From skipping to page 50 of Google and earning $50 a month to helping build one of the most dominant sports media companies on the internet, Tom Weingarten's journey at Overtime is a masterclass in finding opportunity where no one else is looking.

In this episode, Tom pulls back the curtain on how Overtime built a decentralized network of 1,000 filmers worldwide, cracked the code on covering high school athletes before they were stars, and made the bold leap from media company to league owner. If you've ever wondered what it actually takes to build a media empire from scratch — and keep it feeling like a startup at 125 million followers — this one's for you.

Timestamps

0:00 — Intro

0:41 — The Social Media Landscape of 2015: Vine, Facebook & No TikTok

1:46 — How Tom Landed at Overtime for $50/Month (Page 50 of Google)

3:15 — The Original Vision: Building "The Instagram of Sports"

5:01 — Why the "ESPN for the Next Generation" Strategy Actually Worked

7:21 — Covering Zion Before Anyone Else: The High School Athlete Bet

9:14 — Building a 1,000-Person Decentralized Filming Network on the Cheap

12:39 — How Overtime Directs & Trains Its Global Network of Filmers

29:35 — How Publishers Are Trained & Then Let Loose

32:00 — Publisher Burnout, 18-Month Peak, & Why Tom Celebrates People Leaving

35:07 — Manager vs. Creator

37:11 — Embracing Competition: Why Overtime Lets Rivals Into Their Events

40:26 — How Overtime Produces 600 Pieces of Content for Fox/World Cup

42:42 — Mega Media Companies vs. the Individual Creator

55:26 — AI, Brand Voice & the Risk of Losing What Makes Overtime, Overtime

56:25 — Tom's Advice for Breaking Into Sports Media

58:52 — Tyler & Jake Reflect on Overtime's Origin Story

1:07:21 — Outro