We recently had a discussion with one of our searcher clients who is working on buying a business and thinking about what to build around it. The business provides technology services to schools. The initial idea was to acquire more companies doing similar work and build a roll-up. But the conversation widened: those same schools also outsource accounting, HR, compliance and facilities. Could some of those businesses eventually fit into a holdco? What made it interesting was that both directions had a connection to the first acquisition, but would involve quite different work afterwards. Buying more technology businesses could mean bringing teams and systems together. Expanding into other school services could mean keeping companies more independent and relying on their own leadership. Familiar customers, but different businesses to understand and run. The investor feedback added another layer. They wanted to see how big the opportunity could become, how many suitable targets were actually out there, and how future acquisitions might be funded. Meanwhile, we were still working through the price and structure of the first deal. The interesting part about balance is - Having enough of a longer-term plan to show investors what’s possible, while leaving room to learn from operating the first business. For those who’ve built beyond their first acquisition, how much of your roll-up or holdco plan was clear beforehand and what changed once you were actually running the business?