Buyers price uncertainty. Every credibility hit you take shows up somewhere: as a price cut, a tighter indemnity or a buyer who quietly walks away. And most of what diligence finds, you could have found first.
Six behaviors that kill deals
Hiding related-party transactions: They surface, and when they do, the buyer starts wondering what else is hidden.
Shopping the LOI after signing it: Buyers find out. The M&A market is smaller than founders think.
Revenue claims you can’t back up: If the data doesn’t support the number, the number doesn’t survive.
Playing dumb about obvious issues: It usually sounds like “I didn’t think losing our biggest customer last month was material.”
Moving the goalposts: The financials are “ready to go,” then they need “minor cleanup,” then they have to be recreated. Or all the code is “proprietary,” until tech debt and open-source dependencies start surfacing.
Gaslighting: “I never said that.”
None of these kills a deal on its own. Together they tell the buyer it can’t trust you on the things it can’t independently verify, and that’s where the price cut comes from. The fix takes discipline, but it’s simple: disclose early, disclose hard and answer the same question the same way every time.
Momentum is fragile
Losing pace in diligence is often fatal. Every stalled week erodes the buyer’s confidence and your own optionality. Lawyers will ping-pong endlessly over points that should be settled in a direct business conversation; when that happens, your job as the founder is to interrupt. Pick up the phone and resolve it with your counterparty.
What diligence finds
The same findings come up in deal after deal.
IP ownership gaps: Contractor agreements without proper assignments, prior-employment carve-outs and university affiliations that complicate ownership.
Quality-of-earnings issues: If 40% of your contracts contain termination-for-convenience clauses, the buyer reads 40% of your revenue as at risk.
Undisclosed problems: A major issue that wasn’t disclosed before the LOI destroys buyer trust on the spot.
Founder stock: Missing or improperly filed 83(b) elections.
Privacy and AI: Public privacy policies that don’t match actual data practices, or models trained on data the company didn’t have rights to. Either can kill a deal at signing or come back after closing as an indemnity claim. In tech deals, this is increasingly the finding I see most often.
Customer concentration
Concentration is one of the most common findings to actually move deal economics. At around 10% of revenue in a single customer, buyers start discounting. Around 20%, they meaningfully retrade. Around 30%, they restructure the deal. Top-five and top-ten concentration get evaluated separately on top of that.
Pull your top 20 contracts before the LOI and map every change-of-control clause; many enterprise contracts terminate or require consent on a sale, and the customer knows it has leverage. A contract the customer can terminate at will is barely a contract for diligence purposes, so expect the buyer to discount that revenue or push it into an earnout. And the buyer will call your customers, so know which ones are happy enough to take that call.
When concentration shows up, buyers respond structurally: an earnout tied to customer retention, an escrow tied to specific renewals or a price adjustment if a named customer leaves within a set period after closing. Each shifts customer-loss risk back to you. The remedy is operational, not legal: renew or expand those relationships before the data room opens.
Find it first
Most of these issues you can identify yourself before the data room ever opens. The ones that surface mid-diligence are the ones that move price.
Ahmed Hasan is the founder and CEO of Venture Bridge Law, a corporate and M&A boutique. This article is general information, not legal advice.