About Derek
Derek Sivers has worn many hats, musician, entrepreneur, author, and philosopher, but his work maintains a single throughline: a relentless pursuit of living deliberately. He found entrepreneurial success by founding CD Baby, an indie music platform that revolutionized digital distribution before he sold it for over $20 million and donated most of the proceeds. Since then, he’s become a bestselling author of books like Anything You Want, Hell Yeah or No, and Useful Not True, each filled with punchy, poetic wisdom earned from experience. In this episode, we explore how to treat your life like a design problem, why marketing is part of the art, and how vulnerability and weirdness aren’t liabilities—they’re the keys to resonance. Whether you’re building a company, making games, or just trying to figure out how to live a more meaningful life, this conversation will challenge your assumptions and invite you to take that first small but deliberate step.
Ah-ha! Justin’s Takeaways
Art Doesn’t End at the Edge of the Canvas: Derek shares one of the most powerful lessons of his career: the art isn’t just the song, the book, or the game: it’s how you present it to the world. When helping a friend promote a concept album, he didn’t just send a CD to radio stations; he hand-crafted a bizarre, dirt-rubbed package from a fake conspiracy theorist living in the bushes behind the studio. The result? 540 out of 600 stations played the album. Derek urges creators to treat marketing as an extension of the creative process and not an afterthought.
Make Your Brain a More Fun Place to Be: One of my favorite takeaways from this conversation with Derek is how he treats thinking like play. When he hears a belief like: “you have to go to college to succeed,” he doesn’t accept it at face value. He flips it. Asking: what if the opposite were true? That kind of mental inversion is something I do regularly through my “assumption-challenge” exercises, and it’s one of the most powerful creative tools I know. Derek also offered a framing I loved: instead of asking “Is this idea true?”, ask “What action does this idea create?” If a belief drains your energy or keeps you stuck, toss it. If it moves you toward growth, connection, or creative output, follow it. That mindset doesn’t just help with ideas; it makes your brain a more fun, surprising, and productive place to be.
What 5-Minute Action Could Shortcut You to What You Really Want?
Most people take the long way around. They imagine multi-year plans to finally do the thing they care about. Derek challenges that mindset with a simple question: what’s the five-minute action that could start you down the shortcut path? For him, it was booking a flight to China the next morning with his son, within 24 hours of the idea. He didn’t map the whole trip, instead he just took the first step. The lesson: your next big transformation might only be five minutes away.
Show Notes
“I realized early on by looking at the careers of other musicians that the way to succeed is to stand out, to be different from everyone else. You've got to find your unique voice in the cacophony.” (00:06:14)
Derek shares how his obsession with music from age 14 taught him the power of intense focus and differentiation. He compares the path of becoming a successful artist to an Olympic athlete: only the most dedicated make it. His insight—that success requires you to be unmistakably yourself—applies to any creative field, from songwriting to game design.
“The best thing you can do is whatever nobody else is doing. And the way to find that is to notice what about yourself is weird.” (00:17:05)
When asked how creators can stand out, Derek encourages embracing your weirdness. He and Justin explore how quirks, vulnerability, and personal truth deepen audience connection. Whether it’s a confessional paragraph on a website or a bold design choice, the things that make you different are often the most memorable—and the most powerful.
“Everything’s a fun ‘let’s see what happens’ kind of experiment. You're not searching for the right answer, you're just playing.” (00:29:03)
Derek describes iteration not as failure, but as playful experimentation. He urges creators to treat business and creative risks the way game designers treat prototypes: as sandboxes. This mindset removes ego from the equation and invites curiosity-driven exploration—key to discovering innovative ideas and enjoying the process along the way.
“Ultimately, everything we're talking about is being considerate to the person on the receiving end... You're making people's lives a little more interesting by giving them something that's not what everybody else is doing.” (00:41:01)
In a powerful reframe of marketing, Derek argues that bold, unusual choices are actually acts of generosity. He tells the story of how he helped an artist mail dirt-smeared conspiracy-themed CD promos to radio stations—and why 540 of them played it. The lesson: creativity doesn’t stop at the product. It extends to how you share it with the world.
As a great follow up, check out this episode with writer Steven Pressfield:
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