How NOT To Build: Startup Stories | A Jemini Podcast
How NOT To Build: Startup Stories | A Jemini Podcast
Podcast Description
"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.
Podcast Insights
Content Themes
The podcast focuses on themes of entrepreneurship, technology management, and startup growth, with episodes covering topics such as bootstrapping challenges, effective leadership in global teams, and insights on managing software projects. Specific episodes include discussions on hiring smart for offshore teams and balancing confidence as a leader.

“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.
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

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