How NOT To Build: Startup Stories | A Jemini Podcast

Dan Villa
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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.

  1. 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
  2. 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
  3. From Academia to Entrepreneurship: Startups, Setbacks, and Success in Biotech w/ Cara Wells from Emgenisys

    06/24/2025

    From Academia to Entrepreneurship: Startups, Setbacks, and Success in Biotech w/ Cara Wells from Emgenisys

    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

    1h 11m
  4. Adapting, Automating, and Building Community w/ Jacques Greeff from Founders Table

    06/12/2025

    Adapting, Automating, and Building Community w/ Jacques Greeff from Founders Table

    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

    1h 4m
  5. Niche SaaS, Modern Stacks, and CTO Strategy w/ Brandon Powers from Hyperformant

    06/03/2025

    Niche SaaS, Modern Stacks, and CTO Strategy w/ Brandon Powers from Hyperformant

    In this episode, Dan Villa speaks with Brandon Powers, founder of Hyperformant, about practical advice for software companies, including how to avoid over-engineering products, the balance between specialization and generalization, and the current state of SaaS. They discuss the importance of efficient meetings, managing anxiety, and the role of AI in software development. Brandon shares insights from his experiences with startups, including lessons learned from failures and the significance of preparing for acquisition. The conversation emphasizes the need for industry-specific solutions and the evolving landscape of technology. Brandon Powers is a father of four, progressive thinker, and relentless tinkerer. Over the past 19 years, he’s scaled six companies as a CTO and software architect across fintech, healthcare, social media, and retail. His latest venture, Hyperformant, blends visionary technical insight with creative market positioning strategies to help software companies achieve unbridled growth and command top-tier valuations. Music by Eggy Toast 00:00 Simple Advice for Meeting Efficiency 02:31 Learning to Deal With and Learn From Stress 05:56 Advise for Aspiring Entrepreneurs | Don’t Buy the FOMO Lie 11:19 The Reward of Being Your Own Boss 12:14 The High Impact of Domain Expertise for Your Product 19:43 How to Avoid Over-Engineering 26:40 Making the Most of AI as an Engineer 31:08 How to Skill Up: Specialist or Generalist? 38:44 Who Should (And Should Not) Care About AI Governance 41:52 The Unethical Thing About AI Replacing Jobs 49:39 The Future of SaaS: Is It Really Dead? 56:33 Modern Web Stacks and Frameworks for Startups 01:03:39 The 10X CTO: Understanding that Business & Tech Are… 01:09:24 If You’re Looking to Sell, Do NOT Do This

    1h 15m
  6. The Evolution of Marketing Strategies w/ Ellen Messer from TechTalk Marketing

    05/23/2025

    The Evolution of Marketing Strategies w/ Ellen Messer from TechTalk Marketing

    In this episode, Ellen Messer, CEO and founder of Tech Talk Marketing, shares her journey in the marketing industry, discussing the evolution of marketing strategies, the challenges of running a business, and the importance of understanding customer needs. She emphasizes the need for a solid marketing plan and the common mistakes companies make in their marketing efforts. The discussion also touches on the significance of local searches in today's digital landscape and the ongoing changes in marketing due to technology and AI. Ellen Cusato Messer helps engineering and software development firms build a continuous flow of ideal projects using her own proprietary marketing system. She based the system on decades of noting the differences between successful development projects that led to new projects, and unsuccessful projects that did not. Ellen has spent her entire career working with engineers to translate technical concepts into successful marketing programs, starting with 13 years at Nortel in wireless product management and marketing. IoT Meetup: https://www.meetup.com/iottexas/ Nortel: https://en.wikipedia.org/wiki/Nortel Music by Eggy Toast 0:00 - Speaking at Conferences for Marketing 06:30 - Thinking Forward: Planning your Career a Decade in Advance 12:12 - What’s Changed in Marketing? Everything and Nothing. 14:56 - Applying the “Post Everyday” Advice Correctly 20:32 - The Value of Fun Content 21:55 - How Ellen Got Her First Customer 26:38 - The Worst Moment 31:05 - The Long Path to Success 32:58 - Why Quitting Wasn’t an Option 38:01 - The Biggest Marketing Mistakes from 20+ Years of Experience 42:42 - The Importance and Potential of the Local Market 50:12 - Finding and Leveraging your Differentiators 53:50 - “Modern Marketing is Different” Isn’t True

    55 min
  7. From Motorcycles to AI: Tesla, Uber, and Building CertBuddyAI to Revolutionize Global Compliance w/ Kannan Govindasamy from CertBuddyAI

    05/07/2025

    From Motorcycles to AI: Tesla, Uber, and Building CertBuddyAI to Revolutionize Global Compliance w/ Kannan Govindasamy from CertBuddyAI

    Join us for this episode as Kannan Govindasamy shares his journey from Tesla and Uber to founding CertBuddyAI, an AI-driven platform transforming product compliance. Learn how he navigated global challenges, built high-performing teams, and leverages AI to simplify complex processes. This episode is a must-listen for innovators looking to scale efficiently and strategically. Kannan Govindasamy is a seasoned product certification expert and has over 25 years of experience and worked with most successful startups like Tesla and Uber. Founder of CertBuddyAI - We can help any Physical Product Manufacturer's certification process from start to end, e.g. such as cars, medical devices and aircrafts. These products usually take 2-3 years of product design and certification cycle where our AI Platform can cut down time, cost, and business up to 50%. It can also help manage regulations, create automated design and test tasks, validate reports and help file applications with government agencies such as EPA, FDA, FAA. If interested, please reach out for any demo. E-mail kannan@certbuddyai.com YouTube - CERTBUDDYAI - https://www.youtube.com/@CERTBUDDYAI Music⁠⁠⁠⁠ By Eggy Toast 0:00 - Intro 4:17 - Cutting Teeth on Manually Reading Hundreds of Pages 7:03 - Can Someone Really Say “I haven’t worked a day in my life?” 9:54 - Keeping the Motivation to Keep on Keeping On 14:40 - Engineers: Do Not Underestimate the Importance of Certification 16:40 - Lessons from Tesla & Burnt Hair 29:10 - Helping Uber Rollout Scooters to the World 37:03 - Lessons from Uber: Goals & Teams 40:32 - Advice on Building the Critical Team 43:01 - Productizing 25+ Years of Expertise With CertBuddy.ai 48:51 - The Future of Cert & Advice For Founders

    53 min
  8. Building Smart Startups: Avoiding Pitfalls, Leveraging Founders, and Harnessing AI w/ Andrew Hosch from Collinear Group

    04/30/2025

    Building Smart Startups: Avoiding Pitfalls, Leveraging Founders, and Harnessing AI w/ Andrew Hosch from Collinear Group

    In this episode, we dive into the challenges startups face—from balancing tech development with marketing to navigating founder dynamics and market uncertainty. We discuss lessons learned from failed ventures, practical strategies for adopting new technologies, and the transformative potential of AI in the startup ecosystem. Whether you’re a founder, investor, or tech enthusiast, this conversation is packed with actionable insights for building smarter, more resilient startups. Andrew Hosch is the COO at Collinear Group where he’s helping people use the right technology for the right reasons. With their GC Accelerate program, Andrew and his team specialize in shipping Go-To-Market SaaS Solutions that elevate your business. Music⁠⁠⁠ By Eggy Toast 0:00 - Is This The Most Challenging Time in 25 Years? 7:35 - Advice for Weathering These Interesting Times 9:45 - Tariffs & The Fundamentals to Watch Out For 15:41 - Lessons From Being a First Time VP: the N-1 Rule 25:16 - Staying Sane in AI-insane Times 28:32 - The Danger of Underestimating Marketing and How To Avoid It 41:38 - The #1 Reason(s) Startups Fail, from a 20-year Veteran 45:06 - Being COO at Collinear Group and Solving the Magic Beans Problem 53:30 - What’s Next for Collinear Group

    47 min
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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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