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 No. 97 “Naval Ravikant — The Person I Call Most for Startup Advice” and episode No. 341 “Nick Kokonas — How to Apply World-Class Creativity to Business, Art, and Life.”

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Links to everything discussed:
https://tim.blog/2024/05/16/naval-rav...

Timestamps:
[00:00] Start
[04:50] Notes about this supercombo format.
[06:09] Enter Naval Ravikant.
[06:21] On uncompromising honesty.
[08:21] What Naval looks for when deciding to invest in a founder.
[11:19] Recommended reading from outside the startup world.
[18:54] Who Naval considers successful.
[21:18] Cultivating non-judgmental awareness.
[26:24] How to replace bad habits with good habits.
[29:47] Naval's advice for his younger self.
[32:17] Naval's billboard.
[36:02] Enter Nick Kokonas.
[36:21] Is pressure Nick's default setting, or are perceived risks an illusion?
[37:11] How do behavioral economics and Richard Thaler influence Nick's approach?
[41:54] Nick's transition from philosophy to finance; was philosophy an asset?
[42:59] Why Nick's professor gave him shorter assignments than classmates.
[45:13] Nick's introduction to trading; dumbing down academics for clerk job.
[46:58] Why philosophy majors often become traders.
[47:35] Why Nick is glad he didn't pursue an MBA in 1992.
[48:57] Why Nick thinks his professor singled him out from his peers.
[53:08] Recommended books for aspiring entrepreneurs without philosophy background.
[57:47] Did being a Merc clerk meet Nick's expectations?
[1:00:18] How Nick followed his father's entrepreneurial model in trading.
[1:04:54] Why Nick left his mentor after a year to start his own company.
[1:05:57] How Nick and employees trained to quicken mental agility for trading.
[1:08:33] The moment Nick realized he could thrive in trading.
[1:09:18] Recommended resources for becoming a better investor.
[1:11:38] Nick seeks out "high, small hoops" for investment risks.
[1:14:16] Do businesses fail due to difficult model or lack of due diligence?
[1:17:11] When and why Nick decided to enter the restaurant business.
[1:18:42] The dinner leading to Nick and Grant Achatz's partnership.
[1:28:08] Why Nick chose to open a restaurant out of many risky options.
[1:30:49] How Nick spots talent early that others notice late.
[1:34:23] Questioning restaurant conventions like candles and white tablecloths.
[1:37:25] A now-famous chef was Alinea's first customer.
[1:38:19] Nick and Grant wouldn't let designers override their ideas.
[1:39:03] How Nick contributed effectively as a restaurant industry newcomer.
[1:14:35] Why Nick was "horrified" when Alinea won Best Restaurant in 2006.
[1:44:06] Grant's cancer diagnosis; writing a book and revolutionizing reservations.
[1:45:44] Traditional restaurant reservation systems and Nick's improvements.
[1:57:33] Bickering at press dinner; avoiding Next becoming "Disneyland of cuisine."
[2:02:30] Reservation software problems; variable pricing based on day of week.
[2:06:04] The moment Nick realized "This is the best thing I've ever built."
[2:07:57] Why the reservation system's rewards were worth the asymmetric risks.
[2:10:32] Using Marimekko charts to visualize restaurant and sponsorship data.
[2:17:13] The next industry Nick wants to disrupt: truffles.
[2:19:11] Illuminating black boxes.
[2:26:40] Self-selection of job roles; how Nick's hiring process has changed.
[2:32:17] Systems Nick uses to cope with a lot of email.
[2:37:59] Importance of engaging on social media, even if unable to respond to all.
[2:39:51] What "puzzle" filters and mini-hurdles in correspondence accomplish.
[2:40:52] Comparing similarities between the music and publishing industries.
[2:50:11] The agency problem as another black box.
[2:55:14] The Hembergers, The Alinea Project, and the upcoming independent Aviary Book.
[3:01:58] A brief discussion about cocktails.
[3:05:58] Books Nick has gifted most and how he personalizes gifts.
[3:08:26] Nick's billboard.

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