14.ai Dispatch #12
From paparazzi clips to prompting tips in 24 hours
One day we’re dodging paparazzi, the next we’re dodging bad prompts.
This week: we got ambushed on camera about AI support, ran a workshop on prompting, and even made it onto a “top startups (that don’t wear shoes)” list.
🎥 Caught on camera: AI support, unfiltered
When the press asks what’s really happening in AI customer support, we don’t spin. We spill.
🍣 Engineering Night: Agents & MCPs in production
Deploying demos is easy. Deploying production agents? That’s the real work.
Join us in the Lower Haight for sushi, tea, and a TypeScript-powered deep dive into:
Moving MCPs + LLM agents from prototype → production
Making the hard trade-offs safely and reliably
Seats are limited (and so is the sushi).
📆 Tuesday, September 9 @ 6 PM PT
✍️ Workshop recap: Prompting for AI support agents
Cyrus Nouroozi, CEO & co-founder of Zenbase (YC S24), joined us live from Edmonton with some hot takes on prompts that survive real-world customer support.
We covered:
How to balance customization vs. standardization in prompt design based on the cost of bad outcomes
Why XML tagging can outperform Markdown in certain cases
Where prompt engineering is heading, from better evaluation methods to higher-level prompting languages
Thank you, Cyrus!
Next workshop: From feedback to action (with Thematic, YC S17)
Customer feedback is only useful if you can act on it. Stuck in silos, buried in spreadsheets, or inconsistently tagged? That’s when customers churn.
Join Alyona Medelyan, PhD co-founder and CEO of Thematic (YC S17), for a live session on:
Organizing feedback so it’s easy to navigate + act on
Avoiding silos and inconsistent tagging
Spotting emerging issues in real time
If you’ve ever lost a customer because their feedback sat untouched… this one’s for you.
📆 Thursday, Aug 28, 1 pm PT
Support gone royally wrong
Marie Antoinette learned the hard way what bad customer support feels like.
Your customers ask for bread.
You tell them to eat cake.
You lose your head.
Listen to your customers.
📊 Poll of the week: What was history’s worst case of “customer left on read”?
📌 In case you missed it
Pitching to a prince: enterprise nerves are one thing, royal nerves are another
Swag laundromat: teammates keep showing up at the office like it’s a laundry service
Second-time founder mode: more patient, more ruthless, less noise. Experience doesn’t make it easier, just sharper
Support Driven Vegas talk: packed room, zero “CSAT questions,” all “RAG + eval metrics.” The industry is shifting
Shoes are canceled: 14.ai listed alongside Cursor and Lovable. Who needs shoes anyway?
Chat support: If you're looking for AI chat support, book some time here with the 14.ai team
💼 Cool jobs at 14.ai (and friends)
In the market for something new? Or just here for the salary benchmarking?
🛠️ Founding Engineer @ 14.ai (San Francisco)
💻 Customer Success Manager @ Pump.co (San Francisco, YC S22)
⚙️ Technical Customer Success Manager @ Brainbase Labs (San Francisco, YC W24)
📚 What we’re reading & listening to this week
Marie: The Twenty Minute VC (20VC) with the founder of Legora (YC W24), Harry Stebbings
Michael: Weaponizing image scaling against production AI systems, Kikimora Morozova and Suha Sabi Hussain
🫡 That’s all for now.
May your prompts tag cleanly, your feedback escape the silos, and your paparazzi questions never be about ticket deflection rates.
Until next time: listen like a prince and debug like a founder.
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