Tim Niles 
The deal closed on a Friday. By the following Monday, the acquiring CEO wanted a synergy update, and the IT question got a one-line answer in a status deck.I’ve watched that moment repeat across…
The deal closed on a Friday.By Tuesday morning, the new owner was sitting in a server room that nobody had documented in eleven years.The financials were clean. Legal diligence was thorough. The QofE…
Financial due diligence has a playbook. Legal due diligence has a playbook.IT due diligence, in mid-market deals, does not.That is why it is the most consistently underexecuted piece of work in the…
Two months after a private equity firm acquired a midsize manufacturer, the company paid $1.2 million to a ransomware group. The deal had looked clean. The Wall Street Journal reported the incident…
You’re watching AI predictions pile up. Some say it will revolutionize everything. Others warn about the risks. Most business owners sit somewhere in the middle, trying to figure out what any of this…
I spent last Tuesday watching a 60-employee financial services firm celebrate passing their compliance audit. The champagne came out. The CEO sent an all-hands email about their commitment to…
April 15, 2026 Last month, a mid-sized private equity firm we know discovered something that nearly killed their M acquisition deal. Three weeks before closing, their standard financial due diligence looked solid. Revenue was growing, margins were healthy, and the management team seemed competent. Then they dug into the target company’s IT infrastructure. What they … Read more