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, 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! Connect with Vince Vaughn: Follow Vince Vaughn on Twitter: https://twitter.com/vincevaughn How to Fear Less: Vince Vaughn Show Notes: https://tim.blog/2017/05/31/vince-vaughn/ SUBSCRIBE: http://bit.ly/1dSzTkW About Tim Ferriss: Tim Ferriss is one of Fast Company’s “Most Innovative Business People” and an early-stage tech investor/advisor in Uber, Facebook, Twitter, Shopify, Duolingo, Alibaba, and 50+ other companies. He is also the author of five #1 New York Times and Wall Street Journal bestsellers: The 4-Hour Workweek, The 4-Hour Body, The 4-Hour Chef, Tools of Titans and Tribe of Mentors. The Observer and other media have named him “the Oprah of audio” due to the influence of his podcast, The Tim Ferriss Show, which has exceeded 200 million downloads and been selected for “Best of iTunes” three years running. Connect with Tim Ferriss: Visit the Tim Ferriss PODCAST: https://bit.ly/2rYjUBr Visit the Tim Ferriss BLOG: http://bit.ly/17jDHw3 Like Tim Ferriss on FACEBOOK: http://on.fb.me/1avYUxq Follow Tim Ferriss on TWITTER: http://bit.ly/17d94TE Follow Tim Ferriss on INSTAGRAM: http://bit.ly/2IfH37J Follow Tim Ferriss on INSTAGRAM: http://bit.ly/2IfH37J Start 00:00 How Vince and I initially connected. [09:21] Childhood and early lessons. [11:09] Curiosity. [15:19] The traumatic experience that kept me from learning to swim. [16:43] Vince shares his own traumatic experience and what it taught him. [19:37] The role of sports in Vince’s development. [22:08] On developing grit. [27:33] His young life as a telemarketer. [28:25] Smiling and dialing. [33:11] Class president as graduation insurance. [35:46] Lessons from improvisation. [40:13] What separates good improvisation from great improvisation? [42:53] Leaving Chicago for Los Angeles. [44:43] Making ends meet. [49:23] Priceless lessons in hustle. [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? [1:05:27] Facing doubt during the filming of Swingers. [1:12:41] Working with and learning from Steven Spielberg. [1:16:41] Success in spite of an R rating. [1:19:04] The Break-Up movie. [1:22:59] Reassurances and tactical practicalities. [1:26:55] Finding tone in storytelling. [1:28:58] Ben Franklin, 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]