How NOT To Build: Startup Stories | A Jemini Podcast

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”

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

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

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

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

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

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 them
• Technical details of how Chiron Medical's proprietary system organizes medical data for real-time diagnosis support
• Lessons learned from startup failures: importance of market research, user-centric design, and rapid iteration
• How system theoretical approaches can outperform traditional NLP models in complex problem-solving
• The impact of AI on addressing the global physician shortage and improving access to timely care
• Future 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 Reflections
02:30 Business Outlook and Economic Perspectives
04:55 Hope for Technological Advancements in Healthcare
07:39 The Journey to CTO: Founding a Travel App
10:22 The Problem with Travel Booking: A Personal Experience
13:21 Building the Travel App: From Idea to Execution
15:50 Innovative Approaches to Travel Technology
18:36 The Future of Travel Tech and AI Integration
21:55 The Evolution of Travel Technology
25:42 Pivoting from Consumer to B2B
27:24 Lessons from Startup Challenges
31:40 Navigating Novelty in User Experience
36:17 Understanding Customer Acquisition Costs
38:30 Transitioning to CEO at Box Compliment
43:42 Lessons from BoxComplement
46:13 Transitioning to Chiron Medical Technologies
48:27 Challenges in Clinical Reasoning
50:00 Enhancing Doctor's Capabilities with AI
54:08 A New Approach to AI in Healthcare
58:05 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

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

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

In this episode, Cara Wells, PhD, shares her journey from academia to entrepreneurship, detailing her experiences with fundraising, market disruption, and the challenges of navigating the startup landscape. She discusses her first venture, Embryotics, the lessons learned from its dissolution, and the ongoing legal battles stemming from her whistleblower actions. Cara also introduces her current company, Emgenisys, which focuses on innovative solutions for embryo health using machine learning. She emphasizes the importance of owning intellectual property, building a strong founding team, and the realities faced by PhD graduates in the job market.

Dr. Cara Wells is a scientist and entrepreneur with a PhD in Animal Science from Texas Tech University, specializing in reproductive physiology and assisted reproductive technologies in animals and humans. She is the founder and CEO of EmGenisys, where she leads the development of software to improve embryo evaluation and pregnancy outcomes in IVF and embryo transfer. Her earlier experience co-founding Embryotics—an effort that highlighted the challenges of commercializing university-owned IP—helped shape her more strategic and scalable approach at EmGenisys.

Music by Eggy Toast

00:00 The Biggest Learnings After Raising 1.5M03:52 How to Market a Disruptive Product 07:17 Breaking into the Global Market to get 2.5M Euro12:28 Cracking the Code on the Grant Process14:29 Going from PhD to Product Idea22:03 The Disconnect Every PhD Should Understand 24:38 Dan and Cara Rip Apart Higher Education31:46 Commercialization Challenges and Dream Team Drama39:21 How NOT to Lose Your IP and Equity44:44 The Crazy Story of The Texas Tech Lawsuit 54:16 Not Giving Up with EmGenisys56:58 The Option Pool Pro Tip for Founders01:03:36 The Value of Contractors in Startups 01:08:55 The Future of EmGenisys

In this episode, Jacques Greeff reflects on his entrepreneurial journey, sharing insights from building RealHub and navigating the evolving role of AI in startups. He explores the challenges and opportunities of adapting to rapid technological change and underscores the critical role of community and collaboration in fostering innovation. Jacques also shares about Founders Table, aimed at connecting entrepreneurs and providing a supportive environment to drive meaningful growth in the future of work shaped by automation and emerging trends.

Jacques Greeff co-founded Realbase, a real estate marketing platform that scaled across Australia and was acquired for $180M. After exiting, he turned his focus to solving a deeper productivity problem: how high performers manage relationships, time, and communication at scale. He’s now building Kinso, an AI executive assistant designed to act as a second brain for messaging, calendars, and follow-through.

Music by Eggy Toast

00:00 Introduction

01:46 The Rapid Advancement of AI

04:53 Startups in the Age of AI

12:54 Early Entrepreneurial Ventures

17:12 The Birth of RealHub

24:03 Lessons Learned in Hiring and Team Building

30:34 Misconceptions and Advice for Entrepreneurs

32:40 The Importance of High-Leverage Skills

37:22 Content Creation as a Key to Traction

40:02 Building a Supportive Community for Founders

48:27 The Art of Community Building

52:53 Innovating with AI for Founders

57:51 Learning from Past Experience