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

Business MVP

Jack Ojo, former professional baseball umpire who called 1,500 games over eight years, transformed his career after being released by mail. He leveraged his experience under pressure, built a written financial plan, earn

Key takeaways

• Jack Ojo umpired 1,500 games over eight years—twice as many as Bill Belichick has coached in the NFL.

Transcript preview

Speaker 1: Speaker 1 (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. Too smart to be an umpire. After eight years of grinding through professional baseball, he was released from baseball by mail. I umpired 1,500 games in eight years in professional baseball. That's twice as many as Bill Belichick has coached in the NFL. That's insane. Today, Jack Ojo is the founder of Ojo wealth strategies, one of the nation's largest tax-focused wealth management firms, managing over 800 million in assets. I've never had a client go broke under my watch. After the 2008 financial crisis took place, my business went up by 400%. 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? Any successful athlete will always come back to having a process that works. When I went into business, I created processes. 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 Ojo, welcome to business MVP. Thanks for having me on, Sammy. I'm excited to talk to you today. So, 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. Well, it was pretty devastating. When you're going through the minor leagues, you realize that there's always that possibility until you're into 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, E.Y. 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 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. That's impressive. So that's what that rejection did for you, right? Does it focus you on that? 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? 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. Yeah. And when I see that, I can't believe that's the standard that people are running multi-million-dollar commercials with. But there are some of the things that come to mind, Sammy. Yeah, no, that's great. So what was your biggest failure as an umpire? I mean, other than maybe the release. And how did that shape how you handle failure in business? I think my failure as an umpire, when I look back on it, there really are not too many things I regret taking place on a baseball field. I regret some political mistakes that I believe I made, um, not adjusting to, um, a particular supervisor's style that they want it, perhaps not teaching at umpiring school. I learned that political mistakes can be career mistakes. Yes, unfortunately. And I was very aware of how politics would affect my career after baseball. And I'm very aware of those situations. And I think that's probably the biggest mistake. As a young umpire, younger umpires can be more aggressive. and I probably could have used better human relations skills, especially the early part of my time in the minor leagues. How did you stay sharp and focused during a baseball game? Like you can't miss a second, right? Like literally you can't miss anything. How did you do that? Was that like endurance training basically? Like you got used to it. Like how did you do that? So how do you, and how do you stay sharp now? When you're a home plate umpire, the level, and again, I'm, I'm a person. I played baseball. I played on a state championship team. Post baseball. I played an adult baseball and coached a state championship team post baseball. So the focus that the home plate umpire has is about the same as a batter in a baseball game, I would say, or a pitcher, all right? It's that level of focus because your standard is perfection. You cannot miss a pitch, okay? So you're trying to get every pitch right. And you got to remember the ball's coming in at 95 miles an hour. There's a safety issue involved. But if you're not paying attention, you can get. physically injured. It's kind of like driving a car when it's a driving rain, if you will, that you must concentrate or I'm going to die here. So that's the level of focus. And I go back to process. If you're dealing with athletes on this podcast, any successful athlete or coach will always come back to having a process that works is what results in victories. And when I umpired, I had a process that worked. I peaked at the bottom of the zone as I was getting set early, eyes at the top of the zone. I could see the inside and outside corner. I locked in and I called pitches with slow timing. I mean, I haven't umpired a game in 15 years, but I remember the process like it was yesterday. And when I went into business, I created processes that worked and that was critical. Yeah, no, that makes total sense. I love that. So while you were umpiring and you've touched on this little bit already, you were also working as an accountant in New York every off season. You were building your plan B while, you know, still in plan A. And so how intentional was that? And what made you think that way when most people just focus on a dream in front of them? Was it because you were always kind of fearing that it may not work out or, you know, what drove you to do that? Because a lot of people, they can't, you know, they don't make the time to do something like that when they're focused on the dream. I think everything, especially if you're a baseball fan, everything is risk reward in business. everything is risk rewards. So here I am, I'm realizing I'm taking this huge risk at the age of 22, giving up my accounting degree to try and go into baseball. And even though I had limited time in the off seasons, you have to remember, I had, I was in baseball eight seasons, so I had seven off seasons. Six of those off seasons, I was assigned to winter ball. So I umpard 1,500 games in eight years in professional baseball. That's close as many as Bill Belichick has coached in the NFL. That's insane. During that time, I did not allow myself to go on vacation like other people did. I got a job in New York City working for a financial printer, Charles P. Young Company, which is now morphed into R.R. Donnelly. And they hired me every offseason. They let me come and go as I please. And I picked a very valuable experience in it. And I think it benefited me greatly. Had I made it in baseball, our plan was my wife who was working for the Attorney General in New Jersey, wanted to go to law. school. And if I was successful in baseball, my wife, Eileen, probably would have went to law school. But that didn't work out. That's so funny. I'm sure. I feel like maybe we've crossed paths. I used to work in banking in New York City, and I went to law school in New York City. So that's funny. Very cool. Very cool. Love that. Yeah. So for the entrepreneurs listening who are still in their day job and thinking about making that jump, what's your advice on