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

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00:00:00

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 8 years before they got rid of me.

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Too smart to be an umpire. After 8 years of grinding through professional baseball, he was released from baseball by mail.

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I umpired 1,500 games in 8 years in professional baseball. That's twice as many as Bill Belichick coached in the NFL.

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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 $100 million in assets.

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I've never had a client go broke under my watch. After the 2008 financial crisis took place, my business went up by 400%.

00:00:41

Wow. 8 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?

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Any successful athlete will always come back to having a process that works.

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When I went into business, I created processes that 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 O'Joey, welcome to Business MVP.

00:01:12

Thanks for having me on, Sammy. I'm excited to talk to you today.

00:01:15

So Jack, you spent 8 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.

00:01:26

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're— 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, uh, 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 8 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 4-year period, I passed all 4 parts of the CPA exam in one sitting.

00:02:30

Nice. The CFP exam, the securities— I got my securities license, insurance license, and I got a master's degree in taxation all within 4 years by not watching any baseball games. 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 gonna focus on education, education, education, and just see where it takes me. So that's, that's what the process was that, that I started.

00:02:53

That's impressive. So that's what that rejection did for you, right? Is it focused you? Yes. On that. That's, that's pretty wild. So 8 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?

00:03:13

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, 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 'cause I'm honest.

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Yeah.

00:03:46

And when I see that, I, it just, I can't believe that's the standard that people are running multimillion dollar commercials with. But there's some of the things that come to mind, Sammy.

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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?

00:04:05

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. Not adjusting to a particular supervisor's style that they wanted, perhaps not teaching at umpiring school. I learned that political mistakes can be career mistakes.

00:04:29

Yes, unfortunately.

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And I was very aware of how politics would affect my book post-baseball life. And I'm very aware of those situations now. 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.

00:04:55

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?

00:05:08

When you're a home plate umpire, the level of, and again, I'm, I'm a person, I played baseball, I played on a state championship team post-baseball. I played adult baseball and coached a state championship team post-baseball. So the focus that the home plate umpire has is, 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, there's a safety issue involved. Right. If you're not paying attention, you can get physically injured. It's kind of like driving a car when it's driving rain, if you will, that you must concentrate or I'm going to die here. So, so, 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 peeked at the bottom of the zone as I was getting set early, eyes at the top of the zone.

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I could see the inside and outside corner. I locked in and I called pitches with, with slow timing. I, 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.

00:06:38

Yeah, no, that makes total sense. I love that. So while you were umpiring, and you've touched on this a little bit already, you were also working as an accountant in New York every offseason. 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 the 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? Cuz 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.

00:07:06

I think everything, if, especially if you're a baseball fan, everything is risk reward. In business, everything is risk reward. So here, 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 8 seasons, so I had 7 off-seasons. 6 of those off-seasons, I was assigned to winter ball. So I umpired 1,500 games in 8 years in professional baseball. That's twice as many as Bill Belichick coached in the NFL.

00:07:41

That's insane.

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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 has now morphed into R.R. Donnelly. And they hired me every offseason. They let me come and go as I please. And I picked up very valuable experience. And 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, but that didn't work out.

00:08:20

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.

00:08:27

Oh, very cool. Very cool.

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Love that.

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Yeah.

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Yeah. So for the entrepreneurs listening who are still in their day job and thinking about making that jump, what's your advice on timing that transition?

00:08:37

What anybody needs to do, in my judgment, there's a couple of things. Number one is I think people need to make a plan a written plan, but the plan should be with math. Okay, so outline if you're going into business, what do you expect your revenues to be looking like in best case, ideal cases, worst case scenarios? Run some scenarios out with your expense and see what those numbers look like before you make any decisions. Maybe you'll look at it and go, well, that's, that's ridiculous. Or yeah, I can go for it. And I would also seek out people that have done something similar to what you— to, to what you want to do, like being on this pod— podcast, seeking out advice so that you can cut down on the mistakes that you're going to make.

00:09:23

100%.

00:09:24

When you, when you put this in writing, a lot of these decisions, in my opinion, Sammy, become self-evident.

00:09:30

Yeah, no, that's great advice. So when baseball ended, you already had a foundation, obviously. What mattered most in those early days of building something from scratch when you didn't really have inherited clients or institutional backing?

00:09:44

It was— I, I decided, uh, it's, it's the old line from, uh, Mike Shashevsky, um, Rick Bettino also: if, if, if you want to be successful, deserve success. When I went into wealth management, I, I was— I had an attitude that I was going to work harder than anybody else and smarter. And it started with my education, So I felt like I have all these freaking letters next to my name. I deserve it. And then two, because of the experience in baseball, you know, when you're in the minor leagues, it's like being on the television show Survivor. The end of the— at the end of the season, they vote off half the umpires. And I stayed on the show for 8 years before they got rid of me. But I had the attitude with clients, like I was fighting every client I got. I was fighting to keep them from the day I had them. And I created this overwhelming level of service whereby, unbeknownst to me at the time, now it's a strategy, but I created raving fans. And I consider myself, I am at heart a nerdy accountant, I guess. But I created raving fans for my business that brought me all the clients I needed.

00:10:55

In my business, as you previously mentioned, I was the number one advisor in my firm for over a decade using math. But it was because these clients were sending people to me. Okay. It wasn't because I had some BS clothing line or something like that. Yeah. It was because of the service model. Right, right, right. Exactly.

00:11:13

I love that. Yeah. So now you manage over $800 million in assets. So take me through the journey of actually scaling to that number. Like, were there inflection points where the business went from surviving to thriving? Tell us about that.

00:11:26

Again, using math in, in about 35 years of being in business, there were only 3 years where the numbers, uh, from a revenue from a revenue point of view, were lower than they were the year before. And they were during, uh, the 2000 to 2002 bear market and the 2008 financial crisis. And then there was some one other oddball year that took place. But in my business, what I didn't realize, which I was doing successfully, was that because of what happened to me in baseball, this getting released, and I vowed this was never gonna happen to me again. When I was a younger advisor, I appreciated a retiree coming to me with their whole life savings and realizing how precious that money was to those people. And so in my business, I, I, I did plans based on worst-case stock markets, not optimal stock, stock markets.

00:12:19

So a lower risk.

00:12:20

Yeah, right, right. And when these crises took place, even though my revenues temporarily went down, the business skyrocketed after that. If you're a financial advisor, money moves during down markets. Right now with the markets up, clients aren't moving their money. Everybody's happy. Look how much money I made in my 401. But when there's a 20% downturn, that's when money moves. And after the 2008 financial crisis took place, my business went up by 400%. I didn't lose one single client during that crisis. And so by— and again, to draw us— because this is kind of a sports show a little bit, Bobby Knight, the basketball coach, wrote a book called The Power of Negative Thinking, where he talked about worst-case— rather, baseball or basketball games are lost, not won. And in the finance business, I'm dealing with a lot of millionaires and I'm trying to convince them, you won the game. You know, we won. We don't have to win by 40 points. Let's, you know, take our ball, go home, have an exciting life and keep the money part, you know, moderately boring, you know, so That's kind of where the thinking was involved with that.

00:13:27

So, but as, you know, over a 35-year period, there are ebbs and flows. Anytime I got slow in my business, I went back to, I'm gonna get in front of clients, I'm gonna see them. I had a sign in my office that said, if I'm in front of, if I'm looking at a computer screen, I'm probably doing something wrong. And if I'm looking across at an eyeball, I'm probably doing something right.

00:13:50

So I love that.

00:13:50

I made, I made appointments, I got in front of people, I pounded the flesh, and then the business would, would grow again.

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Would follow. Got it. I love that. Yeah.

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Yeah.

00:14:00

So what are the biggest financial mistakes you see successful people making that are quietly costing them?

00:14:06

When people are successful, I think a lot of people were successful maybe in their jobs or in a business, and for some reason they put it at risk again, which I don't understand that, that The, the baseball player Curt Schilling, I think, lost his entire net worth in, in the first year out of baseball, which is ridiculous for somebody so, so smart. So not understanding risk and reward would be the big one. Start with that. And again, I go back to the math example. If, if people put their finances on a spreadsheet or a piece of paper and just line it out with these positive and negative scenarios, it will prevent them from making stupid decisions. It would also help them feel more comfortable, probably in the present situation that they have. I've done that with all my clients. I've never had a client go broke under my watch or run out of money on my watch. If I felt they were doing it, I fired— I ejected them like I would as an umpire, as a client, because I didn't want to see anybody go down on my watch. That's how seriously I took it.

00:15:08

So again, using an analytical approach, I think a lot of people make decisions You think about why are beer commercials with girls playing volleyball in bikinis? You're selling feelings, okay? And people make too many decisions on feelings when they should be more a little analytical in their approach, in my view.

00:15:26

There's lots of books about that, by the way.

00:15:29

Okay, exactly, exactly, exactly.

00:15:31

Leading with Emotion, Bad News, right? So. Right.

00:15:35

But I try to, with the analytics, combine that. I have the analytics with my clients, and then I try to, get in their face in a respectful way. Here's why this is a stupid way to go or a smart way to go or the ideal way to go. And I try to be an advisor like Dr. Phil, where I'll say to the client, I know the right answer. I want you to get to the right answer. And then I know we're on the same page here. That's, that's what you're trying to do.

00:16:00

So is that how— is that what you would say is how you establish credibility?

00:16:03

Well, by doing what I said I was going to do, underpromising and overdelivering. And then I think, again, for me, being very responsive was a big deal. We live in the world of Bernie Madoff. And to me, when a client emailed me on a Saturday morning, I was returning it on a Saturday morning, or a phone call. As long as there was mutual respect, people weren't getting out of line. If they got out of line, I knew how to handle it from my baseball days.

00:16:29

Wait, which is what?

00:16:30

Well, if you're an umpire, I mean, now there's analytics for umpiring. You know, you could tell somebody's safe or out with your phone. You know, I don't know how much of a human being is that. I don't need it anymore. But when I was an umpire, I was trying to get respect from players and managers, and I had to get 100 calls right to be able to get that respect. And I based my entire business on mutual respect between me and our client, or the people that work in our office and our client. Mutual respect. And we did several things to do that. For one thing, we did, when I met with clients for the first time, I would gather information, shut up and listen, deliver written full financial plans in writing without taking any money up front to see if the clients were comfortable with it, making myself vulnerable. So a lot of things I learned in baseball I applied to business, and mutual respect was probably at the top of the list.

00:17:27

Yeah, that's all great advice. So what's the hardest business decision you've had to make, and how did your background as an umpire shape how you handled it?

00:17:34

Great question. The biggest decision— the biggest decision I had to make was when to get out. Okay, is, is I'm 67 years of age right now. And when I was 57 years of age, I realized that I had a star-based system, Ojo Wealth Strategies. And, and so the question became, this business is pretty cool. We're making a lot of money. My kids don't have student loan debt. Everything's pretty great now. Now, how do we get out of this thing? And in a way that's, that's morally right. And what I did was I mentored people in my office. And I ended up selling the business effective January 1st, 2026 to two of our employees. And they now own the business and they're, they, they're paying me out over many years. So from a moral point of view, I learned in baseball in the minor leagues that people get treated like garbage unless you're in the major leagues, probably on your second contract. And I treated my employees right, including enable them to purchase the business from me. Okay. And, um, And they're doing great with it. All the clients have stayed. I worked hard on coaching them, mentoring them so that they would be in this position.

00:18:41

But knowing when to get out, I could have milked it for a few more years. I mean, I live in Florida most of the year. I could have played golf 4 times a week and just milk the business. But there became, there was a moral and fiduciary, in my opinion, obligation of when to get out so that the clients would be taken care of and our employees would be taken care of. And that, That comes again from being an umpire, doing the right thing.

00:19:06

I love that. That's pretty amazing. I don't think a lot of people could say that. So thank you for sharing that.

00:19:12

I always felt if you do the right thing over and over, and I'm a person of deep faith, I believe if you do the right thing over and over again, good things are gonna happen. You have to have a good sense of right and wrong, which, and when I saw things that were wrong, I would stand up and fight for it in a respectful way.

00:19:29

Um, so we've talked a lot about what you built, right? I wanna, and, and then how you think too, but I wanna shift a little more on to how you think based on some of these things. So as an umpire, you had to make the right call. We've talked about this in real time with thousands of people telling you you're wrong, right?

00:19:43

Sure.

00:19:44

So how has that shaped how you make decisions under pressure in business, especially when the stakes are someone's life savings, like you said, or their retirement?

00:19:52

I always found it after being in baseball, and again, you know, walking in the winning run with 30,000 people in the stands. And if I could just tell you a very quick story, I'll digress for a second. And I wrote a whole— my whole book, Too Smart to Be an Umpire, is loaded with stories like this. But I was in Greenville, South Carolina, in AA, and I had a play at the plate where I ejected. The third base coach came flying in to argue, argue the call, and I just ejected him for leaving his position. But later that night, My buddies and I went to the bar to have a drink and just hang out. And on TV, on the 11 o'clock news, was a replay of this play at the plate. And there's people at the bar arguing whether or not the guy was safe or out, not realizing that the umpire that made the call was having a beer with him at that very moment.

00:20:42

Okay?

00:20:42

And you realize that you just— an umpire is just trained to do the right thing. Even though fans think you have a bias, all an umpire really cares about, believe it or not, is getting the play right. Right. And that just became my mindset. So when negative events take place in the world, I could look people right in the eye and I go, this is the right thing we need to be doing here. It wasn't— I was never afraid of a client firing me for doing the right thing. If you want to fire me, go, go somewhere else. I, I've dined with Chef Boyardee or Kraft macaroni and cheese in my life when I was a poor umpire. So this, this wealth that we have in this business is hysterically funny to my wife and I, this fantasy existence we have now, because we were very poor for many years. I love this. So just do it. You just do the right thing, and whatever happens happens. That's how I raised my children. I have 3 children that are adults now. They're all doing great, and they were raised that way. Just do the right thing.

00:21:38

No, that makes sense. And then you just mentioned your books. I want to talk about that too. So the book's called Too Smart to Be an Umpire, which is what they told you. When, you know, shortly before your release, it sounds like. So, what's the main message of the book and for those who haven't read it yet, and who did you write it for?

00:21:56

The book has a lot of messages, and I'm glad you asked about it. It's for a baseball fan. They will see what going through the minor leagues is like from an umpire's perspective, just how hard it is, the promotions, the denials, what happens along the way, the 8-year investment that's made. I take you through the whole process. And then from the day you're released, the, uh, everybody likes a reinvention story. How do you, how do you, how do you reinvent yourself with a pregnant wife and no money and, and, and, and, um, bit more like a negative net worth? How do you start a business with nothing? How does that work? And how did you, how did you grow it to be, you know, it, it, in the business community, I have a lot of respect for what I've done, but they, they have no, most people have no idea about the baseball background. So, so what did you learn in baseball? How did you grow the business? How did you get out of the business? And how do you have fulfillment in family as well? So I connect the dots in a very easy read.

00:22:54

It's an Amazon top 10 bestseller now in its category, and I'm just thrilled with the feedback I've gotten. Yeah, I'm— I just did it. You know, I said these two guys were taking over the last year. I thought my clients would need me more and I was getting bored. And that's when I wrote the book. I'm like, I have Too much time on my hands.

00:23:12

You're hilarious.

00:23:14

I had no intention of writing a book. I'm like, I'm so freaking bored here. So it took me about 8 months to write it, and I'm very happy with how it turned out.

00:23:23

That's so awesome. Yeah. I've glanced at it, and it's amazing. I encourage everyone to grab a copy.

00:23:28

Thank you.

00:23:29

Thank you. So if you could go back and tell your younger self one thing about what success actually requires, what would that be?

00:23:36

Number one, with the great attitude, which I believe I did. I'd actually like to thank that younger version of myself for getting it. Getting to where we are right now. But, um, go, go for your goals and don't let anybody tell you no, okay? Because a lot of people, especially in this world we live in, there's so much— I didn't realize until the internet came available how angry people are with their lives. But, but yeah, you have to start with a great attitude. I think having a supportive spouse or partner is, is very, very important. And again, if you make this written plan, okay, it doesn't have to be fancy schmancy, a spreadsheet, whatever. Outline, you know, the best thing that can happen, the worst thing that can happen. For me, when I looked at the— what is the worst thing that can happen? I looked at it, my wife looked at it. That's not so bad. We could live in that. We've, we've had worse. Okay, so that then that would help you, um, make good decisions. And so the younger version of myself, I'm glad I did what I did. I'm 67. I have no, no regrets whatsoever.

00:24:36

None.

00:24:36

I love that. And then just to back up a little second on what you just said, but I think knowing what the worst case scenario is too, and being okay with that lets you proceed without fear. And that's really important 'cause people don't make good decisions when they're based in fear, right?

00:24:49

So, correct. Correct.

00:24:50

I love that. I didn't wanna let that go. Yes. 'Cause that was a good point that you made. And then further to that, you know what I mean? It could be that again, which is a good attitude, but I'm curious, you know, what habit or principle, and it can be good attitude again from your time as an umpire, do you think every entrepreneur, athlete or not, should adopt immediately?

00:25:05

I would think about, I would think about their client or customer experience. If you're going to be, if you're going to be in business, if you're going to be in business, what is your client or customer experience going to be like in terms of dealing with you? And I would go back to my clients or customers to find out what that experience is like. I would also go back, if you have employees, go back to your employees periodically to find out what is their feedback and what's happening. Because I was an umpire, I do have a thick skin. People— I felt comfortable taking criticism. A lot of people can't do that. They don't want to hear constructive criticism. So get feedback from a lot of people and don't be afraid to get beat up and make adjustments. Because if you're in business, you're going to have to make a lot of adjustments. You're going to make mistakes. They just can't be fatal. That's all.

00:25:55

Did you have a lot of mentors or people that gave you advice along the way, or was this just kind of stuff you learned along the way?

00:26:01

It's another great question. I sought them out. I sought them out. When I went into the wealth management business, I called our broker-dealer and I go, can you tell me who the best advisor is in the country? Doesn't have to be the top producer, but who's the best advisor? And they go, oh, you got to call this guy John Rudd in North Carolina. So I called him up and I asked if he could fly up to New Jersey. I paid for his ticket and I had him sit down with me. I had to make a client presentation. And I go, you just saved me about 5 years of stupid mistakes, sir. I really appreciate that. And to this day, John Rudd, who's who's now in his mid-80s, I believe, are very good friends because he mentored me. In baseball, the first time I umpired a baseball game, there was a guy who went to umpire school and he looked at me and he goes, Jack, you have no idea what the bleep you're doing out there, do you? And I go, no. And he goes, if you want, I'll mentor you and I will help you.

00:26:51

And he did. And I ended up getting into professional baseball. And I just am amazed at how many people, like, to this day, I probably get a phone call a month or a text from a college kid or somebody seeking advice. And they're smart to make that, that call. But a lot of people don't. I think people need to ask and find out. People are willing to give away information. They're willing to help you. Most people are very good, especially successful people. We all like to hear our own story, but, but people will help you if you ask. So I think it's a big deal and I think it's a big mistake not to have mentors. And again, with, with my children, again, very quickly, my, my daughter, I, begged her to get internships and seek out mentors. She now represents the United States of America as the Department of Energy's attaché in Beijing, China. My son wanted to be a pilot. We brought pilots into the house to give him career advice. He became a captain with Alaska Airlines at the age of 32. So it does work no matter what you're going into.

00:27:50

That does work.

00:27:52

Yeah. No, I think that's great advice because— and a lot of people have done it before you. And like you said, they've made the mistakes for you. Right. So, it's just silly to repeat the same things if you can avoid it, right? So, I think that's great advice. But also, just knowing what to expect in someone that's seen the other side is invaluable, right? The whole, like, what you actually have to do to get to that other side. So, that's great advice. Yeah. I read that every February for over 20 years, you've run a free youth umpire clinic. So, I love this, giving back to the game that cut you. So, and not with bitterness, right? But with generosity. No. So, where does that come from? And do you still do that?

00:28:29

I don't do that anymore because we live in Florida most of the year now. So when we went to Florida, I stopped doing it. It actually came from coaching at the Little League, and they were having problems with umpires and umpire shortages. And I raised my hand one day and I said, if you give me a bunch of kids, I could teach them how to umpire, probably better than the adults. And long story short, they took me up on it and it ended up working out great where I did this youth umpire program. The problem which I also write about in "Too Smart to Be an Umpire." Because of complex issues in our society, these youth umpires are being physically assaulted, verbally abused, and there's a shortage of officials all over the country. It's part of the reason why we do what we do. Right, because who would want to do that?

00:29:12

Yeah.

00:29:12

It's frickin' insane. You're having 13-year-old kids under their mask crying because a grandparent is showing their kid, their grandchild, how much they love them.

00:29:21

I can imagine. So my kids play baseball.

00:29:24

Oh, do they?

00:29:25

One of mine, yeah.

00:29:27

But it's a great, it's a great, it's a great game. But it is. I did it to give back. And, you know, I fell in love again with the game of baseball again. Coaching a 14-year-old state championship team was a great thrill. So I did fall in love with the game after we were out of favor for a while there. But, but, but, but anyway, that's what, that's what we did.

00:29:48

Do you disclose who your favorite team is or would that not be very umpire-y of you?

00:29:52

I'm a fan of the game. I follow the Yankees. You know, you end up hating everybody because how much they yell at you.

00:30:00

I was wondering. Yeah.

00:30:01

People can ask me about players, you know, I can tell them that guy was a good guy, that guy was a jerk. But I follow the Yankees. But I could follow a Little League team, a game in the Dominican Republic. I'm a fan of the sport. I can watch a game. Watching a baseball game with me is so much different than it is with most other people because I know— I think it would be fun. The coach should have been doing, how cutoffs work, you know, where the umpire in a two-man system should have been.

00:30:27

Like, oh yeah, I mean, you know the game better than anyone, probably.

00:30:30

Yeah, I know that game. I wish I knew golf as well as I did baseball. But, but, um, but, uh, yeah, it's, it's like a religion. Baseball is always like a religion to me. I love the game very much. It's been very good to me.

00:30:41

I love that. So we know kind of where you are with, um, your wealth, wealth management company. We know then you got bored, you wrote a book. So what are you working on right now that you're most excited about?

00:30:54

So right now I'm, I'm simply doing what I advise my clients to do, and that's take the first year and just go slow. Whatever opportunities come my way, I'm willing to do. But I'm interested in giving back, whether it's through these podcasts, maybe another book, I don't know. But I just want to give back. I don't want any set schedule. I like being able to play golf and pickleball. And, you know, I had zero grandchildren a year ago. I have three children. Within 10 months, all three of them had their first child. So we've gone from zero to three grandchildren.

00:31:26

Oh, that's amazing. Congrats. Yeah.

00:31:28

I love that. Thank you. In a year. So I want to spend some time with them too. And my wife and I like to travel. We spent, we spent 7 weeks in Australia, Vietnam, Singapore, New Zealand. So we've done a lot. A lot of traveling, and so I'm keeping an open schedule. But, but I, but I, you know, I'm open to some opportunities, but they're on a selective basis, that's for sure.

00:31:54

Yeah, no, that makes sense. I hope you enjoy it. That's— you've earned it. So that's amazing. So thank you so much, Jack. Last question. What does it mean to you to be a business MVP?

00:32:05

It, it's very gratifying. I think, I think success in, in life is having— for me, it's having adult children that want to spend time with you. But in business, I think it's being respected by your peer group. As an umpire, I wanted to be respected by the other umpires. And in my business, I'm glad I was by the other umpires. And in this profession, to be respected by other advisors, I think that means a lot.

00:32:30

Yeah, I think that's great advice. So thank you so, so much. I've really enjoyed this. Is there, is there anything else that you want to share?

00:32:40

I think you're, you got a lot outta me there, Sammy. I, I really, I really enjoyed talking, talking to you. Um, no, but I think, I think if people, I think if people read the book, they're gonna have a lot of fun with it. And I think they're gonna, they're, if they will definitely get some things out of it that they can use in their life from a practical point of view. Yeah.

00:32:57

And that's how champions think. Here are the key takeaways from my conversation with Jack today. Make the right call even when everyone in the room disagrees with you. That's leadership. You get to decide what defines you. Someone else's words can either tear you down or become the thing you build your story around. And you don't need anyone's permission or anyone's client list to build something extraordinary. You need discipline, trust, and time. If you got value from today's episode, share it with someone who's ready to think bigger, compete harder, and win in business. Make sure you're subscribed so you never miss an episode. And if you haven't, leaving a 5-star review goes a long way in helping us grow and reach more leaders like you. I'm Sammie Pedersen. Thanks for being part of the Business MVP Community, and I'll see you next time as we continue building you into an MVP in business and in life.

Episode description

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. Instead of letting rejection define him, he used it as fuel to reinvent himself, eventually building one of the nation's leading tax-focused wealth management firms with more than $800 million in assets. In this episode, Jack joins Sammy to share the lessons baseball taught him about pressure, decision-making, mentorship, customer experience, and why doing the right thing consistently became the foundation of both his business success and personal fulfillment.

In this episode, Sammy and Jack will discuss:

(00:00) Introduction

(02:19) The Umpire Lessons That Built a Business

(05:59) Why Every Athlete Needs a Second Plan

(10:34) The Risk Strategy That Grew an $800M Business

(16:48) The Hardest Decision Every Founder Faces

(21:03) The Reinvention Formula For Life After Rejection 

(27:36) Giving Back to the Game That Cut Him

Jack Oujo is the founder of Oujo Wealth Strategies, a nationally recognized wealth management firm overseeing more than $800 million in assets. A former professional baseball umpire and author of Too Smart to Be an Umpire!, he is known for helping clients build wealth through disciplined planning, risk management, and long-term thinking.

Resources Mentioned:

Jack’s Book, Too Smart to Be an Umpire!:
https://www.amazon.com/Too-Smart-Umpire-Jack-Oujo/dp/1506915329

The Power of Negative Thinking: An Unconventional Approach to Achieving Positive Results by Bob Knight with Bob Hammel: https://www.amazon.com/dp/054402771X 

Connect with Jack: 

Jack’s Instagram: https://www.instagram.com/jackoujo/ 

Jack’s LinkedIn: https://www.linkedin.com/in/jack-oujo-cpa-cfp-ms-tax-97906810/ 

Too Smart to be an Umpire! Website: https://toosmarttobeanumpire.com

Oujo Wealth Strategies: https://www.oujowealthstrategies.com

Connect With Sammy: 

Instagram: ⁠https://www.instagram.com/businessmvppodcast/⁠ 

LinkedIn: ⁠https://www.linkedin.com/in/samantha-peterson-0442586/⁠

YouTube: https://www.youtube.com/@businessmvppodcast

Become a Business MVP:

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Join Sammy Peterson today at www.theentrepreneursboardroom.com