The Learning Leader Show With Ryan Hawk

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Full show notes can be found at

#364: Derek Sivers: Derek Sivers is a writer, musician, programmer, and entrepreneur best known for being the founder and former president of CD Baby, an online CD store for independent musicians. A professional musician since 1987, Sivers started CD Baby by accident in 1997 when he was selling his own CD on his website, and friends asked if he could sell theirs, too. CD Baby went on to become the largest seller of independent music on the web, with over $100M in sales for over 150,000 musician clients. 


  • The similarities between becoming a Dad and starting a business:
    • The transition from being “me” focused to becoming focused on others first. “That happened when I started a business… Long before I became a dad.”
    • “As a dad, I learned to be fully present with him. To shut everything else down and focus on him.”
  • “Adults are always looking for amazing superlatives. Kids are happy with tiny details.”
    • “Stop wasting hours… Learn to have a blast where you are.”
  • Making big decisions:
    • There is a difference between theory and in practice
      • “Don’t consider anything decided until you’ve tried it.”
  • Why you should keep your goals to yourself:
    • An identity goal makes you a different person. If you announce it to others and they give you social satisfaction, that feedback you receive gives you internal satisfaction. That could lead to you already feeling satisfaction and thus less likely to achieve the goal… Receiving the satisfaction from others before you’ve done it is not helpful.
    • (NOTE – There is additional information to read about this nuanced topic. THIS is helpful.)
  • Sustaining excellence:
    • They hold themselves to high standards. They set high stakes.
    • They have amazing self-control
    • “Excellence is setting high standards and living up to them.”
  • Excellent leadership is being selfless… Doing what’s in the best long-term interest of the people you’re leading.
  • Selling CDBaby for $22m and giving the proceeds away to charity.
  • The power of writing:
    • “I journal my ass off.”
    • Documenting your daily thoughts is a very useful exercise — It’s fascinating to look back on how you felt at that specific time.
  • Create “Per Topic” Journals
    • Journals that focus on a specific topic (Singapore, Interviews, Language Learning)
  • Values = Learning… Remaining flexible and creative. Answering the questions, “What did I really want from that?”
    • Derek’s values evolve and change over time
  • Being a monomaniac – Obsessed with one thing at a time
    • Currently: Writing a book called How To Live
  • The stress of replying to 7,000 emails vs making a genuine connection with each person…
    • Being a longterm thinker
  • Here is WHY joining a Learning Leader Circle is a good idea…


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