Stop doing math, becoming a leader, and the future of AI agents

Former Police Chief Explains What Real Leadership Looks Like w/ Mike Villa @ Port of Seattle

Today on the podcast I have a very unique guest. Mike Villa is not only the Retired Chief of Police at the Port of Seattle Police Department, he is also – unfortunately for him – my Father. Now at the time of this recording Mike was planning to launch his own start up called Villa Consultancy where he would help leaders develop high-functioning teams and successful organizations. I wanted to have him on because that’s such a critical skill for every founder to have. We talk about * The Marine Corps Leadership Mistake That Changed Mike Forever * Why Most Teams Fail: The Dying Art of Followership * The Chief of Police Leadership Lesson Every Startup Founder Needs Mike is retiring from a 36-years in Law Enforcement, where he spent significant time on the SWAT Team at Tukwila and the last 8 years as Chief of Police at the Port of Seattle. I think you guys will really enjoy this one – this is Episode 24 of How NOT to Build. 00:00 — Retirement, Leadership, and What Comes Next 02:07 — Why Most Startups Actually Fail 03:20 — What the Marine Corps Taught Mike About Leadership 06:12 — The Leadership Mistake Mike Made During Desert Storm 09:05 — Why Isolated Teams Eventually Collapse 11:50 — The Dangerous Trap of “My Team vs The Company” 14:58 — The Dying Art of Followership 16:20 — The Easiest Way to Become Your Boss’s Favorite Employee 18:15 — Why Smart Leaders Still Need to Be Followers 20:10 — The Biggest Leadership Mistake Mike Made in 27 Years 23:45 — Why Most Leaders Secretly Crave Credit 25:25 — How Great Teams Handle Conflict and Accountability 29:10 — “You Broke My Trust” — The Conversation Most Leaders Avoid 32:05 — The Brutally Honest Team Exercise Every Company Should Try 36:10 — Becoming Chief During COVID and the Anti-Police Era 38:20 — How Mike Rebuilt Trust From Scratch as Chief of Police 40:00 — Why Leaders Need to Over-Communicate 43:15 — What “Building Relationships” Actually Means 45:05 — The Leadership Comment That Backfired Immediately 49:20 — The Best Leadership Book Mike Ever Read 52:40 — The Team Framework Mike Is Using After Retirement 56:05 — Why No Team Ever Truly “Arrives”

Stop doing math, becoming a leader, and the future of AI agents

On this episode I got to catch up with my long time friend Rob Oesch, the Director of Product Management at Kaseware. In this episode we cover * Why you need to stop doing math with your startup * Practical advice for when you transition into a leadership role on your existing team * And what it’s going to look like when you replace your employees with AI agents At Kaseware, Rob delivers a premier investigative platform for Law Enforcement, Corporate Security, and Intelligence Analysts. I hope you enjoy, Episode 23 of How NOT to Build. 00:00 Introduction to the Podcast and Its Purpose 02:33 The Prototype Mindset and Building Products 05:22 Navigating the Zero to One Challenge 07:45 The Importance of Client Relationships 10:16 Lessons from Leadership and Boundaries 12:49 The Intersection of Law Enforcement and Technology 15:34 Open Source Intelligence and Its Evolution 18:20 Building Products for Niche Markets 20:38 Leadership Styles and Communication 23:19 The Balance of Grace and Decisiveness in Leadership 25:59 Transitioning to Axon and Future Endeavors 30:26 Transitioning to Axon: A New Beginning 31:18 Growth and Scaling: From Zero to One 34:05 Navigating Challenges in a Fast-Paced Environment 36:16 Adapting to Change: Lessons from Government to Tech 38:46 The Side Hustle Mentality: Balancing Passion and Work 41:53 Introducing Kaseware: A New Venture 46:50 Challenges and Opportunities in AI Integration 51:10 The Future of AI in the Workplace 55:58 Reflections on Technology and Human Connection

How We Survived Losing 90% of the Business w/ Saul Bankaitis @ Collinear Group

Today I talk with Saul Bankaitis, CEO of Collinear Group. A little backstory, Collinear Group was the second company I worked at in my professional career. So it was a privilege for me to sit down with him and get his point of view on everything that’s happened over the past several decades of that industry. We cover * His critical advice for anyone thinking about an engineering career * How to the tough politics of struggling companies * And one leadership move that you do not what to undervalue As the President and CEO of Collinear Group, Saul leverages deep expertise in serving commercial clients and government agencies operating at the highest levels of aviation and aerospace. His industry-leading consulting team helps manufacturers, suppliers, and operators reach new heights by bringing intelligence and technology to solve the most complex challenges in aerospace. 00:00 — Introducing Saul 04:10 — What AI Is Doing to the Next Generation of Careers 06:00 — “Do You Even Need to Care About the Code Anymore?” 08:25 — Saul’s First Experience Seeing the SR-71 Blackbird 10:10 — The NASA Job Saul Hated — And Why It Changed Everything 11:55 — The Leadership Culture That Changed Saul’s Career 15:20 — The Biggest Mistake Saul Made at Techtura 18:55 — The Brutal Reality of Not Being Able to Pay Your People 21:05 — Why Most Engineers Struggle to Add Real Value 22:40 — “What’s the Real Requirement?” 25:35 — Why Job Fulfillment Matters More Than Ever 29:55 — How Saul Accidentally Became an Entrepreneur 33:15 — The 95-Hour Weeks That Built Collinear 36:40 — How Collinear Exploded From 2 People to 40 39:10 — The Leadership Lessons Learned During COVID and the MAX Crisis 41:15 — How Collinear Survived Losing 90% of Its Business 43:35 — The Leaders Who Saved the Company 45:20 — Why “Industry 4.0” Was Mostly Hype 47:05 — The Hardest Part of Leading Through Chaos 49:10 — Why Followership Is a Dying Art 50:25 — Saul’s Biggest Leadership Regret 52:05 — The Future of Aerospace, AI, and Advanced Air Mobility 53:35 — Why Remote Work Makes Mentorship Harder 55:10 — The Real Opportunity in Aerospace AI 57:10 — What’s Next for Collinear

The Future of Healthcare: AI Hospitals That Think for Themselves w/ Claus Jensen @ UT Medical Center

On today’s episode, I got the host Claus Jensen the CITO @ the University of Texas Medical Center. We talk about - What if the hospital building itself became part of the medical team? - In an AI-driven world, standardization might actually become suboptimization. - Defensive programming shouldn’t just happen at the code level. It has to happen at the business level. Claus has 2 decades of transformation and technology experience and is currently leading the innovation, technology, automation, and AI elements of establishing a new Academic Medical Center, the first such in the Austin metropolitan area. He’s taking a future backwards approach to what integrated care should look like. Over the next 5 years he plans to grow the Dell Medical School, expand the Research mission and build a new 300 bed specialty hospital. By integrating clinical science, technology, logistics, behavioral science and data science we are creating a differentiated and unique environment and experience, with digital first as a foundational principle. This is episode 21 of How NOT to Build. 00:00 — The Hospital That Thinks for Itself 03:38 — Why Standardization Might Be Killing Innovation 07:58 — Can AI Personalize Hospital Operations in Real Time? 13:40 — From Pigeon Racing Software to the C-Suite 16:50 — The Truck Drivers Who Threatened a 15-Year-Old Programmer 18:20 — What Hasn’t Changed in Tech Since 1982 19:25 — AI Can Build Faster — But Can Humans Keep Up? 20:38 — The AI Model That Learned the Wrong Thing 24:58 — The $738 Billion Bug That Almost Broke a Bank 27:40 — Why Good People Still Make Dangerous Mistakes 28:45 — The Most Important Skill for CTOs and Founders 32:45 — The Leadership Mistake That Changed Claus Jensen’s Career 35:20 — Why Technical Mastery Alone Isn’t Enough 38:05 — How to Separate AI Hype From Real Innovation 40:40 — The Future of Healthcare Isn’t What You Think

Navigating Growth as a Healthcare Startup: A Year in Review w/Greg Prosser from Hansel Medical

In this episode, Dan Villa catches up with Greg Prosser, CEO and founder of Hansel Medical, to reflect on nearly a year of entrepreneurial journey, recent milestones, and strategic pivots. Greg shares insights on fundraising, product development, and balancing the demanding life of a founder in the healthcare tech space. Main Topics: * Greg's recap of Hansel Medical’s progress over the past 11 months, including funding and team growth * The importance of design partnerships and transitioning to early adopters * Pricing models for hardware and SaaS in medical device industries * Leveraging AI and automation to accelerate product engineering and testing * Challenges faced during product iteration, including manual device tagging and sterilization considerations * Personal reflections on work-life balance, mental resilience, and the mindsets of successful founders * The strategic decision to own hardware assets versus leasing or selling equipment * Future outlook, including growth targets, customer acquisition goals, and fundraising plans Chapters: 00:00 Introduction and Housekeeping 01:57 Funding and Team Developments 05:49 Design Partners and Product Development 10:53 Transitioning to Early Adopters 16:10 Pricing Strategy and Market Fit 21:45 AI's Impact on Productivity 27:20 Design and User Experience 31:35 The Evolution of Engineering with AI 33:48 Spec-Driven Design: Bridging Business and Engineering 35:25 Curiosity and Exploration in Product Development 38:02 The Role of Engineers in a Rapidly Changing Landscape 42:18 Learning from Mistakes: Embracing the Journey 49:16 Setting Realistic Goals and Managing Expectations 58:03 Building Relationships and Future Opportunities Resources & Links: Jemini.io [jemini.io] FanBravo - Dan @ Jemini [https://app.fanbravo.com/danjemini] Dan's LinkedIn [https://www.linkedin.com/in/daniel-villa/] Connect with Greg Prosser: Hansel Medical [https://www.hanselmedical.com/] Website Greg's LinkedIn [https://www.linkedin.com/in/gregory-prosser/] Additional Notes: * Greg emphasizes that product market fit is within reach, but strategic pricing and hardware ownership models are crucial for sustainable growth. * The conversation highlights the importance of embracing micro failures as learning opportunities and maintaining mental resilience. * AI's role is seen as a productivity enhancer, yet automation and deterministic code remain vital for scalable, reliable solutions. * The episode closes with Greg inviting potential team members, partners, and investors to connect early and explore meaningful collaboration. ⁠Greg Prosser⁠ [https://www.linkedin.com/in/gregory-prosser/?skipRedirect=true] is the Founder and CEO of Hansel Medical, leading innovation in surgical equipment tracking to help orthopedic distributors and manufacturers save millions by eliminating lost inventory and wasted search time. With a background in engineering and business from the University of Missouri-Columbia, Greg combines technical expertise with strategic leadership to develop cutting-edge solutions for the medical device industry. Intro Music by Eggy Toast