From Bubble to Bubble

Sahil Lavingia
9 min readFeb 7, 2018

This story is now available directly on my website: — I’d prefer you read it there!

A year ago, I lived in San Francisco. I spent over $2,000 a month for one bedroom in a two-bedroom apartment in the Mission District. Outside of working on my startup, I devoured books on my Kindle and brooded with my fellow liberals about Trump and the GOP on Twitter. Most everyone I knew was agnostic.

I had my whole life planned out. Decades of startups, at least one of which would hit it big. A retirement full of vapid, but pithy tweets.

Today, I live in Provo, the most conservative (and religious) city over 100,000 people in America. I live in a one-bedroom apartment that costs $800 a month. I no longer tweet as much, and especially not about politics. A majority of my friends, including my girlfriend, are religious, and most of them are conservative. I go to church every Sunday.

What changed?

A quarter-life crisis

In 2014, I was the founder of a 20-person VC-backed startup called Gumroad that helps creators of all stripes sell their work.

In 2015, I had to lay off over half of the company. Our growth wasn’t reaching the 20%-a-month we needed to raise the funding we required to grow at the same, aggressive pace. I decided to pivot the company towards a sustainable business model. That meant nixing the office and having to let many of my friends go. It was the right decision — we attained profitability, and while we can’t ship as quickly, Gumroad will be around for the long haul.

It also meant that Gumroad no longer looked like my magnum opus. While it remains a great business today, I felt like I was stagnating.

So, I dabbled. In my spare time, I started writing a fantasy novel in the vein of The Giver. I began learning how to draw. I invested in my hobbies, though I did not have a long-term project to replace Gumroad. I was used to solving problems, but now I didn’t know what problem to solve. Like many others, I was consumed and horrified by the presidential election — was there a problem here that I could work on?

I didn’t really know what I wanted to do, but I felt like San Francisco wasn’t going to tell me. My days were filled with friends that thought like me, and meetings in which we patted each other on the back. We knew the solutions to the world’s problems — the rest of the world…

Sahil Lavingia