Acquiring Minds Podcast: How 1 Couple Bought 2 Businesses
Host: Will Smith
Guests: Lindsay Buckheit & Kevin Black
Release Date: May 12, 2025
Introduction
In this compelling episode of Acquiring Minds, host Will Smith interviews Lindsay Buckheit and Kevin Black, a dynamic entrepreneurial couple who navigated the intricate journey of acquiring not one, but two businesses. Their story offers invaluable insights into acquisition entrepreneurship, highlighting the challenges, strategies, and successes they encountered along the way.
Initial Planning and Motivation
The Buckheit-Blacks' acquisition journey began with a unified goal: to transition out of their corporate W2 roles and achieve financial freedom through business ownership.
Will Smith sets the stage:
"The original plan was not that both wife Lindsay and husband Kevin would buy a business. At first, the idea was that buying a business would be the path Lindsay." [00:00]
Lindsay Buckheit elaborates on their initial motivations:
"I think the three common paths when people think about striking out on their own are starting a business, building a real estate portfolio, or buying a business." [05:21]
Facing Early Challenges
Despite their enthusiasm, Lindsay and Kevin encountered significant obstacles during the initial eight months of their search. Balancing full-time jobs with the demanding process of business acquisition led to slow progress.
Kevin Black reflects:
"We were not any closer to actually buying a business. We were both still working full time and just did not have the time to do the amount of calls that you need to do." [07:26]
This period underscored the difficulties of being part-time searchers without professional guidance.
Turning Point: Partnering with AquaMatch
Recognizing the need for specialized support, the couple decided to collaborate with AquaMatch, a team founded by Athena Simpson, to accelerate their search and refine their acquisition strategy.
Lindsay Buckheit shares their decision:
"We started working with her and her team in January of 2024. Pretty immediately saw traction." [11:08]
Athena Simpson explains AquaMatch's role:
"They took about a month to get to know us and would actually send us deals to be like, yes, no, and why." [12:35]
This partnership was pivotal in redefining their "deal box"—the criteria they used to evaluate potential acquisitions.
Acquiring the First Business: Holdsworth and Nicholas Inc.
With AquaMatch's assistance, Lindsay and Kevin successfully identified and acquired their first business, Holdsworth and Nicholas Inc., a media buying agency based in San Antonio.
Athena Simpson provides details:
"It's an ad agency out of San Antonio. SDE was about $575,000. Purchase price was $1.6 million." [25:56]
Kevin Black highlights key factors that made this acquisition attractive:
"The biggest thing was the cash flow of how healthy it was... It had a few employees that were going to stay with the business." [27:18]
Strategic Deal Structure
To mitigate risks inherent in acquiring a business, Lindsay and Kevin devised a sophisticated deal structure involving significant seller financing and forgivable notes.
Lindsay Buckheit explains the structure:
"We have $576,000 in a seller note, which is over a third of the purchase price. This includes a 5% equity injection and a $494,000 forgivable note split into two parts based on performance." [33:00]
This arrangement provided them with financial flexibility and protection against potential revenue declines.
Navigating the Lending Process
Securing funding was a challenging yet crucial aspect of their acquisition strategy. Initial attempts with traditional banks resulted in pushback due to perceived risks such as key man risk and client concentration.
Athena Simpson discusses the hurdles:
"The three main risk areas were key man risk, client concentration, and the transfer of relationships." [49:22]
Ultimately, partnering with Matthias Smith at Pioneer Capital proved instrumental in overcoming these obstacles, allowing them to finalize their financing securely.
Expanding to a Second Acquisition: Collective Creative Outdoors
Bolstered by their first acquisition's success, Lindsay and Kevin pursued a second business, Collective Creative Outdoors, a design and build firm in Austin. This move was driven by their desire to diversify and leverage their complementary skill sets.
Kevin Black shares the rationale:
"I wanted to build something where I could see it grow from nothing to something, aligning with my background in operations and product management." [55:37]
The second acquisition followed a similar deal structure, ensuring consistency and risk management across both businesses.
Balancing Dual Business Ownership
Managing two businesses simultaneously presented new challenges, including time management and operational oversight. To address this, Lindsay and Kevin implemented a structured daily schedule, dedicating mornings to one business and afternoons to the other.
Kevin Black describes their approach:
"I work on the design and build in the morning and the agency in the afternoon. At the current volume, it's feasible." [77:39]
This strategy allowed them to maintain momentum and drive growth across both ventures effectively.
Transitioning and Mitigating Key Man Risk
A critical aspect of their acquisition strategy was mitigating key man risk—ensuring that neither business was overly dependent on a single individual. In the case of Holdsworth and Nicholas Inc., they worked closely with the seller to facilitate a smooth transition and identify replacement talent.
Lindsay Buckheit emphasizes the importance:
"It's crucial to protect yourself while the seller is still in the business and plan for their eventual departure." [38:01]
Kevin Black adds:
"We asked the seller to help us find designers to replace him, ensuring business continuity." [59:08]
Lessons Learned and Best Practices
Throughout their acquisition journey, Lindsay and Kevin discovered several key lessons that they believe are essential for aspiring acquisition entrepreneurs:
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Refining the Deal Box: Narrowing acquisition criteria can paradoxically lead to better deal flow by reducing decision overload.
"Narrowing the deal box helped us focus and make better decisions, even when dealing with limited time." [12:35]
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Professional Guidance: Engaging with experienced advisors like AquaMatch and financial experts can significantly expedite and streamline the acquisition process.
"Working with professionals was worth the investment and solved the problems we were facing." [48:48]
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Structured Deal Financing: Implementing seller financing and performance-based notes can provide financial safeguards and align incentives with sellers.
"A larger seller-financed note ensured both of us were incentivized towards the success of the business." [40:53]
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Transition Planning: Ensuring a smooth transition by securing the seller's ongoing involvement and identifying replacement talent is vital for maintaining business stability.
"The seller stayed on for six months to facilitate the transition and introduce me to key parts of the business." [59:08]
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Flat Fee Services: Utilizing flat fee structures for services like QofE and legal counsel can prevent budget overruns and keep the acquisition process on track.
"Fixed fee structures allowed us to budget effectively and move forward without unexpected costs." [80:55]
Conclusion
Lindsay Buckheit and Kevin Black's journey exemplifies the power of strategic planning, professional partnerships, and adaptive problem-solving in acquisition entrepreneurship. By acquiring and managing two distinct businesses, they not only achieved their goal of exiting the corporate world but also set a foundation for continued growth and diversification.
Their story serves as an inspiring blueprint for other entrepreneurs aiming to navigate the complexities of buying and scaling businesses. Whether you're just starting your acquisition journey or looking to expand your portfolio, the insights shared by Lindsay and Kevin offer valuable guidance to help you succeed.
Notable Quotes:
- Will Smith: "Acquiring an existing business is an awesome opportunity for many entrepreneurs." [03:11]
- Kevin Black: "I was trying to fit square pegs into round holes because I was desperate to find something." [07:45]
- Athena Simpson: "If you're too broad with your deal box, there's just too much noise in the businesses that you're looking for." [19:48]
- Lindsay Buckheit: "Narrow the deal box and have better results when you're already struggling to find deals." [24:06]
- Kevin Black: "It was beyond just making a change; it was about betting on ourselves to make it work." [65:00]
For more insights and detailed discussions on acquisition entrepreneurship, subscribe to the Acquiring Minds newsletter at acquiringminds.co and explore additional resources on their YouTube channel.