On this week’s episode, Kent is joined by Gino Barbaro. Gino is an investor, author, coach, and co-founder of Jake & Gino, who has built a $400M multifamily portfolio and now teaches others how to do the same. In this conversation, Kent and Gino revisit Gino’s investing journey from restaurant owner to real estate mogul and dig into his “Jockey, Saddle, Horse” framework for evaluating passive investments. Gino shares lessons from his early mistakes—including losing $172K to “Maserati Mike”—and why understanding your relationship with money, your goals, and your alignment with sponsors is essential to long-term success.

Where to find Gino:
Website: https://barbaro360.com
Multifamily Education: https://jakeandgino.com
Podcast: Jake & Gino Show

Key Takeaways

• Gino’s early loss to a bad sponsor inspired his “Jockey, Saddle, Horse” framework—prioritizing the sponsor, alignment of interests, and then the deal itself.
• A good passive investor must understand the business well enough to read financials and ask smart questions.
• Alignment of goals is critical—cash flow, hold period, and risk tolerance should match between investor and sponsor.
• Don’t chase deals for the sake of activity—fall in love with the process, not the goal.
• Know your “why” and choose the right “race” to run—whether you want passive income, diversification, or a full-time transition.
• Persistence and accountability matter more than talent; success comes from disciplined follow-through.

Books mentioned

• Mindset: The New Psychology of Success by Carol Dweck — https://www.amazon.com/Mindset-Psychology-Carol-S-Dweck/dp/0345472322
• Atomic Habits by James Clear — https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299

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