I love this bit from Paul Graham on pattern-matching founders:

Though the most successful founders are usually good people, they tend to have a piratical gleam in their eye. They're not Goody Two-Shoes type good. Morally, they care about getting the big questions right, but not about observing proprieties. That's why I'd use the word naughty rather than evil. They delight in breaking rules, but not rules that matter. This quality may be redundant though; it may be implied by imagination.

I love this not because I agree with the sentiment, and in fact I think you can point to a lot of Icarian tendencies (and perhaps pervasive industry-wide rot) as germinating in this naughtiness, but because it is a specific and opinionated characteristic — as opposed to, like, "determined!" and "smart!" and "driven!" It's novel, it's a characteristic with a viewpoint around which reasonable people can agree/disagree.

Antimetal is not a YC company, but it certainly embodies naughtiness. Its founder made a large hullabaloo about trying to commission "the highest quality publicly available version" of the Facebook Red Book, but of course couldn't resist a tiny act of digital vandalism by inserting its own branding into the scan.

Does this matter, on a grand scale? Is this an evil act? Probably not, but certainly a naughty one.

Buttondown in 2025 has reached a sort of escape velocity, less in terms of growth per ce (though also that!) and more in terms of the median user being very far way from my orbit: these users are less technical and more wary than the ones I am used to onboarding.

Users of new tools — especially tools that must be entrusted with important data — are wary these days. They're wary of pivots to video, of shifting business models and sudden price hikes and emails announcing that the curtain is coming down this time next week. It is unfortunate that this wariness — a kind of cynicism — is not only pervasive but entirely rational. Anyone who has used anything new over the past few years has a high number of since-shuttered apps that they trusted with their time and money and data and energy, only to be rewarded with an "Our Incredible Journey" email.

At a high level, I think this stems from the same vein as naughtiness: a tendency to think of systems and expectations as something to be overcome, as social contracts as a thing to be voided or ignored rather than bolstered.

We get a lot of questions that boil down to "why should I trust [Buttondown]?" The blithe answer — the one that I generally try not to give, even though I think it's the most rigorous and correct one — is that, well, you shouldn't — insofaras you should only trust any company as much as you can exfiltrate your data. We've made a lot of decisions in service of decades-long continuity; we're cash-flow positive, we're stable and robust; our incentives are aligned with yours. But, more than that, the email space is novel in that you can always pack up your entire dataset — archives, addresses, et al — and ship them off to a competitor. You shouldn't need to trust us; you should find us valuable enough to be worth keeping around.

Email is also unique in that it's, by software standards, a very mature industry — one with a long history already. Many of my customers come with data exports from tools that they started using fifteen years ago; prospects who I reached out to in 2019 follow up in 2025.

After twelve months of active usage, we ask every paying customer a single question: "why are you still using Buttondown?" ^[1] There are two answers whose volume dwarf the rest:

1. Because the customer support is really good.
2. Because I haven't had an experience that has prompted me to look elsewhere.

Customer goodwill is a real asset; it is one that will probably become more valuable over the next decade, as other software-shaped assets start to become devalued. It feels almost anodyne to say "it is in a company's best interest to do right by their customers", but our low churn and high unpaid growth in a space uniquely defined by lack of vendor lock-in is perhaps a sign that being nice is an undervalued strategy. And "being nice" in a meaningful sense is, like "being naughty", something that gets baked into an organization's culture very early and very deeply.