Introduction
Today, I’m sharing my conversation with Evan Stewart, who successfully acquired and transformed a legacy printing business into a thriving operation. After completing the Acquisition Lab program, Evan purchased Direct One in April 2023 and grew its EBITDA from $1.8 million to $3.2 million in just two years. His journey offers valuable insights for anyone looking to buy legacy business in a challenging but evolving industry.
Founder Success Story QnA
What was it that turned your attention to buying a business in the first place?
Yeah, you know, I think when we met, that was kind of the middle of my search probably or at least the end of the beginning, right, where I started to get very intentional about that. Not going to say I was always thinking of buying a business, but I think if you went back and pulled my high school classmates, they’d probably say I was one of the most likely to do so. I was just always a current events guy, like I always knew what was happening in the world, sports, politics, whatever. And so it was just always involved, right, and in the Zeitgeist, so to speak.
Evan, going back to the business buyer fit process for you. So you went through the lab and that kind of helped crystallize your thinking a little bit. You hear from the loan broker that lenders are likely to give lend you more money if you buy a business in an area that you’ve been active in before, namely printing. But what about your sense of your own distaste for this industry? Were you just gonna power through that or did you realize that maybe there was an angle to this industry that you could enjoy?
I think through that soul-searching process, I found that maybe I felt like I wasn’t necessarily creating a ton of value as an individual because everything we do is services based, right? But on the print side, this is tangible. You can feel it like it’s a manufacturing environment. And that got me excited. And it took a while to understand that was really the real issue. I couldn’t actually see or feel what we were doing. You reflected back and realized what you didn’t like was the non-tangibleness of kind of services work. Yes. But something tangible did turn you on. And commercial printing is nothing if not producing pieces of paper that you can touch. That’s it. It’s ink and paper.
So what about this business? Tell us about it. Direct One.
Direct One is a commercial print and direct mail services firm. It’s been around since 1998 where it started in a garage and by the time I got to it in April of 23 it was 75 employees, two facilities that kind of right next to each other based in Winter Park. We have about 60,000 square ft. And this year we’re going to do anywhere from 110 to 130 million pieces of mail. Just kind of depends if some things we have in the pipeline hit. Next year if we continue our growth I think we’re going to hit that 150 million mark. So we were on the rise.
And tell us about the other numbers of the business that we’ll all recognize. Revenue, number of employees, EBITDA, etc.
So, when I bought they’re doing I think we’re at $34 million in revenue, 1.8 million in EBITDA. In that $34 million number that includes postage, right? So your postage is going to be significant amount sometimes 50% of the cost of a project, right? And that is pass through. You’re not able to mark that up. So on a $34 million number, let’s just call it back of the envelope, 50% of that is postage. Your real top line is more like 17. So that 1.8 million on 15 is so those margins aren’t as thin as they seem. It’s between 10 and 15%. A little bit higher, but if you’re operating the business, you’re not necessarily getting that capital out, you know, prepayments. It’s not getting out ahead of time. So a lot of times you’re floating that postage. So it’s very important. You have to keep that in mind. Like your services revenues, you’re looking at 15-17 million, but that money is flowing through you in a lot of instances, you’re fronting it.
How consistent had that revenue been? Talk to us about how you perceive the quality of revenue in the business.
Very very consistent, let’s say. In 2019, they had merged with a competitor. This is how they ended up with two facilities, right? 2019, they had merged with a competitor right across the street. Just so happened that way. So the company doubled in size overnight this was probably mid to late 2019 and then of course you had COVID hit in 2020, everyone goes home so it’s a little bit chaotic from there. Then right after that once COVID’s done you had the great paper shortage of 2021-2022 which again affected industry margins across the board. So from the merger on they had never really had a good stable year. They were able to actually manage things or see and benchmark. So that kind of threw a little bit of kink in things. But overall like between the two companies you had clients that had been here for 10 years. The first client that they started the business with actually had been here for 30 years, had never left. So you have a good strong stable client base and the company itself, the two owners, one had been here since the beginning. They had seen it all. They were in more of a we’re not really that interested in growth mode. Let’s just kind of we’re happy. We’re happy with where we are in life. It’s a good business we have. We have our 70 employees. We take care of them and their families.
You took this opportunity to the Acquisition Lab search forum where members can bring live deals they’re looking at. I recall you telling me that you took this there and got Walker’s opinion on it. What did he say?
He didn’t say not to do it. It was just more like he had some really good questions. And he admitted I think his first purchase was in the print industry. And it was probably right around the time of the financial crisis. So, I think he had some battle scars there. But sort of the same things we’re talking about now, like it’s a very tough industry. There’s a lot of capex. You have to do a lot of fronting, with your paper, postage. So it’s tough. You want to make sure that what you’re buying is legit and it is solid.
How did you structure the deal?
We settled on a 4x multiple which in all honesty was probably a little high for this industry as we’ve discussed some of the challenges. But I had looked at enough businesses and I started to view things differently. I’m not going to get into a battle over a couple hundred thousand if this business is a great fit for me. And I felt in my guts that this was something I could definitely do, I could add value to and we should go for it. So we settled on the 4x multiple 1.8. So it ended up being 7.2 million.
How did you navigate the transition from Jacksonville to Orlando for the business?
Day one, we go in and we do the speech on the floor transition and I got 70-some employees and they’re all kind of looking at me like who’s this guy, right? I ended the speech with something along the lines of we’re going to grow. We’re driving back to Jacksonville that day, me and my wife and we’re in the car and it’s like a lot of silence and I just remember looking over at her. I’m like, what did we do? You know, it’s true now. We burned the boats. But that was the first like real like, oh wait, this is real. Like we’re not in search mode anymore. I’m not out here flying out trying to tour a facility, doing diligence, doing phone calls. Like this is real. Our whole lives are mortgaged now and this has got to be a success. Early on we had discussed we didn’t want to pull the kids out of their daycare yet. I know this sounds dumb now, but they had a good preschool. My wife had her job. Was working mostly remote, but the office was there in Jacksonville. It was March, April, and we didn’t want to uproot everything. So I was just going to go down three, four days a week and stay at an Airbnb initially, but ended up finding like a long-term apartment rental, I think usually for travel nurses. We did this for probably about two months. And we probably fought more in those two or three months than we had the entire years of our marriage. We pretty quickly realized that like this is not going to work. Like we need to get down there. So we contact a realtor, put the house on the market, start that process. We head down to Orlando, we find a place we could rent for like 6 months. Couple months later, we finally sell the house.
What was the culture like when you took over?
Culture you found is you had a successful company, mostly the same clients that they had had for years, not a lot of new clients, an employee base with very long tenure, not a lot of turnover. Generally happy, right? Pretty content with things. You also had several that again a consolidating contracting industry. Someone buys a company, strategic player, that sort of thing. They’ll buy another competitor, they’ll come in, they’ll make their promises, ‘things are going to be better,’ and then a couple months later they’re doing layoffs. So you had a few that had been through that. So a lot of skepticism. And then I wasn’t what they were expecting, right? Like I think they’re expecting more along the strategic side of someone from another company, right? That had been in the industry and you’re going to get person in there that has more gray hair than I do. And I was just different, like relatively young.
If you get in there and realize that your understanding of this industry is a lot less than you thought, was there actually business buyer fit?
Man, great question. If I thought going in it was 90%. Let’s say couple months in I’m probably at 60%. But it’s just going to be a lot harder than I thought. This isn’t something where I’m going to come in and flip the switch and replace the fax machine. This is going to be work and it’s going to be work on the human side and then it’s just going to be work in general. Like you just got to roll up your sleeves and just plan on being here as many hours as you possibly can and setting that example.
Did you stabilize the business? Did you retain all the key people?
We did. We had that first year I would say went better than we could have imagined financially. It really did and it could have just been timing, you never know. And some of the things that I wanted to bring on hit. So financially went better than we could have ever imagined. For me growthwise once I got over my little six months of like, man, I’m showing up every day. I’m providing no value. I have no idea what I’m doing. It’s only a matter of time before this gets found out and everyone’s just gonna be like, ‘who is this guy?’ Once I got over that and I just started to dive in and just say, okay, maybe I’m not the smartest person on the direct mail side here or the print side here, but there are other things I can bring to the table and other experiences that a lot of folks, a lot of my leadership team haven’t seen.
Can you put some numbers behind how your first year performed?
We were over two in EBITDA. I want to say 2.2. Services revenue we bought at 15. We hit 16 and 23. Yeah. So we increased revenue. Increased revenue and EBITDA. Costs were held in check. We got through the paper shortage. We were at the tail end of that. And so that definitely helped. There wasn’t paper prices going up every other week with planning. That’s financially where we landed.
How did your wife get more involved in the business?
She had been part of the Fanatics like growth story. She was employee, I don’t even know, but they’re a couple hundred employees at the time when she started to where this year, there were several thousand. At one point during their growth, they had bought a company out of Tampa and they had moved their headquarters there. So throughout the last couple of years before we bought this business, they had been transitioning the employee base out of Jacksonville into Tampa. And so we knew it was really only a matter of time before they would make that ask of her. We went through with the business purchase, gave the day one speech. We went through our troubles those first couple months. Fast forward to September of that first year, 23. She’s actually here at the office, gets a phone call. Long story short, she’s being let go as part of mass reorganization. For us and kind of where we were at that point, there was no hesitation whatsoever was like almost I don’t want to say this lightly, but it was almost like a blessing in a way because she was already super stressed. It was a very demanding job that she had. We had our kids. We’re in a new place. We had this business. It was almost like, okay, that’s a sign. This is what I’m supposed to be doing. All right, you can definitely with your skill set and your experience and your background and just being my support, you can add value here.
How many hours a week does she work in the business?
The kids start going to daycare part-time. They get out at 2:00. They get there at about 8:30, she’ll do the drop off, she’ll do the pickup, right? So she’s able to play mom while the kids also get their socialization with the kids. From the hours of about 9 to 1:45, she’s here, she’s helping, she’s busy, she’s always in, always involved.
Your wife got more involved than just being your support. It’s actually great having her in. Does that work well for your marriage?
It is. I’d say from my perspective marriage wise probably never been stronger. Understanding this does not work for everyone. I get it. Like a lot of people do not want to work with their spouse and I totally understand. But just for us and our dynamic and kind of who we are as people, it works really well.
How does the postage financing work in your business model?
You’ve got two or three different types of customers. Your bigger, larger mailers, like billions of pieces a year, hundreds of million pieces a year type customers. They’re going to have their own permits on record with the USPS. So they’re paying their own postage, right? So typically, you don’t have to worry about them. It’s the 60% of customers, 50% of customers that I mentioned are doing $10,000 or less. Typically they’re going to come to you with a mailing. It’ll be, let’s say, 10,000 6x11s. They’re going to send you a data file of the list of folks that they want to hit and the creative the art piece. You’re going to run it through your data processing system. We’re going to tap into the USPS. We’re going to get the list perfectly sorted so they can get the lowest postage rate possible. Let’s say in this scenario, it’s 32 cents a piece. So, with 10,000, what’s that? $3,200 for postage. For services for something like that to print, to mail it, to get it out, we’re probably going to charge 15 cents a piece, right? So 15 or $1,500. So you can do the math there. Most of that in that job itself, and that’s a very common job for us, is going to be the postage. From there, you have two choices. If it’s someone you never worked with before, you’re going to want to get the money up front for the postage portion and then we’ll bill them for the services, Net30. If it’s someone that you’ve got a history with, then typically you’re going to go ahead and send it out. At the same time, you’re going to send them an invoice and they’ll be either cutting you a check and it’ll get there in a couple days or they’ll AC you within probably 10 days.
What about the capex requirements in this industry?
The equipment here lasts a long time, especially the older mechanical presses, the offset presses. Unfortunately, those were set up to do the million piece runs, right? where you’re just trying to get it as cheap as possible down to the quarter of a penny. That part of the industry is slowly fading away. What’s on the rise is more of this inkjet technology. Really it can be toner based as well but it’s digital variable imaging where it’s a million piece run but every single piece can be a little bit different. Those presses are becoming more the norm. Those presses, you’re talking a million and a half to $3 million, you know, if not higher than that. So it’s not a cheap investment at all. In some instances could be half of what I paid for this company as a whole.
Is that big printer investment necessary to really grow the business?
Absolutely. That’s the direction we’re going. We’re going through that process now. That’s why I was at the Inkjet Summit. I’m just educating myself on as much as I possibly can because it’s the biggest decision we’re going to make as a company over the next couple years, right? And we got to get it right.
Where do you want to take the business? What’s the vision?
The USPS is pushing hard into the same thing we’re talking about. We’re moving more away from a commodity into more of a luxury, which to me means being able to play with different parts of the marketing mix. Whenever I go in now and I’m talking to someone, usually that person is, say, at a Fortune 500 company, that’s a 35 to 45 year old. They understand TikTok, Facebook, Instagram perfectly. I’m actually doing more of an education, a consultative sales job on direct mail and the benefits of it and how it can play along with their strategy. So that’s the way the industry is going. Smaller runs, much more personalized, and getting it there faster, right? Which means next day turns. So we’re going to invest in equipment to make that happen.
How has the culture changed since you took over? Have you gotten everybody excited about your vision?
You probably impossible to get everybody, but we got some key buy-in. It happened pretty early on. Just different things we were doing for the employees. Something as simple as buying pizzas, a couple Fridays, just things like that. And just sort of we started sending out a newsletter. And so we just started to try to establish that hey, we are like you. Like this is still a family business. It is still a family environment. You are more than welcome to bring up your kids, your brother, you know, whoever to let them see where you work, what you do. Because we’re proud of it, right? So we got over that hurdle pretty early on. And then there never was a mass firing. I didn’t come in one day and say ‘you’re not meeting what we want.’ We just kind of let it play out a little bit. And some of the folks that didn’t want to be a part of this, you could count it on one hand, and today we have 84 employees. The ones that didn’t really want to be a part of this where we’re going, they basically opted out themselves.
Where are you today in terms of revenue and EBITDA?
At the end of last year 24 we did I want to say 18.7 million in services revenue, 42 million total topline revenue. And we’re over three probably about 3.2 in EBITDA. This is a really good year. With this business like there is a ton of operational leverage. Fixed costs are the fixed costs and so anything you can do over a certain number each month like it’s going to really impact the bottom line.
Anything we didn’t get to that you wanted to share?
For any searchers out there that is kind of wobbling, thinking, should I do it, should I not, do it 100% do it. If you feel in your gut that this is what you need to do, do it. Don’t get caught up on multiples and EBITDA kind of variation. Go down there, meet with the owners, meet as many people on the team as you possibly can within reason. Don’t give it all away. Tour the facilities, understand it, feel it, and if you feel like it’s right for you, then make it happen. Don’t get caught up with, well, they want a couple hundred thousand more than what I want. Who cares? If you can bring the value to the company, do it right. You got to find the right business for you. Be persistent. Be deliberate. If you’re talking to someone, let’s say a business owner, it’s just not going to work. Quit wasting their time. Move on. You only have so much time to do these things. So be deliberate about your actions. And then always focus on the big picture. Remember your why. Whenever I go home, see the kids. To me, it’s all at the end of a hard day, like, okay, this is why I did that, cuz I want to give them a better life. And I want them to see me as an example of, hey, if you work hard, you follow your dreams, you take calculated risk, which in my opinion is what America is really all about, then you can be successful.
Evan Stewart Business Stats
Evan Stewart transformed Direct One, a legacy print and direct mail business, into a high-performing operation within just two years. Here’s a breakdown of how the business has evolved under his leadership, showing remarkable growth in both revenue and profitability metrics.
- Acquired Direct One in April 2023 with 75 employees and 2 facilities
- Grew company to 84 employees within two years of acquisition
- Increased EBITDA from $1.8 million to $3.2 million in 24 months
- Grew total revenue from $34 million to $42 million annually
- Maintained exceptional client retention with minimal turnover
- Handled 110-130 million mail pieces annually with growth trajectory
| Metric | At Acquisition (2023) | Current (2025) |
|---|---|---|
| Employees | 75 | 84 |
| Annual Services Revenue | $15 million | $18.7 million |
| Total Revenue (incl. postage) | $34 million | $42 million |
| EBITDA | $1.8 million | $3.2 million |
| Mail Volume | 100 million pieces | 130 million pieces |
Evan Stewart Strategic Method
Evan implemented a strategic approach that focused on evolving a legacy print business while respecting its established foundation. His method combined operational improvements with cultural transformation to drive significant growth in what many consider a declining industry. Here’s how Evan successfully executed his buy legacy business strategy:
- Leveraged his industry experience to identify value creation opportunities in print operations
- Replaced outdated ERP systems while maintaining operational continuity
- Invested in digital variable imaging technology to modernize print capabilities
- Integrated direct mail with digital marketing strategies for clients
- Developed Direct Collect, an in-house pledge processing system
- Transitioned from commodity printing to premium, personalized mail services
- Maintained employee stability while creating growth pathways for leadership
Evan Stewart Tools
Evan’s successful business transformation relied on strategic technology adoption alongside human-centered relationship building. He carefully selected tools that complemented his team’s expertise while modernizing operations for growth. Rather than forcing disruptive change, Evan implemented systems that empowered his experienced workforce to deliver enhanced value to customers.
- Replaced legacy 1990s-era ERP system that couldn’t calculate average run rates
- Implemented paper tracking system to manage 60,000 sq ft of production space
- Deployed USPS integration technology for optimal mailing route sorting
- Introduced read-and-print camera systems ($70,000 each) to prevent mailing errors
- Leveraged personal relationships with political campaign networks for client acquisition
- Created internal newsletter to build transparency and team engagement
- Developed Direct Collect software to automate donation processing
Key Notes
This case study demonstrates several critical insights about turning around legacy businesses in declining industries. Evan’s journey shows that with the right approach, even ‘old economy’ businesses can achieve remarkable growth through strategic modernization.
- Business buyer fit is crucial – Evan’s political campaign background created natural client connections
- Legacy businesses often have hidden value in established client relationships and processes
- Cultural transformation must precede growth initiatives in legacy organizations
- Moving from commodity to premium services is essential for margin improvement
- Employee retention is critical – turnover costs far exceed retention investment
- Family involvement can strengthen business commitment when roles are clearly defined
- Timing matters – election cycles provided natural growth opportunity for direct mail
Get Started in Just 5 Steps
Whether you’re considering how to buy legacy business or transform an existing operation, Evan’s approach provides a proven blueprint. Follow these five steps to begin your own successful business acquisition and transformation journey:
- Identify industries where you have natural business buyer fit and can demonstrate expertise to lenders
- Focus on the human transition first – prioritize employee retention and cultural integration
- Modernize technology incrementally using legacy staff knowledge as your guide
- Build value through service integration rather than competing on price as a commodity
- Target specific market trends (like election cycles for direct mail) to accelerate growth
Conclusion
Evan Stewart’s success with Direct One proves that legacy businesses in seemingly declining industries can achieve remarkable growth with the right strategy. By focusing on business buyer fit, respecting existing culture while driving innovation, and moving from commodity positioning to premium service offerings, Evan nearly doubled EBITDA in just 24 months. For anyone considering how to buy legacy business, his journey demonstrates that with the right approach, even ‘old economy’ companies can thrive. The key is finding that perfect intersection of personal expertise, market opportunity, and operational improvement – then committing fully to the long-term transformation process.