I buy boring online businesses that survive AI and compound forever.
That is the whole thesis in one line. Small, profitable, AI-resistant digital assets with owned audiences, bought at a fair multiple, held for decades.
No fund timeline. No LPs. No exit clock. If you are running one of these and thinking about selling, this is exactly how I think.
What I actually look for
Four kinds of business, usually somewhere in the fifty thousand to three hundred thousand a year range.
Newsletters with a real, engaged list - paid or ad-supported, where the audience relationship is direct.
Affiliate and content sites that are not one Google update away from zero.
Communities with a paid or hybrid model, where the value is the people, not the platform.
And micro-SaaS - simple tools with recurring revenue that solve one thing well.
The non-negotiables
Some things I will not bend on.
An owned audience, an email list I would rather have than any amount of borrowed traffic.
Traffic diversity, so no single channel is life support.
Light operations, something that runs in twenty hours a week or less.
And profit. Positive cash flow today, not a growth curve and a story. Profitable is not a preference here. It is the gate.
No venture baggage. Bootstrapped or lifestyle businesses, built to run, not to raise.
What I pay, and how
I am not trying to steal anything.
I pay two to four times annual revenue. Most of it, seventy to eighty percent, in cash up front. The rest as an earnout over the following year or two. Close in thirty to sixty days.
I can pay a fair multiple precisely because I am buying to hold forever. Your valuation is my entry point, not my exit opportunity. When you never plan to flip, you can be patient about price.
The five principles underneath it
Owned audience over rented traffic. Email lists survive algorithm changes. Search rankings do not.
AI-resistant, not AI-proof. Nothing is truly AI-proof. But trust, community, curation, and taste have natural moats, and they compound while commodity content gets arbitraged to nothing.
Cash flow over growth. I am not buying TAM narratives. I am buying businesses that throw off cash now.
Forever hold, not a five-year flip. No fund forcing an exit. I buy to hold for thirty years, and that single fact changes how I operate and what I will pay.
Light operations, deep value. Twenty hours a week or less. Not because I am lazy - because leverage creates freedom, and freedom creates optionality.
Why sell to me
I decide fast. No investment committee, no board. If there is a fit, we move.
I hold forever. Your creation keeps running. Your subscribers and users stay served. No gut, no flip, no leverage games.
I actually operate. I have built things from zero. I understand newsletters, content, and communities. I am going to run what I buy, not hand it to a spreadsheet.
And I pay fairly. I have been a seller too. I know how it feels to get lowballed, so I do not do it.
If that sounds like your business, send me a note. I will respond within a week.