Buyers and Builders The Real Playbook Behind an Operator-Led Roll-Up (10 Acquisitions in 18 Months)
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Jan 13, 2026 Jeremy Yamaguchi, a serial entrepreneur in home services and founder of Cabana, shares insights from his impressive journey of acquiring 10 companies in 18 months. He reveals the untapped tech opportunities in traditionally 'boring' home services and discusses the fragmented nature of the industry. Jeremy highlights his strategy for growth through M&A and vertical software, emphasizing the importance of good-faith transactions and hands-on operations. He also shares valuable lessons like the significance of comparing strengths and the value of deep industry networks.
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Choose Opportunities By Comparative Advantage
- Play to your comparative advantage and choose problems that overlap with your strengths.
- Know thyself and write down what you are actually good at before picking opportunities.
Do Hands-On Work And Build Teams
- Spend time in the weeds: build product, run marketing, and work directly with field teams.
- Hire well and make people management energy-adding rather than draining.
M&A + Ops + Software As A Moat
- Cabana's thesis: buy leading local pool companies, professionalize ops, and build vertical software as a durable moat.
- Owning tech and a long time horizon creates advantages over PE buyers focused on short-term EBITDA.
