Daily Routines

Sahil Lavingia: Daily Routine

On Daily Routines, we profile successful leaders, entrepreneurs, artists, executives and athletes to explore their routines, schedules, habits and day in the life.

In 2011, Sahil Lavingia was living the tech startup dream. He was the second employee and first designer at the image sharing and social media website, Pinterest, which had just launched the previous year. On the side, he was working on his own project, an online sales platform that he hacked together over a weekend, which would eventually become Gumroad.

Lavingia left Pinterest shortly that year to work full-time on his new venture, raising $1.1 million in seed funding from investors like Accel Partners, Chris Sacca, Max Levchin and Naval Ravikant. A few months later, venture capital firm Kleiner Perkins led a $7 million Series A round for Gumroad, and Lavingia was officially on his way to build the next billion dollar company.

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.

From Bubble to Bubble | Sahil Lavingia

The first couple of years at Gumroad were great. “We had one year of tenfold growth,” Lavingia told Wired. “We were growing like crazy and thought it would be like that every year.” But by 2014, Gumroad’s trajectory had slowed dramatically and investors were demanding to see at least 20 percent growth month on month.

In an interview with Indie Hackers, Lavingia told Courtland Allen that during that time of his life, sleep was the number one priority in his life, followed by Gumroad. Everything else — exercise, relationships, friends — were at the bottom of the list.

“I also had built a team and when you build a team you have this sort of duty but also this sort of financial incentive to work super, super, super hard and stay super, super, super focused because every hour that you put in, you have 20 people that are going to see that and mimic a little bit of that behavior,” he explained to Allen.

Lavingia wrote about the experience of not being able to match investor expectations in his 2018 article, From Bubble to Bubble:

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.


With a sustainable, long-term business on his hands, and no longer part of the hyper-growth, unicorn startup rat race, Lavingia began making major changes to his lifestyle. “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,” he wrote.

He also moved out of San Francisco, the tech capital of the world, to Provo, Utah, a conversative, religious city with a population of just over 100,000 people. The differences between the two cities couldn’t be more stark.

“I gave away all of my furniture and landed in Provo on a Sunday, five suitcases in tow, hoping for some grand epiphany about my path forward. Three Mormons skipped church to pick me up from the airport. One of them had seen my moving announcement on Facebook and sent me a message.”

These days, Lavingia lives in Portland, Oregon, leading the distributed Gumroad team remotely, with a clearer vision of his life moving forward. The company is thriving and more importantly, profitable, pulling in $10 million in annual recurring revenue and growing 100% year on year with a small team of 15, some of them part-time employees.

He’s also opted for a slower, deliberate lifestyle. Instead of working around the clock, sacrificing exercise and neglecting relationships to build a rocketship startup that will eventually cash out for $1 billion, the Gumroad founder opted for a more sustainable lifestyle.

For me, I have a graph that is up and to the right and can’t distinguish between days I worked four hours a day or 16 hours a day. It doesn’t matter. It’s OK to surrender control to the market forces a bit more, give it a fair shot, don’t sacrifice your lifestyle too much. I think most of it will net out.

Day in the Life: Sahil Lavingia | CoFounder Weekly

On a typical day he’s up at 7.30am and starts work at around 9am. During the mornings, between 9am and midday, he’s focused on non-deep work, like calls. After lunch, he’ll get stuck into the deep focus work between 1-7pm.

“I sleep for at least 7 hours every day. I try for at least 7 and a half, sometimes more. Sleep is the most important thing for me – always has been,” Lavingia said in an interview with The Proof, describing his evening routine. “I try to put away my phone and pull out my Kindle. Most books put me to sleep after less than thirty minutes.”

Lavingia’s work hours are also dramatically less than most other startup founders — there are some weeks where he’ll only work 15-20 hours; something he’s also implemented company-wide.

“There is a new focus on remote work, but I think it’s just a stepping stone towards something much more interesting: flexible work,” he tweeted in 2019. “For example, an engineer could work at Facebook 60 hours a week and make $250K a year. Or, work at Gumroad 20 hours a week and make $150K a year. How many would prefer to make $100K less a year for an extra 40 hours per week to spend elsewhere?”

Before you go…

Check out more daily routines from Barack Obama, Joe Rogan, Jeff Bezos, Michelle Obama, Sheryl Sandberg, Richard Branson, Warren Buffet and plenty others.

About Author

Hey there! I'm Hao, the Editor-in-Chief at Balance the Grind. We’re on a mission to showcase healthy work-life balance through interesting stories from people all over the world, in different careers and lifestyles.