Personal Bets

Send us Fan Mail We pull a thread through three standout stories and lay out the hidden work that happens before a big risk pays off. We argue that smart bets come from pre-framing reality, auditing your own fear, and validating with real-world tests instead of vibes.   • shifting the show format and introducing “the bet before the bet”   • Justin Maxwell’s COVID SPY decision and why it was a fram...

Send us Fan Mail We sit down at Lakeridge Winery over a bold Napa Valley Cabernet and trace how a backyard vineyard experiment turns into one of Florida’s biggest wine operations. We talk candidly about leadership pressure, long-tenured teams, and the hard problem of keeping wine consistent while customers keep changing. • the family history from Tallahassee to Clermont and the launch of San Sebas...

Send us Fan Mail We talk about why “fewer better deals” beats chasing every opportunity, especially as AI makes it easier to move fast without real alignment. We trace Brody's path from early entrepreneurship at home through a startup exit and into micro private equity, with practical lessons on buying businesses, building trust, and planning for the day after the wire hits.   • Building a pe...

Send us Fan Mail Today we talk with a new friend, Bobby Davidowitz. Who started his career as a Publix Bag Boy, but pivoted to Real Estate in the early 2000's. Navigated the great financial crisis and is currently building the first of its kind, Culture Center. We talk through how a real estate brokerage wins on culture, not control, and why influence is the only thing you truly own as a lead...

Send us Fan Mail We sit down with Justin to trace the long road from sweaty manual labor to building a life where he does not depend on anyone else to sign his paycheck. Along the way we talk about big bets, bad bets, and the mindset shifts that turn money into time, options, and freedom.  • cutting grass and digging ditches as early motivation to level up  • hitting the Calculus Two brick wall an...

Send us Fan Mail One medical test can erase a “sure thing” career plan. Jorge thought he was on track for federal law enforcement until a color vision deficiency ended the process overnight, forcing a hard reset and a new question: now what? Jorge walks us through the pivot from criminal justice to the LSAT, law school, and early work that blended immigration law with the real mechanics of busines...

Send us Fan Mail Today we talk to a mentor of mine, amazing business broker, and Shackleton enthusiast, Shaun Thornton - Business Broker with FitzGibbon Alexander Inc. Shackleton’s ship gets crushed by Antarctic ice, his crew ends up stranded, and the only path to survival is a tiny boat crossing through some of the worst water on earth. That sounds like pure history, but we keep circling back to...

Send us Fan Mail A lot of people think therapy is just great conversations in a calm room.  The truth is, being a counselor is also running a business, carrying other people’s pain with care, and then walking back into family life like you didn’t just spend all day inside trauma stories. That’s why I wanted to sit down with Keenan Crowley, a Central Florida Registered Mental Health Counseling Inte...

Send us Fan Mail This week we sit down with John King, an EOS implementer and business coach, to unpack how he learned to spot misalignment early and help leadership teams get back in rhythm without blowing up the culture. His story moves from band leader to a venture-backed music tech startup, through a decade in ministry, and into building a coaching practice for second-stage companies that need...

Send us Fan Mail Jimmy Hartley's grandfather Len started H&H Products Company in 1964 with a $200 loan co-signed by his father, mixing syrup at home while his wife Betty Jean taught school during the day and bottled products at night. Sixty years later, H&H manufactures over 3 million gallons of beverages and syrups annually out of Orlando, FL, supplying theme parks, restaurant chains...