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My Worst Investment Ever December 2025

Ep815: Jon Ostenson – I Built a Million-Dollar Business That Never Made a Profit

BIO: Jon is the Founder and CEO of FranBridge Consulting, a 2-time Inc. 5000 company, and he is a top 1% franchise consultant.

STORY: Jon co-founded a marketing and call-center business that appeared successful on the surface, growing to millions in revenue and dozens of employees. However, excessive customization and an inability to charge prices that matched rising costs meant the business never became sustainably profitable.

LEARNING: Profitability is oxygen. Knowing when to admit you’re wrong matters just as much as knowing how to start.

Access the episode’s show notes and resources

Ep814: Edwin Endlich – Early Doesn’t Always Mean Right

BIO: Edwin Endlich is the Chief Marketing Officer of Wysh and President of the National Alliance for Financial Literacy and Inclusion.

STORY: Edwin’s worst investment was buying Tilray stock at $143 during the early hype of legal cannabis investing. Swept up in the excitement of a “new frontier,” he held on as the price crashed—eventually selling at around 30 cents and losing over 99% of his investment.

LEARNING: The fundamentals always apply, even in new or exciting industries. Don’t let hype replace due diligence.

Access the episode’s show notes and resources


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DISCLAIMER: This content is for information purposes only. It is not intended to be investment advice. Readers should not consider statements made by the author(s) as formal recommendations and should consult their financial advisor before making any investment decisions. While the information provided is believed to be accurate, it may include errors or inaccuracies. The author(s) cannot be held liable for any actions taken as a result of reading this article.