Chester Drash: Lessons from building and selling two businesses

Have you ever noticed how common retirement advice ignores business owners?

Even if run-of-the-mill retirement advice makes financial sense, it can leave you emotionally unfulfilled.

It feels like most financial “gurus” forget that our business is a part of us. Quitting a job doesn’t even compare to selling your business.

It’s not only about selling. It’s a fine balance between finances, legacy, and finding a buyer who won’t destroy the business you worked years to build.

Chester Drash knows this better than most. He’s built and sold two businesses in his life, and he’s here to share his experience with you as he approaches retirement – so you avoid the pitfalls that conventional retirement advice ignores.

In this episode, you’ll discover how to exit your business in a way that secures your financial freedom, protects your legacy, and maintains your relationships.

Listen now!


Show Highlights Include:

  • The simplest “owner salary” calculation that tells you how much you should pay yourself now (so you don’t retire with a side job) ([9:33])
  • How to safely hand over your business so the buyer doesn’t destroy what you built for years([15:17])
  • Two assets you must own outright if you want to eliminate 90% of financial stress in retirement ([17:25])
  • The “money script” you developed as a child that controls every financial decision you make today ([19:13])




Do you want a wealthy retirement without worrying about money?


Do you want a wealthy retirement without worrying about money? So welcome to the Retire In Texas Podcast, 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.


([00:29]): Welcome to Retire in Texas. My name is Daryl Lyons. I’m the co-founder of PACS financial group in San Antonio PACS. Financial group is this sponsor of this program. So visit PACS financial group.com. And before I get started it, I need to share the disclosure. This material contains general information only and is not intended to provide specific investment tax or legal advice. Visit PACS financial group.com for more information, investment advisory services offered through PACS financial group. So I’m excited to talk with Mr. Chester Ash. Who’s been a long-time friend and neighbor, and really a role model in the community for doing a lot of good work and helping make San Antonio and a greater San Antonio community. A good place to do construction. We’re gonna talk about his business cuz it’s certainly not construction. It’s more consulting in interdisciplinary. So we’re gonna get into that a little bit, which I think is really cool. And I could probably nerd out on that because of the time I spent in parts of Brook city base helping the development there. But I really want to start out by diving into who Chester is. So Chester welcome today. Thank you, Darrell. I’m glad to be here. So


([01:36]): Did you, I actually don’t know this. Did you grow up in San Antonio? No. I was born in Brownsville, Texas, and for a lot of folks that don’t know Texas, the Southern most city here in, in Texas. I tell people that my mom is break now. 51 when they moved from Morgan city to Louisiana to Brownswood, my dad was a shrimper commercial shrimper. And it was easier for them to fish out of Fort Browns because it’s a seasonal thing during winter months coming up, the boats would, would go down south along the Mexico coast. Yeah. Way down in Campeche and, and fish summertime they’d be up along the Texas coast, but when they were in Louisiana, I mean to come down all the way, this way, it was like a, a three to four day trip on the boat. And so they just the whole family. So my little brother’s born there. Then I was, I was born in Brownsville. I tell everybody I’m kind of a Cajun roots as well as Texas.


([02:32]): Yeah, that is interesting. And so there’s a port in Brownsville. Excuse my ignorance. Yeah. Port Browns. Cause I think of port Isabel is kind of the point there. Yeah. There’s a port Brownsville, which is a much bigger report. It may be about the size of Corpus it’s it’s been the years. Just didn’t know that, but port Isabel is a smaller, probably more of the fishing ripping community. Yeah. You know, and then of course, years ago the, the army had Fort brown there, which became a hotel and a convention center or something like that. There’s some history there. And so your parents were both in the fishing industry.


([03:09]): Well, my mom stayed at home, which I guess was typical that’s but my dad and I would say my relatives, they read the shrimpers or they worked on the oil platforms out the Gulf. Yep. Or they ran supply boats to, and from that was pretty much the working that they did back in that day.


([03:28]): You don’t have to go far out. You can stay in the goal for plenty of shrimp, right? Oh yeah. Yeah. So there’s plenty there and I’m sure the technology changed since you first did it, but were you going out, out with them growing up? Were you offshore, did you like as a kid? When I was


([03:43]): Small, I, I would go cuz as a kid. Yeah. You know, I want to go, you know, neat. And then it was just fun to be out there. And he would take me out when he was on a short trip. But most of the time you were out the, anywhere from two to three weeks to two months, you know, you just loaded the ice and groceries and, and, and, and went out, tried to catch shrimp. And if you caught shrimp, you made money. If you didn’t you know, it didn’t happen. So it was all commission based kinda work. Yeah. And is that where you learned your entrepreneurial skills?


([04:12]): Well, you know, my, I look back and obviously my dad had those skills. He had his own boats in, in 40 to know, 51 ish and maybe maybe 54, but then he lost the the bank took him away cuz he didn’t, wasn’t making money, couldn’t catch whatever. So, so I found out he had couples and lost them. Then he went to work for a company and was the top producer all those years. So he was he was very driven, you know, and but looking back, I didn’t really know. But when I decided to get out of, of a first year of college, I didn’t wanna go back to college. And so I went home and he said, well, you’re not sitting on your butt all day. We’re going to work. And then we were, I guess, doing well.


([04:58]): And he wanted to try to go buy another. I think it was because I was with him now. Oh, do that. Then he had a heart attack. And of course after that, nobody wants to lend your money, stuff like that when you, when you have that kind of history. So but then you know, he pushed me hard though, not to do that work. Gotcha. Which I gotta thing both of them. Cause they didn’t go to college. They finished my dad 10th grade, my mom’s seventh, but they pushed and glad they did because I wouldn’t be where I’m at today. And but he didn’t want me to have that same life.


([05:32]): Yeah. It is. It is feast or famine it and it can be rough. And I know people who have been in that business, I don’t know many today, but I have known people to be in that business. And I know the challenges that exist. Did they ever specifically talk to you about money?


([05:47]): We were never in conversations of such. Yeah. you know, wish, wish that would’ve been. Cause my two kids we did have an, and they’re, they’re doing very well on their own. Right. And, but when I went to work with him full time for a couple, couple years there, then I got to understand a little bit more about maybe how they kept things financially. Good. Because we, we had clothes, we had food. I mean, I used to say, well, why can’t we have a swimming pool? Like D and them, you know, why can’t I wear these kinda shoes? And you know, I can’t remember all the details about it. They had kids and I did, or I converse or they didn’t, or I can’t remember, but you know, you kinda like as a kid, you don’t know, you know, and, but I made good money when I was working with him.


([06:30]): And I was the low man on the pole. You had the captain rig man, which is kind of the middle then the, I was the header. And so the header got paid by head and shrimp and, and I migrated up to the next level, but I went out and like, like I give an example back. And this was probably 71, 72. I went out 10 days, 24 hours. And I made $15,000 when in 1970. Oh my goodness. Yeah. 10 days of shrimping. And I don’t know what he made, but you know, I’m sitting there like that and I’m all excited. And he goes, son, you got, you know, you need to save your money. He says, he and he made save me. He says, but that’s what I have to do. He said, I don’t make good money all year round. So I’ve gotta put some aside plan ahead. And, and that’s probably the only education I got at that time of my money still


([07:22]): Helpful. I mean, that’s a good, powerful lesson. That’s a lot of money too. Holy cow. Was there any low points in you growing up that have made you who you are today in your decision making?


([07:33]): No, I think I had a pretty good childhood. I mean, typical childhood and but I don’t regret anything. It that, you know what I turned out to be, I think turned out really great, you know, I wish my dad would’ve been alive longer to see some of this. Yeah. And I think it’d been extremely proud, but make life, doesn’t always give us that chance. Sorry.


([07:56]): I think he would be proud. And I wanna transition into some of that. Not only you professionally, but personally, I know transitioning a little bit into your career. I don’t think it’s official that you retired, but you did sell a business on your professional career. How long ago was that?


([08:13]): Well, I did it twice. It’s one of these things where I went to work with a lot of folks and my profession and went up to their for levels of became a project manager and a VP in the firm. And we were bought out by a British company, the firm I was with at the time. And this was in 89. I think it was. And they pretty much came in, decimated the firm the way they operated, the way we did business in the us. I mean, it, it just and people were bail out the, and so I don’t think I had any that, Hey, I’m gonna go start my own business, but it was one of those things where it’s like, Hey, I’m gonna go do it. I mean, what else am I gonna do right now? So I jumped out and I had the 401k or, or factor the, at the pension plan.


([08:57]): Okay. Yep. One was then where the company provided. Yeah. Retirement monies. They’re more prevalent then than they are today. The pensions. Yeah. And then I ended up so I had some, a little bit of stock. I was like maybe number 33 out of the top. And I had to, to live with the noncompete, like all the other. Yeah. I kind of argued at the, at the merger meeting is like, Hey, I’m a little bitty guy. I said, I’m not making the millions that you guys are. And I gotta, I have a three year noncompete. I said, that doesn’t sound fair. Of course I lost. I didn’t, yeah, I didn’t win. But, so I stepped out and built a firm and drag asked consulting engineers from 92 to 2004. I grew it just starting off cashing in my, my money I had and put it in the bank and just took out money each week so I could live on it.


([09:48]): And that was my salary. And I said, if I can’t, if I run outta that out of that, then I’ll go back to work and where they, so, oh four, I had 120 people, three offices, we’re doing close to probably about 10 million in revenue. It’s all in. And then I had a big company come along and, and buy me from outta state. They were in I don’t mind. Can I say the name? No, you you’re. You you’re welcome to. Okay. Well, anyway, Terracon, they were a nation and why came knocking on my door and made me a good offer. And so I sold, stayed with them seven years after selling I was put on their board, I was in charge of a Texas division. So I went from my three locations to nine offices, you know, to, to manage.


([10:33]): And, you know, at seven years I just, I went ready to retire that time. Maybe 55, I guess. And I decided that, you know, I’m not ready to retire, but I can move up higher. I mean, it’s like, I was kind of sty and that then my entrepreneurial spirit jumps out again. Yeah. And I go home until Jill, my wife. And well, I’m gonna leave tire, I’m start. It’s like, I’ve heard this before. And she’s not a, she doesn’t use bad words, but her excluding you’re doing what you know. Yeah. So I did, and I started draft consultants and and that was by then 2010. Okay. And then all this time, it, same kind of business that we were doing you, this one’s by yourself or did you start it with somebody else? No, it started with me and one other person and then, and we grew it to that, but then we sold and then we, then I started up again on my own and I knew I’d do okay.


([11:30]): But I wasn’t planning to, but to do like I did before, but in the same in in 2016 the company I’m with now TTL based outta Alabama, they came knocking. And so from 2010 to 16, I grew it to almost the size. I did the old company in shorter time. And then a lot of that was because I had relationships with clients. You kinda know the angles and the roots that you gotta take. And then they came knocking. So I merged with them too. And at that point, I, you know, I was 60 years old and it was kinda like, well, but not bad deal. I mean, I did two firms and sold, both did well. And my friends and colleagues in the business go, what do you, you know, like you build this and you sell it, you know, he says in their legac y or, you know, your kids.And I said, well, my kids didn’t wanna be engineers. And I said, legacy. Yeah. But I said, I’m an engineer and a businessman. And I said, I can always do my engineering, but I may never have an opportunity to, to sell a business you or sell that a good price. And, and that’s how I looked at it. So it didn’t really bother me that I was selling it. Because again, it put me in a position to be financially sound and stable going under retirement here. It’s


([12:45]): A really good point that a lot of business owners wrestle with. And it’s neat to see you have that clarity because a lot of business owners are still hanging on to the dream of their kid taking over the business. And that’s a lot of pressure on everyone. And oftentimes it’s not a good fit, but maybe the kid doesn’t have anything to do. So he jumps in this or her into this role and it can be very disruptive. So for you to say, you know what, my end game, which Steven cuby says, be begin with the end of mine is I’m gonna sell. And to another point that you made, I think is very helpful. We talk about legacy. A lot of business owners think, okay, my business is my legacy, but it’s my conviction that a legacy is not what you leave to someone, but what you leave in someone. And so I’d like to kind of tease that out a little bit more as you’re now, now in the third I’ve lost count third or fourth career now, more or less, what does this next chapter look like for you in the next few years?


([13:45]): Four or five years? Well, you know, the presently president of DTL when I sold in 2016 I became their COO and then a year ago, right before COVID. So it was pretty close to February. No, actually it was almost a year and a half now, I guess, became president. And right now my thoughts of retiring, stepping down are, are coming more prevalent. And I like what I do, but I can also feel that the, the, the body’s changing, you know, and and I feel like anything else it’s, I’m not an athlete. So, you know, can’t, your body isn’t work, right. You won’t be as good. And, and I think being an engineer, if I don’t have that capacity, even as a business owner, I think I need to step down, up, down when things were good.


([14:35]): And so I possibly for sure by the end of next year could be mid-year next year. I, I don’t know, but I’m pleased where I’m at, but it’s time that comes, that you’re worried about cash worrying about someone trying to Sue you, someone, we got 200 vehicles on the road all day long, and we’re on, we’re in the Southeast us all the way to Tennessee over. And, oh, I didn’t, I mean, drill rigs, I mean, things happen. You gotta continual manager. I got great people. Don’t get me wrong, but there’s the point where it’s like, yeah, you know, I’m ready. I’m ready to say


([15:12]): I’m done. And does that, I’m sure this is a factor. And how much of that is that decision making of when to hold a trigger, has to do with you feel comfortable that somebody can take over your role? Is that a big part of it? Or are you just gonna say, they’ll figure it out in another extreme,


([15:31]): Well, with the firm I’m with now, and it’s a smaller firm than te is like a, almost a, a billion in, in revenue. They’re all over the place all over the us. And TTL is just in the Southern us. And we got about 400 people Revenue size, more or less, or no revenue TTL is about 55, 60 Re respectable, but still not. No,


([15:52]): My other, you know, when I sold the Tercon and TTL were, were approaching 10 billion. So yeah. Yeah. It’s size wise. If I was still with my preview, my own, my own companies, then yeah. It’d be like, you know, can I pass the torch? If not, then do I need to sell the thing? Whereas with Uhl, we got good people in place that, yeah, that would, that won’t be


([16:16]): A problem. Cause that takes a lot of pressure off you. A lot of business owners, they will not pull the trigger until they have a hundred percent conviction and confidence that there’s somebody in there to step in their shoes. So that that’s one less thing you have to think


([16:26]): About, but that’s a natural tendency for every business song. You know, I still, today there’s certain clients that I’ve dealt with the relationships there until I was sure that I could pass that torch, that they’re gonna take care of that customer. And you know, not the business, just that customer then you, I can’t do it yet. So I think there’s something, a trade in all owners. And it’s a good trade. I mean, I think you don’t wanna bill some and then somebody destroyed in a matter of seconds.


([16:52]): Yeah. That’s I can appreci that. Being a business owner, especially since you put your whole life into it, do you find that as you make these transitions and specifically the next one, do you find that you’re gonna struggle with your identity? Like I’ve been a business owner and engineer my whole life, and now who am I, what do you think about that part of it?


([17:09]): You know, those are the things you have to overcome. And and that’s part of the things I went through even to get where, okay. Yeah. Let’s plan a time for call the call it quits. And the party thing, I guess was, what am I gonna do? You know, money now that I’ve sold, done? I mean, I don’t have enough money just to, to go willynilly and do everything I want to do, but that stress is gone because I know that, that we, okay. I think anybody that wants to retire you need to make sure you’re debt free. Okay. And, and when I say that, you know, the, your house and generally your cars are your biggest things that most people are gonna have, and you can have those out of the way then that takes a lot of stress away. Because again, whether you want to or not, you can change your lifestyle if you have to. But if you have, if you don’t have a house, you don’t have, you know, say a car, then you gonna have a lot of stress there. Yeah. Just


([18:04]): Adds to it. Do you, has there been some tricky money decisions in each of the transactions that were confusing or hard to figure out? Sounds like you kind of resolved one of ’em, but the squiring money away to start a new company seems like a tricky one. Was that hard for you? Or you were just rational. I mean, you basically said I’ve got X amount of dollars. I’ve got six months. And after that I’m done. Right. Or whatever that number was. Yeah.


([18:26]): Well, you know, you, no matter what you started I’m mean we, you got a certain amount of money and if you can’t, you don’t get things move along. I mean, how long are you gonna let that bleeding go on? And so starting new branch officers, I mean, it was making money, but you’re gonna use the profit to do those of the expansion. And so it’s the same thing. I mean, if you’re gonna go into retirement I’m trying not to use any of that. You any money right now because I’m working and salary. So I don’t want to dip into a lot of the other stuff, but if you’re dipping into your retirement and you’re still working and whatever, you, you really need to sit back and say, Hey, wait a minute. I need this money to live on. So people don’t think of it that


([19:04]): Way. It really goes back to your dad teaching you that shrimp money and how to squirrel some aside. And you’re right at the time, we probably, we don’t realize a grasping. Yeah. I think a lot of that you know, is stuff that you can, maybe the back there, remember it


([19:22]): Stays there. There’s some money psychologists that are started to talk about that being called a money script. Yeah. In fact, part of why I ask a lot in this dialogue, because I realize that as I tease things out, I start to understand that some of these lifelong lessons have made a lot of people are transitioning into retirement, who they are. And the decisions that they make today were profoundly impacted as a result of one or two things that their parents taught them about money. It’s hard to believe, but it’s true. You could retire anywhere. I say that tongue and cheek, but I mean, anywhere in the United States, but you’re just gonna stay in San Antonio. Right.


([19:59]): Well, that’s the plan. We, we just recently built a, a new house and moved in at right after labor day and pretty much our final house. Of course I always look at it. You can always sell whatever it is. I wanted to say top cell, my wife may have a different story, but families here grandkids are here. So this is where we’re at. And enough guys, always like whatever, but no, the, our wives gonna do they Do you just make sure you have a good golf courses around, right? Yeah. So now you playing Golf, right? I play, but Okay. You’re not like your


([20:33]): Son. No, he he’s good. I didn’t, I didn’t play in high school. And so I’m a hacker as he calls me, you know? Yeah. It’s funny though. When I used to Hey, to bring him, he was fine. Now he he’s doing well. He doesn’t even get me over to the country club. I know least buy me a drink. I


([20:49]): Know I’ll have to talk to him about that. What do you plan on doing for fun? So as you, you know, who knows, I don’t wanna, you know, announce your retirement from a company prematurely, but I think everyone knows, you know, you’ve gotta runway and you’re evaluating that. But when you decide to pull that trigger, what for fun? What is fun look like for you? What will you be doing? Woodworking, golf, hunting. What does that look like?


([21:12]): Kinda a little bit of everything. I I bought a ranch out in rock Springs. So I like hunting, not an hunter, but I it’s. It’s just fun to get out there. You still have cattle out there? No, I got rid of that. I didn’t mine ’em I kind of got attached, but I had a, a 25 in a mix of bulls and heifers and, and babies. But you know, you’re two hours away, two hard hour drive and they get out and then you gotta drop what you’re doing. And I mean, and at the time, and even now I’m traveling, I may be in Alabama and all of a sudden I’m getting a phone call, so it just became a pain. So I did the wildlife plan where we’re doing stuff to track wildlife to do that. So the you know, the Texas wildlife department, whatever they have a program and you can still get the ag accept.


([21:57]): Oh, very nice. Yeah. So we go out and and have a good time shoot some hog. Yeah. Turkey access and Whitetail. So, but it’s just so fun. Like get out there and it’s clear skin, unlike being in a city, you know, and got a lake house. So we go out and boat. So I kinda like doing all that, you know, so I got some things I can do where I won’t have to, all I have is hunting or something like that. And, but as for the, we like to travel and I’m hoping all the, this COVID and stuff goes away. Cause I’m not gonna get on a plane to, to Europe or wherever wear mask. Yeah. I’m not gonna do it. I just you and most Texans. Yeah, that’s right.


([22:38]): And we love history. We like doing that kind of stuff. And so I wanna be able to get onto that, but that’s pretty much it. And what about with grandkids? Is there anything that you wanna pour into their lives while they’re still aimable?


([22:52]): Yeah, well again, just taking them to the, to the ranch and, and to the lake. I mean, they’re getting an experience that I didn’t have when I was, yeah. Now we’re, we’re gonna try to get some, some trips somewhere, maybe take the family to Disney world or something or do a cruise. So where we can all do that as a, as a, and just get them to so we can spend time with them and, and we can do that without doing those trips, but I’m able to do that. So it’s something that it makes me happy. So is there anything you wanna teach them? You know, just good values. Yeah. Just good values and teach ’em right and wrong, you know, just be fair. And I like what my parents did and others, and I think that, you know, have being around, being around, they see, they see you.


([23:38]): Yeah. And they know, and it’s sad that, you know, some folks don’t have a, a full family and things happen, but I still believer of that’s how you do it. I mean, I, you see by example and learn by example. And I look at that, even my employees, I mean, they saw me coming into work early and whatever, and whether they felt guilty, they couldn’t leave while I’m there. I don’t know that happens. Yeah. But the bottom line is you see, and you have both the mom. And then I think that, that means a lot to your, as a young person, male or female, I mean, helps you grow up. And we’re all we’re teenagers. Right. So we all went through a stage like everybody else. I mean, my parents were the dumbest people ever do. I mean, you know, then you finally get my kids, you find out they’re pretty. We’re pretty good. Good. You know?


([24:26]): Yep. I know I’m with you. I’ve got two teenagers, so I get it. Yeah. Well, I do have as we close this out the most important question and that’s what’s your favorite salsa? Well, you know I like cooking, but I, I don’t make salsa, but to me, just the there’s a few restaurants in town make pretty good salsa. It’s like, it’s fresh. Yeah. But the roast it, the more, the hotter, I like hot stuff. Okay. Yeah. So I like the ones that there’s a couple of they that they it’s chunkier. Okay. Little bit more substance than like a liquid soup or something. It’s


([24:59]): Almost like a meal on the ship. Yeah, yeah, yeah. Yeah. It’s so but I I like eating, it shows well, we’re, you know, no one will know no one know. Huh. And but overall it’s just hot and spicy. It’s always been good


([25:13]): For me. Good. This has been good. I’ve really enjoyed it. Thank you so much, Chester. As we close this out, I just wanna remind everyone you’re listening to retire in Texas and visit PAC’s financial group on that website. We’re gonna have an ebook called retire in Texas. So you can grab that. There’s also a chance for you to click for 15 minute consultation with one of our advisors. There’s no obligation, no pressure. I just have conviction that the guides, the advisors here can help you with money. And I want to give you an easy way to access them. So you can click on that at PACS financial group dot, and then finally wanna remind you that you think different when you think.


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