Jan 20, 2025 · 55m · how-i-built-this
Resy and Eater: Ben Leventhal
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Serial entrepreneur Ben Leventhal details his journey revolutionizing the restaurant industry, from launching the digital food publication Eater to pivoting and selling reservation platform Resy to American Express, and pioneering dining loyalty with Blackbird Labs.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 34.1% of the talking time here. How this is scored →
Guy as informed peer 4.9 Guest teaching 3.4 Guest disagreement 1.6 Guy pushing back 2.7
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 32:22 Hospitality is not pure capitalism
Leventhal pushes back against Raz's comparison between concert ticket scalping and restaurant reservations, arguing that hospitality evokes intimate, egalitarian expectations that reject visible surge pricing.
Hardest push from Guy ▶ 37:50 Challenging vulnerability to OpenTableRaz directly challenges Resi's initial defensibility by pointing out that an 800-pound gorilla like OpenTable could have easily copied paid reservations had the idea gained massive traction.
Biggest teaching moment ▶ 25:04 The 10 out of 10 difficulty of restaurantsLeventhal educates the audience on why independent restaurants face orders of magnitude more complexity than standard retail by explaining on-demand assembly and bespoke service.
Guy holds their own ▶ 26:18 Raz lays out restaurant cost structureRaz demonstrates domain knowledge by breaking down the 30% rent, 30% food, and 30% labor breakdown required to squeeze out a modest 10% profit margin.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Early Media Days at VH1 and She Loves New York | 4 | 2 | 1 | 1 | Guy Raz adds historical context regarding the inflated prestige and high executive perks of 2000s New York media culture. Leventhal pleasantly clarifies the tone and genesis of his early newsletter She Loves New York. | |
| Partnering with Lockhart Steele to Co-Found Eater | 4 | 2 | 1 | 2 | Raz explores the economics of early digital media and Gawker's ecosystem in 2005. Leventhal explains why Eater deliberately refrained from professional food reviews and food photography to focus on blogging cadence. | |
| Disrupting Food Journalism and Navigating Industry Tension | 5 | 3 | 2 | 4 | Raz presses Leventhal on Eater's early aggressive snark, specifically the 'Death Watch' column and friction with publicists. Leventhal concedes the harshness of their outsider approach while explaining how digital media disrupted traditional embargo rules. | |
| Leaving Eater, Kitchen Surfing, and Gary Vaynerchuk | 6 | 4 | 1 | 1 | Raz and Leventhal engage in a knowledgeable exchange regarding restaurant profit margins and operational hurdles. Raz articulates the classic one-third cost structure while Leventhal emphasizes the unmatched complexity of food service production. | |
| Conceptualizing Resy and the Flaws of Surge Pricing | 6 | 5 | 3 | 5 | Raz questions the surge pricing reservation model, comparing it to secondary concert ticketing and noting the competitive threat from OpenTable. Leventhal counters that hospitality triggers unique consumer expectations of democracy and intimacy that resist overt dynamic pricing. | |
| Pivoting Resy to Flat-Rate Table Management Software | 5 | 4 | 1 | 3 | Raz notes that switching to flat monthly SaaS pricing requires huge sales scale compared to commission models. Leventhal details how customer requests and innovative features like universal group databases allowed Resi to compete with incumbents. | |
| Acquisition by American Express and Navigating COVID-19 | 4 | 4 | 2 | 3 | Raz probes the mechanics of Leventhal's new venture, Blackbird Labs, seeking clarity on whether it relies on speculative cryptocurrency or loyalty points. Leventhal clarifies that the tokens are USD-backed rewards functioning like airline loyalty alliances. |
Statements from this episode (16)
Leventhal: Eater avoided reviews and photos at launch to prioritize publishing speed
“Now, we did say, we're not gonna write reviews. And we also said, we're not going to post photos of food. And we said, we're really not interested in, in adding to the noise with more photos of food. And we're really not interested in writing reviews because w…”
Ben Leventhal: Eater's 'Death Watch' was harsh and cruel in hindsight
“Knowing what I know now, I wouldn't do things like death watch, which in hindsight were harsh and cruel to the restaurants that became its subjects.”
Ben Leventhal: Early online media prioritized publishing speed over accuracy
“The priority was pace and speed, and certainly that took precedence over, I would say, accuracy in some cases.”
Leventhal: Independent restaurants with 10% profit margins are crushing it
“If you're running a 10% as an independent restaurant, you're crushing it.”
Leventhal: Restaurants are orders of magnitude harder than other small businesses
“If you think about the moving parts at the average independent restaurant and how complicated The production and assembly and delivery of food is to the table, and you compare that to any other small business, it's orders of magnitude more difficult.”
Leventhal: Resy initially took a 20% cut on paid table reservations
“My recollection is that we took 20% as a vig, and the restaurant kept the rest.”
Leventhal: Consumers resist surge pricing because restaurants feel democratic
“There's something about hospitality that forces consumers into a different mental model than they are using for other Entertainment categories. And I think it's the intimacy of it. I think it's the legacy and the history of hospitality. Restaurants in people's…”
Leventhal: OpenTable consciously passed on replicating Resy's early table pricing features
“The fact of the matter is open table saw that we were doing a couple of things and entirely passed on doing them. They saw that we were pricing tables and we were also distinguishing tables. We said, you know, not all restaurant tables are created equal.”
Leventhal: Metering restaurant software fees based on booking volume is insane
“The idea that more successful restaurants pay more is insane. You pay us a flat fee. Use the software as much as you want it.”
Leventhal: Airbnb agreed to both invest in Resy and partner commercially
“At some point in that conversation, we said, you know, we'd like this to be both an investment and a commercial partnership, and they agreed.”
Leventhal: Pre-Resy reservation software lacked centralized multi-unit guest databases
“Before Resi came along, every individual restaurant unit had its own customer database. It was essentially a customer database on a local server, and from the start, we said, you're, you know, if you have four restaurants, it's all one database.”
Leventhal: Resy was not profitable when acquired by American Express
“We were in sight of it when we sold it to Amex. We were not profitable.”
Leventhal: Resy cut fees to zero during COVID, setting industry precedent
“We did two things, and we did them very fast, and then the industry followed. One is, we cut fees to zero. We thought it was really important, symbolically, to say, we are not in a position to be collecting money from restaurants right now, and a lot of the in…”
Leventhal: Blackbird Labs backstops all loyalty points with US dollars
“We backstop all of the points with USD. So restaurants know at any time they can sell us their points for USD.”