In 1988, college student Jonathan Bush climbed on top of a pile of wooden slats in the middle of an unfinished housing development and looked out over a gathering of political volunteers, “Okay,” he announced. “Here’s how it’s gonna go. My name is Jonathan Bush, and we in the next four days are gonna win this election.”

“This election” was for his uncle, George H.W. Bush, in his first campaign for president. Jonathan didn’t think much of the speech at the time; he’d given thousands of such stump speeches to volunteers before, and would go on to give many more before the campaign was over. However, months later, after the White House had been won and his uncle sworn in as President, Jonathan had more than one person tell him that his speech was a seminal event for the campaign.

“I mean I did everything wrong. But I had been allowed a little bit like Gladwell to have my ten thousand hours of speech giving, and then it mattered all of a sudden and I was on top of this pile of sticks that I had created…I had gone through a lot and it was all visible on my face. And, uh, it worked.”

While it may not have been the Saint Crispin’s Day speech from Henry V, Jonathan nevertheless learned that he has the ability to galvanize people about things that he really cares about.

One thing he cares passionately about is health—early in his life Jonathan aspired to be a doctor, but after working as an EMT and in the Army Medical Corps he realized that he needed something more varied that would still give him the satisfaction of having done good in the world. In 1997, he co-founded Athena Women’s Health, a women’s health and birthing clinic in San Diego, which eventually led to athenahealth, a healthcare technology platform for coordinating patient care. Named on Fortune’s list of “34 Leaders Who Are Changing Healthcare,” Jonathan is disrupting the industry by playing in areas that other’s aren’t playing, and is outspoken in his belief that our health care system needs to be repaired.

“I’m at my best when I am making an unbelievably compelling case for what’s possible around the corner…I’m aspirational. I mean, what I can do is say, “Look…we’re gonna catch the car. You and me, we dogs, we’re gonna catch that car.”

Takeaways from this episode:

  • Early in his life, Jonathan equated worthiness to receive love with “good works.” To him, his uncle (President of the United States George H.W. Bush) was at the top of this worthiness scale, and it was Jonathan’s duty to find a way to serve and contribute as much as possible to the worldwide community. While he now recognizes that may not have been the message his family was trying to send, it nevertheless impacted his worldview.
  • Being “in the fight” and gaining knowledge is almost more important than the achievement at the end. “No matter how hard you are in your thinking, if you believe that the fight you’re in is the gateway to a much bigger fight, that you’re always at the tip of a much bigger…mountain range or the entrance of a bigger mountain range…that’s to me what gives me great joy, and satisfaction is that we keep finding whole new frontiers.”
  • “An entrepreneur is someone who doesn’t want to compete with everybody else.”

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