In this episode of The Intentional Owner, Sam Rosati and Kaustubh Deo dive deep into two interconnected topics: the real tradeoffs of self-funded search versus traditional high-income careers, and tactical frameworks for evaluating industries and revenue quality in SMB acquisition. They open with a candid conversation about what draws people into ETA, weighing lifestyle freedom and long-term upside against the more predictable, but often relentless, trajectory of big law, PE, and IB. Then, they shift gears into practical diligence frameworks, sharing how they’ve each evaluated revenue quality, industry dynamics, and growth opportunities in their own businesses. From win rates and customer retention metrics to local market analysis and pricing strategy, this conversation is rich with hard-earned insights. They discuss: • Why expected returns in self-funded search may be lower than other high-income career paths • How to measure and evaluate revenue quality using real customer data • Frameworks for assessing industry attractiveness as a first-time searcher • The role of local market dynamics, backlog trends, and customer segmentation in due diligence • Common pitfalls in organic growth assumptions and the limits of TAM analysis A tactical conversation for anyone considering ETA or looking to sharpen their diligence process. Topics: 00:00 - Intro 00:46 - Catching up 06:49 - The alternatives to Self-Funded Searches 20:10 - The pitfalls of an industry-agnostic Search 22:44 - Thoughts on Revenue quality 31:50 - Key data points and gut checks to know if the business/industry is healthy 35:50 - Developing organic growth 42:33 - Discovering win-rates in Search 46:01 - Closing questions!