Why solopreneurs need to pick one number
Your pricing table is an illusion
In 2008, Craigslist charged $25 to post a job listing in San Francisco, New York, and a handful of other cities. Everything else on the site was free. That single price point, applied to one category of post, carried the company past $100 million in annual revenue. The team was fewer than 50 people. 25 bucks was the whole pricing strategy.
I offer one single membership option for my agency. One number, one service and the only options are the payment delivery schedule. I like the simplicity. I like being transparent about it. And I like how easy it makes my work.
But the solopreneur internet has convinced itself that pricing is an architecture problem - you’re supposed to build a matrix, with a free tier at the bottom, pro in the middle, enterprise at the top, maybe an add-on for API access. Stripe makes it easy to spin up 6 plans before lunch, and so of course, people do. Then they spend the next 4 months wondering why nobody converts past the free tier and whether the “growth” plan should include 5 seats or 10, and flagellating over any number of minute tweaks and problems...
Craigslist didn’t have this problem because Craigslist refused to create it.
Craig Newmark and Jim Buckmaster understood that the cost of a decision scales with the number of options. Barry Schwartz published The Paradox of Choice in 2004, documenting exactly this effect - more options make buyers feel stuck, not empowered. More options make us freeze up. Decisions are, in fact, the enemy.
A job listing on CL costs $25. You either need to post a job or you don’t, and the decision takes roughly 3 seconds.
Compare that to a SaaS pricing page with a toggle between monthly and annual billing, 4 columns of feature comparisons, a “most popular” badge on the middle tier, and a FAQ section explaining what happens when you hit your usage cap. This is closer to homework. We don’t like homework. We didn’t come to your website to ~do homework.
When you have one number, your support burden mostly disappears. Nobody emails asking which plan is right for them, and nobody churns between plans, creating billing edge cases that eat your Tuesday afternoon. The buyer knows what they’re paying and they can get on with their life, and you can get on with providing a service...
Having one price forces you to pick your best customer. Craigslist didn’t try to monetize casual users selling a couch. They picked the customer with the highest willingness to pay (recruiters, HR departments) and charged only that customer. Everyone else used the site for free, which built the audience that made the paid product worth $25.
I keep seeing founders do the opposite, building a pricing page with 4 columns before they have 4 customers. Patrick McKenzie, who’s spent years writing about SaaS pricing at Kalzumeus, has pointed out that most founders underprice because they’re afraid to pick a number and live with it. The tier system feels safe; because if the $29 plan doesn’t work, maybe the $49 plan will catch a different segment. But what actually happens is you split your own attention across customers who want completely different things from you.
Sure, you’re leaving money on the table. In theory, some customers would pay $75, some would pay $200, and a tiered model captures that surplus. ~In theory.
In practice, capturing surplus means expending infrastructure: sales calls, plan comparisons, feature gating, upgrade flows, dunning emails for failed payments on the wrong tier, etc etc etc. For a company with 500 employees, that stuff already exists or it’s negligible to create. For a solo founder running a business from a laptop, you just gave yourself a second job. Or a second ~thing to automate, which might in fact appeal to your tinkerers brain - but it’s still a time and energy suck.
Craigslist in fact left enormous amounts of money on the table. Analysts said so constantly throughout the 2000s. The company could have charged for apartment listings, for car sales, for event posts. Instead, Buckmaster reportedly told the world etc that the company was focused on serving users, not maximizing revenue. What came out the other side was a company that printed cash with almost no overhead and no VC pressure. The business worked because the pricing was so simple it barely required a business.
Basecamp (37signals) ran the same experiment. One plan, one price, for years. Jason Fried and David Heinemeier Hansson wrote about this in Rework in 2010, arguing that the complexity of pricing tiers is a tax on your own team. Every tier you add is a support document, a marketing page, a billing scenario, a decision point for your customer and it all adds to the eternal cruft of SaaS. I think they were right, and most solopreneurs already suspect this but they talk themselves out of it because a single price feels too exposed and too scary.
The math on simplicity is boring, which is probably why people ignore it. One price means one landing page, one onboarding flow, one email sequence. Fewer places for a buyer to get confused or wander off.
Four tiers means you need to explain why each one exists. I have never seen a SaaS company explain the difference between “Pro” and “Business” in one sentence without using the word “advanced.” If you can’t do it either, that’s your answer.
The instinct to build a pricing menu comes from the same place as the instinct to add features before launch: the performance and ~feeling of diligence. But I think it mostly boils down to procrastination.
Pick one number and charge for one thing.
You can always bolt on complexity later.
But good luck ripping it back out.
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