How Many CTOs?
94 episodes · since 2025

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S2E43 What Broke in Tech: Code Quality, AI Guardrails, and the Evolving Software Engineer Brad & Scott Brad & Scott continue to recap Gergely Orosz's "State of the Tech Industry" talk and focus on what "broke" and "what's next. " They argue that machine-generated code is overwhelming pull requests and code review, exposing that many organizations' quality gates were implicitly built around human speed, and they discuss how 98% uptime is becoming an unacceptable norm. AI-Assisted Engineering Nov 3, 2026 36:56 S2E42 The State of Tech in 2026: What Changed And What Didn't Brad & Scott Brad & Scott discuss a Pragmatic Engineer talk on the state of the tech industry in 2026, focusing on what changed and what hasn't. They argue this is a "golden age" of building software due to AI, while acknowledging current "creative destruction" that may ultimately make the industry leaner. AI-Assisted Engineering Oct 27, 2026 32:58 S2E41 The Human Needs in Augmented Coding: A Conversation with Kent Beck with Kent Beck Brad & Scott interview software pioneer Kent Beck about his background (JUnit, test-driven development, extreme programming, Agile Manifesto, and his book "Tidy First? ") and his current focus on "augmented development" with AI, which he calls a "genie. AI-Assisted Engineering Oct 20, 2026 01:09:53 S2E40 Preparing for the Worst: Tabletop Exercises, Unit Tests, and Everything In Between Brad & Scott Brad & Scott 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 region moves can serve as valuable "hygiene" to relearn and document complex systems while advancing disaster recovery and business continuity. They then explain tabletop exercises as structured incident-response drills designed to uncover gaps in process and documentation, sharing scenario ideas like data deletion, token leaks, cloud outages, ransomware, and internal actors, including an embezzlement case where the perpetrator joined incident response. AI-Assisted Engineering Oct 13, 2026 44:51 S2E39 Understanding The Fear: Adaptive Leadership in the AI Age Brad & Scott Brad & Scott 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 for others to change systems, increasing accountability, on-call risk, and architectural drift—problems that existed pre-AI but are now intensified. AI-Assisted Engineering Oct 6, 2026 34:28 S2E38 Simplifying Tech Through Empathy and Understanding with Frank Bravo with Frank Bravo, ProLegal Brad 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 startup. Frank describes modernizing an old Act! AI-Assisted Engineering Sep 29, 2026 50:13 S2E37 Managing Skepticism: Balancing Tradition and Technology with AI Brad & Scott Brad & Scott 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 collaborating through "cohorts" of AI agents for PR review and adversarial checking, and debate whether engineers will be evaluated on agent quality versus their ability to direct and manage agents like a driver or jockey. AI-Assisted Engineering Sep 22, 2026 49:59 S2E36 From Academia to Industry: Scott Hanson on the Future of AI and Edge Computing with Scott Hanson, Ambiq Brad & Scott 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 Ambiq's origins with University of Michigan smart-dust research and his PhD work on subthreshold computing—running transistors at extremely low voltages for quadratic energy savings—then explains the challenges of making it manufacturable across temperature and process variation. AI-Assisted Engineering Sep 15, 2026 45:58 S2E35 Beyond Cost Reduction: AI in Revenue Generation and Innovation with Andy Boettcher with Andy Boettcher, DoubleTrack Brad & Scott 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 shifted into data/AI full-time after ChatGPT's 2022 release. AI-Assisted Engineering Sep 8, 2026 50:24 S2E34 The Hardware/Software Blend: Visionary Innovations in Health Tech with Eyebot's Jack Moldave with Jack Moldave, Eyebot Brad & Scott 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. Jack explains Eyebot's kiosk experience in Walmart Vision Centers, including intake questions, visual acuity testing, touch-free refraction and glasses scanning, and remote review by licensed optometrists/ophthalmologists with prescriptions returned in under 15 minutes. AI-Assisted Engineering Sep 1, 2026 52:47 S2E33 Fast, On Time, or Fully Utilized? Choosing What to Optimize in Engineering Delivery Brad & Scott Brad & Scott discuss a leadership conversation where three senior stakeholders wanted different outcomes from engineering: delivering faster, maximizing utilization, or delivering on time—highlighting unclear norms and expectations in the software delivery system. The hosts argue you can't optimize all three at once, note that maximum utilization is a poor goal (systems perform better below 100% utilization), and debate prioritizing speed versus schedule. AI-Assisted Engineering Aug 25, 2026 16:37 S2E32 The Pace of Innovation: Systems Thinking for Faster Engineering Brad & Scott Brad & Scott 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 teams couldn't tell engineering to "go faster," what would they change to increase engineering throughput? AI-Assisted Engineering Aug 18, 2026 56:48 S2E31 Method to the Madness: A CTO Framework for Systemic AI Adoption Brad & Scott Brad & Scott 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 workstreams: getting AI to handle increasingly complex engineering (from functions to features to systems), moving toward autonomous "dark factory" software development, scaling AI adoption through standards and systems (shifting from organic experimentation to systemic usage, like AI code review and possible security/architect review agents), and managing token spend, including discussion of token-maxing incentives, looping, and interest in local inference and vendor lock-in mitigations such as AWS Bedrock. AI-Assisted Engineering Aug 11, 2026 45:26 S2E30 There's A Pattern To Follow: An Interview with Robert "Uncle Bob" Martin with Robert "Uncle Bob" Martin Brad & Scott 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 code. He explains how the Agile movement emerged from the design patterns community, Extreme Programming, and the 2001 Snowbird meeting that produced the Agile Manifesto. AI-Assisted Engineering Aug 4, 2026 01:01:57 S2E29 Is Uncle Bob Right? Reading Code vs. Architecting the Future Brad & Scott Brad & Scott 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 unpack his argument that strong "control systems" like automated unit and end-to-end tests, static analysis, and architecture acceptance criteria can replace line-by-line review, shifting human attention to higher-level architecture and justification. AI-Assisted Engineering Jul 28, 2026 43:05 S2E28 Token Maxxing and Local Inference: Navigating the Shift in AI Usage for Developers Brad & Scott Brad & Scott 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 learning rather than premature token optimization, while still adding circuit breakers to prevent runaway costs. AI-Assisted Engineering Jul 21, 2026 01:00:30 S2E27 This Has Always Been A Problem: Slot Machine Devs and Growing Junior Engineers in the Age of AI Brad & Scott Brad & Scott 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 agricultural revolutions to modern pressures. AI-Assisted Engineering Jul 14, 2026 56:26 S2E26 From Chaos to Control: Bringing Specification Driven Design to Vibe Coding with David Bauer with David Bauer, Axonis AI Brad is joined by Dr. David Bauer of Axonis AI, who shares how his background in distributed computing, startups, and the U. AI-Assisted Engineering Jul 7, 2026 51:27 S2E25 Introducing Skein and Beaker Stack: Using AI Agent Engineers to Ship SaaS Faster Brad & Scott Brad & Scott 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, which includes web and mobile scaffolding, CI/CD for preview/staging/production, automated setup, observability, email tooling, and Stripe-based tiered billing with feature gating. AI-Assisted Engineering Jun 30, 2026 49:54 S2E24 AI and the Data Swamp In Your Backyard with Ben Wilcox with Ben Wilcox, ProArch Brad & Scott 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 security services, and now focused on helping customers adopt AI securely. AI-Assisted Engineering Jun 23, 2026 47:33 S2E23 Pioneering Music Education with John von Seggern with John Von Seggern, Future Proof Music School Brad 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 school's personalized learning approach using an AI chatbot "Cadence" integrated with student history and curriculum, hosted on LearnWorlds, and explains solving integration limits by creating an MCP server and scraping LearnWorlds pages into a mirror database for context. AI-Assisted Engineering Jun 16, 2026 44:15 S2E22 Removing Bottlenecks, Not People with Stephanie Sylvestre with Stephanie Sylvestre, AvatarBuddy Scott 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 tells the story of how AvatarBuddy evolved from early research and prototypes to joining the OpenAI developer community in 2021, using teenagers for requirements and testing, and adopting curated "data vault" approaches (RAG) to improve results. AI-Assisted Engineering Jun 9, 2026 41:46 S2E21 Pioneer or Perish: How and When to Evolve Your Engineering Org Toward the AI Development Life Cycle Brad & Scott Brad & Scott 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 automatically perform fast, high-quality GitHub PR code reviews via a webhook-driven harness. The engineer built an opinionated, RAG-backed "world-class code review" skill set that pulls new PRs from selected repos, reviews them with defined criteria, and posts comments, highlighting the need to articulate engineering judgment rather than relying on gut feel. AI-Assisted Engineering Jun 2, 2026 33:24 S2E20 Navigating the Future: Gas Town and Bespoke AI Agents Brad & Scott Brad & Scott 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 practical examples like a plumber-specific CRM versus highly custom workflows for a regional law firm, including concerns about long-term maintenance, fragmentation, and risk. AI-Assisted Engineering May 27, 2026 43:21