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.