14.ai Dispatch #13
Betting on hotel Wi-Fi, then betting on which founder can prompt best.
This week: startups in Vegas, founder poker night, and how AI feedback is evolving support.
All in: poker night for founders
Turns out the riskiest plays aren’t always on the fundraising deck.
Prompting showdown, founder edition
This time, we're taking the stage at the Smart 100 AI Summit in SF on Tuesday.
The challenge: which founder has the sharpest prompting skills?
Last time it was engineers… now it’s the founders’ turn.
Stay tuned - more details to come soon.
Register here and reply to this email if you want a friends and family code.
From the page to IRL
This week, we had a special visitor, Victoria Crow Dog, Head of Global Support at HackerRank (YC S11). We had some great conversations, shared a few stories around our book, and talked about the future of support. Check out her post here.
Workshop Recap: Supercharging support with AI
We sat down with Alyona Medelyan, PhD, CEO and co-founder of Thematic (YC S17), for a Q&A on transforming fragmented customer feedback into actionable insights.
Highlights:
The newsroom model for breaking down silos and aligning teams
Real-world examples where feedback drove major process changes, not just small tweaks
How CSAT and NPS are evolving into mission-specific measurements in an AI-first world
Thanks Alyona for the expertise, and to everyone who joined us live.
📄 Full recap here.
Next workshop: Context is king
AI agents promise speed and personalization in support - but without the right context, they hallucinate, stumble, and lose trust.
Join us Wednesday at 9 am PT with Marcus Storm-Mollard, CEO & co-founder of Clarm (YC X25). Clarm is building deep research agents for finance, law, and healthcare; places where accuracy isn’t optional.
We’ll cover:
How startups and enterprises use context windows to resolve issues faster
Bringing AI into compliance-heavy environments without losing trust
Why context-grounded agents are reshaping operating models
We’ll close with a live Q&A with Marcus on lessons from Clarm’s journey and the future of AI-native support.
📆 Wednesday, 9 am PT
Berlin Wall hotline
November 9, 1989 was crazy
Poll of the week
In case you missed it
Startup Vegas edition: the kind they don’t advertise on the Strip.
Happy 14th to Intercom: older, wiser, still kicking.
Board meeting or Sunday brunch: What it’s like starting a company with your life partner.
Marie shares how she met her co-founder: proof that game night can turn into company night.
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)
Actively applying or passively procrastinating? Either work.
🛠️ Founding Engineer @ 14.ai (San Francisco)
💻 Manager of Technical Support @ HackerRank (YC S11, hybrid in Bangalore, India)
⚙️ Senior Manager, Technical Support Engineering @ Datadog (San Francisco)
Need an intro? Just ask.
What we’re reading & listening to this week
Marie: The Truth About the Harry Quebert Affair, Joël Dicker
Maya: The AI Was Fed Sloppy Code. It Turned Into Something Evil, Stephen Ornes
Michael: Who Validates the Validators? Aligning LLM-Assisted Evaluation of LLM Outputs with Human Preferences, Shankar et al
Ugo: Please Stop Using Booleans, Theo - t3.gg
🫡 That’s all for now.
May your board meetings feel like brunch, your poker nights stay friendly, and your prompts hit cleaner than a Vegas shuffle.
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