/Nick Kokonas — How to Apply World-Class Creativity to Business, Art, and Life (#341)

Nick Kokonas — How to Apply World-Class Creativity to Business, Art, and Life (#341)

“I just look at some things and go, ‘Why is that? Why does it work that way?’ Oftentimes, the people most entrenched in a system have no idea why.”
— Nick Kokonas

Nick Kokonas (IG: @nkokonas, TW: @NickKokonas) is the co-owner and co-founder of The Alinea Group of restaurants, which includes Alinea, Next, The Aviary, Roister, and The Aviary NYC. He is also the founder and CEO of Tock, Inc, a reservations and CRM system for restaurants with more than 2.5M diners and clients in more than 20 countries.

Alinea has been named the Best Restaurant in America and Best Restaurant in The World by organizations and lists as diverse as The James Beard Foundation, World’s 50 Best, TripAdvisor, Yelp, Gourmet Magazine, and Elite Traveler. His restaurants have won nearly every accolade afforded to them.

Nick has been a subversive entrepreneur and angel investor since 1996. He spent a decade as a derivatives trader, has co-written three books, and believes in radical transparency in markets and business. His latest effort is The Aviary Cocktail Book, which is perhaps the most gorgeous book I’ve ever seen. It is self-published, has already pre-sold nearly $1M in copies, and is being released and shipped in October of 2018.

We’ve been trying to get this interview going ever since Nick was of immense help to me for The 4-Hour Chef, so I hope you enjoy this as much as I did. We talk about much more than the restaurant business, including philosophy, derivatives trading, favorite books, and how Nick tends to break every industry he enters in the most productive way possible! Enjoy!

Want to hear another episode with someone else who understands that the most interesting way to do something isn’t always the easiest? — Listen to this episode with Astro Teller, CEO of X on moonshot thinking, mutilated checkerboards, “safety third,” and much more. (Stream below or right-click here to download.):

This episode is brought to you by 99designs, the global creative platform that makes it easy for designers and clients to work together. From logos to apps and packaging to books, 99designs is the go-to design resource for any budget.

Right now, my listeners can get 50 dollars off a logo and brand identity package from 99designs, plus a free upgrade that lets you promote your project on the platform (an additional 99 dollar value), by visiting 99designs.com/Tim50.

This episode is also brought to you by Charlotte’s Web, which makes a CBD oil, a hemp extract, that has become one of my go-to tools. Charlotte’s Web won’t get you high, but it does have some pretty powerful benefits, and it works with your body’s existing endocannabinoid system. Some of the most common uses are for relief from everyday stressors, help in supporting restful sleep, and to bring about a sense of calm and focus.

Visit cwhemp.com/tim to take a quick quiz, which will determine the best product for your lifestyle. Charlotte’s Web is also offering listeners of this podcast 10% off with discount code TIM.

QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…


  • Connect with Nick Kokonas:

The Alinea Group | Tock | Twitter | Instagram | Facebook


  • Is pressure Nick’s default setting, or are the risks the world perceives he takes somewhat of an illusion? [09:35]
  • How do behavioral economics and Nobel Prize-winning investor Richard Thaler fit into Nick’s way of doing things? [12:35]
  • How did Nick make the transit from philosophy to finance, and does he feel philosophy was an asset to what came later? [14:55]
  • Why did a legendary philosophy professor at Colgate give Nick’s classmates 15-page assignments while capping his limit at three pages? [16:21]
  • What was Nick’s introduction to the world of trading at a time when his future father-in-law was predicting he’d become an intellectual bum, and why did he have to dumb down the academics on his rÈsumÈ to get a clerk job on the Merc floor? [18:12]
  • Why is it common for philosophy majors to become traders? [21:03]
  • Why Nick is glad he didn’t pursue an MBA in 1992. [22:00]
  • Going back to Nick’s professor at Colgate, why does he think he was singled out from his peers? [23:48]
  • Books and other resources Nick recommends for aspiring entrepreneurs who don’t have the benefit of a philosophy background (or a tough professor to keep them grounded). [28:15]
  • Did Nick find that being a clerk on the floor of the Merc was everything he dreamed it could be? [33:48]
  • How Nick followed his entrepreneurial father’s model for owning his own situation when entering the world of trading, and found someone who was doing business in a way no one else was doing it. [36:10]
  • Why did Nick leave his mentor after a year and start his own company? [40:53]
  • How did Nick and his employees train to quicken their mental agility required for trading? [42:34]
  • The formative moment when Nick realized he could thrive in the trading environment. [45:31]
  • Resources and books Nick recommends to anyone who wants to learn to become a better investor. [46:21]
  • When it comes to taking investment risks these days, Nick seeks out the “high, small hoops.” [48:22]
  • Averages can be misleading. Do so many businesses fail because the model is difficult, or because too few do enough due diligence before diving into the fray? [52:00]
  • At what point did Nick decide to leave trading and get into the restaurant business — in spite of being warned of the high failure rate to be found there? [55:15]
  • The dinner and conversation that led to Nick teaming up with Grant Achatz — even though they didn’t really know each other very well by that point — and the decisions they made together along the way. [1:00:18]
  • Out of so many equally risky and exciting options, why did Nick pick opening a restaurant as his next “thing?” [1:07:17]
  • How does Nick spot talent early in others that most people are late to notice? [1:10:23]
  • Why do restaurants have candles, why do fancy restaurants have white tablecloths, and other questions that Nick and Grant have pondered. [1:14:22]
  • Incidentally, a now-famous chef was Alinea’s first customer. [1:17:25]
  • Nick and Grant would never let an architect or designer shoot down their ideas just because the way things have always been done happen to be practical. [1:18:39]
  • As someone who had never run a restaurant before, how did Nick contribute to the business effectively without simply falling into the role of financial donor dilettante? [1:19:29]
  • Why was Nick “horrified” when Alinea won Best Restaurant in America from Gourmet magazine in 2006? [1:23:24]
  • Grant was diagnosed with stage IV cancer and given six months to live — so of course he and Nick wrote a book and worked on revolutionizing the way their industry handled reservations while supervising a dwindling staff. [1:24:51]
  • Sometimes a PoS really is a PoS. Nick explains how reservations have been traditionally booked in the restaurant industry and what he’s done to improve upon this in ways that go beyond holding a table. [1:29:29]
  • Partner bickering at a time-traveling press dinner and using austere minimalism to avoid Next becoming the Disneyland of cuisine. [1:39:51]
  • Dealing with reservation software problems seven hours before the first dinner and the novelty of variable price points based on the day of the week. [1:44:58]
  • The moment a bearded, unwashed, and somewhat slightly dazed Nick was able to say “This is the best thing I’ve ever built.” [1:47:44]
  • Why the rewards of such a reservation system were worth their asymmetric risks on several levels. [1:51:02]
  • Marimekko charts can be used to instantly see anything from how much your restaurant’s sending to the fishmonger every month to what the ROI of sponsoring a podcast might be. [1:55:15]
  • The next industry Nick wants to disrupt? Truffles. Here’s why. [2:00:41]
  • How does Nick choose the black boxes worth trying to illuminate and examine, and what role do his more ambitious employees play in bringing them to light? [2:04:24]
  • On the confining self-selection of roles many people fall into on the job (for better or for worse), and how Nick’s hiring process is different today than it was 20 years ago. [2:10:31]
  • Nick deals with a lot of email. What systems does he have in place to help him cope? [2:16:41]
  • Social media can be hard to keep up with, but we both agree it’s important to demonstrate that we’re paying attention by engaging when possible — even if we can’t respond to it all. [2:22:49]
  • What “puzzle” filters and other mini-hurdles in correspondence accomplish. [2:24:06]
  • We compare notes about the somewhat slimy similarities between the music and publishing industries. [2:26:02]
  • Another black box: the agency problem. [2:35:25]
  • On the Hembergers and The Alinea Project, and the upcoming Aviary Book being released independently. [2:41:23]
  • A little cocktail talk. [2:48:37]
  • Books Nick has gifted most, and how he personalizes the gifts he gives. [2:53:47]
  • What would Nick’s billboard say? [2:55:44]
  • Parting thoughts. [2:57:34]


Posted on: October 18, 2018.

Please check out Tribe of Mentors, my newest book, which shares short, tactical life advice from 100+ world-class performers. Many of the world’s most famous entrepreneurs, athletes, investors, poker players, and artists are part of the book. The tips and strategies in Tribe of Mentors have already changed my life, and I hope the same for you. Click here for a sample chapter and full details. Roughly 90% of the guests have never appeared on my podcast.

Who was interviewed? Here’s a very partial list: tech icons (founders of Facebook, Twitter, LinkedIn, Craigslist, Pinterest, Spotify, Salesforce, Dropbox, and more), Jimmy Fallon, Arianna Huffington, Brandon Stanton (Humans of New York), Lord Rabbi Jonathan Sacks, Ayaan Hirsi Ali, Ben Stiller, Maurice Ashley (first African-American Grandmaster of chess), Brené Brown (researcher and bestselling author), Rick Rubin (legendary music producer), Temple Grandin (animal behavior expert and autism activist), Franklin Leonard (The Black List), Dara Torres (12-time Olympic medalist in swimming), David Lynch (director), Kelly Slater (surfing legend), Bozoma Saint John (Beats/Apple/Uber), Lewis Cantley (famed cancer researcher), Maria Sharapova, Chris Anderson (curator of TED), Terry Crews, Greg Norman (golf icon), Vitalik Buterin (creator of Ethereum), and nearly 100 more. Check it all out by clicking here.