#635: Jason Calacanis on Brooklyn Grit, Big Asks, Angel Investing (Uber, Calm, Robinhood, and more), The Magic of Thinking Big, and St*bbing People in the Face but Never in the Back

Brought to you by Eight Sleep’s Pod Cover sleeping solution for dynamic cooling and heating, House of Macadamias delicious and nutritious nuts, and LinkedIn Jobs recruitment platform with 800M+ users. Jason Calacanis (@jason) has invested in more than 300 startups in the past decade (Uber, Calm, Robinhood, and more), was Sequoia Capital's first Scout, and is the author of the book ANGEL. He also hosts two podcasts, This Week in Startups and All-In. Please enjoy! This episode is brought to you by LinkedIn Jobs. Whether you are looking to hire now for a critical role or thinking about needs that you may have in the future, LinkedIn Jobs can help. LinkedIn screens candidates for the hard and soft skills you’re looking for and puts your job in front of candidates looking for job opportunities that match what you have to offer. Using LinkedIn’s active community of more than 800 million professionals worldwide, LinkedIn Jobs can help you find and hire the right person faster. When your business is ready to make that next hire, find the right person with LinkedIn Jobs. And now, you can post a job for free. Just visit LinkedIn.com/Tim. * This episode is also brought to you by House of Macadamias delicious and nutritious nuts! I love macadamia nuts and have been enjoying them often since keto expert Dr. Dominic D’Agostino recommended them on the podcast in 2015. They taste great, and with more healthy, monounsaturated fat than both olive oil and avocados, 27% fewer carbs than almonds, and more than 50% fewer carbs than cashews, they’re the perfect low-carb, keto-friendly, nutty snack. In fact, I just ate a handful of lightly white-chocolate-covered macadamias about an hour ago to keep me going through the afternoon until dinner. And I will say this: ​House of Macadamias produces the best-tasting macadamia nuts I’ve ever eaten… by far. Listeners of The Tim Ferriss Show can use code TIM20 to get 20% off all orders, plus free two-day shipping across the US, UK, and African continent with the purchase of two or more boxes! Visit HouseOfMacadamias.com/Tim to discover some of the most delicious and nutritious nuts on the planet. * This episode is also brought to you by Eight Sleep! Eight Sleep’s Pod Cover is the easiest and fastest way to sleep at the perfect temperature. It pairs dynamic cooling and heating with biometric tracking to offer the most advanced (and user-friendly) solution on the market. Simply add the Pod Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. It also splits your bed in half, so your partner can choose a totally different temperature. For a limited time, Eight Sleep is offering my listeners up to $450 off their Sleep Fit Holiday Bundle, which includes my personal favorite, the Pod 3 Cover. Go to EightSleep.com/Tim to get the exclusive holiday savings. Eight Sleep currently ships within the USA, Canada, the UK, select countries in the EU, and Australia. That’s EightSleep.com/Tim * [05:39] Why is this only the first time Jason’s been on the show? [06:37] Never underestimate the power of checklists. [08:56] How Jason’s young life was steeped in blood and taxes. [11:57] How Jason entered the world of entrepreneurship. [29:32] What happened when Jason got fired from his own company. [34:05] Orchestrating a comeback the very next day. [37:49] The Mercury Club that never was. [41:37] The origin of “Calacanis.” [43:01] Building a blogging empire. [48:36] Finding blog writers. [52:51] Planning events and making memories. [58:39] Friendship, loyalty, and collaboration with close friends. [1:06:00] All-In: When a solo act gets tricked into joining a band. [1:13:39] Memorable times All-In has gone off the rails. [1:21:49] With greatly followed podcasts comes great responsibility. [1:27:38] KeepingAll-In running smoothly with four very different personalities. [1:34:53] Talent-wrangling techniques. [1:39:30] Bill Maher’s moderation style. [1:40:47] Friendly rapport can be contagious. [1:42:26] Can you see your comfort zone from the Overton window? [1:45:44] Transfering skills, building popularity, and co-existing with jet blockers. [1:52:16] What happens when you catch the car? [1:55:15] Psychedelic therapy and a big win in Colorado. [2:01:28] Jason’s billboard and parting thoughts. * For show notes and past guests on The Tim Ferriss Show, please visit tim.blog/podcast. For deals from sponsors of The Tim Ferriss Show, please visit tim.blog/podcast-sponsors Sign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday. For transcripts of episodes, go to tim.blog/transcripts. Discover Tim’s books: tim.blog/books. Follow Tim: Twitter: twitter.com/tferriss  Instagram: instagram.com/timferriss YouTube: youtube.com/timferriss Facebook: facebook.com/timferriss  LinkedIn: linkedin.com/in/timferriss 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, Margaret Atwood, Mark Zuckerberg, Peter Thiel, Dr. Gabor Maté, Anne Lamott, Sarah Silverman, Dr. Andrew Huberman, and many more. 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