#72 - Rachel Sklar (TheLi.st)
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#72 - Rachel Sklar (TheLi.st)
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About this listen
Rachel Sklar built the most powerful women-in-tech network before “women’s communities” were trendy. In this episode of The Exit Whisperer, Carrie Kerpen sits down with Rachel, founder of The Li.st, to unpack the kind of exit founders never brag about — because it’s not a flashy SaaS story.
They get into the messy parts people skip: charging for community (hello, “pay to be her friend” headlines), why “perfect-fit” acquisitions die when you wait too long, what happens when the buyer’s lawyer kills the vibe, and why sometimes the smartest deal is the one that lets you sleep at night — even if it’s not the biggest number.
02:25 Meet Rachel Sklar: The Original Community Builder
03:05 Building The Li.st Before “Women’s Networks” Were Cool
06:09 Protecting Trust While Scaling
09:34 The Controversy
23:10 The Lessons Nobody Tells You
32:23 The “Perfect CEO” Idea (And The Plot Twist)
32:41 Startup Institute33:01 What The Li.st Could’ve Become
35:12 Pregnancy Changes The Timeline
36:30 COVID-19 Proves The Li.st’s Real Value
37:46 Handing Over The House You Built
52:30 Rachel’s Next Chapter After The Exit
58:54 What She’d Do Differently Now