Episodes

"Back in the 1900s when I was crossing the Great Plains in a covered wagon, programming in the back, the cover headline was: Software Development is Dead." I talked with Anthony Jackson, a CTO with 30 years across healthcare tech and enterprise software and author of the Architecture Protocol series, on Startup Hustle this week. Anthony is the creator of LeadershipOS, a framework for building teams that keep running when the leader isn't in the room. Here's what you'll get out of it: ⚡ Why "s...

I don't view engineers being out of a job. I view software engineers finally coming back to a real job." I talked with Adrian Gutierrez, co-founder of Ledgre, on Startup Hustle this week. Ledgre is an AI-native accounting platform built specifically for real estate investors, putting agentic AI to work doing the bookkeeping instead of handing you one more piece of software to manage. Here's what you'll get out of it: ⚡ Why he was the startup's bookkeeper by hand for a year before writing a li...

Most engineering teams are still optimizing for the wrong thing. They chase the speed of code when the real bottleneck is the speed of context. Matt Watson and Eban Bisong, founder and CEO of Senvi, get into what actually changes when AI moves from a coding tool to a teammate. Eban has spent his career as a founding engineer, and his approach is hands-on: don't tell skeptical engineers AI works, show them, every standup, until the pushback turns into excitement. At Park DNA he built "RTD2," an ...

Most people are already asking AI about their health. Almost none of them believe the answers. Around 40% use it to make wellness choices, but fewer than 5% trust what it says. Matt Watson and Josh Anthony, CEO of Nlumn, dig into why. Josh has spent 25 years in food and nutrition, and his take is blunt: trust drops fast as the question gets serious, from a recipe to a diagnosis, and the fix isn't a smarter chatbot. It's pairing the data with a human people actually trust. They cover what's real...

Matt Watson sits down with Beth Epperson, founder and CEO of Legacy Purpose, here in the Kansas City area. Beth came up through marketing and branding, including the brand launch for Hyvee Arena, before deciding to build something of her own. Her company is built around two products. Aligned Legacy measures how people think in real time and helps teams see how aware, connected, and aligned they actually are. HICMIT, or Wisdom Illuminated, keeps a company's knowledge governed and accurate so not...

Data centers are multiplying fast, and the energy demands are staggering. Matt Watson sits down with Tim Tarver, founder and CEO of Exceed Geo Energy, to talk about one of the most underrated power sources in the conversation: geothermal. Tim breaks down how his company is adapting drilling technology from the oil and gas industry to generate clean, baseload energy almost anywhere in the country, why geothermal outlasts solar and wind by decades, and how it could be the right fit for the next wa...

Eric Ries wrote The Lean Startup. Sold 2 million copies. Helped hundreds of people build companies from nothing. Now he's back with a harder question: why do so many of those companies eventually go bad? In this episode, Matt Watson sits down with Eric to talk about his new book Incorruptible—a deep dive into the invisible forces that corrupt organizations, why profit-maximization becomes pathological, and what it actually takes to build a company that stays great. They get into why the stage-...

Most founders get the order wrong. They build for two years, then ask a marketer how to sell it. Connie Lund flipped the script. She started Zaboom with no dev team, no code background, and no VC funding. What she had was 50+ years of combined marketing and product experience, a GoHighLevel account, and a willingness to break things at 2 a.m. on a Sunday. In this episode, Connie walks Matt through how she built a working voice AI product for insurance agencies—using N8N, GoHighLevel, and Clau...

Most product managers are just project managers with a fancier title. They make zero real decisions, answer to everyone, and wonder why nothing ships on time. Willis Jackson has been building product teams for over a decade. He's blacklisted entire companies from his hiring pool. And he moved to the Bay Area to measure himself against the best—only to find out nobody there really knows how to do product either. In this episode, Willis and I get into why product thinking is now the most valuabl...

Most founders think investors bet on ideas. They don't. Dave Lambert has funded over 2,000 companies through RightSide Capital, and he's seen this pattern play out thousands of times. Great product. No revenue traction. Wrong ask, wrong timing. Automatic no. In this episode of Startup Hustle, Matt sits down with Dave to break down how RightSide Capital evaluates startups differently than traditional VCs. No subjective analysis. No months of diligence. Just data, profiles, and a decision in abo...

Matt Watson sits down with Mohan Reddy, serial entrepreneur and Chief Scientist at Cornerstone AI Labs, to explore how AI is fundamentally reshaping the way we think about work, skills, and human potential. Mohan shares the origin story of Skyhive—a workforce intelligence platform built to reskill and upskill people at a global scale—and how its acquisition by Cornerstone brought that mission to a larger stage. The conversation digs into why AI doesn't eliminate skills but transforms them, the ...

AI is changing how kids learn. But are schools ready? Katie Boody Adorno is the founder and CEO of LeanLab Education. She's spent 13 years trying to close the opportunity gap in public education. In this episode, she and Matt break down how COVID widened learning disparities, why high-dosage tutoring works but doesn't scale, and how AI is now lowering that cost. They also get into what it takes to prepare kids for a world where AI handles most of the knowledge work. Listen to the full episode ...

Zach Klempf is back! He joined Matt Watson on one of the early episodes of the show. Now, Zach is president of AutoManager, a private equity group with five automotive software companies under its umbrella. In this episode, Zach and Matt get into how AI is making senior engineers more productive. They talk about why offshore teams tend to adopt it more slowly, and where vibe coding breaks down when you're running production software with real integrations. They also get into why simple SaaS pro...

In this episode, entrepreneur Chris Jones shares his journey from personal tragedy to building MatchRite Care, a healthcare data integration platform. He discusses product-market fit, scaling strategies, and the importance of community and continuous learning in entrepreneurship. ⏱️ Episode Breakdown 00:00 The Entrepreneurial Journey Begins 02:54 The Birth of MatchRite Care 06:07 Navigating Product Fit and Market Strategy 09:04 The Importance of Data Sharing in Healthcare 12:01 Scaling vs. ...

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 ideal customer profile. Mark also shares insights on scaling str...

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 developers, the importance of product thinking, and how GitHired identifi...

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 product-market fit. The conversation emphasizes the necessity of ...

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 business. He also highlights the value of learning from mistakes...

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 in bureaucracy. We break down what it really takes to foster cr...

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 communicat...

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 Points The cultural resistance to ...

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 ...

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 strategy is easy—execution is the problem Why in-shitification happens The ...