Dispatch #14
Yeah, we hit number 14. Do we even need to explain why that’s special?
From summit prompt battles to forgotten flops, and everything in between.
Prompt battle @ Smart 100 AI Summit
We brought our favorite party trick to the Smart 100 AI Summit: prompt battles.
Founders on stage, sweaty palms, GPT staring them down. Who’s got the sharpest prompt under pressure?
Shoutout to Conor Brennan-Burke (co-founder & CEO at Hyperspell, YC F25) for walking away with the crown 👑.
Agents & MCPs: Sushi edition
Demoing agents = 🥰
Shipping agents = 💀
We’re doing what any reasonable team would do: hosting an engineering night with sushi + tea while we argue about TypeScript.
Jamming on:
Moving MCPs + LLM agents from prototype → production
Trade-offs that make you question your life choices
📆 Tuesday, September 9 @ 6 PM PT
Sign up here.
Workshop recap: Grounded support agents
Marcus Storm-Mollard, co-founder & CEO of Clarm (YC X25), dropped in to explain why “just make the context window bigger” is not a strategy.
Highlights:
Why “more tokens” isn’t always better
Building agents regulators won’t roast
How retrieval + synthesis actually changes support
Thank you, Marcus, for the insights!
Next workshop: Evals or bust
AI agents in production are like interns on their first day: confident, ambitious, and totally unreliable.
Join Brooke Hopkins, Founder and CEO @ Coval (YC S24) to talk about:
Why evals = airbags for AI
How to stop regressions before your customers do
What testing looks like when agents go multimodal
You know if you need to be there...
📆 Wednesday, Sept 10, 9 am PT
Google+: The flop that flopped
"Look at this picture and tell me the first thing that comes to mind."
Imagine being the poor soul in charge of the support tickets.
First came "Circles", Google’s idea that you’d sort every friend, coworker, and acquaintance into little buckets before posting. Yeah, nobody using that chief.
Then, the infamous YouTube integration. Suddenly, you couldn’t comment without a Google+ account. You probably remember how the internet reacted.
Despite Google’s scale, it was a major flop. Most people signed up once (usually by accident) and never came back. By 2019, after a data bug exposed user info, it was quietly shut down.
Did you actually use it? What was it like?
Poll of the week
In case you missed it
Riva’s ticket: From product bugs to dog treats, we’ve got it covered.
14.ai received the David & Goliath award at the Smart 100 AI Summit.
Every hat: Startup life means founder, chef, and furniture mover in one.
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)
Looking for a new role, or just avoiding the one you already have.
🛠️ Founding Engineer @ 14.ai (San Francisco)
💻 Customer Support Specialist @ Delphi (San Francisco)
⚙️ Director, Customer Support @ Shippo (Remote, United States)
Need an intro? Just ask.
What we’re reading & listening to this week
Marie: Michael Truell: Building Cursor At 23, Taking On GitHub Copilot & Advice To Engineering Students, Y Combinator
Maya: Inside vLLM: Anatomy of a High-Throughput LLM Inference System, Aleksa Gordic
Michael: You Have to Feel It, Mitchell Hashimoto
🫡 That’s all for now.
May your prompts stay sharp, your co-founders stay grounded, and your product launches age better than Google+.
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