PODCAST · technology
How Many CTOs
by Brad Hefta-Gaub & Scott Porad
Welcome to the "How Many CTOs?" Podcast, hosted by Brad and Scott, where we dive deep into the intricate world of Chief Technology Officers. Each episode features candid conversations with guest CTOs who share their real-world experiences and insights on a wide range of topics. From building and upleveling high-performing engineering teams to managing and communicating the impact of tech debt, we cover it all. Discover strategies for measuring engineering productivity, refining processes, and balancing innovation with structured methodologies. Learn from experts about decomposing monolithic systems and keeping up with the latest technology trends. Whether you're a current or aspiring CTO, our podcast offers practical solutions and valuable advice to navigate the ever-evolving landscape of technology leadership. Tune in and join the discussion on overcoming the common challenges faced by CTOs today. Don't forget to subscribe, rate, and review! #TechLeadership #CTO #techpodcast
Episodes
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Preparing for the Worst: Tabletop Exercises, Unit Tests, and Everything In Between
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss TaskRabbit's overnight AWS region migration from us-west-1 to us-west-2, describing the months of preparation, detailed runbook, large war-room call, minor cleanup issues, and why periodic…
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Understanding The Fear: Adaptive Leadership in the AI Age
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss growing fear about AI among engineers and managers, framing it as an "adaptive moment" requiring leaders to disrupt old stabilizing practices. They explore concerns that AI lowers the barrier…
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Simplifying Tech Through Empathy and Understanding with Frank Bravo
In this episode of "How Many CTOs Does It Take?" podcast, host Brad Hefta-Gaub is joined by guest Frank Bravo, a Bay Area technologist who spent 30 years as CTO in local media, helping put a newspaper's full editorial content online in 1994, and now serves as CTO at ProLegal, a legal services...
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Managing Skepticism: Balancing Tradition and Technology with AI
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss how AI is changing software engineering referencing Kent Beck's idea that AI makes much existing knowledge less useful while making a smaller portion far more valuable. They describe teams...
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From Academia to Industry: Scott Hanson on the Future of AI and Edge Computing
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub interview Scott Hanson, founder and CTO of Ambiq, a company focused on ultra-low-power chips for "intelligence everywhere," with 300M+ units shipped into wearables and other devices. Hansen traces...
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Beyond Cost Reduction: AI in Revenue Generation and Innovation with Andy Boettcher
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub interview Andy Boettcher, Chief Innovator of DoubleTrack, a boutique data and AI consultancy. Andy recounts his 33 years across systems, development, with 13 years in Salesforce, and how his career...
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The Hardware/Software Blend: Visionary Innovations in Health Tech with Eyebot's Jack Moldave
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub interview Jack Moldave of Eyebot, a company he co-founded nearly six years ago to make getting glasses as easy as buying shoes by enabling on-demand vision tests and prescriptions in retail settings....
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Fast, On Time, or Fully Utilized? Choosing What to Optimize in Engineering Delivery
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss a leadership conversation where three senior stakeholders wanted different outcomes from engineering: delivering faster, maximizing utilization, or delivering on time—highlighting unclear norms...
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The Pace of Innovation: Systems Thinking for Faster Engineering
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub open with travel and sports talk, including World Cup rules, then pivot to Scott's change-management training on systems thinking and unspoken norms. They explore a meta-question: if non-engineering...
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Method to the Madness: A CTO Framework for Systemic AI Adoption
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss how CTOs must frame narratives that help teams organize around ideas, inspired by how Scott explained his company's AI work to a non-technical friend. The hosts outline four intertwined AI...
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There's A Pattern To Follow: An Interview with Robert "Uncle Bob" Martin
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub are honored to interview Robert "Uncle Bob" Martin, who recounts his 60+ year programming journey from a three-bit binary device and years of assembly to C, C++, and Java, to now using AI agents to…
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Is Uncle Bob Right? Reading Code vs. Architecting the Future
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss how Robert "Uncle Bob" Martin—author of Clean Code and Agile Manifesto signer—sparked online controversy by saying he no longer reads the source code produced by his programming agents. They...
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Token Maxxing and Local Inference: Navigating the Shift in AI Usage for Developers
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss token spending and the "token maxing" backlash, sparked by a GitHub Copilot budget issue and broader industry moves to optimize tokens. The hosts argues companies should focus on value and...
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This Has Always Been A Problem: Slot Machine Devs and Growing Junior Engineers in the Age of AI
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss how managing armies of coding agents can be physically draining, likening it to context switching in flat organizations. Scott references Yuval Harari's "Sapiens," connecting the cognitive and...
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From Chaos to Control: Bringing Specification Driven Design to Vibe Coding with David Bauer
In this episode of "How Many CTOs Does It Take?" podcast, host Brad Hefta-Gaub is joined by Dr. David Bauer of Axonis AI, who shares how his background in distributed computing, startups, and the U.S. intelligence community led him to Axonis AI's federated data layer used for federated learning,...
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Introducing Skein and Beaker Stack: Using AI Agent Engineers to Ship SaaS Faster
In this special episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss Brad's experiment proving that AI can dramatically boost output for teams with strong engineering practices. Brad shares an MIT-licensed open-source SaaS template called Beaker Stack,...
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AI and the Data Swamp In Your Backyard with Ben Wilcox
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub interview guest Ben Wilcox, CTO and CISO of ProArch, a Microsoft-focused data and AI system integrator. Wilcox describes his path into system integration, from cloud transformation and building managed...
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Pioneering Music Education with John von Seggern
In this episode of "How Many CTOs Does It Take?" podcast, Brad Hefta-Gaub interviews John Von Seggern, founder/CEO/CTO of Future Proof Music School, about his shift from musician and online educator to building AI features using tools like Claude Code, n8n, and MCP servers. John describes the...
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Removing Bottlenecks, Not People with Stephanie Sylvestre
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad is joined by guest Stephanie Sylvestre, founder of AvatarBuddy, an AI company started 10 years ago to help people be the best version of themselves. Sylvestre argues for "AI plus human" rather than job elimination, and...
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Pioneer or Perish: How and When to Evolve Your Engineering Org Toward the AI Development Life Cycle
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss a high-performing engineering team that has effectively cleared its product backlog while using AI heavily, including a senior engineer who surprised Brad by running agents overnight to...
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Navigating the Future: Gas Town and Bespoke AI Agents
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss Brad's viral LinkedIn post arguing that AI has collapsed the economics that drove generalized SaaS, enabling more bespoke software for underserved SMBs and vertical niches. They debate…
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Uncovering Hidden Ambiguities: Why Product Managers Need to Adapt to AI Tooling
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss spec-driven development and SpecKit, starting with Brad's story of a product owner resisted SpecKit because it produced "too many words," alongside Scott's example of accepting a 60,000-line…
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A Fundamental Shift: Change Management, Psychological Safety, and AI's Impact on Engineering Leadership with Dr. Adam Link
In this episode of "How Many CTOs Does It Take?" podcast, host Brad Hefta-Gaub is joined by Dr. Adam Link, former senior engineering manager at Coinbase, who shares his background leading global teams through highly technical transformations in fintech and crypto, including major infrastructure...
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An Ideal Partnership: How and When to Split CTO and VP of Engineering Duties
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss the recurring question: when it's appropriate to hire a VP of Engineering and how to divide responsibilities so the CTO can better align product, business, and technology strategy. They define...
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Where Does the Alpha Flow?: Rethinking Software Value in the Age of AI
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss a conversation Scott had with coworkers after discovering Confluence connected to Google Drive and Slack, raising questions about whether to rely on tools like Confluence or a generic layer…
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Product-Market Fit and Pragmatic AI: Insight from RevenueCat's CTO Miguel Carranza
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub" interview Miguel Carranza Spanish-born co-founder/CTO of RevenueCat, who describes discovering subscription billing pain while building the Elevate app and turning that hard, "boring" problem into a...
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The Most Optimized Blue: Differences Between UI and User Experience Design with Nick Cawthon
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub 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 modern dashboards increasingly look the same, so...
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Balancing 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 AI tools are increasing risk, with Brad concerned about security amid recent supply-chain attacks. Brad shares how an AI agent setting up a...
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Engaging Employees in Security Appreciation with Robert Siciliano
In this episode of "How Many CTOs Does It Take?" podcast, host Brad Hefta-Gaub welcomes Boston-raised security speaker Robert Siciliano, who traces his path into security from early experiences with crime, teaching physical self-defense, and being hacked in the mid-1990s. Robert argues that most...
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Building Trust with AI: David Espindola on the Path Forward
In this episode of "How Many CTOs Does It Take?" podcast, Scott Porad hosts solo and interviews technologist David Espindola about AI. Espindola explains his path from engineer at fast-growing Silicon Valley companies to 10 years at Oracle implementing ERP/CRM for Fortune 500 clients, then a…
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Beyond Transcripts: Language Nuances and Audio Signals with Carter Huffman of Modulate
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub 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 that understands conversations. Carter explains...
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Introducing the ADLC: The Agent Development Life Cycle
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub" 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 a site crash for a Claude wrapper. They discuss...
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The Evolving Role of Tech Leadership with Philip Rosedale
In this episode of "How Many CTOs Does It Take?" podcast, 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 joy of working on products versus managing teams, and share anecdotes such as their...
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Predictions and Reflections: One Year Anniversary of the How Many CTOs Does It Take? Podcast
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub" reflect on the first year of the podcast's publication, discussing Scott's ongoing questions about tech debt and struggles with refactoring, the advances made in AI assissted programming, and the...
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Adapt or Fade: Interviewing for Developers in the Age of AI Assisted Coding
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub explore the evolving landscape of interviewing for programmer positions in the age of AI-assisted coding. They discuss the relevance of traditional leetcode questions, best practices for evaluating...
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From Rave Promoter to SaaS Innovator: Revolutionizing Event Management with Ritesh Patel
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub 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 platform tailored for the live events industry....
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From the Dress Code to the Bottom Line: A CTO Business Primer
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss the interplay between tech and business. Starting with comments about their own scruffiness and stories of wearing hats to interviews and fancy restaurants, they delve into how CTOs can...
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The K-Shape of AI Development: Managing Digital Interns
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub 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 tokens used, prompting a discussion about the...
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Setting the Tone: Building Trust Through Security
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss the role of CTOs in setting a security-minded culture and provide real-life anecdotes of security breaches and incidents. The conversation covers critical frameworks like CIS, SOC 2, and tools...
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Rediscovering the Joy of Coding through AI with Paul Brown
In this episode of "How Many CTOs Does It Take?" podcast, 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 potential to enhance productivity. Paul shares his journey from skepticism about AI's...
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Year 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 will be taking a two-week break for the holidays and will return with Season 2 on January 13th. They reflect on their first year, discussing the...
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Turtles All The Way Down: AI Insights with Scott W. Bradley
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub welcome guest Scott W. Bradley, Managing Partner at Facet Digital, to delve into the complexities and potential pitfalls of AI technology. With insights drawn from Bradley's provocative LinkedIn post...
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The AI Race: Who's Ahead, Anthropic or OpenAI?
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub compare Anthropic and OpenAI's distinct business strategies. While OpenAI takes a high-risk, expansive approach aiming for rapid growth, Anthropic focuses on a more disciplined, business-centric path,...
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CTO Therapy: The Risks and Rewards of Vendor Partnerships
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub delve into Scott's recent meeting with AWS. They discuss the concept of vendors supporting their clients, weighing potential benefits against risks like vendor lock-in and misaligned solutions. The...
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Let Them Eat Tokens: AI Efficiency vs. Global Good
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub 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 explore the current state of AI and its varied...
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Cabinet Doors Should Open: Avoiding Assumptions in Product Requirements
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss the critical importance of clear requirements in both hardware and software projects. Using the analogy of a home renovation project, they explore how detailed planning and frequent…
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The State of AI in 2025: What the DORA Report Reveals
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub 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 AI, its impact on productivity, and its role in...
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The AI Hype Cycle: Navigating Growth and Skepticism
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub reflect on the recent shifts in Big Tech's approach to AI, discussing the changing perceptions and economic impacts of the technology. They provide insights into the AI hype cycle, comparing it to the...
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In Search of the Exceptional: Unpacking the Traits of 10x Engineers
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub dive deep into the concept of the 10x engineer—those rare developers who are exponentially more productive than their peers. They discuss attributes such as natural talent versus learned skills,...
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The Documented SDLC: Why Every Team Needs One (and When)
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub start with a quick retrospective, or is it an encore, of recent rock concerts before stage-diving into a lively discussion about the Software Development Life Cycle (SDLC): what it is, when it matters,...
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ABOUT THIS SHOW
Welcome to the "How Many CTOs?" Podcast, hosted by Brad and Scott, where we dive deep into the intricate world of Chief Technology Officers. Each episode features candid conversations with guest CTOs who share their real-world experiences and insights on a wide range of topics. From building and upleveling high-performing engineering teams to managing and communicating the impact of tech debt, we cover it all. Discover strategies for measuring engineering productivity, refining processes, and balancing innovation with structured methodologies. Learn from experts about decomposing monolithic systems and keeping up with the latest technology trends. Whether you're a current or aspiring CTO, our podcast offers practical solutions and valuable advice to navigate the ever-evolving landscape of technology leadership. Tune in and join the discussion on overcoming the common challenges faced by CTOs today. Don't forget to subscribe, rate, and review! #TechLeadership #CTO #techpodcast
HOSTED BY
Brad Hefta-Gaub & Scott Porad
CATEGORIES
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Frequently Asked Questions
How many episodes does How Many CTOs have?
How Many CTOs currently has 91 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is How Many CTOs about?
Welcome to the "How Many CTOs?" Podcast, hosted by Brad and Scott, where we dive deep into the intricate world of Chief Technology Officers. Each episode features candid conversations with guest CTOs who share their real-world experiences and insights on a wide range of topics. From building and...
How often does How Many CTOs release new episodes?
How Many CTOs has 91 episodes. Check the episode list to see recent publication dates and frequency.
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Who hosts How Many CTOs?
How Many CTOs is created and hosted by Brad Hefta-Gaub & Scott Porad.
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