14.ai Dispatch #5
Number five with fries
Hey again,
You asked for Trojan horses and light-up water bottles, right?
No? Weird. We brought them anyway.
Happy late Fourth to those who celebrate.
It was our first Fourth of July in the U.S. as permanent residents and we’re proud to report the roof only has four holes in it.
Workshop: designing smarter support content: AI knowledge bases for teams that ship
Last week was all about wiring your AI agent to the real world: tools, APIs, and fallback logic when things get weird.
Next week, we’re tackling the brain: How does your agent know what to say? And how do you keep it accurate without rewriting the same doc 12 times.
📆 July 9 @ 9am PT
Featuring Nivedha Venkatesh, founder of Pageloop
🍕 Founders dinner: The recap
On Wednesday, we teamed up with Xavier from Index (YC W22) for an epic Founders' Dinner featuring Colin Sidoti of Clerk. No slides, just raw, off-the-record founder talks. 🚀
Breakthrough Bistro: YC founders dinner
We’re co-hosting a dinner on July 22 with Xavier for YC founders in SF.
Come hear Christina Cacioppo, CEO of Vanta, share the unfiltered story behind building her company: real talk, hard lessons, and pasta.
Want to join? Sign up here.
Welcoming Pinkie, our chef intern!
Pinkie is an undergrad at UC Berkeley studying Nutritional Science and Microbial Biology. She's also Head of Product at UNCRACKED, a food-tech startup focused on sea moss and clean-label ingredients.
She’s developed recipes in Bangkok, mentored student founders in plant-based innovation, and holds a Food Safety Manager certification.
Her trial with us? Unreal. Healthier, cheaper, and tastier than our usual Uber Eats. But what sealed it was her application: a love letter to food, science, and care:
“When health became a priority during the pandemic, I became my family’s private chef... I’ve been cooking ever since, to nourish, energize, and care.”
We’re lucky to have her and even luckier to eat her food. 💜
Other cool stuff that happened
Ugo (aka Ugoat 🐐) is coming to San Francisco tomorrow!
We hosted a workshop on getting AI agents to actually do things: tools, APIs, and how MCP fits in. Link to the guide here
Calendly link if you want to jam on AI workflows that don't suck
Reimagining the Trojan Horse… with channels, bots, and bad decisions
We've seen a lot of startups sending thoughtful gifts, like pizzas and donuts, to their peers lately.
We wanted to do something similar.
So this morning, we dropped off large wooden horses (completely empty) at the offices of our closest competitors.
Sometimes the best way in is through the front door.
Cool jobs at 14.ai (and friends)
Looking for a new role? Or a new role to pretend you're applying for? Either way:
🛠️ Founding Engineer @ 14.ai (San Francisco)
🧑💻Customer Support Operations @ Central (San Francisco)
💬 Product Support Specialist @ Anthropic (San Francisco, NYC, Seattle)
Need an intro? We got you.
What we’re reading & listening to this week
Maya: Cultivating depth and stillness in research, Andy Matuschak
Michael: Simple Made Easy, Rich Hickey
Alright, that’s it. Logging off to pet the office dog. We’ll see you in your inbox again soon.
Team @14.ai.








