Episode Details

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