14.ai Dispatch #9
From Skydiving to Customer Support in 9 Clicks
Dispatch #9 walks into the Lower Haight, orders a matcha mocktail, and wins a prompt battle.
The Wikipedia 500: Chaos on clicks
What happens when you lock a bunch of engineers in a room and tell them to navigate Wikipedia fast?
You get:
Link-count smack talk
High-speed philosophy detours
Someone yelling “Wait how did I end up on Horse grooming??”
One brave soul routed through Jorts the Cat. No regrets.
Welcome to the first-ever Wikipedia 500: a footrace for your brain, where contestants navigate from one random Wikipedia page to another using only internal links.
No CTRL+F. No back button.
Watch the recap video here.
We'll see you on the blue links.
“Have You Tried Prompting It?”: Sushi + support night recap
We gathered 15 support leads, founders, and AI obsessives for a night of unfiltered prompting, sushi bowls, and matcha mocktails.
There was drama. There was laughter. There were prompts that could crash a CPU.
We ended the night with a live prompt battle judged on creativity, clarity, and chaos.
👀 Winner reveal coming soon. Stay tuned.
Workshop: Your KB is not your blog
Your knowledge base isn’t vibes. It’s infrastructure.
And if it reads like a thought dump from 2022, your AI agent is already crying.
Join us for a session with the CEO of Pageloop on how to make your KB truly AI-native (and why your current one might be sabotaging your support).
We'll cover:
• Structuring articles for retrieval (not just skimming)
• Handling multi-product complexity (shoutout to the Enterprise teams)
• Keeping it fresh in a world where your product changes every 3 hours
📆 August 6 @ 9 AM PT
It all started with a broken link
July 1991. The first website goes live.
August 1991: “Hi, the link isn’t clickable. Am I doing something wrong?”
And just like that, customer support was born.
In case you missed it:
Michael is presenting at Support Driven Expo in Vegas: just him, his bot, and a dream. 🎲🤖
Michael shared the ultimate Zoom hack: the bouncing DVD logo.
We went to Barry's bootcamp with YC founders and don't feel our legs anymore.
AI agents, activated: we wrapped our launch workshop with guest speakers from Miami and London.
Cool jobs at 14.ai (and friends)
Looking for a new role? Or just need a job tab open in case your boss walks by?
🛠️ Founding Engineer @ 14.ai (San Francisco)
💬 Support Manager, Billing and Accounts @ Zapier (Remote, EST)
🧑💻Senior Manager, Technical Support Engineering @ Datadog (San Francisco)
💬Founding CX and Partnership @ Pincites (Remote, US)
Need an intro? We got you.
What we’re reading & listening to this week:
Maya: Linear’s Path to Product-Market Fit — Quality and Craft > Speed and Scale, featuring Karri Saarinen
Marie: A Cheeky Pint with OpenAI cofounder Greg Brockman, Stripe
Michael: Fast, Catherine Jue
🫡 That’s all for now
Thanks for surviving the click chaos, CPU meltdowns, and knowledge base roasts.
Until next time: debug boldly, prompt responsibly, and never trust a link with blue underlines and bad intentions.
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