Advertise on podcast: Think Big, Buy Small

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.

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.

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.

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.

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.

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.

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.

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.

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.

In this special “Friends and Family Night” episode, Rick and Royce speak with Meghan Orzetti about the experience of entrepreneurship through acquisition from the perspective of a searcher’s spouse. Drawing on her personal experiences, Meghan shares candid reflections on supporting her husband, Season One’s Michael Orzetti – a Marine Corps veteran, turned searcher, turned CEO – through the uncertainty, sacrifice, and adventure of acquiring a business while raising a growing family. From deployments and cross-country moves to self-funding a search and closing on a deal, Meghan reflects on the practical realities of uncertainty, mobility, and financial planning, as well as the deeper importance of partnership, mutual support, and shared values. Her story highlights how clarity of purpose, open communication, and a commitment to family can transform the ETA journey into something deeply meaningful.

Ike Ukawuba was a self-funded searcher whose path to entrepreneurship began far from the boardroom. Raised in a single-parent household in Chicago, he began his career in engineering before discovering his true passion for business and problem-solving. After several years at Accenture, followed by experience at some startup ventures, Ike found his stride in entrepreneurship through acquisition – a model that allowed him to leverage his skills, take ownership, and build something enduring. In this episode, he reflects on his path from consulting to running a home healthcare company, the challenges of leading a large team, and the fulfillment that comes from making a difference in people’s lives. Ike’s journey is one of thoughtful risk-taking, resilience, and purpose-driven leadership, offering valuable insights for anyone interested in acquisition entrepreneurship.

In this episode, Rick and Royce sit down with Rob LeBlanc, Co-Founder at Ambit Partners, to explore the evolution of search fund investing beyond traditional markets. Rob traces his path from building an ETA platform in South Africa to backing searchers across frontier economies, offering an insider’s view on how entrepreneurship through acquisition is adapting globally. The conversation examines the unique dynamics of searching and operating in less developed capital markets – where relationships, local fluency, and cultural context often outweigh formal structures – and explores how factors such as currency risk, investor networks, and institutional maturity shape the search process. Through comparative insights between developed and emerging markets, this discussion highlights the expanding boundaries of the search model and the growing diversity of its global practitioners.

Michael Aubrey, having walked the path from searcher to successful operator and investor, draws on his wealth of experiences to offer a masterclass in small business growth. In this episode, he talks candidly about navigating early operational setbacks and hiring challenges, the strategies he employed to build a national salesforce, and why he believes a deep understanding of one’s customers is the foundation for real improvement and scale. You’ll hear reflections on employee compensation models, the critical role of company culture and accountability, and what it really takes to succeed as a CEO in the world of small business acquisitions. Packed with hard-earned lessons on management, grit, and the value of taking a hands-on approach to operations, Michael’s insights into leadership, hiring, and growth strategy are not to be missed.

In this bonus episode, hosted by Adam Outland, we're featuring a conversation from our friends at The Action Catalyst, a top-rated leadership and entrepreneurship podcast. While Think Big, Buy Small focuses on the unique entrepreneurial path of acquiring and operating a small business, The Action Catalyst shines light on all types of entrepreneurs and the distinct insights they offer. This episode welcomes Jim Sebenius, renowned negotiation expert, Harvard Business School professor, and host of Dealcraft: Insights From Great Negotiators. In a wide-ranging discussion, Jim shares strategies and lessons from both government and corporate settings; explains the powerful “3D” model of negotiation; reflects on why internal negotiations are often the most challenging; highlights the value of keeping a deal diary; and more. Whether you're deep in deal-making or simply looking to sharpen your negotiation skills, this episode delivers wisdom, wit, and practical insights for everyone at the table.

In this episode, Rick and Royce are joined by A.J. Wasserstein, Senior Lecturer at the Yale School of Management, for a deep dive into one of the most critical – and often misunderstood – aspects of buying a small business: revenue quality. Together, they unpack the full spectrum of revenue types, from transactional to contractually recurring, and explore how these distinctions impact everything from growth potential to customer retention, acquisition strategy, and valuation. With real-world insights and a clear framework for evaluating revenue during diligence, this conversation is essential listening for any aspiring acquisition entrepreneur looking to de-risk their investment and build lasting value.