All Episodes

Preparing for the Worst: Tabletop Exercises, Unit Tests, and Everything In Between

Understanding The Fear: Adaptive Leadership in the AI Age

Simplifying Tech Through Empathy and Understanding with Frank Bravo

Managing Skepticism: Balancing Tradition and Technology with AI

From Academia to Industry: Scott Hanson on the Future of AI and Edge Computing

Beyond Cost Reduction: AI in Revenue Generation and Innovation with Andy Boettcher

The Hardware/Software Blend: Visionary Innovations in Health Tech with Eyebot's Jack Moldave

Fast, On Time, or Fully Utilized? Choosing What to Optimize in Engineering Delivery

The Pace of Innovation: Systems Thinking for Faster Engineering

Method to the Madness: A CTO Framework for Systemic AI Adoption

There's A Pattern To Follow: An Interview with Robert "Uncle Bob" Martin

Is Uncle Bob Right? Reading Code vs. Architecting the Future

Token Maxxing and Local Inference: Navigating the Shift in AI Usage for Developers

This Has Always Been A Problem: Slot Machine Devs and Growing Junior Engineers in the Age of AI

From Chaos to Control: Bringing Specification Driven Design to Vibe Coding with David Bauer

Introducing Skein and Beaker Stack: Using AI Agent Engineers to Ship SaaS Faster

AI and the Data Swamp In Your Backyard with Ben Wilcox

Pioneering Music Education with John von Seggern

Removing Bottlenecks, Not People with Stephanie Sylvestre

Pioneer or Perish: How and When to Evolve Your Engineering Org Toward the AI Development Life Cycle

Navigating the Future: Gas Town and Bespoke AI Agents

Uncovering Hidden Ambiguities: Why Product Managers Need to Adapt to AI Tooling

A Fundamental Shift: Change Management, Psychological Safety, and AI's Impact on Engineering Leadership with Dr. Adam Link

An Ideal Partnership: How and When to Split CTO and VP of Engineering Duties

Where Does the Alpha Flow?: Rethinking Software Value in the Age of AI

Product-Market Fit and Pragmatic AI: Insight from RevenueCat's CTO Miguel Carranza

The Most Optimized Blue: Differences Between UI and User Experience Design with Nick Cawthon

Balancing Innovation and Safety: CTOs Check-In About AI Evolution

Engaging Employees in Security Appreciation with Robert Siciliano

Building Trust with AI: David Espindola on the Path Forward

Beyond Transcripts: Language Nuances and Audio Signals with Carter Huffman of Modulate

Introducing the ADLC: The Agent Development Life Cycle

The Evolving Role of Tech Leadership with Philip Rosedale

Predictions and Reflections: One Year Anniversary of the How Many CTOs Does It Take? Podcast

Adapt or Fade: Interviewing for Developers in the Age of AI Assisted Coding

From Rave Promoter to SaaS Innovator: Revolutionizing Event Management with Ritesh Patel

From the Dress Code to the Bottom Line: A CTO Business Primer

The K-Shape of AI Development: Managing Digital Interns

Setting the Tone: Building Trust Through Security

Rediscovering the Joy of Coding through AI with Paul Brown

Year In Review: How Many CTOs Does It Take To Finish A Season?

Turtles All The Way Down: AI Insights with Scott W. Bradley

The AI Race: Who's Ahead, Anthropic or OpenAI?

CTO Therapy: The Risks and Rewards of Vendor Partnerships

Let Them Eat Tokens: AI Efficiency vs. Global Good

Cabinet Doors Should Open: Avoiding Assumptions in Product Requirements

The State of AI in 2025: What the DORA Report Reveals

The AI Hype Cycle: Navigating Growth and Skepticism

In Search of the Exceptional: Unpacking the Traits of 10x Engineers

The Documented SDLC: Why Every Team Needs One (and When)

Navigating BADD vs. FaDD: Strategic Refactoring in Software Development

From Specs to Monitoring: A CTO's Guide to QA Best Practices

Deploys, Demos, and the Elusive Metric of Engineering Productivity

Product Debt: The Hidden Drag on Innovation

From Streaker Apps to AI Safety Loopholes: What CTOs Need to Know

Do Engineering Managers Need to Code? Leveling, Calibration & Craft

From Prompts to Product: How AI is Changing Software Development

From Bugs to Bloat: Product Debt, KPIs, and the Cost of Features

CTO Therapy: Managing Urgency, Expectations, and Trust

From Coldplay to Code: AI Wins, Data Lakes, and the Age-Old Centralized vs. Distributed Debate

Design in the Age of AI: Craft, Tools, and the Future of Creativity

Storytelling, Not Spin: Founder-Led Marketing with Dan Woods

The Outsourcing Playbook Gets an AI Rewrite: Engineering in the Age of AI and Global Teams

From Code to Careers: AI's Disruption of Software and Work Itself

How GenAI Is Changing the Two Guys in a Garage Founder Story

Autonomous Engineering Teams: What Works, What Breaks

The End of Programming As We Know It? Justin Kaufman's tips on building fast with AI

From Chicken to Chatbots: Generative AI in Hospitality with Justin Kaufman

Fake Profiles, Real Disruption: What AI Is (and Isn't) Doing to Tech Recruiting with Dave Hardwick

Beyond the Resume: How to Hire and Get Hired in Tech with Dave Hardwick

Bonus Episode with Greg Conklin: Navigating Hyper-growth and Tech Debt at Groupon and Dropbox

Culture, Quality, and Tech Debt: Lessons from the Front Lines with Greg Conklin

Lessons from the Mountains: Retrospectives and the Secret Sauce of High Performance Teams

Exploring AI, Knowledge, and Ethics with John Helm (Bonus Episode)

Understanding and Managing Technical Debt: Insights from John Helm

The Ball of Mud - Tackling Software Monoliths and Decomposing Tech Debt: Strategies and Challenges

Embracing Failure and Innovation: Lessons from Punk Rock with Kevin Goldsmith

Navigating Technical Debt and Code Quality in Agile Teams

The Reality of AI in Software Engineering and the Future of Work

Tackling Tech Culture and Interviewing: Insights from Ted Neward

The Power of Drafting Implementation Plans: Insights and Strategies

Learning Styles and Team Dynamics: A Journey from Personal Trips to Strategic Decisions

Bonus Episode: Challenges and Insights From Using Cursor to Add a Feature to Our Website

Embracing AI in Software Development: An Interview with Michael Natkin of Glowforge

Org Structures and Measuring Platform Team Success

Effective Staff Meetings: Balancing Structure and Flexibility

Building Trust and Authentic Connections in Remote Teams

Embracing Innovation: Introducing the PR FAQ Framework with Marcelo Calbucci

Measuring Technical Debt and Technical Investments

Introducing Our Hosts: Scott and Brad

Introduction to How Many CTOs Does It Take? Podcast