Episode

Jesse Lipson on Bootstrap Success and the SaaSpocalypse

Podcast: Software Spotlight
Published: Apr 11, 2026
Duration seconds: 3968
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Summary

In this episode of Software Spotlight, Michael Bernzweig sits down with Jesse Lipson, founder of Levitate and former CEO of ShareFile. Jesse shares his journey from philosophy major to tech entrepreneur, highlighting the challenges and triumphs along the way. He offers an in-depth look at the SaaSpocalypse affecting the software industry and how AI is reshaping the landscape. Tune in to hear Jesse's unique insights on bootstrapping success and navigating today's tech world.