

Geroy Simon: Navigating NIL, Check Your Ego as a Coach & It Always Comes Back to the Child
Episode notes
Geroy Simon is one of the most decorated players in CFL history: three Grey Cup victories, a Most Outstanding Player award, and a place in the Canadian Football Hall of Fame. Since retiring, he's built a front-office career that's taken him from scouting to the CFL front office and now back to where it started: Executive Director of Revenue Share and General Manager at his alma mater, the University of Maryland.
He's also a father of four with very different journeys through sport: sons who played college football at West Point and in Canada, daughters who pursued gymnastics and their own paths. Combine that with his career, and he's sat in multiple chairs around the recruiting table.
Geroy and Scott dig into recruiting in the NIL and transfer-portal era, the difference between coaching other people's kids and coaching his own son, why he wants his kids to experience real failure, and the lessons his parents and grandmothers imprinted on him that still guide how he talks to student athletes today. Geroy also tells the story of a player nobody expected much from who's still in football today, and opens up about the toughest stretch of his own career: getting cut seven times in two years before Winnipeg gave him a second chance.
Chapters:
0:00 Opening
1:35 Introducing Geroy Simon
3:12 Being Recruited by Maryland, Then and Now
5:30 The Other Side of the Recruiting Desk
6:18 How NIL Has Changed Recruiting
7:44 Transactional vs. Transformational Athletes
9:23 His Son's Choice: West Point Over the Ivy League
12:50 The Pressure of Carrying the Simon Name
14:12 Coaching His Own Son
17:21 Checking His Ego as a Youth Coach
19:16 His Daughters' Sports Experience
20:11 The Real Impact of Youth Sports on His Kids
21:37 Growing Up a Multi-Sport Athlete
23:39 Is Year-Round Specialization Hurting Kids?
25:29 Why Football Was the Right Fit
27:26 What Made His Love for the Game Endure
32:45 Lessons His Parents Imprinted on Him
34:39 Control What You Can Control
37:16 Giving Back: Lessons From His Grandmothers
38:40 How Family Dynamics Affect Recruiting
40:08 Has He Ever Walked Away From a Recruit?
41:01 Advice for Overly Involved Parents
42:32 NIL, the Transfer Portal, and Free Agency Culture
44:28 Building Culture in the Transfer Portal Era
47:14 Is This Bleeding Into Youth Sports?
49:19 Wanting His Own Daughters to Fail
51:37 How Great Coaches Make Every Player Feel Valued
53:18 Meeting Every Kid's Different "Why"
58:34 Comparison Culture and Highlight Reels
1:01:19 Educating Athletes on Gambling and Money
1:07:00 The Number One Issue in Youth Sports Today
1:08:06 Cut Seven Times: His Toughest Stretch
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