Chai & AI Community
Problem-First AI Thinkers, Sunday Morning Conversations
A curated, invite-only group where we cut through the AI hype, stay updated on what truly matters, and connect over expert-led discussions, workshops, and hands-on sessions.
There's so much happening in AI right now, and everyone seems to be hearing a different version of what matters. Most AI learning spaces tend to attract the same kinds of people, follow rigid formats, and leave little room for honest, casual conversations: the kind you'd have over chai with a friend 🍵.
Chai & AI is our antidote to that.
It's a curated, invite-only community of problem-first AI thinkers: folks who've worked with Aish and Kiriti, alumni from places we've taught, and respected peers in the field.
Every Sunday morning, we meet for freeform conversation. Some weeks we bring in a guest, put them in the spotlight, and ask all the questions we're too shy to ask in public. Other weeks, we just pick a topic and spill tea. It's completely unstructured and confidential with no recordings, no scripted agenda.
We talk about everything. New AI product and model announcements, the latest buzzwords and what they actually mean for enterprise practitioners, how hiring is shifting, what gives AI products a real moat, how teams are handling change, what education looks like in this new world, founder mindset, and whatever else people are thinking about that week. And plenty more.
Featured Sessions
Check out our most popular Chai & AI sessions and notes. You can find longer notes and session summaries on Substack.

Francisco D'souza
Former CEO of Cognizant, Co-Founder of Recognize
Leading Through Uncertainty & The Future of AI-Enabled Services



The Chai & AI Expert Network
Many of our members offer advice and perspective to each other, sharing what they've learned in the enterprise world, whether in group discussions or through 1:1 consults. With such a high concentration of talent, members often gain valuable industry insights directly from one another.
Our community includes product and engineering builders and leaders at FAANG+ and deca-unicorn companies, founders of YC-backed startups, senior leaders at Fortune 100 companies, solutions leaders, and more. It's a space to exchange knowledge and help each other close gaps.
How to Join
The Chai & AI community is invite-only to maintain the quality of our candid discussions and ensure everyone is aligned with our problem-first approach. All our Maven cohort students get temporary access to these sessions while they take the course, and then we float an application to select interested folks for continued participation.