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.

fifthandcherry.com
bartaco.com

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