Randy's Open Road

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    Original Roadtrip



“Time is our only precious asset. We pretend that it's money, we pretend that it's material goods…but we could all disappear tomorrow. If this moment isn't a positive, constructive moment for us, it's wasted.”


Entrepreneurship Writing


Fear Money & Financial Security Opportunity Passion Self-Reflection Societal Pressures Support & Encouragement


Being Creative


  • After graduating from Brown University, he simply followed his interests; did everything from teaching economics to promoting rock concerts.
  • He started to feel pressure to "get serious," so he decided to go to law school at Harvard University.
  • It didn't take him long to realize that law was not the path for him, but he continued with it anyway.
  • He worked as a lawyer for Apple for a few years, then decided to branch out to help companies strengthen their brands.
  • Slowly transitioned into taking the risk of starting his own companies; helped launch TiVo and WebTV.
  • Today, he describes himself as a "serial entrepreneur" and has carved out a niche for himself as a "creative free agent."
  • Now his life looks much more like it did when he was just following his interests; he's involved in dozens of projects.
  • Among them, he's written a best-selling book called The Monk and The Riddle, and he teaches entrepreneurship at Stanford University.

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