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? 💡
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.
🎙️ The Necessary Entrepreneur, hosted by Mark Perkins, features authentic conversations with founders and leaders who've built businesses worth studying.
📌 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 📌 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/