Build Your Own Gumball

Two weeks ago, I found myself on an hour-long interview with a guy who I had kind of raked over the coals a few weeks prior. It was a good conversation, and he was remarkably candid.

From a business standpoint, Gumroad CEO Sahil Lavingia was honest with his desire to help reset the conversation that had broken out about the platform his company built.

Of course, that wasn’t the only thing we talked about—as a recent Fast Company piece I wrote highlighted, he found himself working at the Department of Veterans Affairs at the behest of DOGE. If you find that story interesting, I encourage you to read it there—thanks in part to the attention it got, it’s no longer paywalled.

But I wanted to take a step back and talk a little bit about the FOSS part of our conversation, which got a bit overshadowed by his unusual gig. Simply put, even with the attached baggage, I think the flexibility he showed regarding changing Gumroad’s licensing from source-available to plain-Jane FOSS is genuinely a good thing. It shows a willingness to listen to feedback even when that feedback isn’t always friendly.

By choosing to switch to an MIT license, Gumroad is now a much more useful product to a technically minded end user—and it sets up an end-user contract that lets people borrow what they like about the tool and separate out what they don’t.

Even if you disagree with him on how he approaches things like artificial intelligence and government contracting, he’s now given you the right to not necessarily worry about him if you really don’t want to—because you now have the keys to the kingdom, as long as you’re willing to figure out how they work. You can run it without giving him a cut—but you can also contribute back to the broader community, making it so that he is not the primary figure of influence in that community as more people contribute.

But the licensing decision, if nothing else, is significant. We don’t usually see platforms this mature getting a FOSS license this far along in their life.

It’s worth noting, though, that this cuts both ways.

Gumroad’s Self-Hosting Challenge? It’s Old

From a self-hosting standpoint, it’s not quite set up for an easy time at the moment, and will require a lot of command-line work to get it up to speed. Like most modern self-hosted applications, it uses Docker; unlike most of those, Docker is only a small part of the app stack—the current stack is really built to run the main application on bare metal with Dockerized components for the more modular things, like Redis and MySQL. At a time when a lot of self-hosted apps can be launched with a single Docker Compose file, that’s a lot less newbie-approachable than it could be, but they have pledged to make it more friendly over time—which will be a huge asset for end users in the months to come.

“A big investment we’re going to make in the next year is to make it easier to deploy, to open,” he told me. “There’s a lot of technical debt, being an old codebase.”

Ultimately, though, it’s possible, and that is the first step towards resetting something for a new type of audience—one that he didn’t necessarily see as being a purely commercial play, based on our conversation.

“It’s not like, ‘How do we make more money?’ It’s like, ‘How we can make it easier to deploy on AWS?’,” he said.

(He mentioned, as well, that by open-sourcing, he could make it more accessible in government contexts, relevant to DOGE’s mission.)

The Improving State Of Self-Hosting

Over the last couple of years, I’ve done a lot of personal self-hosting of apps. I run my business on tools like InvoiceNinja, which makes it possible for me to send a quick invoice in a matter of minutes. It’s not the most user-friendly thing in the world, but on the other hand, it offers the end user the ability to not be bogged down with aggressive cuts.

I have an app I rely on for time-tracking. For social media stuff. And even for syncing files. When redesigning Tedium a few months back, I replaced a commercial image hosting tool that cost me $300 a year with an open-source proxy tool that costs me nothing beyond of my standard hosting fees. And I see myself switching my email provider to something self-hosted within the next year as well. One look at selfh.st or the r/selfhosted Reddit community shows that it’s come a long way.

And other highly complex apps have improved their game significantly in recent years. Cal.com, which ticked me off so much two years ago that I warned an audience of Hacker News readers against using it after I tried and failed to get it to work over many hours of trial and error, is far more approachable than it once was. They seem to have gotten past the headaches with some improved Docker packaging, and now it’s a tool that’s strong enough that I use it on a daily basis.

And there are opportunities to vibe-code your way out of a paper bag if that’s your thing, too. (If it’s not your thing, that’s OK!) The ability to build custom apps for things only you might really need is one of the more potentially powerful aspects of AI, and it’s one road of many you can go down.

There’s also nothing wrong with spending some time learning how to program if you’re not quite there. Stuff like CodeAcademy and Scrimba can really take the edge off without requiring you to take night classes.

The onramp to this stuff is pretty simple these days: A mini PC, a good internet connection, a level of comfort with a terminal, and a few hours of time is all you need. It’s a way different paradigm from a high-flying consumer-level app, but I think this mindset is gradually inspiring those kinds of apps to be more approachable.

A company like Gumroad seeing this space and wanting to join it is notable—even if it’s not quite as approachable as downloading a single docker-compose file and hitting “run.”

Free Advice: When Offered, Take The Call

My interaction with Sahil was ultimately one where I felt like someone who didn’t have to give me the time to talk about this stuff did. (He literally just had a kid—he has more on his plate than reaching out to an old-school blogger with a taste for washed-out grayscale imagery.)

Recently, a lot has been said about the idea of actually talking to people who you have disagreements with. (If you’re very active on Bluesky you might have seen a debate about this very thing break out just yesterday.)

As a journalist, I talk to people all the time who I might not see eye to eye with on every issue. It comes with the territory. And while I can’t say that I was personally any more excited about DOGE after I talked to him, I did at least grasp to some degree where he was coming from—why someone like him would find this work of interest. It’s important in situations like these to both talk and to listen.

Recently, longtime Tedium contributor David Buck posted a piece where he wrote about his favorite homebrew NES games. It was essentially his personal opinion—but a manufacturer of these homebrew games was so upset that he did not link them that they posted a long rant about how it was a huge setback that they didn’t get a link. Didn’t reach out to us, just had this public reaction about it.

In response, I explained why David didn’t link their site (he didn’t want it to read like a giant sales pitch for games, and ultimately an article isn’t an ad) and gave them an opportunity to get on a Zoom call. They didn’t take it, and I thought that was unfortunate.

Text boxes only go so far when it comes to understanding the perspectives of others. Nothing wrong with getting on a phone sometime.