Ambiguous
portfolio deal
Ambiguous AI - Deal Memo
Status: Invested Stage: Seed Thesis: Ryan is the next Satya
Summary
One-liner: AI coworkers that work like real teammates in Google Workspace, Slack, and email - not chatbots, but autonomous agents with real identities.
Founders:
- Ryan Waliany (CEO) - Former CEO @ Doorstead (raised $40M, $10M ARR, partnerships with Zillow + Opendoor). UC Berkeley, Carnegie Mellon dropout (robotics under Drew Bagnell). 4x ACM competitive programmer. Led social mobile cooking community acquired by ABC Cooking/Uber.
- Philip Lee (CTO) - Former CTO @ Doorstead. Built Alexa automation platform (100M+ workflows/day). Youngest applied AI researcher at Microsoft. Founded AI company sold to IAC. Graduated college at 18.
- Dan Hsiao (CPO) - Former VP Product @ Doorstead. First product hire at FriendFeed (worked with Bret Taylor + Paul Buchheit). Co-created Facebook Messages. First consumer PM at Instacart, co-created Curbside Pickup.
Why I Invested:
Ryan is a generational founder. When I met him, I saw the same quality I saw in George (Honey) and Alex (Metropolis) - absolute conviction, tangible vision, and the obsession required for 1000x outcomes. He's the next Satya.
The team is exceptional:
- All three co-founders built and scaled Doorstead together
- Philip built infrastructure that powers 100M+ workflows/day at Amazon
- Dan was at the creation of Facebook Messages and Instacart's consumer product
Round: $5M Seed
Investment Thesis
1000x Opportunity?
Absolutely.
- TAM: $87B (business ops specialists) + $157B (admin assistants) = $244B labor market
- They're positioning as "the third wave" after coding agents (Cursor/$219B) and customer service (Decagon/$113B)
- Vision: Be the "Shopify for Agents" - platform where anyone can build and deploy AI coworkers
Kingmaker Fit?
Strong - Can help with enterprise distribution and technical architecture. Ryan's team has the GTM expertise, but my CTO network can accelerate enterprise adoption.
Why Ryan = Next Satya
The Satya comparison isn't hyperbole. What I observed:
- Platform thinking - Not building a point solution, building an operating system for human-AI collaboration
- Execution velocity - 8 weeks to early PMF signs (3.9K weekly human-AI interactions)
- Team assembly - Recruited two exceptional co-founders who bet their careers on him (again, after Doorstead)
- Conviction under uncertainty - Building in the "AI coworker" space before it's consensus
When Ryan talks about Ambiguous, you can see the future he's describing. That's the George/Alex quality.
Key Details
Product:
- AI coworkers with names and identities (not chatbots)
- Works natively in Google Workspace, Slack, email
- Proprietary agentic framework with memory and learning
- Use cases: scheduling, CRM updates, research, internal ops
Traction:
- 3.9K weekly human-AI interactions (8 weeks from launch)
- Validated by DocuSign CEO, Microsoft Teams SVP, Google Cloud BD exec
- Waitlist includes Apple, Meta, Amazon, Google, Microsoft, LinkedIn, Canva, DocuSign
Partnerships:
- a16z Speedrun (60 out of 14,000 selected) - $5M in credits, direct a16z network access
- Google Cloud ISV Springboard - GCP launch target 1/2026
Roadmap:
- Q3 2025: Build multi-agent OS
- Q4 2025: 1000 daily active agents
- H1 2026: 1000 paid agents ($340K ARR)
- H2 2026: $10M ARR with 10x ramp into 2027
Documents
ambiguous_investor_deck_1.pdfParable - Ambiguous - Series Seed Termsheet - For Signature (1).pdfSigning_Package_for_Ambigous_AI_-_Series_Seed.pdffunding 2025 safe ambiguous ai.pdf
Contacts — Ambiguous AI
Founders
| Name | Role | Phone | ||
|---|---|---|---|---|
| Ryan Waliany | CEO | — | — | — |
| Philip Lee | CTO | — | — | — |
| Dan Hsiao | CPO | — | — | — |
Backgrounds:
- Ryan — Former CEO @ Doorstead ($40M raised, $10M ARR). UC Berkeley, CMU dropout (robotics). 4x ACM competitive programmer.
- Philip — Former CTO @ Doorstead. Built Alexa automation (100M+ workflows/day). Youngest applied AI researcher at Microsoft.
- Dan — Former VP Product @ Doorstead. First product hire at FriendFeed (Bret Taylor, Paul Buchheit). Co-created Facebook Messages.
Relationship Timeline
- 2025 — Invested in Seed round
Last Touchpoint
- Date: 2025
- Status: Invested
- Next Action: Monitor progress toward 1000 daily active agents (Q4 2025 target)
Notes — Ambiguous AI
New entries at top.
2025 — Investment Decision
Type: Investment
Summary: Invested in Seed round. Core thesis: "Ryan is the next Satya."
Key conviction points:
- Ryan shows the same quality seen in George (Honey) and Alex (Metropolis)
- All three co-founders built and scaled Doorstead together
- 8 weeks to early PMF signs (3.9K weekly human-AI interactions)
- a16z Speedrun selected (60 of 14,000)
- Waitlist includes Apple, Meta, Amazon, Google, Microsoft
Milestones to watch:
- Q4 2025: 1000 daily active agents
- H1 2026: 1000 paid agents ($340K ARR)
- H2 2026: $10M ARR target