Startup Hustle

Engineering Clarity in the Age of AI: How Docs, Context, and Product Thinking Shape Better SoftwareSeth Rosenbauer is the founder of a tool that uses AI to help engineers create better documentation—and, more importantly, the right thing, faster.But this conversation isn’t just about tooling.It’s about how context is the new currency in engineering. Why your team’s ability to understand what to build and why is more critical than ever. And how AI is changing the shape of product communication, technical documentation, and engineering ownership.Whether you lead a growing dev team or are trying to ship more with less, this one’s for you.Key Discussion PointsSeth’s journey: From PM to founder to doc tool builderWhy traditional documentation fails engineersThe real cost of unclear requirementsWhat AI can (and can’t) fix in engineering communicationHow better docs lead to better productsThe problem with "done"—and how teams miss the last 10%Building a culture of engineering ownershipLinks & ResourcesConnect with Seth Rosenbauer on LinkedInJoggrProduct Driven - Get the BookSubscribe to the Product Driven NewsletterWhat Smart CTOs Are Doing Differently With Offshore Teams in 2025Subscribe to the Global Talent SprintFull Scale – Build your dev team quickly and affordably

Matt is joined by Karell Ste-Marie, founder of The Serious CTO YouTube channel. Together, they tackle one of the biggest hidden challenges in software companies: the language and cultural barrier between engineers and executives.Karell and Matt break down why innovation is so rare in large organizations, why engineers and business leaders often talk past each other, and how the CTO role often becomes the critical bridge between the two worlds.Key Discussion PointsThe cultural resistance to change inside enterprisesHow introversion and communication style shape engineering cultureWhy the best CTOs speak “both languages”Lessons from mistakes made on the path to leadershipResources & LinksThe Serious CTO on YouTube – Karell’s channel where he shares insights on engineering leadershipProduct Driven - Get the BookSubscribe to the Product Driven NewsletterWhat Smart CTOs Are Doing Differently With Offshore Teams in 2025Subscribe to the Global Talent SprintFull Scale – Build your dev team quickly and affordably

Product management is being rewritten in real time, and AI is doing the editing.Matt sits down with Jerel Velarde, product manager at Full Scale Ventures, to discuss how AI is reshaping the relationship between PMs and engineering. We dive into what Jerel calls prompt prototyping, how expectations for product velocity have changed, and why the best PMs today are blending design, strategy, and code—all while staying laser-focused on validation over output.If you're a founder, CTO, or product leader trying to navigate the new frontier of product development, this one's for you.Key Discussion PointsIs “Product Manager” even the right title anymore?The new definition of PM: focused on outcomes, not artifactsHow PMs are using AI to validate fasterHow to lead product in a startup vs. a scale-upHow to think about MVPs when AI can build anythingResources & LinksConnect with Jerel on LinkedInProduct Driven - Get the BookSubscribe to the Product Driven NewsletterWhat Smart CTOs Are Doing Differently With Offshore Teams in 2025Subscribe to the Global Talent Sprint

Matt is joined by product and leadership consultant Randy Silver to unpack one of the most frustrating problems in product organizations: everyone knows where they want to go, but no one knows how to actually get there.Together they explore what causes this breakdown in execution, how companies drift from product strategy to dysfunction, and what strong leadership really looks like at scale.Key Discussion PointsWhy strategy is easy—execution is the problemWhy in-shitification happensThe three organizational dysfunctions Randy sees mostWhy autonomy without alignment failsThe real root of dysfunction: unclear product strategyWhat leaders can do right now to fix the messResources & LinksRandy Silver’s consulting work https://randysilver.comFollow Randy on LinkedIn Randy SilverGood Strategy Bad Strategy by Richard Rumelt Link to BookSubscribe to the Product Driven Newsletter: https://productdriven.com/newsletterWhat Smart CTOs Are Doing Differently With Offshore Teams in 2025: https://hirefullscale.com/offshore-hiring-guide

In this episode, Matt is joined by Laura Tacho, CTO at DX — one of the leading voices in developer experience research and tooling. Together, they unpack how AI is really affecting software development teams, why developer experience has a “marketing problem,” and why organizational friction — not technology — is the biggest productivity killer.If you’ve been wondering whether AI is living up to the hype in engineering teams, this conversation will give you the data, the reality, and the leadership takeaways you can act on today.Key Discussion Points[00:48] – What “Developer Experience” Really Means[02:55] – The Real Sources of Developer Friction[03:44] – Core Developer Experience Problems (Pre- and Post-AI)[05:46] – Clarity as a Competitive Advantage[07:25] – The Mistake of “Shit Shielding”[08:18] – How AI Raises the Stakes for Product Thinking[10:00] – The 10x Developer Myth’s Real Origin[11:30] – Measuring Developer Experience with the DX Index[14:00] – The Role of Leadership in Removing FrictionResources & Links DX – Research and tools for improving developer experience: https://getdx.com/Developer Experience Index  https://getdx.com/dxi-reportingSubscribe to the Product Driven Newsletter: https://productdriven.com/newsletterWhat Smart CTOs Are Doing Differently With Offshore Teams in 2025: https://hirefullscale.com/offshore-hiring-guide

AI can scaffold an app in seconds, but can it refactor that thousand-line React file when the first bug hits production? In this episode, I sit down with Brian Jenney software engineer and program owner of the coding bootcamp Parsity, to draw a hard line between “code that runs” and “code that lasts.” From mentoring career-switchers to stress-testing AI in real-world pipelines, Brian shares why craftsmanship and product judgment still beat copy-paste prompts.🔗 Essential Links (Start Here!):Full Episodes: https://product-driven.captivate.fm/episodesConnect with Matt Watson on LinkedIn: https://www.linkedin.com/in/mattwatsonkc/Subscribe to the Newsletter: https://newsletter.productdriven.com/Powered by Full Scale: https://fullscale.io/GET THE PRODUCT DRIVEN BOOK: https://productdriven.com/bookConnect with Brian on LinkedIn :https://www.linkedin.com/in/brianjenney/Check out Parsity here: https://www.parsity.io/Key Discussion Points:“You have to be smarter than the AI.” Why blindly shipping generated code is the fastest way to paint yourself into a technical-debt cornerThe hidden risk of non-deterministic models—like failing a simple “greater-than” check in production testsA training rule of thumb: no AI for your first months of study, then use it only to reinforce fundamentals—not replace themThe “house-of-cards” analogy for code quality and why maintainability still matters when AI writes the first draftHow Parsity’s tight-knit model turns plumbers, teachers, and even doctors into disciplined, product-minded engineers

Brittany Rastsmith, founder of Bloom Remote, specializes in helping startups scale by overcoming common bottlenecks. In this discussion, she explores how founders can shift from micromanaging to building trust with their teams. Brittany emphasizes the importance of creating visibility and accountability through simple systems like scorecards. She shares insights on documenting decision-making to ensure clarity, the significance of psychological safety for team ownership, and the need to prioritize real outcomes over busyness for true productivity.

The 10X Developer Decoded: Why Technical Co-Founders Are Startup Gold 💎In this revealing conversation, we unpack one of tech's most polarizing concepts while exploring the brutal realities of building technical partnerships in today's startup ecosystem. Host Matt Watson and Noah Lindner (ex-Airbnb engineer turned consultant) deliver unfiltered insights that challenge conventional wisdom about technical hiring and startup team dynamics.🔗 Essential Links (Start Here!):Get the Book: https://mybook.to/productdrivenNewsletter: productdriven.comConnect with Matt: https://linkedin.com/in/mattwatsonFull Scale Ventures: https://fullscaleventures.comGet the Offshore Hiring Guide: https://hirefullscale.com/offshore-hiring-guideYC Co-Founder Matching: https://ycombinator.com/cofounder-matchingThe Evolution of Engineering Excellence 🚀Redefining 10X: From Myth to MethodologyThe conversation opens with a fascinating transformation—how the once-toxic "10X developer" stereotype has evolved into a legitimate business advantage. Noah's perspective shift reveals something profound: the best engineers aren't just writing code faster; they're architecting workflows that eliminate friction entirely.Real-World 10X Impact:Before: 30-minute CI builds crushing team velocityAfter: 2-second feedback loops enabling continuous iterationResult: Exponential productivity gains through systematic optimizationThe Technical Co-Founder ParadoxMatt delivers a game-changing insight: "To really be a true technical co-founder, they've got to have the vision for what's being built... not just the technical vision, but the product vision."This distinction separates true startup partners from highly-paid order-takers—a critical differentiation in today's competitive landscape.Chapter Timestamps:00:00 - Deconstructing the 10X developer phenomenon08:30 - Technical co-founder vs. founding engineer dynamics16:45 - The four pillars of engineering leadership25:20 - Why big tech creates product-blind engineers32:15 - Navigating the golden handcuffs dilemmaThe Changing Startup LandscapeThe conversation reveals how technological democratization is reshaping co-founder dynamics. When any PM can create "lovable prototypes" using no-code tools, the bar for technical co-founders rises significantly. Success now requires scalable prototyping—building MVPs that can evolve rather than require complete rebuilds.The New Technical Leadership ModelMatt's four-quadrant framework provides clarity:Strategy: Long-term architectural visionOperations: Team efficiency and process optimizationProduct: User experience and market alignmentTechnical: Core engineering excellenceFor early-stage startups, product and technical mastery matter most—operations and strategy complexity come later.Have you experienced the "order-taker engineer" phenomenon? How did your team address it?What's your framework for evaluating technical co-founder potential beyond coding ability?How do you balance technical debt concerns with rapid iteration demands?Share Your Story: Tag us with your technical co-founder journey—the wins, failures, and lessons learned. Let's build a knowledge base for the next generation of technical partnerships.Subscribe for more unfiltered insights on technical leadership, product strategy, and startup team dynamics.

Kathy Keating, an industry veteran and co-founder of CTO Levels, shares invaluable insights into the evolving role of technology leadership. She discusses how modern CTOs must balance strategic and operational tasks, and the challenges they face at different organizational sizes. Kathy introduces her Four Pillars of Engineering Leadership framework, emphasizing adaptability amidst change. She also explores the importance of fostering a healthy company culture while scaling and the impact of AI on emerging software engineering careers.

In this discussion, Craig Ferril, an early reader of 'Product Driven' and collaborator with Matt Watson at Full Scale Venture, shares insights on transforming software development teams. They explore the 'Product Driven Model,' emphasizing the shift towards understanding user needs and fostering a culture of ownership. Key topics include the evolving role of engineering leaders, the challenges posed by AI, and the need for psychological safety to encourage innovation. This conversation is a treasure trove for those looking to adapt in a rapidly changing tech landscape.