Episodes - Page 2
91 episodes total
S2E16Where Does the Alpha Flow?: Rethinking Software Value in the Age of AI
A conversation Scott had with coworkers after discovering Confluence connected to Google Drive and Slack, raising questions about whether to rely on tools…
S2E15Product-Market Fit and Pragmatic AI: Insight from RevenueCat's CTO Miguel Carranza
" interview Miguel Carranza Spanish-born co-founder/CTO of RevenueCat, who describes discovering subscription billing pain while building the Elevate app…
S2E14The Most Optimized Blue: Differences Between UI and User Experience Design with Nick Cawthon
Talk with Nick Cawthon of gauge.io, who shares highlights from RSA 2026 and his career designing UX for InfoSec/SecOps/DevOps tools. Nick argues that…
S2E13Balancing Innovation and Safety: CTOs Check-In About AI Evolution
In this "What's on your mind?" episode of the "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss how non-engineers using…
S2E12Engaging Employees in Security Appreciation with Robert Siciliano
Welcomes Boston-raised security speaker Robert Siciliano, who traces his path into security from early experiences with crime, teaching physical…
S2E11Building Trust with AI: David Espindola on the Path Forward
I n this episode of "How Many CTOs Does It Take?" podcast, Scott Porad hosts solo and interviews technologist David Espindola about AI. Espindola explains…
S2E10Beyond Transcripts: Language Nuances and Audio Signals with Carter Huffman of Modulate
Talk with Carter Huffman, CTO and co-founder of Modulate AI, about his path from machine learning work at NASA's Jet Propulsion Lab to building voice AI…
S2E9Introducing the ADLC: The Agent Development Life Cycle
" open with Super Bowl reactions and a meme about non-fans describing plays, then pivot to the ai.com halftime ad, where heavy spending reportedly led to…
S2E8The Evolving Role of Tech Leadership with Philip Rosedale
Brad Hefta-Gaub is joined by guest co-host Philip Rosedale to explore the multifaceted role of a CTO, comparing it with the CEO position. They discuss the…
S2E7Predictions and Reflections: One Year Anniversary of the How Many CTOs Does It Take? Podcast
" reflect on the first year of the podcast's publication, discussing Scott's ongoing questions about tech debt and struggles with refactoring, the…
S2E6Adapt or Fade: Interviewing for Developers in the Age of AI Assisted Coding
The evolving landscape of interviewing for programmer positions in the age of AI-assisted coding. They discuss the relevance of traditional leetcode…
S2E5From Rave Promoter to SaaS Innovator: Revolutionizing Event Management with Ritesh Patel
Sit down with Ritesh Patel, co-founder of Ticket Fairy . Ritesh shares his journey from coding and organizing raves to creating a powerful vertical SaaS…
S2E4From the Dress Code to the Bottom Line: A CTO Business Primer
The interplay between tech and business. Starting with comments about their own scruffiness and stories of wearing hats to interviews and fancy…
S2E3The K-Shape of AI Development: Managing Digital Interns
Yet again delve into the transformative impact of AI on software engineering. Brad shares his 2025 Cursor Year in Review, revealing his record 2.9 billion…
S2E2Setting the Tone: Building Trust Through Security
The role of CTOs in setting a security-minded culture and provide real-life anecdotes of security breaches and incidents. The conversation covers critical…
S2E1Rediscovering the Joy of Coding through AI with Paul Brown
Hosts Scott Porad and Brad Hefta-Gaub are joined by Paul Brown to delve into the misplaced fears of AI supplanting engineers, highlighting instead its…
S1E49Year In Review: How Many CTOs Does It Take To Finish A Season?
In this special public service announcement episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub announce that they…
S1E48Turtles All The Way Down: AI Insights with Scott W. Bradley
Guest Scott W. Bradley, Managing Partner at Facet Digital, to delve into the complexities and potential pitfalls of AI technology. With insights drawn…
S1E47The AI Race: Who's Ahead, Anthropic or OpenAI?
Compare Anthropic and OpenAI's distinct business strategies. While OpenAI takes a high-risk, expansive approach aiming for rapid growth, Anthropic focuses…
S1E46CTO Therapy: The Risks and Rewards of Vendor Partnerships
Delve into Scott's recent meeting with AWS. They discuss the concept of vendors supporting their clients, weighing potential benefits against risks like…
S1E45Let Them Eat Tokens: AI Efficiency vs. Global Good
Dive into the pervasive influence of AI, starting with a critical look at Apple's Siri and its struggles to keep up with competitors like ChatGPT. They…
S1E44Cabinet Doors Should Open: Avoiding Assumptions in Product Requirements
The critical importance of clear requirements in both hardware and software projects. Using the analogy of a home renovation project, they explore how…
S1E43The State of AI in 2025: What the DORA Report Reveals
Dive into the 2025 DORA Metrics Report on the state of AI-assisted software development. They discuss key findings such as the near-universal adoption of…
S1E42The AI Hype Cycle: Navigating Growth and Skepticism
Reflect on the recent shifts in Big Tech's approach to AI, discussing the changing perceptions and economic impacts of the technology. They provide…