Dalton Caldwell
Partner and Managing Director @ Y Combinator
San Francisco, United States
Dalton Caldwell is a pre-seed investor at Y Combinator in San Francisco focused on Software and Artificial Intelligence. Dalton Caldwell is the current Managing Director of Y Combinator. He previously worked at App.net as a Founder/CEO. Dalton Caldwell attended Stanford University.
- Total investments:
- 190
- Last investment:
- Lead investor:
- 60%
Last updated:
For AI agents: llms.txt
Industries Dalton Caldwell invests in
Stages Dalton Caldwell invests in
Countries Dalton Caldwell invests in
Round sizes
Round size
- Seed
- $1M–$6M
- Pre-Seed
- $500k–$500k
- Series A
- $5.1M–$20M
Investment Focus
Industry
- Software 26 (14%)
- Artificial Intelligence 26 (14%)
- Financial Services 13 (7%)
- SaaS 11 (6%)
- B2B 9 (5%)
Stage
- Pre-Seed 45 (24%)
- Seed 27 (14%)
- Series A 9 (5%)
- Series B 3 (2%)
Country
- United States 67 (35%)
- Brazil 2 (1%)
- France 1 (1%)
- Germany 1 (1%)
- Vietnam 1 (1%)
Investments
| Company | Description | Round | Links |
|---|---|---|---|
Weave
|
Weave resloves engineering tasks by merging large language models with targeted machine learning. | $13.5M / Series A / Jul 28, 2026 | |
Casco
|
Autonomous security testing for web apps, APIs, infrastructure, and AI systems. | $13M / Series A / Jul 16, 2026 | |
Agave
|
Agave develops financial operations software for construction contractors that connects project management and enterprise resource planning (ERP) systems. Its platform automates accounting workflows, including invoice processing, expense management, and financial data synchronization, and uses AI to reduce manual data entry and improve accuracy.Agave also provides real-time financial visibility by integrating project, field, and accounting information across construction systems. The platform supports a range of construction accounting and ERP applications to help contractors manage financial operations more efficiently. | $15M / Series A / Jul 07, 2026 | |
Crimson
|
Crimson is a AI productivity platform that allows litigation lawyers to answer case specific questions. | $2.5M / Seed / May 28, 2026 | |
Voker
|
Voker is the Agent Analytics Platform for monitoring and improving your AI agents. Companies like Dutch.com use our SDK to build better AI. Alex and Tyler met at a high-growth E-Commerce startup where Tyler was running Technology & Data. Together, they built AI products that bootstrapped the company profitably to $100MM in Revenue. | $2.2M / Pre-Seed / May 19, 2026 | |
Avoca
|
Avoca creates a client communication platform that enables business owners to concentrate on their core skills. | $125M / Series B / Apr 27, 2026 | |
Insight Health
|
Insight Health provides an AI-driven platform for healthcare that automates common clinical tasks using various specialized AI agents. The platform features AI agents for patient pre-visit intake and follow-ups, AI-based referral processing, phone triage, appointment scheduling, chart preparation, and clinical documentation capture. This enableshealthcare providers to reduce their administrative workload and focus more on direct patient care. | $11M / Series A / Apr 03, 2026 | |
PointOne
|
PointOne Technologies is a software company that develops AI business software that streamlines legal billing and timekeeping procedures. | $16M / Series A / Mar 23, 2026 | |
Risotto
|
Risotto uses artificial intelligence to resolve IT help inquiries automatically. | $10M / Seed / Jan 27, 2026 | |
Porter
|
Porter is the easiest way to deploy and scale your applications on AWS, Azure, and GCP. Connect your own cloud account, and Porter will provision and manage the underlying infrastructure for you - simply point at your repository and Porter will handle the rest, from building your application to autoscaling it.Under the hood, Porter manages thesame kind of infrastructure that growth-stage companies use and allows you to scale without DevOps overhead. | $20M / Series A / Jan 27, 2026 | |
| See all 190 investments → | |||
Co-Investors
About Y Combinator
Y Combinator is a startup accelerator that provides funding and mentorship to early-stage companies. It offers a program where startups receive guidance from experienced entrepreneurs and investors. The organization helps founders in their business models and develop their products. Y Combinator serves industries such as technology, healthcare, andfinance.
Y Combinator Contacts
| Name | Phone | Socials | |
|---|---|---|---|
Boris Jabes
Visiting Partner
|
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Luther Lowe
Head of Public Policy
|
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Max Kolysh
Visiting Partner
|
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Brad Flora
Group Partner
|
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Calvin French-Owen
Visiting Group Partner
|
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FAQ
What does Dalton Caldwell invest in?
Dalton Caldwell invests primarily in Software, Artificial Intelligence and Financial Services startups, most often at Pre-Seed and Seed stage. Most of the 190 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.
What is Dalton Caldwell's check size?
Dalton Caldwell typically joins rounds of $1M–$6M at Seed, $500k–$500k at Pre-Seed and $5.1M–$20M at Series A. These ranges are 10th–90th percentile round sizes calculated from confirmed public funding rounds, so they are a realistic guide to the rounds Dalton Caldwell participates in.
When did Dalton Caldwell last invest?
The most recent investment recorded for Dalton Caldwell closed in Jul 2026. Shizune tracks 190 investments in total for this profile, including round sizes, stages and portfolio companies, all sourced from confirmed public funding rounds and refreshed monthly.
Is Shizune's investor data accurate?
Yes — every stat on this profile is calculated from confirmed public funding rounds monitored across hundreds of sources since 2020. This profile was last refreshed in Aug 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.
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