The Learning Leader Show With Ryan Hawk

#326: Jason Zook


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Jason Zook is an unconventional entrepreneur. Tired of living a life that felt prescribed to him by society, Jason used his out-of-the-box thinking and ingenuity to create multiple profitable Internet-based businesses.  His most-notable business was IWearYourShirt, a company that generated over $1,000,000 by wearing sponsored t-shirts to promote over 1,600 businesses on social media from 2008-2013 before “influencer” was a mainstream term. If that wasn’t weird enough, from 2012 and 2013, Jason auctioned off his last name to the highest bidders and made nearly $100,000 doing it. Jason’s second book is titled “Own Your Weird.” Jason has been featured by The Today Show, CBS Evening News, USA Today, and The New York Times.


  • The importance of reviewing previous work… And why it should embarrass you.  That is growth.
    • “Don’t compare your starting line to someone else’s finish line.”  We all started somewhere.  It is a progression.
    • It’s important to understand context.
  • Leaders who sustain excellence =
    • They test all of their assumptions on a regular basis
      • They don’t accept things as they are… Always trying something new
    • They are extremely curious
    • Have an experimenters mindset
    • They are validated internally — They don’t seek the validation externally.  They are fulfilled from the inside.
  • How to create a mindset to not worry about hitting a best-seller list?
    • Set a low goal (getting the book published) and a high goal (selling 10K copies).  Understand that there is so much out of your control and celebrate hitting the goals that are within your control (writing and publishing the book).  You can’t control how many people choose to buy it.
    • The emails received from fans/listeners are the fuel that keeps you going.  The feedback from people you’re positively impacting.
  • Properly define success for yourself:
    • You spend a third of your life working.  Make it count.
    • Figure out a way to be see as excellent, out of the box thinker
  • Have a mindset of, “How can I make this better?”
  • Present your plan to your boss/leaders in the company: “Here’s my plan, here is how we will do it…”
    • Be proactive.  Make your boss’s life easier.  Help them succeed.
  • Rejection:  “When someone says no to you, it doesn’t mean you’re a bad person.  It’s not a reflection of who you are as a person.”
    • Understand that “No” means “not yet” most of the time.
  • “Choose Adventure”
    • Not wanting to live the same life that others have lived
    • Example: Moving to a sweet house in Southern California with another couple
  • Challenge assumptions:
    • You don’t have to do it the way it’s always been done
    • Experiment — Test –> Reflect, analyze.  Understand what worked, what didn’t, and why?
  • Working to live, not living to work
    • How do you schedule your days?
      • Start with living
    • Define what really fills you up –> Prioritize that first.  Put it on your calendar first.
  • Every six months, sit down and prioritize what’s important to you.
    • Constraints can be a powerful force.  Parkinson’s Law.
  • Set your “enough goals.”  –>  “Getting to this number will be enough.”
    • “There’s always more.  What about enough?”
    • “We don’t need to grow our business for growth’s sake.”
    • “$33,000/month is our enough goal.” — “It’s clearly defined.  It’s right for us.”
  • The process of writing a book live — Jason learned a lot about himself writing while others were watching.
  • The end of the podcast club:  Email us ( — When was the last time you truly showed up as yourself?

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