Think Big, Buy Small

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Learnings From a Former Searcher, Current Investor, and Industry Wise Man Mar 31, 2025

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Kent Weaver was an early participant in the world of search, completing a self-funded search that led to his acquisition of a healthcare company in 2002 and then, four years later, putting on his investor hat to make his first investment in search. Today, he’s one of the most experienced and highly regarded funding partners in the space, having invested in over one hundred searches, both traditional and self-funded. In this wide-ranging conversation, they discuss the qualities that Kent looks for in prospective searchers and future CEOs, including reflections on the importance of both hard and soft skills; industry and company characteristics that he screens for during diligence; the pros and cons of solo versus partnered searches, along with funded versus self-funded searches; trends in the world of ETA; and so much more. Kent is truly energized by his collaborations with searchers, and listeners will gain valuable insights from this fascinating discussion with one who has seen so much in search.

Acquiring Outdoor Recreation Programs as Co-CEOs and Spouses Mar 24, 2025

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Connor McCarthy and Caroline Matthews are not only a married couple and new parents, but they’re also funded searchers turned co-CEOs at Canyonlands Camps. The outdoor recreation industry is little explored in the world of search and their ETA journey is also distinct in that, through the acquisition of summer camps and travel programs, they’ve taken ownership of business-to-consumer businesses, which constitute only a minority of search targets. In this conversation, the pair reflect on the experiences of buying and then operating businesses with a spouse; how they approached investors with their unique thesis; the characteristics that they look for in acquisition opportunities; and the extra complexities involved in the buyer-seller relationship, particularly in cases where multiple generations of one family have been involved in camp operations. They also share steps they’re taking to upgrade facilities and professionalize their camps; how they’re thinking about repeat customers and the progression of programming; along with thoughts on the advantages that have now come with being preferred buyers in the space, ones with a reputation of honoring family legacies. This is an episode about human relationships in ETA, and listeners will learn a great deal from the journey that Connor and Caroline are on.

The Acquisition, Transition, and Operation of a Technology Solutions Company in Texas Mar 17, 2025

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William Young became CEO of Aerowave Technologies in January of 2021. While he has no regrets about his pursuit of the ETA path, his journey to the company’s helm was a difficult one. His story is distinct in that he started out in a partnered, brokered search but ended up as a solo searcher, focusing on proprietary outreach in Dallas-Fort Worth and Boston. Once he closed on Aerowave, Will was met with a number of challenges, including a seller transition that ran over a year; COVID; supply chain issues; running a technical business with very little technical expertise of his own; early culture problems; and the ever-daunting task of hiring talented salespeople. In this conversation, Will also reflects on Aerowave’s many tailwinds, his decision to implement a new enterprise resource planning system, the benefits of speaking directly with his customers, and how he views being CEO through the lenses of fatherhood. Though Will has some scars to show from his search process and early days at the company, listeners will learn a great deal from his accomplishments and his ultimate success in adapting the business to the life he wants to lead.

Insights From a Recurring Investor in Self-Funded Searches Mar 10, 2025

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Sam Rosati is a former searcher turned active equity investor in self-funded searches and, given his experiences, an important focus of this conversation is on the evolution of the self-funded market. It used to be the case that self-funded searchers had to create their investor base from scratch, out of pure networking. Now, however, a path is emerging where a searcher can reach out to a recurring investor in self-funded searches, like Sam, and that investor can then make further introductions, helping searchers who started their ETA journeys with few contacts to more easily find pools of equity to back their deals. Sam discusses how searchers find him, including through his SMBootcamp; his thoughts on when self-funded searchers should start reaching out to investors, along with strategies for building relationships with them; the qualities he looks for in searchers and in the businesses they’re looking to acquire; why he finds this to be such an attractive asset class, and more. Listen to learn about this next chapter in search and the many opportunities it brings for self-funded searchers.

The Purchase, Carve Out, and Transformation of a Remote Software Company Mar 03, 2025

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Betsy Harbison, CEO at Softrip, successfully completed a funded search in 2021. Her story, however, is rather unique in that the business she acquired is a remote, vertical software company that was also a carve out, meaning that a crucial part of Betsy’s journey involved the daunting task of untangling Softrip from its parent company. In this episode, she considers the pros and cons of self-funded versus funded search; why she ended up buying a remote company when her search had initially focused on the Midwest; the thinking behind her decision, in purchasing the business, not to raise any debt; and the challenges she encountered in doing due diligence on a carve out, including the seller’s insistence that she not speak with employees or customers prior to close. She also shares reflections on her first years as CEO, comprising the excitement and the difficulties around not having the luxury to wait before making changes, the transition from too much product customization to a rebuilding of that core product, and also her recent focus on an entirely new product offering. It’s a distinct story of acquisition entrepreneurship and a fascinating conversation.

From W-2 Job, To Startup Life, To Acquisition Entrepreneurship Feb 24, 2025

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In May of 2024, after a self-funded search, Brian Seeling became CEO of PGM Service, a Florida-based company that focuses on maintenance, service, and repair of commercial food

equipment. His journey to become an acquisition entrepreneur is distinct in that he first worked as a software engineer, was then involved in startup life for a number of years, and only recently embarked on the ETA path. In this episode, Brian reflects on the decision to pursue ETA, including his experiences of entrepreneurship through startup versus through acquisition; how implementation of a preventative maintenance service is empowering him to turn an episodic revenue business into a recurring revenue business; his thoughts on Rick and Royce’s suggestion to focus on synergies and cross-selling opportunities via the acquisition of a cold-side business; and more! Brian bought a company in which there are “many ways to win”, an important attribute in assessing acquisition opportunities, and listeners will learn a great deal from Brian’s accomplishments in the ETA space.

Practical Takeaways From A Seasoned Lender To Smaller Firms Feb 17, 2025

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Not only is Zach Duprey a highly experienced commercial lender to those seeking to acquire a small business but, in helping to create a national market for these loans, he has been instrumental in dramatically changing the landscape of small business lending, revolutionizing the market for search. In this episode, Zach describes the “three legs of the stool” that he and his team consider in evaluating transaction opportunities – the underlying business, the searcher / operator, and the investors. Also discussed are the differences and similarities between commercial bankers and equity investors, in terms of their risk assessments and expectations; the relevance of different company attributes, including churn and margins; distinctions between SBA and conventional loans, particularly important to consider when purchasing a growth-oriented company; and many more practical takeaways that will well serve both funded and self-funded searchers on their journeys towards acquisition entrepreneurship.

The Acquisition of a Remarkable Recurring Revenue Business Feb 10, 2025

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After a brokered search, Jenn Braus became CEO at Systems Design West, a company that provides customized ambulance billing, emergency medical services billing, and accounting services to fire and rescue organizations, and one that Rick and Royce believe is “the perfect recurring revenue business.” In this episode, we learn about the beauty of recurring revenue (and how it differs from repeating revenue), and also about the many other attributes of SDW that made the business an awesome acquisition, along with one red flag that gave Jenn pause in her journey towards becoming an acquisition entrepreneur. Furthermore, they discuss why Jenn disliked the search process but loves being CEO; her experience of a very short transition period; the benefits of medium customer switching costs; why SDW was a great fit for Jenn, both professionally and personally; and how walking the ETA path allowed Jenn to create for herself the world in which she wants to live.

Finding One's Way To ETA Feb 03, 2025

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In May of 2021, after a self-funded search, Nick Vandam became CEO of MCI, a telecommunications infrastructure company based in St. Paul, Minnesota. In this episode, he shares his distinct journey, including his days at West Point; competing in triathlons on the U.S. National Team; deployment in Afghanistan; work experience at a large financial services company and then at a doomed startup; followed by graduate school and employment at Raytheon, all the while inching closer and closer to entrepreneurship through acquisition. Once headed down the ETA path, a number of challenges and opportunities presented themselves to Nick, leading him to important realizations about buying and then running a small business. Tune in for insights on the accessibility of acquisition entrepreneurship, due diligence challenges, the beauty of cigar butt businesses, leadership, and so much more.

Where Are They Now? A Conversation with Geoff Duckworth Jan 21, 2025

Show notes

Starting in early February, we’ll begin releasing new episodes of Think Big, Buy Small, season two. Rick and Royce are looking forward to sharing some fantastic conversations with you! Ahead of these new releases, however, we've built a bridge, of sorts, between the two seasons by checking in with season one guest, Geoff Duckworth, who was featured in the episode, “The Self-Funded Journey From Searcher To Seller.” Listeners may recall that Geoff had not only successfully taken the ETA journey and acquired a small business, but that he then went on to sell his company. That episode ended with Geoff at a crossroads, unsure of whether the path forward should involve embarking anew down the ETA path or pursuing other alternatives. Tune in to hear what Geoff has been up to since his earlier conversation with Rick and Royce, along with his reflections on the decisions he made.

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