From College Dropout to Business Coach with Tom Cuthbert

No one is surprised when someone goes to college, graduates and becomes successful in life.

This gives the misleading impression that your circumstances determine your success.

But today’s guest, Tom Cuthbert, is living proof to the contrary.

From a college dropout to a Vistage Master Chair and CEO Coach, he knows what it takes to have a successful business career.

In today’s episode, you’ll discover the easiest way to teach children about money, why real-life experience is superior to any degree, and what to do when you doubt yourself.

Listen now.

Show highlights include:

  • How every child can learn to handle money responsibly (so they succeed as adults) ([7:57])
  • Why your “Life-BA” is more important than getting a college degree ([10:56])
  • What to do whenever you have doubts about your success in the future ([14:28])
  • Why the most successful CEOs work with business coaches to help them make better decisions ([18:42])


DLP063 - From College Dropout to Business Coach with Tom Cuthbert


Do you want a wealthy retirement without worrying about money? Welcome to “Retire in Texas”, where you will discover how to enjoy your faith, your family, and your freedom in the State of Texas—and, now, here’s your host, financial advisor, author, and all-around good Texan, Darryl Lyons.

Darryl: Hey, this is Darryl Lyons, CEO and co-founder of PAX Financial Group. Thanks for tuning in today. You’re listening to Retire in Texas, and as always, I have to give you our legal disclosure that this information is general in nature only. It’s not intended to provide specific tax or legal advice. Visit PAXFinancialGroup.com for more information.

And I always want to remind you when you text “TEXAS” to the number 74868, we have nine financial advisors, one of them will reach out when you send that text. They’ll give you a 15-minute consultation. They have a heart of a teacher, and so if you have any questions, that’s one way to engage with us. But just visit our website for all those disclosures and you’ll be good. [01:06].6]

Okay, so excited about the show today. Tom Cuthbert, I appreciate it. How do you say that in French?

Tom: “Cuth-bear” <phonetic> in French.

Darryl: “Cuth-bear.”

Tom: The French are always very fancy, but just Cuthbert in English.

Darryl: Yeah, thanks for being here. So, what’s cool about Tom is I know about Tom and you’re work with Vistage in coaching, so I want to get a little bit into that later.

Tom: Sure.

Darryl: I know people that know you and respect you, but I don’t know your story, so we’re going to get into that a little bit today. Is that cool?

Tom: Cool, absolutely.

Darryl: And I was telling Tom beforehand that it’s always my preference, for those that have been listening for a while, for me not to know a lot of the story, because the audience has given me feedback that they can kind of hear my sincere curiosity of learning about somebody, and so that’s the way I prefer to do it, and it’s not rooted in anything that’s lazy or anything insincere. I just really want to know people and, frankly, I always am amazed at people’s unique life stories. Right? Everyone has this unique life story, so one of our values as a company is respect, and we’re very much a faith-based culture, but we put that respect in there because we want to respect everyone’s unique life stories. [02:14].8]

Tom: That’s great.

Darryl: I look forward to learning more about you, Tom. Tom, where are you from originally?

Tom: Richardson, Texas, which used to be, when I grew up, a little tiny suburb of Dallas. Now it’s its own big city.

Darryl: Yeah.

Tom: And I think it’s more a suburb of Plano today than it is anything else.

Darryl: So, you grew up there?

Tom: Yeah, I grew up there. My mom and dad lived in Iowa for a short time before that. Dad was an engineer in the tech space, way, way back in the ’60s.

Darryl: Yeah.

Tom: About four months before I was born, they moved to Dallas, and fortunately, I was born in Texas and get to claim that.

Darryl: Did you grow up a Cowboys fan?

Tom: I grew up a massive Cowboys fan to the point that my mom used to work part-time at a preschool and she taught Roger Staubach’s kids. [03:01].5]

Darryl: Yeah, wow.

Tom: And Staubach, way before your time, Darryl –

Darryl: I get it.

Tom: – but I’ll tell you what, the guy was in icon and he was just one of the nicest people, and I had the chance to meet him as a kid and it’s just one of those life moments.

Darryl: Wow.

Tom: I shook the hand of Roger Staubach, so major Cowboy fan for life.

Darryl: A lot of people don’t know this, I actually collect sports cards.

Tom: Oh, wow.

Darryl: And so, having a Roger Staubach rookie is one of my favorites.

Tom: Oh, that’s a big one.

Darryl: And I always think about the story of where I get cards, but Roger Staubach, the other thing I like about Roger Staubach is he’s a really good business guy, too.

Tom: He is brilliant.

Darryl: I was up at LBJ, getting some ice or something at the convenience store and out comes Roger Staubach, and I was so kind of taken aback that I didn’t even know what to say. It was a Roger Staubach, but that’s pretty cool. So, was your dad, he was in the tech business?

Tom: Yeah, Dad worked for Collins Radio back in the day. It’s now Colin Aerospace and was absorbed by Rockwell.

Darryl: Yeah.

Tom: But it’s actually an important part of my life that people ask about a lot is the work I do today, as you alluded to, and maybe we’ll get to that. It’s really built around the one word “curiosity” and I’m very curious about people, very curious about things, very curious about life. That came from my dad. [04:10].4]

My dad, as I was a kid growing up, I would see him every morning, get up at the same time, eat the same breakfast, leave at the same time, home at the same time, watch the same news channel. I mean, everything was the same. White shirt, black tie.

Darryl: No kidding.

Tom: A nerd before nerd was even a word, right? He was on the beginning of that movement. And so it wasn’t until July 20, 1969, when I realized just how cool my dad was and how curiosity would be something that stuck with me for my life, and it was that day, as you may know, when they landed Apollo 11 on the moon.

Darryl: Yes.

Tom: And the work my dad did at Collins was in what’s called broadband impedance matching. Don’t ask me what that means.

Darryl: Yeah, okay. [04:59].2]

Tom: But the practical application of that is when they sent Apollo 8 to the moon, for the first time, a quarter million miles away, Apollo 8 was going to go behind the body of the moon and then have to reconnect the signal back to Earth, and I learned later there was a relatively high chance that that was not going to work.

Dad and a whole team of people did that, and on the day they landed Apollo 11 on the moon, he was at NASA as a team, where they have to be there during those landings. And the technology worked flawlessly and I was just like everybody else on the planet, blown away by that, and that and my dad really set me on a course of curiosity, so I owe a lot of that to him.

Darryl: That’s a cool story. I’ve had some rocket scientists as clients and had a chance to hang out with some of them, and their minds are just wired differently, the engineering. But it’s nearly an altruistic thing, because you work your tail off and, I mean, you can work for years and years and years and years and never receive any glory and accolades, and then something like this and you just breathe and go, “It’s all worth it.” [06:07].1]

Tom: Yeah, it was amazing and I realized just the significance of the work that he did, and then from that point through his life, he continued to do that. He passed away a few years ago at 91, had a great life, a very accomplished Navy pilot, flew blimps on and off aircraft carrier stuff.

Darryl: Oh my gosh, yeah.

Tom: I mean, just a great guy, a great dad, and wonderful influence for me, but that one word, “curiosity”, is what I think I would attribute the most to him.

Darryl: What did your mom do?

Tom: Mom, she kind of was a teacher, was a stay-at-home mom, and Mom grew up, and my dad liked to tell the story this way—my mom didn’t like it. You’ll get it when I share it—but Dad would compare himself to Einstein and so he would say, “Einstein would always make these comments that people would come to him and they would say, ‘Dr. Einstein, what if you married Marilyn Monroe? Your children would be both beautiful and have your intellect,’ and he said, ‘Ah, but what if the opposite were true?’” And Dad always laughed at that and thought it was funny. My mom was Marilyn Monroe. She was glamorous, beautiful, charming, wonderful, just a very kind person. [07:08].0]

You know what’s interesting, too, because I said I learned the curiosity and really gained that attribute from my dad. From my mom, I really learned to care about people and be curious about human beings, and not as much the technology aspect of it, but the relationship part.

Darryl: Yeah, that’s great. Now, did you have siblings?

Tom: I have one sister who’s older than me and grew up a hippie. I grew up, I was born in 1959, and so she’s seven years older than me, six or seven, and so I got to see her grow up through the hippie years and remember when she was a young teenager announcing to my dad that she was going to go in a VW van to New York to go to Woodstock. I think she was 14.

Darryl: Oh, wow.

Tom: And it’s just one of those other … at the start of my life. Let’s just leave it at that didn’t go well. But, yeah, she’s great.

Darryl: That’s middle class, would you say, your family income profile?

Tom: Yeah, absolutely, I would say we were very middle class. Dad and Mom were always conscious of what we had and didn’t have. But as a kid, I always had everything I needed and life was good, and I was taught a lot about money early on, which has been a blessing. [08:17].0]

Darryl: What did they teach you about money? Was there anything in particular that you remember?

Tom: Yeah, two things really jump out at me in particular. One was I had an allowance and we had friends that maybe had a little more or a little less than us, but the allowance was always earned. It was never just “Here’s a buck,” or 10 bucks or whatever and there were always tasks associated with it.

My dad, being a person of routine, would make sure that the boxes were checked and I would do this, and so the first stage of life that I learned about money was being a young person and going to work early. My first job was at Polar Bear Ashburn’s ice-cream parlor. I was Super-Duper Dipper and I actually got promoted, Darryl, you’ll be impressed with this. My first promotion was to a senior Super-Duper Dipper. [09:00].5]

Darryl: Oh, nice, yeah.

Tom: Yeah, it was a big move up for me. I was 16 and loved working at the ice-cream shop, but had to pay for a lot of my own stuff. And Mom and Dad were divorced when I was in my early-teens and so that creates some complexity and a little more independence for me. But those lessons of responsibility kind of part one as a young person was that, earn things. You work, you make money. That’s the connection.

Darryl: It’s funny you say that because I did some studies on this and trying to understand, is allowance better? Is commissions better?

Tom: Yeah.

Darryl: Our family is really of the same approach as yours, get the job done, that’s how you get paid, so there isn’t a monthly stipend that our kids get. But one of the key elements of all those studies was whatever approach you take, just having little conversations on a regular basis about money was really healthy.

Tom: Absolutely, and we would talk about that. That was a consistent thing for us.

Darryl: Yeah, that’s good.

Tom: The other part of life, and this may be interesting to you, too, that really made an impact for me financially was when I turned 18 and went off to college. Dad said, “Here’s some money. Here, so I’ll get you set up, and good luck.” [10:10].8]

Darryl: Is that right?

Tom: Yeah. And you know what? I look back, it was great because it taught me, and, man, if you have a list of dumb decisions financially, you can check the box for me for every single one of them, particularly early in life, right? And I think many of us are that way. But the lessons that taught me early, making those mistakes when the risk was smaller than it would be as you get a family and all those type things was really impactful to me.

Darryl: Can you share one of those dumb mistakes?

Tom: Oh my gosh, I don’t even know where to start. 

Darryl: I know, I have them, too.

Tom: The biggest dumb mistake was a red 1977 Triumph convertible. Still to this day, one of the best, most fun cars I’ve ever owned. Absolutely could not afford it. Fell in love with it and during college, and I ended up dropping out of college, partly because, as my dad would say, I ran out of money and grades at the same time. [11:02].4]

But never went back, wish I would’ve, but part of that was just adding financial burden on myself when I had that responsibility and then having to go work to make that money, and that takes time away from studies and so a big distraction. That was a very difficult time of life, but that investment I made, that spending on that car, was not smart.

Darryl: But you enjoyed the car.

Tom: I loved it. I would buy another one in a heartbeat.

Darryl: I know, it’s kind of one of those things. Yeah, I’ve got to get another one of those, got to go back.

Tom: Right.

Darryl: You did end up dropping out of college –

Tom: Yeah.

Darryl: – which is actually cool, because a lot of people that listen to the podcast, they tell me, “Yeah, that guy, yeah, they were successful because they went to college,” and, actually, a lot of the people enjoy the conversations of people who didn’t finish college.

Tom: Yeah.

Darryl: What did you do after dropping out of college? And where was it? Was it in Texas?

Tom: It was in Lubbock at Texas Tech.

Darryl: Texas Tech, okay, yeah.

Tom: Yeah.

Darryl: After that, what did you do?

Tom: Yeah, so I got a job and I got a job making the most money that I could find and it happened to be an assistant manager at a pizza restaurant, and two things happened at this time. [12:04].0]

One is I had planned to major in education and coach or do something like that, and I’ve always had a love for that. But I realized after literally a few weeks of working in their restaurant with a little bit of authority, learning how to be a manager, that it was a gift I had. I love people. I love to think about the numbers part of it and hitting our numbers for the day, and all those things that come with early stages that the restaurant business was a great proving ground for me. You learn all aspects of business in a microcosm of one location. So, I fell in love with leading and management, and that was a gift to me.

The second thing I learned was, if I was not going to get a college degree, I was at a huge disadvantage, and I knew that I needed to learn, and a friend of mine gave me a book almost as a joke I think, Everything I Learned at MBA School, and it was this collection of little stories from MBAs about what they learned. I’m like, Okay, I’m going to read this book. I’m going to have an MBA. Not exactly. [13:04].6]

Darryl: Sure, yeah. I know that book, by the way.

Tom: It’s a great little book.

Darryl: Yeah.

Tom: But that began a lifetime of reading. And the other thing somebody told me was to read the Wall Street Journal. Literally, for 40 years, I’ve read thousands of books. Literally, I read average 25 to 30 a year pretty easily.

Darryl: That’s amazing.

Tom: Yeah, and I’ve read the Wall Street Journal every day, and that learning has helped me get a life MBA, if you will.

Darryl: No, for sure. The Wall Street Journal, do you read the audio version or the mobile version?

Tom: I don’t.

Darryl: Read the paper.

Tom: I’m one of the guys that likes the paper, because I can read it at the gym when I’m doing something.

Darryl: I get it. You know what I used to do in college? I was such a nerd with the Wall Street Journal. If I didn’t have time, I don’t know why I did this, but if I didn’t have time to read it, I’d cut out the articles that I’d liked and saved them. But the Wall Street Journal, absolutely, it is an MBA, and then, of course, reading books. I think that that really is– I think a good lesson for anybody listening is that if you find yourself not in a good position for college for whatever the circumstances, there’s other ways to get edumacated. [14:04].8]

Tom: Absolutely right. Yeah, that’s a great point.

Darryl: What was the career like for you when you finally kind of found yourself?

Tom: Yeah, it was funny because I began to work my way up in the restaurant business and went from that location, got married, moved to Houston, got recognition. I was with Pizza Hut at this time and got a recognition as a regional manager of the year and thought, Oh, man, I’m really cool, and went on to another company called Pizza Inn. Just, really, a 13-year career, the last nine of it at Pizza Inn, and it ended up in bankruptcy. The company was in bankruptcy.

Darryl: I remember Pizza Inn.

Tom: Yes. Actually, it turned out to be a great experience. Another one of those life moments I remember clearly was when the company was in bankruptcy, I had an opportunity to leave and go to another company, and I called my dad and I said, “Hey, Dad, I got this opportunity. I’m going to do this,” da-da-da, and he said, “Well, if you stayed, which situation would you learn more from?” I went, “Gasp, man, that’s a really good question,” and the answer was staying and learning how to turn a company around out of bankruptcy. [15:09].2]

Darryl: Oh, yeah.

Tom: So, I was fortunate to get to work with a new CEO that came in, reported directly for him for a couple years, and really enjoyed learning from that. A lot of work, but we were able to pull. Tons of us pulled the company out of bankruptcy and back in the right direction. I went on to a couple other restaurant ventures and, eventually, woke up one day in 1999 after selling a restaurant group and thought, Yeah, this has been a fun ride, but capital intensive, highly competitive, low margins, why am I doing this?

Darryl: Yeah.

Tom: And then reflecting back on growing up with a dad in technology and realized that’s much cooler and probably a lot more profitable than the restaurant business.

Darryl: And so, then you got out?

Tom: I did. We’d sold out and I just decided it was one of those entrepreneurial sabbaticals, if you will –

Darryl: Sure.

Tom: – where I thought, What’s next? Found a great partner here in San Antonio that took a chance on me and we started a little company, and that kind of led to the next half of my working career that was in technology. [16:06].6]

Darryl: Yeah, there’s kind of three careers, right, or is there more than that?

Tom: Yeah, I would say there’s three. If you’re counting what I’m doing now, yeah.

Darryl: The restaurant. We’ll get into what you’re doing now, the restaurant. You didn’t retire. You pivoted –

Tom: Yep.

Darryl: – into technology. Now, give me some color on what that was more specifically.

Tom: Yeah, we started a small company here in San Antonio that, in 2000, tracked online advertising activity in website activity, and back in the day, that was early, and so we were working with companies like Yahoo and insurance providers and really learning about how the internet worked over a few years. In that, we found a specific problem in 2005 called click fraud as online advertising was growing, and so my partners and I pivoted and started a new company called Click Forensics that went on to be called Adometry that helped identify invalid click activity so advertisers –

Darryl: Oh? Okay, yeah. [17:01].5]

Tom: – get what they pay for. That company grew and raised and spent a bunch of venture capital, and it was a great ride as well, eventually acquired by Google. So, that gave me the moment in life where, back to the entrepreneurial sabbatical, what’s part three?

Darryl: All of this, you’re getting accolades in the restaurant business and you’re growing. Did you ever doubt yourself along the way?

Tom: Oh my gosh.

Darryl: Were there ever times where you were like, Gosh, can I even do this?

Tom: Yeah, every day, and I think there’s a balance between healthy and unhealthy fear in business. The healthy part of fear in business is you always have people shooting arrows at you, right? Competitors, yourself, your team. There’s lots of things, a lot of moving parts, as you well know, that can go wrong in a business, and so that fear was healthy. There also was the unhealthy fear that I had. I’m 5’6”. I was never– I wrestled as my sport because I was too small for the real sports –

Darryl: Football.

Tom: – as my mom would say, football or basketball. [18:01].1]

Darryl: Yeah.

Tom: And so, there’s some fear or some doubt in that. Being a college dropout is certainly another one of those. So, absolutely, I’ve dealt with that all the way through career.

Darryl: And you power through it.

Tom: Yeah, I think it’s just feeling that God’s gifted me in certain ways and recognizing those gifts. Also, one of the lenses that I look through to make decisions is, is this something that I can be excellent at or at least very good at?

Darryl: Yeah.

Tom: And I’ve learned really to say no to things that I can’t and lean into things where I feel like I can.

Darryl: Then you pivot going into the third chapter of your life, doubt it will be the final chapter.

Tom: Yeah.

Darryl: Is what?

Tom: Vistage contacted me, Vistage international organization, primarily CEOs that they work with, but they looked. At that time, they were looking for former CEOs to be Vistage chairs or CEO coaches, and I had not heard of them. A good friend of mine here in San Antonio was part of it in Austin, actually, before it was in San Antonio, and he would drive back and forth every month for his meetings and he would meet with his coach. [19:09].7]

He said two things. “One, it’s a great organization, and secondly, I think you’d be good at it.” That was all the encouragement I needed to look at, always appreciated my friend and his comment, and so I leaned in. I went to San Diego for a week and got locked in a room, if you will, with 26 former CEOs from all around the world, China, South America, and most were from the U.S. Every industry you can imagine, football helmet manufacturer to technology company, and just a great group of people, and I fell in love with the concept of helping others and that’s really how I think about the work I do today.

Darryl: So, you spent time coaching CEOs? 

Tom: Yeah, today the practice has grown. I have six groups, 120 members across those groups.

Darryl: Oh my goodness, yeah.

Tom: Two CEO groups are kind of the anchor groups where I spend the majority of the time, and so yeah, I added up. I spend over 1,000 hours a year in private, closed-door conversations with CEOs. [20:07].8]

Darryl: Yeah, that’s a life-changer because the impact that they have on a number of people. I mean, it’s significant. Gosh, there’s so much to ask you. I’ll have a couple more questions, but I’ve got to ask you, what are you seeing right now as maybe the biggest concern or challenge that CEOs are facing?

Darryl: There’s a couple things that jump to mind. The first obviously is the economy pending recession, inflation, interest rates, I mean, all of that is one huge headwind that we’re all facing together and we’ve certainly faced a lot of headwinds in the last few years with Covid and other things. That’s number one.

Number two is people, another very obvious one. The third may be not so obvious, but the people headwind is the way that people, their expectations seem to have changed some through Covid.

Darryl: Yeah.

Tom: Working remotely, maybe some sense of entitlement. And I am really big on it, it’s not a generational thing. I think every generation has great attributes and downfalls, and so it’s less that to me, and more just about maybe a mindset that people might have as we course-correct. [21:09].5]

Darryl: That’s fair. Yeah.

Tom: The third one, and this aligns with your question to me, is because of the ups and downs that we’ve had in the economy—a lot of opportunities, M&A, for example, coming up in the next year or so, a lot of headwinds and extremely difficult decisions to make during Covid—CEOs are doubting themselves more today than when I first became a CEO coach. At least, that’s my perspective.

Darryl: Wow, that’s amazing, and I could see that. I can absolutely see that. It’s like the rules of the textbooks are no longer valid –

Tom: Right.

Darryl: – in a lot of ways. If I could summarize, and there’s just still a lot to this, coming from a middle class family, becoming an ice cream guy, becoming a pizza guy, before that, dropping out of college, now you’re advising thousands or tens of thousands of people through CEOs and giving them life and hope and doing amazing, I’m sure, tactical things along the way, too, so it’s pretty amazing to see this, looking at it from that point of view. Then a couple more questions, and then I’ll close this out. What else? Outside of, and you can do coaching forever, right? [22:18].5]

Tom: Sure.

Darryl: As long as you got your marbles. But in terms of family or lifestyle, entertainment activities, is there anything that you enjoy doing?

Tom: Yeah, I’ll give you two things. One, somewhat important and business-related. The other the important one.

Darryl: Yeah.

Tom: The business-related one is, a few years ago, I bought a Sandler Training franchise here in San Antonio.

Darryl: Yeah.

Tom: My partner and a team of people have turned that around and it’s growing like crazy. We’ve built a company called Sales City Group that now owns multiple Sandler Training franchises around the country.

Darryl: Wow, yeah.

Tom: And we’re growing to 15 locations.

Darryl: Oh my goodness.

Tom: So, I’m kind of doing that as a … I guess it’s a business hobby. It’s an overstatement.

Darryl: I get it, though. Yeah.

Tom: I love it. I love the people that we have. I love our concept. They’re doing great work, and it’s just a way for me to have an outlet to grow something. [23:03].5]

Darryl: Yeah.

Tom: The big draw for me at this point of life is, number one, to guard my time, and so I do. I track exactly the number of hours I work per year. I’m very guarded when I’m off. Generally take Fridays off, for example, and just invest in taking that time and investing it back into family. I have three of the most awesome grandkids you would ever want to meet. They’re so much fun, six, four, and not even a year. She’s just about eight months. So, that’s really where I want to invest more time, and my wife, Jill, and I have between us five kids and a couple still heading off to college here in the next few years.

Darryl: Oh, wow, yeah.

Tom: So, we love spending time together, love spending time with family, love traveling when it makes sense for us. But that really is the focus for me for the last third of life, if you will.

Darryl: That’s very interesting. Very cool. The interesting part, I have to say, is it reminds me of Jocko Willink.

Tom: Yes.

Darryl: He says discipline equals freedom, and the idea that you’re disciplined with recording your time gives you that freedom to do the things that you want to do. [24:04].8]

Tom: A hundred percent.

Darryl: Yeah. Last question, most important question, what’s your favorite salsa?

Tom: Oh my gosh, I saw this on your list of potential questions and I thought about that. I’m not a picky eater or I’ll say I’m a picky eater. There’s certain things, I’m like, I’m not eating a black olive. There’s just no way I’m eating a black olive.

Darryl: Yeah.

Tom: But when it comes to stuff like salsa, I don’t know, I mean, I don’t even know a brand. I know what I like and I guess H-E-B. Is that the right answer?

Darryl: Fair, fair enough. You cannot go wrong with H-E-B because you cover everything.

Tom: That’s right. I’ll take H-E-B as my answer then, Darryl.

Darryl: Love it. Thanks for hanging out with us. This was really cool.

Tom: You bet. Enjoyed it very much.

Darryl: I think everyone will really enjoy this podcast, so I look forward to airing it.

For those that have stayed with us till the end of the show, thank you. You’re listening to Retire in Texas, and I want to remind everyone to visit PAXFinancialGroup.com. And, again, you can text 74868, put in there “TEXAS”, and we’ll have an advisor reach out with the heart of a teacher and just have a chat with you.

And I want to remind you, in the midst of all the chaos, to think long term. Have a great day. [25:07].6]

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