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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 and pivoting into a business degree
• first trades that hooked him and losses that taught humility
• buying Google early and thinking in decades not days
• getting burned by corporate America and learning you are a number
• the COVID SPY bet, drawdowns, and why he stopped looking
• risk tolerance, overleverage, and staying calm in a big Meta swing
• a bourbon investment that got blindsided by tariffs
• why money is not the goal and how to work backward from expenses
• investing in people, trust signals, and the one-lie rule
• selling Google shares to buy a cash lake house with zero regret
• book picks for investing psychology and mindset

Mr.Moneymaxwell.com

ABOUT PERSONAL BETS

Person Bets is a podcast for the people actually running the business, not the investors, not the board, not the consultants on the sideline. Hosted by Chance Sweat, business broker at FitzGibbon Alexander, Inc. and founder of Foundry Leadership.

🔗 Personal Site: chancesweat.com
🔗 Brokerage Site: fitzgibbonalexander.com
🔗 Follow Chance: @thechancesweat