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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429 - I’m Having An Affair, What Should I Do?