How to Read a Revenue Trend Before You Buy: The Decline Analysis Framework Every Digital Buyer Needs
Most buyers anchor on the trailing twelve months and miss the revenue trend entirely. Here is the decline analysis framework I use before every bid on a digital asset.
SaaS vs. Content Sites: How to Compare These Two Asset Classes as Acquisition Investments
A 3x multiple on SaaS and a 3x multiple on a content site are not the same investment. Here is how to evaluate these two asset classes side by side before you make an offer.
What Due Diligence Actually Looks Like on a $50K–$250K Digital Asset Deal
Most buyers say they’re doing due diligence. What they’re actually doing is reading a listing, maybe asking three follow-up questions, and then convincing themselves the numbers check out. I’ve been on both sides of enough digital asset deals to tell you that real due diligence — the kind that protects you when something goes wrong […]
How to Calculate Your Maximum Offer Price for a Digital Asset: A Buyer’s Underwriting Framework
Most buyers price digital asset deals backwards. Here is a step-by-step underwriting framework for calculating your maximum offer price — and the discipline to hold the line when negotiations get emotional.
Churn Is the Number You’re Not Asking For: How to Evaluate Customer Retention Before You Buy a SaaS or Subscription Asset
Every buyer I know asks about revenue on the first call. Most ask about traffic. Very few ask about churn — and that is exactly why churn is where deals quietly fall apart after closing. In my experience evaluating SaaS and subscription acquisitions, churn is the single most predictive number for whether a business will […]
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 […]
Traffic Risk Is the Hidden Killer in Digital Asset Deals — Here’s How I Underwrite It
Traffic risk is the number one thing that separates a good digital asset deal from an expensive mistake. I have reviewed hundreds of acquisition targets over the years, and I can tell you with confidence: most buyers spend 80% of their due diligence time on revenue and almost none on understanding where that revenue actually […]
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 […]
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 […]