How to Monetize Creativity and Solo-preneurship — Sahil Lavingia


Sahil Lavingia (founder of Gumroad) talks to James Beshara about turning creativity into a monetized (side)business.

This is a long one but well worth the investment if you’re thinking of turning something you love doing into a source of income.

Lesson learned

  • You don’t know what’s going to work or how long it's going to take to see some success.
  • People know where they want to be but don't know where to start. They usually don't know who it's for.
  • Intention vs result - if intention is to get noticed then the result is mediocre work. If the intention is to create awesome work then the result is to get noticed.
  • A lot of people don’t want to do the work. They just want the outcome. Stop thinking about the money and you’ll make the money.
  • Find the person you want to be and reverse engineer how they got there. Don't focus on what they're creating now - go back to what they did when they started out.
  • Learn in public. It helps build an audience.
  • The early content you create appreciates over time. You can repackage and sell to new customers in the future.
  • When you have a skill and have built an audience, people will start to reach out and want to pay you for your work. When you get skill and audience right, monetization comes easy(ish).

"The most exciting new podcast in the startup world.” - Eric Ries, Founder, and NYTimes bestselling author

Mentioned in the podcast:

Today we've got another deep-dive episode and this one is on monetizing your creativity.

It's with Sahil Lavingia, who is the founder and CEO of Gumroad, who's been on the podcast before. A great Below the Line episode with him going into detail in reflecting on his entrepreneurial path. Today goes a little bit more into detail on one specific thing, and that's monetizing your creativity.

Not only has Sahil monetized his own creativity, but he is also the founder of a company, a writer, and a painter. But his company actually powers the monetization of a countless number of creatives around the world. Whether they are creating art, making music, writing books, or wanting to pursue a side hustle.

Sahil tweeted about this recently, and that tweet thread is why I'm having him back on the show. He sent out a single tweet that went pretty viral that said: “I believe virtually everyone can make a living doing what they love. I discover new creators doing it in new ways almost every day. Do you want to create full-time but don't see a path towards doing it? Reply with what it is and let's see if I can help you outline a plan!”.

A lot of people replied and a lot of patterns emerge from that single tweet that I'm excited to dive into with Sahil today. We covered the concept of exercising versus training, prolific versus perfect and setting realistic expectations and timelines. We also talked about being really public, really early. When he started to paint he actually created an Instagram @shlpaints before he even started to paint as a way to give people an insight into his path as a painter, and also as an accountability tool. We talked about why, when, and how to build an audience — and also about the time and dedication required to build the necessary skills and the audience that could provide potential financial freedom while pursuing one's craft.

If it's something that you set realistic expectations, and specific goals around then, in Sahil’s words, it's as easy as going to the gym three times a week for two years... He's never heard of that “not working for somebody,” and he thinks the same applies to anyone that wants to pursue a creative endeavor.

Speaking of creativity... Do you want more creativity, more flow, more energy, and less stress? Do you want to tap into what nature gives us beyond just coffee? For all of these things go to to get the two-ounce shot that contains 12 magical ingredients that are scientifically designed to improve your productivity. Along with CEOs, doctors, musicians, even Navy Seals, I take it every day (and have been for about six years) — and it is the single most important part of my morning ritual to do more and stress less.

To learn more, go to and enter the promo code “BTL” for Below The Line to get 15% off and try it for yourself.

You can email James questions directly at or follow us on Twitter @ — “Below the Line with James Beshara" is brought to you by Straight Up Podcasts LLC