CapLander

Feel the Fear & Do It Anyway - Kaylin Roche on theSkimm, JIGGY Puzzles, Shark Tank and Building a Life Worth Investing In

48 min · 21. apr. 2026
episode Feel the Fear & Do It Anyway - Kaylin Roche on theSkimm, JIGGY Puzzles, Shark Tank and Building a Life Worth Investing In cover

Beskrivelse

What does it take to go from first employee at a hyper-growth media startup to founding a consumer brand, landing a deal on Shark Tank with Mark Cuban, and pivoting into angel investing and real estate development — all while raising two kids under two? Kaylin Roche has done exactly that, with intention every step of the way. Jody and Morgan sit down with Kaylin to trace the through-line of a career built on timing, brand instinct, and a willingness to walk through the door even when you're scared. From scaling theSkimm from 100,000 to 8 million subscribers, to launching JIGGY Puzzles four months before COVID accidentally made it a cultural moment, to revitalizing Buffalo's historic Allentown neighborhood — Kaylin brings the kind of founder clarity that only comes from having actually done it. The conversation gets real on bootstrapping vs. raising capital, knowing when to sell, why brand identity isn't something you can fully outsource, and the "founder mom pilot era." If luck is just what happens when experience meets opportunity, Kaylin has put herself in position for a lot of it.

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