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Jason Sadler (known as Jason HeadsetsDotCom for 2013) has one of the earliest stories of using social media to make money in unusual ways.  What started out convincing brands to advertise on his t-shirt grew into a full-blown company. Here are some of the highlights from our conversation:

  • The Power of Breaking Rules and Unleashing Your Creativity 
  • Why You Shouldn't Worry About Whether or Not Your Ideas Work
  • Reconnecting to the Creativity that Lies Within You 
  • The Disadvantages of a Business Plan and Not Straying From It
  • How to Leverage Small Victories for Making Progress
  • The 51 Apps that Came Before the Success of Angry Birds
  • A Higher Education Epidemic that Causes People to Have No Skills
  • Why College Potentially Puts You into a Position to Fail
  • The Importance of Figuring Out Things You Don't Want to Do
  • Embracing The Side Hustle and Trying New Things
  • The Evolution of IWearYourShirt into a Sharing Economy Platform
  • Simple Tactics to Get the Word Out About Your New Endeavor
  • Overcoming Resistance You Face When Selling New Ideas
  • Crafting a Media Plan for Your Business or Product
  • Why Jason Became Disillusioned with His Success
  • Recognizing the Red Flags that Signal Time for a Change
  • Why You Shouldn't Get Attached to Business Outcomes
  • How to Avoid Becoming a Victim of Your Own Success

Resources Mentioned Include: 

Jason Sadler is founder of IWearYourShirt and a lover of unique marketing. He's also a car enthusiast, frequent doodler, Scrabble lover, public speaker, and member of the Young Entrepreneur Council. You can follow him on twitter @iwearyourshirt and @thejasonsadler. If you liked this article, would you share it with your friends? Just click here to post it to Twitter. 


Originally aired about 3 years ago.


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