Startup Hustle

Startup Hustle
  • 4.6 (228)
  • ENTREPRENEURSHIP
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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. CTO Levels and the Path to Strategic Tech Leadership with Kathy Keating

    JUL 24

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

    JUL 17

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

    JUL 15

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

    JUL 10

    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
  5. How Boddle's Product-Driven Approach Built Educational Games That Kids Ask Parents to Buy with Clarence Tan

    JUL 3

    How Boddle's Product-Driven Approach Built Educational Games That Kids Ask Parents to Buy with Clarence Tan

    Learning Through Play: How Boddle Built Educational Games That Kids Actually Want In this insightful conversation, Matt Watson talks with Clarence Tan, founder and CEO of Boddle Learning, about their journey building educational games that have reached over 10 million users. Clarence shares how they tackled the classic problem of educational games - how to make them as engaging as regular games while maintaining educational value. By creating fun games first and then "sneaking in" learning content, Boddle has found success in the competitive educational technology space. The most valuable lesson? Get out of the office and actually watch users interact with your product. Rather than spending money on complex analytics, the Boddle team discovered their biggest product issues simply by visiting classrooms and observing how kids used their app. Clarence also shares how they eventually cracked the monetization code by understanding that parents were buying subscriptions not because they understood the educational benefits, but because their kids wanted the in-game items. 🔗 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://newsletter.productdriven.com/ Powered by Full Scale: https://fullscale.io/ GET THE PRODUCT DRIVEN BOOK: https://productdriven.com/book Check out Boddle here: https://www.boddlelearning.com/ Key Discussion Points: 🎮 Building educational games that are genuinely fun first 🧠 How Boddle "sneaks in" learning content after establishing engaging gameplay 💰 The journey from zero users to 10 million through COVID and beyond 📊 Why watching actual users beats fancy analytics tools 🔑 The monetization breakthrough: understanding kids are the real decision makers 🚀 Pivoting from building many games to focusing on the most successful one 📱 How Boddle connects with both teachers and parents Chapters: 00:00 - Introduction and Welcome 00:46 - Origins of Boddle Learning 02:08 - Making Education Fun Through Games 04:17 - Early Funding and Productization 05:36 - Impact of COVID on Growth 07:42 - Getting on the White House Educational Resources List 08:19 - Server Challenges with Rapid Growth 09:04 - Moving to Tulsa for VC Funding 10:30 - The "Leaky Bucket" Discovery 11:21 - Monetization Challenges 13:57 - Finding the Most Popular Game Mode 14:51 - The Pet Battle Game Success 15:58 - NFT Experiment Mistakes 16:52 - Keeping Education in Fun Games 18:45 - The Power of Classroom Observation 20:47 - First-Time User Experience Issues 22:32 - Learning to Sell to Parents Through Kids 25:40 - Tapping Into the Entertainment Wallet 26:45 - Boddle Bucks and Future Growth 27:38 - Impact and Educational Value Ready to transform your child's screen time into learning time? Visit https://www.boddlelearning.com/ to try their educational games that kids actually want to play!

    29 min
  6. How Feedback Loops Transform Development Efficiency with Ashley Davis

    JUN 26

    How Feedback Loops Transform Development Efficiency with Ashley Davis

    Feedback-Driven Development: Optimizing Your Software Engineering Process In this enlightening conversation with author Ashley Davis, Matt Watson explores the concept of feedback-driven development and how it shapes effective software engineering practices. Ashley, author of "Bootstrapping Microservices" and the upcoming "The Feedback-Driven Developer," shares valuable insights on how developers can leverage feedback loops to enhance their productivity, make better decisions, and deliver more value to customers. They discuss the shifting landscape of software development in the age of AI, the importance of personal feedback systems, and why understanding product priorities is crucial for modern developers. 🔗 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/ GET THE PRODUCT DRIVEN BOOK: https://productdriven.com/book Ashley Davis on Twitter: @ashleydavis75 "Bootstrapping Microservices" book: Manning.com/books/bootstrapping-microservices-with-docker-kubernetes-and-terraform "The Feedback-Driven Developer" (Early Access): Manning.com Key Discussion Points: 🔄 The concept of personal feedback loops in the development process 🎯 How prioritizing by "value over cost to deliver" leads to better decisions 🔍 The critical importance of getting clarity before diving into code 🚀 Why prototyping is one of the most effective feedback mechanisms 🤖 How AI is shifting the bottleneck from engineering to product decision-making ⚠️ The pitfall of "moving fast in the wrong direction" with AI assistance 🧩 Techniques for self-review and maintaining working code 🏗️ When microservices architecture makes sense (and when it doesn't) Chapters 00:00 - Introduction and Welcome 00:25 - The Experience of Being a Tech Book Author 00:53 - Origins of "The Feedback-Driven Developer" Book 02:11 - Defining "Feedback" in Software Development 03:52 - The Importance of Understanding Trade-offs 05:35 - Ensuring You're Working on the Right Thing 07:34 - Getting Feedback on Implementation Approaches 09:06 - Clarity as the Fuel of Software Development 11:16 - AI's Impact on the Software Development Bottleneck 13:13 - Why the Best Developers Think Like Product Owners 14:54 - Process Theater vs. Value Delivery 16:19 - Building Feedback into Your Development Loop 17:23 - Production Monitoring and Performance Feedback 19:32 - Key Insights and Aha Moments from the Book 22:44 - Developers QA-ing Their Own Code 25:21 - When to Use Microservices Architecture 27:43 - Book Information and Closing Thoughts Ready to transform your development process with effective feedback systems? Get early access to "The Feedback-Driven Developer" at a...

    29 min
  7. Product-Led Growth vs. VC Funding: Lessons from 25 Bootstrapped Startups with John Rush

    JUN 19

    Product-Led Growth vs. VC Funding: Lessons from 25 Bootstrapped Startups with John Rush

    Bootstrapping vs VC: John Rush on Building 25 Successful Products 🚀 In this enlightening episode of Product Driven, host Matt Watson sits down with serial tech entrepreneur John Rush. Known for his prominent presence on social media platforms like Twitter (X) and LinkedIn, John shares his journey from VC-backed companies to successfully bootstrapping 25 different startups over the past 15 years. The conversation explores the stark differences between venture-backed and bootstrapped business models, the importance of UX in product development, and how focusing on solving specific problems has led to his remarkable success. John provides valuable insights on identifying your strengths as a founder, why empathy for users matters more than code quality, and his unique approach to product development that allows him to launch multiple successful tools with minimal failure rapidly. His clear vision of building a lasting company that helps bootstrappers achieve a better work-life balance inspires developers considering the entrepreneurial path. 🔗 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://newsletter.productdriven.com/ Powered by Full Scale: https://fullscale.io/ Chapters: 00:03 - Introduction to John Rush 00:31 - Thoughts on the "Indie Hacker" term 02:06 - VC-backed vs. Bootstrapped business models 04:30 - Creating and managing 25 different products 06:23 - Product success rate and failure assessment 08:32 - The seven tools driving 90% of revenue 11:22 - Competing in crowded markets 13:53 - Technology stack and code sharing across products 15:50 - The critical importance of UX in product design 23:19 - Approach to advertising and marketing 25:48 - Advice for software engineers considering entrepreneurship 30:57 - Long-term vision and goals 32:31 - Final words of wisdom Transform your product development journey! Dive deeper into the entrepreneurial mindset that drives successful tech innovations. Whether you're a seasoned founder or just beginning your startup adventure, these resources will help you navigate the path with confidence and vision. 🚀

    33 min
  8. AI Adoption Strategies: Inspiring Developer Teams to Embrace Intelligent Tools with Senad Santic

    JUN 12

    AI Adoption Strategies: Inspiring Developer Teams to Embrace Intelligent Tools with Senad Santic

    AI and Agency Evolution: Navigating the Future of Software Development 🚀 In this thought-provoking episode of Product Driven, Matt Watson welcomes Senad Santic, owner of Zendev software development agency and founder of LinkBound. They dive deep into how AI is reshaping software development agencies, training strategies for developers in this evolving landscape, and the challenges of diversifying from agencies into SaaS products. Both entrepreneurs share valuable insights on balancing innovation with realistic business concerns while navigating the rapidly changing technological environment. 🔗 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/ Key Discussion Points: The economic impact on dev agencies across different regions and markets How AI tools like Lovable are changing the MVP development landscape The increasing complexity of software development careers and adaptation challenges Strategies for training developers to embrace AI while developing product thinking The practical challenges of building SaaS products within an agency model Chapters: 00:00 - Introduction and Background 03:08 - Economic Impact on Development Agencies 05:38 - AI's Impact on Development Businesses 07:16 - AI Tools for MVP Development 10:47 - The Reality of Using AI for Rapid Prototyping 15:28 - The Growing Complexity of Software Development 18:34 - Training Developers in Product Thinking and AI 24:24 - Why Business People Won't Replace Developers 28:27 - Building SaaS Products Within an Agency Model 33:23 - Structuring Teams for Product Development 35:06 - Conclusion and Parting Thoughts Don't let your team fall behind in the AI revolution! The agencies that embrace these tools today will dominate the market tomorrow. Start your AI adoption journey now and transform how your developers work.

    37 min
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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
    1.3K
  • Rating
    Clean
  • Copyright
    © 2024 Startup Hustle
  • Show Website
    Startup Hustle

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