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:
[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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