125: Seth Levine on Rebuilding Your Company for the AI Era From Scratch

What if the biggest mistake CEOs are making with AI is trying to improve the company they already have? Seth Levine believes leaders need to ask a more radical question: If you were building your company from scratch today, how would you design it? Seth is a founder, investor, author, and co-founder of Foundry, the venture capital firm he built alongside Brad Feld and their partners. After decades of working with founders, boards, and leadership teams, he has seen what separates businesses that adapt from those that remain anchored to the way things have always been done. In this episode of From Start-Up to Grown-Up, executive coach and bestselling author Alisa Cohn sits down with Seth to explore how CEOs should approach AI transformation, why incremental efficiency is not enough, and what it takes to rethink an organization from the ground up. Seth also shares the rarely told story behind Foundry’s creation, including the fifth founding partner who ultimately left the firm, the difficult conversation that ended a close friendship, and the months of rejection Seth and his partners endured while attempting to raise their first fund. At one point, Seth believed he had lost his family’s entire life savings. One pivotal yes changed everything, helping Foundry close a $225 million fund. This is a candid conversation about building boldly, leading intentionally, and creating enough space to breathe along the way. You’ll learn: The most important AI question every CEO and board should be asking Why using AI to improve productivity is not the same as becoming AI-native How legacy workflows prevent established companies from transforming Why CEOs need firsthand experience with emerging AI tools How Foundry used coaching to build a healthier partnership from the beginning How to prepare for a difficult leadership conversation Why Foundry’s first fund nearly failed before closing at $225 million How one significant yes can change the momentum of a fundraising process The three qualities Seth sees in the most successful founders How intentionality helps leaders remain bold without burning themselves out We talk about: 00:00 Meet Foundry co-founder Seth Levine 01:25 The 25-year relationship between Seth Levine and Brad Feld 02:06 How boards should evaluate the opportunities and threats created by AI 04:19 Why most companies are still only dabbling with AI 08:50 The difference between improving a company and rebuilding it for the AI era 13:08 How CEOs can redesign their organizational structure from scratch 14:05 Why leaders need to experiment with AI tools themselves 18:00 How organizational coaching shaped Foundry from the beginning 21:44 Seth’s productivity system and morning planning routine 26:38 The untold story of Foundry’s original fifth partner 31:11 The words Seth used to begin a difficult leadership conversation 37:39 The pivotal yes that helped Foundry raise its first $225 million fund 41:32 How writing helped Seth build his reputation and personal brand 55:00 The difference between expressing company values and entering politics 57:21 The qualities Seth looks for in successful founders 59:19 What Seth wishes he had understood earlier in his career 01:03:48 Seth’s advice for founders growing into leaders Follow Seth on LinkedIn: https://www.linkedin.com/in/sethjlevine/  Books: https://sethlevine.com/books/  Website: https://sethlevine.com/  Foundry: https://foundry.vc/  Connect with Alisa! Follow Alisa Cohn on  Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better)  Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon