Building the Most Creative Brand in Sports Media
Sep 21, 2026
Jack Settleman is the founder of Snapback Sports, the sports media company that started as a Snapchat account in 2017 and became one of Underdog's earliest creator partners. Jack breaks down the bets behind the business — taking equity in Underdog before its $1.3 billion sale, deleting a 600,000-subscriber YouTube channel, sending his brother to 33 World Cup games in 39 days, and choosing not to pay himself a salary — plus why he believes the gatekeepers in sports media are running out of time.
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Snapback Sports
- YouTube: @SnapbackSports1
- Website: https://www.snapbacksports.com
- Instagram: https://www.instagram.com/snapbacksports_
- X: https://x.com/snapbacksports
- TikTok: https://www.tiktok.com/@snapbacksports
- Snapchat: https://www.snapchat.com/@snapbacksports
Jack Settleman
- Newsletter: https://jacksettleman.beehiiv.com
- LinkedIn: https://www.linkedin.com/in/jack-settleman-424a73b1/
- X: https://x.com/jacksettleman
- Instagram: https://www.instagram.com/jacksettleman
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Timestamps
00:00 Introducing Jack Settleman of Snapback Sports
00:52 The $1.3B sale
05:59 The origin of Snapback Sports
09:36 Turning a Snapchat page into a real business
12:47 $2M revenue with mostly brand deals
15:30 Remaining unique as a sport media brand
24:32 Ethical boundaries in sports advertising
34:53 Making ambitious unique content
44:30 Pivoting from creator to business owner
48:19 Investing back into the product
56:15 Creating products beyond content
59:30 The many failed Snapback projects
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