Content

Everything I Make

Video briefs, blog posts, and podcast episodes. Less formal than a book. More useful than a tweet.

01

Videos

Monthly AI news briefs, plus a back catalog of Essbase and EPM how-tos (the Look Smarter Than You Are series, for the calc-script crowd).

OpenAI's ChatGPT Graders Got Fired for Using ChatGPT

OpenAI's ChatGPT Graders Got Fired for Using ChatGPT

OpenAI pays contractors to read real prompts that real people typed into ChatGPT and grade the answers on a one-to-seven scale. 404 Media reported that some of them got fired for using AI to do the grading. The giveaways were repetitive words, work that came back too fast, and...

Oct 23, 2026
DraftKings Built an AI to Find Its Biggest Losers

DraftKings Built an AI to Find Its Biggest Losers

The New York Times reported that DraftKings built a machine learning model in 2023 scoring every customer on how much they'd lose, then DraftKings aimed about $400 million in bonus bets at the highest scorers in 2025. A former analyst says the profile it finds is a problem...

Oct 21, 2026
An AI Is Editing This Episode | Laura Burkhauser

An AI Is Editing This Episode | Laura Burkhauser

Laura Burkhauser is the CEO of Descript, and about 6 minutes in she told me she's a terrible creator. Her words: "Let it be said that I am a terrible creator. I couldn't make it." (If the CEO of the creator software is a terrible creator, I'm not sure what that makes me, and I'd...

Oct 20, 2026
Amazon Is Buying Up to $8 Billion of Backup Generators

Amazon Is Buying Up to $8 Billion of Backup Generators

Amazon agreed to buy up to $8 billion of backup generators from Generac for its data centers, and Generac's stock jumped as much as 45%. Generac's entire 2025 revenue was $4.21 billion, so one customer signed up for about two years of the whole company. Along with the order...

Oct 19, 2026
Why Is Google Letting Its Engineers Use Claude?

Why Is Google Letting Its Engineers Use Claude?

Google blocked most of its employees from using outside AI coding tools, Claude Code and OpenAI's Codex included. Business Insider reported that Google then gave all of its engineers access to Anthropic's Claude Opus 5, with a per-person quota, and said Gemini is still its...

Oct 17, 2026
If They Don't, Somebody Else Will | Neal Stephenson

If They Don't, Somebody Else Will | Neal Stephenson

In October of 1939 the physicists just stopped publishing. I asked Neal Stephenson where AI research is on that timeline, and he asked how we'd even know if a lab went dark.

Oct 13, 2026
MIT's 95% AI Failure Stat Was About Custom Builds

MIT's 95% AI Failure Stat Was About Custom Builds

The famous MIT report says 95% of company AI projects return nothing. Page six of the same report says 4 out of 5 companies that piloted a ChatGPT-type tool got it working; the 95% belongs to custom builds. When I'm the one signing the check I time the tool with a stopwatch...

Oct 11, 2026
Humans Started Saying "Delve" Out Loud After ChatGPT

Humans Started Saying "Delve" Out Loud After ChatGPT

Max Planck researchers found people started saying "delve" and "meticulous" out loud after 2022. We caught it from the machine, and the machine has since dropped the word. The real tells are structure: lists of three, the long dash, "experts argue," the summary sentence closing...

Oct 8, 2026
02

Blog

Thoughts on AI, agents, and whatever else is worth the keystrokes.

If You Can Read Every Line of an AI's Code, Do You Understand It?

An AI rebuilds my website every Saturday at 5AM and the source is public, so you can see everything. I can read every line and still can't tell you why it made the choices it made, and Google says 75% of its new code is AI-generated now, so I'm in large company.

AIAgentsLeadership

What Happens When AI Finds the Bug First?

AI found a flaw in PHP that had sat unnoticed for more than a decade, and on Wednesday governments started taking their own websites offline. I had an agent check my own sites in about 15 minutes. Your IT team may need longer.

AISecurityAgents

Is Your AI Pilot Stuck in Training Mode?

Every fighting game has a Training Mode where the dummy stands still and never hits back. Most enterprise AI pilots are fought there, and that's why so many of them 'succeed' right up until the first real month-end close.

AIFinanceLeadership

How Many Fire Extinguishers Does an AI Summit Need?

The first Caribbean AI Summit is in the books: 800+ people from 17 countries, 44 speakers, 2 batucadas, a healthcare hackathon, and 6 fire extinguishers Dawn bought at Walmart at 7:30 in the morning.

AIConferencePuerto Rico

What Do the WEF, MIT, and the EU Parliament Actually Disagree About on AI?

The Caribbean AI Summit puts the World Economic Forum's former Head of AI, MIT's Senseable City Lab, and the EU Parliament's AI advisor in one building in San Juan. Here's where I think they'll disagree.

AIConferencePuerto Rico

How Do You Judge an AI?

A county fair posts its scoring rubric before the first jar of jam comes through the door, and the judge writes down exactly why you lost. Most AI pilots get a slide that says 'success.' So this week I entered my own work in the fair.

AIAsking Good QuestionsState Fair

Is a Good Puzzle the Same Thing as a Good Question?

Dawn and I have each done a bit over 300 escape rooms. This week I turned the home page into one, and you're locked in with a machine that answers exactly what you asked. There's a hint button.

AIAsking Good QuestionsEscape Rooms

The $3 Million IP Address

How I took down the largest pager company's busiest call center with one IP address in 1997, and what the CFO said when the bill came due.

StoriesTech HistoryConsulting
03

Asking Good Questions

A show about the human side of AI, with guests from all over the world.

Asking Good Questions started because I noticed that the best finance leaders I've worked with across 25+ years all had one thing in common: they asked better questions than everyone else in the room.

Season 1 was mostly CFOs, Season 2 was AI and finance, and Season 3 is about the human side of AI (turns out the rest of humanity has questions too). Either way, I'm trying to figure out what's actually working and what's still hype (and I'm not selling you software while I do it).

Oct 20, 2026 51 min

An AI Is Editing This Episode | Laura Burkhauser

Laura Burkhauser is the CEO of Descript, and about 6 minutes in she told me she's a terrible creator. Her words: "Let it be said that I am a terrible creator. I couldn't make it." (If the CEO of the creator software is a terrible creator, I'm not sure what that makes me, and I'd

Oct 13, 2026 27 min

If They Don't, Somebody Else Will | Neal Stephenson

In October of 1939 the physicists just stopped publishing. I asked Neal Stephenson where AI research is on that timeline, and he asked how we'd even know if a lab went dark.Neal wrote Snow Crash, The Diamond Age, Cryptonomicon and Anathem, and his new novel, D: Heavy Water, is out now (it'

Oct 6, 2026 56 min

You're Literally Operating on Trust | Asra Ali

Asra Ali has spent nearly two decades in healthcare compliance and privacy, and she's the founder and principal consultant of Ali Healthcare Consulting here in San Juan. When a hospital or a health tech company wants AI anywhere near patient data, she's the one checking what could go wrong

Oct 5, 2026 52 min

Everybody Will Be Safe (on one condition) | Gauthier Vasseur

Fun fact: Gauthier Vasseur is the first returning guest I've ever had on Asking Good Questions. We finished Season 1 with 38 subscribers (not a joke), the channel is over half a million now, and I told him on camera he might've had something to do with that. (My plan to pay him back is a b

Oct 2, 2026 61 min

Who Owns the Inside of Your Head? | Gerardo Lebrón Laboy

Gerardo Lebrón Laboy calls himself a robotics, AI, and brain-computer interface lawyer. He's taught Robot Law at 2 law schools here in Puerto Rico, and his master's in law and technology at the University of Ottawa had Isaac Asimov on the reading list (thanks to his teacher Ian Kerr, still

Oct 1, 2026 48 min

AI Does Not Remove Accountability From Humans | Sariol + Caicedo

This is the first time I've had two guests on at once, and I did it on purpose. Jose Carlos Sariol and Guillermo Caicedo both work at Microsoft, helping companies across Central America and the Caribbean get AI past the great demo and into something people actually use, and they work together p

Sep 30, 2026 50 min

The Only Thing I've Been Seeing Is More Work | Filo Gonzalez

Filo Gonzalez is a forward deployed engineer at Databricks, which means he gets in the room right after somebody sees a slide and says "I want this to happen," and then he makes the slide real (inside companies big enough that the governance team has its own governance team). He trained as a mechatr

Sep 29, 2026 66 min

Do I Need a PhD Deleting Spam From My Inbox? | Julián Duque

Julián Duque has been playing Dungeons & Dragons since he was 7 (early '90s for him, 1981 for me, so yes, I'm slightly older), and he's a dungeon master too, so a few minutes into a conversation about AI agents I pioneered a term right there on the call: we are not dungeon masters, we

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04

Interviews

Interviews (sometimes I'm asking, sometimes answering), conference talks, and a few webinars from across the web.

Jun 1, 2026

EPM Coffee Chat Episode 16: AI in EPM with Edward Roske

Long-form coffee chat with the Toronto EPM User Group crew (Arun, Azmat, Fred, and Harsh) on AI in EPM: what gets automated first, how planning shifts from human-first to computer-first, and why knowing when a number is wrong still beats producing it fast. Some Oracle roadmap talk too (Autonomous Database, MCP, Essbase), plus a straight answer on what AI means for entry-level finance jobs.

Toronto EPM User Group
May 15, 2026

Lost His Dad at 27, Then Built a Billion-Dollar Company

Long-form sit-down with Crystal Bai on losing my father at 27, founding interRel two months later, and the 25 years between that decision and merging with Keste to help found Argano. Some grief, some accidental career advice, and a fair amount about why founder companies and family companies are not as different as people pretend.

Dead Serious / Renidy
Apr 16, 2026

Edward Roske Interviews Paul Lepine of Grant Thornton at Kscope25

From the ODTUG podcast booth at Kscope25 in Grapevine in The Great State of Texas. Edward sits down with Paul Lepine, Grant Thornton's Alliance Director for Oracle and NetSuite across North America, with 15+ years inside Oracle before that.

ODTUG / Kscope25
Mar 26, 2026

Edward Roske Interviews Tim Tow of Applied OLAP at Kscope25

From the ODTUG podcast booth at Kscope25 in Grapevine in The Great State of Texas. Edward sits down with Tim Tow, founder and president of Applied OLAP, creator of Dodeca, and the first Oracle ACE Director in the Hyperion / Essbase community.

ODTUG / Kscope25
Mar 26, 2026

Edward Roske Interviews the Accordion Crew at Kscope25

From the ODTUG podcast booth at Kscope25 in Grapevine in The Great State of Texas. Edward sits down with the crew from Accordion, the private-equity-focused financial consulting firm with a major Oracle EPM practice (and the team that absorbed Platform Specialists in 2024).

ODTUG / Kscope25
Mar 26, 2026

Edward Roske Interviews the Infosys Team at Kscope25

From the ODTUG podcast booth at Kscope25 in Grapevine in The Great State of Texas. Edward sits down with the Infosys team on Oracle Cloud, EPM, and what the partner ecosystem looks like at global scale.

ODTUG / Kscope25
Mar 26, 2026

Edward Roske Interviews Abhi Nerurkar of EPMware at Kscope25

From the ODTUG podcast booth at Kscope25 in Grapevine in The Great State of Texas. Edward sits down with Abhi Nerurkar of EPMware, a recent Kscope speaker on enterprise master data and Oracle PCMCS integrations.

ODTUG / Kscope25
Mar 26, 2026

Edward Roske Interviews Charlie Yousef of Version 1 at Kscope25

From the ODTUG podcast booth at Kscope25 in Grapevine in The Great State of Texas. Edward sits down with Charlie Yousef of Version 1, the global Apex and Oracle consultancy.

ODTUG / Kscope25