Cover art for podcast Below the Line with James Beshara

Below the Line with James Beshara

155 EpisodesProduced by James BesharaWebsite

Host James Beshara is an angel investor, advisor, founder, & general startup-helper in Los Angeles, CA. He has started three companies, sold one (Tilt; acq by Airbnb), and invested in multiple billion-dollar startups in his career. Now he's talking openly and honestly with others about what's going … read more


#53 — DeepDive — “How to Monetize Creativity and Solo-preneurship” — Sahil Lavingia

"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

Educational emoji reaction


Interesting emoji reaction


Funny emoji reaction


Agree emoji reaction


Love emoji reaction


Wow emoji reaction


Are you the creator of this podcast?

Verify your account

and pick the featured episodes for your show.

Listen to Below the Line with James Beshara


A free podcast app for iPhone and Android

  • User-created playlists and collections
  • Download episodes while on WiFi to listen without using mobile data
  • Stream podcast episodes without waiting for a download
  • Queue episodes to create a personal continuous playlist
RadioPublic on iOS and Android
Or by RSS
RSS feed

Connect with listeners

Podcasters use the RadioPublic listener relationship platform to build lasting connections with fans

Yes, let's begin connecting
Browser window

Find new listeners

  • A dedicated website for your podcast
  • Web embed players designed to convert visitors to listeners in the RadioPublic apps for iPhone and Android
Clicking mouse cursor

Understand your audience

  • Capture listener activity with affinity scores
  • Measure your promotional campaigns and integrate with Google and Facebook analytics
Graph of increasing value

Engage your fanbase

  • Deliver timely Calls To Action, including email acquistion for your mailing list
  • Share exactly the right moment in an episode via text, email, and social media
Icon of cellphone with money

Make money

  • Tip and transfer funds directly to podcastsers
  • Earn money for qualified plays in the RadioPublic apps with Paid Listens