About this episode

Jack Oujo shares his journey from a shattered career as a baseball umpire to founding a successful wealth management firm.

Starting over at age 30 with a pregnant wife, no money, and a shattered career dream could have broken Jack Oujo . Instead, it became the unlikely foundation for building one of America's largest tax-focused wealth management firms. Jack, founder of Oujo Wealth Strategies , relied on discipline, preparation, and relentless self-education to reinvent himself. Successful leaders, as he learned from personal experience, need a "Plan B" for when things don't go as planned. He also explains why consistent processes often matter more than lofty goals — and why trust and customer service became the cornerstone of his business philosophy. Before entering wealth management, Jack spent eight years as a professional baseball umpire. As he notes, however, unlike ballplayers, most people don't get three strikes when it comes to managing their finances. [Be sure to pick up a copy of Jack's book, Too Smart to be an Umpire , here .] Monday Morning Radio is hosted by the father-son duo of Dean and Maxwell Rotbart . Photo: Jack Oujo, Oujo Wealth Strategies Posted: May 4, 2026 Monday Morning Run Time: 46:56 Episode: 14.44 Now Available , The Much-Anticipated Sequel to All You Can Eat Business…

People in this episode

Hosts: Dean Rotbart, Maxwell Rotbart

Guest: Jack Oujo

Topics covered

• wealth management
• entrepreneurship
• self-education
• customer service
• financial planning

Keywords

• wealth management
• Jack Oujo
• entrepreneurship
• financial planning
• self-education

Mentioned in this episode

Organizations: Oujo Wealth Strategies

Books & works: Too Smart to be an Umpire

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