Sam Rosati and Kaustubh Deo explore when it makes sense to start a business rather than acquire one on The Intentional Owner. The conversation stems from a listener question about the rising difficulty of self-funded search deals, higher multiples for even small businesses, and whether starting from scratch might be a better path forward. They examine the economics of buying a single-crew service business versus building one, the fragility inherent in very small operations, and the underappreciated challenges of replacing an owner who serves as both technician and manager. They discuss: • Why the payback period on small acquisitions often exceeds the multiple paid plus a year • How margins degrade when transitioning from owner-operated SDE to a true EBITDA business • The case for working in a trade before starting versus relying on sales and marketing skills alone • Whether the rise of solo entrepreneurship enabled by digital tools shifts the calculus away from traditional search This episode offers a practical framework for aspiring owners evaluating whether to buy an existing business or build something new in an increasingly competitive acquisition market. Topics: 00:00 - Intro 06:00 - The start versus buy debate for small businesses 10:30 - Personal objectives drive the decision 15:30 - Comparing single-crew acquisition costs 18:30 - The debt payoff timeline versus startup growth 19:30 - The margin degradation of growth 20:46 - Breaking even in year one of a startup 23:27 - Buying bigger versus smaller 37:00 - The fragility of very small businesses 47:00 - The solopreneur alternative 49:00 - Agency versus financial independence 55:20 - Book recommendations and wrap-up