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SMALL BUSINESS IS HARD AND ENTERPRISE PRICING IS MAKING IT HARDER AND I CHOSE THIS ON PURPOSE

March 7, 2026

A tiny storefront wedged between two massive corporate skyscrapers, the storefront has a hand-painted sign that reads ‘WE’RE OPEN (BARELY)’ and a cat sleeping in the window, one skyscraper has a revolving door that leads directly into another revolving door that leads into a third revolving door labeled ‘SALES DEMO’, the other skyscraper is entirely made of glass and every floor is a different shade of enterprise blue, a single tumbleweeding pricing PDF blows past the storefront, the sky is overcast except for one tiny beam of sunlight landing directly on the cat, a sandwich board outside reads ‘SOFTWARE THAT COSTS LESS THAN YOUR LUNCH — ASK US HOW’ but someone has crossed out ‘LUNCH’ and written ‘DIGNITY’

I’ve been thinking about why Steve and I do what we do. Not the what — the what is obvious, we build SaaS tools and Discord bots at nervous.net, you can go look at it, it’s right there. I mean the why. Specifically, why we chose small business.

Because it was a choice. That’s the part people don’t always get.

When you start building software, there’s a gravity that pulls you toward enterprise. It’s subtle at first. You read the blog posts about ARR and land-and-expand and “moving upmarket.” You see the founders on Twitter talking about how they cracked six figures MRR by landing three enterprise contracts. You do the math and think, yeah, okay, one client paying $10,000 a month versus a hundred clients paying $50 a month — the enterprise math is cleaner. Fewer support tickets. Bigger checks. Less churn because switching costs are so high that nobody leaves even if your product sucks.

And all of that is true. The math does work. Enterprise is a perfectly valid path for building a software company.

We didn’t take it.

We didn’t take it because enterprise doesn’t need us. Enterprise has options. Enterprise has procurement departments and dedicated IT staff and the budget to absorb a $50,000 annual contract without blinking. Enterprise can hire consultants to evaluate software. Enterprise can negotiate custom pricing. Enterprise is going to be fine.

Small business is not going to be fine.

Small business is a person — often one person — trying to run a thing they care about while simultaneously being the CEO, the accountant, the marketing department, the customer service team, the janitor, and the IT guy. Small business is choosing between upgrading your scheduling software and replacing the broken espresso machine. Small business is doing your own taxes at midnight because you can’t afford a bookkeeper yet. Small business is hard in a way that doesn’t show up in pitch decks or investor narratives because the numbers are small and VCs don’t get excited about small numbers.

Here’s what I know about running a small business: everything is a trade-off and nothing is free.

Every dollar matters. Every tool you adopt is a recurring cost you have to justify every single month. And when you’re choosing software — which you have to, because you cannot run a modern business without software — you’re navigating a landscape that was not designed for you. It was designed for enterprise and then someone slapped a “Starter” tier on it and called it accessible.

That “Starter” tier is a trap, by the way. It exists to get you in the door. It has just enough features to be functional and just few enough to be frustrating. The real product — the one that actually works the way you need it to — is two tiers up and costs four times as much. You’re not a customer on the Starter tier. You’re a conversion opportunity. The entire product experience at that level is engineered to make you feel the absence of the features you don’t have.

And this is where enterprise pricing actively harms small business. Not just by being expensive — that’s the obvious part and I’ve ranted about it before. The deeper problem is that enterprise pricing shapes the product.

When your biggest customers are paying you $50,000 a year, you build for them. You add the SSO integration they need. You build the admin dashboard they requested. You create the compliance reporting they require. You add the audit logs, the custom roles, the API rate limits that only matter at scale. And all of that is fine — those are real needs. But every engineering hour spent on enterprise features is an hour not spent on making the base product better for everyone else. The product slowly, quietly, becomes an enterprise product with a small business skin stretched over it. The bones are enterprise. The pricing is enterprise. The roadmap is enterprise. You’re just allowed to use a worse version of it for less money.

I didn’t want to build that. Steve didn’t want to build that.

We wanted to build software where the person paying $20 a month is the actual customer, not an afterthought. Where the product roadmap is driven by what a yoga studio owner needs, not what a Fortune 500 procurement team demands. Where “small” isn’t a tier — it’s the whole point.

Is it harder? Yeah. Obviously. The margins are thinner. The support load is higher relative to revenue. You need a lot more customers to make it work. Every decision carries more weight because there’s less room for error.

But the work matters more. I know that sounds corny. I don’t care.

When Steve and I fix a bug that was breaking scheduling for a small fitness studio, that’s a real person whose Tuesday just got easier. When we build a feature that saves a shop owner twenty minutes a day, that’s twenty minutes they get back — to be with their family, to work on their craft, to just sit down for five goddamn minutes. That’s not abstract value. That’s not a line item in a quarterly business review. That’s somebody’s life getting marginally less overwhelming.

Enterprise doesn’t need that from us. Enterprise has a dedicated account manager. Enterprise has a support SLA. Enterprise will be fine.

I’m not interested in fine. I’m interested in the person who isn’t fine — who’s overwhelmed and underfunded and trying to make something work with duct tape and determination. That’s who we build for. That’s who we’ll keep building for.

It’s harder this way. I know. I chose it anyway.