David Singleton
About David Singleton
David Singleton was CTO of Stripe from 2018 to 2024, according to a CloudCruise investor's account on LinkedIn. Crunchbase also lists him as Stripe CTO and places him in San Francisco.
In 2024 he started Dreamer, which is described as a home for agentic apps. Kyber Knight Capital was an early seed investor. Fortune later described him as the Dreamer cofounder who sold his company to Meta. His LinkedIn headline lists Meta Superintelligence Labs at Meta.
Crunchbase lists eight personal investments for Singleton, with Eigen as the most recent. Dollar amounts and dates are hidden in the public view of that profile. The rounds confirmed from company and press announcements are all 2026 seed rounds in AI companies.
He is usually named as an angel alongside a lead fund, not as the lead. Public coverage does not state his check sizes or any investing criteria.
Eigen (April 2026): $15M seed led by Benchmark, with Pinterest cofounder Ben Silbermann also joining as an angel. Eigen is building a "mutual friend" AI for shared, real-world experiences, and Fortune reported the round.
BottleCap AI (January 2026): $7.5M seed led by 20VC. The Prague-based company is working on more efficient foundation models and was founded by Google and Meta alumni. Other named angels include Canva cofounder Cliff Obrecht and Xavier Niel.
CloudCruise (March 2026): $5M seed backed by Floating Point, Meridian Street Capital, Twine, Refract Ventures and angels including Abridge CTO Zachary Lipton. CloudCruise builds coding, infrastructure and maintenance agents for browser automation, with a focus on healthcare portals and EHRs.
The confirmed deals are seed-stage rounds in AI: consumer AI (Eigen), foundation model efficiency (BottleCap AI) and agent-based automation for healthcare (CloudCruise). His background is in infrastructure and developer-facing products at Stripe, and in agentic software at Dreamer. Two of the three companies are founded by teams with Google, Meta or other large-company engineering backgrounds. Geography is mixed: Eigen is US-based, BottleCap AI is in Prague. No check size or stated thesis is public.
- Eigen: AI "mutual friend" product for shared experiences; $15M seed led by Benchmark, April 2026.
- BottleCap AI: efficiency-focused foundation models; $7.5M seed led by 20VC, January 2026.
- CloudCruise: browser automation agents for healthcare workflows; $5M seed, March 2026.
- fortune.com/2026/04/16/exclusive-eigen-seed-round-benchmark-capital-be
- app.dealroom.co/news/feed/eigen-raises-15m-to-build-mutual-friend-ai-f
- app.dealroom.co/news/feed/google-and-meta-alumni-raise-7-5m-to-build-1
- cloudcruise.com/blog/seed-round
- linkedin.com/in/davidpsingleton
- crunchbase.com/person/david-singleton-e328
Investing activity
David Singleton appears in 3 AI deals tracked by the Lounge deals desk, rounds totalling $15M. The rounds are mostly Seed, with a median round size of $8M and the largest at $15M. The most recent are Eigen (Seed, $15M, Apr 2026), CloudCruise (Seed, $5M, Mar 2026) and BottleCap AI (Seed, $7.5M, Jan 2026).
David Singleton most often invests alongside Benchmark, Peter Sellis, Terrence Rohan and K5 Global, and the companies they back on Lounge are mostly in AI.
Deals
Frequently asked questions about David Singleton
Who is David Singleton, the angel investor?
He is a former CTO of Stripe (2018 to 2024) and the cofounder of Dreamer, which was later sold to Meta. He now angel-invests in AI startups.
What AI startups has David Singleton invested in?
Publicly confirmed 2026 seed rounds include Eigen ($15M), BottleCap AI ($7.5M) and CloudCruise ($5M). Crunchbase lists eight personal investments in total.
What is David Singleton's angel check size?
It is not public. Neither the funding announcements nor his profiles state how much he invests.
Does David Singleton lead rounds or follow?
In the announcements found, he joined rounds led by others: Benchmark for Eigen and 20VC for BottleCap AI. He is listed as an angel in each.
What stage does David Singleton invest in?
The confirmed AI deals are all seed rounds. Crunchbase also lists his investor stage as Seed.
Where can founders find David Singleton online?
He has a LinkedIn profile. No personal site or X account was confirmed in the sources reviewed.
Is David Singleton an angel investor?
Yes. David Singleton invests personally as an angel.
What AI companies has David Singleton invested in?
David Singleton's AI investments include Eigen, CloudCruise and BottleCap AI. The 3 rounds on Lounge are listed on this page with amounts, dates and co-investors.
What stage does David Singleton invest at?
In the rounds tracked on Lounge, David Singleton has invested at Seed, with a median round of $8M.
Who does David Singleton co-invest with?
David Singleton's most frequent co-investors on Lounge are Benchmark (1 deal), Peter Sellis (1 deal), Terrence Rohan (1 deal), K5 Global (1 deal) and Akshay Kothari (1 deal).