14.ai Dispatch #26
Microphones, macarons, and management escalations.
Microphones causing “emotional damage” and cacao ceremonies for startup founders, here’s what we’ve been up to.
Karen training simulator
We stood on the street for hours paying people to be Karens. First of many clips to come. (also snaps for Michael’s acting skills)
Cool reminder that no matter how good your AI gets, there will always be someone ready to ask for the manager.
LA TikTok Shop meetup (yes, we’re doing this)
December 5 @ 1 Hotel West Hollywood
Macarons. Champagne. People who understand why your conversion rate randomly disappeared last Tuesday.
If you’re selling beauty, wellness, home goods, or whatever weird thing is trending this week, you know TikTok Shop is basically controlled chaos.
One day you’re crushing it. The next day your best affiliate ghosted you and Mercury is in retrograde.
We’re getting a small group together to talk about what actually works, what definitely doesn’t, and how to build something that survives longer than a trending sound.
If you’re in LA or know someone who should be there, send them our way!
Nashville grind time 🤠
Michael and Ugo have been posted up in Nashville all week doing the glamorous work with a customer: shipping code, fixing bugs, and prepping for whatever comes next. Living the dream, etc.
Cacao Ceremony for YC women
San Francisco YC women founders: this one’s for you.
We’re hosting an evening cacao ceremony and women’s circle at Alchemy Springs in Lower Nob Hill, created specifically for YC women founders who want a calm space to reconnect, reset, and meet each other outside the usual pace of startup life.
We’ll move through guided cacao and breathwork, share dinner in a small circle, and close with tea and quiet connection. No experience needed, just comfortable clothing and willingness to unplug for a bit.
If you’re in SF or know a YC woman founder who would appreciate this kind of gathering, feel free to pass it along.
Scaling creator partnerships (without losing your mind)
How do you scale creator partnerships when you don’t have a whole team to babysit them?
Jeremy Yaoxin Ding, Co-founder and CEO of Euka AI, has helped some of the fastest-growing TikTok Shops uplevel their systems.
Join us for a live session on how top shops automate creator discovery, streamline outreach, and turn affiliates into predictable revenue.
If you want to understand how high-performing teams hit consistent 5 and 6 figure GMV months, we’ll explore:
How AI automates creator discovery and outreach at scale
How winning shops manage thousands of affiliates with smart CRM and re-engagement
How to identify high-performing hooks, scripts, and formats using social intelligence
How AI-generated briefs and content speed up testing and iteration
How top teams structure ops for predictable, repeatable GMV
Perfect for founders, operators, and anyone trying to make TikTok Shop feel less like gambling.
📆 Wednesday, December 3
Happy Thanksgiving from Team 14.ai 🦃
With Thanksgiving this week, here’s a moment from last week’s Effect dinner. Started with homemade ravioli, ended with a deep dive on functional programming and AI agents. Very on-brand for this crowd.
We’re grateful for everyone who keeps showing up with ideas, questions, and the kind of curiosity that makes both the work better and the dinners way more interesting.
Speaking of Thanksgiving...
Most common Thanksgiving support tickets we saw this year:
“Someone brought store-bought rolls acting like they cooked”
“Why does every dish have raisins in it?”
“This turkey is dry.”
“Cousin walk group is giggling at the Jell-O.”
“Football volume too loud” / “Football volume too quiet”
“Who put me next to the cousin who breathes like a leaf blower?”
“Mother-in-law asked when we’re having kids again” - Recurring issue.
“Someone’s kid is showing me YouTube videos”
“Dad asleep on couch by 4pm”
Closing all tickets. See everyone in 364 days.
If your chatbot is acting up in front of guests 😡
Bring it to us. We’ll tune it up together.
In case you missed it
Riva spotlight: our lab gives world-class greetings and excellent office vibes.
Founder titles: why two CEOs list customer service first and mean it.
Thanksgiving triage: the annual family chaos handled like a support queue.
Jobs that justify living near a Barry’s
🛠️ Founding Engineer @ 14.ai (San Francisco, CA)
⌨️ Support Executive @ Landeed (Hyderabad, Mumbai, Chennai, Bengaluru, India)
🩺 Clinical Customer Success & Implementation Specialist @ Knowtex (San Francisco, CA)
What we’re currently quoting
Marie: The Surrender Experiment: My Journey into Life’s Perfection, Michael A. Singer
Matthew: Local first-access control, Ink & Switch
Maya: Carlo Rovelli: ‘Time Is an Illusion’, Quanta Magazine
Michael: An Economy of AI Agents, Gillian K Hadfield and Andrew Koh
Ugo: The Visual Display of Quantitative Information, Edward R. Tufte
🫡 Signing off. Wishing you stable funnels, calm inboxes, and dinners that turn into great ideas just when you least expect them.












