191: Jack Oujo - How A Released Umpire Built Financial Independence Through A Written Plan

Jack’s career didn’t end on his terms.

It ended with a letter.

No warning.
No backup plan.
No income.

Just a moment where everything he had built… stopped.

In this episode, Ryan sits down with Jack to unpack what it really takes to rebuild your life after sport when you’re forced to start again.

From surviving the brutal, cutthroat world of professional umpiring to being released with nothing, Jack shares how he turned one of the hardest moments of his life into the foundation for a multimillion-dollar business. 

What You’ll Hear in This Episode

- The reality of chasing a professional sports career (and how few make it) 

- What it feels like to be cut without warning 

- How Jack turned frustration into a clear plan 

- Why writing things down changed everything 

- The simple math behind building a successful business 

- Why athletes must stop expecting to “start at the top” 

- The importance of starting from zero and earning your way up 

- How discipline from sport translates into business success 

- Why most people don’t prepare for worst-case scenarios 

- The mindset shift from athlete to business owner 

This episode is about ownership.

Not of a business…
 but of your next move.

Jack didn’t wait for someone to show him what to do next.

He sat down, faced reality, and built a plan.
 Even when he didn’t know exactly where it would lead. 

And that’s the difference.

Because most people stay stuck in the moment.
 He used it.

Want to go deeper?
If you are looking for career clarity for your next step, visit www.2ndwind.io
to learn more or book a consult.

Transcript

Knowing When To Sell

SPEAKER_01 0:00

How did you know it was time to exit the business, to sell the business?

SPEAKER_00 0:05

I was watching the progression of the people I had in my office. I saw the two guys I was mentoring really go to another level. And I saw them chomping at the bit. My finances were in really good shape. And I said to them when we got to 2024 and 2025, I said, you are now in a position to own the business, but I want you to do it for two years. Still going to be under my in my name, but I want you to run it as though it's yours. You have the power to hire and fire, make any decisions that you want as long as they're reasonable. And let's see how things go.

SPEAKER_01 0:44

Hi, I'm Ryan Gonzalvert, and welcome to the Second Wind Academy Podcast. A show all about career transition through the lens of elite athletes. Each week, I invite a guest to the show who shares their unique sporting story. Please join me to delve into the thoughts and actions of athletes through a series of conversations. Don't worry, there's plenty to learn from those of you that aren't particularly sporty. Elite athletes are still people after sport. Let's be inspired by the stories of others. Jack, thanks for joining me on the show today. It's great to have you on. Looking forward to hearing a bit more about, well, you know, your career and the transitions that you have gone through and sort of some of the things you did to navigate it as well. So thanks for joining me today.

SPEAKER_00 1:34

It's my pleasure to be with you today, Ryan.

SPEAKER_01 1:36

Excellent. Well, we're gonna we're gonna jump in because you've got quite a fascinating background. But for those who don't know who Jack Ojo is, just give us that 30-second brief. Who are you, you, and what are you up to nowadays?

SPEAKER_00 1:48

The story in my book, Too Smart to Be an Umpire, is I I graduated from Seton Hall University in New Jersey with an accounting degree, and I officiated my way through college. I played baseball in high school a little bit my freshman year in college, but I needed money. So I was encouraged to try officiating, and I became pretty good at it. And when I graduated from college, not wanting to have any regrets, I went to a professional umpire school in uh in St. Petersburg, Florida, and they took me into the minor leagues, and what I thought would be a very short experience in the minor leagues turned out to be eight years. And by the time I was 30, uh I ended up getting released. Um they had a policy, if you had three years in AAA and the major leagues didn't take you, they got rid of you. In retrospect, I got to AAA uh too quick, probably, because there's people that went to the major leagues that I beat to lower levels of the minor leagues. And I found myself with a pregnant wife, no money, and uh having to start a career. And um, I ended up creating a multimillion dollar financial advisory business that I just sold to two of our employees and uh achieved success in the business world that I could have never imagined.

Umpire School And The Funnel

SPEAKER_01 3:06

Well, that is a great summation of of the story. So thanks for that. It really does paint a picture and sort of signposts uh the well, I'm gonna have to cut down the hundred questions I've got, or else we just won't get through it. But it certainly gives me a good um, I'm gonna say, ballpark in in which to begin. And I'm gonna start with Umpire School.

SPEAKER_00 3:27

What is Umpire School? It's it's a way, if you think about Major League Baseball, they have to develop officials. So the Umpire School is more of a try-out camp. People came there with some level of experience, generally speaking. Not always, but in most cases they did. And Umpire School was a five-week camp that started at nine o'clock in the morning with classroom study. And then they took you out onto the field and they put you through various situations that take place in baseball games. They put you in batting cages to see your judgment on calling balls and strikes. And when I went, there was about 350 people that went, and they ended up hiring 13 people out of 350 people. So you had to be at the very top of the class. And then as people quit or got fired during the season, they might have another 15 or so openings. So by the end of the first season, there was probably 30 people that were taken into the minor leagues. And once you got into the minor leagues in baseball, and the way it works is there's um low A, high A, double A, triple A, then the major leagues. At the end of every season, about 50 to 70 percent of all the umpires were fired at the end of the season because they keep rotating people in. And um it was like a game of survivor. You know, at the end of every year, you're happy not to be fired. And it's cutthroat, it's rigorous, and um, it's not easy. It's not as easy as people might think it is. It's it's a funnel you're trying to get to to get to the major leagues, and it's a very narrow funnel at the end.

SPEAKER_01 5:07

Yeah, it it is. So tell me then, umpires, when I think of baseball, I there are umpires all around the field, right? So I think there is there's more than just one. So when we're talking about umpire here, aren't you a team?

SPEAKER_00 5:20

You are you are a team, but there's one umpire behind home plate galling balls and strikes. That's where the value is, if you will. That's obviously the most important position. In the minor leagues, there are only two umpires. In the major leagues, there's four and there's six during major events like uh the World Series, if you will. So uh you rotate around. If you have home plate one day, the next day you're at third base, then second base, then first base, and you switch around. Obviously, the role of an umpire today is a lot less important because of technology. I mean, if you could tell if a pitch is a ball or a strike with your phone uh or safer out with your phone, the human being uh is less valuable. Artificial intelligence, in my view, will take over a great deal of that job as as time goes on, in my view.

SPEAKER_01 6:13

Okay. I mean, so it's so it's individual, is what I'm getting. So you might be part of a team, but for you as an umpire, you're trying to get yourself on that that home plate. So, but for you, you know, you you became an umpire. I'm gonna say not through design, but as a way to fund yourself through university or through your your college education, right?

SPEAKER_00 6:37

Yes, it was uh it was a part-time job. When I was growing up, I lived next, my next door neighbor was a guy named Ed Sanickey, and he played for the Philadelphia Phillies and hit three home runs and 20 Major League at bats, and he was an umpire as a hobby, and he encouraged me, you ought to try umpiring, uh, because I was a catcher when I was a baseball player, which is also right behind the plate. He goes, You'd be very good at it. And I thought he was crazy. I'm like, you're gonna get yelled at all the time. And he goes, Well, you can make good money at it, it's better than most part-time jobs. So I took his advice and I tried it. I ended up liking it very much. And I found that when I was in college, I was getting all these top games. I was working state finals, um, I kept getting promoted, and and I was and I was having fun. And so I had an accounting degree, and I figured I'm young. If if I don't make it, I can still fall back on my accounting degree, which I did. And um there, there's plenty of time in life to you know, chase your dreams when you're in your in your 20s. Plus, I got to see a lot of the United States. I got to travel. When I was a kid, I never traveled, and we never traveled anywhere, we had no money. So uh so that that's why I went into it. And it was it was fun. People thinking just getting yelled at and abused, it's a lot of fun.

SPEAKER_01 7:53

It was a lot well, you know what what intrigues me really is because my one of my boys, he is a a referee um in rugby. And so I I see him going out, so he still plays, but I, you know, can realistically see him and there's other sort of um grown adults who are doing refereeing and and they see it as a as a a part-time pathway. But for a few, they see this as a full-time opportunity. So for you, you know, as you came through with that degree and you thought, let me give this a chance. Tell me, what did you think being a full-time umpire could be? Like, where did you I'm assuming you wanted to get into the major league?

SPEAKER_00 8:37

Yeah, you obviously want to get to the major leagues. You don't there's no money, there's poverty, if you will, by being a part-time official, if you will, or certainly in the minor leagues in American sports, uh the players, the umpires, uh are in poverty. There's no money. So you're hoping it's not a very long road in in the minor leagues so you can do something else with your with your life. At best, it's a part-time job. In Major League Baseball, the Major League Umpires are paid anywhere from$200,000 to$500,000 a year. Um I I know how much money they make because when I when I became an accountant later, they all became a third of them became clients of mine. So so I have I played golf with three uh retired Major League umpires the other day. Um so I'm I'm still friends with with a lot of a lot with a lot of people. And they also receive a very good pension. And um so it's a very good full-time job. Um, but it's no place the minor leagues is no place to be over the longer term.

SPEAKER_01 9:36

So when you talk about being too smart to be an umpire, what do you you know, you talk through that in the book. What you know sort of break that down for me a little bit more.

SPEAKER_00 9:45

Well, when I wrote when I wrote the book, all all my files were saved as Plan B. It was always called plan B, transitioning from sports to book. And I told a story in the book where I was getting evaluated when I was in AAA by uh by a fellow named Dick Butler, who was this used to be the supervisor of umpires for the American League. And we had a game at the old um Rosenblatt Stadium in Omaha, Nebraska, where the College World Series was played. When the game was over, he took our crew out to dinner. And I said, Mr. Butler, I've been in the minor leagues for eight years now. Wanted to know if I could get an evaluation and if you could tell me where I stand with you guys. And he said, Jack, I think you call a really good ballgame. He goes, I only disagreed with one pitch. To be honest with you, I think you're too smart to be an umpire. And I was like, Too smart? I'm too, I'm too smart. That's a defect. And um, and he goes, Yeah, I think you're too smart to be an umpire. I think you'd be better off in the business world. I think you can make a lot of money in the business world. You have a good head on your shoulders. So that's where the title comes from. It it came reluctantly from me. The uh media people and the publishers were like, that's the title for the book when I saw that chapter, and I'm like, okay. But uh, but I certain I certainly don't feel like I'm too smart to be an umpire. But uh I guess that that resonates throughout the book, if you will. Um about being able to go into business and do well in business.

SPEAKER_01 11:08

Yeah, I was gonna say, so when you look back at that, because it's something I've heard before from any athletes who are um perhaps studious, academic, not just driven by gut, but plan things out and work them out differently to what an athlete would do. It's funny because I would have thought as an umpire, a referee, that kind of analytical mindset would have been something that would have supported you even better.

SPEAKER_00 11:35

It it does, but in in baseball, you need street smarts and and it can be really rough in professional sports. Maybe that was his way of thinking that I I wasn't tough enough. I certainly feel like I was tough enough. I had a very thick skin and it served me very well in in in the business world. Um, but I think smarts mean a lot, especially in our sport, baseball. Uh base I I wrote I write in Too Smart to be an umpire, how I think in baseball most games are lost, not won. Uh, and a lot of times it's through stupid mistakes, it's through not knowing how to keep your head and control the big inning. And if you look at a baseball game, most teams that lose a game, it's usually because of one bad inning. Uh, there's golfers that lose tournaments because of one bad hole. And um facing adversity in a game in in soccer, if you go down a goal or two and being able to keep your head and being able to press on and perhaps come back and win the game means an awful lot. So I think handling adversity, handling negative events is a pretty big freaking deal. And for an official, if you if you make a bad call in a game and you you wilt under that pressure, um, you're gonna be pretty bad for the rest of the game. So so uh I I think having a good mind to recover from adversity is a pretty important thing, actually.

SPEAKER_01 13:01

I definitely agree. And I think you know, we're gonna get onto that with yourself in terms of what that I guess that transition was like for you, because it wasn't a timed transition. It doesn't, it wasn't one where you had said, okay, I'm done. Um absolutely fantastic. I've achieved everything I want to do. So talk to me a bit about coming into that transition period and what was going through your mind.

SPEAKER_00 13:26

Sure. When when I was released from baseball, I received a letter in the mail with a check mark saying I was released around November of 1988, some time ago. And um when I received the letter, I was I was devastated. I remember being in my bedroom, staring at the ceiling, and thinking I could spend the rest of my life feeling sorry for myself or I could try to find a new path. And the next day, my wife and I sat down and we created a written plan of attack of how we were going to deal with this. And I was greatly influenced by a book I read by former Chrysler Chairman Lee Akoka. And he said for people to be successful in the business world, you need to get as much education as possible and then do something with that education. So, not knowing where things would lead, I ended up getting hired by Ernst ⁇ Young, EY, now rebranded. They hired me. I think they did the audit for Major League Baseball, which helped me get the foot in the door there. And the four-year plan included becoming a certified public accountant, certified financial planner, getting a master's degree in taxation, and getting various licenses in securities and insurance. And I just spent every day working, every weekend, getting uh more professional credentials, which I achieved in three and a half years. That goal was achieved in three and a half years. And then with a partner, we opened up uh of a wealth management and accounting business, again, still with no money and greater in debt because of the student loans. We we uh financed everything with credit cards, quite frankly. We took cash advances on credit cards, not something I'd advise other people, but I did it. And uh we we did the math on it, though. We had a written business plan that if we could pick up one or two clients a month for two years, we would be okay. And we figured if we can't get one or two clients a month for two years, we didn't deserve to be in business anyway. And it was a it was a it was a slow roll. Um, but after about five years, you know, we were making really good money and we had a really good business. And having a supportive spouse meant everything. Um, I think a lot of times athletes may feel an entitlement. You've done a certain amount of time in sports, and when you transition into business, I'm gonna start at the top and not do the groundwork. And I took the opposite approach. I'm gonna go back to zero, start over, and really try to build myself up, take a lot of time with the feeling that if I was meeting a client, I I was gonna get their business because I just deserved it for all the hard work I did with the education and credentials I got, if that makes sense.

SPEAKER_01 16:08

It does, it does make sense. What I'm curious about is the creation of a plan in the first place. Now I know you're backed with a degree, but you've just come from receiving a letter, which I know is is was is more normal back then. It's kind of what I remember receiving, things like that. But you received this letter to say you are no longer required. How'd you go from receiving that letter? I'm assuming you felt a bit crushed, but to go from that to then, okay, darling, let's write a plan.

SPEAKER_00 16:39

Well, it was almost out of anger. It was uh there's hurt and then and then there's anger, and and we were like, we always knew this day would come, could come. So it's in the back of your mind. Any athlete knows they're gonna retire or get released some someday. So you know that it may come, and and I go, let's sit down and and attack this. The heck, screw these people. We're gonna show them that they made a mistake and we're gonna make something of our life. Like, let's let's go get them, if you will. The coach that yells at his team and says, we'll show you, coach, we'll we'll we'll go out and win the game in spite of you yelling at us, if you will. So it was it was like that, and and it really was just, you know, let's get, let's get, we realized we I needed a lot more education to be at the top of my field. And and that was as an accountant. The the wealth management business, which is what we ended up making our money in. I didn't even know it was a business, okay, when we started this plan. It was just to throw as much education out there, become as qualified as possible in whatever, okay, and let's see where the chips go go with that. So that that's what we did. Let's get educated, um, let's get smart, and um and let's see if that will that will lead to something, and it did.

SPEAKER_01 17:54

And and what I do like about the plan, I'm not sure if you were aware of it at the time, but you talk about one it it was like this five-year journey, but it was broken down quite simply with one or two clients per month for you and and knowing that if you did that you would you would achieve success. But along that journey, I mean, how how was that? Was it boom, two, two, two, and off we go?

SPEAKER_00 18:21

Well, at the beginning, when we started, again, everything was in writing with math. Okay, so we did the math and what our goals would be, and we went through different scenarios. And that's what I would advise almost anybody to do with any aspect, especially if you're worried about your finances, put it in writing and see where things are and how positive and negative scenarios could go. Once we started picking up clients, uh, the first goal after that within our business was to create raving fans, provide our clients with overwhelming levels of service so that these raving fans, if you will, could spread the word and bring us in a lot more business. And that ended up working out well. Like I consider myself a nerdy accountant, if you will, not a great salesman, even though I became a great salesman. I became a great salesman because all these clients out there were bringing me all the business that I needed. So it was A, get the clients, and then B, more importantly, much more importantly, keep those clients through overwhelming service and then spread out these tentacles, if you will, to uh to grow the business. And it ended up being a lot of fun. We we had a great career. I I was partner, I had a partner for 10 years, and then we split just because we didn't need each other. It was very amicable, but in the beginning it was important because we shared expenses and things along those lines. And then he was able to do his own thing, and so was I, because we had a couple different visions on where to take the business. Um, but we had a lot of fun and um we helped a lot of people along the way. So I can't think of a better business where you're helping people and making a lot of money. So it was it was a really good run, you know.

SPEAKER_01 20:03

Yeah, and and when you when you um it sounds like a great run. And I know you've you've given us the sweetener there uh towards the end where you've you know recently sold and and moved on. But I'm interested a bit in that journey that you found a partner. Was was your partner a sports um with Aim to sports as well? Was there that sort of affinity?

SPEAKER_00 20:23

Yes. My partner, uh, his name is Brendan Pearson, was a Division I athlete, played college basketball for Fordham University, um, was an all-state basketball player in in high school. So, yeah, having having another athlete, I think, I think is a big deal in terms of learning discipline. Again, we talked about adversity, um, teamwork, all those leadership skills, all those things were were important. And uh when we split up, he ended up having a very successful career as well. His business did very, very well. So uh I think having a sports background is is really important. Um, it's something I look for when I hired people. Um one of the guys that took over my business was uh was a college athlete, and um, and I think he learned a lot of lessons from smok from sports. The other guy, even though he wasn't a sportsman, was very smart and very and very disciplined. You know, it takes it they have two different personalities, but uh they're both very successful in their own right, too.

SPEAKER_01 21:28

And how do you think, you know, something that you look for in someone that you would hire as you know as as you've grown that business? How do well I suppose the question is, yeah, how how do you harness that? How do you harness that athletic edge into something that can work inside your business?

SPEAKER_00 21:46

Well, I think once you own the business, you become more of a coach than an athlete. So I think it's important when you own your business to know what kind of a player you have. Do I have a fast player, a slow player, smart player? Dumb player. Who fits into my business and how do I utilize that within the concept of a team? Okay. Where does every player fit in? And that's where I think it's more important when you're the owner to be a good coach than be a good player, if you will. Okay. You you graduate from player to coach when you when you start your business. And you're looking for pieces to fit in, okay, that that that complement each other. And the reason why I like sports people is just, again, the concept of teamwork. That that they know they're part of a team, that if a player on your team is too selfish, the whole team is going to fail. I mean, you know that. So so that's that that was important to me. Somebody that can handle criticism, that's not too sensitive, um, a thicker skin, I think that helps.

SPEAKER_01 22:51

I definitely agree. I think it does. It's especially on the criticism piece and that thicker skin. Um, you know, you you talk about you know having to go through that adversity, but also that desire to be better, the desire to excel, which is in uh is it's either innate or at least it's learned through most most athletes as they go through their careers.

SPEAKER_00 23:14

I always asked my employees where we could get better, and I want to have an open enough relationship with the people that work in our office where they could come in and and criticize our business in a in a in a positive way. Same with our clients, seeking feedback. Um, I coached sports when I was done officiating. I coached baseball and I would coach kids, and I would seek feedback from the kids. What do we need to do to make the team better? What do I need to do to be a better coach? Asking their parents if if it was appropriate, uh knowing what parent to deal with, where we could, where we could get better, but always asking for feedback. And as you're because you're trying to get to this place of perfection that you're never going to get to, but you keep striving to get there and you end up having an excellent business for yourself. Um, in my business, my employees came first. They became, uh they were more important to me than the clients. I realized if my employees were taken care of, the clients would be taken care of. Um, I learned that in baseball, how not to treat people, because they don't treat employees very well in in sports. So um at the top levels, they do obviously with all the money they make. But um I learned how not to treat people, and I vowed I would not do that when I had a business. And I had employees that stayed with me for 20 to 30 years. So uh I guess they were happy.

Hiring Lessons And Crisis Growth

SPEAKER_01 24:34

There are too many stories of bankruptcies, mental health issues, and unfortunately suicide. And so I think it's time to act. Every year we see thousands of athletes that reach a point where they need to consider their life activity sport. It might be up timing, injury, or they need to juggle your careers between sport and a job. As a former English professional footballer, I have somehow managed to transition from sport into banking, strategy, innovation, and now life coach, career practitioner, and founder of the Second Wind Academy. So I want to help those around me find their career second with. Find me on Insta or through my new Facebook group, Second Wind Academy, where I'd love to know your thoughts and suggestions. You know, it'd like to think they were. Now, during that time, you know, what's great about having you on the show is you can talk through the phases of now growing your business. And I'm interested to understand, was it, hey, boom, straight up and it stayed up? Because being in Fin Services, you must have gone through some difficult times.

SPEAKER_00 25:38

Absolutely. At the beginning, if the first move, the first employee is the hardest because you're starting your business by yourself, and then, hey, this is working out pretty cool. And then you realize there's not enough of you to go around. And that first employee you hire is a big deal because your pay goes down to hire that new person, and you really hope it works out. So mistake number one was hiring the lowest cost employee and not having the right people and having to fire them, which is not easy, and then hiring better people at more money, and then it took a couple of years, but the business started to really succeed. And then the third, fourth, and fifth employees were much easier to hire. Uh, that that was no problem. Then I was at a point where I thought the business had peaked. Um, I became one of the top 15 advisors in our firm around the time of the terrorist attack in 2001. And I figured this was as good as it was going to get. And then when the 2008 financial crisis took place, um, my business actually grew by 400% after that. It went to a whole nother level. Uh, we went from being a small business to a medium to large size business, and um we be that's when we became a multimillion dollar firm. I realized the strategies I was putting into place to prepare people for worst-case scenarios really worked. And when the 2008 financial crisis, not only did all our clients stay, they really brought in many more people. And they're like, this guy knows what he's doing here, and um the business went to another, became the number one advisor in our firm. Again, that's using math uh for over a decade. And um, the prosperity was unimaginable. I I feel like the luckiest guy in the world when all that took place. It was really pretty cool.

SPEAKER_01 27:28

So that I mean, and that isn't you know, congratulations for that. But what were you doing during this downturn, during this financial crisis for you to to win business, not go out of business?

SPEAKER_00 27:42

They were actually very simple uh philosophies. Um, and that was as far as uh uh f people's finances were concerned, I made sure that anybody in retirement had no debt. They had no mortgage. I made sure people paid off their all their debt when it was time to do so. I never said to a client, take on debt, give me the money, because I'll make more money than whatever your interest payments are. During my 35 years in business, those words never passed my lips. That's not common in our industry where a lot of people want debt to be leveraged. It's okay in the beginning when you're starting a business. Once you start winning, then you, in my opinion, you pay it off so you're prepared for adverse consequences. And then from uh a retiree standpoint, I tried to make sure that everybody had more interest and dividends coming in than whatever their lifestyle was, so that they can weather a downturn. So when 2008 took place, our clients, their assets went down, but their income did not go down. And they were able to weather that storm, where a lot of other people were going into bankruptcy, there was all kinds of trouble. We we weathered the storm, and then we were able to go to another level. Our revenues went down, but none of like none of our clients left us during 2008. And we picked up a lot, a lot of business. And I learned to almost embrace downturns because that's when money leaves other advisors. And even though your business goes down a little bit, at the end of the day, it goes way back up. It goes way up. And um, that has worked very well, in my view.

SPEAKER_01 29:21

And it sounds like you had a strategy, or indeed, I'm gonna say a belief, that you stuck to throughout all of that. And that conviction, well, that conviction helped your helped your customers know what they wanted to do and or what you wanted to do and how you were going to help them.

SPEAKER_00 29:39

My my whole life was based on preparing for a worst case scenario. You think about it when I was in sport, what's the worst thing that can happen when you're in sports? That you get fired and you have to start a new career. Well, being prepared to do that and then having a career workout was very good. Preparing your finances for worst-case scenarios and having a positive attitude in life are not incompatible concepts. Okay, you can you can think you can have a positive outlook on life and think, well, what happens if the stock market goes down 30%? Am I prepared if that happened? And if I'm prepared if it goes up as well. And every situation is unique. But preparing yourself for worst-case scenarios is is a pretty good idea in in my view. And and we try to put that into practice to the extent that you can. To the extent that you can.

Debt Rules And Downside Protection

SPEAKER_01 30:28

Yeah. Again, I just think that's so interesting. Now, I I want to I want to go a little bit into the those clients that you serve. Now, I know there's a there's a whole plethora of clients, but I'm interested in those those umpires. And the reason why is because so many of those listening, watching this show are athletes who either themselves are retired or planning retirement. And I'm interested in just more sort of the mindset of the clients as they sort of come to you as practicing umpires, retiring umpires, retired. You know, how how how does that shift? And what sort of things do you look for?

SPEAKER_00 31:11

Most people, you know, what I've learned in business as when somebody comes to me for financial advice, they have one question. Am I going to make it? Am I going to be okay? Okay. Take my finances and make me okay. Most people aren't looking to get rich. If they're already rich, they want to stay rich. That's one thing. How do I stay rich? And preparing for worst-case scenarios is a pretty big freaking deal, in my view. If they're not yet rich, we're quantifying for them the piece, what they need to do to get from point A to point B in a very logical way. Okay, this is what you need to do so that you can achieve what I call financial independence, which is when the money from your investments is greater than what your lifestyle is. Once you've achieved that, you have, once you've done that, you have financial independence. And we're just coming up with strategies to make sure that that stays as is. We're not trying to take rich people and make them triple their money. Okay. If I say that to somebody, I would say, is it worth taking on risk so that you become, you have more money than you know what to do with when you're already in that situation right now. You know, as an athlete, you never want to turn a win into a loss. Okay. If if in in baseball, if you're winning by three runs for baseball fans out there, if it's the ninth inning and and a team has a runner on third base, you're not playing the infield in, you're you're playing the infield back because you're willing to give up a run for the out so that you can win the game. Okay. Um in football, if you're winning by 20 points in the fourth quarter and you have the ball, you're going to run the ball and use the clock rather than try to run up the score. Yet in finances, all of a sudden, because of people's inherent greed, they feel they need to get richer, richer, richer. Okay, and and they need to protect the downside. So just being able to answer the question with math, am I going to make it? Am I going to be okay? If you can do that for a client in my business, you're you're winning. Okay. And clients feel very comfortable knowing that they have strategies in place that they're going to be okay. That's it.

SPEAKER_01 33:24

And so when you look then at the an athlete compared to your um uh average individual, yes. Do you see them as having those same needs or do you recognize there's a I mean there's a difference in timing?

SPEAKER_00 33:39

It resonates with athletes because when I can make that point to an athlete, I can almost see their body language switch when when I get into their headspace and say, and and I'll pick whatever sport they're in, by the way, to draw that analogy when I'm when I'm dealing with. Works very well with athletes and they play ball. You could just see them get focused and go, yes, sir, I am I'm gonna do what you say and and uh because because you're recommended to me, and they fall in right in right in line. With the non-athletes, if they're fans, they can get it. But the but the non-athletes, I have to get them get them on board. If if you're a good advisor, which I think I am, you have to be able to take different personality types, different, you know, there's people in the world. You have the athlete, you have the widow, you have the kid that inherited money that needs to get slapped around every now and then so that they know how not to get themselves in trouble. Oftentimes, what I have challenges with is have somebody that's been very successful in business, and then they retire, and then they want to do something else. And they've had people kissing their butt for so long that when they go into a new field, I have to remind them that, you know, you're you're you don't want to put too much of your money at risk here and and lose what you've already had. And and I think because I'm an umpire, I can be assertive yet respectful with them and let them know just because you're successful in one thing doesn't mean you're gonna be successful in something else. So let's make sure we don't blow the whole thing. There's a Major League Baseball player, Kurt Schilling, who was a pitcher, had a$50 million net worth and lost the whole thing in about 18 months, okay, by leveraging a business. And I thought he was a pretty smart, smart player. He didn't, he could go into business, but he didn't need to lose$50 million. That's insane, you know. And uh that's what I'm cautioning people against.

Post-Sport Career Planning Playbook

SPEAKER_01 35:31

And you you know, you mentioned earlier on that this need for having or having a plan, I often call it a catastrophe plan. So but having that financial view to say, okay, how do I, you know, as you said, sort of protect that downside. Um when you then sit with someone, as those listening, um watching this show are thinking, all right, that works, that resonates. What what's the next best thing for them to do to plan for that career after athletic performance?

SPEAKER_00 36:05

I think well, it depends. The first thing I would do for preparing for a post-athletic career is see what do you want. Okay, put it in writing. And I would also ask people, a lot of people are afraid to ask. If somebody wanted to go into my field, I probably have somebody once a month, a college student or some somebody, reaches out to me and says, Hey, if I want to be doing what you did someday, help me connect the dots. And I'll I'll give you two examples in in my own life where people achieve success, and that were two or two of my children right now. My daughter, okay, was thinking about uh going into government, and and I advised her to get as many internships as possible, okay? Meet with as many people doing um what you may want to be doing. Now she's the United States Department of Energy representative at the U.S. Embassy in Beijing, China. My middle child said he wanted to be a pilot, okay? He was always playing those stupid video games on the computer with aviation. And we brought in pilots to sit with him and show him if you want to be a pilot, this is what you need to do. And they showed him what being a pilot was all about. And he became a captain with Alaska Airlines by the time he was 32 years of age. So it depends what you want. You know, it doesn't have to be financial success. You could be a nurse, a teacher, whatever it is. But I would ask people in the field that you think about going into, have lunch, you know, go out for a drink with them, pick their brain and then see if that's what you really want to be doing, shadow them, then come up with a written plan and then execute that plan. Okay. And don't think that you need to do it in six months. It might take a few years. And our generation today isn't is very anti-delayed gratification. But if you if you put this work in and you're smart about the work, you can be disproportionately rewarded, in my view.

SPEAKER_01 37:58

And that's great. So just making sure I'm I'm getting that down. But you know, you say talking to people is something definitely, I think I know a lot of athletes, a lot of individuals, certainly young individuals, struggle with that idea of reaching out to others. But you're talking, really advocating that reach out, have a have those conversations, um, do the, like you say, do the internships, these mini trials in some respects. Do you enjoy it? Don't you enjoy it? Get out, have a coffee, a tea, or something with individuals who can perhaps show you that day in the life or what it means to be in those types of roles.

SPEAKER_00 38:33

100%. That that people people need to do that to find there's a lot of people that think they want to do something, and then after they spend a day seeing it, they're like, boy, I'm sorry, I'm sorry I went into this field.

SPEAKER_01 38:45

So true.

SPEAKER_00 38:45

You know, all they would have had to you know and I found a lot of people, you know, I'm I'm in this country club circuit now where I'm dealing with a lot of success, I meet a lot of successful people, and every last one of them is willing to share what they learn. Uh people are really, you know, everybody has a favorite subject, and that's themselves. And and they're willing to share their knowledge. Um, if somebody came to me, I'm more than happy to sit with somebody and say, no, no, no, don't if you're doing that, I wouldn't do that if I were you, I would do this. And you could save people years and uh of time that would that they would have waste pursuing something that would have never worked out. So uh so I would take advantage of that.

SPEAKER_01 39:24

Yeah. And then and one of the bits that you've emphasized a lot through this, and that's taken from your own lesson, is writing it down, seeing it on paper. Um and I and uh listen, I'm a believer that writing it, drawing it, coloring it in is perhaps even more impactful than typing it up on a computer. But you really talk about this write it down. Why do you think that's so important?

SPEAKER_00 39:46

Well, I I think it's important. I remember when when I was into my business and you talked about weathering market downturns. And I had I had my business, I had the sales projected for the next couple of years, all my expenses, and then the bottom line profit. And just like you were saying, Ryan, what happens if the stock market goes down 30% and your income's tied into that? And 15% of the clients fire you because they blame you. What does that look like? And rather than thinking, what does that look like? I put it down in writing. Okay. I cut my sales down. I, I cut, I cut um some clients out and I looked, and when I looked at the bottom line, I'm like, that's not so bad. We could survive that. I'm okay with that. And rather than sitting worrying about it all the time, I I knew the math on it. And I'm like, if that h I hope it doesn't happen because I'd like to be making more money, but I know I can weather that storm. I I know I can handle that. And so people that want to do a remodel on their house, um, that they want a second home, whatever it is, if you put do the math on things, and then when you look at it, go, oh my God, no, I don't, I don't want to do that. Or then you do the math and go, yeah, I think that can work. Um, let's go for it. Because as an accountant, people came to me, again, because I combine accounting and wealth management, people would come to me with business ideas, um, all kinds of things. And I'm the type that likes to say yes. It's very easy to say no, don't do something. I try to find a way to yes. And I would sit with my clients and go over how the math would work. And then they'd look at me and go, nah, I don't think I want to do that. I I did all these three or four things that you're bringing up, I didn't realize that was part of the game. So I think I'm gonna pass on that. And this is the decision becomes self-evident, if you will, by putting putting it in writing.

SPEAKER_01 41:32

Yes, yeah, I think yeah, I I I agree with you as well. I I I like that visual nature and writing it down, and because the important bit that you say at the end there is then executing on a plan. And there's something that certainly in that athletic mind, it's that goal orientation. You've got a plan, it's written down. Let me go ahead and now execute on it, find out and you know, make it real.

SPEAKER_00 41:54

If you think about it in sports, a a good coach that that talks about winning all the time and doesn't do anything about it is not a good coach. Most people that are successful have some sort of a process that works. And that that's what you're looking for at the end of the day, a repeatable process that works for the most part. And golf, golfers have a good pre-shot routine that they rely on under pressure. In your sport, there's things that you do that you rely on under pressure. When I um part, I had a process calling balls and strikes that that I relied on and was very successful under pressure. In business, I had processes for everything that evolve, okay. Um, but but that so if I was meeting with a new client for the first time, there was a process on how to do meeting number one. There was a process on how to deliver plants, a process on client communication that you're always trying to improve on. But that's what winners do. They have processes that work.

Coaching Adults And Letting Go

SPEAKER_01 42:55

Yeah, absolutely. And listen, Jack, it's been so fascinating just hearing your perspective in building the business or coming from being an umpire, um, building a business. Uh there's w one last little bit that I'm I'm really just keen on, and that is as you became successful in your business, you know, you spoke about becoming a coach. And that was that's how you ran that business. Not being a you didn't say manager, you didn't say leader of sorts. So describe how you learned to be a coach in that regard or and what that meant.

SPEAKER_00 43:31

Yeah, it's a it's a great question. I I think one thing that helped me is when I was coaching children. I coached kids for a long time, and I realized that I very early on I could not assume anything. And that I had to teach, talk to adults in a similar way as children, but showing them respect, not being demeaning to them, show showing a lot of respect. So I learned how to coach kids, and that translated well into coaching adults. I think a lot. Of business owners make mistakes in that they don't allow their employees to grow and thrive. So in my business, if I think about the two people taking over for me, when I was in my early 50s, I realized, wow, I had this great business, but now how do I get out of it? Okay. I have Ojo Wealth Strategies, it's just Ojo, it's kind of a star-based systems. How do I get out of this freaking thing someday? And I ended up coaching people in my office to take over. And I had to let allow them to do meetings. I had to allow them to fail, okay, and make mistakes, realizing that in the long run we'd be better off. Now they're they're stars in in their own right, and now they're coaching uh our employees, if you will, on how to get to the next level. Is that is allow people to do things. I mean, the most perfect example in all of American business is the McDonald's brothers, who thought they were the only ones capable of making the hamburgers until they they were told that your your business can be repeated. And they were like, who are we going to get to make these burgers? Teenagers? And they're like, Yeah, that's what you're gonna do. You're gonna get people to come in and make the hamburgers. And they became a Dow 30 company. So uh realizing, you know, letting go of work is as the business prospers, letting go of a lot of things, hiring people smarter than you, okay, it becomes a lot of fun because you you realize you don't have to do a lot of the work and you can have a lot of the free time that you seek out.

SPEAKER_01 45:30

So how did you know it was time to exit the business, to sell the business?

SPEAKER_00 45:35

I realized I was watching the progression of the people I had in my office. To be perfectly frank with you, I have the passion and desire right now, and I could still do it right now if I if I wanted to. But I saw the two guys I was mentoring really go to another level, and I saw them chomping at the bit. And I had made my finances, my finances were in really good shape. And I said to them when we got to 2024 and 2025, I said, I I you are now in a position to own the business, but I want you to do it for two years. Still gonna be under my in my name, but I want you to run it as though it's yours. You'll you have the power to hire and fire, make any decisions that you want as long as they're reasonable, and let's see how things go. And at the end of two years, if that goes well, then you're gonna take over the business under something that we mutually agreed to, which was a contingency sale where I get paid over a period of many years based on the success of the business. And um, and everything worked to perfection. Quite frankly, the reason why I wrote the book, Too Smart to Be an Umpire, in 2025 is I was so bored, I thought the clients are definitely gonna need me and need to talk to me. And nobody was calling me, they were calling them, and I had the time to write, write this book. So that, you know, that that'll tell you something. My last year in business, I had the time to write a book because the guys running the business were doing such a good job. And now, now that they own it outright, they're doing a really, really good job. And I'm very proud of uh Jason Gordon and Anthony Sandomers. I'm very proud of the job that they're doing right now for our clients.

SPEAKER_01 47:11

I love that. I think that's great, Jack. And you know, I I actually, you know, I'm working with a a few athletes who would probably love to just bend your ear and have a conversation with you as as they embark upon the sort of wealth management strategies as well.

SPEAKER_00 47:28

Sure. Um, yeah. Uh they can Ojo is a very uncommon name, O U J O. So there's OjoWealthstrategies.com and then uh too smart to be an umpire.com. There's a website for the book too. So I'm easy to find if somebody wants to get a hold of me.

SPEAKER_01 47:43

Absolutely great. I'm sure there are many people watching and listening who are going to be uh searching you and uh trying to reach out. Certainly if you're open to it, uh always have that virtual coffee because this is this has been a fantastic 45 or so minutes for me.

SPEAKER_00 47:58

Uh Ryan, I really enjoyed uh speaking to you, and and that that's a sweet spot for me. Athletes uh trans transitioning into the business world. And uh absolutely with with the things you learned in sports, you could people can do so well in the business world. They really can.

Where To Find Jack And Closing

SPEAKER_01 48:14

Yeah, couldn't agree more. Listen, Jack, I just want to say again, thanks so much for taking time out of your day, bringing your perspective, sharing your story. I've really appreciated your time. Thank you. Thank you, Ryan. Thank you for listening to the Second Win podcast. We hope you enjoyed hearing insights from today's athlete on transitioning out of competitive careers. If you're looking for career clarity for your next step, make sure you check out secondwin.io for more information or to book a consultation with me. I'd like to thank Claire from Betty Book Design, Nancy from Savvy Podcast Solutions, and Cerise from Copying Content by Lola for their help in putting this podcast together. That's all from me. Take it easy until next time.