The story of the digital content-sharing platform Gumroad challenges every aspect of the received wisdom about building successful companies. After it almost went under, founder and CEO Sahil Lavingia decided to pare down to the essentials rather than walk away. Then he took his characteristic counter-intuitiveness further and left Silicon Valley for Provo, Utah. Through it all, he never lost sight of what he was trying to do and his joy in building products. Gumroad is now thriving, with $175 million in volume last year, all thanks to Lavingia’s willingness to take a different path to success.

Among the many things he’s learned along the way are the value of getting a fresh perspective and the virtue of patience – even when it’s unexciting. Commitment is often overlooked in heady times, but as he told me, “A lot of people are so concerned about catching the next train because it's the last one. They think it's over. But there are many more trains – just make sure you're at the train station. That's the important thing.” He had a lot to say about this, as well as Gumroad’s unique equity and dividend model, which it’s now sharing with other companies.  

Other topics we touched on include:

• His long history of taking unconventional paths

• How he broke into the startup ecosystem

• Why building more than one product at a time is better than building a single perfect product

• How to get into the wild world of AI startups

• Making difficult business decisions for survival

• Appreciating the opportunity to continue doing what you love

• The power of equity and incentivizing for the future

• And so much more

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Where to find Sahil Lavingia:

• Sahil’s site: https://sahillavingia.com/ 

• LinkedIn: https://www.linkedin.com/in/sahillavingia 

• Bluesky: https://bsky.app/profile/shl.bsky.social 

• X: https://x.com/shl

• Instagram: https://www.instagram.com/shlpaints/?hl=en

Where to find Eric:

• Newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://ericries.carrd.co/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 

• Podcast: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://ericriesshow.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 

• YouTube: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.youtube.com/@theericriesshow⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 

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In This Episode We Cover:

(03:15) Singapore and America as the ultimate high-growth startups

(04:50) How Sahil first encountered entrepreneurship as a teen graphic designer

(07:15) The new meaning of “knowledge work” 

(11:10) Sahil’s impressions of American possibility after growing up in Singapore and returning

(16:33) Sahil’s history of deviating from the expected path

(19:27) Gumroad’s path from a failed funding round in 2015 to profitability in 2023

(24:17) How Sahil broke into the startup ecosystem and his first iPhone app 

(27:41) Sahil’s advice for people looking to break into the new rising tide of AI

(30:38) On not putting all your eggs in one product basket

(32:59) How and why he left Pinterest

(34:48) Surfing and treading water as business cycles

(41:36) Overnight successes that are really a long time in the making

(45:59) How Sahil started Gumroad

(49:19) Reconciling getting fired with successfully raising money for a new company

(54:26) The failure to build a billion-dollar company

(1:03:42) How to prioritize survival

(1:06:33) The pivotal decision to leave San Francisco for Provo, Utah

(1:08:11) The current state of Gumroad 

(1:11:22) How Gumroad is structured to solve some of the classic business problems: equity, ownership, dividends

(1:13:53) Incentivizing for the long-term

(1:22:12) How Gumroad is helping other companies copy their model 

(1:25:16) Lightning round

You can find the transcript and references at ⁠⁠⁠https://www.ericriesshow.com/⁠⁠

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Eric may be an investor in the companies discussed.