When I wrote Befriending the Goon Squad — an essay on the importance of patience and discipline when building a product — I received dozens of variations of the following question:

So how do you stay disciplined? How do you avoid getting distracted by new ideas or dismayed by bad weeks, even when you only have a few users? Various people

I think the reason this question is so common is because people incorrectly assume the launch to be "the hard part", largely due to misconceptions perpetuated by the zeitgeist. As far as I can tell, there are two prevailing stereotypes of what building a company "is really like":

  1. It is the easiest and most rational decision ever, a path to economic freedom and personal fulfillment paved with bottles of champagne and hockey-stick MRR charts. The only thing stopping you is gumption, courage, and — conveniently! — a $199.99 info product that the author happens to be hawking.
  2. It is like chewing glass, a gauntlet of horrors and difficulties equally Sisyphean and Herculean, an unending cavalcade of eighteen-hour days that ravage your body and devour your mind. We must honor the company-builder, for theirs is a plight (and therefore glory) unparalleled.

Neither of these are accurate: life as a founder [1] is long and difficult, sure, but not in the ways that tend to make for good hagiography, and the journey begins (rather than ends) with the initial launch.

Your day is neither as glamorous as margaritas on the beach nor as dire as a never-ending sharknado storm. It's mostly stuff like:

In short: you will be spending a lot of time, thousands of hours, doing work that is somewhere on the spectrum between "mildly unpleasant" and "evokes daydreams of working as a barista". This is time that, if you napkin-math it out, values your labor at $20/hr. If you're doing the absolutely right thing at any given point in time, you're spending more time making less money doing something you probably find less fun than any other job you've had.

So why do this? Why spend a lot of time and energy and effort doing work that, in its best form, can be lovingly described as malaise punctuated by fleeting ecstasy?

This is a fair question, given that Buttondown despite that is the thing that I've spent more time on in my life (both in terms of wall clock time and hours spent working) than anything else.

If I was purely motivated by compensation, I would be working in Big Tech [2]; if I was purely motivated by getting to hack on interesting problems all day I would be working for a small startup or freelancing [3].

The answer, I think, is some combination of satisfaction and agency:

  1. Satisfaction — If I had a Mount Rushmore of “best moments of my career”, three out of the four [4] are some variation of “a person used Buttondown, liked it so much that they paid me thousands of dollars, and then still liked it so much that they told all of their friends and colleagues about it.” If you are the kind of person whose favorite day at a company is when you get to send a launch email for a project: imagine that, times three hundred.
  2. Agency — every morning, I wake up and get to decide exactly how I want to build Buttondown. Granted, I rarely do that — I try to be disciplined, and spend most of my time doing what is Pareto optimal for the business, even if it’s stuff I’d rather not do (see the prior list re: debugging rendering bugs and sales calls.) But if I am ever feeling a little antsy, I can completely wipe my slate clean and start working on an ambitious refactor or feature branch just because I want to. Almost all of the best parts of Buttondown have been built not out of a well-strategized, market-researched ten-day deep dive but out of me waking up with an idea stuck in my craw that only eight hours of flow work will dislodge.

Those words, vague as they are, are not universal: I’m sure if you talk to a dozen other founders in a similar phase of their journey you’ll get a dozen different answers. But they’ll all have an answer. (You might need to get a couple shots of whiskey in them first to have them shake whatever their sound-bite-shaped answer is — “I really want to make the world a better place by letting people chat with PDFs” is marketing, not self-reflection.)

If you're thinking that you want to build a product (whether it's a nights-and-weekends thing, or you want to raise a few rounds of VC money, or whatever) — ask yourself why. Make sure your answer is really, really good; that answer will be equal parts amulet and bulwark.

I can't resist ending on a little lagniappe, especially when the rest of this essay can feel a little, uh, dour:

This month my wife and I went on our honeymoon, a two-week affair spanning Paris and Tuscany. There is no PTO when you're running your own business; there are the systems and structures you were wise enough to place ahead of time, and that is all.

But I managed to only spend a mere fifteen minutes every morning (typically mid-croissant) checking emails to make sure nothing had burned down — and nothing did. [5] And when I arrived back home stateside, travel-weary and jet-lagged, I of course had a mountain of emails waiting for my reply — life does not stop just because you're touring Montmartre or Monteriggioni.

But I also had received a raise.

Amidst the bug reports and unanswered sales calls and low-priority checker failures, Buttondown's MRR had grown — not a huge amount, but not a small one either — while I was eating my body weight in carbohydrates.

That, admittedly, was pretty cool.

  1. A term that, after all these years, I'm still not quite comfortable with, for all of its Eisenberg-ian connotations ↩︎

  2. Anyone who says that Big Tech is not the best risk-adjusted way of maximizing your career earnings is lying, fyi! ↩︎

  3. Your reward for a successful product is to spend less and less time on the product itself, and more on the business surrounding it. ↩︎

  4. The remaining fourth moment: hiring people at Stripe. Being a line manager at a big tech company has lots of downsides but recruiting and growing awesome people outweighs pretty much all of them. ↩︎

  5. Thank you, Ben! ↩︎

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