How to Fear Less: Vince Vaughn

“Fear is more crippling than the actual consequences.”
– Vince Vaughn

Vince Vaughn (@WildWest) is one of the most prolific actors, writers, and producers in the world. He’s acted in more than thirty major motion pictures that have gone on to gross more than 1.7 billion at the box office. He is largely credited for redefining the R-rated comedy with his performance in the 2005 hit Wedding Crashers, which set the record for highest grossing R-rated comedy at the time. He is — and will continue to be, I expect — one of the most sought-after leading men in Hollywood.

As a listener to this podcast, Vince reached out with his production company Wild West to see if we might do a TV show together. The result is Fear{less} with Tim Ferriss — “less” is in parentheses because the objective is to teach you to fear less, not to be fearless. More details about the show can be found at tim.blog/fearless. Or, if you want to watch the entire first episode with performance artist David Blaine (@davidblaine), you can see it here or visit att.net/fearless.

I had the chance to catch up with Vince at Vulture Festival in New York City. In this conversation, we get into stories of his early beginnings, how to negotiate, his cold-calling career, and important decisions he’s made as a producer, an artist, and a businessperson. I had a blast doing this, and I hope you enjoy it as much as I did!

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Want to hear another podcast with a comedian, actor, and director? — Listen to my conversation with Jon Favreau. In his episode, we discuss his writing process, daily routines, how to create films that redefine categories, and much more (stream below or right-click here to download):


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QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…

Selected Links from the Episode

Show Notes

  • How Vince and I initially connected. [09:21]
  • Vince talks about childhood and early lessons he learned from his parents. [11:09]
  • Vince asks a lot of questions. Where did his curiosity originate? [15:19]
  • I share the traumatic experience that kept me from learning to swim until my thirties. [16:43]
  • Vince shares a traumatic experience from his high school days and what it taught him. [19:37]
  • The role of sports — particularly wrestling — in Vince’s development. [22:08]
  • On the process of developing grit. [27:33]
  • Vince talks about his young life as a telemarketer. [28:25]
  • My first job out of college was smiling and dialing. [33:11]
  • Did an academically disinclined Vince become class president in high school as a form of graduation insurance? [35:46]
  • Vince talks about sharpening his acting chops with improvisational legend Del Close. [40:13]
  • What separates good improvisation from great improvisation? [42:53]
  • Why did Vince decide to leave Chicago for Los Angeles? [44:43]
  • How did Vince make ends meet early in his acting career? [49:23]
  • Priceless lessons in hustle from an underprivileged friend. [50:03]
  • Vince Vaughn’s fight club. [54:07]
  • Advice for beginning actors coping with rejection. [56:55]
  • What is screen testing? [59:15]
  • Microfailures as an inoculation against rejection. [1:01:49]
  • Maintaining motivation by “always going back to white belt.” [1:02:17]
  • Why this podcast is an anomaly. [1:03:42]
  • How did Swingers come to be? Was it strictly scripted or heavily improvised? [1:05:27]
  • Was there ever any doubt during the filming of Swingers that the project would be completed? [1:12:41]
  • On working with and learning from Steven Spielberg. [1:16:41]
  • Why does Vince think Wedding Crashers was such a success in spite of its R rating? [1:19:04]
  • What made The Break-Up different from other movies Vince had done up to that point? [1:22:59]
  • Reassurances and tactical practicalities learned by looking over Vince’s career. [1:26:55]
  • Finding tone in storytelling. [1:28:58]
  • What Ben Franklin understood about expanding comfort zones and the art of the hustle. [1:30:42]
  • “Fear is more crippling than the actual consequences.” [1:35:29]
  • What would Vince’s billboard say? [1:37:15]
  • Parting thoughts. [1:38:39]

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