Personal Bets
Small and Medium Businesses are the backbone of America. I interview those that chose to bet on themselves, and America is better because of them.
Personal Bets
Latest Episodes
Christian Slupe: From The Ledgers To The Cellar, Lakeridge Winery
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 prob...
Brody Vinson: Business Is "My Pleasure," From Chick-fil-A To LOI's
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 privat...
Bobby Davidowitz: Building Wealth Beyond Money, From Bag Boy to CEO
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....
Justin Maxwell: From Ditches To Riches
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...
Jorge Sevilla: When The FBI Said No And The Bar Said Yes
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 ...