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.” 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) Links to everything discussed: https://tim.blog/2024/05/16/naval-ravikant-and-nick-kokonas/ 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. Sign up for "5-Bullet Friday" (Tim's free weekly email newsletter): https://go.tim.blog/5-bullet-friday-yt/ Follow the Tim Ferriss Podcast: https://tim.blog/podcast/ Visit the Tim Ferriss Blog: https://tim.blog/ Follow Tim Ferriss on Twitter: https://twitter.com/tferriss/ Follow Tim Ferriss on Instagram: https://www.instagram.com/timferriss/