❝Story03:30
Katie Dill: When the Airbnb Design Team Rebelled Against Her
Katie Dill (head of design at Stripe, formerly Airbnb and Lyft) recounts how, about a month into leading Airbnb's 10-person design org, half the team plus HR gathered to read her a list of everything she was doing wrong. The core lesson was that she hadn't earned their trust before pushing change. She shifted from 'coming in swinging' to listening first, and a couple months later the team had the best engagement scores in the company.
- She joined 'ready to go' and started driving change before building trust with the existing team.
- Five team members and an HR partner took turns reading criticisms of her aloud from prepared papers.
- The unifying theme was that she hadn't earned their trust, so nobody believed in what she was building.
- You can inflict change on people, but doing it with them requires trust.
- After shifting to a listen-first approach, the team hit the best engagement scores in the company.
“the theme that was across all of that is that I hadn't earned their trust”
“instead of coming in swinging you know come in listening so that you can really you know set out to make change”
#leadership#design#trust#management
❝Story08:00
Paul Adams: Freezing on Stage at Cannes in Front of Thousands
Paul Adams (CPO at Intercom) describes representing Facebook on the keynote stage at Cannes, the world's biggest advertising festival, and having a panic attack three or four minutes in. He walked off stage still miked up, cursed, then recovered and finished the talk. His takeaway is that even living out the worst public-speaking nightmare turns out to not be a big deal.
- It was the first time he'd ever rehearsed a talk word-for-word, media-trained not to say the wrong thing.
- He froze, couldn't remember his lines, had a panic attack, and walked off stage.
- His mic was still on, so the audience heard him curse, then he walked back out and finished well.
- He was 'famous and infamous' in Cannes that night for the performance.
- The lesson: adapt to curveballs; none of these things are as big a deal as they feel in the moment.
“I just froze I I couldn't remember what I was supposed to say”
“none of these things are that big a deal at the end of the day you know you kind of move on live and learn”
#public-speaking#resilience#failure
❝Story11:30
Paul Adams: Why Google's Social Products (Buzz, Plus) Failed
Paul Adams reflects on working on failed Google social projects like Google Buzz and Google+, arguing they came from a place of competitive fear rather than genuine user need. His own research mapping dozens of people's social networks revealed people needed better ways to talk to small groups of family and friends, an insight obvious in hindsight (WhatsApp, iMessage) but missed at the time.
- Google Buzz and Google+ were motivated by competitive fear, not by understanding user problems.
- His formative research with dozens of people over ~18 months surfaced the same pattern every time: people need better small-group communication.
- Google+ secrecy was extreme: a separate building with a different key card for people not on the project.
- Leaving mid-project to join Facebook got him quarantined and his laptop forensically analyzed as a suspected spy.
- Projects run from a place of competitive fear don't lead to good products.
“I think a lot of the motivation for those projects came from a place of fear”
“the project has been run from a place of fear competitive fear which I don't think leads to good things”
#product#google#strategy#fear
❝Story19:30
Tom Conrad: How Too Much Money Sank Pets.com
Tom Conrad (CPO at Quibi, engineering leader at Pets.com) shares that three overfunded pet e-commerce sites each raised ~$50M and, treating it as a zero-sum game, spiraled into an unwinnable advertising arms race. He notes an excess of investment can become its own liability, and that timing mattered enormously (Chewy later succeeded when the same model was viable).
- Three pet e-commerce sites each raised roughly $50M and outspent each other on national TV advertising.
- An excess of investment can be its own albatross, pushing teams toward unwise decisions.
- The 'shipping dog food is a stupid business' critique was wrong; the problem was 80% of the US was still on dialup.
- Chewy later executed the same model brick-by-brick and became a multi-billion-dollar company.
- Pets.com didn't go bankrupt: the team wound down early and returned the remaining cash to investors, which no public company had done before.
“it became this kind of unwinable arms race”
“we actually didn't go bankrupt we shut the company down and returned the the remaining balance to the investors”
#startups#funding#e-commerce#timing
❝Story23:00
Tom Conrad: Quibi's Math Was Broken Before COVID Hit
Tom Conrad argues Quibi failed not on execution but on a fundamentally broken equation: you can't build a bespoke content library big enough to drive subscriptions and retention for only a couple billion dollars. COVID compounded it, forcing the premium daily content meant to differentiate Quibi from YouTube to be shot in hosts' garages, exactly like YouTube.
- Companies are like a math problem turning investment into returns; a broken equation can't be fixed by iteration or execution.
- Quibi made 70 shows in 18 months, more than all major broadcast networks combined make in a year.
- About a third to half of content spend went to daily content designed to be shot day-of in professional studios.
- Launching two weeks into COVID forced that content into hosts' garages, making it look exactly like YouTube.
- The real bet needed six to ten billion dollars, not two; that risk-reward was more than anyone could stomach.
“no amount of like iteration and execution can like kind of get you out of the the failed outputs of the broken equation”
“we launched two weeks into covid and we couldn't make any of that content except literally in the garages of the host homes”
#startups#product#media#unit-economics
❝Story40:30
Jiaona Zhang: Why Airbnb Plus Was Doomed by Unit Economics
Jiaona Zhang tells the untold story of Airbnb Plus, where the team went solution-first (inspecting and managing inventory) out of competitor fear, rather than solving the real problem: people not knowing what they were getting into. She argues the unit economics never would have worked, and cheaper, on-brand fixes like reviews, lockboxes, or cleaner partnerships targeted the actual problems better than inspectors.
- Airbnb Plus was solution-first and competitor-afraid, reacting to managed marketplaces.
- The real problem was that people want to know what they're getting into and homes needed better representation.
- Airbnb's strategic weakness was operations; building inspection from the ground up wasn't in its wheelhouse.
- 'Magical thinking' about unit economics assumes it all works out at scale instead of validating it early.
- Cheaper, on-platform solutions (guest reviews, lockboxes, cleaner partnerships) beat sending physical inspectors.
“we essentially were like let's go inspect our inventory let's actually try to manage our inventory more”
“I personally don't believe the unit economics ever would have really worked out”
#product#airbnb#unit-economics#strategy
❝Story52:30
Gina Gotthilf: The Duolingo Badges Miss and Forgetting to Dogfood
Gina Gotthilf recounts delaying a Duolingo badges experiment for six months on ROI grounds, then running a lean version that failed because no one is proud of just signing up. The deeper embarrassment was that the growth team wasn't dogfooding; had they tested it themselves they'd have known the badge was lame. Once done right, badges impacted almost every company metric.
- She blocked the badges experiment for ~six months to focus on lower-hanging fruit, a mistake on her end.
- The lean MVP awarded a badge just for signing up, which produced no results because signup isn't an exciting, shareable moment.
- The growth team hadn't been dogfooding, so they never caught how weak the badge was.
- Dogfooding became a permanent team practice after this.
- Done properly, badges lifted nearly all company metrics and unlocked a treasure trove of engagement asks.
“we hadn't been dog fooding in the growth team”
“why are we not testing our experiments”
#growth#duolingo#experimentation#dogfooding
❝Story58:00
Maggie Crowley: 'What's the Worst Product You Ever Shipped?'
Maggie Crowley (VP of product at Toast) shares her favorite interview question, what's the worst product you ever shipped, arguing a PM who can't name a truly bad one hasn't done enough or can't admit it. She then tells her own worst project: a side-by-side rewrite estimated at six months that took two and a half years and never reached parity, with the flat lesson to never do a rewrite.
- She asks every PM candidate what's the worst product they ever shipped, and admitting it is as important as having done it.
- Her worst project was a rewrite of an existing product estimated at six months that ran two and a half years without reaching feature parity.
- Root causes: arrogance, skipping discovery, no one-pager, and insufficient technical and design research into requirements.
- The project didn't change the business trajectory, but she didn't get fired.
- Her blunt advice: don't do a side-by-side rewrite; once teams build in the new world and the launch goes negative, you're stuck clawing back to neutral.
“a question I ask in every product interview is uh what's the worst product you ever shipped”
“don't rewrite if anyone ever tells you to do a rewrite don't do it a side bys side rewrite nope”
#product#hiring#rewrites#engineering