How Jack Oujo Built an $800M Business by Planning for Failure | E5 artwork

How Jack Oujo Built an $800M Business by Planning for Failure | E5

Business MVP

July 28, 2026

One call ended Jack Oujo's dream of reaching the major leagues. After spending eight years as a professional baseball umpire, he was released just short of the top level.
Speakers: Jack Oujo, Sammy Peterson
**Jack Oujo** (0:00)
When you're in the minor leagues, it's like being on the television show Survivor. At the end of the season, they vote off half the umpires, and I stayed on the show for eight years before they got rid of me.

**Sammy Peterson** (0:10)
Too smart to be an umpire, after eight years of grinding through professional baseball. He was released from baseball by mail.

**Jack Oujo** (0:17)
I umpired 1,500 games in eight years in professional baseball. That's twice as many as Bill Belichick coaching the NFL.

**Sammy Peterson** (0:24)
That's insane. Today, Jack Oujo is the founder of Oujo Wealth Strategies, one of the nation's largest tax-focused wealth management firms, managing over 800 million in assets.

**Jack Oujo** (0:33)
I've never had a client go broke under my watch. After the 2008 financial crisis took place, my business went up by 400%.

**Sammy Peterson** (0:41)
Wow. Eight years calling balls and strikes under pressure, making split-second decisions. What did that experience build in you that you use in business every single day?

**Jack Oujo** (0:48)
Any successful athlete will always come back to having a process that works. When I went into business, I created processes.

**Sammy Peterson** (1:00)
He's been the number one financial advisor in the nation at his firm for most of the past decade and he wrote the book on turning rejection into reinvention. It's called Too Smart to Be an Umpire. Jack Oujo, welcome to Business MVP.

**Jack Oujo** (1:12)
Thanks for having me on Sammy. I'm excited to talk to you today.

**Sammy Peterson** (1:15)
Jack, you spent eight years grinding through professional baseball as an umpire, won the Joe Ryan Award as the top umpiring prospect in the country, and then baseball said no. Take me back to that moment.

**Jack Oujo** (1:26)
Well, it was pretty devastating. When you're going through the minor leagues, you realize that there's always that possibility. Until you're in the major leagues and you get that full-time contract, you know you need to have a plan B. So I had that formulated in my mind. I remember when the release came, I stared up at the ceiling. I was thinking I could feel sorry for myself for the rest of my life, or I could try to kick some butt and try to have a second career.
And my wife and I sat down, and we literally made a long-term plan that involved a lot of education. And what I did was I pounded the pavement looking for a job in accounting, and I was hired by Ernst & Young, EY.
I don't know how many 30-year-old accountants they hire with eight years in the minor leagues, but they hired me. And then because of the pain, I was self-aware of the pain I was going through with the release, and I decided to engross myself in education at night and on weekends. And within a four-year period, I passed all four parts of the CPA exam in one sitting, the CFP exam, the securities, I got my securities license, insurance license, and I got a master's degree in taxation, all within four years by not watching any baseball game. So I didn't even know what wealth management was. I didn't even know it was a job, but I just decided I'm going to focus on education, education, education, and just see where it takes me. So that's what the process was that I started.

**Sammy Peterson** (2:53)
That's impressive. So that's what that rejection did for you, right?

**Jack Oujo** (2:55)
It focused you on that.

**Sammy Peterson** (2:58)
That's pretty wild.
So eight years calling balls and strikes under pressure, making split second decisions with incomplete information, while everyone in the stadium thinks they know better, right? So what did that experience build in you that you use in business every single day?

**Jack Oujo** (3:13)
It built so many things. Learning how to handle pressure, dealing with worst-case scenarios, which was your release, being part of a team because when you're umpiring, all the movements when the ball is hit is an orchestrated event. Handling pressure, dealing with people on their absolute worst behavior, and doing the right thing in the face of adversity. These commercials on TV for financial advisors being fiduciary, I think are the dumbest things I've ever seen in my life. I mean, could you imagine an umpire going, I'm honest, hire me because I'm honest.
And when I see that, I just I can't believe that's the standard that people are running multimillion dollar commercials with. But there are some of the things that come to mind, Sammy.

**Sammy Peterson** (3:56)
Yeah. No, that's great. So what was your biggest failure as an umpire?

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