Lenny's Written Position
Spending time understanding and reframing user problems with strong constraints is more valuable than jumping to solutions, because good framing naturally narrows the solution space.
Angel investors are usually wrong about which investments will do best; only a third of the biggest winners were rated as high-conviction at the time of investing.
Podcast Moments
“How do you actually solve the puzzle by connecting all the dots together? Just like how I see some of my friends, their kids playing Legos, if you don't really see the full picture, you won't be able to make the Lego as one thing at the end of the day. You have to see the other pieces.”
Inside TikTok: Culture, strategy, monetization, and more | Ray Cao (Global Head of Monetization Product Strategy and Operations) · Ray Cao
“Don't call it strategy, call it an action agenda. Begin to try to identify the one or two key challenges that can actually be addressed and what are we going to do about it? What are the coherent actions we're going to do to take these on?”
Good Strategy, Bad Strategy | Richard Rumelt · Richard Rumelt
“A lot of marketplace management is moving attention and inventory around. Many of the changes that are most consequential create winners and losers. And rolling with those changes is about recognizing whether the winners you've created are more important to your business than the losers you've created in the process.”
Marketplace lessons from Uber, Airbnb, Bumble, and more | Ramesh Johari (Stanford professor, startup advisor) · Ramesh Johari
“So therefore, when we're making a decision thinking about a problem, we're going to start with what's best for the customer and then come backward from there.”
Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards) · Bill Carr
“But it gave us some evidence to go and say, 'Hey, we should try and build this thing.'”
Becoming evidence-guided | Itamar Gilad (Gmail, YouTube, Microsoft) · Itamar Gilad
“Your brain is so accustomed to having a scarcity mindset as opposed to creating alternative options or seeing a different path. Effectively, there's this notion of, 'How might the opposite be true?' The moment I challenged myself and said, 'How might the opposite be true?' my shoulders dropped.”
How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · Paige Costello
“Which is usually a mix of career success, but also meaningfulness and alignment in the work that we're doing with our values.”
How to make better decisions and build a joyful career | Ada Chen Rekhi (Notejoy, LinkedIn, SurveyMonkey) · Ada Chen Rekhi
“If you're not sure who the decision maker is, one, it's probably you. And I'd rather you act that way than not because you're going to slow the whole company down. Follow a process and get it done, and don't forget to actually make a decision. Too many people get stuck and it makes your work terrible. What do we all care about? Progress, impact, momentum. Be a force for positive momentum and it will be actually a real career maker.”
Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe) · Claire Hughes Johnson
“There's a tendency when you've been doing this for a while to assume that the decisions you've made in the past are still the right ones. But the world changes, your users change, and you have to be willing to revisit those assumptions constantly.”
Humanizing product development | Adriel Frederick (Reddit, Lyft, Facebook) · Adriel Frederick
“Economics says, 'Look, people are rational. We make decisions with no emotion. We use lots of computational energy, weigh the pros and cons.' I mean, obviously, that's just not true. It ignores the whole field of psychology.”
Using behavioral science to improve your product | Kristen Berman (Irrational Labs) · Kristen Berman
“When COVID hit and travel went to zero overnight, Brian Chesky made a decision very quickly that we were going to focus on what we could control. We couldn't control the pandemic, but we could control how we treated our hosts, our guests, and our employees.”
Sanchan Saxena (VP of Product at Coinbase) on the inside story of how Airbnb made it through Covid; what he’s learned from Brian Chesky, Brian Armstrong, and Kevin Systrom; much more · Sanchan Saxena
Cutting Room Floor
Guest insights on this topic that Lenny hasn't (yet) written about in his newsletters. Potential material for future posts.
“How do you actually solve the puzzle by connecting all the dots together? Just like how I see some of my friends, their kids playing Legos, if you don't really see the full picture, you won't be able to make the Lego as one thing at the end of the day. You have to see the other pieces.”
Inside TikTok: Culture, strategy, monetization, and more | Ray Cao (Global Head of Monetization Product Strategy and Operations) · Ray Cao
“Don't call it strategy, call it an action agenda. Begin to try to identify the one or two key challenges that can actually be addressed and what are we going to do about it? What are the coherent actions we're going to do to take these on?”
Good Strategy, Bad Strategy | Richard Rumelt · Richard Rumelt
“A lot of marketplace management is moving attention and inventory around. Many of the changes that are most consequential create winners and losers. And rolling with those changes is about recognizing whether the winners you've created are more important to your business than the losers you've created in the process.”
Marketplace lessons from Uber, Airbnb, Bumble, and more | Ramesh Johari (Stanford professor, startup advisor) · Ramesh Johari
“So therefore, when we're making a decision thinking about a problem, we're going to start with what's best for the customer and then come backward from there.”
Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards) · Bill Carr
“But it gave us some evidence to go and say, 'Hey, we should try and build this thing.'”
Becoming evidence-guided | Itamar Gilad (Gmail, YouTube, Microsoft) · Itamar Gilad
“Your brain is so accustomed to having a scarcity mindset as opposed to creating alternative options or seeing a different path. Effectively, there's this notion of, 'How might the opposite be true?' The moment I challenged myself and said, 'How might the opposite be true?' my shoulders dropped.”
How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · Paige Costello
“Which is usually a mix of career success, but also meaningfulness and alignment in the work that we're doing with our values.”
How to make better decisions and build a joyful career | Ada Chen Rekhi (Notejoy, LinkedIn, SurveyMonkey) · Ada Chen Rekhi
“If you're not sure who the decision maker is, one, it's probably you. And I'd rather you act that way than not because you're going to slow the whole company down. Follow a process and get it done, and don't forget to actually make a decision. Too many people get stuck and it makes your work terrible. What do we all care about? Progress, impact, momentum. Be a force for positive momentum and it will be actually a real career maker.”
Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe) · Claire Hughes Johnson
“There's a tendency when you've been doing this for a while to assume that the decisions you've made in the past are still the right ones. But the world changes, your users change, and you have to be willing to revisit those assumptions constantly.”
Humanizing product development | Adriel Frederick (Reddit, Lyft, Facebook) · Adriel Frederick
“Economics says, 'Look, people are rational. We make decisions with no emotion. We use lots of computational energy, weigh the pros and cons.' I mean, obviously, that's just not true. It ignores the whole field of psychology.”
Using behavioral science to improve your product | Kristen Berman (Irrational Labs) · Kristen Berman
“When COVID hit and travel went to zero overnight, Brian Chesky made a decision very quickly that we were going to focus on what we could control. We couldn't control the pandemic, but we could control how we treated our hosts, our guests, and our employees.”
Sanchan Saxena (VP of Product at Coinbase) on the inside story of how Airbnb made it through Covid; what he’s learned from Brian Chesky, Brian Armstrong, and Kevin Systrom; much more · Sanchan Saxena