Dec 13, 2023 · 1h 1m · lennys-podcast
Failure
Tom Conrad · 11m spoken Gina Gotthilf · 10m spoken Lenny Rachitsky · 10m spoken Paul Adams · 7m spoken Sri Batchu · 4m spoken Katie Dill · 4m spoken Jiaona Zhang · 3m spoken Maggie Crowley · 1m spoken
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this special compilation episode of Lenny's Podcast, host Lenny Rachitsky brings together prominent tech leaders to candidly dissect high-stakes product failures, market timing miscalculations, and mortifying career setbacks. Through transparent retrospectives from Airbnb, Facebook, Google, Pets.com, Duolingo, and Quibi, the guests illustrate how embracing vulnerability and disciplined experimentation turns professional failure into a catalyst for growth.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Lenny holds 19% of the talking time here. How this is scored →
Lenny as informed peer 3.6 Guest teaching 5.4 Guest disagreement 0.4 Lenny pushing back 0.7
speaking balance: gold is Lenny, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:00:04 Maggie Crowley's categorical rejection of rewrites
Maggie passionately and emphatically rejects the conventional urge to rewrite codebases, flatly telling listeners 'Just don't do it. Don't rewrite.'
Hardest push from Lenny ▶ 38:34 Lenny pushes back on bundled experiment tacticsLenny challenges Sri Batchu's maximal experiment design by pointing out that bundling every lever prevents teams from knowing which specific factor caused the failure.
Biggest teaching moment ▶ 29:00 Tom Conrad re-educates on macro unit math vs product polishConrad delivers an eye-opening conceptual breakdown of Quibi, explaining that companies are math equations where product execution cannot overcome a fundamentally broken capitalization model.
Lenny holds their own ▶ 42:10 Lenny demonstrates deep marketplace economics expertiseLenny draws directly upon his operational experience at Airbnb to articulate why physically vetting properties and sending amenities could never scale economically.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Lenny as informed peer | Guest teaching | Guest disagreement | Lenny pushing back | Why |
|---|---|---|---|---|---|---|
| Katie Dill on Leading Design and Earning Team Trust | 1 | 5 | 0 | 0 | Lenny acts purely as a curator and sympathetic listener while Katie Dill walks through her formative leadership failure at Airbnb. Dill explains the crucial lesson of earning trust rather than forcing organizational change top-down. | |
| Paul Adams on Freezing During Cannes Keynote Presentation | 2 | 4 | 0 | 0 | Paul Adams recounts freezing on stage at Cannes and how recovering from worst-case scenarios builds resilience. Lenny empathizes by sharing his own dread of public speaking. | |
| Paul Adams on Google Failures and Intercom Culture | 3 | 6 | 0 | 0 | Adams provides detailed insight into how fear-driven culture doomed Google Buzz and Google Plus, contrasted with Intercom's ship-to-learn philosophy. Lenny prompts on cultural tension and transitions. | |
| Tom Conrad on Pets.com Collapse and Market Timing | 3 | 6 | 1 | 0 | Tom Conrad educates listeners on the forgotten reality of Pets.com, correcting common assumptions by noting they returned remaining capital rather than going bankrupt. Lenny cites the rapid 19-month rise-and-fall timeline. | |
| Tom Conrad on Quibi Missteps and Content Math | 2 | 7 | 0 | 0 | Conrad delivers a masterclass on startup failure, explaining that company success is a foundational math problem that product iteration cannot fix if the core capital equation is broken. | |
| Sri Batchu on Designing Experiments to Fail Conclusively | 5 | 6 | 1 | 4 | Sri Batchu advocates maximizing treatment effects to fail conclusively in B2B growth. Lenny pushes back directly by highlighting that multi-variable testing obscures which individual lever actually failed. | |
| Jay Zhang on Solution-First Traps and Airbnb Plus | 6 | 5 | 0 | 1 | Jay Zhang and Lenny analyze the failure of Airbnb Plus. Lenny leverages his own Airbnb tenure to dissect unit economics, operational mismatches, and the impracticality of physical inspections. | |
| Gina Gotthilf on Career B-Sides and Duolingo Mistakes | 4 | 6 | 0 | 0 | Gina Gotthilf shares vulnerable career B-sides and specific internationalization and dogfooding missteps at Duolingo. Lenny shares his own multi-career pivot perspective. | |
| Maggie Crowley on Rewrites and Shipping Flawed Products | 6 | 4 | 2 | 1 | Maggie Crowley passionately cautions PMs against side-by-side product rewrites based on a multi-year failure. Lenny demonstrates deep PM domain knowledge by explaining how teams get trapped in negative redesign experiment loops. |
Statements from this episode (20)
Facebook tapped Paul Adams for Cannes keynote after Zuckerberg's privacy grilling
“And the year prior, Zuck had been interviewed. He was the speaker. He'd been interviewed. He'd gotten a hard time on privacy. It didn't go well as well as they'd hoped. So the next year they asked me to do it.”
Google Buzz and Google+ were driven by competitive fear, says Paul Adams
“I think a lot of the motivation for those projects came from a place of fear. You know, it didn't come from a place of let's make a great product for people. Let's like really understand the things people struggle with when communicating with family and friend…”
Google segregated the Google+ team in a restricted, keycard-access-only building
“Google had done a lot of things at the time that, that, that were the first for them. I don't know if they've done them since, but things like everyone worked in Google plus was sent to a different building that building a different key card. If you didn't wor…”
Google quarantined Paul Adams and forensically analyzed his laptop upon his exit
“When I left Google kind of assumed that I was one of the spies, you know, I was quarantined when I told them I was leaving. They you know, forensically analyzed my laptop, like all sorts of stuff like that.”
Conrad: Pets.com and rivals each raised over $50 million
“One of the things that happened was that there were three kind of overfunded pet e-commerce sites, and we all raised in excess of fifty million dollars”
Pets.com failed because 80% of users were on dial-up, says Tom Conrad
“The critique that is often leveled at Pets.com, or at least at the time was like, this is just a stupid business. They're shipping dog food around. You could never make that work. And like that that's just wrong. Like you absolutely can make it work. Probably …”
Pets.com didn't go bankrupt; it shut down and returned cash to investors
“We actually didn't go bankrupt. We shut the company down and returned the remaining balance to the investors, which no public company had ever done before.”
Conrad: Product iteration cannot rescue a fundamentally broken business equation
“Companies are also kind of like a, they're kind of a math problem that describes how you take, you know, investment and pour them into the equation and out the other side comes returns on some time horizon. And yes, There are variables in that equation that ar…”
Quibi produced 70 shows in 18 months before shutting down
“We made 70 shows. In 18 months, which is like more content than all of the major broadcast networks combined made in a single year.”
Making Quibi successful would have required a $10 billion content library
“Pretty quickly became clear that the math was just wrong. It wasn't going to take two billion. It was going to take six or eight or ten billion. And the risk reward profile of betting ten billion on the format was just more than anyone can stomach.”
Batchu: Growth experiments typically have only a 30% success rate
“Growth experiments in my history are typically like, 30 percent-ish success rate. So the vast majority of things that you try don't work.”
B2B growth teams should maximize treatment effects to overcome low sample sizes
“In B to B, you don't usually have the luxury of large N, which you do in consumer, right? You know, Facebook can get stats in two hours. You know, a B to B company could take two years to get to get to the same number of, you know, touch points. And so to coun…”
Product teams shouldn't rely on magical thinking to fix unit economics later
“There are things where I think you have like magical thinking around unit economics. You're like, well, when we get to the scale of X, it's all going to work out. We can make these things happen. I think you actually need to really make sure the unit economics…”
Airbnb Plus unit economics never would have worked out, says Jiaona Zhang
“And so I, yeah, I personally don't believe the unit economics ever would have really worked out. I think we should have known that we should have dug into that more at the very beginning”
Gotthilf: More than 50% of Duolingo's growth A/B tests failed
“More than 50% of our A-B tests didn't work out. We made bets that didn't make sense.”
Gotthilf: Desirable user badges can be leveraged to drive almost any product metric
“Once you have badges and people want them, you can now ask people to do anything like go find friends. Go buy things like, you know, whatever it is. And so like we had, we impacted almost all metrics across the company positively, including some we hadn't expe…”
Duolingo hit 1M day-one downloads in China before a government ban
“I went and launched Duolingo in China, and it got downloaded by a million people in the first day, and then the app got blocked, and we, you know, because of the government, and then we couldn't figure out what to do, and then everyone rated the app, like, one…”
Duolingo discovered most Indian smartphone users set their phone UI to English
“We launched Duolingo in India and didn't realize, because we couldn't have unless we went there, which we finally did, that most people set their phones, phone UI in India to English.”
Product managers aren't great until they've shipped a bad product, says Crowley
“A question I ask in every product interview is what's the worst product you've ever shipped? And that's because I don't think you're a good PM if you haven't shipped something that's really shitty. Like, you just haven't had enough reps, you haven't done it en…”