14.ai Dispatch #8
The infinity issue. Like your backlog, but with more snacks.
Dispatch #9 might just be a calendar invite.
⚔️ Ping Pong Duels.
💪 Pushup Showdowns.
♠️ Poker Nights.
🥂 Penthouse Dinners.
The entire history of customer support in 30 seconds
Starts with IBM’s word processor. Ends with a twist.
Watch it if you haven't yet.
Ping pong night recap
What do you get when you mix YC founders, a ping pong table, and deeply questionable grip strength?
Paddle duels.
Mid-match product debates.
Pushup side quests.
And one confirmed 120 WPM flex.
Thanks to everyone who showed up. Co-hosted with the legends at Crustdata (F24), Fondo (W18), Index (S19), AgentHub (S25).
More unhinged founder events soon. 🏓
Poker Night: All-in on build mode
We’re betting the roadmap on a flush.
Join us in the Lower Haight for cards, snacks, and unfiltered product takes.
No pitch decks. Just real decks.
No pitches. Just builders.
All skill levels welcome, from absolute beginners to the guy who definitely watches WSOP clips on 1.5x speed.
📆 August 6 @ 6 PM PT
Workshop: From "vibe check" to launch checklist
Your prototype kinda works.
Now what?
In this session, we’ll cover how to go from internal demo to real-world deployment without breaking stuff (or trust).
Topics include:
• Preflight checks for AI agents
• Using evals without dashboard doomscrolling
• Post-launch ops: permissioning, escalation paths, and avoiding the 3AM Slack ping
📆 July 31 @ 9 AM PT
YC founders dinner with the CEO of Vanta
We co-hosted a Breakthrough Bistro dinner with Xavier Pladevall and Christina Cacioppo, CEO of Vanta, as our guest of honor.
We brought together 11 YC founders for an off-the-record conversation about the chaos of company-building - the parts no one tweets about.
Christina set the tone with honesty and precision. The group followed suit.
Special thanks to Annie Lu for hosting us at her 301 Mission listing, possibly the most absurd venue we’ve ever used for a founder dinner.
More nights like this soon. 🥂
📨The first email ever
In 1971, a computer engineer named Ray Tomlinson sent the first email ever.
He was working on ARPANET, the predecessor to the modern internet.
A network so groundbreaking that almost nobody outside the U.S. Department of Defense knew it existed.
Tomlinson had to invent the concept of email itself.
He chose the @ symbol to separate a user from their host machine.
He wrote the code that let one computer message another.
And then, history was made.
The first email traveled just a few feet, from one machine to another sitting beside it.
But it marked the beginning of a new era.
A moment that would fundamentally reshape how humans communicate, collaborate, and connect.
The contents of that first email?
Hey [Name],
I know you're probably heads-down right now, so I’ll keep this quick.
I came across one simple trick that’s been helping teams generate 20+ leads fast - without lifting a finger.
Thought it might be relevant given what you’re working on.
Open to a quick call this week? Calendly below.
Some things never change.
In case you missed it:
Cool jobs at 14.ai (and friends)
Looking for a new role? Or just need a new tab to keep open while you pretend to job hunt?
🛠️ Founding Engineer @ 14.ai (San Francisco)
💬 Technical Support Specialist @ Attio (Remote)
🧑💻Technical Support Engineer @ Braintrust (San Francisco)
Need an intro? We got you.
What we’re reading & listening to this week:
Maya: How Distillation Makes AI Models Smaller and Cheaper, Amos Zeeberg
Ugo: Founding Sales: The Early Stage Go-to-Market Handbook, Pete Kazanjy
Michael: The Moscow Puzzles: 359 Mathematical Recreations, Boris A. Kordemsky
🫡 That’s all for now.
Thanks for making it past the paddle battles, penthouse confessions, and poker metaphors stretched to their absolute limit.
Until next time: ship confidently, shuffle wisely, and if your agent hallucinates, at least let it call for backup.
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