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 Email Newsletters Are Really Worth: How Buyers Should Underwrite Subscriber Lists, Churn, and Monetization Before They Bid
If you have spent any time on the digital acquisition marketplaces in the past year, you have noticed something: newsletter deals are everywhere. Substack newsletters, beehiiv publications, ConvertKit-powered email communities — they are all trading hands, and sellers are asking for multiples that, on the surface, look a lot like SaaS businesses. Three times revenue. […]
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 […]
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 […]
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.
Revenue Multiple by Asset Class: Why the Same 3x Means Something Very Different on a Newsletter, SaaS, or Content Site
When a broker lists a digital asset at 3x annual SDE, most buyers read that number and move on. They should not. The multiple is not the deal — the asset class behind the multiple is the deal. I have reviewed hundreds of listings across newsletters, SaaS products, and content sites, and the thing that […]
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 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 […]