In this episode of Startup Hustle, Matt Watson interviews Mark Roberge, a former HubSpot executive and current venture capitalist, about his journey from engineering to sales and the importance of scaling startups. Mark discusses the genesis of HubSpot, the significance of sales in startups, and the concept of product-market fit. He emphasizes the need for customer research, avoiding false positives in feedback, and identifying the...

In this episode of Startup Hustle, Matt Watson interviews Krishna Oza, founder and COO of Git Hired, discussing the challenges of hiring software engineers, particularly for startups. Krishna shares his personal experiences that led to the creation of GitHired, an AI-driven platform designed to help startups find the right technical talent based on proof of work. The conversation delves into the unique needs of early-stage develope...

In this episode of Startup Hustle, Matt Watson interviews John Morlan, founder and CEO of Smarter Risk, about the transformative impact of AI on startups. John shares his journey of integrating AI into his business, enhancing productivity, and improving collaboration with developers. He discusses the balance between product-led and sales-led growth strategies, the importance of knowledge management, and the challenges of achieving ...

In this episode, Matt Watson interviews Matt Haycox, an experienced entrepreneur who shares insights from his 25 years in business, focusing on capital raising, the challenges of entering the tech space as a non-technical leader, and the impact of AI on business development. Haycox discusses his journey from traditional businesses to tech ventures, emphasizing the importance of understanding both technical and commercial aspects of...

What happens when you mix creative agency chaos with world-class engineering? You get teams that don’t just write code—they own the product.

In this episode, I’m talking with David Mitchell, CTO at VML, one of the biggest creative agencies on the planet. With thousands of engineers and global clients like Wendy’s and United Airlines, David’s teams are building things that most devs only dream of—and doing it without getting buried i...

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 e...

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...

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...

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 Points

Why strateg...

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...

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...

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...

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 ...

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!):&nb...

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: h...

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 thin...

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 an...

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. B...

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 enhanc...