My name is Philipp and you are reading Creativerly, the internet corner where I unpack my musings, curate and write about noteworthy apps and software, and explore the latest trends in design and tech.

Hey and welcome to Creativerly 321 👋

Throughout the past six years of writing this newsletter every single week, it just happened a couple of times that I had no idea what to write for this intro section. While preparing this issue of Creativerly, I felt like that again, which is the reason, this intro section is super short, quick, and does not contain any kind of thoughts, ideas, or insights.

I hope you still enjoy the rest of the newsletter.

The Dark Side of Gumroad: How Sahil Lavingia got involved with DOGE

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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 quick 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 important? 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 important, 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 huge 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 podcasts from February 2025, the 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.

Read the full post here:

The Dark Side of Gumroad: How Sahil Lavingia got involved with DOGE
The controversial, hustle culture-shaped career of Gumroad’s founder found its peak, as Sahil Lavingia joins Elon Musk’s DOGE and its plans to digitize the Department of Veterans Affairs.
CreativerlyPhilipp Temmel
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Fresh Updates & News

tldraw raises $10M Series A from Lux Capital →

tldraw, one of the most popular canvas tools, especially known for their infinite canvas SDK that is used by multiple productivity and note-taking apps out there, just announced that they have raised a $10M Series A led by Lux Capital and Definition. This investment round follows tldraw's first year of sales which generated $1M in revenue through license deals with ClickUp, Autodesk, Padlet, and others. The company is now planning to use the new investment to help other companies get started and become successful with tldraw's SDK easier and faster, they also plan new modules, such as integrations with LLMs, as well as growing the team, as they are looking for engineers, designers, or product thinkers.

WordPress launches a free AI-powered website builder →

WordPress is trying to keep up with all the innovation that has been going on in the website builder space by introducing a new AI-powered website builder that allows users to create a functioning website using an AI chat-style interface. This new feature will be available to WordPress users for free and is very much targeted at entrepreneurs, freelancers, bloggers, and other who need a professional online presence, as WordPress states.

Mental Wealth

❯ A Few Notes on Problem Solving – “Someone asked a question about how to get better at problem solving. It got me thinking: how does problem solving work? It seemed like an interesting question to try to answer. I’m going to gear this post toward solving technical problems, but some of this may apply more broadly.”

❯ How to Make Decision Fatigue a Thing of the Past – “You know that feeling at the end of the day when someone asks, “What do you want for dinner?” and your brain short-circuits? That’s decision fatigue—and it’s not just dinner. It’s the dozens (or hundreds) of micro-decisions we make from the moment we wake up that quietly drain our energy and clarity.”

❯ The hidden power of unanswerable questions – “In our data-driven age, everything seems designed to hand us solutions. Every day, Google processes a staggering 13.7 billion searches — nearly 5 trillion a year. Amid the growing sea of AI chatbots, ChatGPT alone handles more than a billion inquiries daily. Surrounded by this avalanche of answers, we charge forward toward certainties, rarely pausing to notice the quiet but powerful moment before — the moment we pose a question. Though we ask questions all day long, they have become little more than automatic triggers for retrieving information, their real potential flattened by our fixation on quick answers.”

❯ Mo prompts, same problems. – “Since the debut of Terminator 2, we’ve all been primed to watch for signs of the impending skull-crushing robot apocolypse. As we’ve drawn closer to that pivotal moments of robots replicating forms of human intelligence and motor skills, the horror isn’t about destroying human kind, but another kind of doomsday—ending our careers. What was once dubbed the future is not present day. We’ve been here for a while now and that reality was abruptly introduced to the world through an internal company policy memo that reads “Start using AI, not more humans, now.””

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Appendix

❯ ICYMI

The note-taking app sector is crowded. While the initial hype around those apps has fainted, taking notes is still a powerful practice. So, what matters most when choosing a note-taking app?

❯ Quick Bits

Till next time! 👋‌‌‌‌

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