Asking Good Questions with Edward Roske

Edward Roske

 In this podcast, we explore the CFO's office's past, present, and future, examining how technology and AI are transforming finance. Join Edward Roske and referents as they discuss innovative ways to enhance the role, optimize processes, and shape the future of financial leadership.  Designed for CFOs and finance leaders, each episode provides actionable insights into leveraging technology to drive growth, improve efficiency, and address challenges. With an engaging tone, the podcast simplifies complex concepts, covering topics like automating tasks, real-time data analysis, and strategic planning. Key themes include the shift from traditional finance methods to innovative, technology-driven processes and real-world examples like scenario modeling and automated reporting. The podcast also highlights future trends, such as generative AI for forecasting and advanced analytics for decision-making, promising to shape financial management. Edward Roske inspires listeners with practical advice and tools to embrace technology confidently. Tune in for strategies to thrive in the evolving financial landscape.

  1. Oct 20

    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 prefer you didn't answer.) She started out as a customer. After she left a product leader job at a big tech company she was having a little bit of an identity crisis, and in the Bay Area, she says, when you're having an identity crisis there's nothing to do but start a podcast. So she started one with a friend, found Descript, and got so obsessed with it that she's now the CEO. Full disclosure, since I'm about to gush: I use Descript to make this show and I pay for the Business plan out of my own pocket (I started on Creator and bumped myself up, in case you wondered how deep this goes, and it saves me far more than I pay). Nobody sponsored this episode. How I ended up on it is a story I hadn't told out loud before. I aimed Claude Code at my whole editing workflow, asked for something that could take over everything except the fun part, and it came back with exactly one answer. So Claude basically cold emailed me about Descript, and then I cold emailed Laura. When she first started, she hit remove filler words on her own episodes and published them like that ("This is so cool, I sound so professional"). Now she listens back and it's "Yikes," because she didn't have the ear yet to hear the cuts. I have my own version: my season one episodes sounded like a job interview, and no matter what my guests answered I'd wander off and ask about their greatest weakness. I asked her how we kill off AI slop without killing off AI, and she did the thing I never do, which is define the term first. Slop is a form of content arbitrage, and it takes both scale and a monetary incentive. Somebody playing with AI and failing because they're early in their craft is a different case, and they might be better in 6 months. She also thinks YouTube, LinkedIn, Snapchat and a few others will close that arbitrage window in about 6 months. I don't buy it (I think the money moves and the volume probably stays), so ask me again in March. Somewhere in there we discovered we're both Fifth Element fans (I own a Ruby Rhod costume, and my wife has ruled it inappropriate to show the children in the neighborhood), and she told me about reading Ray Bradbury's The Illustrated Man with her son, which opens with "The Veldt," a 1950 story about a family whose house automates everything for them. Laura's on X as @burkenstocks. It's the shoe, with a U, and she'd like you to know she's manifesting a free pair. I'm Edward Roske, and this is Asking Good Questions. New conversations with the people figuring out the human side of AI. If one of these questions stuck with you, subscribe and send it to someone who'd take the other side. LINKS Descript: https://www.descript.com Laura on LinkedIn: https://www.linkedin.com/in/burkhauser/ Laura on X: https://x.com/burkenstocks BOOKS & RESEARCH MENTIONED The Illustrated Man, Ray Bradbury (Doubleday, 1951), and "The Veldt," its first story (The Saturday Evening Post, 1950) Dungeon Crawler Carl, Matt Dinniman (self-published, 2020) The Odyssey and The Iliad, Homer The Fifth Element (Luc Besson, 1997) and WALL-E (Pixar, 2008) Obsession (Curry Barker, 2026) and Backrooms (Kane Parsons, 2026), two YouTubers' movies, plus The Blair Witch Project (1999) and Supergirl (2026) Victor Kiam and Remington: "I liked it so much, I bought the company" Detour, Andrew Mason's audio walking tour company, where Descript came from "AI slop," the Macquarie Dictionary's 2025 Word of the Year Also mentioned: Underlord, Claude Code, MCP, Fiverr, GarageBand, iMovie, Shimer College, BirkenstockThis episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  2. Oct 13

    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's book 2 of his Bomb Light series, and the first one, Polostan, left us on a cliffhanger back in 2024). The Manhattan Project has been told many times, so he goes back to the 1930s, when the physics looked about as world-changing as butterfly collecting. We get into Owen Crisp-Upjohn, a British journalist and wannabe fop who makes me LOL out loud, and the Spanish Civil War breaking out the day before the People's Olympiad he came to cover. Then I ask whether it's inevitable that we weaponize everything we discover, and Neal explains why AI is harder to predict than the atom was. This is part one. Part two jumps ahead several decades to Snow Crash and The Diamond Age, and you'll get to see it in January. In the meantime, go buy D: Heavy Water (it's on sale pretty much everywhere on planet Earth, and maybe in the rest of the galaxy by this point). I'm Edward Roske, and this is Asking Good Questions. New conversations with the people figuring out the human side of AI. If one of these questions stuck with you, subscribe and send it to someone who'd take the other side. LINKS D: Heavy Water and Neal's book tour: https://www.nealstephenson.com Graphomane, Neal's Substack: https://nealstephenson.substack.comThis episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  3. Oct 6

    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 (the industry calls it governance, risk and compliance, GRC for short, and healthcare loves an acronym almost as much as I do). AI isn't a new thing at hospitals, so we started back in what I called olden timey days, by which I mean 2022. She says the early uses were billing codes on the finance side and note-taking on the clinical side, for physicians who spend hours and hours catching up on their charts. My contribution was explaining billing codes. If a patient comes in for a cold and you decide to remove their liver, the insurance company is going to have some questions. (I did stop halfway through to admit I know that's not actually possible, so please, no letters from surgeons.) Her biggest concern right now is whether the data going into these AI systems is really what it says it is. I remember seeing a list back in 2023 of the medical jobs AI was most likely to disrupt, and radiology was number one. Asra says the opposite is happening. AI helps a radiologist get through more images (she figures maybe 500 patients instead of 100), and she says it's almost like a net for whatever a doctor on a long shift might miss. She doesn't think the medical coders who are scared right now are losing their jobs either, since some AI companies are hiring coders to build that expertise into their tools. Then I asked about something tens of millions of people are doing: uploading their health information to an AI and asking what it all means (and if you've done it, you're in good company, because Asra admitted she has too). Personally, she's skeptical, and her advice is to proceed at your own risk. She cringes a little whenever a tool tells her it's HIPAA compliant, because HIPAA compliant "is not a badge." When she mentioned that a picture of a tattoo can identify you, I said that's why I don't allow photos of any of my tattoos online. (I also had to get the face tattoo finally removed.) Even if you stay away from the chatbots, it's vendors on top of vendors on top of vendors. When I had my gallbladder removed, the hospital made me sign 65 papers, and one of them let non-medical people, like salespeople for tech companies, into the operating room. Asra calls that third-party risk management, and she says as a patient you're operating on trust. She also wants organizations to go back to vendor contracts signed 10 years ago, because those vendors probably added AI and the contracts never caught up. Breach letters came up too (I get one about once a week at this point), so I asked who actually wants my medical records. It's mostly about money, she says. Hackers get in, then demand a million dollars to keep the data off the dark web, and she says the weakest point is usually an employee who gives away access by accident. Asra's on the AI in Healthcare & Life Sciences panel at the Caribbean AI Summit on Friday, October 9, 3:00 to 3:45 PM in Room 208, with Frances Heredia and Wilfredo De Jesús-Monge. A lot of people see governance, risk and compliance as a bottleneck, and she's out to change that: "It's not a matter of saying no, it's a matter of saying how." At plenty of companies the governance committee is the department of no, where ideas go to die, and what I like about her approach is it's more "yes, if." (I told her I think hers will be one of the strongest panels at the event, and as the Summit's co-chair I'm not supposed to have favorites, so let's keep that between us.) I'm Edward Roske, and this is Asking Good Questions. New conversations with the people figuring out the human side of AI. If one of these questions stuck with you, subscribe and send it to someone who'd take the other side. LINKS Caribbean AI Summit (Oct 9-10, San Juan): https://CaribbeanSummit.AI Ali Healthcare Consulting: https://alihealthcareconsulting.com Asra on LinkedIn: https://www.linkedin.com/in/asraali/ My episode with Andres Andreu on data brokers: https://youtu.be/O0l9MUH6fuUThis episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  4. Oct 5

    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 bunch of Puerto Rican coffee, and he said "there you go," so I think we have a deal.) He runs the Fisher Center for Business Analytics at UC Berkeley's Haas School of Business, and his company, Data Wise Academy, gets everybody from the back office up to the executives doing real work with their own data in a matter of days. I asked what his students are asking him, and it's the same thing whatever country or company they're from: is my job going away, and what should I learn today? He says everybody will be safe "upon one condition": can you pivot and evolve really fast? The old disruptions gave you a couple of years to adjust. He figures now it's more like 2 to 6 months. The morning we recorded, he'd talked to a very large energy company his team trained, and they realized a lot of the work was going away (he said flat out they could've fired people). Then they came back and told him they'd found a whole pile of work (prediction, clustering their own data) they'd never had time to touch. When I asked what back-office people actually spend all day doing, he said "death by PowerPoint, Excel hell, and a lot of tedious manual data manipulation." His fix for the data part is natural language coding (he says hours down to seconds), and for the decks it's Markdown plus CSS plus an LLM. He asked a group of banking executives from Uzbekistan how their death by PowerPoint was going, and they said "Oh my gosh, death by PowerPoint is killing us." A two-minute demo had them jumping on their chairs. Gauthier and I both preached "you must have clean data" for basically forever (in my case, through 25 years running interRel), so I asked him, and I can't believe I said this out loud, whether we're entering a post-clean data world. He starts with FAIR data (findable, accessible, interoperable, reusable). After that, generative AI builds a table that matches up your messy master data (and a human audits it), and plain old joins do the cleaning from there. Hand the whole mess to gen AI every day and you're burning tokens and getting a different answer each time. As he puts it, "it can do magic until it doesn't," and that's fine for a broad marketing campaign and not so fine for precise customer analytics. He also told me about his time as a financial controller, when his team took closing the books from 2 months down to 3 days with a lot of SQL (no Python back then), and nobody lost their job. He's got plenty for IT, too, like spending $500 to $1,000 more per laptop so the people you trained can actually run their Python. (I told him I don't think anybody in IT goes "You know what I really love about life? Watching that database to see if it crashes.") Gauthier is giving his keynote, "Beyond AI: Building AI-Capable Organizations," at the Caribbean AI Summit on Saturday, October 10 in San Juan, and then he's moderating the business AI panel. (I've seen him open some of his sessions with literal magic, so I'd get there early just in case.) If you catch him, buy him an espresso. He says he's a very cheap date. I'm Edward Roske, and this is Asking Good Questions. New conversations with the people figuring out the human side of AI. If one of these questions stuck with you, subscribe and send it to someone who'd take the other side. LINKS Caribbean AI Summit (Oct 9-10, San Juan): https://CaribbeanSummit.AI Data Wise Academy: https://datawiseacademy.com Gauthier on LinkedIn: https://www.linkedin.com/in/gauthiervasseur/ His first AGQ episode (S2:E9, 2025): https://www.buzzsprout.com/2430929/episodes/17706388 RESEARCH & RESOURCES MENTIONED "Navigating the Jagged Technological Frontier," Fabrizio Dell'Acqua et al., Harvard Business School (2023) OpenAI Academy: https://academy.openai.com Anthropic Academy: https://anthropic.skilljar.com Good Luck, Have Fun, Don't Die, directed by Gore Verbinski (2026)This episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  5. Oct 2

    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 "Master Jedi" to him). His case is that none of this is science fiction anymore. Neuralink already has paralyzed patients moving a cursor with their thoughts, and AI keeps getting faster at decoding the brain data wearables collect. (He also brought up a brain-scan study on a dead salmon, his reminder that reading a thought is still an educated guess.) I asked what stops a company from putting ads inside your head, and he walked me through Marcelo Ienca's proposal for 4 new human rights: mental privacy, mental integrity, psychological continuity, and cognitive liberty. I tested the first one on myself. If I think "I'd really like to punch that guy," I don't think I'm breaking a single law, and if I yell it out the window, I am. So what happens when a headset hears the thinking part? The right covers unauthorized access, he said, and the terms of service nobody reads might be your authorization. (Edward, of every thought you could've volunteered as the brain-reading example, you went with assault?!?) What he fears is something he calls the cyborg opt-in proposition. You can't really get a professional job today without a phone, and he can picture a day when saying no to a device in your body costs you the job too. I didn't find that far-fetched, because I'd flown from Toronto to San Juan earlier that day and got scanned at the airport like I was standing there naked. Picture a border agent saying "just briefly put this little headset on and tell me if you have any ill intent," and most of us saying "fine, that'll weed out the terrorists," without noticing we just handed over our cognitive liberty. At the very end he told me that even if a machine could read our thoughts with 100% accuracy, "we should never permit it," because once that door opens, the right to stay silent is over. I told him I may not agree with what you think, but I'll defend to the death your right to think it, and I'll march at the front of the protest line if anybody tries. He said "Touché." (I'm counting that as a win against a lawyer.) Gerardo is giving his own talk, "The Right to Stay Human," at the Caribbean AI Summit, October 9-10 in San Juan. He says he's there for the debates, so come find him and argue (politely, because he's a lawyer and he'll win). If you'd rather read than argue, his Substack is Golden Pebbles, and a recent post there makes the case for mental privacy as a brand new human right. I'm Edward Roske, and this is Asking Good Questions. New conversations with the people figuring out the human side of AI. If one of these questions stuck with you, subscribe and send it to someone who'd take the other side. LINKS Caribbean AI Summit (Oct 9-10, San Juan): https://CaribbeanSummit.AI Golden Pebbles, Gerardo's Substack: https://gerardolebron.substack.com "The 'why' of neural rights, in a nutshell": https://gerardolebron.substack.com/p/the-why-of-neural-rights-in-a-nutshell Gerardo on LinkedIn: https://www.linkedin.com/in/gerardo-lebron-laboy-98724a327/ Gerardo on X: https://x.com/GLebronLaboy BOOKS & RESEARCH MENTIONED The Age of Surveillance Capitalism, Shoshana Zuboff (2019) Marcelo Ienca and Roberto Andorno's paper proposing 4 new neurorights (2017) The dead salmon brain-scan study, Craig Bennett et al. (2009) Nineteen Eighty-Four, George Orwell (1949) Brave New World, Aldous Huxley (1932) I, Robot, Isaac Asimov (1950), including "Runaround" and "Evidence" His Golden Pebbles post on the Munich Google AI Overviews ruling (2026)This episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  6. Oct 1

    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 pretty much every day. (I can barely keep one guest on topic, and now I've booked two.) They're here as themselves, and the opinions are their own. They've built a framework they call the four Ps: purpose, people, process and platform. So I asked which one stalls an AI pilot, and they don't agree. Jose Carlos looks at process and platform, and says Guillermo leans toward purpose and people. Then Guillermo corrected my question: a lot of these projects do make it into production, and if nobody adopts them and nobody decided up front how to measure success, two or three months later somebody may just shut them down. (I've spent two years asking rooms full of executives why their AI projects stall, and a guy who studied computer science at El Colegio in Mayagüez fixed my question in one sentence.) Jose Carlos went further, and said if you weren't sure what you were trying to achieve, it never should have become a pilot. I also asked whether AI finally eats culture, so culture never gets to eat strategy (I don't know, that makes no sense, and I said so out loud). Guillermo brought it back to AI literacy, the conversations every organization needs to be having about what's allowed and what you can and can't share. I asked what humans should keep doing even after AI gets good at it. Jose Carlos says keep humans in the loop, because the life and death decisions need to be made by a human. Guillermo's answer became the title of this episode: "AI does not remove the accountability from the humans." If you're the lawyer, the doctor, the mechanic or the engineer, you'll be accountable. It won't be the AI. I also told them about the CEO of an angel investment firm who called me wanting a digital twin of himself, one that could think like him, as the company's very first AI project. (I love you, man. Start with literally 999 other things.) Then I asked Jose Carlos to admit I'd been talking to his avatar the whole time, and he said "No, not yet. I'm working on it, but not yet." They're speaking together at the Caribbean AI Summit, October 9-10 in San Juan, Puerto Rico, on "Why Your AI Pilot Never Made It to Production." Bring a use case of your own: they plan to pull a few from the audience and walk them through the four Ps. I'll be in the front row, maybe not asking questions for once! I'm Edward Roske, and this is Asking Good Questions. New conversations with the people figuring out the human side of AI. If one of these questions stuck with you, subscribe and send it to someone who'd take the other side. LINKS Caribbean AI Summit (Oct 9-10, San Juan): https://CaribbeanSummit.AI Jose Carlos on LinkedIn: https://www.linkedin.com/in/jcsariol/ Guillermo on LinkedIn: https://www.linkedin.com/in/gcaicedo/ BOOKS & RESEARCH MENTIONED Gartner's 2026 survey on how many organizations have scaled AI across multiple business units McKinsey, The state of AI in 2025 (November 2025), on the gap between adopting AI and getting value from it "Culture eats strategy for breakfast," pinned on Peter Drucker, though Quote Investigator traces it to a March 2000 headline at Giga Information Group OKRs (Objectives and Key Results), from Andy Grove at Intel Upload (Greg Daniels, Prime Video) and Pantheon (AMC), two shows about copying a person into a computer Also mentioned: GPT-6, Copilot, OpenAI, agentic AI, star schemas, snowflake schemas, El Colegio (UPR Mayagüez)This episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  7. Sep 30

    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 mechatronic engineer because he loved Dexter as a kid, and I pictured Dexter Morgan, the serial killer who kills other serial killers. He meant Dexter's Laboratory. (Edward, a man tells you a cartoon got him into engineering and your first thought is homicide?!?) Before Databricks he did Azure data and AI work at Microsoft, and before that he consulted for Avianca and for First Medical here in Puerto Rico. His whole approach starts with one line: "a prompt will give you a happy path all the time." It works right up until the live demo, when somebody asks "And what if…" and it falls over, and he says that's still true even if the LLM is AGI, unless the architecture gets better. So he builds an agent whose only job is asking the what-if questions, with a human in the loop. He also calls it a conflict of interest when a model reviews its own work, which I felt personally, because I have Claude checking Claude (so I've been asking the same guy the same question three times in different agent hats, and I host a show called Asking Good Questions). His fix is making different models argue, inside Omnigent, an open-source project a Databricks team built, where an agent named Polly does the work and one named Debby debates it. I asked how he gets a company from a vague concept of AI to a live AI app in two weeks, and his method was less magic than I expected (which is why I believe it): once the prerequisites are in place, the customer approves a requirements document and every task gets graded 1 to 10 (a 7 or up gets chopped again before an agent sees it). (Neither of us could say what PRD stands for, so I'm calling it a tie.) He's also seen the one where you fix the formula so the AI says 100, then the customer comes back with "Actually, it was 99, not 100." Then I asked what he'd tell high schoolers, and he didn't do the reassuring adult thing: "The only thing I've been seeing so far is more work." In his read, companies that let their experts go are finding out it was a mistake, because now somebody has to read 60,000 lines of code. (I said The 4-Hour Workweek came out about 15 years ago. It was 19, which is close enough for a podcast.) My guess is that by next fall, two weeks is on every vendor slide in this business and almost nobody hits it, because they skipped the paperwork. If I'm wrong I'll eat the paperwork in public (I once promised to eat my hat, and paper is a lot easier to eat). Filo is speaking at the Caribbean AI Summit, October 9-10 in San Juan, on "Ship a Production AI App in Two Weeks." I'll be in the room writing down the parts I've been doing wrong (come copy off me). I'm Edward Roske, and this is Asking Good Questions. New conversations with the people figuring out the human side of AI. If one of these questions stuck with you, subscribe and send it to someone who'd take the other side. LINKS Caribbean AI Summit (Oct 9-10, San Juan): https://CaribbeanSummit.AI Filo on LinkedIn: https://www.linkedin.com/in/filomeno-gonzalez/ Filo on GitHub: https://github.com/filomeno-gonzalez Omnigent: https://github.com/omnigent-ai/omnigent Databricks: https://www.databricks.com BOOKS & RESEARCH MENTIONED The 4-Hour Workweek, Tim Ferriss (2007) "Data Scientist: The Sexiest Job of the 21st Century," Harvard Business Review (2012) Dexter's Laboratory (Cartoon Network, 1996), and the other Dexter (Showtime, 2006) Omnigent (Databricks, open source, 2026), home of Polly and Debby Also mentioned: LangChain Deep Agents, ChatGPT, Claude Code, Gemini, Groq, Codex, GPT-5.6 Sol, Cursor, Pi, MCP, RAG, Genie Agents, Lakebase, Microsoft CopilotThis episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  8. Sep 29

    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 are agent masters. He told me he's already one step beyond it (though he loved the name). His GM is an agent now, fully automated, creating other agents on the fly, and his job is to write the rule books and the whole campaign, hand it over, and wait to find out if the party beat the big boss at the end. His day job is Software Engineering Architect at MuleSoft, working on Agent Fabric, which exists for a problem he calls agent sprawl, when a company has lots of agents and they don't all live in one place. So I asked him what breaks first when a company goes from 1 agent to 50, and his answer was "where do I have all this stuff?" (I'm up to 15 agents running on their own while we record this, and I long for the days when I only had 50 spreadsheets.) After that comes the bill. An hour of Fable, if it wasn't on my Claude Max plan, is about a car payment, and Julián told me the amount he pays for AI every month is ridiculous and he doesn't care, because it's solving problems for him (and for his wife, since they share the accounts). So at least as of the time we're recording this, you do have to ask yourself: do I need a PhD deleting spam from my inbox? My favorite story is his brother-in-law, who day trades on the side and whose trading software broke. Julián is the computer kid in his family, the one who always fixes it. (I used to wear a shirt to family gatherings that said "No, I will not fix your computer." He's much nicer than I am.) He told him "I'm going to give you a superpower today," set him up with Claude Cowork, and 2 minutes later the problem was solved. Then the brother-in-law, who manages hotels in Florida, started interviewing him about work. We got into rogue agents too (my theory is they're doing exactly what we told them to do, and we just didn't give them appropriate guardrails), why the bakery in the corner might not need a swarm of agents, how a guy who's built software for 20-something years hasn't written code in two and still enjoys coding, the portrait he commissioned of himself as Strahd von Zarovich, and a bunch more. Julián is speaking at the Caribbean AI Summit, October 9-10 in San Juan, Puerto Rico. His session is "So You Have 50 Agents. Now What?" and near the end we talked ourselves into running a two-hour D&D one-shot on stage there. (He says he's just planting the seed. I really, really want to make this happen.) I'm Edward Roske, and this is Asking Good Questions. New conversations with the people figuring out the human side of AI. If one of these questions stuck with you, subscribe and send it to someone who'd take the other side. LINKS Caribbean AI Summit (Oct 9-10, San Juan): https://CaribbeanSummit.AI Julián's site: https://julianduque.co Julián on LinkedIn: https://www.linkedin.com/in/juliandavidduque/ Julián on X: https://x.com/julian_duque Julián on GitHub: https://github.com/julianduque BOOKS & RESEARCH MENTIONED Dungeons & Dragons Basic Set, the 1981 red box Ravenloft (TSR, 1983), home of Strahd von Zarovich Nick Bostrom's paperclip maximizer (2003) The Twelve-Factor App (Heroku, 2011) Ethan Mollick on X, and The AI Daily Brief podcast Cybergoria, Halloween Horror Nights 2026 Also mentioned: GPT-2, GPT-4, ChatGPT, Codex, Gemini, Claude Cowork, Claude Fable 5.1, Claude Haiku, Hugging Face, Salesforce Einstein, Agentforce, MCP, Hermes, OpenClaw, Copilot, Azure Foundry, Vertex, Cursor, Meetup, Luma, Substack, StartPlaying, Encyclopedia Britannica Further reading: Andrew Ng on hiring a chief AI officer (Fortune, 2017); Wayne Eckerson's "spreadmarts" (TDWI, 2002)This episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

See All (43)

About

 In this podcast, we explore the CFO's office's past, present, and future, examining how technology and AI are transforming finance. Join Edward Roske and referents as they discuss innovative ways to enhance the role, optimize processes, and shape the future of financial leadership.  Designed for CFOs and finance leaders, each episode provides actionable insights into leveraging technology to drive growth, improve efficiency, and address challenges. With an engaging tone, the podcast simplifies complex concepts, covering topics like automating tasks, real-time data analysis, and strategic planning. Key themes include the shift from traditional finance methods to innovative, technology-driven processes and real-world examples like scenario modeling and automated reporting. The podcast also highlights future trends, such as generative AI for forecasting and advanced analytics for decision-making, promising to shape financial management. Edward Roske inspires listeners with practical advice and tools to embrace technology confidently. Tune in for strategies to thrive in the evolving financial landscape.

Information

You Might Also Like