$33m Holdco: Teddy Bears to Insurance Claims

October 5, 2026
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wo years ago, the holdco seemed like the thing everyone wanted to build.

That enthusiasm has cooled since, which is for the best.

But today's guest is one of the people who actually built one.

Colin King was on Acquiring Minds in May 2024.

He and his 50/50 partner Joe were at roughly $28 million in revenue then; they're at $33 million now, across 17 acquisitions since 2018 — everything from teddy bear manufacturing to insurance claims adjusting.

They've also sold four businesses along the way, pruning the portfolio as they've upleveled it.

The heart of our conversation is what it actually takes to make a holdco work.

Colin says the number one hurdle is critical mass.

‍A business has to throw off enough cash to hire someone better than you to run it — otherwise you're the operator, and you don't have a holdco, you have a job.

‍Which is what Colin and Joe learned about themselves: they don't want to run businesses directly, they want to buy them and staff them.

Listen also for how Colin got that insurance business.

He bought it alongside a self-funded searcher who now runs it, with equity and no personal guarantee.

‍A model more searchers might explore. Feel free to reach out to Colin to get on his radar.

Welcome back to Colin King, co-founder of Circle City Capital Group.

Read MoreStories

$33m Holdco: Teddy Bears to Insurance Claims

Colin King and his 50/50 partner have paid themselves little since 2018, reinvesting profits back into their businesses.
Colin King returns to discuss Circle City Capital Group, the Indianapolis holdco he runs 50/50 with partner Joe. Seventeen acquisitions since 2018 have been pruned into four groups — consumer (Vermont Flannel, Vermont Teddy Bear), insurance claims adjusting, decor and financial services — totaling roughly $33 million in revenue. Colin explains why critical mass matters: a business must generate enough cash to hire an operator better than you. He's candid about modest personal pay, heavy leverage, delayed gratification and failed deals, plus the hedgehog/fox framing, and how he partnered with a self-funded searcher — equity, no personal guarantee — to buy and run the insurance business.

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Acquisition Snapshot

Industry
Logistics & Distribution
Acquisition Model
Holdco
Partnered
Self-Funded
SBA Acquisition
Yes
Multiple Acquisitions
Yes
Country
United States
State/Province
Indiana

Key Takeaways

The number one hurdle to making the Holdco thing work is it's got to be big enough that you can hire someone you think is as good as you or better to be in the driver's seat of that business.
Colin King
  • Colin King returns to Acquiring Minds to update on Circle City Capital Group, the holdco he runs 50/50 with partner Joe from Indianapolis, which they began in 2018 with an overnight trucking business they personally drove routes for — Joe drove trucks for roughly nine months before a manager and backup driver system were in place.
  • The pair discovered through experience that they dislike direct operating and love sourcing, analyzing and structuring deals; their self-described "hedgehog" skill is finding good companies and placing excellent operators in them, with each portfolio company led by an industry specialist.
  • Colin argues the number one hurdle to making a holdco work is critical mass: a business must generate enough cash to pay someone as good as or better than you to run it, otherwise you haven't built a holdco, you've bought yourself a job.
  • The portfolio now spans 17 acquisitions since 2018 organized into four groups — consumer (Vermont Flannel and Vermont Teddy Bear, with a 60,000–70,000 sq ft Vermont factory), specialty insurance claims adjusting, dried/artificial decor distribution, and financial services (Profit Mastery training plus a Decimal accounting franchise).
  • Aggregate revenue is roughly $33 million today, up from about $28 million at the prior interview, after selling two denim brands in March and a sub-$500K-revenue Montessori school supply distributor two months later; that Montessori business returned roughly 3x the dollar invested via dividends and sale proceeds.
  • Combined EBITDA across the portfolio is approximately $5 million, with Colin and Joe's share around $3–3.25 million after minority investors in several opcos; leverage ran nearly 5x debt-to-EBITDA from 2022 through 2024 and fell to about 2.5x in 2025, with further decline expected by mid-2026.
  • Colin is candid that he earns about 40% of his former W-2 investing salary, with every operator and several employees in each company out-earning him and Joe; they wrote only one equity check back in 2018 and have grown via SBA and other debt while reinvesting in leadership hires and inventory.
  • He illustrates the math with a hypothetical $200K SDE business: ~$100K to debt service, $50–60K for a hired operator, leaving ~$40K against perhaps $50K needed for growth — which is why consumer margins, domestic manufacturing, retail stores, and working capital (a 20% growing $20M retailer can tie up nearly $1 million in inventory) squeeze take-home pay.
  • The insurance claims adjusting business, closed March 2025 and sourced from a husband-wife seller who found them via a podcast, is their second-largest company and far higher margin; Circle City owns just under 60%, with two key employees and a local self-funded searcher co-investing — the searcher runs it as CEO with equity, full autonomy, and no personal guarantee.
  • Colin positions Circle City as closer to Berkshire than private equity — buying to hold indefinitely while building terminal value and strong leadership teams that remove key-person risk — and acknowledges misses including two premature ERP implementations costing six figures, an Amazon-exposed brand over $1M in revenue that went to zero, and a website redesign that cratered one acquisition's revenue by about 70%.
I don't make even as much as I was making on a W2 basis when I left the investing world. Every person who runs one of our businesses also makes more than we do.
Colin King

Introduction

Listen to the introduction from the host

Two years ago, the holdco seemed like the thing everyone wanted to build.

That enthusiasm has cooled since, which is for the best.

But today's guest is one of the people who actually built one.

Colin King was on Acquiring Minds in May 2024.

He and his 50/50 partner Joe were at roughly $28 million in revenue then; they're at $33 million now, across 17 acquisitions since 2018 — everything from teddy bear manufacturing to insurance claims adjusting.

They've also sold four businesses along the way, pruning the portfolio as they've upleveled it.

The heart of our conversation is what it actually takes to make a holdco work.

Colin says the number one hurdle is critical mass.

‍A business has to throw off enough cash to hire someone better than you to run it — otherwise you're the operator, and you don't have a holdco, you have a job.

‍Which is what Colin and Joe learned about themselves: they don't want to run businesses directly, they want to buy them and staff them.

Listen also for how Colin got that insurance business.

He bought it alongside a self-funded searcher who now runs it, with equity and no personal guarantee.

‍A model more searchers might explore. Feel free to reach out to Colin to get on his radar.

Welcome back to Colin King, co-founder of Circle City Capital Group.

About

Colin King

Colin King

Colin King is the co-founder, with his 50/50 partner Joe, of Circle City Capital Group, a holding company based in Indianapolis — the "Circle City" of its name. Before entrepreneurship, Colin built a career in accounting and finance, earning his CPA and working in the investment world analyzing and investing in public companies. That analytical grounding — building and managing a portfolio, sizing up businesses, understanding how earnings and balance sheets actually work — would later become the backbone of his approach to acquisitions. His wife is also an accountant.

Joe arrived from a very different direction: a background in operations and marketing, including a stint with Google that had him flying around the country standing up support offices. The two met with a shared, fairly modest ambition — to buy a single private business and run it full time.

They closed their first deal in 2018, a small overnight trucking company that delivered auto parts, while Colin was still holding down a full-time W2 job. The experience was humbling and hands-on, and it seeded the ideas that became a multi-company holdco. Colin first appeared on Acquiring Minds in May 2024, when the portfolio stood at roughly $28 million in revenue.

If making money becomes the focus, it actually feels harder. Just being good, being a good operator - the money turns into a byproduct of that.
Colin King

Show Notes

Colin King and his 50/50 partner have paid themselves little since 2018, reinvesting profits back into their businesses. 

Topics in Colin’s interview:

  • Growing Circle City Capital’s business portfolio
  • Don’t call them private equity
  • Why Colin stopped wanting operational roles
  • Why critical mass matters for holdcos
  • He still earn less than operators
  • Holdco strategy versus industry-specific rollups
  • The fox versus hedgehog framework
  • Learning through hands-on operating experience
  • Why chasing money can make things harder
  • Costly mistakes and failed acquisitions

References and how to contact Colin:

Get a complimentary IT audit for acquisition diligence or post-close transition.

Contact Jenny to learn how Engage can run people operations in your acquisition:

Get complimentary due diligence on your acquisition's insurance & benefits program:

Connect with Acquiring Minds:

Edited by Anton Rohozov and produced by Pam Cameron

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Episode Transcript

Show Transcript

[00:00:00 - 00:03:21]

Host: Two years ago, the Holdco seemed like the thing everyone wanted to build. That enthusiasm has cooled since, which is for the best. But today's guest is one of the people who actually built a Holdco. Colin King was on acquiring mines in May 2024.

He and his 5050 partner Joe were at roughly 28 million in revenue then. They're at $33 million now across 17 acquisitions since 2018, everything from Teddy bear manufacturing to insurance claims adjusting. They've also sold four businesses along the way, pruning the portfolio as they've up leveled it. The heart of our conversation today is what it actually takes to make a Holdco work, collins says.

The number one hurdle is critical mass. A business has to throw off enough cash to hire someone better than you to run it. Otherwise you're the operator and you don't have a Holdco. You have a job.

Which is what Colin and Joe learned about themselves. They don't want to run businesses directly, they want to buy them and staff them. Listen also for how Colin got that insurance business. He bought it alongside a self funded searcher who now runs it with equity and with no personal guarantee, a model more searchers might explore.

Feel free to reach out to Colin to get on his radar. Welcome back to Colin King, co founder of Circle City Capital Group. Welcome to A Quarter Acquiring Minds, a podcast about buying businesses. My name is Will Smith.

Acquiring an existing business is an awesome opportunity for many entrepreneurs and on this podcast I talk to the people who do it. You know Enzo Technologies as one of the leading IT managed service providers serving the search community, led by Nick Akers, an Acquiring Minds guest who bought the 35 year old business. The team at Enzo regularly works with searchers and their acquisitions and one feature of acquired businesses that Enzo is seeing over and over is the need to implement cybersecurity promptly during the transition. So many acquired small businesses either have glaring vulnerabilities, lack security best practices or both.

That step one to de risk the deal you just closed should be addressing these issues. INSO is your full service IT MSP for post close stability. They assess your target, surface the biggest risks in plain English and give you a day 1 through 30 plan to cut exposure, prevent downtime and even find cost takeouts like bloated telecom bills. Check out enzotechnologies.com I N Z O or email Nick directly at nicknzotechnologies.com Colin King welcome back to Acquiring Minds.

[00:03:21 - 00:03:24]

Guest A: Thanks for having me. Excited to be back Colin.

[00:03:24 - 00:04:02]

Host: You came on back in May 2024. At the time you were at what we said in the headline was about $28 million in aggregate revenue across your Holdco. A Holdco that started very modestly. We heard that story in depth.

You're back today to share how things have gone, how things have evolved in the last 2 1/2 ish years. So let's begin. Colin, for those who didn't hear your first interview with a super condensed version of that, tell us the whole kind of first six or seven years of the Holdco and take us up to where we were last time.

[00:04:02 - 00:05:20]

Guest A: Yeah, just like eight or nine years in two minutes. Right? So long story short, my background, accounting, finance background, partnered with a 5050 business partner. He and I are still 5050 on everything we do.

He's got an ops and marketing background. We both had a desire to buy a single private business and sort of run that full time. That was the, that was the starting point. That has evolved to, I think we're at 17 acquisitions now since we started in 2018.

We bought our first company in 2018, Little Overnight Trucking business. For anybody who doesn't remember, lots of hard earned lessons in that. So we've opportunistically bought our way into, I'll call it four groups of businesses that we own today. We've sold a few things along the way, including a few of them this year.

At the time that you and I last chatted, we had just closed on the Vermont teddy bear acquisition. We just bought this teddy bear manufacturing and retail business. So we were only like, I don't know, 30 or 45 days into that business now or two years down the road. Lots of as has happened in that company, we've bought a few other things since then.

So yeah, I think the strategy and the portfolio has definitely evolved since our last conversation.

[00:05:21 - 00:05:40]

Host: Super, thank you for that Colin, and for me, speaking of that first business you bought, the overnight trucking business. The indelible image from our interview, our first interview was you and your partner driving in the middle of the night, you know, doing the work of the business. Give us that little anecdote.

[00:05:41 - 00:06:17]

Guest A: Day one, right? You, you buy the company. This is literally, this is what happened day one. We bought the company.

We show up and we say, all right, great, these are the trucks that we own. This is the team we got. We're about to go deliver some auto parts. Two guys, no call, no show.

We're both in a truck dropping auto parts off and 400 miles away from town. And so I'm like, at the time I had a full time job when we first started this took me a few months before Joe and I plunged in with both feet and I was like, okay, great, let me just go deliver some auto parts until 6 o' clock in the morning and then I'll just take a quick shower and go to work and we'll come back at it.

[00:06:17 - 00:06:20]

Host: And you guys had to do that for a few weeks, was it?

[00:06:20 - 00:07:10]

Guest A: We probably. Well, he drove trucks for maybe nine months until we installed a team and a backup system and kind of got that thing up and running to where we wanted it to be. It turns out finding good quality people that want to work from 11pm to 11am is somewhat challenging. Right?

So it took us about nine months before he was able to peel out of that. We put a manager in place and like a backup driver system. So if there's a no call, no show, then you've got someone else who can step into that seat. That took a while to get there, but once we got to that point, it was actually a decent little business.

Probably didn't recoup all the like extra time, you know, headache effort that we had put into it, but it wound up being an okay outcome. Sold that business about 18 months later and then use that as the foundation, if you will, to redeploy into what

[00:07:10 - 00:07:19]

Host: is our portfolio now and when and why did the strategy go from buy a single business and grow that to a holdco?

[00:07:19 - 00:09:26]

Guest A: We formed these, these, these thoughts. We built this thesis while driving trucks together in the middle of the night. I'm only half kidding, actually. There were a couple of times where we're both in the same truck, you know, running a route and you wind up talking about a lot of stuff over the course of 12 hours from, you know, midnight to 11am so we got to know each other a lot better during that time period.

So we, you know, we talked about my career in investing in public companies and building a portfolio, talked about Joe's career, you know, flying across the country, standing up support offices for Google and what our skills are and what we like. And so we didn't necessarily hatch this grand plan to say, hey, we're going to build a Berkshire Hathaway. But we like the idea of having multiple things going on, multiple horses in the race, if you will, and then getting to that scale point where we both found that we really like looking at deals, right? Like the notion of looking at deals, finding a good company and figuring out how to buy it.

So if we can skate closer to that, we're going to need some scale. So that we're not literally and figuratively in the driver's seat. So when we sold that business, let's see, maybe in. It was June 2019 through Q4, 2019.

We bought. We bought our first decor business in June of 2019, and then we bought our denim blue Jean business in October 2019. And actually about 15 days later, in October 2019, we bought our first accounting firm. Virtual accounting business, just bookkeeping.

So that was, you know, call it three or four months, having acquired three businesses. And the original thought was, well, two of these are E Com, and we've got a pretty good sense for how to do that. You know, Joe is sort of managing that side of the house. And on the accounting side, this is work that we already needed to do for our own businesses.

I had a background, still have my cpa, have a background in accounting. And so, okay, let's just turn a cost center into a revenue center. And now we've got sort of two different verticals that we're in in accounting and E commerce. That was the thought process going into the fourth quarter of 2019.

[00:09:27 - 00:10:01]

Host: Okay, well, each of those is probably its own story. And we did give. Give each of those some airtime last time. We're not going to have time for that today.

But it sounds like. Colin, to clarify in my own mind, your kind of how you see things today, your enthusiasm for buying businesses and for the. The act and process of actually buying businesses, sourcing and then doing the deal was something you recognized early on as something that you both enjoyed and where ideally you'd spend time.

[00:10:01 - 00:10:02]

Guest A: Absolutely.

[00:10:02 - 00:10:19]

Host: Yeah. So operator. Being an operator was something you were doing out of necessity, but it was never the goal to be the primary operator of this, of a single or any of the businesses. You'll kind of plug in where you have to, but only on a temporary basis and only.

And it's less than ideal.

[00:10:19 - 00:11:17]

Guest A: Yeah, I think the evolution was I liked the idea of being an operator at the outset and saying, hey, I think in doing this I can make more money and have maybe, maybe not work fewer hours, but a more flexible schedule. And I don't mind being the guy who's going to run the ship, so to speak. I think I came in with that thought process and then a couple years of being in that seat and doing that activity found out, hey, I really don't like this. Right.

Managing people, managing a team and scaling those things is not for me, especially after finding people who are much better at it than we are. But the idea of looking at businesses and analyzing them and figuring them out and finding a way to get it done and finding a good person to put in that seat. Yeah, I think we really, really, really latched onto that. And maybe only in the last 12, 18 months have we truly accepted like, hey, that's our unique skill.

That's what we bring to the table. Like let's go find and partner with, with good people to run these things and let's just go keep doing what we do best.

[00:11:18 - 00:11:47]

Host: Okay, so maybe you just answered my next question. But, but even though there was an early inkling that you liked to do deals, there was a crystallization of that. There was a crystallization of that more recently where, okay, the, the model going forward is going to be that we're gonna be the deal engine for our Holdco and partner and put talent in to run those businesses. We are no longer gonna do that to the extent we can help it.

[00:11:47 - 00:12:26]

Guest A: Yeah, absolutely. And honestly, you know, you get enough reps at it, you wind up getting better at it each time. Right. You learn a few things from the last one.

And the different industries, you know, they add different contributing factors to those lessons. And maybe this isn't helpful for the people who are looking for their first business to buy. But you know, honestly, once you, once you're already in an industry, it becomes significantly easier to find another company to buy. I mean honestly, the deal flow aspect has really only gotten easier over the last, over the last five or six years.

So that is like least of our challenges at this point in time. So yeah, absolutely.

[00:12:27 - 00:12:37]

Host: Before we go further, Colin, because we're going to, I want to really want to continue unpacking this. Give us a snapshot of where things stand today. The Holdco. And I haven't named the HoldCo CircleCity.

[00:12:38 - 00:14:44]

Guest A: The HoldCo has a name. It is CircleCity Capital Group Inc. It's a mouthful. That is the name of the holding company.

For the time being we've got, I'll call it four groups or four operating groups that we're in today as opposed to four specific businesses. They are consumer insurance, decor and financial services. In the consumer business, we own Vermont Flannel and the Vermont Teddy Bear Company. So we both manufacture and retail flannel shirts, pants, et cetera and teddy bears.

Jointed and plush teddy bears. We got a factory up in Vermont, 60, 70,000 square foot factory and we just make teddy bears all day long. So that is our consumer business. One team runs those two brands.

Our insurance business we just acquired in March of this year and I'm sure that's One we'll want to talk about. It's a specialty claims adjusting business. So we don't do any, you know, standard, you know, fender bender type adjusting work. We don't do any chasing weather or anything like that.

It's, I'll call it non standard insurance claims adjustings. We work with insurance carriers as our primary customer. Um, and that is the second largest company now behind the consumer business after doing that deal. Our decor business is a distributor of both dried and artificial plants, flowers, branches, decorative items, et cetera.

We sell the wholesalers, retailers, wedding planners, decorators, you name it. And then last is our financial services group. And within that there are two businesses. One is a financial training and education company called Profit Mastery.

We teach business owners how to read and use their financials to make better decisions. And then we've got an accounting firm, bookkeeping and tax technically. And it's actually a franchisee. We were one of the initial franchisees of a firm here in Indy, and that's called decimal.

And we got a team and revenue and clients as part of that. So those are the four groups is how we think about what we own today.

[00:14:45 - 00:14:50]

Host: And what is the revenue number, the aggregate revenue number to give us a sense of size for the whole group,

[00:14:50 - 00:15:35]

Guest A: for the whole portfolio. So, okay, we sold two denim blue jean comp. Two blue jean brands in March of this year. And then maybe two months later we sold our smallest company, our Montessori school supply distributor.

I don't remember last time we chatted. We kind of left that conversation of like, hey, we got this large company and we got some smaller stuff. What should we do? Well, we wound up pruning some of the smaller things as we've kind of up leveled the rest of the portfolio.

So we sold a few things since the last time we chatted. We're probably about 33 million in total revenue. Today is where we stand with the recently acquired insurance business and the accounting firm and pulling out the blue jean businesses in the Montessori business.

[00:15:36 - 00:16:05]

Host: Mm, great. Okay, thank you for that, Colin. Very helpful. Now when we talked last time, Holdco interest was probably peaking.

As you and I discussed on the pre call a couple weeks ago, it does seem that that excitement does seem to have subsided a little bit, which is probably a healthy development because as you know, we were all, all of us were a little bit skeptical about, you know, about the Holdco vision for various reasons.

[00:16:05 - 00:16:08]

Guest A: It was a red flag to say you wanted to build a Berkshire, you know, like.

[00:16:08 - 00:16:49]

Host: Yeah, right, right. Although of course I also had plenty of People on you included, that really did it. So it's, it's, it's, it's both kind of overdone fantasy, but also very real. The thing is, one of the critiques about the Holdco enthusiasm is that people wanted to do it because it sounds cool as opposed to the sort of proper, if I may be so bold as to, to assert that the, the proper reason to do a Holdco, the, the, the corporate hold cos of old, the Berkshire Hathaways, which is just diversification.

You know, you, you get big enough and you don't want to be exposed to the, the single industry of one business.

[00:16:49 - 00:16:49]

Guest A: Yeah.

[00:16:50 - 00:17:01]

Host: Was that, was that part of your strategy here or was yours, did your hold co develop sort of, kind of organically because you guys like deals and it's kind of where opportunistically it led you?

[00:17:02 - 00:18:00]

Guest A: I think it was born out of the diversification idea, especially early. We had pretty heavy consumer exposure and I think that's something we were actively trying to move away from and finally got a key piece of that puzzle solved in this year. But absolutely, it's having multiple horses in the race. It's the idea that, hey, I'm not beholden to one thing, like one thing will not destroy me.

That's absolutely part of it. I think another part of it, you know, is, is, is actively liking that, that buying, building, bolting on, finding good things and just letting them continue to go to work. And some people will tell you like, hey, I can't take my eye off the ball on this one and it'll still work, grow, compound, whatever, and then go do something else. Like I just don't have the bandwidth or capacity to do that.

But you know, if you can solve for that like that is, that is the other part of it is you've got multiple things in growing industries that are working for you over time.

[00:18:01 - 00:19:34]

Host: Longtime acquiring MIND sponsor Aspen HR is now part of Engage peo. Engage helps acquisition entrepreneurs, business buyers like you, take care of their new employees and build trust from day one. Whether it's an asset or stock purchase, Engage provides a turnkey solution for payroll and taxes, hr, admin and technology, employee benefits, retirement plans, workers comp and more. They're also always a phone call away.

So you can receive HR guidance from licensed employment attorneys promptly as those inevitable people issues come up. With Engage managing your people infrastructure, you as new owner of your business can focus on building relationships, operating the business and driving growth. To learn more, contact Jenny thier directly at jthehr j t h e a r@engagepeo.com or click the link in the notes. The example you just said where somebody can't figure out how to spread their attention, let's say they can do it.

But there's still just sort of a structural argument that kind of the founder energy argument or the focus argument, that there is an X factor of performance when you're focused on a single thing as opposed to having your attention split.

[00:19:34 - 00:20:01]

Guest A: I think that is the, that's the rule, not the exception, is that, hey, you should focus on the best opportunity, go all in on that, make that a hundred bagger and call it a day. Right? And I think that's part of the reason that the Holdco doesn't get as much attention and is a lot harder. There's other reasons a lot harder.

But that is one of the reasons that I don't think more people pursue it. You know, why would I do that when I can just go do more at this one thing that I'm already in and make it huge and awesome?

[00:20:01 - 00:20:23]

Host: Well, and similarly, maybe it's another way of saying what you just said, that there's the capital allocation argument or the attention allocation argument, that if you have a Holdco of four businesses or four groups, that one of them presumably is outperforming the others. And so every time you look to deploy a dollar or a jewel of energy, it should go there as opposed to the others.

[00:20:23 - 00:22:04]

Guest A: That is the real challenge. And that's what we ran into with our. We had a phenomenal person running our Montessori business. She was absolutely amazing operator, but the business was subscale.

And so, you know, allocating time and resources to figure out how do we help this business doing, you know, I'll call it less than $500,000 in revenue when your largest brand was doing 15 million. It's like, okay, those become pretty challenging conversations internally to say, like, let's figure out, you know, where to go spend our time. Right. So that is, is one part of it.

I think the concept of maybe on the last time we chatted, I mentioned the concept of critical mass. And I may be more of a believer in that idea now than I ever have been. And I think that's the number one hurdle to making the Holdco thing work is it's got to be big enough that you can hire someone who you think is as good as you or better to be in the driver's seat of that business. Like that is the only way that it makes it work is that you can let go.

Like you can actually Mentally, physically, let go of being in that role and then have someone who's so good that you're like, yes, I feel better that they're there than I am. And that thing's going to work while I go figure out what's the next level leg to the stool, so to speak. But you've got to have enough cash flow to be able to pay for that person, right? And so the conversation around, like, oh, I'm going to buy a business.

I'll put myself in as the CEO, and then I'll have room for some debt service, and then maybe a little bit room left over after that. Like, that whole math argument changes when you're like, okay, I'm going to buy this business. I'm going to put in a CEO who's not me, and they're going to get well paid because they need to be. Otherwise they're not going to be that good.

[00:22:04 - 00:22:04]

Host: And.

[00:22:04 - 00:22:14]

Guest A: And I'm going to pay for the debt service. I'm still either not making a lot of money or making much less like that. Just that math argument becomes a lot harder for the person who's looking to buy a company, you know?

[00:22:16 - 00:22:24]

Host: Well, since you bring it up, Colin, let's do, if you don't mind, talk about how much money you're making for yourself, you and your partner.

[00:22:24 - 00:22:24]

Guest A: Oh, gosh.

[00:22:24 - 00:22:52]

Host: Because. Because in fairness to the audience who see the 30. Well, who will see the $33 million number in the headline, and the distance between that number and what you're putting in your pocket on a monthly basis or every two weeks is a far one. So be as transparent as you can about what your personal take home has looked like these last eight years.

[00:22:54 - 00:26:24]

Guest A: Oh, man. Where to start this? Where to start this? Is my wife going to listen to this?

I don't know. It's several things. Several things. One, total transparency.

I don't make even as much as I was making on a W2 basis when I left the investing world. I'm still at probably 40% of what that number is. Every person who runs one of our businesses also makes more than we do. And there's probably several people within each of those companies who are making more on a W2 basis than.

Than what Joe and I are making. And I think that's part of the game. If you're trying to go this direction and say, hey, I'm going to have a leadership, true leadership team in each of these companies. And so building this, it's probably been frustrating for my wife to see, like, hey, look, there's four or five other people running these businesses.

You could just do that and make three times what you're making now. It's like, yeah, I think that was part of the decision to forego that role and say, I don't want to be the operator, I want to keep building and bolting onto this thing. So part of it has been accepting that and making those investment decisions. From an absolute standpoint, like 30,000 foot view, we have some lower margin businesses than what other people in this industry might be looking at.

So we're in the consumer space and most retailers do not have excellent margins. So we've got to manufacture products, we're manufacturing domestically, we got brick and mortar retail stores. I mean, all these things that are sort of working against us from a margin standpoint. So as a whole, we're probably a lower margin business than some of the other companies you're talking to.

The insurance business helped that a decent amount. But let's just say that if we're $33 million in revenue today, and on that, you know, combined EBITDA is probably, I don't know, maybe 5 million bucks something in that territory. In our OPCOs, just because of the structure of what we're pursuing, we have some minority of investors in several of those operating companies and we can get into why that's the case, but we do. So we don't own 100% of all the businesses that are in our portfolio and that's okay by us.

So our share of that might be, I don't know, three, three and a quarter million from that we've got to pay for the debt service. And remember, we started highly levered. We have not injected tons of personal capital into this thing other than when we started back in 2018. That was our only equity check that we wrote into this thing along the way.

So we've used the sba, we've used lots of debt to get to where we're at and we're getting over that hump. But it's pretty recent. It's taken years to get over that hump. We were probably four or five times levered as recently as 2023, 2024.

So that's a big chunk of it. So takes away an enormous chunk. And then the other piece of it is on the working capital side. So we've got two very large, very fast growing consumer businesses.

And I mean, just in theory, if you've got, let's just say a 20 million revenue retail business and it's growing 20%, so call it an extra $4 million of revenue, and you got 20% of that tied up in inventory and working capital. You're talking about almost a million bucks from just, from growing that. Right. From building inventory standpoint.

And that's not even considering, like the crazy insane seasonality of selling flannel. We started making short sleeve flannel now. Right. So now I can wear this in early September.

[00:26:24 - 00:26:26]

Host: I was, I was wondering.

[00:26:26 - 00:26:26]

Guest A: Yeah.

[00:26:27 - 00:26:28]

Host: You look sharp, sir.

[00:26:28 - 00:27:26]

Guest A: Yeah, thank you. You got to promote the product. Right. So, so all those things, they, they eat into that.

And so, and then behind that, you know, as the people who own the company early in the process, we're always the little people on the totem pole. So if seasonal swings got in the way, it's like, okay, we'll, we'll pause on our paycheck for a while if we need to, just to like, get through this, this inventory build season. So you just have all these things that are working against you to get to that bottom line, net number. When I first started doing this, it was easy to dream like, oh yeah, 200 grand of cash flow and pay 600k for it.

Okay, 200k, maybe I got, you know, 80k of that. Going to debt service. Sweet. I'm going to walk away with 120k of free cash to go do other stuff with.

And like, I think that quickly became like overly simplistic thinking. Right. Like, accounting is way more nuanced than that.

[00:27:26 - 00:27:35]

Host: So I actually followed you up until that last example. So on a little example like that, $200,000 of cash flow, you think you're going to buy this business?

[00:27:35 - 00:28:12]

Guest A: Yeah. So imagine a business. You got $200,000 of operating cash. Right.

That's what they're marketing SDE. Right. That's what the seller's marketing it at. You're going to buy the company.

And let's just say, hypothetically, your debt service is going to be 80k a year. Maybe it's closer to 100k a year. I don't know what that actually looks like. So 200k of cash flow.

Okay. I got 100k of debt service, and that's both my principal and my interest. Right? Okay, well, for us, we elected to hire a manager, an operator to run the business instead of doing it ourselves.

Okay. There's another 50 or 60 of it gone. I'm just like, we're ratioing the numbers here, right?

[00:28:12 - 00:28:12]

Host: Yeah.

[00:28:12 - 00:28:53]

Guest A: So 200k, that's a hundred now. Okay, I got a hundred to play with now. I spent 60k to go hire a person great. I got 40k left.

Okay, well, we're trying to grow the thing too. Okay, well, that's gonna cost you maybe 50, right? So. Okay, I don't have 50.

Now I gotta figure out where I'm gonna get. Okay, well, maybe I'll go borrow some more money to help fuel that growth. Growth, that is what we had done for probably four or five years until we hit that critical mass point because the name of the game was somewhat like, we have to have enough revenue to pay for enough people to go do these various things. So it was.

I'll call the 2022-2024 period, like, pretty painful in making those investments intentionally.

[00:28:54 - 00:29:16]

Host: Well, and so it really does come down to that. You were like any entrepreneur kind of in a bootstrapping situation. That's maybe the wrong choice of words here. But you were lean and plowing as much as you could back in while still being able to feed your family sort of situation.

So it's actually, in some ways, it's just the classic story.

[00:29:16 - 00:29:45]

Guest A: Yeah, absolutely. I mean, I think that's. I think that's it. Yeah.

And just electing to make those decisions maybe earlier than we, we would have liked to, but partly, Partly out of necessity. Right. And partly because you just don't know when good people are going to come along. And then partly because, hey, that's what the end game is trying to be.

And if we can get there, like, it's. Yeah, it's. It's taking a little bit of pain to know that, hey, when I come out on the other side of this, we're going to be better off. And knock on wood, that's where we've come out so far.

Great.

[00:29:46 - 00:29:52]

Host: You said you're close to getting over the hump. What does that mean? That you're about to pay off all that debt.

[00:29:52 - 00:30:59]

Guest A: I keep this little tracker of just our annual take all of our port codes and just sum them up into an aggregate number and I track it by year. And so I have that. And I'm just looking at the 2022, 3, 4, 5, and where we're at today. And I've got our number with revenue, I got the EBITDA number, and here's our total debt outstanding.

And so, I mean, from 2022 to the end of 2024, we were almost 5x levered, so 5x debt to EBITDA. And now in 2025, that fell to two and a half. And now I think it should be actually considerably lower than that. Midway through 2026, when I update Those numbers.

So that is partly that 22 to 24 period. Just hiring a bunch of people to wear those different hats to fuel the growth that's buying the inventory. Those are all the things that we were talking about. And now we're starting to see the, the EBITDA come through the other side and it's like, okay, great things and your debt's amortizing along the way.

So it's like this combination perfect storm of like factors playing out that's helped us.

[00:30:59 - 00:31:14]

Host: Okay, but to be clear, it's not be. Yes, you're. The amortization means that your debt is dropping year by year. But that's very linear.

Really what's taken care of that ratio or made it, you know, made it look so much more attractive is because you've.

[00:31:14 - 00:31:44]

Guest A: Your EBITDA earnings growth. Yeah, the earnings growth. Yeah, that's absolutely. Has been a contributor and part of that because you know, you buy a profitable company and it, it has some growth to it, which is important.

You know, I think when I first thought hey, this is a viable, a viable avenue, like hey, just buy a company even if it's not growing earnings like 100k a year. Cool. That's. That, that's awesome.

Like, I think you still have to have some plan for taking that 100k to. You don't have to double it overnight. But like how are you going to grow that thing? Right.

Because it absolutely 100% helps the outcome.

[00:31:45 - 00:31:59]

Host: When your wife has pushed on you about the take home, what has your answer been? You just gave us the kind of the technical answer. I suspect there's a vision that you're selling at the dining room table. What is that?

[00:31:59 - 00:33:12]

Guest A: These businesses have, have terminal value to. I mean that's part of the reason that people want to buy a company. Right? It's like, hey, you get a W2.

Well, cool, I get a W2. But I also own this business that I can go and sell at some point in time. Time. So I've got kind of some backend value in the business itself.

So I know that we're building terminal value in the companies that we own. Like these things are valuable businesses and I think we've made them more valuable. I haven't. But the people who are running them are making them significantly more valuable.

And I know that that's there. And so it may not translate. It's like being house poor, I guess. Right.

Like I got this really valuable house and maybe it's appreciating in value, but it doesn't generate cash. Flow today, so. So the cash flow that it gives to me is pretty small, but I think it'll expand over time. But on the back end, I own this thing that I think is immensely valuable and growing in value, and that's great.

My wife, I know she'll listen to this, so she'll probably give me a hard time, but she appreciates it. But I know she would rather see more cashflow today. But she's also an accountant too, so I'm like, come on, you got it. Of all people on the planet, you should understand this more than, more than the rest of the world too.

[00:33:15 - 00:33:19]

Host: The ultimate grownup marshmallow test.

[00:33:19 - 00:33:20]

Guest A: This is. Right?

[00:33:20 - 00:33:39]

Host: This is an exercise in delayed gratification. You're. You're maybe not a mini Berkshire Hathaway. You're a mini Chen Mark at this point, Colin and, and Chenmark is always talking about the delay.

Delayed gratification, I mean, I guess isn't. When it comes to compounding that, that's always the go to personality trait that's needed. But here we, here we have it again.

[00:33:40 - 00:34:46]

Guest A: Yeah, that's absolutely right. I do think it, it emphasizes the importance of like building something that does have that terminal value though. Right. And I don't think most, most people aren't looking to buy a business that can't be eventually sold at some point in time, but making moves to take it closer to being able to sell and maybe at a higher multiple than what you paid for it.

Like, I think those are, those are steps that are worth considering. I had a friend slash mentor a long time ago who told me, find a way to. I can't remember exactly how he phrased it. Something like, find a way to buy things cheap and then sell them.

Overvalued. Right? Like, what can you do to make something overvalued along the way? And what are those attractive features that other people might be looking for?

And not to say that you need to make all your decisions based on that thought process, but it is an interesting thing to think about. And I see H Vac multiples and now accounting for multiples and what people are paying for for certain types of businesses. And it's like, okay, well, what can you do to kind of morph your company to look and feel more like what people are chasing after? I don't know.

Worth considering.

[00:34:47 - 00:35:35]

Host: The other thing about your point about adding value is all of the leadership that you're putting in place is sort of hard of. As hard as that is. And while maybe ostensibly it's to enable the holdco so that you guys can be sitting one level above each individual Portco. It does also add a lot of value to the Portcos to have strong leadership in there because then they become self contained entities that can be sold at some later date as opposed to having all this founder or owner dependence which is one of the classic weaknesses in a small business.

So in some ways putting in great leadership. This sounds a little bit crude, but it's like double dipping. You're both enabling your Holdco and adding a lot of value to that individual Portco.

[00:35:36 - 00:37:38]

Guest A: Yeah, I think that's right. And it's just looking at the evolution of our businesses. So just pulling out our consumer business for example. I think when we started the evolution of that business we had a blue jean business we bought in 2019, we bought flannel in 21, in 2023 we bought another blue jean brand.

And then in 2024 we bought teddy bear and then in 26 we sold the two denim brands. So that's kind of the trajectory there. That business started with maybe four employees and it was Joe and I and we were, you know, packing orders at the warehouse on Black Friday and shipping them out and doing this, that and the other for the business like hands and everything. Joe is doing some of the PPC marketing himself.

And so, you know, that's where that business started. And I look at it today and it's like this, actually pretty awesome to see it unfold. Like we got a CEO, cfo. They have those two titles and they're both phenomenal people and they do an excellent job.

We got ahead of retail and he does an amazing job. He's probably, I don't know if he's going to listen to this. He's probably going to become the CEO of that company. Like he is just a very strong operator.

Like he's got that, he's got the chops for that. We've got an amazing marketing team, we've got an amazing product dev merchandising. I don't even know how you would describe that world of business. But now we have all these functional areas that are vitally important to making that business work.

And you have a person at the top who can make that go. And all of those require investment, like OPEX investment maybe earlier than you want to because it kills your EBITDA to do so. But they also require some level of revenue growth. But now that we have those, I'll call it six or seven people who sit on that quasi leadership team, that business is way less like it's not, not even like me being the key person risk and becoming, hey, the CEO is now the key person risk.

Like you got a whole team that's thinking about their individual department. Like that's. I think that's pretty awesome, you know.

[00:37:38 - 00:37:38]

Host: Yeah.

[00:37:39 - 00:37:58]

Guest A: So I think that's like trying to move to that mindset and say I'm not just trying to pass the buck and say, yeah, we hired an operator and now they're still the key person risk. Like I think you want more, you want more scale than just that even. Right. And we don't have that for every opco.

But like that's. That that would be the model is to get to that point.

[00:37:58 - 00:38:02]

Host: That's really cool. K, congratulations on your progress with that.

[00:38:02 - 00:38:03]

Guest A: Thank you.

[00:38:03 - 00:38:58]

Host: I want to circle back to the Holdco model structure here and press you on one like alternative path that this might have gone, which is, which is programmatic acquisition or, or highly inorganic growth in a single industry. So obvious flaw to that is that you don't, that you don't get the diversification. But arguably you, you, what you lack in diversification, you get up, you, you make up for in the multiple expansion because you're just going to be getting, you're going to be aggregating so much more EBITDA in a single industry. And those multiples start to get, you know, really interesting at.

You're at five across the whole diversified portfolio. If you know, if you were five in a single industry, the package would be more valuable for sure. And you and Joe could still scratch that itch of doing deals.

[00:38:58 - 00:38:58]

Guest A: Yeah.

[00:38:59 - 00:40:17]

Host: So there is the, there is this kind of emerging or ever more popular model now of kind of the entrepreneurial rollup where you buy the platform. You probably should, I would say at operate that business, learn H Vac or, or learn accounting or whatever it is so that you can really talk the talk, walk the walk for the first couple of years, you know, earn your stripes and get it on firm enough footing that there's leadership or a president there who can, who can do the operations of that business and then in year three, turn your attention outward and start looking for deals and acquisition targets. And if it's a really fragmented industry, as most of these industries that we all play in and talk about, you can go start doing deals and probably do them very well because you have so much experience in the industry, you're accepted as one of a fellow peer owner. It just seems like you could have your cake and eat it too.

In that model. You could be doing deals but also Getting the multiple expansion and in some ways a lot less friction than having multiple groups across multiple industries. Yeah, you're nodding along. You like totally get it.

Uh, so why not?

[00:40:18 - 00:40:33]

Guest A: You probably pick up more. More. I, you know, I think about the term synergy, right. And it gets, it, maybe it gets thrown around loosely, but that can make even more sense in a roll up because at that point you can, you can buy something and fold it into your existing ops, right.

Maybe you already have a warehouse. You don't need another warehouse.

[00:40:33 - 00:40:33]

Host: Exactly.

[00:40:33 - 00:41:00]

Guest A: You may not need this other team because you already got a team. So like in theory, you could maybe, maybe make even more money doing a roll up by like bolting stuff onto what you already own, like tight operational integration. Whereas for us everything's decentralized. So we got to stand up a whole new team that's, you know, who's doing the accounting for this business?

Well, they're not the people who are doing the accounting for that business. Right. So we got to stand up something new every time. So is your question why not, why not pursue that?

Why?

[00:41:01 - 00:41:01]

Host: Yes.

[00:41:01 - 00:41:14]

Guest A: Yeah. I mean, so I think this comes back to. It's the Jim Collins hedgehog and the fox thing, right? And so the roll up is still being a hedgehog.

The hedgehog is, I think that's the specialist, right? That's the one.

[00:41:14 - 00:41:16]

Host: Remind us of the framework here or the metaphor.

[00:41:16 - 00:42:46]

Guest A: Jim Collins. Good to great. I think it's in good to great. He talks about this concept of the fox versus the hedgehog, right.

And the fox is into a lot of things. He's a generalist kind of wandering. And that's sort of, I think, how I view myself to some extent. But then there's the hedgehog, who is very, very specialist minded.

Going to learn everything there is to know about H Vac or accounting or whatever, go deep, go really, really deep on that one topic or concept and then do amazingly well at it. Because they're a specialist. Right, of course. And so when I think about our, what we're building and how I view myself, I'm not necessarily saying I'm a fox and I'm interested in lots of things, although that is, that is true.

I like to, I like to learn a lot of different things and look at a lot of different things, but the person executing that roll up should be a hedgehog in that industry. And I think what we have is we have a hedgehog at each of those seats running each opco. And that's awesome. Like, I want someone who loves making teddy bears and I want to know everything there is to know about making teddy bears and doing them the right way and selling them the right way and all that jazz.

That's awesome. That's not me, my hedgehog or our hedgehog. Joe and I is in finding good companies and finding people to run them. And so looking at businesses and figuring out what makes this a good business, what makes this an attractive acquisition like that is our hedgehog.

So yeah, in theory the roll up could scratch that itch, but it still would require being really, really deep on that one industry vertical.

[00:42:46 - 00:43:54]

Host: You know, if you ask owners in the ETA and search community which insurance broker provides highest quality work, great outcomes and has a practice dedicated to searchers and acquisition entrepreneurs, one name comes up again and again. Oberle. Oberle Risk Strategies has worked with hundreds of searchers over nearly a decade and is in fact led by a two time successful searcher, August Felker, which makes Oberle a specialty insurance brokerage for searchers by a former searcher. And if you've got a business under Loi, Oberle will provide complimentary due diligence on that business's insurance and benefits program.

An easy, no risk way to get to know August and the team at Oberle. To take advantage, check out oberle-risk.com that's O B E R L E- risk.com link in the notes. Thinking again about Chenmark and the reason they're top of mind is because I get their newsletter and they, you know.

[00:43:54 - 00:43:55]

Guest A: Yeah and they're awesome.

[00:43:55 - 00:43:57]

Host: I mean they're the essay every Friday night.

[00:43:57 - 00:44:01]

Guest A: They're like what we're doing but further along. Yeah, exactly.

[00:44:01 - 00:44:50]

Host: And you do get from their missives that they are also hedgehogs like you as you describe yourself. And what their thing is is just small business, small business operations and probably operations above even acquisition. But yeah, it's just kind of the nature of this lower, lower middle market and being, because there are patterns from, from industry to industry to industry, I'm acting as if they're all so different but in some ways, you know, it kind of all sort of tastes like chicken. But the culture and the nature and the fragility and the messiness is, is a, is a through line and if that's your hedgehog or that's what you're a hedgehog for, that can be what you're a hedgehog for.

And, and you get the sense that that's their thing. And so I, I, I believe you when you say it's yours.

[00:44:50 - 00:45:59]

Guest A: And I, I, I think what they do And I don't, I, I haven't talked to them a ton to know that, you know, how their model works. But I, I believe they've got maybe more support that they provide at, at their hold co down to each of the portfolio companies. But you know what I told Joe? I, I think the, the perfect world for us would be to spend all of our time looking for the next acquisition, talking to our operators and then figuring out how we're going to go pay for that, you know, allocated capital, so to speak.

And that conversations with the operators, I think those still add tons of value because, you know, it's not like we don't know anything and haven't learned things and things that we can take from this business and apply to this business. So them talking amongst each other and talking to us, like having some structure around that, like, I think that adds a ton of value. So even though it's indirectly operating the businesses, I think it's just brings a different perspective to say, hey, look, I'm not deep in the weeds. Maybe we can offer some perspective on that issue or project or whatever from a different standpoint.

So that's, that's like early innings for us. We don't have the right infrastructure in place for each of these things, but I think that's what we want to build is like, how can we help these guys more from our standpoint, our seat.

[00:46:00 - 00:46:07]

Host: And, and you mean that informally, just with expertise, but also formally with, in the form of centralized services. Some sort of centralized services?

[00:46:07 - 00:46:16]

Guest A: Yeah, yeah, could be a combination. And, and just having those different operators talk amongst each other. Hey, what are you dealing with? Oh, yeah, I'm dealing with this thing too.

How'd you figure that out? Okay, cool. Let me try that. You know.

[00:46:16 - 00:46:27]

Host: Yeah, yeah. How much does your operational experience inform what you do? To the extent that you guys got some. The truck driving in the middle of the night and otherwise.

[00:46:28 - 00:47:17]

Guest A: Yeah, I mean, I think those are, those are. You have to have those. Like, I don't, I don't know that I could just take myself and drop myself into today without having learned some of those things along the way to like, feel the pain of what it was to go do this, that or the other. I think the last time we chatted, I kind of left with this thought about if you're not willing to do the thing, don't buy the business, whatever that business is.

And his primary service. I still think that's true. And starting there is an important step in the journey. So just jumping straight from, from.

I want to buy a business, to owning multiple businesses without ever having a seat, direct seat in that. I don't know. That seems, that seems like it'd be a lot more difficult honestly. So a lot of those lessons learned in doing a lot of this stuff that's absolutely informed things that we're doing today for sure.

[00:47:17 - 00:47:40]

Host: Yeah. Yeah. Well and I agree with that from my, you know, my position here on the sidelines. But I, and you know, I think some, some people don't want to believe that because they're impatient to, you know, have just accumulate revenue or, and, or they don't want to get their hands dirty because they don't like operations.

Which, which I get.

[00:47:40 - 00:48:24]

Guest A: Yeah. So that, that is to me when I see people who talk about buying a business that is the wrong reason to buy a business is because you want to just make more money quickly. Of, of all the reasons. And actually I'm finding that if making money becomes the focus, like it actually almost feels harder, you know, and uh, just getting better and doing things better act the money almost turns into a byproduct of that like just being good, being a good operator, owning a good company, figuring out how to make it better.

I, I don't know. The more we've tried to unpack, like how do we, how do we turn revenue on in this business quicker or how do we go after this channel quicker? That's actually made it more difficult. I, I don't know, I don't know how to describe that more than that.

But that's just what we.

[00:48:24 - 00:48:43]

Host: Well I have to say if that's true and generalizable, then that is a happy commentary on capitalism broadly that just like delivering good service, that financial reward is the consequence of that, not the point of it. That's how we want things to work in an ideal world.

[00:48:43 - 00:48:48]

Guest A: Yeah. There's a book called Small Giants. Bo Birlingham. I don't know if you've ever read that.

[00:48:48 - 00:48:49]

Host: Yeah, I do.

[00:48:49 - 00:49:00]

Guest A: Yes, excellent recently book on that topic of like hey, just be really, really good. Figure out a way to be excellent at whatever it is you do and, and the money's going to come instead of just chasing the money and chasing. Being bigger.

[00:49:01 - 00:49:01]

Host: Yeah.

[00:49:01 - 00:49:01]

Guest A: Yeah.

[00:49:02 - 00:49:12]

Host: Well Colin, this is going to sound like I'm speaking out of both sides of my mouth here. We are talking about, you know, not being too bottom line focused and, and patience and being so on.

[00:49:12 - 00:49:12]

Guest A: Come on.

[00:49:12 - 00:49:31]

Host: Yeah, but, but so the, so the question for you Colin, is what in along this journey starting in 2018 is. Are. Do are there years in there or decisions in there that really set you back that where you could have been, where you are today a few years earlier. Just.

Can we, can, can we learn from some wrong turns you took?

[00:49:31 - 00:51:41]

Guest A: Yeah, absolutely. There are investments that we made that we could have been a little more patient with that turned out to be complete zeros. Like we, we, too early in the process took our denim and flannel business and said, hey, we're going to try and jam an ERP in here. And we've actually made two ERP decisions too early in the, in that process, partly because we're both manufacturing.

We have multiple brick and mortar stores, we got a distribution center. I mean, it's just a lot. So we needed these things to talk to each other. So we've probably lost at least six figure, maybe multiple six figures over many years in trying to make that decision without putting our full weight behind it.

We've made bad acquisitions. I mean, we've got duds. We haven't. We're not 17 for 17.

So we've bought a business where one business we bought, you know, had over a million or one brand that we bought had over a million dollars in revenue and, you know, had some exposure to Amazon. And just with changes in that from COVID that business ultimately went to zero. Doesn't mean it didn't turn out some cash along the way. But I mean, it was, it was a dud for sure.

We bought a company that, you know, had some changes in how they were marketing before we bought it. And we came in and we moved the website from an old dated look and feel to something that looked and felt newer. And we took our hands off that project and let an individual run with it. And that business cratered.

I mean, revenue was down like, I don't know, maybe 70% from the time that we bought it. And it's still alive today partly because we have the machine that we have, but we're not batting 100% here in what we own and what we do. Even the Montessori thing, it was the less than $500,000 in revenue. And some people would look at that and be like, man, how could you even justify owning something like that?

But we put a dollar into it and probably got three bucks out of it in dividends and the sale proceeds at the time that we were done. So it was a nice little outcome for something that didn't require. Require a ton of time and attention.

[00:51:41 - 00:51:49]

Host: Just got you for a couple more minutes. So we're going to go through these last ones quickly. Tell us about the insurance business, which I think is your most recent acquisition and one you're pretty excited about.

[00:51:49 - 00:55:07]

Guest A: Yeah, we bought this company in, I think we closed March 20th of 2026. So very, very recent. This was a seller, husband, wife team that found us through a podcast, actually heard our story locally here in Indianapolis. They're local, really liked what we were doing and who we were and maybe just connecting with the person.

And side note, I do believe that I can't remember where I heard someone say this. There might be something to building a megaphone. If you're trying to buy companies, put your name out there and share your story and share some personal background. So they heard our story, they reached out, we hit it off, we met them in person, had a great conversation and it was a gem of a business.

We were thrilled to have it. And two key employees wanted to co invest and be part owners of that business, which was excellent because they had that hedgehog expertise in that industry. We still wanted to have someone to be the person at the top, the leader of that business. And along the way as we were doing our diligence, a friend introduced me to a self funded searcher.

So this is a guy who's also local here in Indy and he's a phenomenal person, like way, way higher caliber operator than I could ever be. And he had a great background in running some businesses and was done with that, had just moved back to Indy from running a business for a private equity firm. And he said, you know, I'm just going to use the sba, take my own money and go find something to buy and run and kind of optimize for controlling his time and his flexibility a little bit more. Those were his goals personally.

So we became fast friends with this guy and said, hey, why don't you. He was like literally days away from paying for like a buy side search service provider, you know, like, hey, go out and find a business for me, here's a retainer. And we said, hey, don't do that. Why don't you take a look at this thing with us and maybe we can do it together.

And so we did that and we closed on that. So I think we own maybe just shy of 60% of that company, made room for some key employees in this person and now we co own it together. And it took, you know, we had to craft an operating agreement and some of those other governing rules and stuff. But I mean it's an amazing outcome.

And he gets paid as a CEO and he's running the business. It's been generally hands off for us and he's got total autonomy to run it. So, you know, it's kind of created this idea of, hey, maybe there's this path of finding and partnering with searchers who have operational expertise, but maybe either can't find a business to buy or don't quite know how to put it together, or maybe they don't want to extend their personal balance sheet and then doing it together and say, hey, we don't have to own 100% of this thing. So anyway, that's how that deal came to be.

It's a professional services business, so it's much higher margin, much more cash generative than anything that we've owned to date. So I'm hoping this is our engine that can feed more deals in the future. Unlike our consumer business which just it consumes cash to continue growing. So I like it on multiple levels here.

[00:55:07 - 00:55:42]

Host: Yeah, well, Colin, I certainly like the model of Searcher who didn't buy their own business, but wanted to, but was also open to running the business for another acquisition entrepreneur. So I mean the whole our Smith List website is based around that concept. We've talked about it a lot here on the. On acquiring minds, but I will.

Having said all that, I do wonder why. Sounds like he was a great fit. But why? What?

Why is the Searcher profile better than just somebody from industry going out and having a headhunter find somebody from industry to run your businesses?

[00:55:42 - 00:56:18]

Guest A: I think you want someone who's got that mentality of I'm going to put my dollars on the line and like go out and do this right and kind of risk, risk everything, so to speak. I mean, he wanted to go get a big SBA loan and buy a business and was, was sort of comfortable taking that personal financial risk that came with it. And so, you know, not to say that someone in an industry doesn't have that, but like to me, the person who wants to become a business owner and they're willing to throw whatever it takes into that, into that arena. I don't know, it's just a different caliber of mindset.

Right.

[00:56:18 - 00:56:21]

Host: It's demonstrating the entrepreneurial kind of.

[00:56:21 - 00:57:26]

Guest A: That's right. I don't have all of these jobs, but it's my job to go figure all of them out. Right. And just because I don't know how to XYZ like, doesn't mean I can't go solve it.

And I mean, Joe and I have had to learn tons of different things along the way. And you want someone who's Going to like approach it that way. I'm going to learn whatever it takes to go figure out how to solve this thing. So yeah, I think you want that scrappy entrepreneur, business owner mindset in that seat.

Yeah, yeah. And I, you know, some of the searcher. Wow. I don't want to paint with a broad brush, but many of them have, have excellent operational skills and maybe they just struggle in finding a good business or they're trying to check off too many items on the checklist and so they'll never pull the trigger.

And it's like, well, hey, if we can provide that piece of it and we know how to put a balance sheet together, which isn't the easiest thing on the planet either, then why don't you jump into that seat, share the economics. And it can be economics that are just as good, if not better than the traditional search fund path. And oh, by the way, we're pretty hands off, easy to work with folks. Right.

And we got people you can talk to just to ask and figure that out.

[00:57:27 - 00:57:27]

Host: Absolutely.

[00:57:28 - 00:57:33]

Guest A: So it's early. I mean this isn't like the model to date, but we would hands down do more of that if we could.

[00:57:33 - 00:57:35]

Host: Sorry, did you say it was an SBA acquisition?

[00:57:35 - 00:57:37]

Guest A: This was not. No, not.

[00:57:37 - 00:57:39]

Host: Okay. Okay. So he doesn't carry a personal guarantee.

[00:57:39 - 00:57:43]

Guest A: He does. He does not carry a personal guarantee. No. Okay, okay.

[00:57:43 - 00:57:48]

Host: Which is by the way, another perk of this model for the searcher. No, seriously?

[00:57:48 - 00:57:49]

Guest A: Absolutely.

[00:57:49 - 00:57:50]

Host: Yeah, yeah.

[00:57:50 - 00:57:54]

Guest A: It's a deal breaker for. I think that's the biggest piece of it. Right. It can be.

Yeah, yeah.

[00:57:56 - 00:58:29]

Host: Colin, you so hearing about this sort of operator model. Okay. We just talked about. Granted it's a little bit more entrepreneurial, searchers and so on, but in some ways it is similar to the private equity model by businesses put in management.

You have a portfolio here of businesses you are not. I haven't heard the word permanent. Maybe I just haven't given you the opportunity to say it. But you do, you do talk about them having terminal value.

So obviously you're going to exit them at some point. Are you private equity?

[00:58:30 - 00:59:56]

Guest A: No, no, no, no, no, no, no. I don't think, I don't think you could get a deal done if you tell someone you're private equity anymore. Right. I think we, if you put on a spectrum, you got private equity on one end and maybe Berkshire on the other or family offices on the other.

We're probably, I know it's cliche and some whatever you can come at me. I would say we're More of a Berkshire, like, that is the, that is, the plan is to buy stuff and then hold it for theoretically ever. Right. And just let it keep going to work.

And ideally these are good enough businesses where like, yeah, I do want to own that for a long, long, long, long time. We've sold things along the way and I, I like to tell myself that there were reasons that we exited those, like they were, had some rationality to them, like this thing was just too small. We sort of outgrew it being the best fit for us. Trucking business, like, just did not make sense for health reasons and many others to continue running that.

So there were, there were reasons that we've exited the things that we've done. But I love everything that we own today. Like, I don't think there's any, any line of sight to say, hey, let's build this up and sell it in three, five, seven years. So part of it is just playing the game and loving playing that game.

And I think there's a chance that we'll get into some stuff in the public markets at some point in time and take the things we've learned into some smaller companies there. And so, yeah, I will say it's maybe more of a blend of a Berkshire than, than what we had originally managed or intended.

[00:59:56 - 01:00:03]

Host: When you talk to sellers owners, do you say explicitly that your intention is not to then sell their business?

[01:00:03 - 01:00:41]

Guest A: Yeah, I think when we tell people and we introduce ourselves, we say, hey, we're, we're buying businesses. We're trying to build a Berkshire and collect great businesses and put people in charge that are excellent people to run them. Like, that's our message, you know, And I think, you know, when Berkshire, when they buy companies, they typically say, hey, management's gotta come because we're not gonna supply it. I mean, I think that's probably a key difference for us.

Well, one, we're going to borrow money because we sort of need to. Right. We're limited by how much capital we generate. And then two, we generally usually it's like a husband, wife, team or seller that's retiring or exiting.

So we do wind up replacing management and finding that person and partnering with that person is important part of the process.

[01:00:42 - 01:01:04]

Host: Good stuff. Colin, great to have you back. Exciting what you're building. I was so glad we got to reconnect and share your progress these last two years with the audience.

I'm sure they'll be, they'll be eager to hear it. So thank you. Sir, what's your email? Or if that's not the best way to get in touch with you.

We can put your LinkedIn, but I suspect there could be some people who are interested in talking to you more about running one of your companies.

[01:01:04 - 01:01:22]

Guest A: Absolutely. And I'm always happy to chat with people who are in the space or interested in the space. My email is Colin C o L I N@circlecitycapitalgroup.com We've got a website too. Just circlecitycapitalgroup.com I think there's like a contact form or something on there too, if that's easier for folks.

[01:01:23 - 01:01:31]

Host: We heard you say indy earlier, but I don't think I made it clear that Circle City is a nickname for Indianapolis. So this is where the magic is happening.

[01:01:31 - 01:01:34]

Guest A: That is where the magic has happened. If you're ever in town, hit me up. Yeah?

[01:01:34 - 01:01:36]

Host: Great, Colin. Thank you, sir.

[01:01:36 - 01:01:37]

Guest A: Thanks, Will.

[01:01:38 - 01:02:22]

Host: Hope you enjoyed that interview. Don't forget to subscribe to the Acquiring Minds newsletter. We send an email for every episode with an introduction to the interview, a link to the video version on YouTube, and soon, key takeaways, numbers and more essentials from the interview. For those of you who don't have time to listen or watch it, subscribe at acquiringminds.co.

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