2-3 years ago I lost a deal because the family didn't think I was paying enough.
I had successfully built a strong relationship with the seller. He was motivated to do the deal and excited about the deal structure (incl. rollover equity, board seat, consulting agreement, earn-out).
However, his family (wife) never got onboard since they had heard he could sell for an extra turn of equity to a strategic (~$5m EBITDA). So the deal died in the 11th hour. One of my bigger defeats.
Lessons learned:
• Create alignment with ALL stakeholders. Anyone can derail it.
• Don't let a deal go to the 11th hour without 100% alignment.
• Never stop promoting the value prop of partnering with you.
• Time kills deals.
Note: I keep in close touch with the seller. He regrets it because he's bored and doesn't feel valued.
