The Uncomfortable Conversations, Radical Candor and Critical Confrontations

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Not all uncomfortable conversations are difficult, aside from the fact that most people avoid and would prefer not to feel discomfort. Radical candor is really clear an you need to build a solid relationship with people which is absolutely true. Conversations go better when you have asolid relationship with someone, and they know that you 're on their side because you want to help them.

Alisa Cohn on Prenups for Startup Founders, How to Reinvent Your Career, the Importance of "Pre-Mortems," and the Three Selves | Brought to you by Kettle & Fire high quality, tasty, and conveniently packaged bone broths; Wealthfront automated investing; and Allform premium, modular furniture. More on all three below.

Alisa Cohn (@AlisaCohn) is one of the most prominent startup coaches in the world. She has advised founders and executives at Venmo, Etsy, DraftKings, Wirecutter, Mack Weldon, InVision, Tory Burch, and others. She has also coached CEOs and C-suite executives at enterprises such as Dell, Hitachi, Sony, Google, Microsoft, Bloomberg, The New York Times Company, and Calvin Klein.

She is the author of From Start-Up to Grown-Up, a guidebook for entrepreneurs on the leadership journey from founder to CEO, and host of the From Start-Up to Grown-Up Podcast. Her articles have appeared in Harvard Business Review, Forbes, and Inc. magazines, and she has been featured as an expert on Bloomberg TV, the BBC World News, and in The New York Times. A recovering CPA and one-time startup CFO and strategy consultant, she is now an angel investor and advisory board member. Outside of work, she is a (very) amateur rap artist and an investor in Broadway shows, two of which have won Tony Awards.

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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.