Handing Over the Reins with Helen Thompson


After decades in the game, your business becomes part of your identity.

So how would you feel if your business crashed into the ground after you handed over control to someone else? It’s like losing a limb.

And what if that “someone else” was your child? Imagine how a failing business could damage your relationship.

That’s why it’s so important to hand over the reins early and slowly, especially if it’s your child. If you do, not only will you get more time to spend with the people you love, but your business will thrive long after you retire.

Today’s guest Helen was in the media business for decades. Now she has successfully handed the business down to the next generation, and she’s here to show you how to do the same.

In this episode, you’ll discover how early preparation lets you hand over control of your business without drama. You’ll keep your legacy, your business will grow and you’ll finally be able to kick back and enjoy retirement!

Listen now!

Show Highlights Include:

  • How to instill a strong work ethic in your children (even if they don’t pay attention to a word you say) ([3:23])
  • The “reverse reward” schedule that turns lazy, spoiled-brat kids into diligent sweethearts ([3:50])
  • Two surprising character traits that let you excel in business (even if you’re not a driven person) ([8:43])
  • How to land your first clients as you pivot from employment to entrepreneurship (even if you’re afraid to sell yourself because you were an employee for the last 18 years) ([12:23])
  • The “risk reversal” method that attracts business and lets you retain clients for longer ([13:41])
  • Why handing the reins of your business to the next generation creates freedom, a stronger business, and a lasting legacy ([14:46])
  • How to transition your business to the next generation without damaging client relationships ([18:40])


DLP033 PC - Handing Over the Reins with Helen Thompson



This is Darryl Lyons and you’re listening to retire in Texas. Thank you for joining us today. I’m excited about today’s show and I want you to know that today’s show is sponsored by PAX financial group. So be sure to visit PAX financial group.com for more information, and, and also you have to know the disclosure, this information is general and nature only is not intended to provide specific investment or tax or legal advice for that matter. So be sure to visit PAX financial group.com for more information. And also finally, if you need to speak with one of our advisors, there’s no cost for this and it’s they’re, they have the heart of a teacher and it’s 15 minutes. You just text the word text to 7, 4 8, 6, 8, that number 7 48 68, and just put it in Texas and we’ll connect with you. Okay. So right now I’m excited cuz we’ve got Helen Thompson and she’s gonna share her journey on, uh, being a successful business person in the greater San Antonio area. So thank you for being on the show today. You’re Welcome. 


([01:10]): Okay, so now are you from San Antonio originally? I’m a native Native. Yeah, we don’t get too many natives. A Native. So where did you go to high school? Let’s see, I went to high school for two years at MacArthur and then graduated from Edison. So MacArthur, was that kind of in the sticks back then? Like was it yes, it was right. It was. I tell Brandon that we used to catch the school bus and the children from elementary school, middle school and high school rode the same school bus and from Hollywood park over to Wetmore road. That’s how the route was. That’s how many people we picked up.  And did you grow up in Hollywood park? Mm-hmm <affirmative> three blocks from him. So you actually misled me. You’re not a San Antonio native. You’re a Hollywood park native. Well, I lived over by Kelly field until I was 10 Kelly field, which is now port San Antonio. Yes. So that was the maroch area? No, it was like old caster hill road, old caster hill, like on the way to Castorville, they built this new super duper cargo plane called the C five a Uhhuh back then it was the XC five, a mm-hmm <affirmative> and they took our land by eminent domain. No kidding To build the runway. And so then we moved from the deep, deep west to the far, far north. Yeah. That is quite a difference. Not only in distance, but in culture. Yeah. Okay. So let’s go back a little bit when you say we, so it was your family when you were younger mm-hmm <affirmative> and so your mom and dad, what did they do? 


([02:31]): Uh, mother was at civil service and my father was in fire prevention, sprinklers. That’s right. We talked about that a little bit cuz my dad also did fire suppression in sprinklers. Yeah. For a long time he worked for a company called Smith back in the eighties. This was Texas automatic sprinklers. Okay. And so which is a great business and uh, I, I enjoyed it being a civil service. Was your mom, was she working at the time at the Kelly at Kelly air Force bank? Yes. And I’ll tell you a story about my mother. She was amazing. She was the first female GS 13 at Kelly field. No kidding. Like I’m gonna say in the early sixties, That’s a big deal, especially like A low bird Colonel. Yep, absolutely. Yes, no, that’s a real big deal. And especially kind of considering that era. Um, Oh, you had to know her. Is that right? Oh yeah. So what did she teach you about business and money in general? Did she sit down with you and teach you this, these skills? 


([03:29]): No. Maybe just, um, just by being around mother and daddy work ethics. I don’t, I don’t know. So Did they have different work? Ethics means different careers. One’s entrepreneurial one’s government contracting. Both have to have good communication skills, good work ethic. But did you see a contrast in the way they work? I don’t think I paid attention. Yeah. I mean, well what about money? I mean, that’s a pretty decent income generally. Did they ever sit down and say, okay, Helen, here’s how you open a checking account or did you just learn through osmosis and observation? I think I had an allowance 

Maybe. Okay. Yeah. And it was an allowance where daddy gave me, it was probably big then maybe $5 a week, but, and I had chores assigned to them. So if I didn’t do a chore, money came out of that $5. Okay, good. Yeah. Yeah. I don’t think he ever really did it, but <laugh>, I do say as a father of four, it’s easier to create systems than implement <laugh> so growing up that’s Um, they were upper. I, I would say back then, I never wanted for anything. Yeah. I, I guess middle, Upper, middle upper mm-hmm <affirmative> so did you have siblings? I had a older brother. He was yeah. 11 years older. Okay. Has he since passed? Yes. Okay. I’m sorry. It’s sorry. So 11 years older. And so there’s obviously a difference in perspectives growing up. Yeah. He had to babysit me. I Was gonna say, yeah, he was almost like another parent, right? Yeah. 


([04:45]): Well, yeah, except for he did things like throw me in a pig pen and stuff like that. Did He really? Oh yeah. No. So are you telling me you had a farm? Daddy had, uh, pigs and then there were bras behind us, so Okay. And they had chickens. Okay. So a little bit of a farm. He Come from a little town called, um, Deanna. So he was raise farm on a farm. So I’m from Castroville, which, you know, ended up going to be valley. I mean, from a lot of places mm-hmm <affirmative> but ended up graduating from Bidina valley in Castroville. So to hens I’m very familiar with, and so that’s where he grew up and then he ended up moving to the country of Hollywood park.  Well, first he moved to the west side. Yeah. First, first Kinda be on highway 90. Yeah. Okay. Yeah, exactly. To Henne all the way to highway 90, uh, Kelly, which is now port San Antonio. And then ultimately going up to Hollywood park, you went to McAllister and after McAllister high school Parents got a divorce. And so then I changed schools. That’s tough. So where did you ended up graduating? High school. Edison. Edison. Okay. And then after Edison, what did you decide to do? I still haven’t decided <laugh> you’re still working on it. Oh, you know, my parents basically said, you can go to college, you can get a job, do whatever you want. So they weren’t push me any direction. They Didn’t. Well, you know, coming from two different perspectives, I think that’s kind of healthy. Hey, look, one’s a safe route. Relatively speaking, the civil service. Mm-hmm <affirmative> you get your check, you get your pension, you get your health insurance and the other’s an entrepreneurial. So, you know, they just said whatever you decide they weren’t dogmatic about either one. Is that correct? 


([06:14]): Yeah. I kind of regret it cuz most of my peers went to college, but I’m not certain they were any more successful in long term. Yeah. Maybe in the short term they were, but I don’t, they’ve done pretty good. You have a very, I did successful reputation and uh, going, doing good work the right way. So when did you get into the media business? Okay. So when I was, uh, 19, I moved out to San Francisco for a few years. This is in the mid sixties. Okay. And lived with my cousins and got a job out there and I had a couple of temporary jobs and then I went to work for a TV station called K P I X. And I think it might have been the CBS affiliate. Okay. And back then I was called a traffic coordinator. And not in the terms of traffic like cars. Yeah. But like scheduling commercials. Okay. So that’s called traffic and I was there for quite a while. And then I came back to San Antonio, maybe four, four years, five years later and got a job at a radio station. Okay. Here in San Antonio. Yeah. And did traffic there and was there for three years and one of the account executives, which really were sales people. Yeah. Yeah. Can’t live without the sales executives. No. Went to an advertising agency and hired me to go with him. And that’s how I started in media. So I just was at the right place at the right time. You really, and specifically thinking about San Francisco and how they were probably pretty advanced in their media markets at the time. Oh yeah. I had no idea. It was more of a clerical function. You learn how to schedule commercials in a quarter hour. Yeah. And the, think about the technology back then and how it’s changed over the years. Yeah. 


([07:48]): I can tell you, we had a big piece of wax on the wall and it had five minute increments and quarter hours. And you hand wrote in commercials with a red wax pencil. 

No kidding. Not very many people know that that’s interesting. Then when somebody came in and paid more for the same commercial, you could erase that wax, put a new guy in there and move him someplace else. Interesting. Now I’ve bought media before and a lot of people listening don’t realize how tedious and specific, I mean you’re selling specific times and you can’t go over those times because there’s people expecting to own 15 seconds and 20 seconds and it’s you gotta stay on top of it. You do. And then, and if you don’t, they don’t pay for it. Exactly. And so you learn these skills, attribute some of the advanced marketing and advanced business in San Francisco to probably helping you hone these skills and earn some credibility. When you come back to Texas and then an advertising agency gives you more skills in education. And then there was a certain point where you decided to go out on your own. When was that? And what was the catalyst? Well, I worked for an agency called the pit luck group for 18 years, but I came and left a couple times. One time I worked in marketing for Sanco theaters. Oh Yeah. And another time I did sales for K B a T radio. Okay. Which is now K C Y Y. Okay. But both times I went back to the agency. I think I was very fortunate to work with two gentlemen. Both of whom had advertising guys, but they had their financial degree from Wharton school of business. Okay. Not a typical combination. 


([09:18]): Not No, but they, you gave me so many opportunities and they enjoyed my work ethics and my attitude. So they allowed me to grow. That’s cool. You know, it really does take for granted just the idea of somebody coming along in life and just giving somebody else a shot. Oh they did. They were amazing. In fact, you asked me when I started the company, when I started the company and, and you’ll see with my personality, I was, I’m not a driven person. It’s just like, I wanna do a good job and I wanna please people and I want, you know, blah, blah. That’s fair. That kind of thing. That’s fair. Yeah. But they’re the ones that encouraged me to start my own business. No kidding Uhhuh. They said you can’t go any farther in this company. Why don’t you try it on your own? And I kind of had that attitude. I’ll try this. And if it doesn’t work, I’ll get a job. Did you always think in your mind, maybe you admitted this or not? Did you always think my mom was grinding and I can do it too? I absolutely know that my mother is part of the success. Yeah. 

Because she loved me and she encouraged me. But in the same time she had pulled me back every once in a while. So I was never, never quite good enough. Never quite met her standard. It’s not ugly, but pushed. I’m aware of it now. I wasn’t aware of it then, but it  Pushed you. Oh, she did. And it kept pushing you even then when she wasn’t there. 


([10:33]): Absolutely. Yeah. My son has heard me say that a lot about my mother. I wanna pause for a second and get to this. Um, but it just says those that are just tuning in to retire in Texas, please text 7 48, 68, the word Texas. And one of our financial advisors will give you a 15 minute consultation to help and guide you. Now we’re here with Helen Thompson, with Helen Thompson media and she had just alluded to him and she pointed over to her son cuz Brandon Thompson sitting over here on the couch, hanging out with us today. So this is kind of fun. So this is the next generation of Helen Thompson media. And I wanna go there and share with the audience, this transition that’s taking place because this is one of the biggest challenges specifically as we’re seeing a demographic shift from the baby boomers, shifting the leadership to the next generation. And that’s something that you’ve been working on for a number of years. How difficult is that? Well, I think my ego kind of got in the way. It is difficult because when you have your own company and you’ll find out, oh yeah, that that’s like part of who you are, Even if you don’t wanna admit it. No, but that is, that’s an important part of who you are. So, you know, I used to be Helen Thompson, Helen Thompson media now I’m grandmommy. Oh yeah. You know, and now I’m like, he’s my boss, Brandon’s my boss. But in the same way, it was a 10 year transition. And it mainly you got outta college, you got few jobs from some of my friends. And when I ran outta friends to hire him, I had hiring 


([11:57]): <laugh>. So you weren’t the first choice Brandon <laugh> <laugh> no, but then, um, I guess it was, when did you start working? 2000 2, 3 1. And then maybe by 2010, it was a 10 year process. And it was just hard for me to give up. I kinda like to work four days a week and then three days a week. And, I really wasn’t working. I just didn’t know what to do with myself. So I wanna come back to this transition piece. But before I do, let me make sure the audience understands the scope of your business. So as you started to build the business, you were going to organizations that really had been established in San Antonio, maybe even beyond. And you were saying, I can help you with your advertising in a very efficient, effective way. Tell me a little bit about your pitch, generally speaking, how did you talk to these businesses? How did you convince them to use you and how did you add value? Well, first of all, I had an 18 year reputation. Mm-hmm <affirmative> my name because I worked for an agency and I did the media. Secondly, I was not good at initial cold calls. I did it because I had to, but in the same breath, I got several references from vendors, media reps. And if I can get a reference, I can sell myself. It was just hard. Yeah. So the years of experience, the research tools that we had, you know, to be able to chat and yeah know the lingo and I worked on so many different types of accounts when I was at the agency, there was probably not too much. I couldn’t talk about it. So in various industries, right mm-hmm <affirmative> or was there a niche industry that you worked on the most? Was it automotive or Um, well, automotive aftermarket. The Cavender car dealers. Yeah. McDonald’s was my first. Okay. Pearl beer. 


([13:41]): Is that right? So let’s take Pearl beer for an example. You might go and say, Pearl, I can go to all these radio stations and maybe even television. I have a relationship with them and I can get spots for you and get you the maximum exposure that you’re looking for. And that’s the role you would play. Right? That was the role we played. But I also tossed out some guarantees in there, like, oh, if the spot doesn’t run exactly as ordered. Yeah. We’re gonna take credits or we’re gonna get twofers back. Yeah. Okay. That’s a pretty standard pitch. I would say with me and my competitors at the same time, I really did it. 

You looked and made sure that those Spots running and that’s one thing we called it. Post-analysis yeah. Nobody like doing it, but you get those affidavits and you go through spot by spot and match it to your order. Yeah. Because they could really bump you and you wouldn’t know it cuz you know, the purchaser doesn’t listen all the time. And so you would be an advocate and make sure that those spots were running. Right. Did our best, Did you ever help coach, like, let’s say Cavender as an example, did you coach them on what to say or how to say it? Well, that was when I was at the agency that I handled us and there was, it was a full service agency. There were about 70 of us. Yeah. And so there was a whole team. So as the marketing and advertising world has evolved just like everything else. Now the technology piece is crazy with whether it’s podcasting or Facebook ads or everything. How do y’all keep up with this today? I don’t, You don’t have to worry. That’s your son’s responsibility. 


([15:05]): Almost like if somebody asked me to buy media now and how you could add the various audience deliveries across the various types of media, I’ve been there done that I don’t wanna learn. We’re Gonna have to get Brandon on to talk about that. That cuz that’s a whole nother Animal. It is. It, it is. And in fact he has people that specialize in each one of those categories, as opposed to in the past. I remember when we first started using digital and it used to be, you would buy a TV schedule, the TV stations would force you to use their digital aspect. Oh yeah. Yeah. So that’s how we were involved. We got that as either. Yeah. It’s changed. So then I also wanna understand being a mom and doing this. How was that? I mean, what would you tell the other moms that are grinding it out, running a business, raising their kids. How do you do that? What, what advice might you give them? Do you mean when he was working for me or more? Yeah, I’m kind of bouncing around in a timeframe Here. I busy business to participate in his life. Maybe not as much as it at home mom, but the advertising, it offered flexibility of, You know, did you make events? Were you there? Pretty much. Yeah. And So did his athletic programs? Yeah. Things Like that. Yeah. So yeah. You were able to be involved and I, I Was. So do you think that it’s 


([16:16]): Not as much as I see the mothers these days and I see how much they’re involved and it makes me almost think, Hmm, I was inadequate, but I wasn’t, There’s a tipping point maybe too much. Right. Uhhuh versus Brandon and knowing him over the years, I would think he’d agree that you were involved in, you know, role model. Mm-hmm <affirmative>, he’s a pretty laid back kid. Yeah. Well, you know, I wanna make sure that female entrepreneurs out there, I understand that it’s doable. I think that oftentimes they hit this in their mindset. They, you know, we all have these doubts and I just want to, you know, just make sure that the females out there that are saying, I want to start a business, that they can and still be the mom that they called to Be. I think they can. And I think it’s, I don’t know that it’s easier now than it was back then because I never, you can see my energy. I did, I’m just trying this and I’m gonna work hard and it’s gonna work. And if it doesn’t, I’ll do something else. So that was a gift I had or some blessings from above. It really is. And, and you know, the idea of being a people pleaser can hurt and help you. But to your advantage, you just wanted to make things right. For people. And so you wanted Your business to grow. Yeah. You know, what happens in advertising is when business is very good, the retail merchants and, or fast food, whatever they are, they think it’s because they’re doing such a good job, but when business is bad, they don’t think it’s them. They think it’s advertising. Isn’t that ironic. It’s not right. Yeah. That sounds like, uh, being a financial person. So I get that <laugh> Yeah. You’re right. 


([17:38]): So when did you decide? And maybe it was, it evolved over time, but when did you decide it’s time to start transitioning? Like was there like a light bulb moment, like a client yelling at you? Or was there something like an epiphany? I think there was always a plan in place. Yeah. Brandon probably told you we lost Mike in 2006. I think I would’ve been out of the business sooner. Mike being your husband. Yeah. Brandon and dad. Yeah. 

Yeah. And so I would’ve been out of the business sooner, but cuz he had already retired. So there was some things that happened. I mean, I was sure I was ready to get my money that I earned when I was 65. Yeah. Yeah, exactly. So it was just, I think if I could summarize, there was a series of events, but as I know it, it kind of happened over time. It was phased to a certain degree. It was. And Then first year I made no money. Mm. There you go. I think we got a loan on our boat and something else so that I could like to buy a computer. So You’re talking about the first year of Business. Yeah. Made no money. Yeah. And then I picked up a piece of business called garden Ridge part, which is now yeah. Garden Ridge part. Yeah. And that kinda pushed me over, got me going. That’s a whole nother story in and of itself. But in terms of the transition, the transition, you phased that to Brandon, right? Absolutely. Yeah. And I think that also helped your clientele become that they accepted Brandon as well. Oh yeah. I had been there for, I don’t know, 2001 to 2000. I’m just gonna say 14, 15, 14 years. Yeah. There was no confusion as to what was going on. 


([19:05]): I think that’s a wise thing to do. And rather than, you know, flip the switch now, the transition’s pretty much fully done. Right? Absolutely. Okay. So now what’s this next chapter for you? I’m just fortunate. You know, my blessed husband saved money. He always said I could make money and I could spend money with that part in between <laugh> I didn’t do real good <laugh> and he Did that, but he was a saver. And so he probably taught me some good habits. If I were to recommend to people that are 35 and 40 years old, save money outta your paycheck before you ever even see it. That’s what Mike Did. I’m with you. Yeah. I mean, I Didn’t, you know, his college was paid for and I didn’t even know we were doing it. That’s so cool. But that was his discipline. No mine, but I think saving money and being a little property, buy a home. Yeah. Would your next chapter in your life be focused on the grand babies? Is that the priority? Well, they’re not babies anymore. No, I know. Right. They’re big. I don’t know what I should focus on. I just have a good Life. Would you say BR? They can’t hear Brandon, but I’ll repeat it. What would you say? Her focus? What do you think she’ll be doing? She has to be doing something. Yeah. <laugh> Yeah. I’m on the social committee. I do the newsletter For the company. No, for The, for my neighborhood. For The neighborhood. Okay. Yeah. I coordinate the social activities. There. That’s a great role for you, But they’re not those aren’t like, it is a commitment, but it’s not like you’re on a board of 


([20:26]): Directors. There’s no anxiety associated with it. There’s no pressure. Yeah. So now gosh, there’s so much, I want to ask you, but cuz there’s so much substance there about starting a business, being a mom, the impact that your parents had on you. It’s just so cool to me. And then the transition, but there’s, we’re doing a lot in 22 minutes here. <laugh> that’s okay. But I do have probably the most important question I’m gonna say for last, what is your favorite? Salsa. Salsa. Salsa. Arriba. Arriba. It’s a brand. Yeah. Okay. I know Reba. Yes. I know Arriba, but they were toasted and it’s medium, but it’s like roasted tomatoes. That’s Good. It’s kinda like the stuff at Rosario’s a little bit, A little bit. I mean I’m sure Rosari is bitter, but the kind that you can buy. Yeah. Yeah. Good. I love, I actually love that and I know exactly what you’re talking about. My wife, if she listens to this, she’s like, you know that because you eat it all the time. Well, Everybody has a favorite. There’s no such thing as a bad salsa. I really I’ve yet to find a bad salsa. So there’s salsas. You prefer, but do you like yours hot or no medium. No medium. Not Hot medium. Well, Helen, this has just gone by too fast. Well, there’s so much to cover Here. I know I was just a very fortunate person of my faith and yeah, my family and What a blessing drug me with it. Yeah. Thank you so much for being here and thanks for being on the show today. Wish I could give you some profound statements. So you did how to be successful. I don’t Know you did. You absolutely did. So for those that are listening, you’re listening to retire in Texas with Helen Thompson and Helen Thompson media who has successfully ran a business and transitioned. So we’re happy to hear her story and we might have to have her back on based on the, uh, the request from the audience to dig into that a little bit more, but thank you so much for being here and for those that are listening, I just don’t wanna remind you as always, you think different when you think long term have a great day, 


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