About this episode
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.changehealthcare.com/
Cigna: https://www.cigna.com/
Clay: https://www.clay.com/
Costco: https://www.costco.com/
Ford Motor Company: https://www.ford.com/
GM: https://www.gm.com/
HIPAA overview (HHS): https://www.hhs.gov/hipaa/index.html
Jeff Bezos: https://x.com/JeffBezos
Kanban / TPS (Toyota): https://global.toyota/en/company/vision-and-philosophy/production-system
Microsoft Teams: https://www.microsoft.com/microsoft-teams
NetSuite: https://www.netsuite.com/
O’Reilly Auto Parts: https://www.oreillyauto.com/
Peter Thiel: https://x.com/peterthiel
Porter’s five forces: https://www.isc.hbs.e
