Why Sellers Sell: Using Seller Motivation Intelligence to Negotiate Better Digital Asset Deals
Most buyers spend the first two weeks of due diligence buried in spreadsheets. They audit the P&L, verify traffic, cross-reference revenue claims against Stripe exports. That work matters. But there is a question most buyers never ask until it is too late, if they ask it at all: why is this person selling? That question […]
The First 90 Days After You Close a Digital Asset Deal: What Operators Actually Do to Protect and Grow What They Bought
Closing a digital asset deal feels like a finish line. You have survived the due diligence, negotiated the price down to something defensible, signed the transfer agreement, and watched the funds move. And then, somewhere around day three of actually owning the thing, the real work begins. In my experience working through acquisitions, the first […]
The Pre-Close Checklist: What to Verify in the Final 30 Days Before a Digital Asset Deal Closes
I’ve walked away from two deals in the final week before closing. Both times, something surfaced during the pre-close verification window that the original due diligence didn’t catch — not because the diligence was sloppy, but because a 30-day gap between signing an LOI and wiring funds is enough time for a content site to […]
The Earnout Trap: Why Seller Financing and Earnout Structures Are the Most Misused Tools in Digital Acquisitions
If there is one area where I see digital acquisition deals go sideways — not at closing, but in the months after — it is the earnout. Specifically, it is the earnout that both the buyer and the seller think they understand but that neither has actually defined with enough precision to survive the first […]
Algorithm Risk in Digital Acquisitions: How to Audit a Site’s Google Dependency Before You Buy
I’ve looked at a lot of acquisition listings where the traffic numbers looked solid — consistent monthly visitors, decent page views, no obvious red flags in Google Analytics. Then I dig into the traffic sources, and everything changes. One site I evaluated last year was pulling 85% of its traffic from a single keyword cluster. […]
SDE Adjustments Are Where Digital Deals Break Down: What Every Buyer Must Verify Before Trusting a Listing
Every digital business listing that crosses my desk comes with a seller discretionary earnings number. Sellers present it like it’s a fact. Brokers repeat it like it’s gospel. And buyers — especially newer ones — accept it at face value and build their entire offer around a number that may have been engineered to look […]