#737: Naval Ravikant and Nick Kokonas

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
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Gilbert, Terry Crews, Sia, Yuval Noah
Harari, Malcolm Gladwell, Madeleine
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Karr, Maria Popova, Sam Harris, Michael
Phelps, Bob Iger, Edward Norton, Arnold
Schwarzenegger, Neil Strauss, Ken Burns, Maria
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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
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