I am, scientifically speaking, the problem.
I am ambitious. I have plans. I have a list of things I’d like to learn this year, none of which I have started, and a list of things I’d like to launch this year, also pristine and untouched. There is a fancy Greek word for this: akrasia, the state of acting against one’s own better judgment. There is also a less fancy word for this: me.
If you’ve ever opened a productivity app at 11pm with the conviction that this was the one that would change your life, and then closed it twenty minutes later with seven new categories and zero completed tasks, well, I think we’d be good friends.
I tried to build my way out of it.
For the longest time, I held a quiet, embarrassing belief: somewhere out there was the perfect to-do app, and when we found each other, sparks would fly, choirs would sing, somebody would make a movie about it.
Eventually I decided to build it myself. I spent several months on a beautiful little app that organized your tasks. I wasted many weekends on it, in the way you can only waste a weekend when you are very motivated and very wrong. And somewhere in the middle of weekend number twenty-something, I realized something that should have been obvious from the start:
It doesn’t matter how clean your app is. It doesn’t matter if it color-codes your tasks, gives you voice reminders, or rolls them in honey and molten candy. At the core of it, every productivity app offers the same value proposition: “You can store your todos here.”
And that is not enough.
December 2017. The familiar sinking feeling of year-end panic.
I looked at the year that had just gone by. Where had it gone, exactly? I’d worked, sort of. I’d planned a lot. I’d downloaded a lot of apps. I’d done maybe half of what I said I was going to do, and the other half was still sitting there, untouched, mocking me.
For once, instead of reflexively Googling “best todo app 2018,” I did something else: I stopped to think.
And one thing immediately leapt out at me.
The most productive I’d ever been was when I was working for someone else.
When I was working at an office, at a full-time job, things got done. Almost on autopilot. Not because I was a different person back then, but because there was no other choice. If I didn’t do the work, somebody would notice, and I would have to explain myself.
When I quit my full-time job to work for myself, the day stretched out in front of me every morning, seemingly interminable. Tasks expanded to fit the time available. With nobody to answer to, I answered to nobody.
My first instinct, like any sensible procrastinator, was to outsource the problem to my friends. The hapless people I bullied or bribed into being my “accountability buddy” were busy, kind, and very bad at it. They’d check in for two days. Then life would happen to them, and it would quietly peter out. And when I showed up with elaborate excuses for why my work hadn’t been done, they didn’t have the heart to call me on it.
Friends are too nice. That’s their whole problem.
I needed something else. Something consistent and hard-nosed.
(dramatic music)
I needed a Boss.
I launched Boss as a Service on a whim. It worked.
On January 8, 2018, I put up Boss as a Service on Product Hunt. I had a landing page, a payment link, and approximately zero idea what I was doing.
The first customer signed up exactly one hour after launch.
As of 2026, they are still with us.
We launched on Product Hunt. 212 people thought this was a good idea!
A horror movie, and Hacker News.
A few months later, I was sitting in a movie theater watching Hereditary — which, for those who haven’t seen it, is the kind of film that makes you forget you have a phone, because you are too busy quietly losing your mind in the dark.
Halfway through, my phone started buzzing.
I tried to ignore it. Phone people in movie theaters are the worst people. I was determined not to be a phone person in a movie theater.
Then it buzzed again. And again. And then someone next to me gave a loud, long-suffering sigh, and I gave up and snuck out to the lobby.
Twitter mentions. Stripe notifications. Emails. Texts from friends who’d seen something on Hacker News. The page was on the front page. Then it was at the top of the front page.
By the time I got home, hundreds of thousands of people had visited the site, and hundreds had signed up.
Technically, there was no “we” at the time. It was just me, my laptop, and a very full inbox.
I sat on my kitchen floor and answered emails until the sun came up. I’d think I’d written to everyone at least once, refresh, and find thirty more people had signed up. Then fifty. Then more. It only got worse as the night wore on.
That night, I shut down signups, and put up a waiting list.
The real horror of the evening, of course, was my inbox.
Hiring for a job nobody had heard of.
For a while, a much longer while than I should have done, I tried to do all of it myself. Every check-in, every message.
That obviously wasn’t going to scale. So I started hiring.
This turns out to be an unusual recruiting brief. “Caring whether or not a stranger hits their goal” is a weird thing to screen for in an interview. People would hear what the job was, and ask, “Wait. Bugging people to get their work done. This is a real job?”
It took a lot of trial and error to find the right people — people who could be warm and stubborn at the same time, who could call out an excuse without making the user feel terrible about themselves, and who got a small, quiet kick out of seeing a stranger hit a goal they’d been avoiding for months.
The team is the reason this whole thing works. I won’t stop saying it.
Today.
It’s 2026. The list of things people have done with us poking at them has grown long. Novels finished. PhDs defended. Careers switched. Businesses started. Weddings planned. Thirty pounds lost. Things shipped that had been “about to ship” for years.
People still ask me what it’s actually like to be someone’s Boss.
Honestly, it’s hard to describe. Do we feel weird pushing someone to go to the gym at 7am despite their most creative excuses? Maybe a little. But mostly we don’t, because we know that’s what they came here for.
Boss as a Service is not for everybody. But for the right person, the chronic procrastinator with real ambition, the founder who works better when someone is watching, the academic with a deadline they keep avoiding, the person with ADHD whose own brain is the unreliable narrator of their day, it works.
We push people, hold them to what they said they’d do, and applaud when they get there. Small private celebrations break out in our team chat when a long-time client hits something big.
And, more than I expected when I was building a tiny weekend project in 2018, we love our work.
Some of the team. We’re very nice. We will still ask you about that deadline.