Below the Line with James Beshara on Smash Notes

#11 — Sahil Lavingia — Solo Journey

Below the Line with James Beshara

Sahil Lavingia is the CEO and Founder of Gumroad, a platform to help creators create more through simple e-commerce and audience tools.

He is also known for insightful and refreshing points of view on Twitter and Medium. To round it out, he’s also a designer, painter in addition to being a technology CEO and writer.

Sahil and I have had similar paths in creation, from tech to design to art, as well as being a founder that has seen almost everything. From being employee #2 at Pinterest to starting his own company, to coverage in just about every magazine, every investor in Silicon Valley wanted to be a part of what he was building to layoffs, then more layoffs, to then being the only person running his company, bordering on depression for a long stretch of time, and now back to a tight-knit team and a business that will bring in over $5m in revenue this year, profitable and actually growing faster than ever.

In addition to the experience he’s had, he’s begun to articulate what it has been like as a creator, and his tweets and essays on the topic, up there with Justin Kan, Eric Ries and a handful of other guests have given people some of the most realistic glimpses of what it’s truly like, and I can’t wait for you to hear this behemoth of an episode.

Episode notes last updated on July 05, 2019 18:43

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Smash Notes summary for this episode

Who is Sahil Lavingia?

Sahil Lavingia is the CEO and founder of Gumroad, a platform to help creators create more through simple ecommerce tools. He is also a designer, writer and painter.

Sahil has gone many ups and downs in his startup career, from raising millions of dollars in venture capital and getting on the Forbes 30 under 30, at the time when every investor wanted a piece of his company, to laying off his entire company but himself, and battling with depression.

Today Gumroad is profitable and is on path to grow faster than ever, but Sahil no longer lives in San Francisco and works out of a shiny startup office. He’s moved to Provo, Utah, and among other things is always happy to share his newly found view on startups and life.

What is living in Provo, Utah like?

Provo is the most conservative and the most religious city in america with over 100k citizens. Crazy mix given it's also a college town. Sahil moved there without any expectation, he wanted to be surprised, and surprised he was!

Why did Sahil Lavingia move to Provo Utah?

When his company, Gumroad, was flatlining, he wanted to work on something he could control and writing fiction was one of them. There was a great class going on in Provo, only available to the local community. Sahil got into the class, so the obvious answer was to pack up and move to Provo to do it.

What's wrong with San Francisco ?

It's a homogenous bubble where every thought you have is reinforced in the same way and you have very little chance to get any non-conforming opinion.

Are religious people terribly misguided?

Religion gives people a framework to live and to enjoy life in the same way as tech obsession fuels the lives of tech workers in San Francisco. A belief system is a set of shortcuts and traditions, and it doesn't need to be justified to add value.

What is the best way to create more?

Shorten the feedback loop between ideation and a final product.

What is the best way to be good at something?

Instead of competing with people at an existing game, create your own game and define the rules, then you can be the best at it by the virtue of being the only one playing it.

What is the major difference in aspirations between San Francisco and Utah?

Both communities believe that creating something is the best way to put energy into the world, but in Sahil's experience while San Francisco crowd aims to achieve massive scale, Utah folks are happiest by making something great which can benefit their local community.

Do you find Provo to be a more creative place than San Francisco?

The competitive nature of San Francisco can push you to create a lot in a short period of time, meanwhile in Utah, while a much less competitive environment, you might actually have more freedom and capacity to create, due to slower pace of living and cheaper rent.

Why did Sahil Lavingia start attending the Mormon church?

Sahil grew up in Singapore, in a Muslim household, but considers himself agnostic. Once he moved to Provo, where the majority of the town goes to church, it seemed like there'd be no better time to learn more about the Mormon views. In many ways, he'd found church to be like the alcoholic anonymous, a great place to learn more about people and to help each other.

Why go to Church even though you do not believe in the faith?

According to Sahil, Church is an excellent opportunity to meet new people from outside of your circle of friends and interests. When moving to Provo, for example, Sahil was able to meet and befriend the major of the city. Meanwhile, in San Francisco, he did not even know his immediate neighbors.

Why and How did Sahil Lavingia write "Reflecting on my failure to build a billion dollar company"?

It was important for Sahil to understand why he had a goal of building a billion dollar company to begin with, what lead to his failure, and how he's been able to redefine success in order to work on a meaningful company instead.

When Sahil was ready to write, he was not sure what exactly to cover in this essay, so he reached out to friends and asked them for questions. People wanted to know about every little part, from raising money to failing. Starting by answering each individual question, he'd composed a long list of segments, and eventually restructured them into a long-form article.

The title of "Reflecting on my failure to build a billion dollar company" was a deliberate to choice to create something that could be shared without a stance on the subject. Sahil wanted to tell an entertaining story, without necessarily teaching anything.

How did Sahil Lavingia start Gumroad?

Sahil started with the idea for Gumroad while still working at Pinterest back in 2011. He wanted to sell an icon he had designed, and there was no easy way to do it. He was looking for a "lemonade stand version" of a business, it was not available, so he built it over the weekend. Gumroad launched on Hacker News, got to the #1 spot, and people loved it as an idea. The idea was not a great fit for Pinterest, so Sahil self to start it as an independent company. He'd given up some equity in Pinterest which would have been worth millions, but invaluable learning opportunity and a chance to build his own billion dollar company seemed worth more at the time.