The Builders

Matt Levenhagen

"The Builders" Podcast is designed for those that are 'building' stuff on the web. Whether that's building a business, an agency, building teams, building products, services.. or building websites.. if it's related to building something, it's fair game.

  1. 21 HRS AGO

    Matt Levenhagen – A Builder’s Journey: What My 90s Journals Taught Me About Becoming and the Path

    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.

    53 min

  2. MAR 2

    Jill Heinze – How a Research-Driven Librarian Became an AI Governance Architect

    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.

    47 min

  3. FEB 23

    Dan Daly – Applying a $600M Customer Experience Playbook to Real Estate & the Golden Visa

    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.

    38 min

  4. FEB 16

    Lee Rossey – Building Proving Grounds for AI Security: Trust, Testing, and Reality

    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.

    38 min

  5. FEB 9

    Tyler Dane – The Long Arc of Building: Focus, Feedback, and Finishing What Matters

    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 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

    51 min

  6. FEB 2

    Robert Siciliano – Building a Human Firewall in a World That Trusts Too Easily

    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 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

    47 min

  7. JAN 26

    Matt Levenhagen – Building Without Shortcuts: Why Doing the Work Creates Resilient Builders

    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

    38 min

  8. JAN 19

    Lorraine Ball – Building Strategic Agency Teams Without Order Takers

    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 produceAgencies lose value when teams act as order takers instead of strategic partnersKnowing the customer’s customer changes every decision, from ads to UXMost clients can’t articulate success until you help them define itOne-off training fails; consistent, focused coaching sticksStrong teams are created through clarity, communication, and shared context

    51 min
See All (268)

Trailer

5
out of 5
2 Ratings

About

"The Builders" Podcast is designed for those that are 'building' stuff on the web. Whether that's building a business, an agency, building teams, building products, services.. or building websites.. if it's related to building something, it's fair game.

Information

  • Creator
    Matt Levenhagen
  • Years Active
    2020 - 2026
  • Episodes
    268
  • Rating
    Clean
  • Copyright
    © Matt Levenhagen
  • Show Website
    The Builders