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How Jack Oujo Turned a Career Setback Into a Business Success Story
Introduction
Hello again everyone. This is Doug Thorpe, and today we’re going to ask you the question. If you have had or may have a personal setback in your career, what are you going to do with it? How do you think it will impact you? Or maybe you already know and you’re still struggling with that?
My guest today has an incredibly interesting story. He had aspirations to be a professional baseball umpire, and it didn’t all work out. And he subsequently wrote a book about it called Too Smart to Be an Umpire. I’m going to love to dig into that and see what that’s about. But my guest is Jack. Jack, I failed to ask you how to properly pronounce your last name.
It’s Oujo, Doug and Oujo.
Okay, I would have gone there, but I should have asked. But you’ll see his name in print, folks. You’ll know why I struggled with it a little bit.
But anyway, Jack, welcome to the show.
Thanks for having me on, Doug.

Where Did the Title Come From?
I’ve got to lead off with the basic question why the title? Too smart to be an umpire. Where did that come from?
Yeah, it came reluctantly, because I have too much respect for the umpiring profession to actually think that’s how I felt about it, but I came from all when I wrote the book Too smart to be an umpire. It was always called plan B. All my files are saved as plan B, and I wrote a chapter about my last year when I was in Triple-A.
I was umpiring at the old Rosenblatt Stadium in Omaha, Nebraska, where they played the College World Series for many years. And I was being observed by Dick Butler, a supervisor of umpires with the American League. And when the game ended, we went out to dinner and I asked if he could give me a critique on my work because I was trying to decide whether to move on with my life or not. And he goes, Jack, I think you call a really good game.
He goes, I like the way you work. To be perfectly honest with him, I think you’re too smart to be an umpire. And and I and I was dumbfounded. I go, what? I’m too smart to be an umpire. That’s a defect. And when the publisher saw that and the editor saw it, they go that. That’s got to be the title of your book right there. So it came from Major League Baseball, not from me, but that but that’s where the title of the book comes from.
Did he ever elaborate on why he was saying that?
No. And you know, when you’re an umpire, especially back then where there wasn’t technology like there is today, it’s a very subjective decision on who gets to the big leagues. And I realized I was signing in for that. I like to say it’s like watching Miss America on TV, you know, they’re all beautiful women, but we might have a difference of opinion. Or it’s like asking an appellate judge why they never got on the Supreme Court that funnel, especially back then, because there was only 52 umpires back then.
Now there’s like 100, but the funnel gets very small as you get to the big leagues. So the worst thing that can happen is what happened to me spending eight years in the minor leagues between the ages of 22 and 30, and then having nothing to show for it. If you do a year or two in the minor leagues, it’s no big deal. But I did eight seasons plus six winter balls, so it’s kind of like a life sentence there before I had to move on.
The Door Slams: Facing the Release
Yeah. So you had great aspirations of of letting that be a career. And when the reality of the door slamming on that opportunity, talk a little bit about your particular journey there in the in the immediate action and reaction to all of that.
Sure. So I had an accounting degree. I officiated my way through college. I graduated from Seton Hall University, so I officiated my way through school, and I only went to umpire school just to get it out of my system. I had an accounting degree, and I was smart enough to work as an account in the off seasons in New York City.
So there was kind of, you know, a plan B that that was building up when I did get my release, which I was surprised to get when it when it did come, my wife and I put a plan together of attack, and we decided that we were going to invest about four years of my life in getting as much education as I could get. I was greatly influenced by a book written by former Chrysler chairman Lee Iacocca. Back in the day, I was in the Dominican Republic when I read this book, Winter League, and he said, to get as much education as you can and then do something with it.
So I immediately got a job with Ernst and Young. I knew they e now. I pounded on the door, I knew they did the audit for Major League Baseball, and they hired an umpire, a minor league umpire, for eight years to be a tax accountant. And within that four year period of time, I passed all four parts of the CPA exam in one sitting the Certified Financial Planner exams.
I got a master’s degree in taxation. I got securities license and insurance license. It was like, all right, well, I had this skill set now. Now I have to do something with it. So the the, the way of dealing with the hurt from the release, because I realized that I was going through a depression at the time, I decided to I was self aware that I’m going to try to spin this lemon into lemonade by not feeling sorry for myself and just engrossing myself and work in education. And that’s what I did. That led to something very special.
Identity and the Weight of What Was Lost
How much of your personal identity was wrapped up underneath? You know, the umpire gear?
There was a lot. There’s there’s a lot of personal identity. You know, when you’re a sports official, it’s kind of like a religious type of thing, almost like it’s it’s not just a game. It’s it’s like a calling. And so especially when you’re in professional sports, seeing that mail, the checks coming in from professional baseball.
It’s an honor to to be in that game. And when it’s all taken away, which you realize and again, you sign in for that this this can happen when it’s taken away. Oh, you know, your relatives aren’t getting free tickets to the games anymore. And boy, I wish I could have known somebody in the major leagues and it it’s almost in now. I don’t feel embarrassed by it, but at the time it’s humiliating and especially for an umpire.
You’re thinking, well, the guys on TV aren’t that good. You must not have been very good if they got rid of you. That’s kind of a knee jerk reaction that people are thinking. Even though the people in the major leagues are pretty awesome at what they do. So yeah, your identity is tied up and it takes a long time to get over that. It takes a it took me a long time to, to to get past it. In my particular case, my life ended up being pretty awesome. And in my case, it was definitely a blessing in disguise.
But for a lot of other people, they had a lot of trouble getting past that. Yeah.
A Shared Experience: When the Door Closes Without Warning
I had a I pause it saying similar. But I had one of those career moments where for 15 years I had been a manager in a great organization and had had consecutive, you know, growth opportunities at that level. And then all of a sudden one day they walked in my office and they said, you’re not going to run this unit anymore. We’re we’re going to make some changes and we’re we’re going elsewhere.
And I kept asking why. And they would say, no particular reason. We’re just making the change. And I, you know, went all the way to top of the House senior management. And I said, I’m a big boy. I’m I’m promise you I’m not going to sue over this. So just tell me why. What what do I need to know about this decision so that I can be a better person for it? And they wouldn’t tell me, you know, so it’s like, okay, well, now I got to go redefine and repurpose.
It’s very difficult. You know, now that I’m on the other side of it as an employer, I remember I’m really not good at firing employees. It was tough to get fired by me because I really tried to make it work, but I was always advised by legal counsel that when you let somebody go, just say it’s not working out because we’re in employment at will state. When you start giving answers, you’re more likely to get sued.
And when I was released from baseball, I was looking for those answers. And the attorney for professional baseball was a guy named Charlie Crist, who went on to become governor of Florida. And he wrote me a letter saying, we are we are not going to give that to you. And I write in the book how I eventually did see my ratings. And it was it was it took four years of being out of baseball before I, I saw my ratings. And that’s only because somebody else filed a lawsuit. And I saw him at the deposition. So it’s tough to take when you don’t know why.
Like, why is somebody making this decision and people are reluctant to tell you, I guess.
Yeah, I get that certainly from a legal and I agree as an employer there, there is high liability if you get into any details about things. But, you know, on a personal level, if you are willing to be a little bit of self-respect or reflective, I should say, you want to know why? So you can try to springboard that. But but the point being, oftentimes you’re never going to know. So it’s a futile effort to go seek it. And and don’t camp out on that idea. Just move on.
Yeah. I, I when I look at myself in baseball, if I was trying to make a case for why I did not get to the major leagues, I would say it was because I had not developed a style that was consistent with what the supervisors were looking for. I placed the blame on professional baseball for for not making those things clear.
I think I ran. Funny. Which you think. Who runs? The last time you watched an umpire and critiqued them on how they run? But when you’re evaluating people for the final legs, I think you look at that. I think my appearance on the field could have been better. So I self-reflect and think, what could I have done better? Okay, to reach that final level?
Having said that, I felt that if I was good enough to make it to triple A and have a real shot at the Major Leagues two. By the way, not like I was getting buried in triple A, if I could take that to the business world, your chances of being successful in business are far greater than they are of professional sports. Like. Like, every coach that loses will have a speech that says something along the lines of it’s okay to lose if you learn from the loss, but it’s never okay to lose if you don’t learn from the loss.
So when you lose and you can take lessons that you learned, you start winning all of a sudden and you start winning on a consistent basis, and I learned that I had a skill set where I knew how to deal with people on their worst behavior.
I knew how to do the right thing in the in the face of tremendous amount of adversity. I knew that I, being on the field with superstar athletes, said they were human beings, just like the rest of us. That had to work hard and smart. And I’m going to take these things now in the business and apply them. And I think these should work. And they did. And in the business community, I became the number one advisor with my firm for over a decade.
And a lot of people in business don’t know my background in sports, and it’s something I didn’t talk about very often. It’s one of the reasons why I wrote the book. People that love baseball, you know, can hear the war stories of managers getting thrown out of games and then the reinvention process. What does it take to start a business with $0? Have I had a negative net worth actually, and then grow that and and do well with it? How does all that work?
Better or Bitter? The Choice That Defines Everything
Yeah. The whole idea of dwelling on the experience in a negative way and not learning from it.
I ask clients who start expressing that conundrum is the basic question do you want to be better or better? And you can carry that negativity with you and it will. It will erode everything else you might think of pursuing. Or you can find the learning. Apply that and move on.
A lot of people ask me, what’s the most important thing when you’re trying to overcome these things. And the most important thing at the top of the list is your own personal attitude. You have to get over this hurt and bitterness and dust yourself off and and really have a good attitude because you just got beat up, you just got fired or you weren’t promoted or whatever, and now you have to do something else, and you better have a core belief in yourself and, and have a supportive spouse, and I think it helps to have a relationship with your creator and and hopefully supportive children.
You need all these people in your life if you want to go from there and do well, in my opinion.
The 66/33 Split: Who Makes It Through a Setback
Right? Yeah.
I’ve talked often about my experience in the 2008 timeframe, with the big recession and crash that happened, and running a nonprofit for job seekers trying to help people on the other side of that event who had lost jobs. Most most of my participants in my program, that was the first time ever in their career they had lost a job because they they were high performers. They were motivated. They they were good workers.
But because of the economic condition, their company just cut deep and in most cases were cutting muscle, not just fat. And good people got let go and were put on the streets. So having the identity crisis was a big issue. And finding that new sense of purpose and rebuilding the very personal level of confidence to go out there and try again. And it was interesting. I’ve talked about this. I had some hard data that we collected through the process. We ended up coaching over a 3 or 4 year period. We coached about 4500 individuals through this transition, and there was an interesting data we never could get away from.
66% of our participants were successful in moving on. 33% were not. And when you did deeper analysis name by name, you realized that the 33% that could not make it out of the funk had internalized everything in a very negative way. They had not found a way to turn the lemons into lemonade and they, you know, went on. They gave up on what we were coaching and teaching and tried something else. And I don’t know what their industry was ultimately, but the 66% that took it positively and figured it out, you know, did well.
And a lot of times I think people make the mistake. These people that might be in a 33% group one are looking at their experience where they did five to 20 or 30 years, whatever it is in their other career or other job, and all of us all of a sudden want to start at the top of whatever it is that they’re going into. And I think a lot of times people need to retrain themselves like I had to do, and go back and get their own equipment in order and meaning.
The equipment I’m defining as your skill set, so that you could take it to the marketplace and do well. And and as a financial advisor, I’ve seen it over my whole career because I have people coming in like a parade, okay, that have been let go. The old story that private equity bought their firm, and they were one of the people cut out of their jobs, and now they need to roll over their four one K and figure out their money and things along those lines.
I’ve, I heard that once a month during my whole career of what’s going on in the world, and I tried to be like, Anthony Robbins, like, you need to you need to get your attitude right and get your approach right in order to be, because these last 10 or 20 years of your career are going to be critical to build up the lump sum of capital you need for your own financial independence. So it becomes a very big deal, especially for people later on in life.
Practical Steps for Reinvention
Yeah, well, you know, you’ve touched on so many good things, Jack, you know, sort of redefining the wheel, if you will, and and collecting the necessary tools and equipment to move forward.
You touched on the number one top of the heap is the mental attitude about it. Anything else we’ve left off of that scope so far.
Sure, there’s tons of things. So so you have the attitude, the equipment, meaning your skill set. In no particular order. I would seek out people that are in a field that you want to be in or aspire to be in, and get their feedback first before you venture into something. Be a pest. Ask questions. To this day, I have college students probably once a month that somehow find me and reach out looking for advice. X people in professional sports reach out looking for advice. You’re like the poster child I had to move on with with your career.
So? So I think that’s very important. I think having a written plan of of what you want to do using math. So whatever it is that you want to go into, you need to look at the next 10 or 20 years of your life. What is the income you expect to be getting from this? What are your expenses? This is for people that want to go into their own business or consulting gig, if you will.
How does the math work on this? And when you draw that plan, it will become self-evident whether or not you should undertake your your particular plan or not. That’s how I went into business. My partner and I borrowed on credit cards to start our business. It sounds insane, but we had a written plan, and we figured if we could pick up two clients a month for two years, we should have enough money to not only pay off our debt, but make a sustainable living for ourselves. It’s with no money and just borrowing on credit cards to start a business. It sounds insane, but. But it worked.
So? So I think writing things down, getting your equipment, seeking mentorship, all those things, all those things matter. Doug.
The Power of Asking for Help
Great advice. And, you know, particularly the one on reaching out to others, I think so, so many times people are still struggling on the personal side, feeling a little bit embarrassed about what caused the transition. And they’re afraid of reaching out to people because people will say, well, why are you asking what happened? You know why? Why would this be a possibility? You got to get over that.
I mean, they might, but, you know, you need to create your own truth about what that meant and what the story was. And by the way, it it can’t sound like sour grapes when you tell it.
I found that successful people in the world were willing to share information. There’s there’s billionaires out there that that are willing to give out their advice, and people are willing to help you. Everybody has a favorite subject that’s themselves. Asking successful people how they got to where they are. Most people are happy to help with that. It doesn’t cost anything. You’re doing something good for people, so ask. I’m shocked how people don’t ask.
I remember when I went into the financial advice business at the time, I called our broker dealer and I said, can I ask you who is the best advisor in the firm? Doesn’t have to be the number one producer, which I became, but who was the best adviser? And they go, oh, that’s a guy in North Carolina named John Rudd.
And I go, all right, I’m going to find this John Rudd. And I called him up and I asked him to fly up to new Jersey at my expense, and I had him sit down and show me all his equipment, all his tools. How did how did he do everything? And I said, thank you. You just spent you just took away five years of a learning curve for me.
Okay? This is who they thought the best advisor in the firm to flew up to new Jersey to show me what he knew. That’s how much people were willing to help you. And I asked him, how many other people have asked you? He goes, nobody, nobody. Okay, so when I was at number one advisor in my firm, some people called. How did how did you do that? But not a lot. Okay. And if anybody and anybody did call, I was always willing to help them. So people are there, you know, ask, be it be a pest, ask for advice.
Yeah.
I agree with you. And I encourage my own clients to seek mentorship, either within the company they’re in or outside. And they say, well, you know, the people I’d want to talk to. I know they’re crazy busy. Well guess what? Go ask. You know, and the the thing I try to tell people, try to be specific. You were specific when you asked that guy. You know, I mean, yes, it was about his whole game, but you had a specificity about it and he was willing to share.
People are going to do that. Good people know they got there on the shoulders of others. So there, if they’ve been successful, 99 out of 100, they’re going to want to give back. They’re going to want to it’s not pay it forward, but it’s pay it back. And they’re willing to do that.
Connecting the Dots: Jack’s Kids and the Next Generation
I think of two of my children. Okay, a very quick example. My daughter went to George Washington University and Columbia, and I was all over her to get internships in government, and she did them.
And today she’s the Energy Department’s attache at the US Embassy in Beijing, China, representing our country. My middle child was into aviation. He’s always on those stupid flight simulator games. We brought in airline pilots. And my wife and I would leave the room for him to get advice on becoming an airline pilot. He became a captain at Alaska Airlines when he was 32 years of age. Okay, bye. By asking get. Get in the game.
Find out whatever it is you want to do in life. Find out from other people had. What did they do? And they’ll help you connect the dots. I think it’s the two guys. I just sold my business to two of our employees. The two employees ask questions. What do I need to do to be sitting in your chair someday? Tell me what to do. And I go, here. You connect these dots. You can have a nice life for yourself. They connected the dots. They now own the business.
And when I wrote Too smart to be an umpire, I. I put the dots in there for people to connect, for them to be successful in their own lives. It’s it’s designed to be an inspiring book to help people in business and and get over hurts that have taken place in their lives and what the formula for success is.
You. You know, in sports. Another thing from sports, I took out anybody in sports that wins and talks about winning has a process. Nick Saban talks about process. When I was calling balls and strikes, I had a process for calling balls and strikes. When I started my business, I put processes in for an initial client meeting service, follow up, dealing with unusual events that happen in the world, processes for everything.
There was never a meeting with our staff like our goals to increase sales 10% this year, our goal is to be the number one advisor. Our goal was always to refine our fricking process, get our process down, and if we do that, wins will be the result. And and that’s what I think people in business need to do.
People need to do it in their own lives. Instead of rah rah speeches. Work smart, develop good study habits, things along those lines. That’s how you win in life, in my opinion.
Entrepreneurial Roadblocks: What Holds Business Owners Back
Jack, for the clients you’ve had that are entrepreneurs and have built their own businesses over time. What are some of the typical roadblocks you watch those people share with you about, you know, where they’re struggling with what they’re trying to do different?
One of the biggest struggles I see, and it’s from people with the best of intentions, is that they’re doing all the work themselves, rather than hiring that first employee. When you go into your own business, hiring the first employees. A big deal because it’s a step back in your own pay, and now you’re relying on other people to do things. Okay. And a lot of people just can’t let go of that.
Okay. My brother’s an electrician. I think my brother could have retired 15 years ago if he would have hired other electricians, rather than just being an electrician himself.
My dad was like that. Never hired anybody. Only Dominic the Great can be the the electrician around here. And you saw it with the McDonald’s brothers. You know, they became a Dow 30 company. They thought they were the only ones capable of making the freaking hamburgers. Okay, so doing too many things themselves, not having processes in place.
And I think a lot of people go into businesses where they need lines of credit, like anybody that has inventory and has to sell their inventory and wait to collect money, they don’t understand how cash flow works. And again, just not having a business plan. People that don’t plan out their cash flow make mistakes. And I think a lot of people need partners, whether it be working partners or financial partners. Think about every publicly traded stock. The only reason they’re publicly traded is they needed more money. They took on investors. So people need to understand how their business may grow. How does it grow, how does that work? And they need to outline it in writing.
My my business I always had a budget for the future, okay? And I’d have fun with it. What if sales go down 20%? Up 30%? How does that work? What do I need to do? How do I get in front of those things? I think people in business will have more business than they know what to do it. If they create excellent service models where, like my business grew, I’m 100% convinced is because I try to create an overwhelmingly positive level of service where I created raving fans who became advocates for my practice.
Again, I was the number one salesman in our firm. I don’t consider myself a salesman. I consider myself a nerdy, freaking accountant. But I needed these other people to go out and sell. You got to go see Jack or Anthony or Jason in my office for financial advice. And that worked. You know, returning a phone call, turning an email. Okay. Returning it on a weekend, returning it at night. Okay, is great.
Public relations for your business. It’s just common sense things that people need to do. In my view. Doug.
The Delegation Trap: Learning to Let Go
Yeah. I’ll end. You did touch on this. The idea of the owner founder feeling like they need to do everything and they can’t quite let go of certain things. And I saw that in my own banking days with clients who had great ideas, great products, services, and they were generating good volume, but then they would inevitably scale up to a some level, some plateau that they couldn’t break through.
And it was inevitably the lid on the business was caused by the founder that not not being willing to delegate and hire out and expand with infrastructure in the business, that could could make that happen. And to your point, sometimes the cap was related to a failed or missing process. They were still doing everything on the fly, and you can only recreate the wheel so many times until you burn out. And you, you have to get it defined into a scalable, repeatable process that will hit your goals and marks.
And I’m sure your processes in your business were oriented to that exceptional service. And so when you found something in your process that was a a roadblock or a hindrance, I bet you pretty quickly got rid of that or refined everything.
It’s a very fluid situation you’re trying to get. I always said to the people in my office, we’re trying to get to this place we’re never going to get to, okay? We’re trying to we’re trying to achieve perfection, Vince Lombardi said. When trying to achieve perfection, you achieve excellence. So this attitude of trying to get to this place where there’s perfect service, perfect clients, you you try to get there. You do the best that that you can.
I found it a lot of fun. I remember my partner came in one day, and I was working on a Sunday at 11:00 in the morning doing tax returns. And he goes to me. Me and you were the two biggest R’s in the world. We need to go out and hire people. We got to stop doing this.
And we made another mistake by hiring the lowest paid employees. And that turned out to be a disaster. And we learned that it’s cheaper to hire the best people. And we hired all these great people hiring people smarter than us, people that complimented our personality. It was a big step back in business and a very ballsy decision. But on the other side of that, the business just took off. Okay. We were hiring these great people and who just loved their jobs.
And I mean two people, Anna Michael and Loretta Sohan worked with me for 25, 30 years, their whole careers, and it was a great accountant. And Loretta had a great personality in dealing with people. And just from those two core people. We ended up, you know, at the time of my retirement, had 15 employees and $800 million under management.
So it ended up, you know, being a lot. If somebody would have told me when I was doing tax returns on the side in the last 15 years of your career, you will not personally do a tax return.
Okay. I would say you’re out of your mind. Only I can do these tax returns and you find out other people can do them. You got to create these processes over time that that work for the business owner. Like my brother, the electrician. He doesn’t have to be doing putting wires together. Other people can do that and he just can’t get past that. My father couldn’t get past that.
And I kind of saw the mistakes that they were making in business. And I was like, I’m not going to be like that. I got to figure this thing out in a smart way. There’s a good book besides my book, Too Smart to Be an Umpire. There’s another good book on that called the which you probably know, Doug The Myth by Michael Gerber. Now it’s the E myth revisited on why most small businesses fail.
And that book influenced me a lot because when he when the author was talking about when Michael Gerber was talking about the the bad business owner, I was like, that’s me.
That’s that’s me, and I, and I learned to work on my business rather than in my business so much. I got to the point where I was only dealing with clients, meetings with clients. Somebody else was doing the preparation. All these systems that I was putting in place, I had other people doing that sort of thing, and they loved it. And we had a great culture and we had a lot of fun. So that’s what you’re looking for.
Closing Thoughts and How to Connect with Jack
Well, Jack, I think we’re about up on time. Thank you so much for sharing this. Tell people the best way to get in touch if if they are interested in knowing more about you or the book.
Sure, Doug. They can go on. There’s a website too smart to be an umpire. Com on Amazon or Barnes and Noble. If somebody goes on their site, they’ll see all the reviews. It just became a top ten bestseller within its category on Amazon, so I’m thrilled with that. And then Ojo. Well.
Strategies. Ojo. There’s not too many of us in the world. People wanted to look me up. They could find about our business and they can email me if they want to get in touch with me.
That’s great. Well, as always, folks will have those links in the show notes, so do feel free to check that out. And I like to remind you, we’ve got a video version of this show on YouTube. It is a channel by the same name. Leadership powered by common sense. Hop over there. Join the channel if you will. Leave us some comments. Let me know what you think. And if you’ve got any ideas for future topics, we’d love to hear from you. But for now, I’m going to sign off. Say goodbye. Go out there and make it a great day.
Meet Our Guest
Jack Oujo CPA/PFS, CFP®, MS, author of TOO SMART TO BE AN UMPIRE, 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.
His website is: https://toosmarttobeanumpire.com/
His LinkedIn is: https://www.linkedin.com/in/jack-oujo-cpa-cfp-ms-tax-97906810/
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