How NOT To Build: Startup Stories | A Jemini Podcast

Dan Villa
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  • Entrepreneurship
  • Updated Weekly

"How NOT to Build" is about uncovering the lessons Founders, CTOs, Tech Leads, and Team Leads wish they’d known earlier. I hope these stories spark ideas, offer guidance, and help you navigate your journey to turning vision into reality.

  1. Jun 16

    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 ForeverWhy Most Teams Fail: The Dying Art of FollowershipThe Chief of Police Leadership Lesson Every Startup Founder NeedsMike 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”

    58 min

  2. Jun 9

    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 startupPractical advice for when you transition into a leadership role on your existing teamAnd what it’s going to look like when you replace your employees with AI agentsAt 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

    1h 1m

  3. Jun 2

    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 careerHow to the tough politics of struggling companiesAnd one leadership move that you do not what to undervalueAs 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

    59 min

  4. May 26

    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

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

    Apr 14

    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 growthThe importance of design partnerships and transitioning to early adoptersPricing models for hardware and SaaS in medical device industriesLeveraging AI and automation to accelerate product engineering and testingChallenges faced during product iteration, including manual device tagging and sterilization considerationsPersonal reflections on work-life balance, mental resilience, and the mindsets of successful foundersThe strategic decision to own hardware assets versus leasing or selling equipmentFuture 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 FanBravo - Dan @ Jemini Dan's LinkedIn Connect with Greg Prosser: Hansel Medical Website Greg's LinkedIn 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 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

    1h 5m
  6. Innovating Healthcare with AI w/ Jonathan Miller @ Chiron Medical

    Apr 7

    Innovating Healthcare with AI w/ Jonathan Miller @ Chiron Medical

    Join me as I chat with Jonathan Miller, CEO of Chiron Medical Technologies, about transforming healthcare through innovative AI solutions. From his startup journey in travel tech to solving physician shortages, Jonathan shares lessons learned in navigating tech, product market fit, and regulatory landscapes in healthcare. Discover the underlying systems theory approach that sets his medical AI apart and the future of AI-enabled diagnostics. Main Topics Covered: The evolution of AI in healthcare and its potential to augment physicians rather than replace themTechnical details of how Chiron Medical's proprietary system organizes medical data for real-time diagnosis supportLessons learned from startup failures: importance of market research, user-centric design, and rapid iterationHow system theoretical approaches can outperform traditional NLP models in complex problem-solvingThe impact of AI on addressing the global physician shortage and improving access to timely careFuture trends in medical tech: automation, low-cost diagnostics, and democratization of healthcare expertise This episode emphasizes the importance of a systems theory approach in AI development, applied across travel, airline, and health tech sectors. Jonathan's insights highlight the immense potential of AI to augment medical decision-making, especially amid doctor shortages and increasing medical data complexity. The discussion explores not just technological innovation but strategic evolution, market awareness, and philosophical foundations underpinning AI systems in healthcare. 00:00 Introduction and Personal Reflections02:30 Business Outlook and Economic Perspectives04:55 Hope for Technological Advancements in Healthcare07:39 The Journey to CTO: Founding a Travel App10:22 The Problem with Travel Booking: A Personal Experience13:21 Building the Travel App: From Idea to Execution15:50 Innovative Approaches to Travel Technology18:36 The Future of Travel Tech and AI Integration21:55 The Evolution of Travel Technology25:42 Pivoting from Consumer to B2B27:24 Lessons from Startup Challenges31:40 Navigating Novelty in User Experience36:17 Understanding Customer Acquisition Costs38:30 Transitioning to CEO at Box Compliment43:42 Lessons from BoxComplement46:13 Transitioning to Chiron Medical Technologies48:27 Challenges in Clinical Reasoning50:00 Enhancing Doctor's Capabilities with AI54:08 A New Approach to AI in Healthcare58:05 The Role of Technology in Patient Care Resources & Links: Fanbravo - Dan @ Jemini Jonathan Miller LinkedIn Chiron Medical Technologies Blending a strong mathematical foundation with a business education, ⁠Jonathan Miller⁠ is drawn naturally to complex problem domains characterized by end-to-end intractability and systemic-level challenges. A prolific innovator, Jon has co-authored multiple patents that advanced fields like traveler inference, multi-attribute platforms, natural language fulfillment, and integrated medical systems. As the primary inventor of the patent governing Chiron’s technology solution, he leads the company in the development of its proprietary AI-driven clinical decision support tools. Music by Eggy Toast

    1h 5m
  7. Building in the AI Era: Avoiding Regret, Learning Fast, and Deploying Daily w/ Nathan Anderson of Tú TeleDoc

    12/16/2025

    Building in the AI Era: Avoiding Regret, Learning Fast, and Deploying Daily w/ Nathan Anderson of Tú TeleDoc

    Dan Villa sits down with Nathan Anderson, CTO at Tú TeleDoc, to talk about how AI is transforming tech—and how founders and builders can avoid AI regret. Nathan shares practical advice for newcomers entering this brave new technical world, the skills that matter most in an AI-driven era, and how he achieved continuous daily deployments at previous startups. They also discuss what it takes to move fast, build effectively, and keep up as technology evolves. A fun, insightful conversation on building smarter in the age of AI. Nathan Anderson is a Chief Technology Officer and an experienced leader in Software Engineering, DevOps, and Product. He has a passion for connecting technical challenges to delightful customer outcomes and focuses on building and maintaining highly engaged teams. In his current role as Co-Founder and CTO of Tú TeleDoc, Nathan is dedicated to building the technology platform to help transform healthcare access in Latin America. Keywords AI, software engineering, tech evolution, job security, product management, leadership, junior engineers, tech stack, telemedicine, career advice, software engineering, product management, communication, AI in tech, career progression, telehealth, engineering culture, startup life, leadership, technology strategy Sound Bites "It's an exciting time to be in tech." "AI won't fully replace our jobs." "Learn new stuff to survive in tech." Chapters 00:00 The Excitement of Tech Evolution01:06 AI Took This Architect's Job 05:36 Who's Impacted Most by AI?06:55 How do Newcomers Get Started in Tech? 11:48 Startup Life and AI Hype13:57 Nate's Tech Stack15:40 Getting Past the Hype17:12 Starting the Journey toward CTO24:13 AI Doesn't Matter, Invest in These Things30:07 You're a Manager, not a Buddy34:10 Learning not to Undervalue a Good Mentor38:22 The Best Measure of Success; and How To43:08 The Intersection of Product Management and Engineering48:09 Bridging the Gap: Communication Between Engineers and Product Teams53:55 The Role of AI in Software Development01:04:08 Career Progression: From Rackspace to CTO01:09:07 Mastering 15 Deploys Per Day 01:19:20 The Biggest Failure as a CTO01:25:15 Building a Telehealth Platform: Challenges and Opportunities Music by Eggy Toast

    1h 34m
  8. The CTO Reality Check: Imposter Syndrome, AI Tools, and Low-Code Risks w/ Jason Kerner from Hansel Medical

    12/02/2025

    The CTO Reality Check: Imposter Syndrome, AI Tools, and Low-Code Risks w/ Jason Kerner from Hansel Medical

    In this conversation, Jason Kerner from Hansel Medical shares his insights on the intersection of technology and business, discussing his journey from a global architect to a CTO. He emphasizes the importance of subject matter expertise, overcoming public speaking anxiety, and the transformative impact of AI on software development. Jason also highlights the challenges of balancing technical decisions with business needs, particularly in the healthcare sector, and the value of community support for tech leaders. He concludes with thoughts on the future of tech and the importance of user-friendly solutions in healthcare. Jason Kerner is CTO and Co-Founder of Hansel Medical, previously Chief Global Architect at IntelliCentrics and Head of Product Experience and Architecture at Agilio Software. A hands-on builder, with 20+ years in the software development world with mobile apps, web applications, cloud and AI experience. Excited about all things tech, as well as involvement with product and marketing teams. Keywords technology, business, AI, public speaking, software development, healthcare, startups, CTO, IntelliCentrics, community Sound bites "I enjoy discussing tech and business." "AI is transforming software development processes." "Leveraging AI for development efficiency is key." Chapters 00:00 Introduction to Tech and Business Passion 05:17 Navigating Imposter Syndrome 10:39 The Evolution of Tech Careers 16:14 Jason's Journey into Tech 21:24 Building Solutions for Modern Problems 27:47 Learning from Technical Mistakes 32:43 The Low Code Dilemma 39:03 Balancing Technical and Business Decisions 45:47 The Agile Approach to Business Value 51:01 Transitioning to a Startup Environment 58:32 Future Milestones and Community Engagement Music by Eggy Toast

    1h 2m
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"How NOT to Build" is about uncovering the lessons Founders, CTOs, Tech Leads, and Team Leads wish they’d known earlier. I hope these stories spark ideas, offer guidance, and help you navigate your journey to turning vision into reality.

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