
Hosted by Mateo Bervejillo · EN

Today’s episode is a special one. It’s not often that you get to sit down with someone who has operated at the highest levels of public-sector technology, advised global organizations on the future of innovation, and brought that experience into the classroom and onto the page as a professor and author. That’s why it’s truly an honor to welcome Jonathan Reichental to the show. Jonathan served as CIO for the City of Palo Alto, right in the heart of Silicon Valley, where he helped transform how a city can use technology to better serve its residents, from open data initiatives to digital services that made government more accessible, transparent, and responsive. Since then, through his advisory work and founding Human Future, he’s continued to help cities, governments, and organizations think more boldly, and more practically, about how emerging technologies can improve real lives. What makes Jonathan’s perspective so powerful is the unique combination he brings: hands-on experience inside government, deep roots in the tech industry, and the reflective lens of a professor and author who studies leadership, innovation, and the future of cities. He doesn’t just talk about what’s possible, he understands what’s workable. In this conversation, we’re exploring a critical question: How can cities and governments actually use technology to serve people better? Enjoy!

Today we’re joined by a guest who’s built his career at the intersection of Latin American entrepreneurship, tech, and global opportunity, Matias Barbero. Matias is an entrepreneur, investor, and ecosystem builder. He is the Founder of 401, a Miami-based platform investing in bold ideas and venture funds, accelerating high-potential startups, and connecting Latin America with the U.S. through a strong cross-border community of founders, investors, and operators. His work is all about connecting ecosystems, building bridges, and unlocking opportunities, especially between Latin America and the U.S., whether that’s through mentorship, investment, community programming, or hands-on operational leadership. In this episode, we’ll dive into Matias’s journey: what he’s doing today, the reasons he believes Latin American founders should think globally, especially toward the U.S., and whether there’s truly something special about the bond between these regions.

The way we discover, consume, and trust news is changing faster than at any point in modern history. Audiences are no longer loyal to platforms, distribution is no longer owned, and technology, especially AI, is reshaping not just how content is delivered, but how media organizations think about their very purpose and sustainability.Today’s guest sits right at the intersection of media, technology, and strategy. Allison McHenry is a seasoned media and tech leader who has spent her career helping news organizations navigate digital transformation, audience strategy, and the hard business questions that come with building sustainable, mission-driven media in a fragmented world.In this conversation we will talk about how people are actually consuming news today and how distribution strategies are being rethought from the ground up, through the lens of Allison's story and experience as a Technology and Product Leader in this space. This is a thoughtful, honest conversation about the future of news, and what it will take to build media organizations that truly serve people in the years ahead.

My guest today is Bobby Tahir, a highly experienced CTO and technology executive with a track record of building, scaling, and modernizing engineering organizations in high-growth and private equity–backed companies.In this conversation, we unpack what really changes for a CTO the moment private equity enters the picture: the shift in expectations, the compressed timelines for value creation, and the strategic mistakes that can quietly derail even strong technical leaders. Bobby shares what PE-backed CTOs often underestimate, and what the best ones do differently when the pressure is on.We also dig into how AI is reshaping the CTO role in very real ways. Not the hype, but how it actually changes where a CTO spends their time, which teams feel the impact most, and where productivity gains are truly showing up versus being oversold.And finally, we get into people leadership, specifically the hard realities of leading distributed and outsourced engineering teams across cultures and geographies. Bobby offers a grounded take on what great leadership looks like today when teams may never share the same room, but standards still can’t slip.If you’re a CTO, a technical leader, or anyone navigating scale under pressure, this one’s for you.Bobby, thank you so much for being here!

Today’s guest lives right at the intersection where strategy, technology, and organizational reality collide.Noureddine Oirkha is a Strategy & Transformation Director at Deloitte, where he works with large, complex organizations on some of their most ambitious, and most risky, initiatives: digital transformations, global ERP implementations, and enterprise-wide change programs. This is the kind of work where decisions ripple across thousands of people, dozens of systems, and years of execution.In this conversation, we will unpack what digital transformation really means when you strip away the marketing language, why so many large ERP and transformation programs struggle or fail, and why process, discipline, and fundamentals matter just as much as vision and outcomes. If you’ve ever wondered why transformation is so hard, why it fails so often, or how to do it with more honesty and rigor, this is a conversation you won’t want to miss.

Today’s guest has lived through several major waves of technology, and helped shape a few of them along the way. Rupen Chanda is currently the CTO at Bluescape, and over the years he’s held senior engineering and product leadership roles at companies like Adobe and BlackBerry, working at the intersection of platforms, collaboration, and large-scale technology change.In this conversation, we go beyond titles and talk about the inflection points that shaped Rupen’s career, how mindset plays a role in navigating uncertainty, and what it’s really like to lead teams through constant technological disruption. We’ll dive deep into AI, how Rupen sees it transforming the tech industry over the next decade, how he’s applying it in practice at Bluescape, and what concepts like “Industry 5.0” mean when theory meets reality.We’ll also explore what this rapid pace of change means for education, careers, and personal growth, and why human qualities still matter deeply in an AI-driven world. And to round things out, we’ll step away from the keyboard and talk about how Rupen recharges, stays inspired, and keeps perspective outside of tech.Enjoy!