All podcasts / Invest Like the Best / Summary

Nick Kokonas - Know What You Are Selling (REPLAY)

2025-12-30 - 76 min - source - Read full transcript
Patrick O'Shaughnessy (host)Nick Kokonas

Key insights

Most businesses, restaurants especially, are actually selling several distinct products bundled into one undifferentiated offer, and simply naming and selling each one separately unlocks revenue without changing costs.
Using Gramercy Tavern as the example, Kokonas counts eight separate things being sold under one roof - the bar, casual dining, a-la-carte, two tasting menus, wine pairings, private dining, and merchandise - yet the restaurant only ever asks a guest 'are you showing up.' Segmenting and selling each experience separately, he argues, is how you sell 100 tasting menus with certainty on a Saturday instead of hoping 4% of walk-ins opt in.
know-what-youre-selling
Any business that sells access to a specific time slot should price that slot dynamically, because demand is never flat across the week.
Kokonas generalizes from options theory: restaurants, salons, dentists, and personal trainers all have predictably uneven demand (Saturday night versus Tuesday at 6am) yet almost none of them price for it. He argues the tools for dynamic pricing already exist for hard goods (Amazon, Shopify) and will inevitably extend to time-slotted services.
dynamic-pricing-and-behavioral-economics
Ticketed, prepaid restaurant reservations function like expiring options and were costing Alinea over a million dollars a year in unrealized revenue before Tock existed.
Kokonas found guests routinely lied about party size to secure a table, and the restaurant routinely lied back about table availability to avoid losing bookings, both of which produced empty seats or forgone revenue that compounded across hundreds of nights a year. Selling tickets with a deposit, the way concerts and sports do, removed both incentives to lie.
dynamic-pricing-and-behavioral-economics
A slim statistical edge, applied to a high volume of independent decisions, is a more repeatable path to wealth than trying to be right most of the time.
Drawing on his background as a derivatives trader, Kokonas frames his own version of the casino's edge: being wrong nearly half the time is fine if you make enough independent, measurable decisions and the edge is real, and treating each decision's outcome as data rather than a referendum on self-worth is what lets a business keep making decisions instead of freezing up after failures.
founder-decision-making
Deliberately choosing your first customers, and just as deliberately refusing customers before you can serve them well, determines a business's long-term trajectory.
Tock targeted high-end restaurants first (the 'Tesla approach') because they could prove clear ROI and tolerate risk, rather than racing competitors to give away a free, undifferentiated product to price-sensitive customers. Kokonas also turned away restaurants that wanted to sign up before Tock had features they needed, judging that serving them poorly would have been worse than losing the deal.
founder-decision-making
Prepaying suppliers can unlock steep discounts by eliminating the supplier's own risk, not just by improving the buyer's cash position.
Kokonas called a beef vendor and offered to prepay four months of a $300,000 order; the vendor cut the price from $34 to $18 a pound because prepayment removed the vendor's exposure to unsold, spoiling dry-aged beef past its 35-day sell window. He generalizes this as evidence that most restaurants treat float purely as cash-management, missing a much larger margin lever.
restaurant-business-economics
Self-publishing is a far better business than working with a traditional publisher once you already have an audience, because standard publishing contracts hide thin actual printing costs.
Kokonas describes calling Chinese printers directly and finding a $50 retail book costs about $2 to print, while typical publisher terms pay the author roughly 10% of cover price, require a 5,000-copy self-order, and offer an advance that Kokonas argues represents real risk-free profit for the publisher. His group now publishes its own books and sold $120,000 of them in a single week, at higher margins than the restaurants themselves.
restaurant-business-economics
Capturing a customer's email, not their phone number, is the single highest-leverage piece of data a service business can collect, and most booking software deliberately withholds it from the business.
Kokonas calls this 'stranger danger': without an email identifier, a restaurant has no way to recognize a repeat guest, personalize their experience, or build lookalike audiences on Facebook and Instagram. He argues incumbent booking platforms resist surfacing this data because owning the customer relationship, not the restaurant, is how they monetize.
know-what-youre-selling
Recognizing a low-probability, high-severity risk early, and acting on it before it's socially acceptable to do so, requires tolerating looking irrational to your own team.
Kokonas describes instituting temperature checks, mask wearing, and mandatory hand-washing at his restaurants two and a half weeks before Chicago's shutdown, based on reading officials' visible panic on TV rather than their public reassurances. He was initially seen as 'unhinged' by staff, and only enforced compliance by threatening termination once he judged the stakes were existential.
covid-crisis-response
Because Tock was cloud-based and already built around time-slotted, dynamically priced inventory, it could pivot an entire restaurant group to carryout in about a week when COVID hit.
Twenty designers and engineers worked around the clock to launch a carryout product for Canlis in Seattle, then for Alinea itself, which began selling $35 beef Wellingtons three days after Chicago's shutdown and reached $1,000 nightly carryout sales within a week. Tock then undercut DoorDash-style delivery apps' 20-30% commissions with a flat 3% fee, arguing the pandemic exposed how unsustainable that take rate was once delivery became restaurants' only revenue source rather than supplemental income.
covid-crisis-response

Media referenced

Companies

Techniques and frameworks

Summary

This is a replay of Patrick O'Shaughnessy's November 2020 Founder's Field Guide conversation with Nick Kokonas, the philosophy-major-turned-derivatives-trader who co-founded Alinea, Next, and The Aviary and built the reservations and payments company Tock. The conversation opens with Kokonas unpacking his own three-part formula for wealth creation - own something, make lots of decisions that have measurable outcomes, and be right just slightly more than half the time, repeated at volume - a framework he traces to growing up in a Greek immigrant family in Chicago and later trading derivatives, where the goal was never to be right most of the time but to run the house's edge across enough independent bets.

The bulk of the episode is a granular tour of how Kokonas rebuilt restaurant economics around a single idea: know what you're selling, then actually sell it. Using Gramercy Tavern as a case study, he shows that a single restaurant is really selling eight distinct products (bar seating, casual dining, a-la-carte, two tasting menus, wine pairings, private dining, and merchandise) but almost never differentiates the offer to a guest before they arrive. This connects to his broader argument, carried over from his trading background, that any time-slotted business should price dynamically, and that ticketed, prepaid reservations function like expiring options - eliminating the mutual lying between restaurants and guests over table sizes and availability that was costing Alinea over a million dollars a year before Tock existed. He walks through Next's 2011 launch, where ticketed dining sold $562,000 on day one despite near-universal skepticism from his own team and from VCs who insisted he needed a cheap, freemium, B2C strategy instead of starting with high-end restaurants that could prove the model.

Several tangents flesh out the same "know what you're selling" thesis in adjacent domains. Kokonas describes calling suppliers directly to prepay for goods months in advance, discovering that a beef vendor would cut prices in half because prepayment eliminated the vendor's own risk of spoiled, unsold dry-aged product - a lever he argues most restaurants ignore because they treat float purely as a cash-management tool. He makes a similar case for self-publishing: after learning that a $50 book costs roughly $2 to print, he began publishing his own group's books rather than accepting standard contracts that pay authors around 10% of cover price, and now runs a materially better-margin business than the restaurants themselves. Throughout, he repeats a related principle he calls "stranger danger": most restaurants have no way to identify a repeat customer because they never capture an email address, the durable identifier that lets any business remarket, personalize, and build lookalike audiences the way Amazon or Netflix do.

The episode closes with an account of Tock's response to COVID, which Kokonas frames as a direct extension of the same probabilistic-thinking training that shaped his trading and restaurant careers. He describes recognizing the pandemic as a low-probability but existential risk weeks before Chicago's shutdown, instituting safety protocols that made him look "unhinged" to his own staff, and then leading a week-long sprint to rebuild Tock into a carryout and delivery platform - first for Canlis in Seattle, then for his own restaurants, which went from $35 beef Wellingtons to $1,000 nightly carryout sales within days. He positions Tock's flat 3% take rate as a direct challenge to third-party delivery apps charging 20-30%, arguing that rate only survived as long as delivery was supplemental restaurant revenue rather than a primary lifeline. The conversation ends, as the original Founder's Field Guide episodes did, with Patrick's closing question about the kindest thing anyone has done for Kokonas, prompting a story about an employee who returned a stolen restaurant napkin embedded in the handle of a hand-forged knife.

Notable Quotes

"Own something, make lots of decisions that have outcomes, try to be right 51% of the time, do that often and repeat." - Nick Kokonas

"Know what you're selling and then actually sell it, which sounds incredibly obvious. It's so stupid. I'm telling you what, there should be a business course on that." - Nick Kokonas

"People can't buy what you don't sell." - Nick Kokonas

"I like businesses that are hard because if I can figure them out... I just go like, well, people are full of shit. They're defending their position." - Nick Kokonas

"The concept of the phrase burn in a startup is just the worst word in the world because I'm not burning money, I'm investing it." - Nick Kokonas