Episode
How to build a company you’ll run forever | Zack Kanter (Founder and CEO of Stedi)
- Podcast
- In Depth
- Published
- Nov 6, 2025
- Duration seconds
- 5049
- Processing state
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- https://traffic.megaphone.fm/FRCH1542789833.mp3
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Summary
Zack Kanter is the founder and CEO of Stedi, an API-first healthcare clearinghouse. After bootstrapping a wildly profitable auto-parts business, he sold it to tackle "the most complicated problem" he'd ever encountered: business-to-business transaction exchange. He spent years building EDI infrastructure, threw away the entire codebase eight times, and found extraordinary traction in healthcare. Stedi recently raised a $70M Series B co-led by Stripe and Addition. In this conversation, Brett and Zack discuss why venture capital means "going pro," why execution is never actually a moat, and how "eating glass" became Stedi's competitive advantage. In today’s episode, we discuss: How 16-year-old Zack turned $2,500 into a wholesale empire Why bootstrapping means being "constrained by capital" and how VC removes that ceiling Why Zack rebuilt their EDI product eight times before launch The snake swallowing a deer: what extreme product-market fit really looks like What software companies can learn from discount retail and Toyota Why Stedi’s new hires are told "everything’s your fault now" And much more Where to find Zack: LinkedIn: https://www.linkedin.com/in/zkanter Twitter/X: https://x.com/zackkanter Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: Aetna: https://www.aetna.com/ Amazon: https://www.amazon.com/ AWS: https://aws.amazon.com/ Blue Cross Blue Shield: https://www.bcbs.com/ Change Healthcare: https://www…