From Bitcoin to Boat Storage: Joey Rosati on Diversifying Investments

I've gotten to know Joey Rosati (@rosaticorp) over the last 3 years working alonside hime in the VC trenches of Druid Ventures. Let me tell you, the VC world is a funny place and there are gems if you know where to find them. Joey is one of them. He knows that behind every successful business, it's all about people. In today's epic episode, Joey joins me to dive into the "silver tsunami," the massive shift as baby boomers retire, handing off old-school businesses to a younger generation. We talk about buying real-world companies like Dock Builder Supply and Boat Storage, the magic and messiness of mixing traditional business with new tech, and why true success often means blending hustle with humility.Joey shares his own wild entrepreneurial journey—from scratch-off lottery chaos in Guatemala to investing in MLS soccer, and why he now loves "ugly," cash-flowing businesses. We get real about stress, purpose, and why hard money lending might just be the smartest investment out there.We also talk about his role in preserving Tampa's adult entertainment legacy by taking over the world-famous 2001 Odyssey and Mons Venus strip clubs. We explore how he's balancing modernization with tradition, ensuring these establishments continue to thrive in a changing landscape.Buckle up as we cover:The real opportunities behind "boomer businesses."Why software can't replace specialized trades.Managing stress, staying sane, and finding purpose.When (and how) to walk away from a bad deal.Joey's top investment advice for 2025.Connect with Joey on X: @rosaticorp Thank you for listening to The Charlie Shrem Show. For more free content and access to over 400 episodes, visit www.CharlieShrem.com. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.