Sahil Lavingia has had just three jobs over a 15-year career in tech.
The first was as the second employee of Pinterest. The second was by founding the startup Gumroad, a successful, famously lean company that makes it easy for content creators to sell digital goods. The third? As an unpaid contractor supporting the Department of Veterans Affairs in a role facilitated by the Department of Government Efficiency (DOGE), a fact recently revealed in a Wired piece.
One of these things is not like—and is far more controversial than—the others.
But Lavingia, who chose not to speak to Wired but reached out to me after I drew attention to the piece, makes no excuses for his decision to join DOGE’s tidal wave of on-the-fly federal contractors. He says he’s able to work without pay because of Gumroad’s success—and that he is driven by a sense of mission.
“The reason I did it is, I think, the impact I can have,” he explains. Lavingia says that in the private sector, technical employees can have between six and seven figures of financial impact over their lifetime. If they’re a successful startup founder like he is, maybe that number is larger. “But in the government, I really believe that I can have billions of dollars of positive impact just by being technically minded.”
To hear it from Lavingia, the Elon Musk-backed DOGE was a shortcut in a direction he already saw himself going. Years ago, during the Obama administration, he applied to the United States Digital Service, the predecessor organization to DOGE, only to find the hiring process arduous. While he officially works for the VA, DOGE gave him an inroad into government work that didn’t force him to go through a complicated vetting process.
“They just sent me to the VA,” he says. “They just kind of helped me find the job. Which is great—I’m proud of that.”
Reflecting his tongue-in-cheek stance that DOGE is “a glorified temp agency for software engineers,” he got in through the side entrance, offering his services to the cause of government efficiency.
“I’m basically taking Elon at his word,” he admits.
Wait, doesn’t he run a company?
Lavingia’s decision to moonlight—not exactly unheard of in DOGE circles—doesn’t necessarily tie to his primary gig. But he suggests that it might have inspired his recent decision to open source Gumroad. After all, it matches what he’s proposing with DOGE.
“I think we should open source all the code that we write,” he says of his VA work. “And I think that if we did that, I’m not saying people will agree with us, but at least people will see what we’re doing.”
His VA side hustle comes at a time when Gumroad itself is going through some major structural changes. Last year, the company rebranded its corporate structure as Antiwork, inspired directly by a popular Reddit community of the same name. As part of its restructuring, it began putting its various apps on GitHub, including Gumroad.
(The announcement taking Gumroad open source had some odd timing, hitting on the same day as the Wired story; Lavingia claims it was unintentional and unfortunate.)In one sense, this was a positive move for tech fans who run web apps and other software on their own infrastructure. Now they have a new tool at their disposal, and Gumroad has pledged to make it easier for them to install and maintain its code in the coming months. But the launch raised questions, in part because the license wasn’t purely open source. With limits on the upside for commercial enterprises, tech users were skeptical.
In response to the feedback, almost on a whim (“I just kind of woke up one day, and I was like, ‘Fuck it, let’s just do the thing’”), Lavingia decided to move the Gumroad code base to the MIT license.
That license, which companies such as Netflix and Apple have used to support their empire building, essentially allows users to do what they want with code without any requirements or limitations on its commercial use. Unlike the equally well-known General Public License, it does not require the creation of open-source derivative works.
There are technical reasons for the licensing decision that go beyond helping a few self-hosters. Gumroad is a prominent example of a complex code base built on the Ruby on Rails framework, something Lavingia claims there are only limited examples of in the commons. From an AI standpoint, he says, this creates a knock-on effect where providers of large language models are less helpful with Rails than with competing frameworks like React.
Internally, Antiwork aims for Gumroad to get 100,000 stars on GitHub, a number he freely admits is arbitrary. “But what matters is it’s a good proxy—did we actually build something people use, fork, and get value from?”
(It’s currently at 5,700 stars.)
Lavingia says the timing of his work at the VA is coincidental, but it helped inspire his thinking about open sourcing. Simply put, in a climate where equipment is often purchased through a complex bidding process, federal agencies have more flexibility with open-source tooling.
He uses the example of Drupal, an open-source content-management system that is ubiquitous throughout the government and enterprise, but has a reputation among tech enthusiasts of being an older framework.
“People probably in startups would not say Drupal is their first choice, but what is really good about Drupal is that it’s MIT,” he says. “It’s open source, it has a lot of packages and extensions. And it’s probably no coincidence that the government runs on Drupal for a lot of its CMS needs instead of some commercial proprietary thing.”
One could see an automation-minded coding whiz like Lavingia modernizing the VA’s stack around more efficient tools. But as the security-card mechanisms in many government-procured laptops highlight, federal agencies are a different beast.
A startup lifer’s view of the VA
Much of what has been written about DOGE—the push to get employees into sensitive systems, the aggressive attempts at layoffs, the weekly emails—has not endeared the work to the public, and Musk recently took a step back from the endeavor.
What people have heard about DOGE, they don’t like. A recent New York Times poll analysis found survey respondents favored the idea of improving government efficiency, and even the idea of DOGE, but not the way it was being done.
But hearing a first-person perspective of what’s happening on the ground from Lavingia is nonetheless revealing. He’s someone who has gone from being the big fish in a tiny pond to just another person in an agency that counts more than 400,000 employees on its payroll—though, as with elsewhere in the federal government, it is also seeing cuts.
Now that he’s there, he says he finds himself surrounded by people who “love their jobs,” who came to the government with a sense of mission driving their work.
“In a sense, that makes the DOGE agenda a little bit more complicated, because if half the government took [a buyout offer], then we wouldn’t have to do much more,” he says, implying software can replace departing employees. “We’d just basically use software to plug holes. But that’s not what’s happening.”
Lavingia’s skills with automation, which have helped keep Gumroad lean, are what he hopes to bring to the VA. But when it comes down to it, what he’s found is a machine that largely functions, though it doesn’t make decisions as fast as a startup might.
“I would say the culture shock is mostly a lot of meetings, not a lot of decisions,” he says. “But honestly, it’s kind of fine—because the government works. It’s not as inefficient as I was expecting, to be honest. I was hoping for more easy wins.”
In contrast to DOGE’s shadowy reputation, Lavingia has made a case for transparency. Based on a pledge he received from Musk during a meeting, Lavingia has been open sourcing his VA work, creating tools that can generate org charts and detect compliance with the president’s executive orders.
If you aren’t a fan of DOGE’s work, the open-source code, while useful for transparency, probably won’t make you feel any better about Lavingia’s work at the VA. The compliance code, for example, is effectively a Python script that hooks into OpenAI servers hosted on Microsoft Azure, detecting whether a federal agency’s communication references chief diversity officers, pronouns, or WHO (World Health Organization) partnerships.
However, Lavingia makes it clear that DOGE has limits, especially thanks to the court decisions and palace intrigue that have removed much of its bite. Ultimately, he argues, it has become a way for roving engineers to get an up-close view of how government works—a “McKinsey for the government,” as he puts it.
“I think DOGE both gets too much credit and too much blame,” he says. “Blame the people who actually have the authority to make the decisions. It’s like when people say billionaires are evil. I’m like, well, maybe—but really, the people at fault would be the lawmakers, right? I don’t know.”
Lavingia strikes me as someone who genuinely cares about the work he’s doing, but who thinks about it like a software engineer. There may be a case for startup lifers to swoop in and out of government, sharing the latest technical innovations with a complex beast in dire need of more efficiency. But the move-fast-and-break-things style may simply be too swift and damaging when essential government services are on the line.
A fork in the Gumroad?
No matter how Lavingia sees things from a day-to-day perspective, the truth is that people who feel betrayed by Gumroad’s association with DOGE have a new reason to go with another creator-friendly tool.
But it’s not the first knock against the service. Its traditional laissez-faire approach to content moderation—controversially, the site is the digital storefront of onetime Adult Swim sketch comic Sam Hyde, notorious for his alt-right ties—has long raised eyebrows.
The company’s heavy use of automation has also created problems for users concerned about customer support. Evan Hildreth, a writer and programmer, recently expressed frustration with the platform’s changes, and his inability to reach a support person that wasn’t an LLM. Even with the licensing changes, he felt like he could no longer trust the platform.
“The changes to email and memberships really shook my confidence in the product itself,” he said. (Lavingia says Gumroad is working to hire additional customer support staff.)
And more recently, the platform has started to limit not-safe-for-work content, with Lavingia suggesting to TechCrunch last year that an unnamed supplier required the stricter approach.
But even considering all that, Lavingia seemingly hadn’t taken into account one key aspect of open sourcing that the MIT license could allow: the potential of folks turned off by his moonlighting gig creating their own version of Gumroad by forking the code and continuing development independently. When I pose the question, he isn’t entirely opposed. He admits that the “brutal form of capitalism” the MIT license allows for might force Gumroad to compete a little harder—or, perhaps, become more community-oriented, like WordPress.
“I kind of want that, almost. I want to move on with my life,” he says. “If someone launches Blueroad.com, or something worse on the right? Whatever.”
While Gumroad—a small company with outsize impact on the creator economy—isn’t going away, going open source nonetheless seems like something Lavingia has been preparing to do for a while.
“Gumroad is now 14 years old. So maybe the analogy is, ‘My kid’s going off to college, and it’s not my problem anymore,’” he says. “And maybe this means Gumroad will get even weirder in the future, right?”
Given the current context, it’s already off to a weird start.
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