **The Gutsy Pivot and Following Breadcrumbs** - Genske discusses the mindset required to leave a successful career for an uncertain new path.
- 6 (19:08) **The Drew Bledsoe Deposition That Changed NFL History** - Genske reveals how his cross-examination of Drew Bledsoe exposed a vulnerable contract, potentially enabling Tom Brady's rise.
- 7 (22:44) **Negotiation Masterclass: Psychology and Preparation** - Genske shares the foundational principles of negotiation he teaches at Berkeley Law.
+ Full timestamped outline available in the app
Guests on this episode
Show Notes
Before you have a business or a following, you have a friend. Mine grew up to negotiate six billion dollars in sports contracts.
This episode is different for me. My guest was my best friend when we were ten years old, inseparable, running track together at six in the morning, trading baseball cards, growing up right alongside each other. Then life happened, and thirty five years went by without us being in the same room. After all that time, we finally sat down together, and today I brought him on the show.
Greg Genske went from that kid in my backyard to one of the top sports agents alive, building an agency with Gary Vaynerchuk, teaching negotiation at Berkeley Law, and representing thousands of professional athletes through the biggest deals of their careers.
Here's what you'll gain from this episode:
- The Negotiation Secret Nobody Teaches: Greg breaks down the psychology of negotiation and why immaculate preparation on the other person's position beats any tactic.
- The Tom Brady Story You've Never Heard: How a single deposition Greg took as a trial lawyer helped open the door for the greatest quarterback in history.
- Position Yourself as the Expert: Why the people who separate themselves in any industry teach instead of sell.
- Elimination, Not Addition: Greg's decision to give up alcohol after nine years of winning in spite of it, and what he found on the other side.
- What 3,000 Athletes Taught Him About Loyalty: The difference between being an agent and being a real partner.
If you've got a friend from your childhood you've lost touch with, this one is your sign to reach out today. Some relationships are worth thirty five years of silence and still worth fighting for.
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