14.ai Dispatch #18
Airports, agents, and ancient startups.
Onboarding at SFO, AI stacks that ship, and the hottest YC batch of prehistory.
Let’s begin.
Airport offices > WeWork, welcome Matthew!
We don’t onboard teammates. We intercept them at baggage claim.
For Matthew’s first day as founding engineer, we set up shop at SFO: half as a joke and half to see how it actually was.
And honestly, the airport might be the most efficient (and most affordable?) co-working space on earth. Beside the food prices. Sheesh!
Warm welcome to Matthew, we’re so glad to have you.
Founders & Engineers’ typing competition at #SFTechWeek
Think you’ve got the fastest fingers in the Bay?
Join us at the 14.ai HQ for a casual but EXTREMELY SERIOUS typing showdown as part of the 2025 SF Tech Week.
Startup leaders and engineers put speed, accuracy, and stamina to the test. Bragging rights are on the line.
Connect with fellow techie and prove your keyboard game is as sharp as your pitch.
Workshop recap: Knowledge bases that don’t suck
Big thanks to Nivedha Venkatesh, CEO & co-founder of Pageloop, for joining us on Friday.
She broke down how early teams can avoid the “everyone’s answering support tickets in Slack at 2am” phase and actually build a knowledge base people use.
Highlights:
How to stop founders, sales, CSMs, and devs from each inventing their own FAQ
The formatting choices that actually help clarity (vs. the ones that just look pretty in Notion)
Why “make it AI-friendly” doesn’t have to mean “make it unreadable by humans”
🙏 Thanks again, Nivedha!
Upcoming workshop: Beyond trial and error: Building prompts that scale in customer support
Trial and error can get an AI agent off the ground, but it won’t carry you to scale.
Join us for a practical session on building prompts that actually work in production. We’ll cover:
Principles for prompts that give accurate, reliable answers
How to refine across scenarios and channels without starting from scratch
Balancing flexibility with consistency as your support org grows
If you’re tired of one-off hacks and want AI support that scales, this one’s for you.
Best or worst demo ask
In case you missed it
Book a chat bot chat
If you need AI chat support, or your current one gives you migraines, talk to us.
Cool jobs at 14.ai (and friends)
🛠️ Founding Engineer @ 14.ai (San Francisco)
💻 Customer Success Manager @ HockeyStack
⚙️ Customer Success @ Variance
DM us if you have a job to put here...
What we’re reading (so you don’t have to)
Marie: Wherever You Go, There You Are: Mindfulness Meditation in Everyday Life, Jon Kabat-Zinn, PhD
Matthew: Everything I know about good system design, Sean Goedecke
Maya: Can you think like a YC partner? This game will help you find out, Amanda Silberling
Michael: My Lethal Trifecta talk at the Bay Area AI Security Meetup, Simon Willison
Ugo: The great falls of Boeing, Intel, and Apple, David Heinemeier Hansson
Signing Off
May your onboarding happen at arrivals,
your tickets close faster than your laundry cycle,
and your YC batch be hotter than 🔥 + 🛞.
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