#39. A Cartoonist on Creativity, Money, and Letting the Work Lead (with Todd Webb of The Poet)

What does it look like to build a creative life over decades and make it deeply satisfying and sustainable?

In this episode, we sit down with cartoonist, illustrator, musician, and writer Todd Webb, creator of the daily comic strip The Poet. Todd shares how a project that started as a short book quietly turned into a six-year daily practice, how Substack, book collections, and pop culture art prints support his work, and why he’s more interested in enjoying the act of creation than chasing a single “big break.”

We discuss:

1. You don’t need one big income stream. Small creative trickles add up.
2. Todd’s work is supported by a mix of Substack subscriptions, book sales, art prints, conventions, and commissions. None of them are floods, but together they create enough space to keep making what he loves.
3. Make the thing you want to exist, not the thing you think will sell.
4. The Poet wasn’t designed to be a daily strip or a long-running project. It became one because Todd followed the work instead of forcing an outcome.
5. Giving your work away can be a powerful long-term strategy.
6. From mailing mini-comics to artists he admired to offering a mostly free Substack, Todd shows how generosity builds real connection over time.
7. Creative success doesn’t have to mean constant escalation.
8. Not every project needs to become a TV show, a franchise, or a brand empire. Sometimes success is simply having the time and energy to keep creating.
9. You get more than one chance every single day.
10. Missed opportunities, rejected pitches, and projects that don’t pan out aren’t dead ends. They’re material. Ideas can be reused, reshaped, and reborn when the timing is right.

About Todd

Todd Webb has been drawing the daily comic strip The Poet for the past six years. Prior to that he did a lot of other stuff like comic books and graphic novels, music, illustration, screenwriting, and animation. Find info on all of it (and subscribe to The Poet) by visiting TODDBOT.COM

Follow Todd on Instagram

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The information provided in this podcast is for informational and entertainment purposes only and should not be considered financial, investment, tax, or legal advice. The opinions expressed by the hosts and guests are solely their own and do not reflect the views of any companies or organizations they may be affiliated with.

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