Think Big, Buy Small

Rick and Royce tackle intriguing questions from aspiring entrepreneurs on acquiring businesses. They discuss key traits of successful acquisition entrepreneurs and whether these can be taught. The conversation dives into the pros and cons of franchises versus standalone businesses, highlighting strategic considerations. They explore crucial financial modeling techniques and address common due diligence pitfalls. Additionally, the hosts share their thoughts on utilizing AI in business acquisition and offer a sneak peek into what's coming next season!

Logan Leslie, CEO of Main Street Auto and a Harvard graduate, dives into the fascinating world of business roll-ups in the automotive sector. He explains why the auto repair industry is ripe for consolidation and shares his unique strategies for success. Logan emphasizes the critical role of cultural fit, team dynamics, and innovative financing methods like sale-leaseback transactions. His insights challenge traditional skepticism about roll-ups, showcasing a blueprint for growth that prioritizes both employee welfare and operational efficiency.

Adriana Garcia Ceja, a Harvard Business School graduate and CEO of ElderTree Care Management, shares her inspiring journey of acquiring an aging life care management business while navigating motherhood. She emphasizes the importance of mission-driven goals in business, particularly for women. Adriana also discusses the unique challenges and advantages of the ETA career path, her experience closing a deal while pregnant, and the evolving landscape of elder care. Her insights reflect the balance of purpose and profit in entrepreneurship.

Kent Weaver, an experienced investor with a remarkable background in search funds, shares insights honed over years in the industry. He discusses what he looks for in prospective searchers, emphasizing the blend of hard and soft skills. Kent explores the dynamics of partnered versus solo searches, and how each path impacts success. He also touches on the evolving landscape of self-funded searches and how industry characteristics play a crucial role in diligence. His deep enthusiasm for collaboration with searchers shines through in this engaging conversation.

Caroline Matthews and Connor McCarthy, co-CEOs of Canyonlands Camps, share their unique journey of acquiring summer camps and outdoor programs. They discuss the challenges of balancing family life and entrepreneurship, particularly during the pandemic. The couple reflects on their investor strategy and the importance of honoring family legacies in business. They highlight the intricacies of operating seasonal businesses, building customer loyalty, and the emotional nuances involved in valuing outdoor recreation properties—all while navigating their partnership as spouses.

William Young, CEO of Aerowave Technologies, shares his journey from private equity to leading a technology solutions company. He discusses the intricate dynamics of ownership transition, especially during the challenges posed by COVID and supply chain issues. Young highlights the importance of direct customer conversations and the difficulties of hiring skilled salespeople in a technical field where he admits to having little expertise. His reflections on adapting business operations while balancing family life provide valuable insights for aspiring entrepreneurs.

Sam Rosati, a former searcher now thriving as a recurring investor in self-funded searches, shares his unique journey and insights into the evolving market. He discusses strategies for building investor relationships and emphasizes the importance of early communication. Sam also reveals the key traits he seeks in effective entrepreneurs, evaluates business stability, and explores the complexities of investor relations. Tune in for an engaging discussion on navigating the opportunities and challenges in the world of self-funded acquisitions!

Betsy Harbison, CEO of Softrip, shares her unique journey in acquiring a remote vertical software company focused on multi-day tour operators. She discusses the challenges of untangling the business from its parent company and her strategic choice to avoid debt in the acquisition. Betsy reflects on the complexities of managing customer expectations while shifting from product customization to a more scalable model. Her insights on navigating investment partnerships and the evolution of female representation in the searcher community add further depth to this fascinating entrepreneurial story.

Brian Seeling, CEO of PGM Service, shares his unique journey from software engineer to acquisition entrepreneur. He discusses the contrasting paths of startups versus acquisitions, emphasizing how to evaluate business opportunities. Brian highlights the advantages of a preventative maintenance model, transforming revenues from episodic to recurring. He also delves into the challenges of leadership transitions and the importance of operational systems in driving growth and profitability. Listening to his experiences offers valuable insights for aspiring entrepreneurs in acquisition entrepreneurship.

Zach Dupree, a veteran commercial lender with expertise in small business acquisitions, shares invaluable insights on navigating the lending landscape. He discusses the 'three legs of the stool'—the business, the operator, and the investors—essential for evaluating acquisition opportunities. Zach highlights the contrast between commercial bankers and equity investors and the importance of trust in negotiations. He provides practical advice for first-time acquirers, emphasizing the nuances of SBA versus conventional loans and the evolution of search funds in recent years.