Jesse Winton: Making Movies, Millennials, and Learning to Mind the Gap (AoL 066)

People will come up with a million excuses not to do something. But it takes one good one – one why – to actually go and accomplish a big lofty goal.

Case in point – Jesse Winton, had never made a movie before. But yet, his first one, made it national.

Sure, he could have psyched himself out by saying that his goal was unattainable, but instead, he chose to kick those thoughts to the side and go after this goal.

In this session, learn from Jesse how he was able to get his idea off the ground, what his perception of Millennials are when it comes to how they’re viewed, and how he handles discomfort during the middle of a project – aka The Gap.



  • How did his homeschooling background contribute to where he’s at now? 6:01
  • Were his parents supportive of his aspirations? 8:07
  • What kind of specific knowledge or training did he have to get his ‘Targeted’ off the ground? 11:16
  • Jesse’s perception of Millennials vs what others view them as. 15:34
  • How do we convert more Millennials to become creatives? 21:03
  • What sparked Jesse to create the film? 25:07
  • Why Jesse identifies with Libertarians. 28:27
  • Why did Jesse create Wintons Motion Pictures? 33:00
  • What goes into preparing for pitch meetings? 35:34
  • How Jesse went national with his documentary. 31:33
  • Was there any fear in reaching out to influencers? 42:29
  • How did Jesse and his dad find interviewees for the documentary? 46:26
  • How does he handle discomfort that comes up during the middle of a project? 51:57
  • What’s coming next for Jesse? 58:50
  • Who are three influencers that have helped him get to where he is today? 1:01:17
  • Top Favorite Books that he recommends 1:02:22
  • Smallest decision he’s made that has had the largest impact on his life 1:03:18
  • What is one thing that all high school students must know… even if it involves Dane Maxwell. 1:04:08
  • What’s it mean to live a life of abundance? 1:06:14
  • What can people do to live an inspired life? 1:07:15
  • … and MUCH more!

Right click here and save-as to download this episode to your computer.



Targeted DVD Promo:

Interview with Glenn Beck:

Interview with Perry Atkinson via theDoveTV:

The Gap by Ira Glass:

Jesse’s mad skills on the Fiddle:

making movies

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