Failure

Failure

Lenny's PodcastDec 13, 20231h 1m

Lenny Rachitsky (host), Guest (Airbnb leader sharing an intervention story) (guest), Paul Adams (guest), Guest (brief laugh only) (guest), Tom Konrad (guest), Guest (growth/experiments story) (guest), Guest (Airbnb Plus failure story) (guest), Guest (Duolingo failures/B-sides story) (guest), Maggie Crowley (guest)

Leadership failures and rebuilding trust with teamsFear-driven strategy vs. customer-driven product buildingExperimentation culture, conclusive failure, and learning velocityUnit economics, timing, and structural flaws in business modelsSolution-first thinking vs. problem-first product discoveryThe hidden ‘B-side’ of careers: layoffs, missteps, and nonlinear pathsCommon product traps: rewrites, over-operations, and vanity bets

In this episode of Lenny's Podcast, featuring Lenny Rachitsky and Guest (Airbnb leader sharing an intervention story), Failure explores how Product Leaders Turn Painful Failures Into Career-Defining Lessons This compilation episode of Lenny's Podcast assembles candid stories of failure from top product and growth leaders at Airbnb, Stripe, Intercom, Google, Quibi, Duolingo, Ramp, Toast, and more.

How Product Leaders Turn Painful Failures Into Career-Defining Lessons

This compilation episode of Lenny's Podcast assembles candid stories of failure from top product and growth leaders at Airbnb, Stripe, Intercom, Google, Quibi, Duolingo, Ramp, Toast, and more.

Guests describe personal and organizational missteps—from botched redesigns and culture clashes to billion‑dollar product flops—and unpack what actually went wrong beneath the surface.

Across stories, themes emerge around trust, fear‑based strategy, experimentation discipline, unit economics, and the gap between polished ‘A‑side’ narratives and messy ‘B‑side’ realities.

The episode argues that failure, when examined honestly and conclusively, is one of the most powerful drivers of growth for both people and companies.

Key Takeaways

Earn trust before driving change as a new leader.

Katie Dill’s Airbnb story shows that arriving with strong opinions and “coming in swinging” without first listening can trigger team rebellion; slowing down to understand motivations and build trust dramatically improved engagement and outcomes.

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Avoid building products from fear and competition anxiety.

Paul Adams’ experience on Google’s social products (Buzz, Google+) and the intense secrecy and paranoia around them illustrates that initiatives driven primarily by fear of competitors rarely yield great products or healthy cultures.

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Design experiments so failures are conclusive, not ambiguous.

Sri Batchu emphasizes that failed tests are only useful if they decisively validate or kill a hypothesis; in lower-volume B2B contexts that means maximizing treatment effects and throwing multiple tactics at a hypothesis so you can confidently stop repeating dead ideas.

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Respect unit economics and core capabilities before scaling operations-heavy ideas.

Airbnb Plus, as described by JZ, tried to solve trust issues with costly inspections and managed inventory—ignoring Airbnb’s strengths (reviews, lightweight tools) and weak operational muscles—leading to a structurally uneconomic program that likely never penciled out.

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Separate the ‘product story’ from the ‘business equation.’

Tom Conrad’s Quibi reflections highlight that even beautifully executed products can’t redeem a fundamentally broken financial model; if the content/retention equation requires far more capital than is realistic, no amount of iteration will fix it.

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Embrace and share your career’s ‘B-side’ to stay resilient.

Gina Gotthilf’s candid recounting of depression, dropouts, firings, unpaid work, and failed campaigns shows that rocky stretches are common and often precede big breaks; recognizing this helps people see setbacks as chapters, not verdicts.

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Be wary of big rewrites and solution-first product work.

Both JZ’s Airbnb Plus story and Maggie Crowley’s multi-year rewrite disaster underscore how jumping to solutions—especially ‘clean slate’ rewrites—without rigorous discovery, technical diligence, and value analysis tends to produce overruns, sunk-cost traps, and little real upside.

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Notable Quotes

You can inflict change on people, but if you want to do it with them, you really, you know, trust is the key element there.

Katie Dill

The root cause for me is that the project has been run from a place of fear, competitive fear, which I don't think leads to good things.

Paul Adams

For me, failure is not that you didn't drive revenue. Failure is not learning.

Sri Batchu

Companies are also kind of like a math problem… if the equation is fundamentally broken, no amount of iteration and execution can get you out of the failed outputs.

Tom Conrad

We are very encouraged… to talk about our A sides all the time… but between all of those highlights, there were so many B moments.

Gina Gotthilf

Questions Answered in This Episode

How can new leaders practically balance the pressure to ‘make an impact fast’ with the need to build trust and listen first?

This compilation episode of Lenny's Podcast assembles candid stories of failure from top product and growth leaders at Airbnb, Stripe, Intercom, Google, Quibi, Duolingo, Ramp, Toast, and more.

Get the full analysis with uListen AI

What early signals can teams watch for that a strategic initiative is being driven by fear of competitors rather than genuine customer insight?

Guests describe personal and organizational missteps—from botched redesigns and culture clashes to billion‑dollar product flops—and unpack what actually went wrong beneath the surface.

Get the full analysis with uListen AI

In low-volume environments, how should teams decide when an experiment has ‘failed conclusively’ enough to permanently shelve an idea?

Across stories, themes emerge around trust, fear‑based strategy, experimentation discipline, unit economics, and the gap between polished ‘A‑side’ narratives and messy ‘B‑side’ realities.

Get the full analysis with uListen AI

What frameworks can product and finance leaders use together to stress-test whether a compelling product concept is supported by a viable business equation?

The episode argues that failure, when examined honestly and conclusively, is one of the most powerful drivers of growth for both people and companies.

Get the full analysis with uListen AI

How can organizations create safe, structured spaces for sharing ‘B-side’ failures so that learning is normalized rather than stigmatized?

Get the full analysis with uListen AI

Transcript Preview

Lenny Rachitsky

(instrumental music) Today, we've got another very special compilation episode. Something that I've been pulling on more and more with the podcast and the newsletter, in case you've noticed, is failure. Normally, I spend a lot of time researching how the best companies and the best product leaders operate, but you can learn a lot, and often a lot more, from failure. And so what we've done with this episode is we've looked at all of the past episodes we've done and pulled out all the most interesting and insightful stories of failure, and turned it into this very focused episode on failure. I hope that you find this useful and interesting. Let us know what you think in the comments on YouTube or on LennysNewsletter.com, or just let me know on Twitter. If you like this, we'll keep doing this. If not, we'll probably not. Either way, I hope you enjoy. Before we dive in, here is a short word from our wonderful sponsors. (instrumental music) Let me tell you about our product called Sendbird, the all-in-one communications API platform designed for both web and mobile apps. In a world saturated with multi-channel communication, product teams are discovering the effectiveness of in-app communication. With Sendbird, businesses can elevate their in-app experience with decluttered and branded communication featuring AI-powered chatbots, one-way messages, chat, video calls, and live stream capabilities, all tailored for commerce, marketing, and top-tier support. Forward-thinking companies such as Hinge, Patreon, Yahoo, Accolade, and more use Sendbird to build in-app communication experiences that drive engagement, conversion, and retention. In-app communication has the highest conversion, highest engagement, and highest satisfaction of any communication channel. And when it comes to investing in this channel, trust Sendbird to take your in-app communication experience to the next level. Start today with Sendbird's free plan, and as a listener of Lenny's podcast, you'll get an additional two months of unlimited usage and access to all premium features, including creating your very own generative AI chatbot. Visit sendbird.com/lenny to begin your free journey. That's sendbird.com/lenny. This episode is brought to you by Eppo. Eppo is a next generation A/B testing and feature management platform built by alums at Airbnb and Snowflake for modern growth teams. Companies like Twitch, Miro, ClickUp, and DraftKings rely on Eppo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features, and Eppo helps you increase experimentation velocity while unlocking rigorous deep analysis in a way that no other commercial tool does. When I was at Airbnb, one of the things that I loved most was our experimentation platform, where I could set up experiments easily, troubleshoot issues, and analyze performance all on my own. Eppo does all that and more with advanced statistical methods that can help you shave weeks off experiment time, an accessible UI for diving deeper into performance, and out-of-the-box reporting that helps you avoid annoying prolonged analytic cycles. Eppo also makes it easy for you to share experiment insights with your team, sparking new ideas for the A/B testing flywheel. Eppo powers experimentation across every use case, including product, growth, machine learning, monetization, and email marketing. Check out Eppo at geteppo.com/lenny and 10X your experiment velocity. That's geteppo.com/lenny. All righty. First up, we've got Katie Dill, who is head of design at Stripe and former head of design at Airbnb and Lyft, sharing this amazing story of how the entire design team at Airbnb basically rebelled against her soon after she joined, and what she learned from that experience.

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