The Builders

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 TakeawaysMany scalable tools begin as manual systems that prove themselves firstTurning expertise into software requires translating human judgment into clear logicAI tools can accelerate research but still require careful verificationOutsourcing development requires strong communication and iterationBuilders 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 TakeawaysResearch 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 TakeawaysRevenue 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 takeawaysAI 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 TakeawaysBuilding careers are rarely linear, and that’s often a strengthFocus matters more than raw output once you’ve learned the basicsEarly feedback prevents years of quiet misalignmentReflection helps solo builders avoid self-delusionSustainable work beats constant urgencyFinishing 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 TakeawaysMost security failures are human problems, not technology problemsTrust-by-default thinking creates blind spots attackers exploitPeople often ignore risk until they experience consequencesSimple habits like password managers and 2FA go a long wayCredit freezes are one of the most underused security toolsReal 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 itBlueprints can show outcomes, but they don’t create judgmentConfusion and friction are part of how builders develop resilienceFoundations are built by keeping what works and discarding what doesn’tBuilders who do the work can adapt when things break or changeStaying in the process turns you into someone who can carry what you build