411. Jack Oujo. Too Smart to be an Umpire.
Jack Oujo
May 14, 2026
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In this episode, Jack Oujo, founder of Oujo Wealth Strategies and author of Too Smart to Be an Umpire, shares an inspirational story about chasing a dream, having it crushed, and building something greater from the wreckage.
Oujo spent eight years pursuing major league umpiring through low pay, cramped travel, and constant uncertainty. When he was finally released, a supervisor told him he was "too smart to be an umpire." The rejection devastated him. Thirty years later, he recognizes that getting fired from baseball was the best thing that ever happened.
The book examines pivot and reinvention through several frameworks:
Anger is performance, not personal. Umpiring taught Oujo that when people explode, they're often performing for an audience or expressing fear. Learning to let people exhaust themselves transforms conflict into conversation. This skill transferred directly to managing panicked clients during market downturns.
Process beats scoreboard watching. Oujo never set revenue targets. He designed client experiences and onboarding systems. Winners focus on perfecting repeatable flawless frameworks rather than obsessing over specific targets.
Parallel planning protects dreamers. While pursuing baseball, Oujo worked as an accountant during off-seasons. When his dream ended, he had marketable skills rather than starting from zero.
Rejection can fuel reinvention. The insult from that supervisor lit a fire. Oujo was determined to prove baseball wrong by building a spectacular career.
The conversation explores how skills from pursuing one dream can build another, why forced pivots create unexpected opportunities, and what it means to reconcile with a profession that rejected you. Click here to purchase the book
Jack Oujo CPA/PFS, CFP®, MS, is the founder of Oujo Wealth Strategies, one of the nation’s largest tax-focused wealth management firms. He has a bachelor’s degree in accounting from Seton Hall University and a master’s degree from Fairleigh Dickinson University. In addition to running a free youth umpire clinic every February, he has served as president of the NJ/NY Chapter of the College Baseball Umpires Association and as the freshman baseball coach at St. Rose High School in Belmar, New Jersey. Oujo divides his time between Fort Lauderdale, Florida and Sea Girt, New Jersey.
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