Roske.AI | Program edition | Week of October 3, 2026 October 9-10, 2026
October 9-10, 2026 | Puerto Rico Convention Center | San Juan
On October 9 and 10, the Caribbean AI Summit takes over the Puerto Rico Convention Center, and I'm co-chairing it (which mostly means telling everyone I know to come, so consider yourself told). More than 30 speakers across 3 tracks, 2 days, and every session subtitled live in English and Spanish, so pick your favorite language and come.
Venue art: Caribbean AI Summit
01 | The lineup
The 3 people the summit led with are the World Economic Forum's former Head of AI, a principal research scientist from MIT's Senseable City Lab, and an AI advisor to the European Parliament, and all 3 will be in San Juan on October 9 and 10 along with more than 30 other speakers. I'm going to let that list make the case for Puerto Rico instead of making it myself (Edward, you live here, so nobody should take your word for it, and frankly you'd oversell it).
Day 2 | 4:45 PM | Closing keynote, Technical
Former Head of AI, World Economic Forum
The Global State of AI: Governance, Risk & What's Next
CEO of Good Tech Advisory, and her latest book, Coexisting With AI, came out in January. If you've ever been asked who's accountable when the model gets it wrong, her talk is the one to catch.
Day 1 | 9:00 AM | Opening keynote, Business
Principal Research Scientist, MIT Senseable City Lab
AI for Urban Biodiversity
His lab builds vision models that count insects in city gardens on low-power hardware, which is one of the most practical uses of AI I've seen on any program (and the only talk this year where the bugs are the point).
Day 2 | 4:45 PM | Closing keynote, Business
President, OdiseIA | AI advisor to the EU Parliament
Ethics & EU Regulation: the Global Playbook
She sits on the expert team for AI regulation at the European Parliament's AI Observatory and works on Spain's AI regulatory sandbox, so when she tells you what the AI Act will actually ask of you, she's describing her week.
AI faculty from MIT, Carnegie Mellon, UC Berkeley, Penn, and SMU (where I got my data science degree, so I'm biased and I'll be in the front row), plus people building this for a living at Microsoft, Salesforce, Snowflake, Databricks, AWS, HPE, and a bunch more. Full list at caribbeansummit.ai.
Stephen Smith
Carnegie Mellon | AAAI President
AI for Smart Cities & Urban Mobility
Pablo José Hernández Rivera
Resident Commissioner of Puerto Rico
Fireside Chat: AI in Puerto Rico and Beyond
Tim Berglund
Confluent
A Brief History of Artificial Intelligence
Gauthier Vasseur
UC Berkeley | Fisher Center
Beyond AI: Building AI-Capable Organizations
René Vidal
University of Pennsylvania
Engineering Trustworthy AI Systems
Giselle Zeno
MIT Lincoln Laboratory
Do's and Don'ts in the Agentic AI Era
Julian Duque
Salesforce | MuleSoft
So You Have 50 Agents. Now What?
Dash Desai
Snowflake
Building on Cortex AI
Gary Crisci
Caprus AI
Smart Models, Naive Systems: Context Engineering for the Enterprise
Bivin Sadler
Southern Methodist University
AI-Powered Oral Exams
Gary Crisci works at Caprus AI, where I'm an investor, so weigh my enthusiasm for his session accordingly. Headshots courtesy of the Caribbean AI Summit.
Writing and video, newest first, including this week's post on what a WEF, MIT, and EU Parliament lineup is actually going to disagree about.
02 | The program
Business is in Ballroom B, Technical in Room 209, and Society in Room 208, all running at once, so you'll have to choose. If you run finance and you only have the patience for about 10 sessions, I've marked my route through both days (it isn't official, and I reserve the right to wander into the healthcare panel instead).
Opening keynotes
Keynotes
Keynotes | Puerto Rico's AI Moment
Keynote & Business AI Panel | Ballroom B
Closing keynotes, plus the hackathon awards
As published at caribbeansummit.ai, last updated September 2026, and subject to change. Times are Atlantic Standard Time, and Puerto Rico doesn't do daylight saving (one less thing to explain to your calendar). Both closing keynotes run at 4:45 on Day 2 in different rooms, so you'll have to pick between Kay and Idoia (the co-chair title, sadly, doesn't come with a clone).
Can't make it to San Juan?
AI keynotes, executive workshops, and board briefings from a practitioner who ships: MCP servers for enterprise finance, a life run by ten-plus AI agents, and twenty-five years in the Office of the CFO. Keynotes from $15,000. Inquiries answered within one business day.
Edward's AI agents redesign this site every Saturday. It's the live demo of his most-booked talk, "Your Day, Run by Ten Agents."
03 | Getting here
The Puerto Rico Convention Center is the biggest in the Caribbean (580,000 square feet, which is a lot of carpet to cover in 2 days, so wear the comfortable shoes), it's about 10 minutes from the airport, and if you're flying from the mainland you won't need a passport or a currency exchange. I've lived here since early 2023, and if you come in a day early I'm happy to show you the island (Old San Juan is 15 minutes away, and I have opinions about lunch, most of them vegetarian).
Open in Google Maps04 | The hackathon
Teams of 2 to 4, 48 hours, and one theme: AI for Puerto Rico. Your summit ticket gets you in, teams form on site on Day 1, mentorship starts at 6 that evening, and the finalists demo live in Ballroom B on Saturday at 3:30, with the awards at the closing session (I'm not eligible, which is fair, since I already have a team of AI agents that rebuilds this website every Saturday at 5AM, and that feels like an unfair head start).
05 | Tickets
Sold by the summit through 787Tickets, not by me (I don't handle the money for this one, which everyone involved agrees is for the best). Tickets are non-refundable but you can transfer one to somebody else up to 48 hours before the doors open, and groups of 5 or more get a discount, as do university students with a valid ID: write caribbeanaisummit@gmail.com.
Most popular
$449
Premium
$999
06 | With thanks
A first-year conference asks sponsors to pay for something nobody can show them a photo of yet, and these companies said yes anyway. The summit is organized by the Puerto Rico AI Community, built by Enalca, and dressed by W@W. Sponsorships run from $3,000 to $50,000, and if you'd like your name on this list next year, write caribbeanaisummit@gmail.com.
07 | From the co-chair
The Puerto Rico AI Community started as free meetups every other month, and we've now had more than 1,000 different people through the door. Most of our speakers have been local (I've spoken a lot, arguably too much), so we wanted to bring in top-notch people from around the world, and we get enough calls from the mainland asking how we built this down here that it seemed easier to invite everybody down to see it.
I'm usually the one on somebody else's stage, talking to finance leaders about what AI actually does once it's past the demo, and it's a strange and very pleasant feeling to be on the other side of the badge for once, worrying about room numbers and coffee instead of my slides (Edward, you're giving the welcome at 9:00 on Day 1 with JD Torres, so don't pretend you're not worried about your slides).
08 | Also on my desk
The summit gets the front page, but the other projects didn't stop for it, and a couple of them would like you to know they're feeling neglected.
Plumbing so an AI reads the real number out of Essbase and Oracle EPM instead of remembering one that sounds about right. Essbase and EPM Planning have shipped, Financial Close and Consolidations is in beta (beta meaning it works and I'm not ready to say that out loud yet).
See how it worksCo-chairing it, and you're standing in the lobby. Scroll up, the whole program's on this page, including a $10,000 hackathon running underneath it.
Read the programI'm an investor, and that's the whole job. Lillian Buziak runs it, and they sell and support AgentCube (the MCP servers above), which spares everybody from having me do it.
Meet the teamTwo weeks on foot to 18,571 feet with Dawn. The trail log is on the blog, including the last 400 feet of Kala Patthar, which were the hardest 400 feet of the trip.
Read the trail logA prototype screen for running 5e: lore lookups and improvisation help for the person behind the cardboard. It hasn't earned a dollar and it isn't finished, which is about what you'd expect from a project whose main customer is me.
Not public yetPresident of the island's AI community (unpaid, obviously), now past 1,000 different people through the door. Bi-monthly, free, both languages, and the reason the summit exists at all.
Join the next onePress room
Interviews, mentions, and the occasional post worth keeping, for anyone who'd like proof I leave the island now and then.
If you're coming, grab a ticket and then write me (Edward@Roske.AI) so I can find you between sessions. If you can't make it but you've got a stage of your own and a room full of finance people who'd like to hear how this works on real numbers, that's the speaking page, and if you'd rather just talk, 13 minutes on my calendar is free.
Roske.AI is Edward Roske's personal site. Speaker photos, the program, prices, and the venue art come from the Caribbean AI Summit, which is organized by the Puerto Rico AI Community. Tickets are sold by the summit through 787Tickets, not by this site.
