Chip Conley
Chip Conley talks about blind spots at Airbnb: "I said to Brian, 'I've seen the business plan and the goals for how big we want to be in three years. But what we're really trying to do is have no regu...
Read more →Lenny's Podcast Wisdom
Lenny's Podcast features in-depth conversations with founders, product leaders, and operators. Lenny Rachitsky made all 303 transcripts publicly available—I downloaded them and used AI to analyze them for insights that become more valuable with experience.
These are tips that resonate differently when you've lived through multiple business cycles, technology shifts, and organizational transformations.
Featured: The Modern Elder
Chip Conley's insights on leveraging decades of experience in fast-moving organizations
Chip Conley
Chip Conley talks about brain science and collaboration: "A younger brain has fluid intelligence—tends to be fast and focused, really good at problem solving, very good at linearity in terms of lookin...
Read more →Chip Conley
Chip Conley talks about product decisions at Airbnb: "The two sharing economy darlings were Uber and Airbnb. Uber was pretty much a mobile-only app. Airbnb started as non-mobile then went mobile. Then...
Read more →Ada Chen Rekhi
Ada Chen Rekhi talks about Curiosity Loops—sending a focused question to 5-10 people and triangulating their perspectives. She used it prepping for Lenny's podcast: sent 9 topics to 10 contacts, asked...
Read more →Ada Chen Rekhi
Ada Chen Rekhi uses the boiling frog metaphor for career inertia. Drop a frog in boiling water, it jumps out. Put it in cold water and slowly turn up the heat? The frog doesn't notice the change degre...
Read more →Ada Chen Rekhi
Ada Chen Rekhi had been coaching a seed-stage founder on Zoom for months—brilliant operator, sharp strategic thinking. When they met for lunch in person, the founder showed up dressed like a weekend h...
Read more →Alex Komoroske
Alex Komoroske talks about the builder vs gardener mindset. Builders have a plan, manipulate things to match that plan, force outcomes. Gardeners direct growth, add energy where needed, curate what em...
Read more →Ami Vora
Ami Vora talks about choosing jobs: "I try to work through the spreadsheets and then tear it up. The thing that has determined where I do my best work is a feeling of being at home. When I walk throug...
Read more →Andrew Wilkinson
Andrew Wilkinson talks about his biggest mistakes in business: "The biggest mistakes I've made have been going into business models where other people have repeatedly failed and thinking, I can do thi...
Read more →Archie Abrams
Archie Abrams talks about long-term experiment results at Shopify: "I think it's in the 30 to 40% range. 30 to 40% of experiments that show short-term lift show no long-term lift when we look back a y...
Read more →Archie Abrams
Archie Abrams talks about metric traps at Shopify: "When you have teams naturally break up the world into different funnel stages, it gets very seductive to look at my part of the funnel and what's my...
Read more →Ayo Omojola
Ayo Omojola talks about Cash App differentiation: "Being different is not enough, because it's very easy to build a thing that's different from what exists today, because you just have to look at what...
Read more →Bangaly Kaba
Bangaly Kaba talks about the identify-justify-execute anti-pattern: "We've all had a moment where we worked on something with a team, super excited, finally it launches, we celebrate. We go back the n...
Read more →Bangaly Kaba
Bangaly Kaba talks about Instagram's connections pivot in 2017: "Early Instagram was built where every follow was created equal. If I followed you or Kim Kardashian, all follows were treated equally i...
Read more →Barbra Gago
Barbra Gago talks about Greenhouse's failed category creation attempt: "The ATS or applicant tracking system category at the time carried so much disdain. People had such bad experiences with that who...
Read more →Ben Horowitz
Ben Horowitz talks about hesitation killing companies: "The worst thing you do as a leader is you hesitate. The thing that causes you to hesitate is both decisions are horrible." His example: going pu...
Read more →Bob Baxley
Bob Baxley talks about his stint at Pinterest: "I bounced off the culture. My friend said 'I thought of it as you bounced off the culture.'" He continues: "These careers are really hard. People think ...
Read more →Brandon Chu
Brandon Chu talks about prioritizing decisions as a PM: focus relentlessly on the few truly critical decisions, and trust your gut on everything else. But here's the insight he adds: "Once you've had ...
Read more →Bret Taylor
Bret Taylor talks about getting advice: "Don't just ask what to do but why. Be an obnoxious two-year-old kid, why? Why? Why? Really try to understand the framework that someone is using to give you ad...
Read more →Brian Balfour
Brian Balfour talks about platform cycles: "I lived the full cycle in a very short period. I lived the glory days and just the absolute horror days" with Facebook's platform. He's watched it repeat wi...
Read more →Brian Chesky
Brian Chesky talks about how founders waste time reacting: "A lot of founders spend their time based on reacting. So people will email them and they'll wake up and they'll respond to emails, and sudde...
Read more →Brian Tolkin
Brian Tolkin talks about launching uberPOOL in China: "I've slept on the floor in China before launching uberPOOL, and when you reflect the stress onto your teams, everybody tenses out. It counterintu...
Read more →Cameron Adams
Cameron Adams talks about building Canva's MVP: "When we were building, the Lean Startup book came out, so that was all anyone talked to us about. Investors, other people building products, trying to ...
Read more →Camille Fournier
Camille Fournier talks about system rewrites: "I have seen so many instances of cases where the engineers have convinced themselves that the only solution to the woes that they're experiencing with th...
Read more →Camille Ricketts
Camille Ricketts talks about building Notion's community: "One of my number one recommendations for anybody who suspects the community could be a big growth driver is to not make metrics the be all en...
Read more →Carilu Dietrich
Carilu Dietrich talks about spending hundreds of millions on advertising at Oracle and Atlassian: "Oracle spent a ton of money, and people still didn't like us because they had poor experiences with t...
Read more →Carilu Dietrich
Carilu Dietrich talks about picking companies: "I spent the next five years trying to figure out, how do you pick your next Atlassian?" She keeps a Post-it note with her 10-point framework: Rule of 40...
Read more →Carole Robin
Carole Robin talks about mental models: "One of the biggest gifts people get is learning that they hold some mental models, beliefs and assumptions—'if I do this, that will happen.' Those are beliefs ...
Read more →Casey Winters
Casey Winters talks about data network effects: "Leveraging product usage data to make the product value stronger and stronger over time. Especially with Facebook and Apple's platform changes, your pr...
Read more →Casey Winters
Casey Winters talks about product-led sales: "You can unify self-service loops in a B2B business, which are typically driven by product and your sales loops into one more complex giant loop that opera...
Read more →Casey Winters
Casey Winters talks about founder bottlenecks: "When I was at Grubhub, we acquired a competitor. Even though they were largely in the same phase as us, they still operated like they were founding the ...
Read more →Casey Winters
Casey Winters talks about Grubhub versus DoorDash: "What I've learned now that I'm more senior in my career is during existential threats, it's like when Nassim Taleb says, 'The only rational reaction...
Read more →Casey Winters
Casey Winters talks about consumer subscription businesses: "You need higher user-based retention than B2B SaaS businesses with more unpredictable users. We're talking annual retention that needs to b...
Read more →Chandra Janakiraman
Chandra Janakiraman talks about strategy work: "Whether it's big S or small S, these are incredibly satisfying processes to go through in the end. But they have a ton of challenge, frustration, and de...
Read more →Chip Huyen
Chip Huyen talks about system thinking in debugging: "I was using AI to deploy an application and it kept getting a bug, so I asked AI to fix it. And it kept changing things—maybe change the environme...
Read more →Christian Idiodi
Christian Idiodi talks about promotions: "Most people are promoted to a point of incompetency... Lenny is a fantastic engineer, he wins engineer of the year awards, everybody knows him. The next role ...
Read more →Christina Wodtke
Christina Wodtke talks about product sense: "Product sense is intuition, intuition is compressed experience, compressed experience comes from having lots of experience. And if you're young and you don...
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