Thanks Luke. Jen, I am in year 1 of a 3 year transition. My transaction is structured a little differently and is an add on. However, I'm happy to share my experience!

Thanks @redacted‌ A couple of thoughts from the operator side. First, how long is "longer"? In my experience, transitions are rarely productive beyond a few months regardless of how they're structured, and the transitioning owner usually mentally checks out around month the 6-9 month mark regardless of whether the transition period is 18 months or more. The earn-out keeps them financially engaged but not operationally engaged. Those are different things, and they're highly correlated to their responsibilities post-close. Get that in writing. On the implication for structure: I'd highly recommend front-loading the knowledge transfer. Whatever you need from them (relationships, institutional knowledge, customer introductions) get it in the first 90 days while you still have their full attention. Most importantly, don't assume a long runway means a long window of engagement. Psychologically, they've sold the business, and they're planning life beyond your transition period. Be prepared to cut the check and walk away before the contracted transition period ends. Better to extract the knowledge and shorten the window than carry a checked-out team member on the books for the full duration.