A story of 7 LOIs that did not result in an acquisition:

A story of 7 LOIs that did not result in an acquisition: #1: This was my first offer. Spent a lot of time crafting and overthinking it. Got along great with the seller and felt I had some very relevant experience. Got steamrolled by another offer that was all cash, and they had direct experience. Honestly, if I had won this deal, I would have had no idea what to do next. #2: I was a finalist buyer. The broker came back and said the seller took the deal off the market. All the offers were about the same and within the range they told the seller to expect. Seller felt the business was worth more, so he wanted to stick around and grow it. BTW, he was a 78 and just had major surgery. #3 Finalist with one other buyer. He won. Later connected with him in real life, and he told me, "Honestly, I think you dodged a bullet." #4 Made a fair offer (4x maybe?) Was for a veteran-owned government contracting business, so a small pool of buyers. Seller wanted more. That was 2 years ago, and still on the market. #5 Finalist with one other buyer. They offered a lower seller's note (think broker told me $50k less). They won the deal. #6: Seller says they are ready to sign my offer. Later found another Darden grad made an offer for $2m more than I did on the same deal, and the seller said she "just trusted me more," so she was ready to go with me. I had another seller come in the same day and say they were ready also, and I ended up deciding to pursue the 2nd deal. #7 This was the 2nd deal from above. Spent 9 months under LOI. Deal fell apart one, and then the day they called me to say it was back on (and had a big new contract) was the day I found out my wife was pregnant. Deal finally died 2 weeks before my daughter was born when the sellers backed out. We were >< close to closing. --- What's my lesson here? Deal-making is not for the faint of heart and is much more about people than numbers.