Asking Good Questions with 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.
Asking Good Questions with Edward Roske
With AI, the Winners Will Be the Small Companies | Juan Carlos Pedreira
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
He'd know: he co-founded the Social Business Hub, a digital consultancy in San Juan, and for 15-plus years he's been dragging traditional media companies (Teleonce, Spanish Broadcasting System, Telecinco, and others) into the digital age, and now the AI one. He advises businesses across Puerto Rico, the Dominican Republic, Costa Rica, and Panama, so he sees who's moving and who's stuck. And right now he's running a project where four people do work that used to take five or ten.
We get into the two kinds of workers showing up inside every company: the rogue AI person with all the tools, and the one still feeding the fax machine. His dad's IBM XT makes an appearance, along with the accountant who went from "I lost my job" to all in, which Juan Carlos says is happening again right now at super hyper speed.
Also in here: why AI belongs with the CEO instead of the IT department, what happens when 800 or 900 million people get handed a very powerful tool without instructions (his numbers), the client Excel report that took a full day and now takes minutes, and my confession that I've got fourteen agents running right now, and that managing them has somehow become a 24/7 job (they do not sleep, which sounded like a feature when I set them up).
His two-year prediction: the gap between small and big gets wider, driven by upstarts completely off the radar. I think we're not far from the first one-person billion-dollar company. At one point I told him I had about 45 follow-up questions and genuinely didn't know which one to ask first. Come see which one I picked.
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.
Juan Carlos speaks at the Caribbean AI Summit this October in San Juan. His talk: "AI for Humans: How a Small Business Can Now Out-Compete a Fortune 500 Without Hiring a Single Engineer." Come find us: CaribbeanSummit.AI
LINKS
Caribbean AI Summit (Juan Carlos speaks, Oct 9-10): https://CaribbeanSummit.AI
Social Business Hub (SBH Digital), Juan Carlos's consultancy: https://sbhdigital.com
Juan Carlos on LinkedIn: https://www.linkedin.com/in/juancpedreira/
Juan Carlos on X: https://x.com/juancpedreira (on air he calls X his "social media drug")
BOOKS & RESEARCH MENTIONED
The PR Digital Trends Study 2026 (Estudios Tecnicos + the SME Digital & Innovation Forum, May 2026), the study Juan Carlos cites: https://newsismybusiness.com/puerto-rico-digital-media-use-hits-95-in-2026-study/
"The AI Daily Brief" with Nathaniel Whittemore, the daily AI podcast Edward listens to every day (he blends the name to "the AI Daily Breakdown" on air; this is the real show): https://aidailybrief.ai
Anthropic's AI courses (where Juan Carlos points business owners who ask him where to start)
Also mentioned: Claude, Claude Code, and Claude Cowork; MCP connectors; QuickBooks; Shopify; LinkedIn Learning; Coursera
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.
