Where's Waldo (Edward Edition)?

Few people (my wife and kids included) tend to know what I’m doing at any given point. I always know (or pretend to know) what I’m doing, so it doesn’t occur to me to tell everyone else. So let me give anyone who cares a quick catch up. Suffice to say, it all falls under the banner of trying to leave the world a smarter place than I found it, but if you are one of the (rare few) who want the details, keep reading.

We’ll start with this specific moment. This week, I’m launching Season 3 of my “Asking Good Questions” podcast. Well, it’s more of a video interview show these days because the video side gets far more viewers than the audio/podcast version. I’m balancing this with helping grow the Puerto Rico AI Community (I live in PR), co-chairing the Caribbean AI Summit, traveling to crazy places with my wife (for instance, we did a 2-week hike to Everest Base Camp earlier this year), speaking at events all around the world, investing in companies doing cool things in AI, inventing some AI products here and there, and playing/running D&D (Dungeons & Dragons) with my sons whenever I scrounge up some free time. (Well yes, I do have an official “Nerd Club Founding Member” card; why ask do you, young Padawan?)

The Asking Good Questions show has changed a lot and not just in a subscriber count way (from 38 subscribers in Season 1 to now over 400,000 subscribers to my @Roske-AI YouTube channel). Back in 2024, Season 1 was mostly me interviewing CFOs on where they’ve been, what they’re seeing, and where finance is going (which often turned to AI). Season 2 was more about me interviewing interesting people that sat at the intersection of AI & Finance: so some CFO’s but also people who happened to be at the center of how much AI was changing the world.

Season 3 (at least through the 7 episodes we’ve filmed so far) is about the human side of AI: how do we evolve in the AI era but also maintain what makes humans human? This season also has me interviewing a lot more people from around the world: business, academia, non-profits, really just anywhere there’s a thought leader trying to understand what it means to be human in an AI world. (The production value has also gone up a bunch since that first adorable/embarrassing episode back in 2024, in case you haven’t checked it out lately.) Season 3 Episode 1 (s3e1 to the cool kids) is out and I think you might enjoy it. Watch it and let me know what you think.

I’ve also started adding a lot more daily shorter content (which is what most subscribers are probably there to see) under the “Asking Good Questions” banner on the YouTube channel. It started by me asking a question each day about some AI story I saw on the news or about something I was wondering about in AI. My top posts tend to be when I recap the monthly AI news (I watch all the news so you can avoid it!) but sometimes a random post goes viral. My quick shorts on “How is AI Used at the World Cup?” and “Is Elon Musk the Richest Person Ever?” have all gone beyond my traditional “AI and Business” crowd. (Boy will they be disappointed by the rest of the content on the channel.)

I’m also working with a great group of people here in Puerto Rico (where I’ve lived since early 2023) to build the Puerto Rico AI Community. We meet bi-monthly and we’ve now had over 1,000 different people attend one of our meetups. We actually get calls from the mainland asking us how to build an AI community in their city like we have down here on our beautiful island in the Caribbean. We’ve formed a non-profit (PRAIC) and it now takes a decently large team to handle all our educational and networking events. If you haven’t checked out the AI crowd in Puerto Rico, you’re missing something. We have great speakers and it’s all free.

Most of the PRAIC speakers have been local to our community (I’ve spoken a lot… arguably too much) but we wanted to bring in top-notch speakers from around the world, so we’re now hosting a big conference on October 9-10, 2026 at the Puerto Rico Convention Center called the “Caribbean AI Summit”. We have speakers & thought leaders from around the world from the business side (Microsoft, Salesforce, Snowflake, DataBricks, Kroger, Amazon, HP Enterprise, and a bunch more) and the academic side (including AI professors from M.I.T., UC Berkeley, Southern Methodist University, Carnegie Mellon, and Penn).

All together, we have more than 30 speakers across 3 different tracks. If you haven’t been to Puerto Rico before and you’re looking for an excuse, you can’t beat coming down and learning everything about AI in two jammed pack days (CaribbeanSummit.AI). All sessions are simultaneously translated between English and Spanish, so pick your favorite language and join us. I’m happy to show you around the island if you come in early.

On yet another AI front, I had fun coding a product that lets any AI (ChatGPT, Claude, Gemini, Copilot, you name it) talk to both Essbase and Oracle EPM. (Edward, you’ve already established your nerd cred, and now “you had fun coding”?!? You should be Mayor of Nerdtown by now.) It not only lets you query cubes in natural language, it puts an end to LLM’s deciding that they can’t get access to real data, so they might as well make it up.

If you haven’t seen it, it’s called AgentCube and is being sold & supported by the awesome people over at Caprus AI (Caprus.AI). Their CEO is Lillian Buziak (her pic from Kscope2026 is below along with two amazing former interRelites, Terrance D. Walker, PMP & Glen Chang). DM Lillian on LinkedIn and insist that “Edward said you’ll give me a good price on AgentCube” (so now you got that goin’ for you, which is nice). I’m pretty proud of AgentCube, so check it out if you’ve got Essbase, Planning, or Consolidations.

What else is going on that you might find interesting (and I can’t believe you’re still reading at this point, you glutton for punishment)… oh, I launched a personal website (Roske.AI) so in the future you won’t have to guess what I’m doing. I had fun building the site because it literally completely changes every Saturday morning at 5AM to go along with whatever pop culture thing is distracting me that week. At the moment, it’s got me starring in my own version of The Odyssey and despite my (all mental) bubble muscles, I’m no Matt Damon. But check it out if you want to be amused at my expense. (As the old adage goes, if you can’t laugh at yourself, laugh at Edward.)

So in short (…um, should have led with that, Edward, and just cut out everything else cause damn, son, you need an editor especially for your run-on parenthetical asides that no one reads because lets face it, you’ve never met a tangent you didn’t want to go on, but I digress…), I’m spending my time with intelligent people doing cool and interesting things. Some of those people will change the world directly and others will educate those who will directly change the world. I hope to interview them either way, so I can be firmly on the educator side myself.

Miss you all. Come visit me. Or write me (Edward@Roske.AI), which is kinda the same thing.