The Deep Dive Lab

Monica has spent 20+ years leading talent and innovation at companies like Google, Goldman Sachs, EY, and Bank of America. Today she’s the founder of FlipWork, where she helps Fortune 500 companies reinvent how humans and AI work together. We talk about: • Why AI adoption is the biggest barrier to ROI• The shift from operators to orchestrators of AI agents• How to find your “zone of genius” and de...

Victoria is the founder and CEO of the Silicon Valley Executive Academy and has spent decades working inside the heart of the tech ecosystem. She explains the four core principles that drive innovation in Silicon Valley: • Ecosystem density• Risk tolerance• Bias toward action• Collaborative networks We also discuss how AI will reshape industries and why many companies are approaching AI the wrong...

News today often feels less like information and more like noise. In this episode of The Deep Dive Lab, I sit down with Kira Shishkin, founder of informed.now, a startup rethinking how people consume news in an age of misinformation, clickbait, and attention overload. Instead of opinion-driven media, informed.now delivers a daily SMS summarizing the most important global events using primary sourc...

Myles Harrison, Principal at Praktikai and founder of Machine Learning Toronto (MLTO) joins the show to cut through the hype and share a pragmatic playbook for real-world AI. We unpack why the “boring” stuff (clean data, operational BI, and simple automation) often delivers far more value than flashy agent demos, how to manage change in large organizations, and when voice AI actually makes sense....

On this episode of The Deep Dive Lab I talk with Andy Sitison, CTO at Share More Stories, about one core question: how do we turn human stories and emotions into useful, trustworthy data? We cover: How to prompt people so they actually tell meaningful stories (the “story journey”) The logic of breaking a story into expressions and scoring emotions (joy, anxiety, belonging, and more) A real project...

What if the key to solving some of tech's biggest problems has been overlooked because of outdated hiring practices? My guest is Tara May, CEO of Aspiritech , a multi-million dollar tech services company with one incredible stat: her entire team is made up of 100% autistic talent. We explore how autistic talent is solving big tech problems for clients like Bose and the TSA: Building Smarter AI...

On this episode I speak with Prof. Dr. Dennis-Kenji Kipker, Research Director & Founder of the cyberintelligence.institute and serves on the Federal Parliament, about why we need to think beyond “cybersecurity” and build true digital resilience . We cover: what digital resilience actually is and how it changes procurement and policy. why trustworthiness, software bills of materials (SBOMs) and...

Jeff Lawy (Head of Deep Tech Commercialization, Ashera Health) joins me to explore how AI is transforming blood testing, from a handful of biomarkers to 10,000+ signals that actually help you act. We talk about turning complex lab data into clear, personalized guidance, building guardrails around LLMs, and why women’s health (fertility, perimenopause, menopause) is the smartest first focus. We als...

It’s refreshing talking to creatives who also gets the technical bits - Nick was one of them! Nick Cawthon’s spent 20+ years in UX, spoken at Google, Stanford, Xerox PARC, teaches data science students (and Design Strategy MBA programs etc), and runs his own consulting agency. He strongly believes that it’s not about replacing people with AI but rather “retraining”. With his programs, he also teac...

Stephen Sakach, CEO & founder of Zero company, >70k on his mailing list, coined BLISS: Build Love into Scalable Systems. His idea: random acts of kindness —> predictable, repeatable systems that drive both customer loyalty and internal cohesion. He believes businesses that lead with purpose and empathy are the ones that last. Empathy isn’t just a nice-to-have*.* It’s a proven growth driv...

I thought sustainability meant choosing between profit and “doing good for the planet”. My chat with Josh proved me WRONG. “Stop selling sustainability. Start selling something BETTER that happens to be sustainable.” A bit about Josh Dorfman: CEO of Supercool, co-founded Plantd (a manufacturer of carbon-negative building materials) with ex-Tesla employees named Fast Company’s 2024 Most Innovative...

Eli Portnoy (with $66M in exits) taught me the importance of REALLY listening to your customers. TLDR from his chat: Listen to what customers actually mean - during COVID, his customers asked to stop payments, but Instead, he asked: “how do we make sure we're giving them enough value that they wanna pay us?”. He pivoted, new product gained traction which led to acquisition (full story on the p...

If you’re pressing "00000" to escape the bot, that's not user error - that's design failure. And it may be why people think AI chatbots suck (I don’t). Most bots are built backwards. Companies think "how can we handle more customers with less staff?" Instead of "how can we actually improve customer experience”. In this episode, I sat down with AI conversational tec...

We sit down with Amir Kiani — a PhD in Mathematical Philosophy and Logic, and a senior analyst in the healthcare industry — to unpack one of the biggest questions in tech and philosophy: Can AI truly be conscious? Here we dig into what consciousness really means — beyond the buzzwords. We explore how subjective experience is defined in humans and whether AI systems like LLMs (Large Language Models...

Flora Fertility: The First Individual Fertility Insurance for Women One in five women will need fertility treatments—but who’s paying for it? Meet Dr. Christy Lane and Laura McDonald , co-founders of Flora Fertility , the first-ever individually owned fertility insurance. They’re tackling the financial gap in reproductive healthcare, giving women the power to plan on their own terms. We dive into...

Startups fail fast. But what if you could test an idea even faster—before spending months (or years) building the wrong thing? David Hirschfeld has built and sold companies, helped 70+ startups, and developed Launch First , a way to validate ideas before writing a single line of code. We talk about: The biggest mistake founders make How to sell an idea before building it Why startups fail (and how...

In this episode, we sit down with Amir Feizpour , founder of Aggregate Intellect , to explore the future of work with AI agents and humans. Topics include: The rise of AI copilots and their role in transforming workflows. How human creativity complements machine efficiency through exploration and exploitation. The potential for single-person startups powered by AI agent ecosystems. Insights into l...

Today, we’re sitting down with Sundar Narayanan, an AI ethicist who’s on a mission to make sure technology doesn’t just work for us but works ethically for future generations too. Sundar dives into the tough questions around AI—like balancing innovation with responsibility—and why embedding ethics in tech early on is crucial. But here’s the thing: Sundar isn’t just about AI. He’s fascinated by eve...

In this episode, we sit down with Akash Shetty, the founder of Publicus, an AI startup that aims to bridge the gap between people and government using advanced AI systems. Akash, who also happens to be an ultra-endurance athlete, dives deep into the potential of AI agents to transform everything from content creation to complex decision-making. We discuss the evolving role of AI in productivity an...

Ever wondered if AI could help detect mental health issues like anxiety or cognitive decline before they become serious problems? In this episode, we sit down with Marija Stanojevic , a machine learning researcher with a decade of experience working at the intersection of AI and healthcare. Marija shares how her work is helping to revolutionize mental health treatment by using AI to find patterns...

This week I had the pleasure to chat with Jo Peterson, a tech powerhouse discussing about cloud, cyber security and diversity.  A little about Jo Peterson : Top Cloud Influence: Jo is recognized as a Top Cloud Influencer by Onalytica, “a major player in the cloud arena” by Silicon Republic Business Leadership: As the Vice President of Cloud and Security Services at Clarify360, Jo crafts solutions...

In this episode, we dive deep into the exciting world of healthcare and technology with Rachel Barker, the Program Director at SE Health.  Join us as we explore how AI is revolutionizing healthcare, making doctors' lives easier, and enhancing patient experiences.  Discover the balance between technology and the human touch, the skills needed in this evolving field, and the surprising ways AI...

This week, we're delving into the world of government issues and the exciting realm of gov tech, where technology becomes the catalyst for solving crucial public problems. Join me, along with the brilliant Madison Dias, GovTech & SaaS Leader and Vice President of Sales at Envisio. Together, we'll explore his remarkable experiences in overcoming major challenges, such as policy work a...

This week, I'm joined by Beth Nuniam, the esteemed Management Consulting Manager at KPMG Canada. Get ready to unlock the secrets of becoming a top-tier problem solver as Beth shares her invaluable experiences and expertise. Throughout the conversation, we'll delve into the intricacies of the healthcare industry, and Beth will provide exclusive insider information on its future. This is y...

In this episode, we explore Glenn Poulos' journey from being a civil servant to becoming a successful businessman. Glenn has experienced two successful exits by building two companies from scratch and is recognized as an award-winning author for his book titled "Never Sit in the Lobby".  Whether you're in sales, or in any field, it can always be helpful to learn how to sell an...