High Signal Podcasts Evidence ledger
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Public evidence record

David Singleton

Published podcast speaker

Claims
26
Episodes
2
Shows
2
Named items
5

Books, apps, and tools

The evidenced stack.

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app / likes

Dreamer

“Um, let’s look at something that hopefully is kind of near and dear to your heart. So one of the things I love about Dreamer and this kind of moment in technology is that if you think about it.”

Latent Space · 20 Mar 2026

Evidence receipt · Source ↗

service / likes

Latent space

“So, uh, if you go to dreamer.com/latent space, you’ll find, ooh, well, we love Latent space.”

Latent Space · 20 Mar 2026

Evidence receipt · Source ↗

book / recommends

Skilling People

“Most means that you have to integrate under the curve, so I'd say High Output Management by Andy Grove is definitely the book that I've recommended the most. It was a book that really opened my eyes to how to get the most out of teams over the whole course of my career. Definitely check that out if you haven't read it already. Recently, we talked about being meticulous in our craft. I've really enjoyed Build by Tony Fidel. Tony worked on the iPod, and then the iPhone, and then was the founder of Nest. He puts a tremendous amount of thought into his users and how to build really great crafted experiences. I had the privilege of working with him very briefly at Google, but I thought the book was excellent in terms of helping provide some practical pointers there. Then I would be remiss if I did not mention Claire Hughes Johnson's book, Skilling People. Even though it only just came out, I've recommended it a lot. There's actually some stuff in here where I'm sharing some techniques that we've used at Stripe, so you might enjoy that. Then if I may share one ...”

Lenny's Podcast · 4 May 2023

Evidence receipt · Source ↗

book / recommends

High Output Management

“Most means that you have to integrate under the curve, so I'd say High Output Management by Andy Grove is definitely the book that I've recommended the most. It was a book that really opened my eyes to how to get the most out of teams over the whole course of my career. Definitely check that out if you haven't read it already. Recently, we talked about being meticulous in our craft. I've really enjoyed Build by Tony Fidel. Tony worked on the iPod, and then the iPhone, and then was the founder of Nest. He puts a tremendous amount of thought into his users and how to build really great crafted experiences. I had the privilege of working with him very briefly at Google, but I thought the book was excellent in terms of helping provide some practical pointers there. Then I would be remiss if I did not mention Claire Hughes Johnson's book, Skilling People. Even though it only just came out, I've recommended it a lot. There's actually some stuff in here where I'm sharing some techniques that we've used at Stripe, so you might enjoy that. Then if I may share one ...”

Lenny's Podcast · 4 May 2023

Evidence receipt · Source ↗

book / recommends

Build

“Most means that you have to integrate under the curve, so I'd say High Output Management by Andy Grove is definitely the book that I've recommended the most. It was a book that really opened my eyes to how to get the most out of teams over the whole course of my career. Definitely check that out if you haven't read it already. Recently, we talked about being meticulous in our craft. I've really enjoyed Build by Tony Fidel. Tony worked on the iPod, and then the iPhone, and then was the founder of Nest. He puts a tremendous amount of thought into his users and how to build really great crafted experiences. I had the privilege of working with him very briefly at Google, but I thought the book was excellent in terms of helping provide some practical pointers there. Then I would be remiss if I did not mention Claire Hughes Johnson's book, Skilling People. Even though it only just came out, I've recommended it a lot. There's actually some stuff in here where I'm sharing some techniques that we've used at Stripe, so you might enjoy that. Then if I may share one ...”

Lenny's Podcast · 4 May 2023

Evidence receipt · Source ↗

Claim ledger

What David said.

26 transcript-backed records

04 / belief

For instance, a lot of agents in the platform, when you start using them, the first thing that they’ll show you, here’s what I think is relevant to you for this particular use case.

“For instance, a lot of agents in the platform, when you start using them, the first thing that they’ll show you, here’s what I think is relevant to you for this particular use case.”
Speaker
David Singleton
Publisher
Latent Space

05 / recommendation

Um, and that’s actually a very powerful abstraction because it turns out that the right way to give a lot of context to agents to use CLIs is to write great documentation.

“Um, and that’s actually a very powerful abstraction because it turns out that the right way to give a lot of context to agents to use CLIs is to write great documentation.”
Speaker
David Singleton
Publisher
Latent Space

06 / evaluation

Um, but TypeScript is an amazing language for AI because there’s tons of training data in the models, um, and it’s strongly tight. And actually at the company we built most of the stack in TypeScript, and we have this amazing property, which is, we have type safety all the way from the database to the front end.

“Um, but TypeScript is an amazing language for AI because there’s tons of training data in the models, um, and it’s strongly tight. And actually at the company we built most of the stack in TypeScript, and we have this amazing property, which is, we have type safety all the way from the database to the front end.”
Speaker
David Singleton
Publisher
Latent Space

07 / evaluation

I honestly think this moment in time is a little bit like the early web. So I personally started coding as a kid and I think I got access to the internet in about 19 95, 19 96.

“I honestly think this moment in time is a little bit like the early web. So I personally started coding as a kid and I think I got access to the internet in about 19 95, 19 96.”
Speaker
David Singleton
Publisher
Latent Space

08 / evaluation

Uh, so built by someone in our community. It’s a really powerful calendar app because for each of my meetings, if it’s with someone I don’t already know, well it’ll actually go off and research it, um, and give me both a history of my interactions with those people and also a bunch of, you know, public useful information to, to get started.

“Uh, so built by someone in our community. It’s a really powerful calendar app because for each of my meetings, if it’s with someone I don’t already know, well it’ll actually go off and research it, um, and give me both a history of my interactions with those people and also a bunch of, you know, public useful information to, to get started.”
Speaker
David Singleton
Publisher
Latent Space

14 / recommendation

Recommends High Output Management. Recommends Build. Recommends Skilling People.

“Most means that you have to integrate under the curve, so I'd say High Output Management by Andy Grove is definitely the book that I've recommended the most. It was a book that really opened my eyes to how to get the most out of teams over the whole course of my career. Definitely check that out if you haven't read it already. Recently, we talked about being meticulous in our craft. I've really enjoyed Build by Tony Fidel. Tony worked on the iPod, and then the iPhone, and then was the founder of Nest. He puts a tremendous amount of thought into his users and how to build really great crafted experiences. I had the privilege of working with him very briefly at Google, but I thought the book was excellent in terms of helping provide some practical pointers there. Then I would be remiss if I did not mention Claire Hughes Johnson's book, Skilling People. Even though it only just came out, I've recommended it a lot. There's actually some stuff in here where I'm sharing some techniques that we've used at Stripe, so you might enjoy that. Then if I may share one ...”
Speaker
David Singleton
Publisher
Lenny's Podcast

17 / evaluation

So another 15 minutes then typically takes about 30 minutes for the systems to automatically deployed in production. That's how we run and think about establishing that tight feedback loop with users, that means you can get feedback from a user in the morning, you can figure out how to address it and you can actually put something back in their hands by the end of the day.

“So another 15 minutes then typically takes about 30 minutes for the systems to automatically deployed in production. That's how we run and think about establishing that tight feedback loop with users, that means you can get feedback from a user in the morning, you can figure out how to address it and you can actually put something back in their hands by the end of the day.”
Speaker
David Singleton
Publisher
Lenny's Podcast

20 / evaluation

We're actually helping power all of their subscriptions and revenue tracking and financial operations around the business. And the point about that is we've been putting very large engineering teams on this stuff for years and that means anyone who wants to build a reconciliation product and a subscriptions business model, if you want to do that yourself, you have to put big engineering teams on them.

“We're actually helping power all of their subscriptions and revenue tracking and financial operations around the business. And the point about that is we've been putting very large engineering teams on this stuff for years and that means anyone who wants to build a reconciliation product and a subscriptions business model, if you want to do that yourself, you have to put big engineering teams on them.”
Speaker
David Singleton
Publisher
Lenny's Podcast

21 / evaluation

I was getting an error message back, but I wasn't stuck for very long because something that the team at Stripe had done was we made the error messages coming out of our API link to the piece of the docs that told you how to solve the problem.

“I was getting an error message back, but I wasn't stuck for very long because something that the team at Stripe had done was we made the error messages coming out of our API link to the piece of the docs that told you how to solve the problem.”
Speaker
David Singleton
Publisher
Lenny's Podcast

22 / preference

We really obsess about reviewing them carefully and identifying not only what would've stopped this thing happening, but how could we prevent this whole class of issues in the future. And as I said earlier, we prioritize working on that stuff ahead of anything else on the roadmap that's because of remember what it is we're trying to do, how important it is and how if we don't do that well, we can't move quickly for our users.

“We really obsess about reviewing them carefully and identifying not only what would've stopped this thing happening, but how could we prevent this whole class of issues in the future. And as I said earlier, we prioritize working on that stuff ahead of anything else on the roadmap that's because of remember what it is we're trying to do, how important it is and how if we don't do that well, we can't move quickly for our users.”
Speaker
David Singleton
Publisher
Lenny's Podcast

23 / preference

It's actually important to have a very clear idea of who is the person I am kind of modeling the friction for right now. So for instance, I might be integrating the Stripe billing API and I might put myself in the shoes of an engineer at, I don't know, let's say Atlassian, which is one of the world's largest SaaS platforms and using actively Stripe billing for automating all the revenue today, I might put myself in the mindset of that person.

“It's actually important to have a very clear idea of who is the person I am kind of modeling the friction for right now. So for instance, I might be integrating the Stripe billing API and I might put myself in the shoes of an engineer at, I don't know, let's say Atlassian, which is one of the world's largest SaaS platforms and using actively Stripe billing for automating all the revenue today, I might put myself in the mindset of that person.”
Speaker
David Singleton
Publisher
Lenny's Podcast

24 / evaluation

By the way, the reason I think that planning, the way we do planning at Stripe doesn't always get the best internal rep is we have grown very rapidly. That means that almost every time we come back around to planning, we actually, and this is kind of a theme at Stripe, we think about a lot of the ways that we work internally from First principles.

“By the way, the reason I think that planning, the way we do planning at Stripe doesn't always get the best internal rep is we have grown very rapidly. That means that almost every time we come back around to planning, we actually, and this is kind of a theme at Stripe, we think about a lot of the ways that we work internally from First principles.”
Speaker
David Singleton
Publisher
Lenny's Podcast

25 / preference

One of the most interesting things that I think I've run into is there are a lot of places that as we scale, we know that it makes a lot of sense to invest in automation and there were a bunch of places in our development process where while we've done that, we were working hard to help each other out and actually saying, hey, please come talk to this other team if you want to use this thing.

“One of the most interesting things that I think I've run into is there are a lot of places that as we scale, we know that it makes a lot of sense to invest in automation and there were a bunch of places in our development process where while we've done that, we were working hard to help each other out and actually saying, hey, please come talk to this other team if you want to use this thing.”
Speaker
David Singleton
Publisher
Lenny's Podcast

26 / commitment

I think as I've been responsible for bigger and bigger teams over time, one of the things that just I repeatedly learn is I personally will not be involved in really any of the decisions that matter and happen.

“I think as I've been responsible for bigger and bigger teams over time, one of the things that just I repeatedly learn is I personally will not be involved in really any of the decisions that matter and happen.”
Speaker
David Singleton
Publisher
Lenny's Podcast
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