Tools for Tech Leaders

Deb Liu spent years pitching Facebook Marketplace before anyone would greenlight it. When it finally launched, it took multiple failed versions before reaching a billion users. That arc — patient conviction, rapid testing, willingness to be wrong — is the throughline of everything she shares in this episode. From her time building payments at PayPal and ads at Facebook to leading Ancestry as CEO,...

Eric Ries, creator of the Lean Startup methodology and founder of the Long-Term Stock Exchange, has spent 15 years helping companies build products — and watching those companies get quietly hollowed out. His new book, Incorruptible, is a response to what he's seen: mission-driven companies that get taken over by the gravitational pull of shareholder primacy, one compromise at a time. In this epis...

AI transformation is stalling inside most organizations, not because of the technology, but because of leadership. Charlene Li, strategist and author of Winning with AI, shares why giving employees access to AI tools without training or protected practice time creates the illusion of progress while leaving most people behind. She introduces the concept of AI fluency, knowing how, when, and when no...

Dave Kroetsch, founder of Aeryon Labs (acquired for $200M), reveals counterintuitive lessons from building a drone company that faced 17 business red flags—from government sales and hardware complexity to export restrictions and international regulations. Despite knowing none of this at the start, his team built a defensible business serving national security customers worldwide. Learn why drones...

Most leadership challenges aren't actually about strategy or execution—they're about emotion regulation. Executive coach Ed Batista, who has conducted nearly 10,000 coaching sessions over two decades at Stanford GSB, reveals why mastering your emotional responses is the meta-skill that determines leadership effectiveness. Drawing from extensive work with founder CEOs and tech executives, Ed explai...

Real estate investing attracts tech entrepreneurs seeking diversified income, but most underestimate the operational complexity. Dupree of Woodbine Development Corporation reveals the economic fundamentals that separate successful hotel investments from expensive mistakes to brand selection and partnership structures. He shares why his company transformed hiring practices to prioritize cultural fi...

Shopify VP of Engineering Farhan Thawar reveals how to build and scale high-performance engineering teams in the age of AI. Drawing from his experience managing over 1,000 engineers remotely, Farhan shares Shopify's unique approach to weekly demos over burndown charts, their controversial decision to hire 1,000 interns in 2025, and why they're moving back to a monorepo architecture. Learn how Shop...

Serial entrepreneur Rajat Suri, who co-founded Zimride/Lyft and took Presto public, shares hard-won lessons from 20 years of scaling companies. Discover how he completely changed his career trajectory from wanting to be a doctor to entrepreneurship, why technical founders must branch out beyond engineering, and the surprising origin story of ride-sharing that started with a lonely drive in a famil...

Every AI guardrail gets broken, but that's not the real problem. Cybersecurity framework creator Sounil Yu reveals why traditional security approaches fail in the knowledge age and how enterprise AI deployments create dangerous "oversharing" vulnerabilities that most organizations don't even recognize. Learn the DIKW pyramid framework for understanding AI risks, discover why your security team's "...

Michael Seibel, partner emeritus at Y Combinator, reveals how founders can thrive in the rapidly changing AI landscape by discarding outdated assumptions and embracing new possibilities. Drawing from his experience supporting thousands of startups, Seibel explains why traditional office hours remain critical for redirecting founder focus and unlocking transformative insights. He shares compelling...

Digital infrastructure is at a critical turning point. Kris Lovejoy, security & resiliency global practice leader at Kyndryl, reveals why organizations must fundamentally reimagine their approach to security in an era of unprecedented volatility. Discover why some financial institutions are reversing course from public cloud, how European technology sovereignty efforts are reshaping global tech st...

HR executive Melanie Hughes reveals why most leaders fail at creating lasting cultural change by focusing on what's urgent instead of what's important.  Drawing from 20+ years of experience at startups and Fortune 500 companies, she shares practical frameworks for developing high-potential talent, making strategic decisions that stick, and implementing just enough structure to accelerate growth wi...

MIT Principal Research Scientist Dr. Keri Pearlson reveals why traditional cybersecurity approaches fail and how organizations can build true cyber resilience beyond technical solutions. Drawing from her extensive research with Fortune 500 companies and government agencies, she shares practical frameworks for creating a security-conscious culture, conducting effective tabletop exercises, and rebui...

Bob van Lujit, CEO of vector database pioneer Weaviate, reveals how technical founders can successfully transition to effective business leaders by mastering three core responsibilities: articulating vision, building exceptional teams, and securing funding. Bob shares his counterintuitive approach to customer-centricity through "empathy" rather than "obsession," and explains how young founders bri...

Your customer success strategy might be creating more problems than it solves.  Customer success veteran Pete Oelschlaeger, who has led CS teams at Tanium, Contrast Security, and now Ambient AI, reveals why traditional organizational structures create dangerous blind spots where customer issues fall through the cracks.  Learn how to identify when your organization is just talking about customer-ce...

Former Indiegogo CEO Becky Center shares hard-earned lessons from her journey through Groupon's hypergrowth, her transition to first-time CEO, and her experience leading teams through modern tech's most pressing challenges.  Gain practical frameworks for avoiding the "hobby role" trap, leveraging remote work to level the leadership playing field, and building powerful alumni networks that strength...

Meirav Oren, co-founder and chairwoman of Versatile, left Intel to build a company that's transforming the construction industry through data-driven innovation. Crane-mounted sensor and vision systems are revolutionizing  job site safety and efficiency, while delivering pivotal insights on operational success. Meirav delves into practical leadership tools and frameworks, "open by default" communic...

Can you teach plants to communicate? In this episode, hear about Shely Aronov's journey, CEO of InnerPlant, from launching a food brand to creating biotech crops that send signals about their stress and health to farmers. Shely shares lessons on leadership, the pivotal role of strategy, and the evolving hiring needs of startups—from scrappy generalists to industry experts. Discover how InnerPlant...

In this episode, Dr. Carole Robin, renowned for leading Stanford's famous "Interpersonal Dynamics" course, shares powerful insights on building exceptional relationships in tech leadership. Known as the "Queen of Touchy Feely," Dr. Robin breaks down why interpersonal skills are often more challenging—and more crucial—than technical expertise in building successful organizations. The conversation o...

Ian sits down with Nick Halla, a pioneering farmer/engineer-turned-entrepreneur who helped build the groundbreaking company Impossible Foods from the ground up. Nick shares fascinating insights from his journey starting as a "croissant engineer" at General Mills to becoming the first employee at Impossible Foods, where he worked alongside founder Pat Brown for 11 years to revolutionize the food in...

In this episode of Tools for Tech Leaders, Ian sits down with Oscar, Emmy, and Peabody-winning filmmaker Bill Guttentag to explore the art of drawing out meaningful stories and insights from leaders. Bill shares his experience conducting compelling interviews, sharing techniques to help create the right environment to ask questions that reveal genuine, illustrative moments. They discuss how his wo...

Ian sits down with ex-McKinsey Executive Coach Jess Yuen to explore critical leadership topics including performance management, strategic thinking, and coaching. Drawing from her extensive experience as a former Chief People Officer and McKinsey consultant, Jess breaks down multiple approaches to executive coaching, shares frameworks for giving effective feedback, and discusses how to handle both...

Jerry Perullo, former Chief Information Security Officer at Intercontinental Exchange and the New York Stock Exchange, shares invaluable insights from his extensive career in cybersecurity, including his experiences at Silicon Valley Bank and his current venture, Adversarial Risk Management. Jerry offered practical advice on conducting effective red team exercises, managing critical infrastructure...

Zack Urlocker, a seasoned tech executive with an impressive track record at companies like MySQL, Zendesk, and Duo Security, shares his invaluable insights from his journey scaling businesses from early-stage startups to industry leaders. This episode explores the evolution of open source business models, the challenges of rapid growth in SaaS companies, and the critical importance of prioritizing...

In this episode of Tools for Tech Leaders, Ian speaks with Mark Leslie, the founding CEO of Veritas Software and a legendary figure in Silicon Valley. Mark shares invaluable insights from his remarkable journey scaling Veritas from a $64 million valuation at IPO to over $64 billion. The conversation delves into Mark's strategic approach to business transformation, his philosophy on leadership and...