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Remotely Interesting

Work Style Profile: Sahil Lavingia, CEO of Gumroad

Published over 2 years ago • 5 min read

Welcome to the latest profile in our Work Styles series! In each profile, we highlight one person's untraditional workday. You'll get an inside look at alternatives to the traditional 9-5, Monday-Friday schedule (and maybe pick up something new to try).

Today, we're featuring Sahil Lavingia, the founder and CEO of Gumroad! In 2011, Sahil left his job as the second employee at Pinterest to start Gumroad, a platform that helps creators sell their products online. He raised more than $8 million in venture capital, intending to become the next tech unicorn, before they crash-landed in 2015.

Since then, he left Silicon Valley, rethought his version of success, and rebuilt Gumroad into a profitable, sustainable business. His article, Reflecting on My Failure to Build a Billion-Dollar Company, became hugely popular and led to publishing his new book, Minimalist Entrepreneur.

In this profile, we get an inside look at his approach to juggling multiple roles (CEO, angel investor, painter, and writer) and how he balances routine vs. flexibility. Let's dive in!

TLDR below 👇 | Read this on the web | Subscribe​

Sahil Lavingia with a first place award in a painting competition in Utah
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What does a day in your work life look like?

My day is both very random and very structured. I start by dropping my wife off at work every day at 8 a.m. Then, a couple of times a week, I go to the gym and go home to shower. So, my workday starts at around 10 a.m., and I work until 4:45 p.m. when I pick up my wife from work.

Outside of this routine, my workday varies. It might be meetings for my venture work, book launch-related tasks, or it might be answering a bunch of stuff for Gumroad. But, the way I like to think about it is, I prefer spending the first 30 minutes to an hour getting to inbox zero on Slack, Discord, Twitter, email, etc.

Once I do that, I work on a to-do list of 2-3 items that are big projects I have to think through. It might be a blog post or an essay. It might be a new product feature at Gumroad. But I like to leave open space to work through these tasks. The goal is to have about 4 hours of free time after lunch for this work.

Sometimes, VC work or meetings will interrupt, but generally, this is what my ideal workday looks like.

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What approach did you take to optimize your work schedule for you?

I've tried a bunch of stuff and found that this routine works well. It's funny because I tout flexibility, but for me, I think flexibility with constraints is pretty important. Otherwise, I'll either work too much, or I'll just work sporadically.

There's also work that isn't necessarily fun, but I need to do it. And I find when I have a really flexible routine, I often don't actually do it. So, I created my own version of the 9-5, except within the 9-5, I'm not just doing work. And I don't structure my time nearly as much.

If I have something like a book I'm writing, I will block out a specific time. Also, generally, I do the stuff I don't like earlier. So I'll block out 2-3 hours of deep work and get it out of the way when my willpower well is high.

Then, I like to leave the post-lunch time for more creative work and keep availability to read. I like to go on Twitter too and just have time to react to the world because, you know, things are happening faster and faster.

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Why did you choose to go against the standard 9-5 schedule?

I think it was initially just burnout. Then, practically, when we started hiring people in multiple time zones (Gumroad has people in 17 different countries), it just didn't make sense anymore. Like, how do you pick a time? It doesn't even work.

And so we had to get rid of meetings. We got rid of the office. When you get rid of the office, it starts to break all the other preconceptions. If you're all over the world and get rid of meetings, you realize no one knows when you work. And really, it shouldn't even matter.

I tell my team I have an SLA where I'll get back to you within 24 hours. Generally, I'm faster, and this works well, but I like that nobody can dictate how I spend my time and that only I can see my calendar. People don't even know when I'm traveling or not. My goal for the things I build is to get it to a place where they have their own momentum to run themselves.

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What's one area you're still looking to improve?

I'm at this Founder Summit conference right now, and one exercise is to categorize all the different parts of your life and rate how you feel you're doing in all of them (social, occupational, spiritual, etc.).

And I really struggle with the social aspect. This probably isn't uncommon, especially during COVID. But it's funny because I built this schedule that allows me to work very little, but because of COVID and moving to a new city, I haven't done a super great job at building deep in-person relationships. And, I think in-person is actually really important for me. So I want to figure that out.

I don't think the answer is to host retreats for Gumroad like other remote companies do. I don't think I need to fulfill the social bucket with Gumroad at all. But that's what I'm thinking about. Come 2022, how do I want to live? Everyone's going to start hanging out again and creating new norms coming out of the pandemic. And I'm interested to see what happens there.

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What is your top tip for someone wanting to transition away from the standard work schedule?

I think that ultimately having a side income is empowering. It opens the door to "Hm, maybe I don't need to rely on this." I call it the monopoly of full-time employment. You can only work in one place at one time. So your employer has a monopoly on your physical body in a sense, and I just don't like that.

I think the way you build leverage is you have a side income, and over time you have more and more financial independence. And this may give you the flexibility to think, "Hm, maybe I can do something else." And that just might be working at another company. Or, maybe a more flexible company, but that is still full-time. Or maybe you switch to part-time.

I'm excited to see the nonbinary of working. Where it's not just you're either unemployed or full-time employed. I think there's a spectrum. I'm excited to see that play out.

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Final thoughts?

I have a book coming out! I think some people will find it valuable, especially chapter 7, Build the House You Want to Live In. It's about culture, hiring, people, and it's about how we work at Gumroad in this async way. There are lots of great tips for anyone curious, and hopefully, the whole book is broadly interesting to people.

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Big thank you to Sahil for giving us an inside look at his workday!

Highly recommend this article from him, No Meetings, No Deadlines, No Full-Time Employees, to get an inside look at how one async-first company runs.

Also, check out his live cohort-based Minimalist Entrepreneur course. I took it myself early this year, and if you're aiming to build a calm, sustainable, bootstrapped business, this is the class for you.

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I'd love to hear from you! What did you find interesting about Sahil's workday? What could you potentially try out yourself?

Feel free to reply to this message or DM me on Twitter @mar15sa.

I truly appreciate you taking the time to read this. Hope you have a lovely day!

Marissa

P.S.

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Remotely Interesting

9-5, Monday-Friday, in-person office work are all relics of the past. This thoughtful newsletter helps you reflect on your current way of life and create actionable steps for a more intentional future. Let's revolutionize how you live by changing how you work.

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