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

    18 DEC

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

    11 DEC

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

    4 DEC

    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
  4. Technical Co-Founders are Startup Gold with Noah Lindner

    27 NOV

    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
  5. CTO Levels and the Path to Strategic Tech Leadership with Kathy Keating

    24 JULY

    CTO Levels and the Path to Strategic Tech Leadership with Kathy Keating

    From Coding to Catalyst: The Evolution of Technology Leadership 🚀 Journey through the transformation of modern CTOs with industry veteran Kathy Keating, who shares battle-tested insights from scaling teams of 2 to 450+ engineers. This episode unravels the complex tapestry of technology leadership, exploring how yesterday's code-focused roles have evolved into today's strategic business catalysts. 🔗 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 The Leadership Evolution Story 📖 The Great Divide: Once upon a time, software engineers were the product owners, customer advocates, and technical architects all rolled into one. They flew across continents to understand telecom fraud patterns, immersed themselves in customer operations for weeks, and returned with deep domain expertise. Today's specialized world has created powerful capabilities—but at what cost? The Four Pillars of Engineering Leadership: Matt introduces a provocative framework suggesting no one masters all four domains: Strategic visioning, Operational excellence, Technical depth, and Product intuition. The conversation challenges us to identify our strengths while building systems that compensate for our natural limitations. Behind the Framework: CTO Levels Decoded 🔍 Kathy reveals the methodology behind assessing technology leadership maturity—from solo programmer (Level 0) to industry thought leader (Level 10). Each level demands mastery of previous foundations while introducing new complexities like acquisitions, strategic partnerships, and organizational transformation. The Assessment Reality: A comprehensive 50-question evaluation generating 60-page strategic roadmaps. Hundreds of leaders have used this framework to identify gaps and accelerate growth—proving that systematic development beats trial-and-error learning. Chapter Timestamps: 00:00 - Opening: Two Authors, One Mission  02:14 - Defining Modern CTO Reality  04:11 - The Four-Type Leadership Framework  07:21 - CTO Levels: Decoding the Hierarchy  09:25 - Career Path Truth: How Do You Actually Become a CTO?  16:58 - Strategic Advice: The Power of Starting Small  17:52 - Then vs. Now: 20 Years of Engineering Evolution 22:03 - The Product-Engineering Divide Crisis  26:12 - AI Revolution: Promise and Peril  32:44 - Resources: CTO Levels and Liquid Book Overview  33:09 - Final Thoughts and Next Steps Which of the four engineering leadership types resonates most with your current role—Strategic, Operational, Technical, or Product? Share your experience in the comments and let's discuss how to build complementary teams that cover all bases.

    34 min
  6. Inside 'Product Driven': Why This New Book is Every Engineering Leader's Must-Read

    17 JULY

    Inside 'Product Driven': Why This New Book is Every Engineering Leader's Must-Read

    Product Driven: Building Software Teams That Ship Value 🚀 In this special book launch episode, we dive deep into the intersection of engineering leadership, product thinking, and the transformative impact of AI on software development. Join Matt Watson and Craig Ferril as they explore the revolutionary "Product Driven Model" and why traditional development approaches are becoming obsolete. 🔗 Essential Resources: Get the Book: https://a.co/d/100RmwC 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 Key Discussion Highlights: 🎯 The Product Driven Model (Five Core Components)Vision: Understanding the "why" behind every decisionFocus: Keeping customer outcomes at the centerClarity: Providing just enough context without overwhelmingShared Ownership: Distributing responsibility across teamsCourage: Creating psychological safety for innovation 🤖 AI's Leadership ChallengeEngineering bottlenecks are shifting from throughput to directionTeams going "2x faster in the wrong direction" create bigger problemsLeadership must evolve from requirement-feeders to vision-communicatorsThe rise of "low-code thinking" in traditional development 🎯 From Individual Contributors to LeadersThe transition from "doing" to "enabling others to do"Four types of engineering leadership: Strategic, Operational, Technical, and ProductWhy most leaders aren't good at all four (and shouldn't try to be) Chapter Timestamps: 00:00 - Book Launch Introduction & "Find Your Craig" 08:16 - Why AI Makes Product Thinking Critical 15:03 - The Death Spiral of Internal Focus 18:07 - Creating Cultures of Courage vs. Fear 23:14 - The Five Components of Product Driven Model 32:40 - Future of Engineering Leadership 37:22 - Closing the Feedback Loop with Introverted Teams 💡 Key Takeaways: For Engineering Leaders: Stop being the bottleneck - build teams that don't need youCreate environments where "calling the baby ugly" is celebratedFocus on making other people more productive For Product Teams: Shift from feature factories to outcome-driven developmentEmbrace the "win or learn" mentalityConnect every technical decision to customer value For Organizations: AI won't solve leadership problems - it will expose themCulture and strategy must work in tandemThe future belongs to teams that think like product owners The conversation reveals a fundamental shift happening in software development. As AI democratizes code creation, the competitive advantage moves from "how fast can we build" to "what should we build and why." Teams that master this transition will thrive; those that don't will...

    42 min
  7. The Engineering Leadership Book That Actually Shows You How to Build Product-Minded Teams

    15 JULY

    The Engineering Leadership Book That Actually Shows You How to Build Product-Minded Teams

    Product Driven: The Book Launch - A Software Leader's Journey to Creating High-Performance Teams 📚 After months of intensive writing and years of industry experience, Matt Watson unveils his groundbreaking book "Product Driven" - a comprehensive guide for engineering leaders seeking to build teams with a genuine product mindset. This isn't just another business book; it's a practical roadmap for transforming how software teams think, work, and deliver value. In this revealing first look, Matt shares the personal journey that led to creating this essential resource for the tech industry. Drawing from his extensive career building and scaling software products, he addresses a critical gap in leadership literature - how to actually build and manage teams that think like product owners, not just code executors. 🔗 Essential Resources:Get the Book: https://a.co/d/100RmwC 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 Key Discussion Points: The evolution from developer conference speech to comprehensive leadership guideWhy product mindset separates high-performing developers from the restThe cultural transformation required for sustainable team successPractical frameworks for engineering leaders to implement immediatelyThe 500-hour writing journey and lessons learned Chapter Timestamps: 00:00 - The Big Reveal: First Look at Product Driven 00:22 - The Origin Story: From Conference Speech to Book 01:30 - The Culture Revolution: Why Leadership Matters 02:38 - The Writing Process: 500 Hours of Insights Ready to Transform Your Team? Share your biggest leadership challenge in the comments - what's preventing your developers from thinking like product owners? Let's discuss practical solutions that actually work in real engineering environments.

    4 min
  8. Rethinking Requirements When Engineers Are No Longer the Bottleneck with Chris Rickard

    10 JULY

    Rethinking Requirements When Engineers Are No Longer the Bottleneck with Chris Rickard

    Breaking Through Requirements Hell: How AI is Revolutionizing Software Development 🚀 In this compelling exploration of technological transformation, host Matt Watson connects with Chris Rickard, founder of UserDoc, broadcasting from Vietnam. Their conversation unveils a profound shift happening across the software industry—one where artificial intelligence is fundamentally reshaping the relationship between business stakeholders and development teams. What emerges is a fascinating paradox: as AI accelerates coding capabilities, the critical constraint shifts from "how do we build it?" to "what exactly should we build?" Chris's journey from software engineer to product innovator illustrates this transformation, revealing how traditional bottlenecks are being reimagined through AI-powered requirements management. 🔗 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 our Newsletter: https://fullscaleteam.com/newsletter  Get our FREE Ebook: https://fullscaleteam.com/productfirstteams  Powered by Full Scale: https://fullscale.io/ Download the FREE Offshore Hiring Guide: https://hirefullscale.com/offshore-hiring-guide UserDoc: https://userdoc.com Chris Rickard on LinkedIn: https://www.linkedin.com/in/chrickard/ Key Discussion Points: AI-Powered Requirements Creation: How UserDoc accelerates requirements by 50-70% while maintaining human oversightReverse Engineering Legacy Systems: Converting complex source code (including COBOL) into understandable business featuresThe Shifting Development Bottleneck: Why clarity becomes paramount when AI makes development fasterIntegration with Modern Workflows: Connecting requirements directly to AI coding tools like Cursor and GitHub Copilot Chapter Timestamps: 00:00 - The Universal Developer Dilemma02:28 - Genesis of UserDoc07:57 - Beyond Product Managers: Who Really Needs This14:40 - Technical Challenges of Code Analysis22:44 - The Great Bottleneck Shift27:04 - Pricing and Market Accessibility Ready to break free from requirements chaos and accelerate your development workflow? The conversation with Chris Rickard reveals a pivotal moment in software development—where AI amplifies human potential rather than replacing it.  Share your own requirements management challenges in the comments below. How has AI changed your development process? What bottlenecks are you experiencing as coding becomes more automated?

    31 min
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Ratings & Reviews

5
out of 5
2 Ratings

About

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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  • Creator
    Startup Hustle
  • Years Active
    2017 - 2025
  • Episodes
    1.4K
  • Rating
    Explicit
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    © 2024 Startup Hustle
  • Show Website
    Startup Hustle

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