The Necessary Entrepreneur #154 - Building Twice: Jesse Lipson on Scaling ShareFile, Selling for $93M, and Starting Levitate
What makes a successful founder dive back in after a major exit? π‘
In this episode of The Necessary Entrepreneur, host Mark Perkins sits down with Jesse Lipson, founder and CEO of Levitate, a fast-growing SaaS platform helping service businesses build authentic client relationships at scale. Before Levitate, Jesse founded and sold ShareFile to Citrix, where he later served as a public-company executive before leaving to start all over again.
Mark and Jesse dive deep into the psychology of entrepreneurship, the pressure of building a second company after a big win, and how to keep relationships real in a digital world. Jesse shares powerful lessons on:
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Scaling relationship-based businesses with software
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Finding product-market fit and applying first-principles thinking
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Why entrepreneurship never gets easier, no matter how many times you do it
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The rise of AI tools and what it means for small-business growth
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Building and leading teams through constant change
Whether you're a first-time founder or a seasoned entrepreneur exploring your next move, this episode will inspire you to rethink creativity, risk, and leadership.
ποΈ The Necessary Entrepreneur, hosted by Mark Perkins, features authentic conversations with founders and leaders who've built businesses worth studying.
π Connect With Us:Website: https://www.thenecessaryentrepreneur.com/ YouTube: https://www.youtube.com/@thenecessaryentrepreneur Instagram: https://www.instagram.com/thenecessaryentrepreneur/ Facebook: https://www.facebook.com/TheNecessaryEntrepreneurPod X (Formerly Twitter): https://twitter.com/MPerkinsTNE LinkedIn: https://www.linkedin.com/company/tnepod/ TikTok: https://www.tiktok.com/@tneclips Spotify: https://open.spotify.com/show/6xhGUE1yzy2N0AemUOlJPx?si=d1c5c316af404f15 Apple Podcasts: https://podcasts.apple.com/no/podcast/the-necessary-entrepreneur/id1547181167 π Find Out More About Jesse Lipson & Levitate:https://www.linkedin.com/in/jesse-lipson-625195/ https://x.com/jesselipson https://www.levitate.ai https://www.linkedin.com/company/real-magic/