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.
Broker-Listed vs. Off-Market Digital Asset Deals: What Buyers Get Wrong About Where to Find the Best Acquisitions
Every buyer eventually asks some version of the same question: should I be hunting on the brokers, or should I be going off-market? The answer most people give is a shrug and a vague nod toward “it depends.” That is not useful. I have been through enough deals on both sides of this line to […]
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 […]
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 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 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.
The Concentration Trap: How Single-Source Revenue Risk Can Destroy an Acquisition’s Value
When One Source Holds All the Power Most digital asset buyers focus on headline metrics: monthly revenue, traffic volume, profit margins. These numbers matter. But experienced acquirers know that a clean income statement can mask a structural vulnerability that no multiple can justify — concentration risk. Concentration risk occurs when a disproportionate share of a […]