David Singleton
Co-founder & CEO, Dreamer. On 2 shows, 2 appearances. The Shows tab opens the full record on each.
founderexecutiveengineer@dps ↗LinkedIn ↗blog.singleton.io ↗
David Singleton served as Chief Technology Officer at Stripe from 2017 to 2024, following a decade at Google as VP of Engineering. In 2024, he co-founded Dreamer, an AI platform designed for creating and operating personal AI agents.
2shows
2appearances
47statements
5resolved
4supported
1contradicted
80%fully supported
11said about them ↓ Everything David Singleton said on any show that made the record, most notable first. Each card names its show and opens the statement there.
Singleton: Stripe deployed some of the world's first production AI agent systems
“I was working at Stripe, as you mentioned, and we had the opportunity to put some of the very first AI agent systems in the world into production.”
Singleton: TypeScript is the optimal language for AI-driven development
“TypeScript is an amazing language for AI because there's tons of training data. In the models and it's strongly typed. 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 th…”
Singleton: Dreamer replaced Vector DB RAG for agent memory due to complexity
“Very early on, we were putting lots of facts into a vector database and doing embeddings and pulling them back out using, you know, reverse look of embeddings. Rag that actually worked, but turned out to be much more complexity than was actually required. So, …”
Singleton: Hands-on engineering managers have the ideal skill profile for AI orchestration
“It turns out being an engineering manager, as long as you stay very close to the code and are able to continue to craft it yourself, is actually a great skill profile for being able to make agents work for you and for your team in this in this age.”
Dreamer pays AI tool builders proportionally based on agent usage
“And we're actually sharing something for the first time on this podcast, which is tool builders on Dreamer get paid. So if you publish a tool to the platform and a lot of agents use it, you'll actually get paid in proportion to their usage.”
Singleton: Standalone AI apps cannot scale safely without an OS-like core
“Because if you try to pick off just one piece of this, you can't actually make it work for people at scale because you could build little vibe coded apps, but they're going to grab all your data willy nilly. They won't be able to work together. You actually ha…”
Singleton: Developers must optimize their CLIs for AI agent discovery
“I was chatting with folks at Stripe last week and saying, hey, you got to make the Stripe CLI actually tell agents what they can do on Stripe because that way they're going to use more stuff on Stripe. I think this is a real trend for the entire industry.”
Singleton: Orchestrating concurrent coding agents in a round-robin pipeline multiplies productivity
“Anytime I'm working on code these days, I always have more than one agent going at the same time, because while one agent is going and reviewing the output of the next one, and if you get them in a nice round robin, you can be very, very productive. You can al…”
Migrating to Stripe Checkout increases average customer revenue by 10.5 percent
“What we've found, we've recently measured the difference between, so with a bunch of actual users who've migrated from a fairly vanilla integration where they, you know, built their own checkout flow to one of these surfaces to our payment element or to Stripe…”
Stripe automatically deploys engineer code changes to production within 45 minutes
“Every change that Stripe engineer submits once it's passed those tests, it actually ends up in production automatically over the course of the next 45 minutes or so.”
High GPU compute costs force AI startups to monetize from day one
“One big difference between AI startups and others is it's actually quite expensive to operate an AI startup in terms of the compute resources, like running this stuff in these GPU machines is quite expensive. So typically these companies need to have a monetiz…”
Midjourney's Discord interface brilliantly teaches users how to prompt AI from others
“This is not the right interface for this tool, but actually it's very smart because you learn from other people on discord, how they're prompting the AI in order to get the kind of results that they're looking for.”
Dreamer targets non-technical consumers for building and using AI agents
“Dreamer is a new product which everyone can come and play with today. It's a place where everyone, literally everyone, can discover, build, and enjoy and use AI agents and agentic apps. And we really did design it for consumers, for folks who are not necessari…”
Singleton: AI agents work best when integrated into users' existing apps
“We've actually find that making things show up in the other apps that you already use in your life is incredibly powerful.”
Singleton built an AI Engineer Conference schedule app in 25 minutes
“And I was able to build this yesterday morning. I did it between some meetings. I think I spent a total of 25 minutes of wall clock time on it. I did it over the course of a couple of hours.”
Self-testing feedback loops unlock the magic of state-of-the-art coding models
“Anytime you can get any modern state-of-the-art coding model into a loop where it can make changes and perceive its own output and then fix bugs, magic happens.”
Dreamer uses autonomous AI agents to research and screen waitlist signups
“So at this point, we pretty much run the company on Dreamer agents for all kinds of important things. Maybe a good example of that is our wait list. People are signing up. Every time someone signs up for our waitlist, a Dreamer agent will actually research tha…”
Singleton predicts one or two dominant agentic commerce protocols will emerge
“You know, on Dreamer, we hope that folks will build tools that can make use of all of these things, but I'm sure that at a certain .1 or two will emerge as the winners, and then we'll be able to build, like, really deep support in it.”
Singleton primarily evaluates engineering candidates on their ability to use coding agents
“One of the main things that I look for now when hiring engineers is how well do you work with coding agents?”
Singleton: LLMs lack out-of-the-box taste, creativity, and a sense of individuality
“Taste, creativity, sense of individuality is still something that I think that the LLMs are not producing out of the box. And I think that's going to be an interesting frontier.”
Singleton: Stripe engineering interviews permit Google and Stack Overflow searches
“The other thing that all these loops have in common is nothing is a trick question. Like we try to put people into an environment, which is as close to doing the actual work together as we possibly can. So I mean, for engineers, for instance, we've got several…”
Singleton: Best PMs for Developer Products Are Highly Technical Engineers
“The best PMs for developer focused products, I think are usually very technical. They're mostly former engineers themselves, or maybe kind of current engineers still tinkering on the side, but bringing, you know, a lot of user insight and strategy to the probl…”
Stripe's API dedicates more codebase to edge cases than main flows
“There's actually more code in the jobs that serve the Stripe API to handle those edge cases than in the actual main flow.”
The other half of the tape: David Singleton's own voice is left out of every number here. Other people bring the name up 9 times in 2 episodes across the shows. 2 statements on the record name them. every mention, with the transcript →
Who brings them up most Lenny Rachitsky 6Shishir Mehrotra 2Katie Dill 1
Statements about David Singleton, by other people (2)
Stripe credits its 99.999 percent reliability to random 'Spin the Wheel' reviews
“When I asked him about the rituals there, he said, well, the secret to why Stripe has five nines of reliability is a ritual they call Spin the Wheel. And it started with a operational reviews, where they used to come in, and they would look at all the outages …”
Stripe's Design Head and CTO regularly test random product flows together
“David Singleton, who you mentioned, he and I do these things very regularly too. Like this is like kind of outside the essential journeys program, but like he and I walk the store and we'll just pick random flows and go through it together. And, you know, I ca…”
Every mention by year
tap a year for its mentions
Lenny's Podcast 9
2024 2 mentions in 1 episode
One line per show, most statements first. The link opens David's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
| LENNY'S PODCASTLEDGER | Co-founder & CEO, Dreamer | 1 | 26 | 80% 4/5 | full record on Lenny's Podcast → |
 LATENT SPACELEDGER | Co-founder & CEO, Dreamer | 1 | 21 | — | full record on Latent Space → |