Introduction
how one couple bought two businesses is more than just a catchy title—it’s the remarkable journey of Lindsey Buckheit and Kevin Black, who successfully acquired two distinct businesses simultaneously. After years in corporate roles, this couple navigated the complex world of business acquisition, overcoming common pitfalls like part-time searching, deal box confusion, and lender rejections. Their strategic approach to mitigating key risks, structuring seller financing, and leveraging complementary skills offers valuable insights for aspiring business buyers.
Founder Success Story QnA
Lindsay, Kevin, where? Why? How did you first get the inkling that you might want to buy a business?
We both spent the majority of our careers in the corporate world. Lindsay, I guess, really spent her whole career in the corporate world. I spent the majority of mine in corporate sales roles. We were both ready for a change. We were both looking to get out of the corporate world. Lindsay was looking to get out of her corporate role. We stumbled across people talking about exiting the W2 world through entrepreneurship through acquisition. It was appealing—the idea of having more ownership over our direction, our ability to earn. It started as a way to get Lindsay out of her corporate role. We joined a community together, initially I was supporting my wife, but quickly fell in love with the idea. It was that control over the outcome of our life, the direction, being able to work towards financial freedom that was really appealing for both of us.
Why did you choose buy a business and what was your progression from acquisition curious to acquisition serious?
I love that. That really effective targeting caught me on Instagram. It was Cody Sanchez contrarian thinking. It was exactly what I was looking for when I had already tried side gigs, side hustles, real estate. None of those fit where we were or how quickly I wanted to make a change. Little did I know at the time that it wouldn’t be quick acquiring either, but we joined the community in May of 2023. We spent about 8 months in the community, learned the basics of what this thing is, how people do this, success stories, horror stories. Eight months into our year membership, we were not any closer to buying a business. We were both still working full-time and didn’t have time to do the amount of calls needed.
When did you become “we” in this acquisition journey?
I joined the community with Lindsay up front. It was always going to be “we’re going to do this together.” We’re looking for a business for Lindsay to own—this is our way of getting Lindsay out of the corporate world. It started feeling attractive to me within a month or so, but it wasn’t clear what that would look like. We started with it being more of “if we found the right business that could use my skill set (background in sales) and support both of us, then I would leave. If not, I would support as a side gig and Lindsay would own and operate the business.” It wasn’t until later that the two businesses came to fruition.
Your eight months of learning felt like you were no closer to buying a business. Was that simply because you were part-time searchers?
That was a big part of it—time and effort. But it was also that because of how long it took to get something on the hook, I tried to make everything work instead of focusing on deals that actually worked. It became easy to try to fit square pegs into round holes because you’re desperate to find something that could get to the next stage. I ended up spending time on deals I never should have been looking at. I didn’t have the discipline needed to only look at things that fit the deal box. We knew the type of cash flow we were looking for, location, etc., but in conversations, I kept trying to see myself in the business rather than “does the business work for me?” I’m a problem solver—I was always going to try to find a way to make it work. I needed guidance.
What did you do to overcome this frustration?
In December, I started to freak out because eight months in, four months left. The community is an annual membership. I asked around and sensed other people encountered similar wheel spinning. The unbiased lens is what I needed. I needed someone to tell me “don’t look at that. That doesn’t fit and here’s why.” Instead of “this is the first deal I found in 3 weeks that is a maybe—I should put everything into it.” We did regular meetups in Austin with other searchers and met Athena Simpson, who runs Aquamatch. She talked to us about connecting searchers with dream businesses. At first I was like “I’ve got it, it’s fine.” By December it was clear we weren’t going to get there with what we were doing.
How did you seek to solve this problem?
We started working with her and her team in January of 2024. Pretty immediately saw traction. The first thing we did was calibrate what really is our deal box and stress test it. By April we had our first write-up. We looked at a few businesses between February and April, maybe five or six, and in April, we were introduced to the agency we ultimately acquired. Started working with her in January; by April, we had the business in front of us.
What did working with Aquamatch do differently that helped you?
They started searching on our behalf, but also the deal box refinement. For searchers who think they have a deal box but it’s poorly defined—what was different is they took about a month to get to know us and sent us deals to say “yes, no, and why.” Through that calibration period, they learned things like “you’re okay with businesses a certain number of miles outside of Austin, but realistically given what you want your day-to-day to feel like, you can’t own a business in another state.” It was things I wasn’t telling myself—I’d think “I could do that, I could make it work, I could fly there once a month.” But when someone else presented it, it was easy to say “I don’t want to do that.” An accountability partner helps me—it’s that mirror of “hey, you really going to do this?” If so, let’s move ahead. If not, stop looking at anything that checks that box.
How is narrowing down criteria going to actually yield more deal flow when you’re struggling with deal flow?
Even to this day, we weren’t looking for a particular industry. I’m still very open to many different industries. It’s not that the standard deal box categories needed to get smaller—I didn’t need to pick three industries. It was that within the industries I was interested in, the conversations needed to be more targeted to who I would be as an owner. What is the current culture I’m walking into? What’s the hierarchy like? How many employees? How long have they been there? Do they know you’re selling? It’s like trying to interview for a company without asking about culture—you’d never do that unless you were desperate. It’s more about the intangibles that sell a deal than what is the SDE and where is it located. It’s what it’s actually going to feel like and whether you’ll be able to fight for it to close and deal with it after. If I don’t love what it does now or see the path to make it better, I’m back on that hamster wheel.
Pick up the story—how did the acquisition process unfold after April?
We were introduced to the broker in April. We had a pretty immediate good relationship with the broker and sellers when we sat down face-to-face. We had a signed LOI in June—we took time to negotiate specifics. Then we went into securing funding, which took a little bit—we went through six or seven banks to find a lender.
Tell us about the first business you acquired.
It’s an ad agency out of San Antonio. SDE was about $575,000. Purchase price was $1.6M. We had a pretty sizable seller note to help with downside risk. We did about $1.2M in revenue in 2023. The biggest thing was the cash flow health—our original threshold was $350K, so this was totally worth talking to them for. I liked that it had employees staying with the business. It was close to the consultative client approach I’d done for years. There was no creative involved—it was purely media buying. It’s making purchases and placing ads for various clients. It wasn’t obvious how it might fit, but the option to go fully remote was attractive. With such healthy cash flow, it could support both of us. My background was aligned with a marketing world—I’d been selling PR marketing software, working with similar clients.
Explain how this media buying agency operates without creative services.
We work really closely with a couple of creative agencies—very closely. We’ll farm out the creative side to them when needed, and they’ll farm out the media buying portion to us. It’s kind of a symbiotic relationship where we can bring clients to each other. It’s also not as transactional as it sounds—our clients have annual plans with us, so it’s the overall media purchasing strategy with a book of clients that we plug and collaborate with the creative agencies on.
How did you structure the deal for the ad agency?
We acquired it for $1.6M. We have $576,000 in a seller note—three seller notes. We split the equity injection with them—5% equity injection they’re carrying. And about 31% of the total purchase price as a forgivable note, broken into two parts. The first note is a third of the total forgivable note based on performance months 1-12 from close. The remaining 2/3 is based on performance from 12-24 months from close.
What are you measuring performance-wise exactly?
Gross profit. Part of the risk of this business is we’re buying the transfer of relationships. There aren’t annual contracts with these clients—it’s standard in this business. It would be hard to know if a client continues at the historical level until we get to that one-year mark. The sellers were still pretty engaged with the business, so there was risk they’d continue doing business with us without it being a decision to do business with me long term. We wanted to protect ourselves if larger clients walked away in the second year. Gross profit is the proxy for a client leaving.
Why trunch the forgiveness into two years instead of one measurement at month 24?
There was client concentration in this business—that was another risk we were mitigating. If that one client left, we wouldn’t be okay in year two. Tying it to one client felt more risky because of that concentration. It made more sense to just keep revenue and gross profit where it is. It gave more flexibility—if one client spent less, they’d help us bring in new ones. If the large client spent less, we could get others to spend more. It made it much more flexible to solve the problem. We also had them in our contract for up to 12 months—if they worked with us through that mark, renewals were still based on their presence.
How did you arrive at the 31% number for the forgivable note?
We used the SMB law modeling that Aquamatch tweaked to put in the equity injection as a separate note so we could play with if they do 5% or 7.5% and this much forgivable. We did all the downside modeling—we played with if we did X in a forgivable note and lost 10% in revenue in year one—would the lights still be on? Could we still cover debt? We figured out what our floor was and what we could go up to make that seller note bigger. The $1.6M was actually over asking to incentivize them to take on a bigger note. We did all the modeling to ensure those numbers worked in our favor. Getting them to carry a bigger note ensured both were incentivized toward the business’s success—we were happy to pay a little more.
How did you assess the quality of revenue for this agency?
This agency isn’t purely digital—it has a traditional buying side. Many digital agencies don’t do their own traditional media buys, so they sometimes need to bring in another agency for billboards or TV or radio. It’s also a very old agency—been around for 15 years, very well established in the market with a strong reputation. That’s already served us well in the 6 months we’ve taken over.
What is the business model for the revenue generation?
In traditional media buying agencies, there’s usually a commission on total ad dollars a client spends. Similarly in digital—you have a markup on digital ad inventory. If you spend $100,000 for Instagram ads for a client, you’ll mark that up 10%—so on a $100,000 ad purchase, you make $10,000 in revenue. That gross profit number is what the agency keeps after media buys.
How did you convince lenders to finance the deal?
This was a particularly tough process—I went through several lenders. There were clear risks with this business that didn’t fit many banks’ deal boxes. Every business has risk—all deals have risk. Part of the game is finding a business that aligns with your risk appetite and skill set because you have to fiercely defend it. If you’re not comfortable with it and can’t sell it, you’ll never get through the process. As long as you know the risk factors and can talk about them, that’s half the battle. We ultimately worked with Matias Smith at Pioneer Capital who helped us find lenders who were a good fit—huge resource through the lending process.
What risks did banks identify that we haven’t discussed yet?
Keyman risk. With any agency, some banks immediately say no because they consider the people at the helm as the creatives (ironic since this agency doesn’t do creative)—they mean they’re the expertise. There was keyman risk, client concentration, and this being the transfer of relationships. For us, we felt positioned to manage those because of our backgrounds in sales and account management—transferring relationships was something I’d done very well for a long time.
When speaking with banks that didn’t want to do the deal, had you finalized your protective deal structure yet?
It evolved through the lending process. It wasn’t quite where we landed—there was always going to be some forgivable seller note component, but it wasn’t as large or structured over 2 years initially. We got better at defending it every time.
When did the business become “yours,” Kevin?
After we were in the process of getting lending, we still had our deal flow on with Aquamatch. In early August, we were about to get our commitment letter and were introduced to the second business. That’s when we started conversations about “can we do two?” We made the switch just before getting the commitment letter in August, and closed the agency October 4th.
What was the second business all about?
This is a small business in Austin—immediately a selling point. Competition in Austin is tough. It’s an outdoor residential design and build—we lean more toward design and construction, not horticulture specialists. We do hardscapes and softscapes—things like outdoor kitchens, pergolas, pools. The build is subcontracted out; design is done in-house. The business was just the seller and his wife running everything—he was the design architect, project manager, foreman, client communication, admin. His wife supported in day-to-day and site visits.
How did you wrap your head around buying what sounded like a one-and-a-half person business?
When we were struggling with the lending process and realizing the risks for the agency, it became clearer how much Kevin’s skill set was better fit for that. When this second business came along, I realized what was missing from the agency deal for me—the tangible piece. I like to build, to see something go from nothing to something. I have experience in that. Part of why working with someone to show you your mirror helped—I liked that the agency didn’t have creative, but over time I realized I thrive on seeing something being built, digital or otherwise. I don’t have construction experience, but grew up around it—my dad had a repair and remodel business. When I spoke with the seller about challenges and his day-to-day, he admitted he’s a procrastinator who can’t delegate. I realized “I know how to handle both of those things very well—I’ve been a product manager for years.” His biggest challenge was the very thing I do all the time.
How did you address the key man risk in this business?
Part of the agreement was he’d stay on through 6 months—design capacity and showing me how it works, introducing me to key parts of business, contractors, showing me all the hats I’d need to wear. Before lending, I asked him to share if he’d worked with other designers or had resumes—he’d sent me five resumes of other designers he’d evaluated and said “There’s an abundance of these. I can help you find them.” That gave me confidence he was motivated to help with transition and ensure there’s a plethora of design architects available.
How did you convince yourselves to buy two businesses at once?
I felt crazy—I straight up asked people “Am I crazy for considering this? Is this insane?” Feedback was mixed—it wasn’t as firmly “yes you’re crazy” as expected. We’d already felt like we were making such a big change with so much risk tied up. But we were betting on ourselves—we felt strongly we were worth betting on. There was also an aspect of not wanting to work every single day right with my husband. Once reality set in—Kevin would run things day-to-day, my role would be more in operations for the agency—I wanted to build. It solved the reality that we’d always want our own lanes. As long as the bank didn’t think it’s crazy (they’re most incentivized to tell us no), and if it was lendable and we believed we could do it, why not?
What was the structure for the second business acquisition?
Revenue in 2023 was only $750,000, but prior years it was over $1M. I dug into what changed—the volume of projects was high two years prior (when revenue was highest), but he cut projects in half while margin got healthier. He adjusted pricing—he’d been pricing too low, taking on too much low-work, working himself to the bone instead of higher dollar value projects at higher margins. We took the same approach with purchase—we increased price to get seller to take on a performance-based note. Purchase price was $1.225M—seller financed about 18% ($225K). SDE was $340K—still in our target range. Multiple is a bit higher, especially for a one-man show, but it had what I was looking for.
How is transitioning into a business where the key man is downloading his knowledge without teaching you the technical skills?
It’s hard. But as a product manager, a lot of what I did was getting someone to download their knowledge to me. You have to go into it understanding this is long-term—you’re downloading, and things will click into place. You have to trust it will. Past the 90-day mark, I’m starting to understand parts I need to solve quickly and parts I can wait on. I’m fortunate to have a healthy relationship with him and his wife—they’re great people who genuinely care about the business’s life. He started it in 2017—it was their lifeblood. It’s terrifying, but if it wasn’t, I wouldn’t be doing it.
What will change now that you’ve gone full-time in your new business?
I now have more time to focus on both businesses, but the agency needs a lot from me. We’re hiring—having a process for that didn’t exist. I split my time between businesses daily—we cut off midday: work on design and build in morning, agency in afternoon. That works now at current volume, but won’t when it scales.
Kevin, how are things going in the agency?
Things are going well. Benefit of doing this together is having someone going through similar process we can lean on. Agency is in a place needing operational excellence—that’s a big piece Lindsey brings. She can give resources to agency now, then shift things toward design and build to help it scale. We’ve brought on three new clients and been very successful transferring relationships. Every day/week has challenges—you’re taking over something someone poured blood, sweat, tears into for years—but going as well as possible 6 months into transition.
\h3 class=”wp-block-heading”>Why do you recommend flat fee over hourly for deal team services?Every deal diligence should include a QoE and excellent attorney. On first deal, we worked with Barlo and Williams (flat fee structure). Meant we were both incentivized to close quickly—don’t dilly-dally, don’t redline contracts just because you can, get over the finish line. With QoE, we pivoted from first provider (hourly) to second. First was reasonable rate but estimates didn’t mean anything—we hit over estimate significantly and it cost 3-4 weeks. Second deal, we found Midwest CPA (Chris Barrett). Fixed fee is so much better—you don’t worry about price, can plan/budget for it and move forward. Don’t have to worry if extra call costs $500. In deal process, constant questions need provider incentivized to answer quickly—not someone building billable hours. When spending that much money, easy to look for lowest hourly—I wouldn’t do that again.
Lindsey & Kevin Business Stats
Lindsey and Kevin’s strategic approach resulted in the simultaneous acquisition of two profitable businesses with strong cash flows. Their dual business model provides diversified income streams while leveraging complementary skills. Below are the key metrics from both acquisitions that demonstrate their thoughtful investment strategy and risk mitigation approach.
- Ad agency purchase: $1.6M with $575K SDE ($1.2M annual revenue)
- Design/build company purchase: $1.225M with $340K SDE
- Implemented creative seller financing structures for both businesses
- Maintained healthy cash flow from both businesses during transition
- Successfully transferred client relationships in both businesses
- Leveraged complementary skill sets for operational excellence
| Business | SDE | Purchase Price | Revenue |
|---|---|---|---|
| Holdsworth & Nicholas (Ad Agency) | $575,000 | $1,600,000 | $1,200,000 |
| Collective Creative Outdoors (Design/Build) | $340,000 | $1,225,000 | $750,000 (2023) |
Lindsey & Kevin Method
Lindsey and Kevin’s acquisition method focused on strategic risk mitigation and complementary skill utilization across both businesses. Their process transformed potential weaknesses into opportunities for growth while maintaining operational stability. Here’s how they executed their dual acquisition strategy in practical terms:
- Identified two complementary businesses that matched their combined skill sets
- Implemented graduated seller financing based on performance metrics
- Leveraged seller expertise during extended transition periods (6-12 months)
- Maintained clear operational boundaries between the two businesses
- Used cross-business synergy (ad agency serves design/build company)
- Protected against keyman risk through talent pipeline development
Lindsey & Kevin Tools
Lindsey and Kevin strategically selected tools that enabled seamless operation of both businesses while minimizing overhead. They focused on solutions that provided visibility into key metrics without requiring excessive management time. Their tool selection emphasized collaboration between the businesses while maintaining clear operational boundaries.
- Aquamatch – Deal sourcing and deal box calibration service that helped identify both businesses
- Midwest CPA – Fixed-fee quality of earnings analysis that prevented billable hour creep
- Barlo and Williams – Legal services with flat-fee structure for acquisition documentation
- Pioneer Capital – Lender connection services for securing business acquisition financing
- Standard accounting and operational tools scaled to business size and needs
Key Notes
Lindsey and Kevin’s journey reveals important insights for aspiring business acquirers, particularly those considering multiple acquisitions. Their experience demonstrates that strategic risk management and complementary skill utilization can turn potential weaknesses into competitive advantages. These critical takeaways emerged from their dual acquisition process:
- “X factor” (passion for the business) can overcome objective weaknesses in target businesses
- Clear operational lanes between partners prevent conflict in dual-business ownership
- Graduated seller financing protects both parties during client transition periods
- Fixed-fee professional services create better alignment than hourly billing
- Personal networks and relationships are critical during business transition periods
- Businesses with operational challenges can offer greatest growth potential
Get Started in Just 5 Steps
Following Lindsey and Kevin’s approach, here’s how anyone can begin their business acquisition journey with strategic clarity and purpose. These steps reflect their evolution from part-time searchers to successful dual-business owners, addressing common pitfalls they initially encountered:
- Define your non-negotiable deal box criteria with honest self-assessment of operational preferences
- Work with a third party to validate and refine your deal box beyond standard metrics
- Structure seller financing that protects against key transition risks with graduated milestones
- Secure fixed-fee professional services to maintain alignment with your timeline and goals
- Create clear operational boundaries between business interests to maintain focus and effectiveness
Conclusion
how one couple bought two businesses demonstrates that strategic business acquisition requires more than just financial analysis—it demands thoughtful risk management, complementary skill utilization, and creative deal structuring. Lindsey and Kevin’s journey from corporate professionals to successful dual-business owners reveals that the most effective acquisitions balance analytical rigor with personal alignment. Their story shows that with proper risk mitigation and a clear understanding of transferable skills, what seems like a risky dual acquisition can become a sustainable path to entrepreneurial freedom. As they continue to grow both businesses, their experience offers valuable lessons for anyone considering entrepreneurship through acquisition.