Navigating Risk and Decision-Making

This episode is a two-for-one, and that’s because the podcast recently hit its 10-year anniversary and passed one billion downloads. To celebrate, I’ve curated some of the best of the best—some of my favorites—from more than 700 episodes over the last decade. I could not be more excited. The episode features segments from episode #97 "Naval Ravikant — The Person I Call Most for Startup Advice" and episode #341 "Nick Kokonas — How to Apply World-Class Creativity to Business, Art, and Life."

Please enjoy!

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Timestamps:

[00:00] Start

[04:34] Notes about this supercombo format.

[05:53] Enter Naval Ravikant.

[06:05] On uncompromising honesty.

[08:05] What Naval looks for when deciding to invest in a founder.

[11:03] Recommended reading from outside the startup world.

[18:38] Who Naval considers successful.

[21:02] Cultivating non-judgmental awareness.

[26:08] How to replace bad habits with good habits.

[29:31] Naval's advice for his younger self.

[32:01] Naval's billboard.

[35:46] Enter Nick Kokonas.

[36:05] Is pressure Nick's default setting, or are perceived risks an illusion?

[36:55] How do behavioral economics and Richard Thaler influence Nick's approach?

[41:38] Nick's transition from philosophy to finance; was philosophy an asset?

[42:43] Why Nick's professor gave him shorter assignments than classmates.

[44:57] Nick's introduction to trading; dumbing down academics for clerk job.

[46:42] Why philosophy majors often become traders.

[47:19] Why Nick is glad he didn't pursue an MBA in 1992.

[48:41] Why Nick thinks his professor singled him out from his peers.

[52:52] Recommended books for aspiring entrepreneurs without philosophy background.

[57:31] Did being a Merc clerk meet Nick's expectations?

[1:00:02] How Nick followed his father's entrepreneurial model in trading.

[1:04:38] Why Nick left his mentor after a year to start his own company.

[1:05:41] How Nick and employees trained to quicken mental agility for trading.

[1:08:17] The moment Nick realized he could thrive in trading.

[1:09:02] Recommended resources for becoming a better investor.

[1:11:22] Nick seeks out "high, small hoops" for investment risks.

[1:14:00] Do businesses fail due to difficult model or lack of due diligence?

[1:16:55] When and why Nick decided to enter the restaurant business.

[1:18:26] The dinner leading to Nick and Grant Achatz's partnership.

[1:27:52] Why Nick chose to open a restaurant out of many risky options.

[1:30:33] How Nick spots talent early that others notice late.

[1:34:07] Questioning restaurant conventions like candles and white tablecloths.

[1:37:09] A now-famous chef was Alinea's first customer.

[1:38:03] Nick and Grant wouldn't let designers override their ideas.

[1:38:47] How Nick contributed effectively as a restaurant industry newcomer.

[1:14:19] Why Nick was "horrified" when Alinea won Best Restaurant in 2006.

[1:43:50] Grant's cancer diagnosis; writing a book and revolutionizing reservations.

[1:45:28] Traditional restaurant reservation systems and Nick's improvements.

[1:57:17] Bickering at press dinner; avoiding Next becoming "Disneyland of cuisine."

[2:02:14] Reservation software problems; variable pricing based on day of week.

[2:05:48] The moment Nick realized "This is the best thing I've ever built."

[2:07:41] Why the reservation system's rewards were worth the asymmetric risks.

[2:10:16] Using Marimekko charts to visualize restaurant and sponsorship data.

[2:16:57] The next industry Nick wants to disrupt: truffles.

[2:18:55] Illuminating black boxes.

[2:26:24] Self-selection of job roles; how Nick's hiring process has changed.

[2:32:01] Systems Nick uses to cope with a lot of email.

[2:37:43] Importance of engaging on social media, even if unable to respond to all.

[2:39:35] What "puzzle" filters and mini-hurdles in correspondence accomplish.

[2:40:36] Comparing similarities between the music and publishing industries.

[2:49:55] The agency problem as another black box.

[2:54:58] The Hembergers, The Alinea Project, and the upcoming independent Aviary Book.

[3:01:42] A brief discussion about cocktails.

[3:05:42] Books Nick has gifted most and how he personalizes gifts.

[3:08:10] Nick's billboard.

[3:09:49] Parting thoughts.

*

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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, Margaret Atwood, Mark Zuckerberg, Peter Thiel, Dr. Gabor Maté, Anne Lamott, Sarah Silverman, Dr. Andrew Huberman, and many more.

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