Think Big, Buy Small

Kyle Poll had built a successful career at LinkedIn and Gympass, but he found himself looking for something more entrepreneurial. With five children, a mortgage, and a comfortable career, leaving his corporate life to search full-time for a company to buy was not an obvious choice. Yet Kyle and his wife had built enough financial flexibility to make the leap, and after nearly a year of searching, he acquired GetOutPass, a subscription-based family entertainment business, and merged it with its primary competitor, PogoPass. In this episode, Kyle shares how his experience in enterprise sales shaped his approach to finding and acquiring a business. He explains why he treated relationships with brokers as a systematic sales effort, how his background at Gympass helped him connect with the sellers of GetOutPass, and how he navigated a deal involving multiple owners with competing objectives. Kyle also discusses the challenges of bringing two competing companies together – including the integration of teams, technology, markets, and cultures – and the lessons he learned during his first year as a new owner. Together, they explore what Kyle’s experience reveals about the importance of financial preparation, understanding the motivations of all parties in a transaction, and approaching acquisition entrepreneurship with humility and persistence. Ultimately, Kyle’s journey shows how the skills and relationships built over a successful corporate career can become powerful assets in the pursuit of business ownership.

Entrepreneurship through acquisition is increasingly becoming a global phenomenon, and in this episode Rick and Royce speak with Louis-Clair Francois-Poncet, an HBS alum who returned to his native France after business school to pursue ETA alongside a longtime friend. Since launching their roll-up in 2022, they have acquired fifteen HVAC businesses, combining them under a single company while still preserving the local brands and cultures that made each one successful. Louis-Clair shares how he identified HVAC as an attractive sector, raised capital from French investors, and built deal flow by establishing credibility with business owners. Along the way, they explore the differences between pursuing ETA in France and North America, the distinct motivations of business owners who sell without wanting to retire, the power of bringing professional management and information systems to small businesses, and how a roll-up can create value not simply through economies of scale, but by better management, technology, recruiting, and shared resources. The conversation also considers what it means to build an entrepreneurial career around a unified professional and personal life, and why businesses that depend on skilled tradespeople may prove particularly resilient in an age of rapid technological change. Ultimately, Louis-Clair’s experience offers a compelling look at how the ETA model can travel across borders and how entrepreneurs can adapt it to local markets while still preserving the fundamental principles that make the model work. 

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.

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.