CEO of Ambiguous AI
Ryan
Waliany
Serial entrepreneur. Angel investor. Community builder. Scaled two companies from zero to $10M+ in revenues and raised $40M+ along the way. Now building AI that works alongside people as real teammates.
CEO of Ambiguous AI
Serial entrepreneur. Angel investor. Community builder. Scaled two companies from zero to $10M+ in revenues and raised $40M+ along the way. Now building AI that works alongside people as real teammates.
Now
Today, AI is session-based. You open a tool, type a prompt, get a response. It's powerful, but it only augments you while you're at a computer and disappears when you're not.
Ambiguous is different. We're building AI coworkers that work like real teammates. Each one has a real Google Workspace account: their own Gmail, Calendar, Drive. Completely separate from yours. You can forward them an email, cc them on a thread, or assign them a task in Slack. They don't wait for your prompt. They pick up work, coordinate with your team, and handle the back-and-forth until it's done.
Part of a16z Speedrun. Was it human or AI? It's Ambiguous.
Outside of work, I'm using AI to teach my kids math, sharpen my poker game, and optimize my fitness. Always building.
Investing & Advising
I invest in pre-seed and seed companies as an a16z Speedrun scout, through a warehoused fund, and personally. I'm also an active advisor to a handful of companies. These ventures, combined with lessons from building my own, help me mentor founders navigating the early chaos.
a16z Speedrun Scout Investments
Community
I host a handful of events for fun: intimate dinners, museum gatherings, and a monthly founders lunch in Bellevue with 25+ founders.
Thank you to JPMorgan, Rho, WSGR, Cooley, and Goodwin for sponsoring.
Founder Dinner Gala at Chihuly Garden and Glass
Founder Dinner Gala at Chihuly Garden and Glass
Founder and investor dinner at the Ferry Building, SF
Intimate founder dinner at Staple & Fancy
Monthly founders lunch at La Mar, Bellevue
Principles
Startups are a game of luck and skill
Working hard and smart is not enough. It takes discipline
Relationships are the foundation to success
Coaching is essential to refining your craft
Frameworks and processes are gifts that save time
History repeats itself, often rhymes with every new breakthrough
First principles and systems thinking unlock new paradigms
You can just do things
Writing
Background
Career
Ambiguous AI · CEO & Co-Founder · 2025 to present
Building AI coworkers that work like real teammates. Each one gets their own Gmail, Calendar, and Drive, and they pick up work without waiting for a prompt. Part of a16z Speedrun SR005. Rooted in my AI and cognitive psychology background from Berkeley.
Doorstead · CEO & Co-Founder · 2019 to 2025
Co-founded Doorstead, an AI-enabled property manager that guarantees rent before finding a tenant. Raised $40M and scaled to 150+ employees, just under $10M ARR, and 2,000+ property owners managing over $1.5B in property value.
Signed a category-defining partnership with a $12B real estate company. Reached profitability, then hired a CEO to run the business. Now serve as Chairman of the Board.
Covered by TechCrunch · GeekWire · Inman · Bloomberg · Built In SF
Uber · Product Manager · 2016 to 2019
Led a growth team under Andrew Chen, making Uber social and building viral loops for meetups with friends. Later joined the Sensing, Inference, and Research team where we built trip inference models using GPS and sensor data, ran active AI (human-in-the-loop) research, and applied it to core businesses like Eats and Trips to optimize dispatch timing and delivery efficiency. Filed patents on AI and operational efficiency and co-authored research on ML trip optimization.
Covered by Uber Engineering · The New Stack · ML Times
Kitchenbowl · CEO & Co-Founder · 2013 to 2016
Built Kitchenbowl, the first social mobile cooking community with looping video clips for cooking techniques. Apple featured it as “Best New App” and App of the Day. Our collaboration “Kids Try Breakfast From Around the World” hit 31M+ views. The product was acquired by ABC Cooking Studio, a deal that started with a cold email I sent a year before. The team was acqui-hired by Uber and Instacart.
Covered by TechCrunch · GeekWire · The Spoon · Brit + Co
Bullet Media (CTO), Idealix (CEO), Permuto (Engineer) · 2009 to 2013
Scaled Bullet Media (now Adlogica), a performance marketing company, to $6M in annual revenue. It eventually reached $30M. Created Word Seek, a mobile game with over 2 billion minutes played, the #1 word game in 9 countries and #2 in the US. Bootstrapped and profitable from day one. Also worked at Permuto (later BuySight, acquired by AOL) building distributed systems.
Covered by TechCrunch · AllThingsD · AdExchanger
Education & Research
UC Berkeley · B.S. EECS, B.A. Psychology · 2004 to 2008
Taught AI with Dan Klein, researched computational modeling under Tom Griffiths, and represented Berkeley four times in ACM programming competitions.
Worked on the “Ghostrider” self-driving motorcycle with Anthony Levandowski for the DARPA Grand Challenge. Interned at JPL building an FPGA-based stereo vision system for the Mars Rover. Microsoft Technical Scholar (full tuition covered), interned at Live Labs and Ad Labs (applied AI), and worked on migrating Windows Mobile OS to ARM.
Co-founded HotSwap, the first video-commerce marketplace where Steve Wozniak sold the first car on the platform. We partnered with Red McCombs Automotive and were featured by Business 2.0. It didn't work out, so I went to graduate school to pursue robotics.
Carnegie Mellon University · M.S. Robotics · 2008 to 2009
Researched tele-operated mining vehicles under Drew Bagnell (co-founder of Aurora). Completed coursework and took a permanent leave of absence to go back to building companies.
Outside of Work
Nonprofit & Mentorship
VP of Finance on the Cal Alumni Association Board (2016 to 2020). Mentor at Taiwan Startup Stadium, helping startups expand into the US, Japan, and Southeast Asian markets.
At the table
Cashed at the World Series of Poker. 10,000 players start and maybe 10 make the final table. I never got to the final table, but it taught me what startups already teach: it takes luck and skill to survive any game of chance. Keep playing and refining your craft.
Contact
Whether you're a founder looking for advice, an investor exploring opportunities, or just someone who wants to talk shop, I'd love to hear from you. You can also find me on LinkedIn.
