14.ai Dispatch #21
Fast replies, faster runners.
TikTok HQ visits.
Texting “BUY” to purchase new shoes.
We might be brainrotted, but at least we’re efficient.
Team spotlight: Maya
We followed Maya around and asked her random questions like a startup nature documentary.
She’s founding engineer who joined the team in April, and has been our fast-typer-in-residence ever since.
We’re lucky to call her a teammate and a friend.
AI agents at the checkout line
AI support agents are heading to checkout. Like your mom in Macy’s during holiday season.
Join us for sushi night in the Lower Haight as we talk about what happens when your AI starts handling refunds, recommendations, TikTok Shop DMs, and 10.8 billion “just wondering where my order is.”
How to craft prompts that don’t gaslight your customers
Building agents that can sell and say sorry
Guardrails, evals, and philosophical debates about tone (“Is :) passive-aggressive?”)
📆 Thursday, November 6 @ 6 PM PT
Next workshop: AI and the new era of brand discovery
Fashion meets data. Creativity meets code.
Join Renan Serrano, founding evangelist at Athena (YC W25), and us for a live session on how AI is reshaping brand discovery, from search to storefront.
We’ll cover:
How AI search results are changing how customers find and fall in love with brands
What “brand identity” means in an algorithmic world
How founders can stay discoverable without losing authenticity
If your brand lives online, this is one conversation you don’t want to miss.
Wednesday, October 29th at 9 am PT. We’ll be wearing our Halloween costumes.
Workshop recap: Turning support into sales
We broke into Jonathan Fudem’s house, co-founder and CEO of OneText (YC W23), and forced him to record a podcast with us.
His company lets you buy products entirely over SMS.
Which means you can now impulse-shop without even opening Safari.
We talked about the future of conversational commerce, from people shopping through LLMs to the dark art of support.
We covered:
Where the hell my order is
How to track my order (seriously, where is it)
Let me talk to a human, WHERE IS IT
Free hitchhiking to work
Excited to announce a game-changing employee benefit:
We now offer free hitchhiking to work.
Any employee can now simply go outside, stick their thumb out, and someone will probably pick them up, completely free, and drop them off somewhere near the office.
Early results are promising:
87% of employees arrive within 2 hours of their intended start time, and we’re seeing incredible cross-pollination as team members network with long-haul truckers and doordash drivers.
This is what happens when you combine Silicon Valley innovation with a $0 transportation budget.
Talent is our greatest asset.
In case you scrolled past it
TikTok HQ visit: Building smarter support (and thanking them for the dog videos).
MrBeast mode: Founders vs. 100 paying customers.
Support POV: Everything is a ticket. All I see are tickets.
Family-owned startup: Marie explains why marrying your cofounder might actually work.
It’s time to move on
If your current chatbot sounds like your ex when they were hungry, let’s chat.
Cool jobs at 14.ai (and friends)
🛠️ Founding Engineer @ 14.ai (San Francisco)
💻 Customer Service Manager @ Cityfurnish (Gurugram, India)
⌨️ Customer Support Specialist @ VetRec (Seattle, WA or remote)
What we’re reading (so you don’t have to)
Marie: YC Partners Answer Your Questions | Office Hours, Y Combinator
Matthew: Summary of the Amazon DynamoDB Service Disruption in the Northern Virginia (US-EAST-1) Region, Amazon
Maya: The browser wars are back, and this time they’re powered by AI, Theresa Loconsolo
Michael: Conversation with Karim Atiyeh, Patrick OShaughnessy
Ugo: Darwin Gödel Machine: Open-ended evolution of self-improving agents, Zhang et al., 2025
Somewhere between “please hold” and “order confirmed,” progress happens. Thanks for being part of it.
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