Startup Hustle
Startup Hustle

Startup Hustle

Startup Hustle

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Episodes

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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.   

Recent Episodes

How AI Is Really Impacting Developer Experience and the Real Productivity Problem with Laura Tacho
DEC 18, 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 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
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29 MIN
Why We Still Need Software Engineers in the Age of AI with Brian Jenney
DEC 11, 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/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
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29 MIN
Simple Systems that Let CTOs Delegate Ownership—and Still Sleep at Night with Brittany Rastsmith
DEC 4, 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 RemoteLinks & Resources:Brittany Rastsmith on LinkedIn: Bloom RemoteGet the Book: https://mybook.to/productdrivenNewsletter: productdriven.comConnect with Matt: https://linkedin.com/in/mattwatsonGet the Offshore Hiring Guide: https://hirefullscale.com/offshore-hiring-guide
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33 MIN
Technical Co-Founders are Startup Gold with Noah Lindner
NOV 27, 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/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.
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30 MIN
CTO Levels and the Path to Strategic Tech Leadership with Kathy Keating
JUL 24, 2025
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/productdrivenNewsletter: productdriven.comConnect with Matt: https://linkedin.com/in/mattwatsonFull Scale Ventures: https://fullscaleventures.comGet the Offshore Hiring Guide: https://hirefullscale.com/offshore-hiring-guideThe 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 Evolution22:03 - 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 StepsWhich 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.
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34 MIN