Mike Birbiglia, The Sleepwalking Comedy Giant (#176)

“Art is socialism, but life is capitalism.” – Mike Birbiglia Mike Birbiglia (@birbigs) is one of the best-known and busiest working comedians in the world, both behind and in front of the camera. His standup blends elements of theater, film, storytelling, and comedy. Mike has been deliberate in studying many crafts and tying them together, …

The Random Show – New Favorite Books, Memory Training, and Bets On VR (#171)

This is not going to be a long-form interview where I dissect and deconstruct a world-class performer…at least not in the usual fashion. Instead, this is a special edition of The Random Show. I am joined by Kevin Rose (@KevinRose), serial entrepreneur, world-class investor, and all around wild and crazy guy. We discuss a wide …

How to Overcome Fear – Lessons from Firefighter and Luger, Caroline Paul (#151)

Caroline Paul (@carowriter) is a blast and can also probably kick my ass… seriously. Caroline is the author of four published books. Her latest is the New York Times best seller The Gutsy Girl: Escapades for Your Life of Epic Adventure. Once a young scaredy-cat, Caroline decided that fear got in the way of the …

How to Say No When It Matters Most (or “Why I’m Taking a Long ‘Startup Vacation'”)

Saying yes to too much “cool” will bury you alive and render you a B-player, even if you have A-player skills. To develop your edge initially, you learn to set priorities; to maintain your edge, you need to defend against the priorities of others.

The Tattooed Heretic of Wine and Whiskey, Richard Betts (#110)

“Wine is a grocery, not a luxury.” — Richard Betts Richard Betts (@yobetts) served as the wine director at The Little Nell in Aspen from 2000 to 2008. Much more interesting to me, Richard passed the Court of Master Sommeliers’ Masters Exam on his first attempt, becoming the ninth person in history ever to do so. …

The Oracle of Silicon Valley, Reid Hoffman (Plus: Michael McCullough) (#101)

Reid Hoffman is often referred to as “The Oracle of Silicon Valley” by tech insiders, who look at his company-building and investing track record (Facebook, Airbnb, Flickr, etc.) with awe. Reid is Co-Founder and Executive Chairman of LinkedIn, which has more than 300 million users. He was previously Executive Vice President at PayPal, which was purchased …

Matt Mullenweg on Polyphasic Sleep, Tequila, and Building Billion-Dollar Companies (#61)

Matt Mullenweg has been named one of PC World’s Top 50 People on the Web, Inc.com’s 30 under 30, and Business Week’s 25 Most Influential People on the Web. In this episode, I attempt to get him drunk on tequila and make him curse. Matt is most associated with a tool that powers more than …

How to Create a Blockbuster Podcast (#58 & #59)

“What makes ‘good tape’? That is the question that has consumed my life for the past 20 years, and I have an answer for you…” – Alex Blumberg How do you create a blockbuster podcast? This episode explores the tips, tricks, and best practices of a master. My guest is Alex Blumberg, who cut his teeth …

Maria Popova on Writing, Workflow, and Workarounds (#39)

“Why put in the effort to explain why it isn’t a fit, if they haven’t done the homework to determine if it is a fit?” – Maria Popova [1:23:00] Maria Popova has written for amazing outlets like The Atlantic and The New York Times, but I find her most amazing project to be BrainPickings.org. Founded …

Foundation: Kevin Rose and Tim Ferriss

Kevin Rose and I go deep on a few subjects in this longer-format episode of “Foundation,” on which he’s interviewed many of my favorite entrepreneurs and investors, including Jack Dorsey (Twitter, Square) and Chris Sacca (Lowercase Capital), among others. I had a great time, as should be clear from the wine and laughter. It’s quite …