AI Summary
5 min read“I got the email.” That’s how Nick remembers the moment his college lacrosse career seemed to end. He had walked onto the Middlebury team as a freshman, a big deal for a program that had won national championships. Then sophomore year, an email arrived: no room for him on the team. The rejection stung, but instead of accepting it, Nick did something almost unheard of. He decided to transfer to a Division I school. He got into Brown, emailed the coach, and was told there was no space for him there either. He showed up on campus anyway. The coach let him practice but wouldn’t let him wear Brown gear. For two months, Nick was a body in a practice pinny, the guy on the sideline. Then, one week before the season, the coach stopped the locker room, pointed to a jersey with Nick’s number on it, and offered him a spot—on one condition: he had to switch from short stick to long stick. Nick grabbed the long stick. He ended up winning an Ivy League championship at Brown, making him, as he puts it, “the only player to win a championship in D3 and D1.” The takeaway he lands on: “Bet on yourself to bet on another person.” He bet on himself by transferring, but the furthest he got came from having someone with him—his co-founder Jack, and later, the right partner in life.
The deal that fell apart
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What you'll learn
- 1 (00:00) **Episode Kickoff & The Comeback Hall of Fame** - Nick and Jack introduce the hotline theme: personal, company, and listener comeback stories.
- 2 (08:08) **Nick's Comeback: Cut from D3 Lacrosse to D1 Champion** - Nick describes being cut from the Middlebury lacrosse team via email and his unlikely path to playing at Brown.
- 3 (12:14) **Jack's Comeback: A Broken Relationship to a Supportive Partner** - Jack shares how a bad breakup and unsupportive ex-girlfriend led him to his wife, Alex, who accelerated his entrepreneurial drive.
- 4 (19:12) **The Company Comeback: A Lost Newsletter Deal Led to a Life-Changing Podcast** - A major media company backed out of a deal on the day of signing, but that "no" cleared the path for a podcast that changed everything.
- 5 (24:01) **Listener Comeback #1: Jackie Wong - Finding a Career After 8 Years** - A listener shares how he felt stuck in accounting for years before discovering his passion in NetSuite ERP.
- 6 (25:26) **Listener Comeback #2: Jessica Yost - Hip Reconstruction to Marathon Finisher** - After a 17-year dance career, a hip reconstruction forced Jessica to relearn how to walk, but she went on to run a marathon.
- 7 (26:25) **Listener Comeback #3: Adriana Alvare - Laid Off to Multi-Million Dollar Brand** - Adriana was laid off from Coca-Cola in 2020 and invested her severance into her side hustle, which became a multi-million dollar brand.
+ Full timestamped outline available in the app
Show Notes
Nick & Jack share the best comebacks yet. In business, from us personally, and from you. Because TBOY hotline is where you’re in the CEO seat, so we’ve got the operator ready, with some fantastic voicemails to share.
- When Nick got cut from the lacrosse team and when Jack split up with his girlfriend he’d moved in with.
- When a big media biz backed out of a deal with us on the day we were supposed to sign.
- Your comebacks: You got fired, you got sick, you got injured, and your comebacks are inspirational
Thanks to @liquidiv for sponsoring the show! LiquidIV.com Use code 2026TBOY to get 20% off (first time purchasers only) LiquidIV.com
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