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. I got 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! Show notes and links for this episode can be found at www.fourhourworkweek.com/podcast. This podcast is brought to you by 99Designs, the world's largest marketplace of graphic designers. I have used them for years to create some amazing designs. When your business needs a logo, website design, business card, or anything you can imagine, check out 99Designs. I used them to rapid prototype the cover for The Tao of Seneca, and I've also had them help with display advertising and illustrations. If you want a more personalized approach, I recommend their 1-on-1 service. You get original designs from designers around the world. The best part? You provide your feedback, and then you end up with a product that you're happy with or your money back. Click this link and get a free $99 upgrade. Give it a test run... This podcast is also brought to you by Trunk Club. I hate shopping with a passion. And honestly, I'm not good at it, which means I end up looking like I'm colorblind or homeless. Enter Trunk Club, which provides you with your own personal stylist and makes it easier than ever to shop for clothes that look great on your body. Just go to trunkclub.com/tim and answer a few questions, and then you'll be sent a trunk full of awesome clothes. They base this on your sizes, preferences, etc. The trunk is then delivered free of charge both ways, so you only pay for clothes that you keep. If you keep none, it costs you nothing. To get started, check it out at trunkclub.com/tim.

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Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more.

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#243: How to Fear Less -- Vince Vaughn

The Tim Ferriss Show