Brokers, Burnout, and the Quiet Work of Becoming a Free Agent: A Founder’s Real Exit Story
What if the smartest move in preparing your business to sell wasn’t a polished pitch deck or a perfectly timed market window—but something quietly overlooked, like methodically removing yourself from the very company you spent years building? In this conversation, a founder who recently sold her marketing agency walks through the offer she turned down, the broker decision that nearly doubled her valuation, and the year of unglamorous, behind-the-scenes work that made her business genuinely sellable. Oh, and you’ll never guess how a part-time consulting role she almost said yes to in a moment of burnout ended up becoming the bridge to her next chapter… Curious what an exit really looks like from the inside? Stay with us, because most of what she shares is the part founders rarely talk about out loud.
My special guest is Catherine Wilson
Catherine Wilson built her career around the kind of problem most founders dream of having—figuring out how to keep up with customers who wouldn’t stop calling. She grew her own home services marketing agency into a remote-first team that spanned multiple countries, all while raising four boys in Wisconsin and supporting her husband through a string of major surgeries. Catherine’s story isn’t the usual founder narrative of chasing clients; demand was the easy part. The hard part was building an operation strong enough to absorb that growth without her sitting in the middle of every decision. Along the way, she learned how to hand off sales, lean on a sharp director of operations, and recognize the moment when her own role had quietly become smaller than her business. That clarity carried her through a roughly year-long preparation, two very different paths to a buyer, and a clean close at the end of January. Now stepping into a hybrid marketing role on the corporate side, Catherine brings a candid, hard-won perspective on what it actually takes to make a business worth buying—and what the founder pays to get it there.
“I knew to make the company as valuable as possible in a sale, I had to make sure I was out of as many things as possible.”
In this episode, you will be able to:
- Discover what genuinely makes a business sellable—and the year of quiet, behind-the-scenes work that goes into it long before any buyer enters the picture.
- Build the kind of operational backbone that lets you step away from sales, fulfillment, and daily firefighting without your company missing a beat.
- Compare the realities of fielding a direct buyer offer versus partnering with a business broker, and understand which path tends to protect your valuation and your terms.
- Recognize the hidden weight of running a company that lives in your head twenty-four hours a day, and use that lesson to design a healthier next chapter for yourself and your family.
- Plan a thoughtful re-entry into corporate or hybrid work through consulting first, so you can test culture, fit, and pace before signing on full time.
Preparing a Business That Is Actually Worth Selling
The most valuable companies are not the ones running on a single founder’s energy—they are the ones that can keep moving when the founder steps out of the room. Building a sellable business means deliberately pulling yourself out of the work over time, putting strong operators in the right seats, and replacing your own instincts with documented systems and capable leaders. It also means resisting the temptation to accept the first offer that lands in your inbox; serious buyers respect a seller who knows exactly what the company is worth and has the right advisors—typically a broker and an experienced attorney—standing behind that number.
The resources mentioned in this episode are:
- Listen to the Free Agent Podcast on Spotify and all major podcast platforms.
- Share and promote this episode with your network when it is released.
- Learn more about CMIT Solutions franchise opportunities at cmitsolutions.com — a proven model for IT-focused entrepreneurs.
- Explore Rotary International and consider how community service through Rotary might complement your own journey as a business owner.
- Connect with Meg Schmitz and FranChoice to explore whether franchise ownership is the right next chapter for your own story.
- Listen to the Free Agent Podcast with Meg Schmitz for real stories of self-employment and business ownership.
- Contact Meg Schmitz to schedule a free, no-obligation call for insights into entrepreneurship and franchise opportunities.
- Use the form on the Free Agent Podcast page if you’d like to be considered as a guest on the show.
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Click to Take the Leap into the full interview transcript of the Free Agent Podcast, Episode 8.15 with Meg Schmitz and her guest, Catherine Wilson
Free Agent Podcast with Meg Schmitz – Guest: Catherine Wilson, Home Services Marketing Agency Founder & Business Exit Strategist
Catherine Wilson: Mostly. Stuff from the background of my plate.
Meg Schmitz: Yeah. So… so… okay, start… start at the beginning with who is… who approached you, or did… were you looking to sell? What…
Catherine: Yeah, so…
Meg: Paint a picture.
Catherine: So, it started off… so, okay, the first thing is, like, my goal was always to someday sell the business. Like, I knew that that was… that was gonna happen someday. And I had met with a broker about a year before, and we just weren’t at the spot. Like, I knew to make the company as valuable as possible in a sale, I had to make sure I was out of as many things as possible.
Meg: Yeah.
Catherine: And I just wasn’t quite there yet. And we had been going through some transition in the company, like, a year before, and some, you know, a lot of change, and so I knew it wasn’t the right time then.
Meg: That was crazy.
Catherine: I was gonna say, I don’t know if it was you or me.
Meg: We have been having terrible internet issues here, and we’re about to switch our provider and get a business account with 5G and, I don’t know, a bazillion gigabytes of whatever. So, sorry about that. I’m sure that was on our end. Okay, so, begin at the beginning, and hopefully it won’t cut out again.
Catherine: Alright, no worries. Yeah, so I knew that I always wanted… the goal was to always sell, and so I was basically, it took the next year to figure out, like, who I needed to get in place, like, what that process was, and to kind of get as many things in place as possible. And then, honestly, I didn’t think I was quite ready, but then I was approached by someone else, and so the agency focused on home services, and the person that approached me was someone who was looking to buy agencies that focus on home services.
Meg: Great.
Catherine: So, I was like, well, let’s just… let’s talk. I actually even told him, I’m like, I don’t think I’m quite ready to sell yet, like, I don’t think I’m big enough for you to want to buy, and he’s like, well, let’s just, you know… he was like, well, let’s just at least talk, and then maybe if it’s not the right time, you know, there’ll be a right time in the future. And so, long story short, we had a really good conversation, and he was like, you absolutely have a sellable agency, like, I’d like to give you an offer. And so, I went through that process with him, and the offer just really wasn’t… I mean, it was an offer, it was something to consider, but then I wanted… I was kind of interested. I’m like, well, I’m gonna go back to this broker and at least see, like, if I have a sellable business here, you know, maybe they… I’m curious what they say. Started working with a broker. They came back with, like, a valuation that was much higher than what the other person had said, as well as much better terms, and, you know, having somebody advocate for me, and things like that. So, I signed with them, and within… I think it was, like, 2 months of the initial conversation, we had narrowed it down, they brought different buyers, we kind of had conversations, and ended up going with somebody they brought to the table. That took about 6 months.
Meg: I’m so excited for you!
Catherine: Yeah, it was really… actually, I was gonna say it was really fun. It was very stressful still, but, like, it was… it was an experience, and we closed the end of January.
Meg: And so, will you be staying on for a period of time? Did they kind of buy you out with an add-on period for consulting?
Catherine: Yeah, so technically, I agreed to work with them for the next year, but we’re already transitioning way ahead, because I was able to get… the biggest thing that I was still doing was sales, and they had somebody that could come in and do sales, which was the piece that I was really struggling with, and so, I had a director of operations, she was overseeing all the fulfillment and everything like that, so they’re really… once they got the sales piece down, they really don’t need me. Ideally, I’m actually gonna be, like, fully transitioned out probably by the end of the month here.
Meg: Good for you! What a journey. Since the day we met at the Young Guns event, to where you are now… it’s been a long time since I’ve sold a business, and I haven’t sold an independent business for a while. Pete, my husband, gets offers quite often, and what would you recommend process-wise, for me, or for us, if we were going to consider selling our company, Tallgrass?
Catherine: I mean, I only have my experience. I really liked working with a broker, just because… I had never done… I mean, with Alex’s company, we technically sold it, but it was such a different experience. I really liked having a broker that I could go to. I usually have a million questions, I want to understand what’s going on, and so they were really, really helpful. I really like… I’m not a negotiator, and so they handled all of that stuff, they were able to back up the valuation and everything like that. I really appreciated their help. And then the other piece is, since we had gone through this before, I knew I wanted to have a really good lawyer in the mix. I think that was the other piece — those two people are the ones I leaned on the most. The broker and then my attorney really helped, especially as we were closing. I think we talked multiple times a day, just making sure everything was right and we were set up.
Meg: How did you meet the lawyer?
Catherine: Actually, through Young Guns. Yeah — who was it? Dino? I’m gonna say that wrong, I know I’m going to, but that’s who we ended up working with on this one. We met him through Young Guns — actually, probably at the same time I met you, to be totally honest. It might have been at the same Young Guns event. So, they need to bring those back.
Meg: That was such a great group, and I know that Andy and David aren’t going to do it. I was just thinking about them recently. Being one of the first in — I was one of the first, and that’s what reminded me — I was on a panel discussion last week in Chicago for the Northern Illinois Franchise Association. It took them 13 years to invite me to a panel discussion. I was one of the founding members of that one, and then I was on the advisory committee for Young Guns, and it just got to be a lot of time and effort with diminishing returns for them.
Catherine: Makes sense.
Meg: But the events were always inspiring, insightful, educational — the contributions of the other members. It was such a strong group, but anyway…
Catherine: It has to be worth it. I’m sure it was an insane amount of time.
Meg: So, for you — have you started a job yet, the one you mentioned?
Catherine: So, I have a couple things going on. I was actually offered a job about a year ago by this company — well, over a year ago now — and I almost took it. Okay, so when we met at Young Guns, my stress level was really high, and I think that’s how we met — I like went up and Andy had convinced me to go in front of everybody and talk about my stress, which was… looking back, I still, to this day, I’m like, I don’t know how I thought I was stressed out, because it just kept getting more and more. As I was growing the agency, it was just more and more stress. So about a year and a half ago, after I met with the broker and we agreed we weren’t quite ready, I was like, alright, let’s figure this out. By December, I was like, I’m done. I am so done. I’m just gonna shut it all down. The stress was huge — Alex was going to have the first of, like, 4 major surgeries, and I was like, I can’t do everything. I can’t handle all this. So I actually interviewed for a job, because I was like, maybe that will be the answer to my stress and our family situation. And they offered me a job, and I almost took it. I almost just shut everything down. But I kind of went back and forth, and I was like, I’m just not ready. I’m not ready to just shut it down. I know there’s something here. And I’m really glad, obviously, that I didn’t. Even with Alex’s surgery, the business gave me more flexibility with company. Then, in February or March of last year, they were still trying to fill that position, and so I reached out to them and said, would you consider me working in a consultant role?
Just looking for a way to have some security and options. So I took a part-time consulting role with them, and I’ve been doing that up until now. And it was really awesome because it gave me the chance to see, like, what would it be like to go work for a company again? Because I was terrified to go back to working for somebody. But it’s been awesome. The company is so good. They’re in the manufacturing space, which I love. They knew I was going to be selling the company, so they were incredibly supportive through the whole process, and then I took a full-time role with them in the marketing side of things.
Meg: And so, family impact — is this giving you more…? Your boys are getting older now, they’re not as young as they were when we met, whatever that was, 5 years ago. You’ve got a busy household, and then Alex — is he still running a business?
Catherine: No, he actually has more surgeries lined up. He’s getting his knee replaced again at the end of April, and then he’s having issues with his hip, which they had just replaced. His focus right now — luckily, he’s able to help with the kids, he does a lot of the driving and is able to do that, but yeah, he’s just focusing on trying to heal and get back to normal.
Meg: Interesting how the world turns, and roles and responsibilities shift. So that’s great. In going back to work — you really nailed it with the part-time consulting role. It gave you every opportunity to look in the nooks and crannies for issues and problems, lack of trust, poor culture… you had time to really evaluate whether this was going to be a good full-time move.
Catherine: Yeah, no, I’m really excited. The company is amazing, their culture is awesome, they’re growing. So yes, it was a really good opportunity for me to make sure I felt comfortable transitioning to a full-time role again with the company. A couple years ago, I probably wouldn’t have been able to do it, but…
Meg: And is it virtual or hybrid?
Catherine: It’s hybrid, so I’ll go into the office a little bit, which is honestly really nice. I’ve been working from home for 10 years, and so it’s kind of nice to be around people and actually interact with people — people who aren’t just there for my kids’ basketball games.
Meg: Adult stimulation! With your agency, was everyone else virtual, or was there an office?
Catherine: Nope, we had an office for a short while, but no, everyone was remote. Only one other person was here in Wisconsin, even, and she was about an hour and a half away. So we would get together every once in a while, which was nice, but yeah, everyone was actually all around the world.
Meg: Wow. Yeah, I’m absolutely delighted for you. How is Alex in all these transitions? You two have always had a really dynamic, interesting marriage.
Catherine: We have. Yeah, I think the biggest thing is my stress level is so much less now. And so I think that’s been really helpful for us. I’m more available. I mean, I love to work — I’m a workaholic 100% — but I’ve been able to, by 5 o’clock or so, leave my computer, walk away. We joined a gym, we’re going to the gym as a family. So I think that’s been really good.
Meg: There are some hidden elements of owning your own business — and this is why, Catherine, when I’m working with people I say, you know, it’s going to live in here 24/7. You may be done 8 to 5, but it’s gonna live in here all the time. That’s one of the hidden stressors for people — it just never really does shut off. Pete and I have how many companies, and he woke up this morning and said, I feel like we’re busier than ever. So that is something a big benefit. So, how old are your boys now For a big benefit that you are more available
Catherine: Connor is 16, which is amazing — he has his license, and he’s a good driver, so I feel pretty safe with him driving around, and that has been amazing. So we have 16, then we have a 13-year-old, and then 9 and 7 and a half. The half is very important to him.
Meg: I forgot about how much younger the two little ones are.
Catherine: Yeah, we have the two older and then kind of two younger. And they have basketball now — I think 4 days a week starting in April, so we have a lot going on.
Meg: Well, I’m delighted.
Free Agent Podcast with Meg Schmitz – Guest: Catherine Wilson, Home Services Marketing Agency Founder & Business Exit Strategist
Catherine Wilson: Mostly. Stuff from the background of my plate.
Meg Schmitz: Yeah. So… so… okay, start… start at the beginning with who is… who approached you, or did… were you looking to sell? What…
Catherine: Yeah, so…
Meg: Paint a picture.
Catherine: So, it started off… so, okay, the first thing is, like, my goal was always to someday sell the business. Like, I knew that that was… that was gonna happen someday. And I had met with a broker about a year before, and we just weren’t at the spot. Like, I knew to make the company as valuable as possible in a sale, I had to make sure I was out of as many things as possible.
Meg: Yeah.
Catherine: And I just wasn’t quite there yet. And we had been going through some transition in the company, like, a year before, and some, you know, a lot of change, and so I knew it wasn’t the right time then.
Meg: That was crazy.
Catherine: I was gonna say, I don’t know if it was you or me.
Meg: We have been having terrible internet issues here, and we’re about to switch our provider and get a business account with 5G and, I don’t know, a bazillion gigabytes of whatever. So, sorry about that. I’m sure that was on our end. Okay, so, begin at the beginning, and hopefully it won’t cut out again.
Catherine: Alright, no worries. Yeah, so I knew that I always wanted… the goal was to always sell, and so I was basically, it took the next year to figure out, like, who I needed to get in place, like, what that process was, and to kind of get as many things in place as possible. And then, honestly, I didn’t think I was quite ready, but then I was approached by someone else, and so the agency focused on home services, and the person that approached me was someone who was looking to buy agencies that focus on home services.
Meg: Great.
Catherine: So, I was like, well, let’s just… let’s talk. I actually even told him, I’m like, I don’t think I’m quite ready to sell yet, like, I don’t think I’m big enough for you to want to buy, and he’s like, well, let’s just, you know… he was like, well, let’s just at least talk, and then maybe if it’s not the right time, you know, there’ll be a right time in the future. And so, long story short, we had a really good conversation, and he was like, you absolutely have a sellable agency, like, I’d like to give you an offer. And so, I went through that process with him, and the offer just really wasn’t… I mean, it was an offer, it was something to consider, but then I wanted… I was kind of interested. I’m like, well, I’m gonna go back to this broker and at least see, like, if I have a sellable business here, you know, maybe they… I’m curious what they say. Started working with a broker. They came back with, like, a valuation that was much higher than what the other person had said, as well as much better terms, and, you know, having somebody advocate for me, and things like that. So, I signed with them, and within… I think it was, like, 2 months of the initial conversation, we had narrowed it down, they brought different buyers, we kind of had conversations, and ended up going with somebody they brought to the table. That took about 6 months.
Meg: I’m so excited for you!
Catherine: Yeah, it was really… actually, I was gonna say it was really fun. It was very stressful still, but, like, it was… it was an experience, and we closed the end of January.
Meg: And so, will you be staying on for a period of time? Did they kind of buy you out with an add-on period for consulting?
Catherine: Yeah, so technically, I agreed to work with them for the next year, but we’re already transitioning way ahead, because I was able to get… the biggest thing that I was still doing was sales, and they had somebody that could come in and do sales, which was the piece that I was really struggling with, and so, I had a director of operations, she was overseeing all the fulfillment and everything like that, so they’re really… once they got the sales piece down, they really don’t need me. Ideally, I’m actually gonna be, like, fully transitioned out probably by the end of the month here.
Meg: Good for you! What a journey. Since the day we met at the Young Guns event, to where you are now… it’s been a long time since I’ve sold a business, and I haven’t sold an independent business for a while. Pete, my husband, gets offers quite often, and what would you recommend process-wise, for me, or for us, if we were going to consider selling our company, Tallgrass?
Catherine: I mean, I only have my experience. I really liked working with a broker, just because… I had never done… I mean, with Alex’s company, we technically sold it, but it was such a different experience. I really liked having a broker that I could go to. I usually have a million questions, I want to understand what’s going on, and so they were really, really helpful. I really like… I’m not a negotiator, and so they handled all of that stuff, they were able to back up the valuation and everything like that. I really appreciated their help. And then the other piece is, since we had gone through this before, I knew I wanted to have a really good lawyer in the mix. I think that was the other piece — those two people are the ones I leaned on the most. The broker and then my attorney really helped, especially as we were closing. I think we talked multiple times a day, just making sure everything was right and we were set up.
Meg: How did you meet the lawyer?
Catherine: Actually, through Young Guns. Yeah — who was it? Dino? I’m gonna say that wrong, I know I’m going to, but that’s who we ended up working with on this one. We met him through Young Guns — actually, probably at the same time I met you, to be totally honest. It might have been at the same Young Guns event. So, they need to bring those back.
Meg: That was such a great group, and I know that Andy and David aren’t going to do it. I was just thinking about them recently. Being one of the first in — I was one of the first, and that’s what reminded me — I was on a panel discussion last week in Chicago for the Northern Illinois Franchise Association. It took them 13 years to invite me to a panel discussion. I was one of the founding members of that one, and then I was on the advisory committee for Young Guns, and it just got to be a lot of time and effort with diminishing returns for them.
Catherine: Makes sense.
Meg: But the events were always inspiring, insightful, educational — the contributions of the other members. It was such a strong group, but anyway…
Catherine: It has to be worth it. I’m sure it was an insane amount of time.
Meg: So, for you — have you started a job yet, the one you mentioned?
Catherine: So, I have a couple things going on. I was actually offered a job about a year ago by this company — well, over a year ago now — and I almost took it. Okay, so when we met at Young Guns, my stress level was really high, and I think that’s how we met — I like went up and Andy had convinced me to go in front of everybody and talk about my stress, which was… looking back, I still, to this day, I’m like, I don’t know how I thought I was stressed out, because it just kept getting more and more. As I was growing the agency, it was just more and more stress. So about a year and a half ago, after I met with the broker and we agreed we weren’t quite ready, I was like, alright, let’s figure this out. By December, I was like, I’m done. I am so done. I’m just gonna shut it all down. The stress was huge — Alex was going to have the first of, like, 4 major surgeries, and I was like, I can’t do everything. I can’t handle all this. So I actually interviewed for a job, because I was like, maybe that will be the answer to my stress and our family situation. And they offered me a job, and I almost took it. I almost just shut everything down. But I kind of went back and forth, and I was like, I’m just not ready. I’m not ready to just shut it down. I know there’s something here. And I’m really glad, obviously, that I didn’t. Even with Alex’s surgery, the business gave me more flexibility with company. Then, in February or March of last year, they were still trying to fill that position, and so I reached out to them and said, would you consider me working in a consultant role?
Just looking for a way to have some security and options. So I took a part-time consulting role with them, and I’ve been doing that up until now. And it was really awesome because it gave me the chance to see, like, what would it be like to go work for a company again? Because I was terrified to go back to working for somebody. But it’s been awesome. The company is so good. They’re in the manufacturing space, which I love. They knew I was going to be selling the company, so they were incredibly supportive through the whole process, and then I took a full-time role with them in the marketing side of things.
Meg: And so, family impact — is this giving you more…? Your boys are getting older now, they’re not as young as they were when we met, whatever that was, 5 years ago. You’ve got a busy household, and then Alex — is he still running a business?
Catherine: No, he actually has more surgeries lined up. He’s getting his knee replaced again at the end of April, and then he’s having issues with his hip, which they had just replaced. His focus right now — luckily, he’s able to help with the kids, he does a lot of the driving and is able to do that, but yeah, he’s just focusing on trying to heal and get back to normal.
Meg: Interesting how the world turns, and roles and responsibilities shift. So that’s great. In going back to work — you really nailed it with the part-time consulting role. It gave you every opportunity to look in the nooks and crannies for issues and problems, lack of trust, poor culture… you had time to really evaluate whether this was going to be a good full-time move.
Catherine: Yeah, no, I’m really excited. The company is amazing, their culture is awesome, they’re growing. So yes, it was a really good opportunity for me to make sure I felt comfortable transitioning to a full-time role again with the company. A couple years ago, I probably wouldn’t have been able to do it, but…
Meg: And is it virtual or hybrid?
Catherine: It’s hybrid, so I’ll go into the office a little bit, which is honestly really nice. I’ve been working from home for 10 years, and so it’s kind of nice to be around people and actually interact with people — people who aren’t just there for my kids’ basketball games.
Meg: Adult stimulation! With your agency, was everyone else virtual, or was there an office?
Catherine: Nope, we had an office for a short while, but no, everyone was remote. Only one other person was here in Wisconsin, even, and she was about an hour and a half away. So we would get together every once in a while, which was nice, but yeah, everyone was actually all around the world.
Meg: Wow. Yeah, I’m absolutely delighted for you. How is Alex in all these transitions? You two have always had a really dynamic, interesting marriage.
Catherine: We have. Yeah, I think the biggest thing is my stress level is so much less now. And so I think that’s been really helpful for us. I’m more available. I mean, I love to work — I’m a workaholic 100% — but I’ve been able to, by 5 o’clock or so, leave my computer, walk away. We joined a gym, we’re going to the gym as a family. So I think that’s been really good.
Meg: There are some hidden elements of owning your own business — and this is why, Catherine, when I’m working with people I say, you know, it’s going to live in here 24/7. You may be done 8 to 5, but it’s gonna live in here all the time. That’s one of the hidden stressors for people — it just never really does shut off. Pete and I have how many companies, and he woke up this morning and said, I feel like we’re busier than ever. So that is something a big benefit. So, how old are your boys now For a big benefit that you are more available
Catherine: Connor is 16, which is amazing — he has his license, and he’s a good driver, so I feel pretty safe with him driving around, and that has been amazing. So we have 16, then we have a 13-year-old, and then 9 and 7 and a half. The half is very important to him.
Meg: I forgot about how much younger the two little ones are.
Catherine: Yeah, we have the two older and then kind of two younger. And they have basketball now — I think 4 days a week starting in April, so we have a lot going on.
Meg: Well, I’m delighted.
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