The Builders Podcast

Subscriptions sound simple… until you try to build them.In this episode, we sit down with a builder who turned one of the most frustrating parts of app development into a platform now powering monetization for tens of thousands of apps. From early days growing up in Spain to taking a leap into Silicon Valley, this is a story about following curiosity, taking risks, and recognizing when a problem is bigger than it first appears. What started as an internal challenge… billing, analytics, experimentation… quickly revealed itself as a widespread pain point across the entire app ecosystem. Instead of working around it, Miguel and his co-founder leaned in, building a solution they wished existed. That decision became RevenueCat. We go beyond the origin story and into what it actually takes to build and scale something like this… from infrastructure and team building to culture, communication, and constantly evolving as a founder. This is a grounded look at building something real… by solving a problem developers didn’t want to touch. Key Takeaways Subscriptions are deceptively complex and become a major challenge at scale The best opportunities often come from problems you’ve experienced firsthand If developers avoid building something, it might be worth paying attention to What gets you started won’t be what helps you scale Strong communication is essential in remote, distributed teams Founders must evolve constantly and focus on solving the biggest problem at hand

Subscriptions sound simple… until you try to build them.In this episode, we sit down with a builder who turned one of the most frustrating parts of app development into a platform now powering monetization for tens of thousands of apps. From early days growing up in Spain to taking a leap into Silicon Valley, this is a story about following curiosity, taking risks, and recognizing when a problem is bigger than it first appears. What started as an internal challenge… billing, analytics, experimentation… quickly revealed itself as a widespread pain point across the entire app ecosystem. Instead of working around it, Miguel and his co-founder leaned in, building a solution they wished existed. That decision became RevenueCat. We go beyond the origin story and into what it actually takes to build and scale something like this… from infrastructure and team building to culture, communication, and constantly evolving as a founder. This is a grounded look at building something real… by solving a problem developers didn’t want to touch. Key Takeaways Subscriptions are deceptively complex and become a major challenge at scale The best opportunities often come from problems you’ve experienced firsthand If developers avoid building something, it might be worth paying attention to What gets you started won’t be what helps you scale Strong communication is essential in remote, distributed teams Founders must evolve constantly and focus on solving the biggest problem at hand

AI tools are moving fast… but governance isn’t keeping up. In this episode, Matt sits down with AI strategist Jill Heinze to explore what happens when generative AI moves from experimentation into real-world deployment. From chatbots in regulated industries to internal productivity systems, the conversation focuses on the risks that emerge once AI starts interacting with real users and real data. Jill shares how her background in user research led her to focus on anticipatory design and AI governance. Instead of reacting after something breaks, her approach centers on identifying risks early. That includes understanding data flow, training inputs, model behavior, and the unintended consequences that can surface when AI systems are deployed at scale. Together, Matt and Jill explore the shift from prototype thinking to production-ready AI. The discussion highlights the importance of building responsibly, protecting sensitive data, and designing systems that account for both opportunity and risk. For builders, agencies, and teams experimenting with AI, this episode offers a grounded perspective on what it really means to ship AI safely. Key Takeaways Generative AI introduces new risks that require governance before deployment Once sensitive data enters training pipelines, it’s difficult to remove AI systems become more complex as they move from prototype to production Anticipatory design helps teams identify risks early in development Data flow and architecture decisions matter as much as model choice Responsible AI is not just enterprise thinking, it applies to builders too

Michael Haynes shares his journey from large corporate strategy roles to building a practical go-to-market approach for small and mid-sized B2B firms. After years working in banking, consulting, and telecommunications, he saw firsthand how structured growth strategies helped large organizations scale. But when he transitioned to working with smaller professional service firms, he realized those same ideas rarely translated directly. The conversation explores how Michael adapted corporate B2B strategy into something practical and actionable. Instead of complex research and large segmentation projects, he focuses on clarity. Identifying the right markets, understanding buyers, aligning services, and building cross-functional growth plans. The result is a structured yet realistic approach that smaller firms can actually execute. Throughout the episode, Michael also reflects on leaving corporate, starting his own consulting practice, and the lessons learned along the way. From landing his first client to building a sustainable pipeline, the discussion centers on the fundamentals of building a growth strategy that works in the real world. Key Takeaways Corporate growth principles still apply to small B2B firms when simplified Market clarity is the foundation of effective go-to-market strategy Growth comes from acquisition, retention, and expansion, not just new clients Choosing target markets is more powerful than trying to serve everyone Small firms need practical strategy, not enterprise complexity Builders must balance delivery work with intentional business development

What makes people actually use a product… and keep coming back?In this episode, Matt sits down with Tetiana Kobzar to explore behavioral design, gamification, and what it really takes to create products people love to use. Drawing from her background in development and product design, Tetiana explains how understanding human behavior can dramatically change how products are built, moving teams beyond feature-driven thinking into experience-driven outcomes. They dive into the psychology behind engagement, how gamification works when applied thoughtfully, and why small UX decisions can have outsized impacts on adoption and retention. The conversation also explores how builders can reduce friction, create motivation loops, and design products that align with how people actually behave, not how we assume they should behave. If you’re building software, digital tools, or user experiences of any kind, this episode offers a practical look at designing with human behavior in mind… and why that mindset often separates products that get ignored from products people genuinely enjoy using. Key Takeaways Behavioral design focuses on how people actually behave, not how we expect them to Gamification works best as subtle motivation, not superficial rewards Small UX changes can dramatically improve engagement and adoption Feature-heavy products often fail without behavioral thinking Designing for momentum and habit formation improves retention Builders should start with user motivation before designing interfaces

Many great software tools begin with a simple starting point: a manual process that works. In this episode, Matt welcomes back Joel Salomon to talk about the journey of turning his proven stock-screening framework into a scalable software system. After years of teaching clients his five-step process for evaluating companies, Joel began exploring how technology could help automate the research and deliver insights more efficiently. What followed was a builder’s journey that many founders will recognize. From manually screening hundreds of companies each quarter to experimenting with AI tools and working with early developers, Joel shares the real-world challenges of translating personal expertise into working software. Along the way, Matt and Joel unpack the lessons that come from building technology when you’re not a developer. The conversation explores documentation, outsourcing development, managing expectations, and the patience required to turn a good idea into a functioning system. For builders thinking about turning their own processes into software, this episode offers a practical look at what that journey can actually look like. Key Takeaways Many scalable tools begin as manual systems that prove themselves first Turning expertise into software requires translating human judgment into clear logic AI tools can accelerate research but still require careful verification Outsourcing development requires strong communication and iteration Builders often discover the real complexity of software during the building process

In this solo episode of The Builders, Matt Levenhagen reflects on a discovery that took him back more than three decades. While organizing old notebooks, artwork, and personal archives from the early 1990s, he uncovered a series of audio journals he recorded between 1991 and 1993. Listening back to those recordings today offers a rare glimpse into the mindset of his younger self, a 20-year-old trying to understand who he was and what direction his life might take. What emerges from those recordings isn’t a clear plan for the future. It’s something far more familiar to most builders: uncertainty, curiosity, experimentation, and the slow process of becoming. Matt shares how revisiting these journals reframed many experiences that once felt like failures or detours, revealing how those moments ultimately shaped the path he would follow. The episode also explores how modern AI tools helped him analyze these journals in a new way. By surfacing patterns and themes across decades of personal reflection, AI became more than a productivity tool. It became a way to understand the story behind the builder he has become, and to imagine how others might use similar tools to better understand their own paths. Key Takeaways • The path to becoming who you are rarely follows a straight line. • Experiences that once felt like failures often become essential parts of the story later. • Revisiting old journals or memories can reveal patterns in your thinking across decades. • AI can be used as a reflection tool to analyze your own life experiences. • Understanding your past can bring clarity to the path you are building today.

In this episode of The Builders, Matt sits down with Jill Heinze, founder of Saddle-Stitch Consulting, to explore an unexpected but deeply logical career evolution: from research librarian to AI governance architect. Jill’s journey began with a love of history and archival research. That passion led her into academic librarianship, where she discovered that modern libraries are not just about books. They are complex digital ecosystems. She managed databases, led web teams, navigated vendor systems, and taught scholars how to access and evaluate information at scale. At its core, her work was about stewardship, access, and trust. That research-driven mindset eventually carried her beyond the university. She moved into agency-side research and product work, integrating user discovery and competitive intelligence into digital strategy. As AI tools accelerated, Jill recognized something familiar: the same questions libraries wrestled with for decades were now re-emerging around data quality, provenance, and governance. Today, she applies that foundation to responsible AI frameworks, helping organizations build guardrails before they scale. This episode lays the groundwork for a deeper dive into responsible AI in Part II. Key Takeaways Research is not academic overhead. It is infrastructure for better decision-making. Modern librarianship is rooted in systems thinking and information architecture. Not all information is equally accessible or equally trustworthy. Governance is a building discipline, not a compliance afterthought. Career pivots often reveal continuity rather than reinvention. The skills needed for responsible AI have been quietly developed for decades in adjacent fields.

In this episode of The Builders Podcast, Matt sits down with Dan Daly to unpack how a $600M automotive growth playbook became the foundation for an international real estate fund built around Portugal’s Golden Visa program. Dan shares how scaling an automotive startup from a single dealership to nearly $600M in annual revenue wasn’t about chasing more leads. It was about obsessing over customer experience. By personally calling customers and fixing small operational breakdowns, he unlocked profit without increasing marketing spend. That same principle now drives his hospitality and tourism real estate investments across Portugal. The conversation moves beyond real estate into first principles: optimize before you expand, focus on who you already serve, and build systems that increase margin without increasing chaos. Dan also walks through the mechanics of the Portugal Golden Visa, why Porto became his strategic focus, and how he built a $25M fund from a simple journal note that read, “Be the bank.” At its core, this episode is about leveraging experience across industries, trusting instinct, and learning how to do things you’ve never done before. Key Takeaways Revenue growth often starts with improving experience, not increasing leads. The same asset can become dramatically more profitable with better process. Real estate, especially hospitality, is fundamentally a customer experience business. Portugal offers structural advantages: supply constraints, strong tourism growth, and favorable financing. The Golden Visa creates long-term lifestyle optionality, not just financial return. Big ideas often begin as unclear journal entries — execution makes them real.

Lee Rossey is the CTO and co-founder of SimSpace, and he’s spent the last 25 years building in the deep end of cybersecurity, including 15 years at MIT Lincoln Laboratory. His worldview is refreshingly practical: if you can’t measure it, you don’t really understand it… and if you can’t test it under pressure, you don’t actually trust it. In this episode, we dig into what “proving grounds” means in the AI era. Red teams and penetration tests are valuable, but production systems have guardrails for a reason. You can’t take down a hospital, bank, or power company just to prove a point. SimSpace helps organizations create realistic, representative replicas of their environments so they can push tools and teams to failure safely, run repeatable attack scenarios, and build true muscle memory. AI is the accelerant on both sides. Defenders use it to cut through noise and respond faster. Attackers use it to craft more convincing lures, move through kill chains quicker, and exploit complexity. Lee’s core message lands clean: the future belongs to the organizations that don’t just buy AI security, but prove it… in reality… before betting the business on it. Key takeaways AI security needs proving grounds, because “trust” has to be earned through testing, not marketing. Production environments can’t be fully stress-tested, so realistic replicas are how you train and validate safely. Automation makes testing practical. If building the environment takes months, it won’t happen often enough to matter. The kill chain is compressing. AI reduces the time from recon to exploit, so defenders must shorten detection-to-response. Agentic tools introduce new attack surfaces like prompt injection and manipulation of decision-making. Humans aren’t disappearing, but their role shifts. The new norm is operators working side by side with AI.

Most builders don’t fail because they lack skill or effort. They struggle because the lessons that matter most only reveal themselves over long stretches of time. In this episode, Tyler Dane joins the show to reflect on the winding path of building. From early career pivots and high-stress on-call roles to indie product experiments and hard-earned clarity, the conversation traces what it actually takes to build something that lasts. Rather than focusing on tactics or tools, this episode digs into the deeper patterns builders encounter. The temptation to chase too many ideas. The illusion of momentum without real feedback. The quiet cost of systems that create constant stress. Tyler shares how stepping away from firefighting roles and embracing focused, reflective practices helped him see where his energy truly belonged. At its core, this is a conversation about finishing what matters. About recognizing that meaningful work often spans decades, not quarters. Through journaling, honest reflection, and learning to narrow focus, builders can reclaim both progress and creative identity. This episode is for anyone who’s realized that the real work isn’t just shipping faster, but building a life and body of work they’ll still be proud of years down the road. Key Takeaways Building careers are rarely linear, and that’s often a strength Focus matters more than raw output once you’ve learned the basics Early feedback prevents years of quiet misalignment Reflection helps solo builders avoid self-delusion Sustainable work beats constant urgency Finishing meaningful work is a long-game decision

In this episode of The Builders Podcast, Matt Levenhagen sits down with cybersecurity expert and security educator Robert Siciliano to unpack what it really means to build security in a world that defaults to trust. What begins as a conversation about cybersecurity quickly turns into a deeper exploration of human behavior, denial, and why most people only take security seriously after something goes wrong. Robert shares the personal experiences that shaped his career, from early encounters with physical danger to being hacked during the early days of online commerce. These moments forged a core belief that still guides his work today: security is personal first. Whether physical or digital, meaningful protection starts with awareness, responsibility, and habits built before a crisis. Together, Matt and Robert explore the concept of the human firewall. Not as a technical solution, but as a mindset shift. Rather than relying solely on tools, policies, or fear-based training, they focus on first principles and practical behaviors that turn individuals into active participants in their own security. The result is a grounded conversation about building security that actually sticks. Key Takeaways Most security failures are human problems, not technology problems Trust-by-default thinking creates blind spots attackers exploit People often ignore risk until they experience consequences Simple habits like password managers and 2FA go a long way Credit freezes are one of the most underused security tools Real security awareness is built through understanding, not fear

In this solo episode of The Builders Podcast, Matt Levenhagen reflects on what it really means to become a builder without shortcuts. Drawing from his early years as a self-taught artist in the pre-internet era, Matt explores how learning through books, libraries, and trial and error shaped more than just technical skill. It built patience, discipline, and the ability to stay in the work when progress wasn’t obvious. Matt then connects those early lessons to building his digital agency from the ground up. Without a day-one blueprint, he learned through experimentation, real clients, pricing mistakes, and constant iteration. Rather than discarding everything that didn’t work, he kept the “bricks” that held, slowly forming a foundation that could support growth, contraction, and rebuilding. The episode makes a thoughtful case against shortcuts in business, including buying outcomes without understanding how they were built. Matt argues that real resilience comes from lived experience, not borrowed tactics. For builders in the trenches, this conversation is a reminder that staying with the work is often what turns uncertainty into long-term strength. Key Takeaways: Shortcuts often outsource understanding instead of building it Blueprints can show outcomes, but they don’t create judgment Confusion and friction are part of how builders develop resilience Foundations are built by keeping what works and discarding what doesn’t Builders who do the work can adapt when things break or change Staying in the process turns you into someone who can carry what you build

In this episode of The Builders, Matt reconnects with Lorraine Ball, nearly 200 episodes after her first appearance, for a deep conversation on what it really means to build effective teams inside agencies. Rather than focusing on hiring hacks or org charts, Lorraine walks through the foundational thinking that separates high-performing teams from groups that simply execute tasks. Drawing from her journey from corporate leadership to running a successful agency, Lorraine explains why many agencies unknowingly train their teams to be order takers. She shares how shifting teams toward strategic thinking starts with two deceptively simple questions: who is the customer’s customer, and what does winning actually look like in the next 12 months. Without those answers, even great work becomes generic. The conversation digs into the real mechanics of building teams that think holistically across ads, content, design, and web. Lorraine outlines how intentional coaching, small learning loops, and better internal communication transform not just the quality of output, but the confidence and ownership teams bring to client relationships. Key Takeaways High-performing teams are built by teaching people how to think, not just what to produce Agencies lose value when teams act as order takers instead of strategic partners Knowing the customer’s customer changes every decision, from ads to UX Most clients can’t articulate success until you help them define it One-off training fails; consistent, focused coaching sticks Strong teams are created through clarity, communication, and shared context

In this episode of The Builders, Matt reconnects with Rob Broadhead, founder of RB Consulting, to explore how businesses can make better technology decisions in an era dominated by AI hype, tool overload, and constant pressure to “keep up.” Rather than chasing shiny solutions, Rob makes the case for slowing down and clearly defining the problems technology is meant to solve. The conversation digs into a common pattern founders face today. Tools pile up, automations get layered on, and suddenly the business feels more complex instead of more efficient. Rob explains why technology should serve the business roadmap, not dictate it, and why speeding up broken processes only multiplies dysfunction. AI, he notes, amplifies intent. If the problem isn’t well understood, the output won’t be either. Matt and Rob also explore AI’s most overlooked value. Not automation alone, but its role as a thinking partner. Used well, AI becomes a sounding board that helps leaders uncover blind spots, test assumptions, and discover better questions to ask. The takeaway is refreshingly grounded. Builders do not need to implement everything at once. They need to start small, stay intentional, and let clarity lead the build. Key Takeaways Technology should fit the business, not force the business to adapt to tools AI accelerates outcomes, good or bad, depending on how well problems are defined Overwhelm often comes from chasing solutions without clarity Start with one meaningful use case instead of trying to “AI everything” AI is most powerful as a thinking partner, not just an automation engine Strong systems evolve through intention, not pressure or fear of being left behind

Stephanie Sylvestre’s path to becoming CEO and co-founder of Avatar Buddy is anything but linear. Born and raised in Belize, Stephanie expected to return home after college and step into a defined future. When political change erased that path overnight, she was forced to adapt, relocate, and reimagine what building a life and career really meant. That adaptability led her into diplomacy as the youngest Honorary Consul of Belize in Miami, where she spent years navigating relationships, influence, and advocacy at a deeply human level. In parallel, an unexpected internship at Hewlett-Packard introduced her to technology through systems thinking, mentorship, and early software development. Rather than chasing hype, Stephanie learned how complex systems actually work, and where they fail the people relying on them. Those lessons carried forward into consulting, corporate IT, and eventually the founding of Avatar Buddy, a managed AI services company built around trust, safety, and human amplification. In this episode, Stephanie shares how a background rooted in diplomacy and quality-first thinking now shapes her approach to building AI systems that help humans do better at the work they already do. Key Takeaways Builder paths are rarely linear, and detours often create the strongest foundations Trust and relationships drive real outcomes more than process alone Early mentorship shapes how builders think about systems for life Quality matters because real people live with the results AI works best when it amplifies humans instead of replacing them Experience outside of tech often produces better technology leaders

In this solo end-of-year episode of The Builders Podcast, Matt Levenhagen pulls back the curtain on what he’s been building behind the scenes and why it matters far beyond AI hype. After briefly reflecting on a challenging couple of years in his agency, Matt dives into the real work: designing and building a deeply personal, enterprise-level system that unifies personal insight, business data, and AI into a single command center. This isn’t about tools or dashboards. It’s about creating structure that reduces friction, preserves context, and enables better decisions. The episode explores how understanding your past, protecting your data, and eliminating constant context switching can become a powerful competitive advantage. From layered personal and business hubs to a daily command center and outreach workflows, Matt shares how building systems for yourself can quietly change how you think, work, and rebuild for what comes next. Key Takeaways The real “killer app” isn’t software you sell, it’s the system you build for yourself Fragmentation, not effort, is what drains momentum in modern businesses Personal clarity and business clarity are deeply connected Security and ownership are essential for honest thinking and reflection A single command center can eliminate decision fatigue and context switching Building custom systems creates leverage that off-the-shelf tools can’t match

In this episode of The Builders Podcast, Matt welcomes back Damon Darnall to explore what happens when technology reaches a tipping point. While their first conversation focused on Damon’s background and the early days of drones, this discussion goes deeper into the drone revolution itself and how it dramatically lowered barriers to entry, unlocking hundreds of new business opportunities. Damon breaks down how drones evolved from complex, expert-only machines into accessible tools powered by sensors, automation, and onboard computing. That shift didn’t just make drones easier to fly. It changed who could participate, which business models became viable, and how real-world problems like inspections, safety, and data collection could be solved more efficiently. The conversation expands beyond drones into a broader lesson for builders. When technology removes friction, opportunity scales. Entire markets open up, new operators enter, and smart builders focus less on the novelty of the tool and more on creating repeatable, practical businesses around it. This episode offers a clear blueprint for recognizing those moments and building with intention when barriers fall. Key Takeaways The drone revolution lowered skill, cost, and complexity barriers, unlocking hundreds of new businesses “Easier to use” technology often leads to higher-value outcomes, not lower ones Automation and AI enhance human judgment instead of replacing it Safer, faster workflows create stronger and more scalable business models Successful builders design systems that reduce friction for newcomers The biggest opportunity is rarely the tool itself, but what it enables others to do

In this episode of The Builders, Matt sits down with Rob Broadhead, founder of RB Consulting, to explore the experiences that shaped his business-first approach to technology. What begins as a story about curiosity and problem-solving quickly becomes a reflection on early failures, missed assumptions, and hard lessons learned inside consulting firms and startups alike. Rob shares how watching software projects struggle, not because of bad code but because of unclear business problems, fundamentally changed how he thinks about building systems. From enterprise consulting to scrappy startups, each setback became a data point, teaching him that technology only works when it serves clearly understood processes and constraints. The conversation turns pivotal as Rob recounts the accidental founding of RB Consulting, including launching his company just one day before September 11, 2001. Navigating uncertainty, stalled projects, and shifting markets forced Rob to refine his thinking. Those early failures didn’t slow him down. They shaped the philosophy he still operates by today: business clarity first, technology second. Key Takeaways Early failures often reveal what theory and training cannot Most software problems begin as business problems Setbacks in startups provide a practical education in operations Incremental progress beats over-engineering A business-first mindset creates more durable systems

Dan Daly’s story is a blueprint for builders who didn’t start with a roadmap but found clarity through experience, self-awareness, and a willingness to study what works. In this episode, Matt sits down with Dan to trace how three core principles — personal brand, clear vision, and unwavering commitment — shaped each chapter of his growth. From his early days in a blue-collar “lifer” job to scaling nine automotive dealerships into hundreds of millions in revenue, Dan shows how intentional identity and consistent behavior created trust everywhere he went. The conversation dives into the pivotal moments that forced Dan to rethink who he wanted to be and how he wanted to build. He shares how he learned to differentiate himself in crowded markets by studying people, modeling successful patterns, and avoiding the habits that hinder growth. That instinct to refine and personalize his approach became the foundation of his personal brand — one that inspired teams, attracted customers, and opened doors across industries. As the episode unfolds, Dan shares how defining a vision others can trust — and then committing to it long enough for compounding effects to kick in — made all the difference. Whether launching a private equity hospitality fund or teaching sales teams to lead with intention rather than pressure, the throughline is unmistakable: brand, vision, and commitment aren’t abstract ideals. They’re operating systems for building something real, and they repeat themselves across every business he touches. Key Takeaways Brand begins with behavior. Who you are in the room shapes opportunities more than any product. Vision recruits people. When others can see where you’re going, they help you get there. Commitment compounds. Growth accelerates when you stop pivoting away from the work too early. Intention drives trust. Educating, not pressuring, is Dan’s core sales advantage. Principles scale across industries. Automotive, real estate, private equity — the pillars stay the same.