How to reapproach a deal you thought was dead?

September 09, 2025

by a searcher from The University of Michigan - Stephen M. Ross School of Business in Portland, OR, USA

Greeting friends! How should one go about reaching out and restarting negotiations with a business you walked away from? The backstory: After some summer fun/chaos and moving back to the Northwest, I am trying to reinvigorate my search. I still have connections with a business in the area that I had once pursued but ended up walking away from because the sellers way over valued their business and we could not agree on price. It has been a little less than a year since our last communication. It was not sour, but it wasn't the most friendly. The business is great, the sellers are not as great, but I want to reconnect. What is the communities advice?

Reply by a searcher
from Brigham Young University in Charlotte, NC, USA

Hi ^redacted‌! I’m about to drop a company that I like, but the sellers aren’t playing ball. I’ve thought about how I would check in with them in a few months though, so your post is very timely. I would write up a casual message to them. I would provide them an update on your end since you last talked with them, and then I would ask the sellers how the business is going and how they are doing. See where is goes from there.

Reply by an investor
from Harvard University in Dallas, TX, USA

I did a number of renegagements and we eventually bought 2 of them. My experience was that face to face was the best. I'd say.....I'm going to be right by you, could I drop in for coffee. Then id come up with a reason why it was rearranged (it was usually seeing another seller I was going to schedule with) and try that date instead. I felt it was oddly the most efficient use of time, vs any back and forward on email or letter, where i had the preconceptions of the previous time. A lot can change, things may come out that you don't know about. For example 4 years after trying to buy a business the seller finally confided in me, it was in his dead wives name and that he was embarrassed he didn't know what to do about that. We did that deal. I'd never ever have guessed that. So go in with an open mind, best is face to face and be pretty direct.

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