The Undefeated Underdogs

👉🏼 About the Guest:

Derek Sivers is an author of philosophy and entrepreneurship, known for his surprising quotable insights and pithy succinct writing style. Formerly a musician, programmer, TED speaker, and circus clown, he sold his first company, CD Baby, for $22 million and gave all the money to charity. Sivers' books (How to Live, Hell Yeah or No, Your Music and People, Anything You Want, Useful Not True) and newest projects are at his website: sive.rs

👉🏼 About the Host:

Sharath is a founder, creator, and community builder. He is also a serial maker who built and shipped 15+ projects using no-code tools. His SaaS product Shoutout generated $30k ARR, which was sold to a UK-based product studio. Prev, Sharath worked for world-changing startups like Product Hunt and On Deck, where he helped build and nurture communities. He also grew his audience on Twitter from 200 to 22,000 using give-first principles and creating high-value content. Currently, he is building a SaaS product called GuestLab, and runs another podcast series called YC Founder Stories alongside hosting this one, as well as running Founder Gigs, a resource to discover flexible gigs while building your dream business.

👉🏼 Sponsor Corner:

Shoutout to Acquire.com for sponsoring The Undefeated Underdogs podcast! They’re the best online marketplace to buy/sell startups and I know many founders who have sold their businesses there. If you're looking to wind down your business and cash in some of your founder chips, check them out - https://try.acquire.com/sharath/

👉🏼 Description:

Listen in as Sharath and Derek discuss taking scary leaps, why beliefs are better than truths, how to pick your next move, and more!

👉🏼 Timestamps:

• 00:00: Episode Highlight
• 01:00: Shoutout to Acquire.com
• 03:27: Introduction to Derek Sivers - founder, musician, programmer, TED speaker, and circus clown
• 04:30 Why Derek wears a daily uniform (and no, it's not to imitate Steve Jobs)
• 15:51: Why is Derek obsessed with change?
• 19:06: How to pick your next move
• 22:43: How to move on from what you love
• 32:15: What Americans can learn from traveling the world
• 39:30: Derek's bucket list of countries
• 44:04: Derek on parenting
• 53:10: Turning a hook into a book
• 1:01:13: Useful beliefs vs the truth
• 1:13:10: Derek's beliefs that take him to action
• 1:18:10: The philosophies that drive Derek to create
• 1:20:43: Derek's first scary moment
• 1:27:00: Deleted scenes from "Useful Not True"
• 1:34:33: What Derek is struggling with right now
• 1:38:09: Derek's practices to improve consistency
• 1:43:40: Rapid Fire 5: From favorite city to best recent read
• 1:45:32: Outro and closing thoughts

👉🏼 Resources:

• Link to Acquire.com: https://try.acquire.com/sharath/
• "Playful Parenting": https://www.goodreads.com/book/show/160909.Playful_Parenting
• "The Eternal Pursuit of Unhappiness": https://www.goodreads.com/book/show/22925205-the-eternal-pursuit-of-unhappyness
• "Cows, Pigs, Wars, and Bitches": https://www.goodreads.com/book/show/60653.Cows_Pigs_Wars_and_Witches
• "City of Gold": https://www.goodreads.com/book/show/1588793.City_of_Gold

👉🏼 Where to find Derek:

• Website: https://sive.rs
• Derek's book, "Useful Not True": https://sive.rs/u
• Twitter: https://twitter.com/sivers
• Youtube: https://www.youtube.com/user/dereksivers
• Linkedin: https://www.linkedin.com/in/andrewrea1996/
• Contact Derek: https://sive.rs/contact

👉🏼 Where to find Sharath:

• Twitter: https://twitter.com/5harath
• YouTube: https://www.youtube.com/@5harath
• Website: https://5harath.com/
• Newsletter: https://5harath.substack.com/
• Founder Gigs: https://foundergigs.com/