Most new companies fail, and the Dumb Money team is not immune to investments in failed startup companies. Today, they reminisce with the founder of one such company.

Episode 22 — Jordan, Chris, and Dave start their day meeting with a promising new startup seeking to bring fee reimbursement insurance to the billion-dollar club sports industry. Then, in route to lunch, Dave considers and dismisses opportunities sent to him by Chris to invest in a local premium cutting board company called Fifth and Cherry, as well as a vision-assist eyeglasses product launched by University of Dallas students.

Over lunch at Bar Taco, the Dumb Money team meets with James Bohan-Pitt, CEO of failed real estate tech start-up HipPocket. An honest conversation ensues where they break down why the investment didn’t go as expected. Their meeting proves fruitful in providing learnings that can be applied when assessing future opportunities.

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Chris Camillo:
Dave Hanson:

Note: Our videos contain personal opinions and are for informational and entertainment purposes only. They are not intended as investment advice or to provide investment strategy.

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