Think Big, Buy Small

Latest Episodes:

Navigating the Legal Process of Buying a Small Business Oct 26, 2026

Show notes

Buying a small business involves much more than simply agreeing on a price. To explore the legal process of getting a deal across the finish line, Rick and Royce are joined in the studio by Jared Shwartz, a mergers and acquisitions attorney who specializes in smaller firms. Jared shares many lessons from his extensive experience representing both buyers and sellers, including how to choose an advisor with the right small business M&A background, what information belongs in a letter of intent, and why working capital can become one of the biggest sources of deal friction. They also discuss the importance of identifying potential obstacles early in the process, such as multiple owners, complicated corporate structures, third-party consents, and financing challenges; how to navigate negotiations without creating deal fatigue; and why maintaining a strong relationship with the seller can be critical even after a deal closes. Throughout the conversation, listeners will hear practical insights into managing risk, avoiding surprises, and using the legal process to increase the likelihood that a transaction gets done.

When Search Doesn’t End in an Acquisition Oct 19, 2026

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What happens when a searcher doesn’t find a company to buy? In this episode, Rick and Royce talk with Kristin Wihera, a Navy veteran and HBS graduate who spent nearly two years searching for a business to acquire before ultimately ending her search without a deal. Kristin reflects on the emotional highs and lows of searching, the challenges of cold outreach, and the tradeoffs of pursuing a funded search with investors who had particular expectations around company size, growth, and returns.

She also discusses how her military background helped – and sometimes hindered – her efforts to establish credibility with sellers, why she ultimately expanded the search beyond her original industry focus, and which businesses she seriously considered as acquisition targets but ultimately did not close on.

Her story, however, is not one of failure. After ending her search, Kristin found a role with a venture fund investing in early-stage, deep-tech companies in Utah, a job she believes she would not have qualified for without the skills, experience, and network she developed while searching. Also discussed are changes in the search landscape, including the growing importance of relationship-driven sourcing, the evolving role of brokers, and the increasing divergence between funded and unfunded search. Kristin’s experience offers a valuable reminder that a search can be transformative, positively impacting a career, even when it doesn’t end with an acquisition.

From Entrepreneur to Acquisition Entrepreneur Oct 12, 2026

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Entrepreneurship through acquisition doesn't always begin with a formal search. In this episode, Rick and Royce talk with Aaron Wyatt, an entrepreneur who built his business organically after leaving a sales job to become an independent manufacturer's representative. Aaron shares how he grew his business by deepening relationships with customers and family-owned manufacturers, while deliberately adding complementary product lines. He also reflects on the risks of leaving W2 employment and why, for him, those risks felt manageable when viewed as simply taking the next step. Aaron has since taken another step in his journey, purchasing a garage door service company with a longtime friend.

He discusses what attracted them to the business, how they approached the transition with employees, the small operational changes that helped improve performance, and why they chose a buy-and-hold strategy rather than pursuing a quick exit. Along the way, Rick and Royce explore what Aaron's journey reveals about the many paths into acquisition entrepreneurship, and why existing entrepreneurs may be an important, though often overlooked, group of business buyers. This episode serves as a reminder that, for some entrepreneurs, the path to owning a business isn't necessarily a formal search but simply recognizing the next opportunity and being willing to take it.

From Searcher to Seller: The Long Road to a Successful Exit Oct 05, 2026

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Bruce Isaacson spent two years searching for a company to buy before acquiring a decades-old marketing research firm in 2005. Since that time, he has transformed the business, shifting its focus to litigation research and building a thriving professional services firm. In 2025, after years of growth, Bruce made the difficult decision to sell. In this episode, Bruce is joined by Rudy Scarito, the investment banker who advised him on the sale. Together with Rick and Royce, they discuss the patience and persistence required to turn around a business, the importance of finding a company that fits the entrepreneur, and why success sometimes takes longer than expected. Bruce and Rudy also share their candid reflections on the emotional complexity of selling a business, from choosing the right buyer and navigating “cold feet” to thinking about employees, succession, and life after ownership. The conversation offers a rare look at the other side of the ETA journey – and why, for some owners, selling a business is less about accumulating wealth or retiring than about building something meaningful and leaving it in good hands.

Reflections On the Evolution of ETA Sep 28, 2026

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Jeff Stevens, one of the earliest searchers and a longtime investor in the ETA ecosystem, joins Rick and Royce to discuss how search has evolved over the past thirty-five years. In this episode, he reflects on the early days of search, when the model was largely uncharted territory, and contrasts that experience with searching in today’s more developed – but still challenging – landscape. Jeff discusses why searchers should focus on building relationships and credibility with business owners, how technology has transformed the sourcing process, and the trade-offs between industry-focused, geographically focused, funded, and self-funded searches. He also shares his perspective on the growing overlap between search and private equity, the role of the entrepreneur-CEO in creating value, and why he believes the traditional search model’s emphasis on managing risk and buying strong businesses remains powerful. They also delve into why search success rates have declined as the ecosystem has grown, the changing role of investors, and the importance of distinguishing between simply buying a company and buying a great company. Tune in to this engaging conversation to hear how one of ETA’s original practitioners views the opportunities and challenges facing the next generation of searchers.

Should Searchers Look More Seriously at Franchises? Sep 21, 2026

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Michael Horowitz is a former searcher who acquired, scaled, and ultimately sold a portfolio of Wingstop franchise restaurants before becoming an investor in the ETA ecosystem. In this episode, he shares his unconventional journey to business ownership and offers an insider's perspective on what makes franchising a compelling but often misunderstood path for acquisition entrepreneurs. Together, they discuss the advantages of established brands, proven operating systems, benchmarking, and more predictable cash flows, as well as the tradeoffs associated with royalties, choosing the right franchisor, and managing multi-unit businesses. They also explore why franchise opportunities are often overlooked by searchers, how franchise portfolios are valued, why geographic density matters, and what role acquisitions and new unit development play in creating value over time. Whether you're considering a more traditional search or evaluating franchises as part of your acquisition strategy, this conversation offers practical insights on when and why franchising may be an attractive path to business ownership.

The Role of Culture in Scaling an ETA Business Sep 14, 2026

Show notes

After a self-funded search led to the acquisition of Ally Waste in 2020, James Crawley grew the company more than thirty-five-fold. What did it take to scale the business from a handful of employees to a nationwide operation, with hundreds of team members working independently across dozens of states? Many entrepreneurs focus on systems and processes when growing a business. James, however, argues that culture deserves equal attention. In this episode, he explains how a clearly defined mission and a set of core values – including an unusual "no jerks" policy – became the foundation for scaling Ally Waste. James also discusses why culture is more than a set of aspirational statements, how it shapes hiring and management decisions, why investing in people can become a lasting competitive advantage, and how leadership is ultimately about developing people who serve others. Whether you're acquiring a small business or leading a growing organization, tune in to learn how an intentional culture can become one of the most powerful tools for driving performance, building loyalty, and sustaining long-term growth.

The Rise of Long-Term Holding Companies in ETA Aug 31, 2026

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In Season Two, Kent Weaver, one of the most experienced operators and investors in the search ecosystem, joined Rick and Royce for a wide ranging conversation about entrepreneurship through acquisition. In this episode, they focus on the rise of long-term holding companies, vehicles designed to acquire and build multiple businesses over an extended time horizon. The conversation explores why some entrepreneurs are choosing to build companies over decades rather than pursue a single acquisition and exit, what makes a successful HoldCo CEO, and how disciplined acquisition strategies and operational playbooks can create long-term value. They also examine how long-term HoldCos differ from private equity and whether this emerging model represents a new chapter in the evolution of entrepreneurship through acquisition. Whether you're considering a traditional search or exploring newer models of acquisition entrepreneurship, this conversation offers valuable insights into an important development shaping the ETA landscape.

Season Three Questions and Answers with Rick and Royce Dec 01, 2025

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Hosted by producer Katie Zandbergen, Rick and Royce return for their end-of-season dive into listeners’ most pressing questions – those that many aspiring acquisition entrepreneurs wrestle with. They explore how age and personal finances may influence ETA risk tolerance; whether an MBA truly matters for success in a traditional search; how to handle the loneliness that often accompanies searching for and running a small business; where searchers commonly spin their wheels early on; how to evaluate red flags during diligence; the realities of buying a job versus a business; advantages and drawbacks of franchising; whether now is a good time to search; and much more. Packed with insights drawn from decades of ETA experience, along with stories and humor, this wide-ranging conversation is essential listening for anyone exploring entrepreneurship through acquisition.

Partnership, Purpose, and the ETA Path to Concierge Medicine Nov 24, 2025

Show notes

Partners in search, Nick Kerr and Shaquille Walker, join Rick and Royce to share their journey from risk-averse upbringings to acquiring HealthBridge, a concierge primary care clinic on Long Island. In this conversation, they discuss how their backgrounds, family considerations, and desire for autonomy led them to entrepreneurship through acquisition, while also reflecting on the emotional highs and lows of searching for, buying, and operating a small business. Furthermore, they describe what it’s like to partner with a founder who remains deeply involved in the practice, why concierge medicine offers an appealing model for both physicians and patients, and how they plan to build a differentiated, prevention-focused platform through thoughtful expansion. Along the way, the conversation explores physician burnout, the value of separating clinical care from business management, and the compelling alignment that strong operational leadership can create for doctors, patients, and investors alike.

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