Modern CTO

It’s about time for the next age of human flourishing. Will AI get us there? Today, we're talking to Zack Kass, author and former OpenAI Go-to-Market Lead. We discuss why AI will likely cure cancer before autonomous vehicles dominate our roads, how mid-market and family-owned businesses can survive the AI consolidation wave, and why the future of AI is invisible infrastructure rather than apps. All of this right here, right now, on the Modern CTO Podcast! To learn more about Zack Kass, check out his website here. To learn more about Zack's latest venture, Korza, check out their website here.

Ready for a brand new show? Today, in a special episode, we're talking about OpenAI shutting down Sora and what it means for the future of AI-generated video. We discuss why consumer demand wasn't enough to keep Sora alive, how AI-generated content is fueling a misinformation crisis on social media, and why the rise of fake digital content might actually push us back toward valuing in-person connection. Make sure to subscribe to Tech in the Morning on YouTube: https://www.youtube.com/@techinthemorning

THIS is how you know you’re not really ready for primetime. Today, we're bringing you our most timeless advice from our last conversation with Alan Williamson, Author of Think Like a CTO. We discuss why most first-time CTOs struggle to communicate with non-technical executives, how to think about budgeting and engineering costs like a true technology leader, and why the ability to articulate a clear vision is what separates a real CTO from a CTO in name only. All of this right here, right now, on the Modern CTO Podcast! To learn more about Alan Williamson, check out his website here.

It’s not just the bad guys who need to hide anymore. Today, we're talking to Guy Kawasaki, legendary Apple evangelist and Chief Evangelist at Canva. We discuss why everybody has something to hide in the digital age, how metadata reveals far more than most people realize, and why Signal is the most practical step you can take to protect your privacy and security right now. Email Guy at [email protected] for a free copy of the book! All of this right here, right now, on the Modern CTO Podcast! To learn more about Guy's latest book, check it out here.

AI tools are more powerful than ever, but you still can’t operate like THIS. Today, we're talking to Stephen Poletto, Field CTO at Span. We discuss why engineering teams are making decisions based on hype instead of data, how AI is reshaping software development through emerging practices like harness engineering, and why measuring actual productivity versus perceived productivity is more critical than ever. All of this right here, right now, on the Modern CTO Podcast! To learn more about Span, check out their website here.

Things are changing faster than ever, but don’t let it affect your team. Today, we're talking to Ashley Goodall, leadership expert and bestselling author. We discuss why the management obsession with change is harming the people it's meant to help, how constant reorganization leads to learned helplessness and quiet quitting, and why the real goal should never be just change. All of this right here, right now, on the Modern CTO Podcast!

What if green technology was actually just more profitable? Today, we're talking to Tom Chi, Google X Co-Founder and Founding Partner at At One Ventures, about his new bestselling book, Climate Capital. We discuss why the physical world is a more predictable investment than software, how his firm identifies the 30 industries responsible for over 90% of planetary damage, and why making clean technology the most profitable technology is the only climate strategy that actually scales. All of this right here, right now, on the Modern CTO Podcast! To learn more about At One Ventures, check out their website here.

From chip design at Bell Laboratories to…the world's #1 Venn diagram comedian?? Today, we're talking to Don McMillan, comedian and former chip designer at Bell Laboratories. We discuss how burning out in Silicon Valley led him to pursue stand-up comedy full time, why having an engineering mindset made him a better comedian, and how a random radio caller unknowingly changed the entire trajectory of his life. All of this right here, right now, on the Modern CTO Podcast! To learn more about Don and his tour schedule, check out his website here

The best managers are the ones who never wanted the job. Today, we're talking to Rajeev Rajan, CTO at Atlassian. We discuss why developer joy outperforms productivity as an engineering goal, how the best managers are the ones who never wanted the job, and why every leadership playbook you've built stops working the moment your team grows. All of this right here, right now, on the Modern CTO Podcast! To learn more about Atlassian, check out their website here.

The biggest lie we were ever sold: hard work alone gets you the promotion. Today, we're talking to Rob Kalwarowsky, bestselling author and leadership coach. We discuss why writing down your goal increases the probability of achieving it to 43%, how the people above you can't promote you for a job you've never told them you want, and why working hard and letting the results speak for themselves is the biggest lie you've ever been taught. All of this right here, right now, on the Modern CTO Podcast! To learn more about Rob's work, check out his website here.

Before you open another Google Docs, you need to hear this episode. Today, we're talking to Anand Narasimhan, CTO at S Docs. We discuss why organizations pay $94,000 in compliance penalties due to documentation errors, how 57% of employees bypass official tools when under deadline pressure, and why automation must come before autonomous AI in enterprise workflows. All of this right here, right now, on the Modern CTO Podcast! Thank you to S-Docs for sponsoring this episode. To learn more, check out their website here.

This theory explains how AI agents can make promises and build trust… with other agents. Today, we're talking to Doctor Mark Burgess, the originator of Promise Theory, and Tony Davis, Senior Director of Agentic Strategy at A&I Solutions. We discuss why command-and-control fails with autonomous AI agents, how agents respond to peer rejection instead of human disapproval, and why Promise Theory is the backbone of governing agentic workforces. All of this right here, right now, on the Modern CTO Podcast! Thank you to A&I Solutions for sponsoring this episode. To learn more, check out their website her

Why did he set off the code-red alarm at his company? Today, we're talking to Wade Foster, co-founder and CEO of Zapier and host of the Agents of Scale podcast. We discuss how Zapier scaled to $5 billion with only one funding round, why 100% of new hires must be AI fluent, and how top companies are using hackathons to transform their organizations in the age of AI. All of this right here, right now, on the Modern CTO Podcast! To learn more about Zapier, check out their website here.

The man behind NVIDIA is unlike any other leader today. Today, we're talking to Stephen Witt, author of The Thinking Machine. We discuss how he lied his way into six interviews with Jensen Huang, why NVIDIA operates like a company that's thirty days from bankruptcy despite being worth trillions, and how Jensen's decade-long bet on the $0 market created the backbone of the AI revolution. All of this right here, right now, on the Modern CTO Podcast! To learn more about Stephen Witt and to buy his book, check out his website here.

He’s seeing AI unfold at one of the oldest financial firms in the world. Today, we're talking to Kevin Adams, CIO at Edward Jones. We discuss how AI is disrupting traditional organizational structures, why humans need to move up the stack while AI handles execution, and how to implement AI at the right speed in highly regulated industries. All of this right here, right now, on the Modern CTO Podcast! To learn more about Edward Jones, check out their website here.

How is a travel giant like Booking.com leveraging AI? Today, we're talking to Vipul Hingne, interim CTO at Booking.com. We discuss how AI is transforming the entire travel experience beyond just planning trips, why Booking.com launched their AI trip planner in just 14 weeks with OpenAI, and how two-thirds of their organization is already using GenAI to solve real customer problems. All of this right here, right now, on the Modern CTO Podcast! To learn more about Booking.com, check out their website here.

AI is flooding the cybersecurity space. So, how do we fight back? Today, we're talking to Ariful Huq, co-founder at Exaforce. We discuss how to build AI defense systems against AI-powered attack waves, why 98% of security alerts are false positives, and how to turn a team of three analysts into a team of ten using AI agents. All of this right here, right now, on the Modern CTO Podcast! To learn more about Exaforce, check out their website here.

If it’s growing exponentially, what will happen to the SaaS model? Today, we're talking to Rob Woollen, Co-founder at Sigma Computing, and Marwan Mattar, VP of AI at Sigma. We discuss whether AI will kill the SaaS industry, why the demo-to-production gap is AI's biggest challenge, and how the cost of building custom applications is approaching zero. All of this right here, right now, on the Modern CTO Podcast! To learn more about Sigma, check out their website here.

He went to the biggest tech and economic gatherings in the world. Today, we're talking to Jim Harris, AI Strategist and Keynote Speaker. We discuss how companies are achieving 80%+ efficiency gains with AI-first thinking, why most employees still fear AI and what to do about it, and how humanoid robots and AI are revolutionizing everything from healthcare to housework. All of this right here, right now, on the Modern CTO Podcast! Jim's website: https://www.jimharris.com/ Jim's YouTube video: https://www.youtube.com/watch?v=zmyTJVWyQJI

If you don’t use it, you lose it. Does the same apply to AI and our brains? Today, we're talking to Jacob Ward, journalist, AI ethics and safety advisor, and author of The Loop. We discuss why AI will dissolve our brains just like Google Maps dissolved our sense of direction, how our unconscious decision-making makes us vulnerable to AI manipulation, and why kids saying "clankers" might be our best hope for the future. All of this right here, right now, on the Modern CTO Podcast! To learn more about Jacob's work, check out his website h

The culture is turning on billionaires, but who do you think is funding our technological progress? Today, we're talking to John McGinnis, Professor at Northwestern University and author of "Why Democracy Needs the Rich." We discuss why wealthy individuals are essential to technological progress and democracy, how professional influencers create incentive structures against the rich, and why America's AI dominance depends on venture capital and entrepreneurial coordination. All of this right here, right now, on the Modern CTO Podcast! To pick up a copy of "Why Democracy Needs the Rich," check it out here!

How should you respond to the fastest shift in tech we've ever seen? Make more mistakes. Today, we're talking to Andrea Iorio, author of Between You and AI and former Chief Digital Officer at L'Oréal. We discuss why asking better questions matters more than having all the answers, how reverse mentoring can transform organizational learning, and why becoming antifragile through smart mistakes is the key to thriving alongside AI. All of this right here, right now, on the Modern CTO Podcast! To pick up a copy of "Between You and AI," check it out here!

THIS is how you keep your infrastructure costs from spiraling out of control. Today, we're talking to Albert Strasheim, CTO at Rippling. We discuss the cost crisis facing CTOs in the age of AI, how he reduced infrastructure costs by 30% while growing traffic by 25%, and why holding back feedback is actually the most selfish thing a leader can do. All of this right here, right now, on the Modern CTO Podcast! To learn more about Rippling, check out their website here.

Has AI really become THIS powerful in the enterprise? Today, we're talking to Brian Elliott, CEO at Blitzy and Tom Jackson, CTO at RSM US LLP. We discuss how AI agents are autonomously completing months of development work in days, why organizational change management is now the biggest bottleneck in software development, and how enterprises are achieving 5x engineering velocity with agentic SDLC platforms. All of this right here, right now, on the Modern CTO Podcast! To learn more about Blitzy, check out their website here.

This was the most useful, actionable advice we got on AI in 2025. Today, we're compiling the best AI content we got from our Modern CTO of 2025: Rob Duffy, CTO at HealthEdge. We discuss why AI demos aren't translating to production ROI, how to treat AI migration with the same rigor as cloud migration, and why technical leaders must use AI tools themselves to drive organizational transformation. All of this right here, right now, on the Modern CTO Podcast! To learn more about HealthEdge, check out their website here.

Most people know booking.com. Almost nobody knows about the $100B+ travel empire behind it. Today, we're talking to Rob Ransom, Senior Vice President at Booking Holdings, about the business strategy behind booking.com, KAYAK, OpenTable, and more. We discuss how AI is transforming travel booking like mobile did a decade ago, why the best strategies prioritize simplicity over complexity, and how booking.com's legendary A/B testing culture removes politics from product decisions. All of this right here, right now, on the Modern CTO Podcast! To learn more about Booking Holdings, check out their website here.