Capital-Constrained & Mission-Obsessed: How Pressure Forged a Healthcare Unicorn in Iowa w/ Jon Lensing, Co-Founder & CEO, OpenLoop

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Sep 17, 2025

Jon Lensing, co-founder and CEO of OpenLoop, talks about transforming healthcare access through telehealth from Iowa. He shares his unconventional journey from aspiring surgeon to startup founder, highlighting the scrappy beginnings of OpenLoop in a grocery café. The discussion dives into how capital constraints fostered creativity and efficiency, the challenges of a late-term sheet reversal, and lessons learned about investor alignment. Jon emphasizes the importance of mentorship in building local ecosystems and encourages aspiring founders to take action on their ideas.

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ANECDOTE

Handwritten Letters And A 10x10 Office

Jon and Christian handwrote 300 letters and bought stamps to recruit physicians when they started.
Their first office was a 10x10 sublet with a mini fridge and an old coffee pot.

INSIGHT

Constraints Breed Durable Efficiency

Capital constraints forced OpenLoop to optimize and become ruthlessly efficient.
Jon Lensing credits scarcity for building a durable, revenue-focused company DNA.

INSIGHT

Complementary Founder Roles Win

Complementary founder roles beat carbon-copy cofounders for operational effectiveness.
Jon handled external-facing duties while Christian owned internal ops and detail work.

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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

Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.