In this episode of Outsider Inc., host Ian Hathaway speaks with Jon Lensing, co-founder and CEO of OpenLoop, a telehealth infrastructure platform headquartered in Des Moines, Iowa. From growing up in rural Iowa to training as a surgeon, Jon’s path took an unconventional turn when he left medicine to build a company addressing healthcare access. Since its founding in 2020, OpenLoop has scaled to more than 2 million patients annually, raised over $120 million, and reached unicorn status while staying rooted in Iowa. Jon shares how constraint breeds creativity, the scrappy early days writing letters to doctors in a grocery store café, and the near-collapse when a term sheet fell through the night before payroll. He also reflects on co-founder dynamics, the lessons of a major pandemic pivot, building a fire-eating culture, and why success stories in outsider places fuel the next generation of founders.
Show Notes:
(07:42) Medical school, entrepreneurial sparks, and building side businesses
(12:06) The decision to forgo residency and launch OpenLoop
(14:03) Scrappy early days: handwritten letters, Hy-Vee café, and Techstars Iowa
(18:00) Capital constraints, rejections, and why scarcity fueled efficiency
(20:01) Meeting co-founder Christian Williams and complementary dynamics
(22:16) Making a high-stakes pandemic pivot into telehealth infrastructure
(28:14) A pulled term sheet, payroll crisis, and lessons on choosing investors
(33:02) Building a “fire-eating” culture and hiring for high-output operators
(38:12) Why Jon chose to build in Iowa and the advantages of staying close to customers
(45:55) Beyond the Bio with Jon Lensing
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guest: Jon Lensing, Co-Founder & CEO, OpenLoop
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
