The Moment Before The Deal Has A Name
Every acquisition looks clean once it closes. A press release goes out, two logos sit next to each other, and everyone shakes hands. What nobody sees is the six months before that, when the deal almost died three or four times over small things: a number that did not tie out, a founder who got cold feet at the wrong moment, a piece of diligence that turned up something nobody wanted to explain.
I have sat on both sides of that table for a long time now, first advising companies on how to raise capital and sell themselves, and now running one that has to make its own calls about what to buy and how to buy it. The view from each side taught me different things, and most of what I know about a good acquisition, I learned from watching the bad ones fall apart.
What Actually Kills Deals
It is rarely price. Buyers and sellers usually get to a number they can both live with faster than people expect. What kills deals is trust breaking down somewhere in the middle, usually because someone was not straight about something early on.
I watch people make the same mistake constantly: they treat diligence as a hurdle to get through instead of a chance to build the case for their own business. A seller who hands over clean, organized information and flags the ugly parts before anyone finds them looks like someone worth doing business with. A seller who makes a buyer dig for basic facts looks like someone with more to hide, even when they are not hiding anything.
On the buy side, the same thing works in reverse. If you show up to a negotiation having actually done your homework, asking specific questions instead of generic ones, sellers relax. They start believing you will follow through on what you say. That belief is worth more in a negotiation than almost any single term in the contract.
The Part Nobody Prices Correctly
Here is something I think people get wrong constantly: they price a deal on the numbers in front of them and treat everything else as noise. Culture fit, how a management team makes decisions, whether the people staying on actually want to be there after the check clears, all of that gets waved through in the excitement of getting to a signature.
I have seen deals that were financially perfect on paper struggle for years because the people side never got worked out. And I have seen deals with thinner margins for error succeed because the two sides actually understood how the other one operated before they signed anything.
If I am looking at a business to buy, I want to spend real time with the people who run it day to day, not just the executive who is selling. I want to know how decisions get made when nobody senior is in the room. That tells you more about what you are actually buying than another round of financial modeling.
A Trade-Off Worth Naming
There is a trade-off in every deal that nobody says out loud: speed versus certainty. Move fast and you keep momentum, you keep the seller engaged, you avoid the fatigue that kills a lot of processes. Move slow and you catch more of the problems before they become your problems.
Neither one is right. The skill is knowing which one the situation calls for. A founder who has been through a sale before and knows what they want can move fast with you. A first-time seller who is nervous and needs to understand every step needs you to slow down, even if that costs you some momentum. Matching your pace to the other side’s readiness matters more than having a fixed process you run every time.
What I Would Tell Someone About To Do Their First One
Get the incentives on the table early. Ask people what they actually want out of the deal beyond the number, because the number is rarely the whole story. Someone selling a business they built might care as much about what happens to their team as what happens to their bank account.
Write everything down as you go, even the informal agreements, because memory gets generous with time and everyone remembers the deal a little differently a year later.
And do not let a good number talk you out of a bad feeling. If something about how the other side operates does not sit right during diligence, that feeling usually turns out to be information, not nerves. I have learned to trust it every time I ignored it and regretted it, and every time I listened and was glad I did.