It is probably fair to say that most of the people reading this, know what Gumroad is and are aware of the products their are offering. However, I would still like to take the chance to give a brief introduction. Gumroad owns and operates an online service through which users can buy and sell digital goods, through which it has made a significant impact on the growth and establishment of the creator economy. It got founded in 2012 by Sahil Lavingia, who was the second employee and first designer at Pinterest from 2010-2011. Gumroad received a total of $16.1M in funding throughout the years. The most important funding round happened in 2021, when Gumroad did an Equity Crowdfunding round, raising $5M from over 7,000 investors through a platform called Republic. Why was this one so essential? Well, without it, it is questionable if Gumroad would still exist today, as it ran out of money multiple times (and had to lay off the whole team twice), and even more critical, Gumroad screwed over the creators selling on its platform through a price increase, which Sahil Lavingia first tried to keep as a secret, but creators found out, raised their voices, and suddenly Gumroad decided to send out an email to all creators informing them about the pricing changes.

But that is not it. Gumroad left adult creators worried after it suddenly banned most NSFW content, it faced a massive backlash over alleged NFT ambitions, and in general Sahil Lavingia is known for his controversial takes which he is posting on X. In 2019, Sahil Lavingia shared his story of downscaling his dreams of starting a billion-dollar company. Personally, I never felt the urge to build a billion-dollar company, and to be honest, if you feel that kind of urge, it is simply megalomaniac.

Sahil Lavingia always created the impression of exemplifying the startup hustle culture. He jumped on every single hype train over the past years, and therefore, it is no wonder that he went all in on AI and LLMs, to the extent that it seems like that he has replaced Gumroad's support staff with an AI chatbot, that delivers a worse experience for users and customers. And beyond that, it seems like Sahil Lavingia is proud of that achievement as he mentioned on a podcast from February 2025, that he 'automated all the stuff, has enough cash in the bank, and what he should do next'.

Although, Gumroad's most recent news appeared to be positive, as it announced that it is becoming Open Source (while it is not), I was more hooked by a story from WIRED, about Elon Musk's so-called Department of Government Efficiency (DOGE), and how it got involved with the Department of Veterans Affairs (VA), where Doge had the plans to fire tens of thousands of employees. According to that article, on March 25, tech staffers and contractors at the VA noticed an unfamiliar name trying to push changes that could impact VA.gov code.

Guess who that unfamiliar name was.

Sahil Lavingia.

The founder and CEO of Gumroad, the hustler and tech-bro with zero government experience, is now also part of DOGE, who shared his plans to digitize the agency on Slack with VA employees, as well as trying to use an AI tool called OpenHands to write code for VA's systems. WIRED reached out to Lavingia with questions about his work at the VA. He responded via email saying "Sorry, I'm not going to answer these, besides to say I'm unpaid. And a fan of your work!".

To be honest, after looking into Lavingia's vita, it is no surprise that he joined the epitome of the worst of startup hustle culture. Nothing justifies the actions of Elon Musk, Donald Trump, and Doge, nothing, absolutely zero. Seeing those actions and still deciding to join and follow them is beyond pathetic, and simply unacceptable.

I have never used Gumroad for my endeavors as a creator, in terms of selling any kind of products, however, I was an affiliate of a couple of products other creators sold through the platform. Most of them left Gumroad based on the various controversies it created over the course of the past years. However, Sahil Lavingia's involvement in DOGE is now the final sign for me to delete my account completely, and leave the platform behind. I liked the idea of Gumroad because I like apps, tools, and services that were built to give creative minds the possibility to pursue their dreams and create a living from their passions.

And I would like to point out a perspective Ernie Smith captured in his newsletter Tedium, which is that there is a real opportunity to take away the reins from middlemen who extract value rather than add it by leaning into things we host ourselves.

Till next time! 👋‌‌‌‌

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