Startup Hustle

Startup Hustle
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Startup Hustle is a podcast for entrepreneurs, by entrepreneurs.  With the mission of telling the real story of startups and entrepreneurs, topics range from funding to failure and beyond.  If you want to start, own, or build a business then you're in the right place.   

  1. Engineering Clarity in the Age of AI with Seth Rosenbauer

    VOR 6 STD.

    Engineering Clarity in the Age of AI with Seth Rosenbauer

    Engineering Clarity in the Age of AI: How Docs, Context, and Product Thinking Shape Better Software Seth 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 Points Seth’s journey: From PM to founder to doc tool builder Why traditional documentation fails engineers The real cost of unclear requirements What AI can (and can’t) fix in engineering communication How better docs lead to better products The problem with "done"—and how teams miss the last 10% Building a culture of engineering ownership Links & Resources Connect with Seth Rosenbauer on LinkedIn Joggr Product Driven - Get the Book Subscribe to the Product Driven Newsletter What Smart CTOs Are Doing Differently With Offshore Teams in 2025 Subscribe to the Global Talent Sprint Full Scale – Build your dev team quickly and affordably

    33 Min.
  2. Fixing the Language Barrier Between Engineers and Executives with Karell Ste Marie of The Serious CT

    22. JAN.

    Fixing the Language Barrier Between Engineers and Executives with Karell Ste Marie of The Serious CT

    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 enterprises How introversion and communication style shape engineering culture Why the best CTOs speak “both languages” Lessons from mistakes made on the path to leadership Resources & Links The Serious CTO on YouTube – Karell’s channel where he shares insights on engineering leadership Product Driven - Get the Book Subscribe to the Product Driven Newsletter What Smart CTOs Are Doing Differently With Offshore Teams in 2025 Subscribe to the Global Talent Sprint Full Scale – Build your dev team quickly and affordably

    37 Min.
  3. Prompt Prototyping, AI Vibes, and the New Rules of Product Management

    15. JAN.

    Prompt Prototyping, AI Vibes, and the New Rules of Product Management

    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 artifacts How PMs are using AI to validate faster How to lead product in a startup vs. a scale-up How to think about MVPs when AI can build anything Resources & Links Connect with Jerel on LinkedIn Product Driven - Get the Book Subscribe to the Product Driven Newsletter What Smart CTOs Are Doing Differently With Offshore Teams in 2025 Subscribe to the Global Talent Sprint

    29 Min.
  4. Why Teams Lose Their Way at Scale with Randy Silver

    8. JAN.

    Why Teams Lose Their Way at Scale with Randy Silver

    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 problem Why in-shitification happens The three organizational dysfunctions Randy sees most Why autonomy without alignment fails The real root of dysfunction: unclear product strategy What leaders can do right now to fix the mess Resources & Links Randy Silver’s consulting work https://randysilver.com Follow Randy on LinkedIn Randy Silver Good Strategy Bad Strategy by Richard Rumelt Link to Book Subscribe to the Product Driven Newsletter: https://productdriven.com/newsletter What Smart CTOs Are Doing Differently With Offshore Teams in 2025: https://hirefullscale.com/offshore-hiring-guide

    32 Min.
  5. How AI Is Really Impacting Developer Experience and the Real Productivity Problem with Laura Tacho

    18.12.2025

    How AI Is Really Impacting Developer Experience and the Real Productivity Problem with Laura Tacho

    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 Friction Resources & Links  DX – Research and tools for improving developer experience: https://getdx.com/ Developer Experience Index  https://getdx.com/dxi-reporting Subscribe to the Product Driven Newsletter: https://productdriven.com/newsletter What Smart CTOs Are Doing Differently With Offshore Teams in 2025: https://hirefullscale.com/offshore-hiring-guide

    30 Min.
  6. Why We Still Need Software Engineers in the Age of AI with Brian Jenney

    11.12.2025

    Why We Still Need Software Engineers in the Age of AI with Brian Jenney

    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/episodes Connect 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/book Connect 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 corner The hidden risk of non-deterministic models—like failing a simple “greater-than” check in production tests A training rule of thumb: no AI for your first months of study, then use it only to reinforce fundamentals—not replace them The “house-of-cards” analogy for code quality and why maintainability still matters when AI writes the first draft How Parsity’s tight-knit model turns plumbers, teachers, and even doctors into disciplined, product-minded engineers

    30 Min.
  7. Simple Systems that Let CTOs Delegate Ownership—and Still Sleep at Night with Brittany Rastsmith

    04.12.2025

    Simple Systems that Let CTOs Delegate Ownership—and Still Sleep at Night with Brittany Rastsmith

    If you’re running a startup, chances are you’re the bottleneck.  Brittany Rastsmith joins Product Driven to talk through why founders constantly end up in this trap and how to escape it. She works with early-stage companies through her consulting firm, Bloom Remote, and she's seen it all. We get into how to create clarity, visibility, and accountability across your team so you’re not stuck answering every question, solving every problem, or staying up all night wondering if anything is getting done.  If you want your team to take ownership and drive outcomes—not just check boxes—this episode is for you. [01:00] - Why being the bottleneck it's a stage  [02:30] - Choose your hard: micromanage or build trust  [07:30] - How to measure what matters [10:30] - Delegating doesn't work if you dump chaos  [14:30] - Explain your thinking if you want your team to carry it out  [16:00] - The power of decision logs and written rationale  [19:45] - Why psychological safety is key to team ownership  [21:30] - Rubber-stamping is the death of progress  [24:00] - Why most managers are untrained (and why that matters)  [28:00] - Productivity vs. busyness: where your team might be stuck  [29:15] - Inputs vs. outcomes: how to tell what's actually broken  [31:05] - Where to find Brittany and learn more about Bloom Remote Links & Resources: Brittany Rastsmith on LinkedIn:  Bloom Remote Get the Book: https://mybook.to/productdriven Newsletter: productdriven.com Connect with Matt: https://linkedin.com/in/mattwatson Get the Offshore Hiring Guide: https://hirefullscale.com/offshore-hiring-guide

    33 Min.
  8. Technical Co-Founders are Startup Gold with Noah Lindner

    27.11.2025

    Technical Co-Founders are Startup Gold with Noah Lindner

    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/productdriven Newsletter: productdriven.com Connect with Matt: https://linkedin.com/in/mattwatson Full Scale Ventures: https://fullscaleventures.com Get the Offshore Hiring Guide: https://hirefullscale.com/offshore-hiring-guide YC Co-Founder Matching: https://ycombinator.com/cofounder-matching The 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 optimization The 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 dilemma The 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 excellence For early-stage...

    30 Min.
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Startup Hustle is a podcast for entrepreneurs, by entrepreneurs.  With the mission of telling the real story of startups and entrepreneurs, topics range from funding to failure and beyond.  If you want to start, own, or build a business then you're in the right place.   

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    Startup Hustle
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