Should I target solopreneurs or real businesses with my AI content and software?
Short answer
Real businesses, usually. Solopreneurs and entrepreneurs want AI content the most, but they're broke and perfectionists. Established companies have budget and real problems. I built software for entrepreneurs at $75 a month, then found legacy local media wanted it at hundreds a month. The sweet spot is about 5 to 50 employees.
I learned this with my newsletter software.
Why did I move away from entrepreneurs?
I thought I was building for entrepreneurs at $75 a month. As I dug deeper, it became obvious: entrepreneurs are broke, and they're perfectionists.
Local newsletter operators, the people I know best, are a version of this. One competitor's cheapest plan is $500 a month for one newsletter. Most local operators won't pay $200. Some would pay $100, but not very many.
Who has the money?
"guess who's not broke and who's not a perfectionist is legacy local media, the people running newspapers for the last 50 years."
They either don't do newsletters or they do them very poorly, because they don't know how. And they have money, at least enough to pay $300 to $500 a month. We quickly had enough of them saying they want this right now at hundreds of dollars a month.
They aren't perfectionists either. Their brief is: get me a newsletter people will read in 10 minutes and I'm all on board. Our pricing goal for the software became a minimum of $200 a month, with $500 soon, and I can see a version of lightbreak at $2,500 a month.
Why does the biggest audience pay the least?
Because the people who want your content most aren't the people you want to sell to. Target entrepreneur types and you'll get the most views, because they're the ones looking for this content. They're just not the most valuable, not even close.
I think of it as a ladder. Local media gets you a lot of attention fast and cheap, but it's less valuable attention unless you have a strong angle. Entrepreneurs for AI are one step above that. An AI trainer I met, who has made content since 2021, admitted that if he started over he wouldn't target solopreneurs. He'd target actual businesses.
What size company is the sweet spot?
Roughly 5 to 50 employees.
| Company size | Problem |
|---|---|
| Under 5 employees | Not enough money |
| 5 to 50 employees | The sweet spot |
| Over 50 employees | More competition and more demand for professionalism |
Legacy local media companies fit exactly, with 5 to 25 employees being normal. And niching down to own a category is extremely valuable.
Should I ignore the small audience I already have?
No. I have that audience today, so going all in on local media for the community and agency side probably makes sense, while building the bigger stuff too. In parallel, the biggest thing besides my audience is having an AI agent do cold outreach to legacy local media brands, because they've got the money.
What if a competitor is cheaper?
Don't race them down. A competing community for small operators charges about $50 a month. Our power play is going up-market. He's going to entrepreneurs. We go to existing brands. For more on that, see why selling to bigger businesses is often easier and self-serve versus high-touch B2B software.
Answered by TJ Larkin. From client calls, my own product notes and work with my AI agents, 2024-2026. Last updated .