How AI Is Reshaping Content Site Valuations — And What Smart Buyers Are Doing About It in 2026
I’ve been buying and evaluating content sites for years, and I’ve never seen a market shift as fast as what’s happened over the last eighteen months. AI-generated content, AI-powered search, and Google’s continued algorithm updates have fundamentally changed how I think about what a content site is worth — and I’m seeing a lot of […]
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 […]
How to Structure a Letter of Intent for a Digital Asset Acquisition
Most buyers spend weeks running due diligence on a digital asset — auditing traffic, verifying revenue, stress-testing SDE adjustments — and then write a letter of intent that gives away every advantage they’ve built. The LOI is where deals are won or lost, and most acquisition guides treat it like a formality. It is not. […]
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. […]
Content Sites Are Down 33%: What Smart Buyers Are Doing Differently in 2026
I’ve been watching the digital acquisition market shift underneath buyers’ feet in real time. If you came into 2026 expecting to run the same playbook you used in 2023 — buy a decent content site, collect AdSense, wait for appreciation — I want to walk you through what the data actually says, and what the […]
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 […]
How to Negotiate the Asking Multiple Down: A Data-Driven Framework for Digital Asset Buyers
Most buyers accept the asking multiple as fixed. Here is how to build a risk-adjusted counter-offer using the asset’s own data, market comps, and a structured negotiation approach that sellers actually respect.
How to Vet a Seller Before You Ever Look at the Numbers
Most buyers spend weeks analyzing an asset but skip vetting the seller. Learn the four signals, five questions, and paper trail checks that reveal whether a seller can be trusted before you ever open the P&L.
Are You Ready to Buy a Digital Asset? Take Our Free AI Readiness Assessment
Most people who want to get into digital asset investing ask the same question: “How do I know if I’m actually ready?” Not ready in theory — but ready right now, with the skills, capital, and time they actually have. We built something to answer that question — and we think it’s the most useful […]