I’m questioning an assumption in my own acquisition search and would value candid perspectives from people who have faced something similar. I’ve worked through more than 60 LOIs over the years. My background is primarily in restaurants, where I’ve partnered, acquired, started businesses, consulted to operators, and written about the industry. Today I’m pursuing a very different direction through SIDUS: senior healthcare and home-based care. The reason matters to me. I believe there is an opportunity to build something that helps older adults remain safely and independently in their homes longer, while building an enduring business around the people who care for them. But I keep running into a problem. I’ve walked away from opportunities in this space during diligence after uncovering financial issues, inconsistencies, or conduct I wasn’t willing to inherit. Walking away from any one bad deal is easy to defend. What I’m questioning is when a pattern becomes a signal. At what point do repeated failed diligence processes stop being evidence that your diligence is working and start telling you to question the vertical, sourcing approach, acquisition criteria, or even the thesis itself? I’ve also tried building advisory support around this effort twice and concluded that the structures I assembled weren’t helping me answer the right questions, so I changed course. I’m not looking for encouragement to “keep going.” I’m trying to diagnose this objectively. For those who have been through something similar, how did you distinguish among: 1. Good diligence correctly filtering bad businesses; 2. A sourcing process attracting the wrong sellers; 3. Industry-specific risks that needed a different underwriting or diligence approach; and 4. Evidence that it was time to reconsider the thesis itself? I’d particularly value perspectives from people who have acquired or operated home care, home health, hospice, senior care, or other healthcare services, as well as searchers who ultimately changed verticals. And if this mission resonates with someone who has deep experience in these areas, I’d be glad to connect privately. I’m increasingly convinced that finding the right people around the search matters as much as finding the right business.