What happens when an ambitious startup faces the harsh reality of an insurmountable problem? In this episode, Joe Grover engages in a candid conversation with Jake Bengtzen, the founder of Zipper, as they explore the painful journey of his healthcare fintech startup. After 92 pitches, seven investors, and 18 months of relentless effort—during which Jake paid himself only three times—he ultimately hit rock bottom. After he launched Zipper Health with the goal of lowering healthcare costs for individuals and families, he faced challenges that proved overwhelming.
Jake shares the moment he realized that the multitrillion-dollar healthcare issue was too vast to tackle and that it was time to shut down Zipper. Reflecting on his experience, he states, “There are a lot of people who choose unhappiness over uncertainty,” emphasizing the importance of what one chooses to do after experiencing failure.
This episode dives deep into the emotional and psychological aspects of shutting down a dream. Jake discusses how failure shaped his perspective on entrepreneurship and resilience, offering insights into the difficult decision to pivot after such an investment of time and energy. Join them as they unpack the lessons learned from failure and what lies ahead for Jake as he contemplates his next steps in making a meaningful impact in the world.
Links:
Jake Bengtzen: LinkedIn (https://www.linkedin.com/in/jake-bengtzen-0a8ab365/)
Joe Grover: LinkedIn (https://www.linkedin.com/in/joelgrover/)
This episode is sponsored by Amplēo. Amplēo offers fractional executives in finance, marketing, and HR to companies of all sizes. Visit ampleo.com to learn more.
