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.

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