My Worst Investment Ever Podcast · 2026-01-19 · 41 min
BIO: Jon is the Founder and CEO of FranBridge Consulting, a 2-time Inc. 5000 company, and a leading franchise consultant. STORY: Jon believes franchising remains one of the most effective ways to build durable income, especially when investors focus on operational discipline and unit economics. He shares his top franchise categories for 2026. LEARNING: Look for businesses with repeat customers, operational discipline, proven unit economics, and leadership teams that have already made their mistakes. Guest profile Jon Ostenson is the Founder and CEO of FranBridge Consulting , a 2-time Inc. 5000 company, and he is a top 1% franchise consultant. Jon is also the author of the bestselling book, Non-Food Franchising . Jon draws on his experience as a former Inc. 500 Franchise President and Multi-Brand Franchisee in helping his clients select their franchise investments. For many aspiring business owners, the biggest financial losses don't come from bad intentions. They come from underestimating complexity, overestimating scalability, or betting everything on an unproven idea. Jon Ostenson knows this lesson intimately.
Laurie Barkman - Don't Wait Until You're Exiting to Plan Your Exit77 / 100Ep820: Tony Martignetti - A Flattering Binder and $13,500 Down the DrainDavid Siegel - The Agentic Economy: Why AI Agents Will Redefine Work and WealthAthena Brownson - What Happens When Trust Replaces Due DiligenceDavid Siegel - A Smart Idea Nobody Wanted