The Trump-Musk Fallout + A DOGE Coder Speaks + ChefGPT
This week, Kevin and Casey discuss the sudden breakdown between President Trump and Elon Musk, whose disagreements over the policy bill before Congress quickly erupted into an all-out feud. Then, an ex-DOGE coder explains what it was really like to work inside the Trump administration’s cost-cutting arm. And finally, the former New York Times restaurant critic Pete Wells explains why some chefs are turning to A.I. for inspiration.
Guests:
Sahil Lavingia, C.E.O. of Gumroad, who spent 55 days working for DOGE
Pete Wells, New York Times restaurant critic from 2012 through 2024
Additional Reading:
If Elon Musk and President Trump Divorce, Who Gets Silicon Valley?
This Year’s Hot New Tool for Chefs? ChatGPT.
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#256 – Debate: Elon Musk, Billionaires, Ethics, and Role Models with Sahil Lavingia and Justin Jackson
Sahil Lavingia (@shl) and Justin Jackson (@mijustin) join Courtland (@csallen) and Channing (@ChanningAllen) for a special debate-style episode. It's four dudes talking about Elon Musk. What could go wrong?
Follow Sahil on Twitter: https://twitter.com/shl
Check out Gumroad: https://gumroad.com/
Follow Justin on Twitter: https://twitter.com/mijustin
Check out Transistor.fm: https://transistor.fm/
#237 – The Minimalist Entrepreneur with Sahil Lavingia of Gumroad
Today I'm talking to Sahil Lavignia (@shl) about what indie hackers can learn from his new book, The Minimalist Entrepreneur.
Get a copy of Sahil's new book: on Amazon
Follow Sahil on Twitter: https://twitter.com/shl
Check out Gumroad: https://gumroad.com/
Equity Crowdfunding is making the private markets public
Hello and welcome back to Equity, TechCrunch’s venture capital-focused podcast, where we unpack the numbers behind the headlines.
For this week’s deep dive, the Equity team brought on Gumroad CEO Sahil Lavingia and Hustle Fund General Partner Elizabeth Yin to talk about equity crowdfunding. It’s been about a week since the SEC increased the equity crowdfunding cap from $1.07 million to $5 million, creating the perfect opportunity to go beyond the dollar amount and understand how the change impacts founders, venture capitalists, retail investors, and future fund managers.
Here’s a brief rundown of the show:
We talk about the basics of this new SEC regulation, and understand which platforms might be leading the pack for these bootstrapped campaigns. Indiegogo’s founder wrote an op-ed grading the new regulations on the site.
Some banter on Gumroad’s 12-hour campaign that led to a successfully crowdsourced $5 million for the company. Lavingia talks about his decision to crowdfund a round in his company, why it made sense for the company, and what it will take to make this raise mainstream.
Of course, Yin shared a ton of helpful nuggets around crowdfunding, providing a venture capital perspective that was still bullish on growing the amount of check-writers in the ecosystem. Some recent equity crowdfunding campaigns have shown that there are thousands of individuals willing to fund the enterprises they want to see succeed. Juked.gg is one such example.
There are also notes on the Testing the Waters dynamic that could usher some wiggle room to early-stage founders thinking about this.
Will equity crowdfunding supplant venture capital, or will it merely augment it? Our discussion leads us to ponder both possibilities. What seems clear is that equity crowdfunding could widen the band of companies that are "backable," if not the band of companies that traditional venture capital players find enticing.
And we end with a whole bunch of meta debates, from the role of the platform in vetting campaigns. As with every innovation, including crowdfunding itself, there will be fraud and failure. But if there will be enough bad news to limit consumer interest is far from certain.
This is one of those nerdy topics that gets us really excited about the future of dollar allocation and startup creation. We hope you love the show and leave with a better understanding of what’s ahead.
Credits: Equity is produced by Theresa Loconsolo with editing by Kell. Bryce Durbin is our Illustrator. We'd also like to thank the audience development team and Henry Pickavet, who manages TechCrunch audio products.
Learn more about your ad choices. Visit megaphone.fm/adchoices
Sahil Lavingia on Gumroad’s groundbreaking equity crowdfunding raise, lessons from a decade-long startup journey, insights on rolling funds & more | E1188
Check out Gumroad: https://gumroad.com
FOLLOW Sahil: https://twitter.com/shl
FOLLOW Jason: https://linktr.ee/calacanis
20VC: Sahil Lavingia on Rolling Funds and Their Impact on The Future of Venture, How To Evaluate Market, Team and Product, The Value of Party Rounds & The Pros and Cons of Multi-Stage Funds Investing at Seed
Sahil Lavingia is the Founder and CEO @ Gumroad, the company that helps creators do more of what they love. With Gumroad, Sahil has raised funding from an all-star list of investors including Accel, Kleiner Perkins, First Round and then Max Levchin, Chris Sacca, Ron Conway and Naval Ravikant on the individual side. However, most recently Sahil has made waves launching one of the first rolling funds on AngelList with his being $6M per year. In the past, Sahil has backed the likes of Lambda School, Figma, HelloSign and Haus to name a few.
In Today's Episode You Will Learn:
1.) How did Sahil make his way into the world of startups and angel investing? What were his biggest takeaways from being employee #2 at Pinterest? How did that experience impact his mindset?
2.) Why did Sahil decide to make his new fund an AngelList rolling fund? How is it structured? Does Sahil think this will represent a seismic shift in early stage investing? Is this a game of the 1%? Why does Sahil think early-stage remains so undervalued? How will this impact Series A pricing?
3.) How does Sahil assess his own price sensitivity today? How does Sahil think about the right way to turn down a founder? Where do many go wrong? How does Sahil feel about the rise of pre-empted rounds? How does Sahil advise seed founders with offers from multi-stage firms?
4.) What does Sahil believe founders care most about today in their investors base? How does Sahil think about investor brand and distribution? How does Sahil analyse the pros and cons of party rounds? How does Sahil advise founders on constructing their early cap table?
5.) How does Sahil think about his relationship to risk and to money? How did Sahil deal with it when his investors wrote off his company? How did Sahil feel about the weight of expectation placed on his shoulders at such a young age? How did he deal with this?
Items Mentioned In Today's Show:
Sahil's Fave Book: How to Win Friends and Influence People
As always you can follow Harry and The Twenty Minute VC on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
#134 – Code vs No-Code with Ben Tossell of Makerpad and Sahil Lavingia of Gumroad
The no-code movement is picking up steam, with more people than ever building apps and businesses without knowing how to code themselves. Ben Tossell (@bentossell), the creator of Makerpad, is betting his business that no-code is the future of work. However, Sahil Lavingia (@shl), the founder of Gumroad, isn't so sure that code. In this episode, I hosted a lively discussion between these two thoughtful bootstrappers about code vs no-code. Which approach should a new indie hacker should take? What gaps in the market are opening up due to the changes in tooling landscape? And what does the future hold?
Transcript, speaker information, and more: https://www.indiehackers.com/podcast/134-ben-tossell-and-sahil-lavingia-on-code-vs-no-code
#100 – From Aspiring Billionaire to Indie Hacker with Sahil Lavingia of Gumroad
After leaving his post as employee #2 at Pinterest, a teenage Sahil Lavingia (@shl) raised millions in funding from high-profile Silicon Valley to build a unicorn startup that could change the world — Gumroad. Today he lives in tiny Provo, Utah, spends much of his time learning to write and oil paint, and runs Gumroad as an indie business with the goal of making himself happier. In this episode we talk about what happened in between, and the lessons Sahil learned that can help every indie hacker create better lives for themselves by building more "successful" businesses.
Transcript, speaker information, and more: https://www.indiehackers.com/podcast/100-sahil-lavingia-of-gumroad
Sahil Lavingia on “failing to build a billion-dollar company”
Abadesi talks to Sahil Lavingia, founder and CEO of Gumroad, an online platform that enables creators to sell directly to their customers. Sahil is a very authentic founder who is not afraid to speak uncomfortable truths, as you’ll see in the interview.
They talk about...
His journey starting Gumroad and what happened when they realized the company wasn’t going to be as successful as they had hoped
Sahil was very young when he started Gumroad (he’s only 26 now!) and had worked a couple big tech companies where he saw that “there’s a lot more duct tape in the industry than people realize.” He recounts the ups and downs of the company and what precipitated the events described in his now-famous article.
“We raised over ten million dollars from a great list of investors and realized when we were trying to raise a series B that that was unlikely to happen and went from 20 to 5 employees to get to profitability. Then we went from 5 to 1 when I could run the company by myself but luckily we’ve been able to grow the team again. Even though we’ve processed over $200 million for creators, eight years later it still feels like we’re in the first inning, as people say.”
He says that a lot of people think they can be the exception to the rule that most companies don’t succeed as much or as fast as they hope they will, and that you should remember that “you’re probably closer to the mean than you think.”
Why relationships in Silicon Valley are so transactional
Sahil talks about the difficulty of building deep relationships on a personal level in the Valley and how that changed when he moved to Provo, Utah, where he was able to find a support network. He says that people were eager to meet with him when he was perceived as successful but not so much when the company wasn’t doing well.
“There’s this transitive property of trust, where if someone that someone trusts gives you an intro to them you’re sort of guaranteed to meet them. I think network-building is better in Silicon Valley than anywhere else but it’s difficult to meet with someone multiple times and build a deep relationship without a clear agenda that’s going to help [one or the other].”
Dealing with the psychological ups-and-downs of having your identity as a founder so wrapped up in the fate of your company
“On a personal level, you do suffer, because you realize how much you’ve invested in your company and how little in yourself.”
He talks about the difficulty of admitting that your company isn’t doing as well as people think and how to find help as a founder:
“The only way you can get support is to be open about the thing that you need help with, and when your identity is so wrapped up in something that isn’t working, it’s difficult to be open about that.”
He comments on the trend of watching successful founders try to find themselves in public and in real-time on Twitter after their exits:
“They have all this time and all this money and they feel anxious and don’t know how to spend their time and don’t know what’s next for them. You realize, that’s my future if I don’t figure this stuff out.”
His philosophy of technology, both personally and at Gumroad
“Pick a couple things that you really believe in strongly and do the boring, standard things for everything else. The things that you do differently, you really want to invest in doing them differently in the right way. It’s easy to fall into the trap of doing things differently the wrong way.”
Why he believes so strongly in in-person connection
Even with the advent of technologies and tools that make it possible to connect over long distances, he points out that the physical world is much higher fidelity than the digital one:
“Technology is great and getting better but nothing replaces being in the same place as another person and breathing the same air.”
“Gumroad is great, but if it’s not making people’s lives physically better, it’s not worth it.”
We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. Big thanks to Embroker and Vettery for their support. 😸
Companies and Products Mentioned In This Episode
GitHub — The world’s leading software development platform.
Notion — Increase your team intelligence.
Slack — Be less busy. Real-time messaging, archiving and search.
Wikipedia — The free encyclopedia.
YouTube — The video-sharing site.
Zoom — Cloud videoconferencing and simple online meetings.
SaaS Fundraising: How Sahil Lavingia Raised $8M for Gumroad
Built in a weekend. 50,000 visitors on Monday. Zero dollars spent on marketing. Sahil Lavingia built the first version of Gumroad over a single weekend and posted it on Hacker News. Product-led growth did the rest - every creator sale exposed Gumroad to buyers who were creators themselves.
Sahil shares how he went from Pinterest's 4-person team to SaaS fundraising $8M for his own creator economy platform, why he deliberately ignored customer acquisition in favor of building a product-led growth engine, and what he learned about leadership as a 22-year-old first-time CEO.
Gumroad's SaaS fundraising journey included a $1M seed round and $7M Series A while the team focused entirely on product. The SaaS go-to-market strategy was simple: make every transaction an acquisition channel.
🔑 Key Lessons
🛠️ Build a weekend MVP to validate product-led growth potential: Sahil built Gumroad in two days. The prototype was simple - upload a file, set a price - but it attracted 50,000 visitors and proved demand.
🚀 Let every transaction drive growth automatically: Gumroad grew without marketing because every sale exposed the platform to buyers. Many buyers were creators who could use Gumroad themselves, creating a self-reinforcing loop at zero cost.
💰 Let VCs come to you by building in public: Sahil raised a $1M seed round to buy time, then focused on building. VCs reached out after seeing Gumroad's progress, leading to a $7M Series A without aggressive SaaS fundraising.
🧠 Communicate the why, not just the what, as a first-time CEO: Sahil learned that leadership requires explaining reasoning behind decisions proactively. Self-awareness and giving feedback mattered more than technical ability.
📉 Accept that growth compounds slowly at first: Sahil expected a 30x better product to attract 30x more users immediately. He learned to keep building toward the vision rather than reacting to short-term behavior.
🔄 Abstract away complexity to deepen engagement: Gumroad evolved from raw file uploads to content-type experiences. Creators stopped thinking about zip files and started thinking about selling a book.
Chapters
Sahil's background and what Gumroad does
Growing up in Singapore and moving to the US
How Sahil joined Pinterest at four people
Why Sahil left Pinterest to start Gumroad
Discovering the problem of selling digital files
Building the first version of Gumroad in a weekend
Launching on Hacker News and reaching 50K visitors
Why Sahil focused on product instead of acquisition
How Gumroad's product-led growth loop works
Evolving from raw files to content-type abstractions
Challenges of being a first-time CEO at 22
SaaS fundraising: raising the $7M Series A round
Long-term vision for Gumroad as a creator platform
Lightning round
Resources
Full show notes: https://saasclub.io/9
Join 5,000+ SaaS founders: https://saasclub.io/email