Single Mom Turned Entrepreneur With Cheri Amstrong

If you’re a family business owner, you have the privilege to decide when to retire.

However, you may find it challenging to navigate family succession or understand your kids’ perspective on business.

So how do you bridge the generational gaps to set yourself up for a peaceful retirement?

Today’s guest is a single-mom turned entrepreneur, Cheri Amstrong. She’s here to show you how you can manage a thriving family business, set yourself up for an abundant retirement and build bridges between generations.

Listen now to discover how to understand our children’s generation better while building a family business that lets you retire at 58.

Show Highlights Include: 

  • Why sending your kids to work turns them into successful adults (even if you’ve got more than enough money to support them) ([3:52])
  • The Single Mom’s Guide to thriving in business (even in the midst of a Pandemic) ([9:33])
  • How understanding your kid’s generation makes you a better entrepreneur (and how to bridge the gap in 6 weeks) ([10:46])
  • How this simple advice could eliminate 80% of your child’s financial worries and lets you retire early ([16:40])


DLP027 PC - Single Mom Turned Entrepreneur with Cheri Amstrong



Do you want a wealthy retirement without worrying about money. 


Do you want a wealthy retirement without worrying about money. Do 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. 


([00:29]): Hey, this is Darryl Lyons and you’re listening to retire and Texas I’m the CEO and co-founder of PAX financial group. PAX financial group is the sponsor of this program. So be sure to visit PAXfinancial group.com. And remember, the information contained in this program is just for information only. It’s not intended to provide specific legal or tax advice, visit PAX financial group.com for more information. And if you need to speak with a financial advisor, be sure to simply text 7, 4, 8, 6, 8, and put in the word Texas, and you can speak to a financial advisor that way. Okay. So here we got a great show today. I’m excited and I think you will enjoy this one too. It’s a long time friend. And so I’m looking forward to visiting with Sherry Armstrong today. Sherry. Thanks for joining me. 


([01:09]): Thank you, Darryl.. I appreciate, uh, you asking me to be here, So what’s cool is I don’t know a lot about your background. I know some, but I don’t know where you grew up. Where did you grow up from? I grew up in Topeka, Kansas. I was born and raised there. Okay. And excuse my ignorance, but Topeka, is this a tornado alley? Uh, yes it is. It’s the capital of Kansas. And, um, I was born many years ago. <laugh> you don’t have to tell me your age. No one needs to know. I could. Good. I’m not ashamed of it actually. I’m embracing my age. Yes. Good. And so you were born in Topeka, Kansas, which I do know that now that you mentioned is the capital, but when you grew up there, were there tornadoes? Oh, there were. Yeah. Did you ever see one? Yes, we did. Yes. Because I don’t know. It’s kind of a weird thing for me. Like it’s a bucket list for me to see a tornado. And I always tell my wife that it’s, you know, obviously I don’t wanna be in harm’s way, but they’re fascinating. So you got a chance to see when I have to hear about this. I did. When I was young, I was the oldest of 10 growing up. I was the oldest Of 10. 


([02:07]): Yes. My parents took in foster kids and I had three biological siblings, two adopted. And, uh, we had a total of five foster children every day in our home, since I was in the third grade. Are you serious? Yes. My parents had a heart to, uh, help kids that were less fortunate than ourselves. And, and so from third grade on, I had a baby on my hip. No way I had no idea. So what did your parents do? Well, my dad was a pipefitter for Goodyear and, uh, my mom was a stay at home mom and, uh, she did lots of things. She loved to bowl and, uh, that was her outlet, but mainly it was, uh, taking care of kids and, um, uh, working in the community. I took Baton lessons when I was young and, um, dance lessons. So she’d make my uniforms and uh, then she’d make everyone else’s uniforms in the team so she could help pay for that uniform. So, but about the tornado, there was a day in which we heard our dad calling and, uh, so we all came running home and he told us to get to the basement. And so we all headed down there and he kept hollering from my mom, you know, Bev, come look, come look. And we all ran upstairs because we heard him calling for mom and we’re looking at the front porch and we’re looking out the window and the smell of the air. It was so still, and it had a specific smell and, uh, the atmosphere seemed sort of greenish colored. Huh. And so that’s what I remember. And so, uh, it was a big, I think it was in 1969, June of 1969. Wow. It was a horrific tornado that had hit Topeka, but everyone was okay. 


([03:51]): Yes. Our family was great. Growing up is a pipefitter that was considered middle class income in that area. It was, yes mm-hmm <affirmative>. Yeah. And so did they ever teach you about money or did you just observe things about money? I never really learned much about money until I was about 12 years old Uhhuh. You know, we took everything from the farm milk, eggs. Uh, we raised rabbits, we had a garden, but at the age of 12, my, um, dad came to me and he told me that I was gonna have to find a job at 12. At 12. Yes. I couldn’t wrap my head around that. Yeah. And because we had so many children in our home and, um, he would work extra overtime, you know, to pay for my tap dancing lessons and my Baton lessons. And, and so he said, uh, you’re 12 now. So you’re gonna have to get yourself a job. You’re gonna have to start paying for your Baton lessons and helping your mother with your costumes. And, um, I told him, daddy, I have no idea what to do about a job. And he goes, you’ll figure it out. So I went and got a piece of construction paper and, uh, wrote on there with my crayon Baton lessons, with my phone number. And I walked it up to the elementary school and taped it up on the wall in the cafeteria. And a couple weeks later, my parents had received some phone calls and I had five girls that were in kindergarten that I was teaching them figure eights and pinwheels. And, uh, my dad was really proud of me. 


([05:14]): No kidding. That is really, really encouraging. So that was my first job. And I’ve been working ever since, you know, it’s so cool because for me, this is where I just overthink things. Like I, I would’ve probably leaned in to try to help and try to come up with a strategy. But just the brilliance of saying, you’ll figure it out is really, we need more of that. Like just figure it out. You know, you’ve got a brain so use it. And I think that’s, there’s something to be said for that. And so I wanna come back to that story cause I think that’s an important story. Were there any low points in that experience with the 10 kids and did they ever have to go to a place where financially it was just really, really difficult and you remember that? Well, my parents were foster parents of the year when I was a senior in high school. And, um, it had really taken care of all those kids and had really been taxing on my parents, I imagine. And so they ended up getting a divorce. Oh. So unfortunately the kids had to go back into the system and uh, I had moved on to college, but that was devastating to see because we’d always worked hard to help one another and, and seeing those kids leave was, you know, not something that you ever thought would happen, especially as a child. 


([06:22]): Oh, that is devastating. And, um, foster parents of the year. What does that mean? Is that a national thing or it was a national thing. Yes. Yeah. And my mom was really the person who had the desire to foster and take care of foster children. And my dad agreed to do that. You know, even after that, my mom continued throughout her whole life wanting to mentor kids and invest in them and, and really make a difference in the community with kids. So, wow. What a sweet lady. Okay. So let’s jump way ahead here. So are you officially retired? I am not officially retired. I am pivoting. Okay. Great answer. And so in January I decided that I was going to, I had a little bit more time on my hands because, um, our son was running our business. And so it was back when COVID had hit. I had helped a little bit, but back in may of last year, I decided that it was time for me to step back, especially with COVID and mm-hmm, <affirmative> the difficulty in finding employees and stuff like that. And the revenues. Can you tell the audience about what kind of business that you had? The name of our company is Mecca sportswear. We sell letter jackets in the high schools. Okay. And, um, we make monumental moments in kids’ lives every day. Oh, I love it. Love it. So we love, we love doing that. So, and so you, how long have you had this business? I was a single mom. I started it in 1983. Wow. My first husband had left and, um, we had moved down here from Kansas with a job for him. And after a few years, after being married seven years, we had some problems. So he chose to leave. And instead of, um, going home back to Kansas where I could work for the state, cuz most of my family did or stood in a welfare line. I decided I needed to figure it out. 


([08:08]): You had how many kids at the time? I had two, I had a daughter that was five and a son. That was three. How scary is that? It was, gosh, it was gosh, very scary. Oh my gosh. You’ve got that bravery that your mom had. Well, I do know that when I look back on it, I remember thinking about when I was 12 years old when I had my first job. Yeah. So I’m gonna figure it out. Yeah. That’s It’ll work. That’s right. I can definitely connect those dots. And so you started this business and did you just write on like with crayons, do you need a Letterman jacket and post it up? How did you start it out? No, actually I was working at a trophy shop when I was first divorced and I went to the gentleman that I was working for and I asked him if he would contact two men that I knew that had previously hired my husband because they had told me at one time, if I ever needed any help to, uh, give them a call, you know, people say things just in passing and uh, really they’re divine appointments, you know, because you never know what’s ahead. And so I’m thankful for those small markers in my life where I can look back and say, okay, there we go. So I ask Max to please call them. And he wasn’t sure that they would, but they came down and, um, it was like Dorothy from the wizard of Oz. Yeah. Meeting two men from the movie men in black, there was that much of a contrast. Okay. I was in my Penif four and jumper and sandals and they were in two or there are three piece suits. 


([09:33]): Oh my gosh. You know, the thing I think about bravery is not the lack of fear, it’s pushing through that fear. And that’s what’s right. Probably was, was the situation for you. And so running this business as a single mom, there’s so much to talk about that we can’t cover, but I want to come back to this pivoting part COVID happened, obviously, you know, there were all kinds of disruptions in supply chains and cash flow. And did that influence your desire to start transitioning out to your son? It did. My husband had retired when he was 58 back in 2013. And uh, Billy, our son, uh, was going to Baylor at the time and knowing that I couldn’t do this by myself, I asked him if he would come in and join us and he was very happy to come join us, but he wanted to make a few changes, get the business out of the home, you know, run it a little bit differently. And so he did that. And then when COVID hit, we lost about 75% of our business. And so to make sure that the revenues that we had covered his salary, his compensation, they were expecting a baby in July. Yeah. And so, um, he moved the office back to the home and I helped him process orders, but he started taking orders on zoom. So that’s interesting. So the age gap there was there tension because it sounds like he had a degree of maybe some ambition. Yes. And then also some, um, affinity for embracing some new tools and technology. Yes. Did you push back on that? Did you embrace it as well? How was that? 


([11:03]): Well, when he joined us, when he came in, I knew that we had a baby boomer mentality and a millennial mentality. Yeah. And there was a gap in between there. So I, uh, reached out to, uh, Dr. Kowski, I think I’m pronouncing his name right from, uh, Texas state Uhhuh <affirmative> he came in and we met with him for about six weeks to bridge the gap between the baby boomer and the millennial really interesting. And um, I wanted to be able to hear what Billy was saying and I wanted him to hear what I was saying. And so, uh, I think that was a good process and a good work for us. What an investment that’s, there’s some foresight there, because the way I think about business is you don’t rise to the occasion. You fall to the level of your training. And so when you do have those bumpy roads, then you’re able to fall back on that training that you guys had. Is that true? Am I expressing that correctly? So for those that have just tuned in we’re with Sherry Armstrong, an entrepreneur, a success story, transitioning and pivoting into the next chapter of life. And for those that do need a quick, no obligation, complimentary consultation with one of our financial advisors, just go to your cell phone and type in seven, four, eight, six, eight input and 7 48 68 and put in Texas and we’ll connect you. So Sherry, you haven’t officially retired. 


([12:17]): That is correct. I still do PR work for the business. Okay. I was at school yesterday. Okay. And, um, my husband and I last week, Billy needed some help at another school. So we went out there with him the way he processes orders. Now he’s taken in, brought in some new systems. Okay. Where we used to do everything by hand. Yeah. Okay. And four part copies and things like that years ago, he has taken advantage of his knowledge in technology and brought the business up to speed. So yeah. Very close. We’re very proud of them. Are you working with public or private schools or both? We work with both. Okay. Good. And so when I remember, you know, when I was in high school, many decades ago, the quality of the Letterman jackets weren’t that good. They’ve changed over the years, the product. And, I’ve noticed that there’s been a lot of changes. What do you see in the next chapter of, of the products that y’all are offering, are you gonna have resources from overseas or what are people expecting from y’all now going forward? 


([13:15]): Well, we have a lot of competition from overseas. Our company is located in Toma, Wisconsin. Okay. So our products are made in the USA. And so therefore the quality is much better. And what we’re seeing is that kids are taking a lot of pride in the jackets that they wear, especially if they’ve earned them. So they are adding all of their trophies, if you will, like their all district patches and their championship patches and those things that they’ve done throughout their school year. And, um, it really is an exciting time, especially when you see parents come in with their kids and the parents are just telling their kids how proud they are of them that they’ve accomplished this and Darrell. I remember before I forget this, I remember, um, raising, we had four kids and, um, our two youngest were 14 months apart. And so I would call my dad and say, man, I just can’t believe how expensive kids are nowadays. And he said, um, darling, let me tell you something as a parent, you’re either gonna pay for success or you’re gonna pay for failure, but either way you’re gonna pay. Yep. So you take joy in paying for those boys’ things, whatever it is they want, because it could be the opposite. 


([14:26]): Mm that’s really good. So that was real good advice from the dad. That’s real good advice. And now we’re seeing people take a lot of pride in paying for these skills, these kids get, and then they’re honored with the jacket that you produce. Yes, that’s right. And I’m very thankful that you’re maintaining your production in the United States. Yes. So you should feel good about that. I’m very proud of that. In fact, if there was a manufacturer in Texas, uh, I would be using them right now. <laugh> In fact, I’d love to have our company move to Texas. That’d be great. I’m hoping somebody from the economic development, council’s listening to this right now. So now as you’re kind of pivoting and, and you’re alluded to going back and helping where you can with Billy, what does the next chapter look like for you? What would you be doing? I mean, certainly grand babies. Yes. We have 11, 11 grand babies. 11, no idea. Grand babies. Yes. We had five girls and five boys and the girls were so excited that, uh, the older girls were excited and wanting a girl and the older boys were winning a boy Uhhuh. And so we had our little tiebreaker, I call her, her name is Ruth. Oh, beautiful name. She’s precious. 


([15:28]): So, and so I don’t wanna put words in your mouth, but would the next chapter be time with grandkids helping out with the business? Anything else traveling? What are you thinking? Well, Bill and I love to travel, mainly he, uh, rides a motorcycle. Okay. And so he has a Honda gold wing and he takes me on that with him. And so we do some traveling and then also, um, I’ve been in January, I chose two words impact and inspire for this year. Wonderful. And so I’ve been investing in myself and um, finding out how I can do that. And I’ve been studying, uh, God’s word about purposeful women in the Bible. Wonderful. And I feel like that’s a great opportunity for moving that direction where I can help small business women working moms and show them that they are purposeful women. Oh my gosh. Well, with your story, that alone gives me goosebumps. So I’m getting goosebumps hearing about that opportunity for you and the idea for me when somebody’s pivoting to this next chapter and they have resources and they have time and they have breath in their lungs, God still has a purpose. Absolutely. Yes. 


([16:28]): And so to see you use that purpose and lean into it’s exciting, is there a tricky money decision that you find yourself having to make right now, or obviously the markets are what they are, right. The markets are what they are. However, um, my husband is, um, a good steward of the finances that, um, we’ve had over the years. And so we made a lot of sacrifices when we were young, so that when we got older, our children wouldn’t have to take care of us. Mm. And so he said no to me a lot, when I was younger, when we were making money and I’d say, oh, I made some extra money. You know, let’s buy this and let’s buy that. And he would say, no, we’re not gonna do that. We’re gonna save it for our future and someday we’ll need it. And so, uh, that’s why he was able to retire at such a young age. And yeah, we’ve made some investments in commercial property. Okay. And therefore we have passive income coming in. Very, very nice, I feel comfortable about not working. And, um, I love what I’m doing. And, uh, looking forward to what the future holds and, and traveling and loving on my grand babies and watching my children grow, they’re all four very successful. And I’m very grateful to God for them. What a blessing. So Texas is home. No need to go back to Kansas. 


([17:36]): Absolutely. Texas is Home. Good. Well, I’m glad that you’re here. And, and I look forward to hearing about this next chapter and, and what you can do. And gosh, there’s so many working single moms that I know that are just I’m rooting for ’em. And I know that absolutely. I’m glad that there’s people like you out there that can encourage them. And, but not only just encouragement because it’s also some tactical things about how to run a business, how to negotiate. There’s all those skill sets that you have that you’ll be able to give back. And so, well, I hope so. I’d love helping young women and I love helping women start businesses. When are you gonna write your book? That’s a good question. I do have a name for it though. Okay. It’s the mile markers on my journey. Oh, the mile markers on your journey or my journey on my journey. I love it. Okay. The mile markers on my journey. Okay. And in every chapter it will speak of a mom marker. As I’m looking in my rear view mirror, it’s gonna be when God last showed up. So I don’t have to worry or Fret about what’s ahead. Cuz he’s gonna show up there too. Oh my goodness. That’s beautiful. I absolutely love that. Like I said, there’s a lot to unpack here because what I did is I talked about the very early part of life and then this pivoting and then there’s this whole journey in between that we weren’t able to cover, but I really appreciate you sitting down and sharing that with me. And, and it’s so cool to see how even your father and his, Hey, go, just figure it out, translated into really a whole career. 


([19:02]): Yes, absolutely. And you know, we’re told every day things that we don’t wanna hear, but the truth of the matter is God allows those things to be spoken to us. Mm-hmm <affirmative> to get us and prepare us for what’s ahead in our journey. Mm, that’s a really good word. Okay. Now the last question. Most important question. What’s your favorite salsa? My favorite salsa. I’m so glad you asked, because I’ve been wanting to say this for a long time. It’s doms, Doms, doms, salsa. Where do I dominate Mendiola? Okay. I met him a few years back in the shirts, bank and trust, and he was applying for a loan to start his business. And, uh, it is the best salsa out there. Okay. And where do I get it? And you can find it at HEB and uh, if you look it up, dominate Mendiola. Okay. Dom salsa. You can find out about it. Okay. But if you’re listening, Don, thank you so much for doing an awesome job. Okay. We’ll have to get him on the show. Yeah, that’s great. So, Hey, this has been great. I really appreciate you coming on and sharing your story. There’s so much there. I’m gonna have to have you back on and thank you as I get listener feedback, which I, as I get listeners, I wanna encourage you to email me Darrell psg.com about this show. And I’ll have guests back that you wanna unpack some parts of their lives. So hopefully we can have you back. So thank you. 


([20:17]): Thank you so much St for having me. All right. Y’all are listening to retire in Texas Darryl Lyons. And I just wanna remind everyone to, don’t forget, you can just simply text 7 48 68 and put in Texas and you can have that consultation with the financial advisor doesn’t cost you anything, but most importantly, as you go out there and battle through business life and investments in retirement, all those big questions. I just want to remind you that you think differently when you think long term have a great day. 


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