September 19, 2025
Tom Howard was lying on his back, sick with COVID, watching $9,000 a day drain from a company he had just signed over to himself, all because someone on his team could not resist talking about an acquisition. He lost a second deal months later for the same reason. Two costly, avoidable disasters. One lesson, repeated loudly: in business, information is currency — and giving it away carelessly costs you everything.
Why Acquisition Deals Are So Fragile
The moment between when an acquisition is agreed upon in principle and when it officially closes is the most dangerous period in any deal. This is the due diligence window — when either party can walk away based on what they discover, what they hear, or how they feel about the trust that has been established.
When employees at Climate Control Experts started hearing rumors through the technician grapevine that their company was being sold to Fetch-a-Tech, it created panic. Employees began considering whether to leave. CCE’s leadership became furious. The deal came within hours of being cancelled. The only reason it survived was that the sellers were losing $9,000 a day and could not afford to wait for a better option. Tom got lucky. He knows it.
The second deal — Cal Air — did not survive. Someone on the team told a CSR at another company. That CSR talked. Cal found out. He felt betrayed. The deal was dead, not because of price or terms or due diligence findings, but because of a single conversation that should never have happened.
The Psychology of Leaks: Pride Is the Culprit
Tom is direct about why people talk when they shouldn’t: pride. They want their friends to know they are involved in something big. They want to feel important. They want to share the excitement. And in that moment, the short-term pleasure of telling someone an impressive secret outweighs the abstract risk to the deal.
He has seen this at every level of business. Owners with $100 million companies talk too soon. Managers who were explicitly told to keep information confidential still tell their inner circle. The pattern is consistent: excitement and pride overwhelm discipline.
His prescription is equally consistent: keep the circle of knowledge as small as physically possible, for as long as the deal requires. If telling a team member is not necessary for them to do their job right now, they do not need to know. When you do tell people, make the stakes crystal clear — not as a scare tactic, but because they deserve to understand what they are responsible for.
Building a Deal Culture That Protects Confidentiality
After the Climate Control Experts near-disaster, Tom implemented a simple but powerful accountability mechanism: when he needed to share deal information with a team member, he sent himself a reminder email immediately, timestamped, laying out who was told what and on what date. This created a paper trail of responsibility and signaled to recipients how seriously he took their discretion.
He also became far more disciplined about where he held business meetings. A lost deal months after the Cal Air debacle was caused by an employee seeing Tom meeting with another business owner in a public place — and then speculating out loud about what that meant. The speculation spread, damaged the other owner’s relationship with his employees, and killed a deal before it could even begin.
Tom’s rule: never meet prospective acquisition targets in places where either company’s employees might be present. Treat deal conversations with the same confidentiality you would expect in a medical or legal context.
Trust Is the Real Currency of Business
Every deal Tom describes in the book — from buying Lee’s Air on a payment plan from the original owner, to convincing Collin and Trevor to give him Climate Control Experts with their cash still in it, to Cal Air giving him a second chance after the first deal collapsed — was built on trust, not contracts.
The most efficient deals happen between people who trust each other enough to move fast. Tom and Collin’s acquisition closed in a weekend because they trusted each other. The Cal Air deal was structured on a handshake across two tax years to benefit Cal’s situation — because Cal trusted Tom’s word.
Every time a deal collapsed, it was because trust was broken — usually by information being shared too broadly, too early. And rebuilding trust after it has been broken is exponentially harder than preserving it.
The Bottom Line
Tom’s most painful chapter is the one where he exposes his own failure. He did not have to write it. He chose to, because the lesson is too important to leave out. If you are building toward an acquisition — whether buying or selling — treat information about that deal as classified until the moment the contracts are signed. Your team’s excitement is understandable. Your own is too. Channel it into execution, not conversation. The time to celebrate publicly is after the funds hit the bank.