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! Sponsors:Eight Sleep’s Pod 4 Ultra sleeping solution for dynamic cooling and heating: https://eightsleep.com/tim (save $350 on the Pod 4 Ultra)Momentous high-quality supplements: https://livemomentous.com/tim (code TIM for 20% off)LinkedIn Jobs recruitment platform with 1B+ users: https://linkedin.com/tim (post your job for free)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