Major League Dreams Failed, Financial Advisor Won Big

He was one step away from Major League Baseball. Not close in the way people casually say it—13 people accepted out of 350 who tried out for professional umpire school, moving quickly through the minor leagues, close enough to taste it. Then at 30 years old, with a pregnant wife and no money, a new league policy ended it overnight. He had no backup career, no savings, and no idea what came next. What he did in the following four years turned that devastation into one of the most successful financial advisory practices in the country.

Introduction:

Most people think success comes from talent, luck, or being in the right place at the right time. Jack Oujo's story proves it's built on something far less glamorous: discipline, delayed gratification, and doing the unspectacular work when nobody's watching. After his release from professional baseball, Jack didn't spiral—he and his wife wrote a resume that same night, and within two weeks he had four job offers. He chose Ernst & Young, and for four years worked full-time in accounting while going to school every single night, refusing to even watch a baseball game because it was too painful. By the end of it, he'd passed all four parts of the CPA exam in one sitting, earned his CFP certification, completed a master's degree in taxation, and picked up his securities and insurance licenses—all without knowing exactly where it would lead.

What happened next is a masterclass in building a business the right way. Jack started his wealth management firm with borrowed money on credit cards, no name recognition, and a simple written plan: one new client a month for two years. He hit it—and kept going, eventually becoming the number one advisor in his entire firm for ten consecutive years, all while building a company culture that put employees and clients first. When the 2008 financial crisis hit and the market dropped 40%, most advisors panicked. Jack's business grew 400% in the years that followed, because his clients had been planned for the worst case all along.

This conversation goes deep into what most business owners never talk about: building processes instead of chasing goals, treating employees like family instead of numbers, developing your own successor from a 15-year-old kid mowing lawns into the person who eventually buys your business, and knowing—years in advance—exactly how you're going to exit. Jack shares the exact math behind building a $12 million wealth management practice from zero, why "no shortcuts" isn't a cliché but a strategy, and why he believes success ultimately isn't measured by your bank account, but by whether your adult children still want to spend time with you.

Who is Jack Oujo:

Jack Oujo spent his early adult years chasing a career as a professional baseball umpire, working his way through the minor leagues after being one of only 13 people accepted into professional umpire school out of 350 applicants. At 30 years old, with three years in AAA and no call to the majors, a league policy change ended his baseball career, leaving him with a pregnant wife and no financial safety net. Rather than let the loss define him, Jack channeled his discipline into accounting and financial planning, working at Ernst & Young by day and studying every night for four years to earn his CPA, CFP, and a master's degree in taxation.

From there, Jack built his own wealth management and accounting practice from nothing, funded initially by credit card debt and a simple, math-based growth plan. Over more than two decades, he became the number one advisor in his firm for ten consecutive years running, built the business into a multimillion-dollar practice with 15 full-time employees, and mentored two young team members—starting when one was just 15 years old—into the owners who eventually took over the business he built. Jack recently sold and exited the company, now rebranded Oujo Wealth Strategies, and is the author of Too Smart to Be an Umpire, a book detailing the lessons from both careers.

5 KEY TAKEAWAYS:

1. A Career-Ending Loss Can Become the Foundation of Everything — Jack was released from professional baseball at 30 with a pregnant wife and no savings. Instead of spiraling, he and his wife rebuilt his resume that same night and had four job offers within two weeks. He spent the next four years working full-time and studying every night, refusing to watch baseball because it was too painful, while earning his CPA, CFP, and a master's degree. "I can either feel sorry for myself for the rest of my life or try and take on a new path."
   
   
   
2. Success Is Built on Process, Not Goals — Jack became the number one advisor in his firm for ten consecutive years without ever setting a revenue target in a staff meeting. Every meeting focused purely on process—how initial client meetings ran, how follow-ups worked, how service was delivered. "If we do these things right, we will win the game, not let's win the game." When his team found out they were the top office in the country, they were shocked—because growth was never the conversation, only the work.
   
   
   
3. Plan for the Worst Case, and Downturns Become Growth Opportunities — When the 2008 financial crisis hit and the market dropped 40%, Jack's business didn't shrink—it grew 400% in the years that followed. His planning philosophy, borrowed directly from baseball, was to always prepare clients for worst-case scenarios in advance. "Bear markets are not fun, but your clients will appreciate the work you're doing, and you will get more business as a result of it down the road."
   
   
   
4. Mentor Your Successor Before You Need One — Jack began teaching one future business owner how to rebalance investment portfolios when the employee was just 16 years old. Two decades later, that same person—along with another he trained in their twenties—bought the business Jack built. He retained 98% of his clients after the sale because they had already built trust with the team taking over. "You can develop your team. I did it with a 16-year-old kid."
   
   
   
5. Redefine Success Around Family, Not Just Financial Milestones — After selling his business, Jack described feeling gratitude and relief rather than emptiness, in part because he built a life where work never fully eclipsed his family. He and his wife recently spent seven weeks in Southeast Asia, something he says would have been impossible during his working years. "Success to me is when your adult children want to spend time with you and be with you. I believe family comes first."
   
   
   

Connect With Jack Oujo: 📍 Business: Oujo Wealth Strategies 📚 Book: Too Smart to Be an Umpire — available on Amazon and at toosmartotheanumpire.com

Partner Offers: Manage Your Money Like a Pro Manage your finances like a pro while chasing your entrepreneurial dreams! Many successful entrepreneurs use Wise for seamless international transactions. With low fees and real exchange rates, Wise helps you keep more of your hard-earned money. Ready to level up? Check out my Wise link 👉 https://wise.prf.hn/l/QLyNwLz and start saving today!

Music Credit: XMPLA https://youtu.be/p9re3wWvCLo?si=zni260AfeO5rOZvS

#JackOujo #TooSmartToBeAnUmpire #FromBaseballToWealth #FinancialAdvisor #WealthManagement #NoShortcuts #ProcessOverGoals #BusinessMentorship #2008FinancialCrisis #FinancialIndependence #EntrepreneurMindset #FamilyFirst #DelayedGratification #SuccessStory #LindaVo #InspiredBySuccess

Transcript

SPEAKER_01 0:00

Early 30s, wife, kid on the way, no money, no plan. That moment could have broken him. Instead, it built him. He went on to become one of the top financial advisors in the country.

SPEAKER_00 0:10

I looked up at the ceiling and my I can either feel sorry for myself for the rest of my life or try and take on a new path. He'd never mentioned that in a meeting. Never once. When people in the office found out we were the number one firm, they couldn't believe it. They're like, we have the best office in the country. I go, yeah, we have the number one office in the United States of America right now. And they're like, wow. Success to me is when your adult children want to spend time with you and be with you. I believe that. I believe family comes first. And um, you got to develop a great family first. I know a lot of rich people that have kids with all kinds of problems, and I know poor people that have have grown very successful children. In 2008, the stock market went down 40%. Our clients' portfolios went down, but their income did not because the business grew by 400% after 2008 because people realized our strategies work.

SPEAKER_01 1:01

As an entrepreneur with a global team, one of my biggest challenges was managing international payments. I was stuck with high fees, slow transfers, and endless complications. Whether it was paying my team in the Philippines or buying products from Japan, I tried multiple banks and services like PayPal, but nothing seemed to work. Then I found WISE. The savings have been huge, and transfers that used to take days now happen in hours. It's fast, simple, and has become a vital part of my business strategy. If you're not using WISE for international payments, you're missing out on a game changer. Click on the link in the description to get started with WISE Today. What do you do when the one thing you built your identity around doesn't work out? Not because you didn't try, not because you weren't good enough, it just ends. And now you're stuck asking, who am I without it? Today's guest was one step away from the major leagues and then got cut. Early 30s, wife, kid on the way, no money, no plan. That moment could have broken him. Instead, it built him. He went on to become one of the top financial advisors in the country, not from luck, but from discipline, long-term thinking, and doing the work when no one was watching. This episode is really about identity and what happens when the thing you built your life around disappears. I'm Linda Vaux, and this is inspired by success. Let's welcome to the show, Jack Ujo.

SPEAKER_00 2:21

Thank you, Linda. I'm excited to talk to you today.

SPEAKER_01 2:23

Tell me about your journey and you know, because it's a fascinating journey, and a lot of people I've heard a similar similar podcast host. He it's it's called The Wealthy Way, and he had a similar story where he built his whole life around you know his baseball career and everything, and then what like it just got taken away, you know, and so they had to build around that. And even another podcast, uh a host called Lewis Howes, he built his whole identity around sports and uh and and then next thing you know, he had an injury and they got taken away too. And you know, he went into depression for a while and it was just sleeping on his sister's couch, but eventually he got himself out of it. But tell me your journey, your story, how it all happened, and how you came to where you are today.

SPEAKER_00 3:04

Sure. So um when I graduated from high school, I was a good, very good high school baseball player, but my parents had no money to send me to college. So I took up officiating and I officiated basketball and baseball, encouraged by my next door neighbor growing up, a guy named Ed Sanicky, who played for the Philadelphia Phillies. He suggested I tried umpiring. I thought he was nuts, but he said uh you were a catcher, you'd be you'd be good at it. And through my four years of college, I graduated from Seton Hall University. I found myself working some of the best amateur baseball games. High school state championships, they were sneaking me on college games, and I had this accounting degree, and I thought, you know, I'm gonna try out for professional baseball. They probably won't take me, but I don't want to be looking back on my life someday and say, I wish I would have tried something. So I went to professional umpire school, and uh they only took 13 people out of 350 that tried out, and I was one of those 13 people that they accepted, and then I started going through the minor leagues in baseball, and I was moving very quickly through the minor leagues, but at the same time, I did realize that the funnel to the major leagues gets narrower and narrow narrower and narrower, and I did work in the off-seasons as an accountant in New York City in case baseball didn't work out. And by the by the time I was age 30, uh, they put in a policy that if you had three years in AAA and the major leagues didn't take you, you you got released, and I was released. And I had a pregnant wife and no money, and uh had to start over again, and I was devastated because I was moving so quickly through the so quickly that you could taste it. I I got about as close as you can get without without getting there. So I so I was devastated, and uh I remember the day my release came. I looked up at the ceiling in my bedroom. I write about it in my book, Too Smart to Be an Umpire. I looked at the ceiling and said, I can either feel sorry for myself for the rest of my life or try and take on a new path. And you mentioned depression coming out. I would not allow myself, I was self-aware of how hurtful this was. So I remember I read a book by the former Chrysler chairman, Leah Coca, when I was in baseball, and he said, in order to be successful in business, you need to get as much education as you can and then do something with it. So I decided to work as hard as I could in business. I got hired, fortunately, by E.Y. Ernston Young, and I worked on tax returns for famous and wealthy people. And uh I decided to go to school every night for as long as I could, and within a four-year period, and I didn't know where this was leading either, by the way. I got my I passed the CPA exam, all four parts in one sitting. I took the certified financial planner exam, I got a master's degree in taxation. I also got securities licenses and insurance licenses, not knowing where it would lead. Um, you know, there were hiccups. I I found accounting would be very boring. When you're in when you're in professional baseball and there's 30,000 people at the ballpark and there's organ music playing, I found myself counting hats one day to verify a client's inventory. And I thought there's got to be a better way. And then I ultimately went into the wealth management business. I started a wealth management business and combined that with accounting, and the business just went nuts. It went, it went crazy. But all with borrowed money, um, I borrowed on credit cards to start the business because I had no money. And the thing I did, and I would encourage people to do, is I had a written plan with math. And I came to the conclusion if I could pick up one new client a month for about two years, the credit card debt would be paid off and I'd be off to the races. And I thought, if I can't get one new client a month for two years, I don't deserve to be in business. And so when you do things with math, you put pencil to paper or spreadsheet or use AI, however you want to do it. I think it takes away worry and it also makes a lot of decisions self-evident in terms of risk reward. You you have a better idea of what you're doing. Too many people do things by the seat of their plant pants, and so I plan things out, if you will.

SPEAKER_01 7:05

Well, I want to take it back too, because some people still do get stuck after that identity. It takes some time and to get out of it, but you know, you you were able to turn that that around. I mean, when how were we you were able to support yourself for that long to study after losing, you know, that major leagues almost getting to the major leagues? So how did you hey survive financially as well? But to be able to study that to get out of that mindset.

SPEAKER_00 7:30

The weekend I got released. I got released on a Friday afternoon around Thanksgiving. And um, my wife and I put our resume together that night. We we we did it that night, and we identified some 50 firms that we thought would be a good place for me to start working for. And I sent letters to those 50 firms, and within two weeks I had four job offers, one being from Ernston Young, which is the one I accepted. So I worked nine to five. I went to school at night and studied at night and studied on the weekends, getting all these letters next to my name. And I did that for four years. I did not allow myself to watch a baseball game. It was too hurtful, too painful. And because I was self-aware, I'm depressed by this, okay? And I'm also aware I need to move on because nobody's gonna feel sorry for me down the road. So I'm I'm self-aware of the depression I'm going through. But as I was going through these four years, I found every time I took a class or I passed an exam, I was getting tremendous satisfaction. And I knew, I just knew I was leading towards something special. I also was aware that between the age of 30 and 34, the years are going to pass by anyway. If I worked nine to five and come home and scratch out a living, you know, things would have been okay. They would certainly not be at the level they're at now. But things would be okay, and the four years would go by and I'd have a nice, boring life, if you will. But I I wanted more out of life, and that that's why I decided to try to go. I was willing to bet on myself. The fact that I almost got to the major leagues, I had some confidence. I think I have some talent at something. So uh I'm gonna bet on myself again, and hopefully there'll be a better result um in the next career. And that's what happened.

SPEAKER_01 9:16

I'm guessing that's great. Like I'm guessing you so also believed in yourself, and you also had your partner to who believed in you too, right? Is that is that what helped you?

SPEAKER_00 9:24

I I remember gr growing up, my dad always wanted to be self-employed. He worked for other people and was miserable in his career. My mother kept telling him, You're no businessman, people are gonna take advantage of you. And I remember when I said to my wife, I want to go into business, we're gonna have to go in debt, borrow. And my wife said, Yeah, whatever it takes. Whatever it takes. And um, so having somebody, having a we're married 40 years this year. So having somebody, having somebody with you that's willing to go grind it out through the tough times is is a big deal. It's it's probably the the most important. Besides having a good attitude, having a supportive partner means a heck of a lot. You gotta have that. You gotta have that support.

SPEAKER_01 10:04

Wow, that's really, really inspiring because um you've built something credible. And um, I'm curious to know what it looked like when you built your built from nothing, because you know, some people s build something and it goes average and they hit a ceiling, but obviously you went beyond that level and you wanted to build higher and you had bigger dreams. So take us back to what it looked like from the beginning and what what are the main challenges you had? You you had to borrow, you said you borrowed and got into debt, and and you just you set aside one new client per month. I mean, did you hit that? Was that setting the start uh standard too low? What was that?

SPEAKER_00 10:41

So what happened was in the beginning, again, I'm working as an employee for somebody else in accounting, and then I started picking up side clients. I started making money working at my job and with side clients. And then I decided I'm I'm basically conservative by nature, even though I'm self self-employed. So I decided to seek out a business partner, and I found somebody else that was in a similar situation, and we came to the conclusion if we pool our resources together to buy tax software, have an office, have an employee, that would be lower cost, and we could hopefully sail into the sunset together, if you will. And the two of us put this business plan together, and then we were we we were partners for about 10 years, and then we ultimately split and went our separate ways because we didn't need each other anymore, if you will. And that's when my business really went to a higher level. And it was all done, it was all process driven. I never I was the number one advisor in my firm, uh, and this is by math as well, for over 10 consecutive years. I never set out to do that. We had a process that worked. Anytime I met with our staff, all we talked about was process. We never said our goal is to make X amount of money, our goal is to increase sales by 20%. I think that's all a bunch of nonsense that people do. We had very few staff meetings unless they were process oriented. We all we did was work on our process, and by having a good process, the wins take care of themselves. If you if you talk to people in sports, Nick Saban, University of Alabama football coach for years, kept saying process, process, process. And um, and so I developed processes for our business for initial client meetings, for what happens when a client comes into the office for a follow-up meeting, how does service work on an ongoing basis, data storage, employee manuals, every there was a process for everything that that evolved. And I also, when I started having employees, a lesson I learned from business was how not to treat people, which the way baseball treats lower-paid employees is disgraceful, that they have to live with host families, they live in poverty. So my employees came first, 100% paid medical insurance. They made the policies on vacation time, paid time off policies. Employees came first, and I had people that worked with me 25, 30 years before they retired. So they were hired at the beginning and they stayed with me for a really long period of time. I did consider them family.

SPEAKER_02 13:14

Wow.

SPEAKER_00 13:15

And uh, and so, and I didn't want yes people around me. I wanted smarter people around me, and um, I checked my ego at the door. I also had the attitude that from our business that I was going to compete on service. And I I consider myself a nerd. So I wanted to have clients become advocates for our practice. My attitude was I had a job where I was on call 24 hours a day, seven days a week. Client emailed me on Saturday, the emails returned on time. Not Monday morning, I'll get to it. Uh I I created service models that where I said to our employees, if our client isn't talking about us the way you would talk about your favorite restaurant. If I asked you, what's your favorite restaurant in Sydney? You'd probably have something that would come to mind and you'd start raving about it. You go, that's the way people have to talk about us. That is our standard around here. And it also made it fun because we enjoyed working with clients. There were very few people when I looked at the caller ID. I was like, oh my God, I have to talk to this person. You know, we were able to grow the business and get rid of bad clients. We graded them A through F. Any client that had a C minus or below, we got rid of because we had more business than we knew what to do with. Um it just it just multiplied. And there was a point I remember in 2007, I thought my business had peaked. I became one of the top 15 advisors in the firm, and I was like, this is as good as it's gonna get. And then after the 2008 financial crisis, the business went went to another level. It grew by 400% after the financial crisis because the way we do our planning is based on worst-case scenarios. I I learned in baseball to plan around worst-case scenarios, we have a positive attitude, but plan for bad things. And when the financial crisis took place, our clients were protected, and the business went to a whole nother level that I never expected. So none of none of the success was planned for. Like we planned daily for successes, but it just grew and multiplied all organically, never paying for a client. Probably one of my biggest regrets in business is I because I didn't know it would be this successful, I think we could have done even more if I acquired uh a couple firms and had them model what we did, but I didn't do that. Things worked out fine anyway. And I and I don't regret it like, oh boy, my life is terrible because of it. It just probably if we did it in the acquisit if an acquisition or several acquisitions, I think it would have been at an even higher level, possibly.

SPEAKER_01 15:44

Well, that's fascinating. I love hearing about the processes and the fact that uh different um point of views about running the business and how you grew it as well. And you mentioned improving the processes and you didn't have the stats growing that like it's just interesting because most companies do I want 15% growth in the next, you know, and they have numbers to it too.

SPEAKER_00 16:04

But the fact never mentioned that in a meeting. Never once. When people in our office found out we were the number one firm, they couldn't believe it. They're like, We have the best office in the country. I go, Yeah, we we have the number one office in the United States of America right now. And they're like, wow, and because we never talked about it. Never, it never, you know. I I remember from sports, a winning coach does not does not necessarily talk about the importance of winning the game. They're talking about the things necessary to win to that that happen as a result, if you will. If we do these things right, we will win the game. Not let's win the game. You know, coach there's a lot more to coaching than saying, come on, let's go all the time. Uh yeah, you have to work on specific things.

SPEAKER_01 16:46

So, as a leader, what advice would you give to somebody who wants to do the same as what you did and improve their processes? Do you think they need to look into, you know, the the things that are bottlenecking? Like how would you do, you know, what advice would you give for somebody to create the same process like you did to improve their business?

SPEAKER_00 17:04

There's several things you could do. One, talk to your employees, okay? Because if a business consultant came in, the first thing they're going to do is interview all your employees and they'll say, I'll tell you what's really wrong with this place, and they'll go through an avalanche. And a lot of people are not engaged with the with the people that work right under their own noses. I would do that. I'd also ask for for customer or client feedback. In my case, I sought advice from my clients, and when I got their advice, I changed some of the ways that we did business around right around the advice that they gave us. And it turned out to be wonderful. I remember one of my clients saying, I'm getting all this stuff in the mail. Can't I just get everything on one sheet of paper? And we developed a quarterly spreadsheet to give our clients information that's they specifically needed. And years later, they'd go, that's all I look at. I all I look at is this one sheet of paper you gave me. I don't have time in my busy life to look at all the rest of this. That came from clients. People that work in our office provided great uh feedback. It's all right under people's noses. They just need to look and not and shut up and listen to what people around them have to say. I would do that. The other thing is this written plan of math is grow your business. One of the reasons why I sought out a partner is when I was doing tax returns on the side, I realized I'm working 40, 50 hours a week, I'm doing these other tax returns, we're getting a 70, 80 hour, there's not enough of me to go around. Okay, and and the big decision people have to make is that first employee that they hire because it involves a reduction in pay, and and they're hoping to get their business. That's when I retired, we had 15 full-time employees. The first one was the hardest one, okay, because I'm making good money now, and all of a sudden I have to pay an employee X amount of dollars a year, that's right out of my pocket. That's the biggest risk in the world. But a business owner has to learn to let go of things. Hire people that will complement what you're doing and keep on going, okay, as your business grows, it steps back to go forward, back to go forward, back to go forward. And you have to be willing to do that. You have to let go a lot of the work. You have to let employees fail, never hurting your clients, but allow them to do meetings and let go, letting go a lot of the work and allowing human beings can thrive. And again, just being like a coach, you have to know your players. Good coach knows what kind of players they have. Do I have somebody fast, slow? What am I dealing with here? And try to use the players that you have to try to create a thriving business.

SPEAKER_01 19:39

I love that. And you, you know, you apply the principles in what you did with the sports into the business world and talk about coaching. And I'm curious to know about leadership skills as well, because what what are those transferable skills that you saw with your coach in order to be a good leader? You know, how do we and you mentioned different, you know, employees and seeing what skills you can take, but how do we lead overall a good team? And you mentioned basically delegating to our team and stepping back, but is there a point where you, you know, if you step back too much as well, and you're not putting enough focus and energy into the business, or is it more of a thinking high level? Tell me a little bit. There's a couple of questions there, but the leadership skills is crucial.

SPEAKER_00 20:20

I learned that you can't assume anything, and you have to you have to be humble when you're teaching. Some people are good teachers and other people are not. And anytime an employee of mine made a mistake, I considered it my fault because I didn't instruct them properly. Okay, and I did it with hum with humility, not ever because a lot of account a lot of people don't like accountants because they talk down to people, okay? And or instead of teaching people, they're trying to show people how smart they are. Don't show tell me how smart you are. Help me learn something, okay? And that's what you have to do with your employees. One of the people I I mentioned that I sold a business to two of our employees recently. One of those employees came to me as a 15-year-old, somebody that I coached in baseball, and said, If I want to see you in your office, I want you to tell me what I need to be doing to be sitting in your shoes someday. And when this person was 16 years old, I was teaching them how to rebalance investment portfolios. A 16-year-old.

SPEAKER_02 21:14

Wow.

SPEAKER_00 21:14

Okay, and and that person developed into uh CPA, CFP, connected all the dots I gave them, along with another younger person that was in their early 20s. Okay, now they're in their mid-30s. Okay, now it's 20 years later, they're in their mid-30s, they're gonna own the business. They started by by putting up Christmas lights in the office. So so you can develop your team. You you can. I've I've had other advisors say to me, you know, where do you get help? Where do you get people? I I did it with a 16 year old or 15, 16 year old kid, okay, that that that developed into one of the owners of the business. So there's there's a lot of smart and good people out there that want to get ahead, and you have to empower them and teach them. You know, humble, invest the time. Uh, there's a great book out that I'd encourage people in business called the Email. By Michael Gerber on why most small businesses fail. And I think that that's a very good reference. Besides my book, I think it's a very good reference point in how to do things.

SPEAKER_01 22:11

What do you look for when you're like what you just mentioned that you hired young like when they were young and they're keen to learn, I'm guessing, and they're smart. What are you what are the skills that you're actually looking for when you're hiring back then, especially for them to stay that long with you?

SPEAKER_00 22:24

No matter what the position was, I wanted attitude first. I wanted somebody to come with a good attitude that was willing to learn and be part of a team and play a role, people that I can leave alone. When I ran my business, I never watched a clock. And I told them I'm not watching the clock. If you come, if if we're here from 8 30 to 4 30, if you come in at nine, I'm not going to say anything. And if you need to leave to watch your kids' game at 3 o'clock or cheerleading practice, go. I just want you to make sure that the phone call from the client was returned during business hours, even if you have to do it during the game. So I was looking to hire adults, number one. Number two, I was looking to fill in spots. What kind of a player do we need? What are we missing here? And try to bring in that person. I always try to develop our staff to fill in roles so I can I can grow them into promotions, but sometimes you need a social media person, you need a CFA, you need a tax accountant. So it depended on what players we needed, but they had to get along with the rest of the crew. Because the more you grow, you can have toxic personalities come into the office. And that was not good with me. I wanted people to be humble. I was humble around them. I always said, the people that work in my office, tell me what to do. I don't pay you. The clients, I'm just the conduit, the clients pay me. You keep the clients happy, and I'll be happy with you. You don't keep the clients happy, then we might have a problem unless the client's being unreasonable, in which case I will get rid of the client. And like I said, we we've done a bunch of that over the years that we're clients, we're not cultural fits. Most of them are wonderful, but you'll always get a couple bad apples.

SPEAKER_01 24:06

Did you go through any really because you know when you mentioned that 2008 crash, you skyrocketed, but did you go through any tough challenges with the business?

SPEAKER_00 24:16

But I learned to embrace them, and I'm going to tell you why. In 2008, the stock market went down 40%. Our clients' portfolios went down, but their income did not, because we were producing income for them, for their investments, for the people that were retired anyway. I believe in my business, financial advice, money moves during down markets. When the market's going well, everybody's happy, nobody's going anywhere. When down markets take place, that's when you can measure an advisor. How well did whatever they promised you hold up, if you will. And that's when anytime there was a bear market, I lived through 2000, 2002, the stock market was down 40% over that. 2008, it went down quickly, then started recovering quickly, but they were 40% drop. Advisors say percent. Clients say I had a million, now I have 600,000. Uh, but uh the business grew from that very quickly. I mean, we recovered our revenues, I would say, inside of 18 months, and and we were off to the races. And like I said, the business grew by 400% after 2008 because people realize our strategies work. And uh so I've told the the guys taking over for me, bear markets are not fun, but your clients that we have will appreciate the work that you're doing, and you will get more business as a result of it down the road. It'll again steps back to go forward, back to go forward. That's what people have to do.

SPEAKER_01 25:39

I love that. Now, I I love to hear about wealth management and success as well, because you've worked with a lot of money and business owners and executives. When it comes to building wealth, what what are people doing and that's what are they doing wrong?

SPEAKER_00 25:53

Sure. Uh they're making it much too complicated and they're looking for immediate gratification. I explain to people, as far as the stock market is concerned, theoretically, theoretically, the stock market should go up every business day of the week. If there was a Linda corporation, for example, and I was role-playing with you as a client, I'd say, today you came to work, you made some money, you paid down your debt, and when today and put some money away, maybe when today ends, you should your net worth should be at an all-time high. Okay. It should be at an all-time high because you're doing this every business day. Now, maybe Linda booked a great guest, or maybe somebody's mad at Linda or whatever. So there's these fluctuations. But five or 10 or 15 years from now, the Linda company should be worth more. The people in our world today are looking at the computer screen going, come on, Linda, like have your stock go up, Linda. Come on, get a better guest on. And it's the same thing with the freaking stock market. I'm like, these are long-term investments, and people need to know that going in. We're looking to buy companies at reasonable prices, and and and it depends on so they need to understand that financial markets are long-term, number one, and to be patient. Number two, they need us uh they need a plan. They need to know if they need to be living off a certain amount of money someday, they need to build a lump sum of capital. What are you doing for the next 20 or 30 years in your life to hit those goals? So having a plan, even if it's at an early age, because it's going to change, sticking with that plan and moving forward. And uh, if you're not making enough money, you need to do the things necessary to make your skills better to be making more money. But but that that's where it starts. And then as people get financial success, they have to avoid being stupid, okay, being greedy. I use sports analogies. If you're if you're winning a sporting event, you want to do the things necessary to get the win, and you never want to turn a win into a loss. So a lot of people older like me have had a lot of success in the stock market. If you've done well, you can bring down the risk a little bit because you've already won the game. What are you trying to do? Okay. So different, it depends on the person, depends on the circumstances, but people should should know what their quantified financial objectives are, financial goals are, excuse me.

SPEAKER_01 28:09

Do you like still invest now? Are you still investing? And do you just invest in the stock markets or do you diversify? And you mentioned rebound balancing your portfolios as well as sure.

SPEAKER_00 28:18

Um with clients, what we do, first of all, when people are retired, we let try to make sure that they have no debt, no mortgage. We're very opposed to carrying debt while the stock market is going down. So that's strategy number one of protecting the downside is having no debt at retirement, unless you have some sort of a pension from the government or something like that. So having your mortgage, your house paid off by the time you retire is something that that we're big believers on, which is goes against the grain of what a lot of other people say because they're trying to cut their taxes, and it's just stupid, in my view. And anyway, having a portfolio where the interest and dividends coming from your investments are greater than what your lifestyle is. That's how I would define financial independence. So, for example, if somebody had $2 million and the portfolio was producing $80,000 a year in interest and dividends, and they needed $60,000 a year to live on, they've achieved financial independence, in my view. Okay, you're looking for this lump sum to produce the income needed for you to sustain yourself for the rest of your life, in its simplest terms. Okay, with clients, we we do cash flow projections from like 60 to death of how much money they'll need based on their lifestyle and how the income works in good and bad markets. So people later on in life should be focused on interest and dividends. People in their 20s, 30s, and 40s are in the accumulation phase. And again, it's not the thing I liked about our business more than anything else is that it wasn't one size fits all. Everybody's different. We all have different lives, different things going on. My goal was to make sure that clients had a understood where they needed to be and stay and how we were going to do it, and I would prove it to them using historically worse stock markets. I would say, like, for example, the stock market's gone down by over 20% six times since 1950. Okay. What would happen if the market, because if you were my advisor, I'd come to you and I go, let's suppose five or ten years from now the stock market hasn't moved based on this little plan that you just gave me, where am I at with my life? And we show that to people. And I and I think it gives people great comfort in that you've protected the downside. Quantifying your goals is the most important thing.

SPEAKER_01 30:36

Do you guys help when when you were doing that wealth creation? Was what about people that had businesses and entrepreneurs as well? What are your thoughts on that? And how do they protect their wealth and grow their wealth with investing with a business as well?

SPEAKER_00 30:51

Sure. With with businesses, people need to know what their exit strategy is. What is the object of the game here? When you're successful, how do you get out of it? How does it end? And what is your strategy for that? In my case, I was just trying to make money make a living. I never even thought about selling the business someday. And as it became very successful in my early 50s, I realized I have a star-based business and that people are just using me. And I really had to work on how do I get out of this thing where the business is sustained when it's just they're coming to Jack. And ultimately the business was rebranded as Ojo Well Strategies. There's other advisors, but they're kind of doing it the Jack way, if you will. That was what I did. I created the process. This is how we do things. This is the philosophy. And the people that have taken over who are now in their mid-30s have bought into that process. The clients have bought into them, okay? And 98% of the business has been retained after I've left. Okay. So, so you have to think a business owner has to know how am I getting out? Okay. And if you're expanding, why am I expanding? Like what am I, what am I looking to do here? And I always did that with business owners, again, using math. Okay, what are the upside and downside of any decision you're going to be making here? People need to go in with eyes open of how do things work. I want to expand my business. Why? Okay. I want to invest $200,000 in my business. Okay, let's look at that. And now we're going to go through your financial statement going forward. What are the new sales that result by putting the $200,000 in? What are the expenses that result? And now let's look at what the profit. Oh, the profit looks good. That looks really good. It's a lot better than where we're at right now. Okay, now it what if this doesn't work? And then people could say, that's not so bad. And then you can go, okay, let's go ahead with this decision. Okay, you have to always look at things and decide you're dealing with risk reward. Is it worth the risk? And that that's how I always looked at things with my business. I remember in my business I had 1,250 square foot of office space. And uh one of our employees said, we need more space. We need more space. And I was looking at buying uh an office condo for $300,000. And I said to myself, you know, before you buy another office for $300,000, why don't you get rid of some deadbeat clients that aren't really making money for this firm? I ended up getting rid of 20 or 30 clients. I go, before I spend $300,000 on a business, I'm gonna stop the time we're wasting on these clients that I don't think are gonna develop, and then I'll buy the building. Okay. So yeah, you have to you have to be looking at all aspects of your business. Do you have good customers, bad customers, who are the ones that we're developing? Where's this thing going? And uh because every business is different, you need a financial crystal ball that you have to create. And it's fun and and you make it fun. Is it is it worth going through this risk? Sometimes you might invest $100,000 on something, it doesn't work. And if you can sustain the loss, all right, we tried it, it didn't work, lesson learned. Or it did work, and this is where we're at now.

SPEAKER_01 33:55

Yeah, that's powerful because a lot of people don't actually look at the risks in like some people just go all out without thinking about the risk and factoring all the downsides that could happen. And I yeah, they just think about the optimistic side of the business part, not the yeah, unexpected things that can go wrong.

SPEAKER_00 34:12

The accounting side of my business, I always said to my clients, I go, it's it's just like a parent when when their kids ask if they can do something. It's always safe for a parent to say no to their kid. They can't get in any trouble by saying no all the time. As an accountant, it's always safe to say no, you can't do something. I always tried to find a reason why something could work. Okay, and I would explore that with the client. Let's see if we can make this work. And I would say, if you do this, this, and this, then this becomes a good decision. But if you can't pull these things off, then it's not gonna work. And often the client will say, I don't think I can pull that off. And they'll go, All right, we agreed that we'll table this for another day or something along those lines. You have to what you want to be positive and look for reasons to make them work, but you can come to the conclusion that maybe it doesn't. And and I know in my business I've made some really good no calls in terms of things I did not get involved with. And uh and and I was happy, and I was happy for those decisions.

SPEAKER_01 35:06

Yeah, because I've heard a saying like the when you get wealthy, incredibly wealthy, it's more of a matter of saying no to things which will help you keep going.

SPEAKER_00 35:15

And especially when I'm you know, when I'm dealing with regular clients, you know, I'd say our goal here is to get to say three million dollars for you to be financially independent. And when they're at a million eight, I'd say, you know, this is going to be boring now for the next 10 years. Because now that you have this money in your pocket, people are gonna come to you with stupid, nutty ideas that you have to learn to say no to. And you just need to keep your job or keep your business. This point to that point is not that difficult if we connect these dots, and the clients would be like, all right, I get I get it. And then when it got to that point, for me it became very gratifying. Like I would have never done this without your guidance, things along those guidelines. That's where I got my satisfaction from from people hitting their goals and keeping their goals.

SPEAKER_01 35:57

Wow. Now that you've sold the company, what does it feel like? I mean, do you because as entrepreneurs, we like to build and make an impact and solving problems and all the fixing and finding solutions, but uh what does it feel like now that you've sold your company? Are you still feel feeling fulfilled? What do you do with your time? Because I heard a lot of people get bored with after they sell.

SPEAKER_00 36:20

I feel tremendous amount of gratitude. I feel tremendous amount of gratitude that it was taken over by people that that I mentored, if you will. I feel gratitude that the clients say when they're talking to the guys that took over my business, that they sound just like you. I feel like I'm talking to you even though I'm talking to them, which I find funny. So so there's gratitude. There's there's uh a relief that that the responsibility is no longer on my shoulders. My wife and I just I went to Southeast Asia for seven weeks. I would have never done that uh when when I had the business, especially during during our bit our busy season. So um I'm also having three grandchildren within a 10-month period of time. I have three children, all three of them are having kids this year. So um I'm going to take my time, but whatever it is I do, I I wanted to be giving back. I I hit my own financial independence numbers. God has blessed me. So I I'd like to help other advisors probably help their clients. Whatever it is, I I want to just give something back because I feel I feel a tremendous amount of gratitude. I really do.

SPEAKER_01 37:23

Wow, that's beautiful. Is there anything like any books or mentors that have really guided you on your journey? Or, you know, is there a ritual that you do spiritually? Like what's helped you?

SPEAKER_00 37:34

Well, I'm a Christian. I'm my Lord and Savior Jesus Christ, I thank every day. So uh I am a person of deep faith, and uh I'm grateful for that. So so the Holy Bible would be book number one. But there's been several, I read a lot, and there's been several people that have influenced me, both in sports. Bobby Knight, who is who referees are not a big fan fan of, wrote it, wrote a book called The Power of Negative Thinking about how games are lost, not won, and how businesses can fail instead of going to another uh another level. So the worst case scenario, something I learned in baseball, that was a very good book by Bobby Knight, The Power of Negative Thinking. John Wooden, the former basketball coach at UCLA, wrote about the processes. One of the most successful college basketball coaches in history uh was teaching his players how to tie their shoelaces. He broke that down into minutiae. Every little process, every little thing had to be done. I I learned that from reading about coach John Wooden. Rick Wood. What's that book? What was that book? I remember the name of the book, but John Wooden has been deceased for about 20 years. Any, any maybe uh something the wizard of something might might be in there. That was his nickname. Also, Rick Petino, the college basketball coach now at St. John's, his book was about deserving success. Do the things necessary to have your own equipment. That's why I put all those letters next to my name. If I'm competing against another advisor, I know I've done the work equal to or more so than than somebody else to have a basic competency level. The the Emith by Michael Gerber, I mentioned, and my book, Too Smart to Be an Umpire, I'd mentioned too, because I think people will learn a lot from that, an awful lot from that. A lot of life lessons that I've learned. That's that's why I wrote the book. I put I put it all in there.

SPEAKER_01 39:21

And if you could do anything different in business, if you could go back in time and do anything different or could change something, what would that be?

SPEAKER_00 39:29

Acquisitions. It would be I I I might have acquired an another firm or two. Everything worked out so well, I wouldn't want to have to do it over again because I'd be afraid that I would have messed it up. Everything, I feel like the Far is gump of financial advisors, because I've had so much good luck has come down on me again. Be I think because of these client referrals that I've gotten. Some very you know smart and wealthy people have come to me because they were highly referred by by our existing clients. So so I think that's it, that's important too.

SPEAKER_01 39:58

What are your thoughts on um the future looking ahead? What excites you? You know, is there anything that uh you we you know excites you about AI and how we could use that in wealth creation? What are your thoughts on that?

SPEAKER_00 40:10

In my business, AI, I think uh clients can do their own tax returns and set up their own investment portfolios. They can, but I think I think the best financial advisors, as I've tried to get this point through, are great coaches. And I I don't think there's an AI coach yet to help people with the emotional part of money, which which is something very much involved in. In our business, we're using AI for um for meeting notes, if you will. We ask clients to record the meeting, and then the notes are printed and follow-ups are are are put all over the place. I think AI is is a tremendous tool. I think it's gonna create, I'm not trying to be political here, I think it's gonna create more income inequality because lesser type of employees are not gonna be needed. I was a baseball umpire. You know, now you can tell a ball or strike on your phone why do you need to pay somebody $400,000 a year for? So a lot of jobs are gonna be taken away. And I think it's important to really analyze is my job the type of job that that's not gonna exist someday. And um, you know, you doing podcasts, you need a human being to do those things. Nobody wants to hear a machine interview somebody. So so you have to you have to figure it out. I think it's all evolving. I know Vladimir Putin was asked, what is what is your greatest fear? And he said artificial intelligence when he was interviewed on TV recently. So you can embrace it, which I've always tried to do. Um I'm not in the business anymore, but the two guys taking over from me both know they want that that I advise them in the strongest possible terms to be ahead of technology, be at the forefront, be the one that people want to model off of. And people need to really embrace it. They really need to really embrace it and get up to speed on it.

SPEAKER_01 41:49

I love it. What's one key piece of advice you want to leave to the audience, whether that be about money, success, what what's something that really resonates with you or that we haven't spoken about?

SPEAKER_00 42:00

In the world we live in right now, no shortcuts. No shortcuts is is don't be afraid to take the time to do the things necessary to get competency levels, to start your business. You don't have to rush things. Take your time, believe in delayed gratification, because ultimately things come to you. They didn't, you know, I went from being broke to a multimillionaire within 10 years. Some people might say 10 years is too long to wait. I don't have 10 years. If I tried to do it in two years or four years, still be I'd still be working because I had to, not not, you know, because I I would have had to keep working. So no shortcuts would be the big thing. I'd also advise people to ask other people that are doing what they're doing if you could have a cup of coffee with them or lunch and find out about what they did, just like you're doing right now with me. Find out what mistakes did you make? What can I avoid doing? Are you glad you you you entered into this? What would you do if you had to do it over again? Things along those lines. A lot of people don't don't do that. I know my children, uh, my children as an example. I advised my daughter to get internships when she was in college rather than rather than working at the movie theater. Nothing against that, but I thought she'd get more out of it. Now she's the uh Department of Energy's attache at the U.S. Embassy in Beijing, China, representing the United States in negotiations. My my son Christopher had an interest in aviation. We invited a pilot to come over to the house and give career advice. This is what I would do if you want to become a pilot quickly. He became a captain at Alaska Airlines when he was only 32 years old, a captain. You don't have 32-year-old captains usually. So doing that, and it doesn't matter what you want to do, but taking advice from other people and seeing what they did so you can connect the dots a lot quicker.

SPEAKER_01 43:47

Geez, it sounds like you've got something, you know, you you've done a great job with your leadership and your business and also your family as well. Because yeah, that's it's it's really inspiring because you're You've you've uh guided your kids to become great as well and to become successful. And I'm just curious about generational wealth. Are you did you build that before you retired? Did you ensure that you built enough generational wealth to be able to live comfortably yourself, but also look after the ones that your your loved ones and your grandkids as well?

SPEAKER_00 44:19

That that's interesting because I wouldn't I wouldn't have known what that was like. And I've told my kids I I don't know what it's like to have rich parents. So with my children, I told them your mom and I will always help you. They know all our numbers too. They know every everything's been explained to them. Okay, it's all out there. It's a family as far as we're concerned. And I go, I would do nothing to help you if you're a lazy bum. I go, I will do whatever I can to help you help yourself. You know the situation, and and we're open to each other. It's confidential to the rest of the world. But uh, if you're bums, I'm not gonna give you a freaking thing. And I want them to be able to create their own path, but they know there's a soft spot beneath them, which they have that benefit. If they're laid off from their job, they're still gonna be okay. And and I think it helps them be happier, quite frankly, knowing that that's that soft spot is there behind them. But that's kind of the way I've I've phrased it. That you know, if you need help, we're here to help you. If if you're putting an addition on your house, like whatever it is, and and the grandchildren's colleges will be provided for that. They get a being being a Jack and Eileen grandchild um scholarship, so to speak. So that that's taken care of. See, that's selfish too, because I want more grandchildren. I don't want to have kids, so I gotta have more grandchildren.

SPEAKER_01 45:34

Yeah, time goes white. The kids grow so fast, yeah. So how would you personally define success? What does it mean to you? Because everyone has their own definition of success. But what is successful?

SPEAKER_00 45:43

Success to me is when your adult children want to spend time with you in Vivaya. I I believe that. I believe family comes first, and um, you got to develop a great family first. That's beautiful. I do because I think that's ultimately your report card. If you have, if you don't have kids, that that's no problem. But if you do have children, how they turn out is a is a major reflection on on yourself, if you will, good, good or bad. I I know a lot of rich people that have kids with all kinds of problems, and I know poor people that have have grown very successful children. But I do believe when you have money, it's an advantage. I I do. There's no there's no question about it. There's all kinds of benefits to it. I believe because I was a baseball umpire, you have to remember, when I was in baseball, I was one of the top hundred people in what I did for a living for a living and made hardly any money. So I couldn't judge financial success on that. You know what I mean? This career had financial success, but you could be an emergency room nurse, school teacher, and be very successful, even though it may not make you a millionaire, if you will, or something along those lines. I don't I don't judge people that way. I think, you know, family comes first in my opinion. Or God comes first.

SPEAKER_01 46:53

That's beautiful. But yeah, because you know, some kids uh grew up having it all, but you know, the parents work hard or they spend so much time and energy into their business that they sacrifice their time with their family and you know, a good family life as well. So for me personally, I think it's having that balance where you can build something, build a legacy, but also be there for your kids and help them and guide them grow too. Because yeah, it's sad hearing about people that have wealth and that their kids are miserable, for example.

SPEAKER_00 47:23

Well, that that's what I said before with the people that worked in our office. I think that's one of the reasons why they stayed with me for so long, is I said, you can drop everything you're doing and go attend to something with the family, sporting event, an emergency, but the phone call needs to be returned. We need to do both. This isn't not I just care that the work is done. I don't care when it gets freaking done. I care that it's done, and I care that you're attending to your family too, just as I have to. And I remember my children understood why daddy was returning a phone call on Saturday morning from the sideline at their kids at the soccer game or something, because that was gonna help, that was explained to them. But on the same token, the Thursday afternoon game at 345, Daddy could also be at that game too and not miss it. So, you know, and and I tried to for foster that culture within our business, you know, for our employees that you know, I've value that you're valuing family. That that that's not a they're not inconsistent as far as I'm concerned.

SPEAKER_01 48:19

Jack, this has been a great conversation. I found some valuable, interesting uh tips, and I hope you guys listening found some great key takeaways that could help you with your business. If you haven't already, please do me a favor and hit that like and subscribe if you're watching on YouTube and hit that follow button if you're listening on podcasts. Jack, where can people find you and connect with you?

SPEAKER_00 48:36

Sure. There's our website, Ojo Wealth Strategies for the Business, and then a shameless promotion for my book, Too Smart to Be an Umpire, Too SmartTeanumpire.com. You can find it on Amazon or books uh wherever books are sold. Those those are the two ways to get a hold of us.

SPEAKER_01 48:52

Awesome. Thank you so much for your time, Jack. It's been a pleasure.

SPEAKER_00 48:54

It's been my pleasure, Linda. Thank you.

SPEAKER_01 48:56

Thank you.