PLAY IN THE RIGHT SANDBOX: IPO Failure, Avoiding the Agency Trap & How to Build Assets Instead with Eric Berman

THE STORY YOU’RE AVOIDING: Stages, Storytelling & Why Founders Struggle to Explain Their Own Brilliance with Kyle Gray

What if the very expertise that built your business is the exact same thing making it harder to communicate it clearly? Many founders believe that if we just keep pushing - working harder, achieving more, scaling faster - eventually we’ll outrun the internal doubts, insecurities, and unresolved stories that follow us. But what if the opposite is true? In this episode of BUILDERS, I am so excited to sit down with Kyle Gray; founder, author, story strategist, and host of The Story Engine Podcast. Kyle works with high-performing founders, coaches, and experts who have already built meaningful businesses… but struggle to communicate their expertise in a way that truly lands. Not because they lack knowledge. But because they’re too close to it. When we get really good at something, we often make it harder to explain. We overcomplicate it. We wander. We try to prove our expertise instead of communicating it, and the stories that elaborate it, clearly. Here’s what we unpack in this episode: 00:00 – 08:46 | How Your Expertise is Ruining Your Influence We dive right into why presence matters just as much as polish when you're growing a business and showing up as a leader. Kyle explains why high-performing founders struggle to communicate. Turns out, your brilliance actually makes it harder to simplify your message! We talk about why trying to "outwork" a communication problem usually just results in stepping on your team's toes and getting C-minus results. 08:47 – 24:13 | From Chronic Illness to Superpower Kyle shares the deeply personal story of his battle with an autoimmune condition, and how a coach told him his illness was actually his superpower. It’s a literal goosebumps moment about how the parts of ourselves we think are "trash" are often exactly what sets us apart and allows us to connect with the people who need our help the most. 24:14 – 34:07 | The Life Cycle of Stories: Too Soon vs. Too Late We unpack why audiences crave presence over perfection. Plus, Kyle breaks down his "Life Cycle of Stories" framework. We talk about the danger of telling a story that's "too soon" versus "too late", and the fine line of emotional resonance and control required to make it land intentionally with your audience. 34:08 – 47:44 | The Big Lie We Believe About Success We completely nerd out on a scale metaphor for success. So many of us think we can just add more money and achievement to one side of the scale to avoid dealing with our shame or grief. Kyle explains why expanding our capacity for pain and vulnerability is what actually brings true abundance, and why you simply cannot out-succeed your problems. 47:45 – 54:35 | The Authority Story Framework Want to know exactly how to structure the first 3 to 5 minutes of your signature talk to make people tune in to listen? Kyle gives us a masterclass on his 3-act play. 54:36 – End | Storytelling as a Mirror & Martial Art We talk about the massive knock-on effects of finding your story. Kyle shares an incredible example of a that completely redesigned his life to come into alignment. And forget memorizing the perfect script. Kyle explains why great speaking is a flexible martial art, allowing you to adapt your story's framework to whoever is standing in front of you, whether they are clinicians, biohackers, or CrossFit gym owners. This episode is for the builder who: • Knows their expertise is strong - but struggles to communicate it clearly when it matters most. • Has built success through intelligence and effort - but senses the next level requires presence, clarity, and deeper self-awareness. • Is building something meaningful and wants to communicate that vision in a way that truly resonates. Because the ability to tell your story well isn’t just a speaking skill. It’s a leadership skill. Connect with Kyle: https://www.instagram.com/heykylegray/ [https://www.instagram.com/heykylegray/] https://www.youtube.com/@heykylegray [https://www.youtube.com/@heykylegray]

THE STRUCTURAL ADVANTAGE: Power-Aware Systems, Access Dynamics & Women-Led Scale with Eleanor Beaton

Builders, let’s talk about power. 🎧 Not the performative kind. Not the “manifest harder” kind. The structural kind. In this Season 3 episode of BUILDERS, I sit down with Eleanor Beaton - founder of Safi Media and host of the Woman Owned Podcast - to unpack one of the most quietly dangerous scaling traps in entrepreneurship: When women don’t have structure… they become the structure. This conversation is about infrastructure, operating systems, money, power, and why mindset is rarely the real bottleneck. We go deep on what actually allows a business to move beyond self-employment and into something scalable, sustainable, calm, and valuable. No hype or hearsay. Tried and tested truths from her own experience and helping hundreds of women-owned businesses scale. In this episode, we explore: 00:00 – 12:00 | Structure Creates Freedom Eleanor shares Safi Media’s mission to double the number of women-led companies scaling past $1M by 2030. We unpack her core belief: structure creates freedom. When infrastructure is missing, founders overfunction. And over time? They burn out. They resent the business. Or they pivot prematurely because boredom feels like misalignment. 12:00 – 18:00 | Coaching vs. Operating Systems We draw a clear line between coaching as a tool and over-coaching as a crutch. Eleanor breaks down why inquiry and raising standards matter- but why most advisory for women over-indexes on confidence and under-indexes on systems. We talk about the “barbie-fication” of entrepreneurship and how focusing on the person over the process quietly stalls scale. Mindset isn’t irrelevant. It’s just rarely the root constraint. 18:00 – 25:30 | Boring Businesses, Real Wealth Predictability beats excitement. Every time. We unpack what actually creates enterprise value and why topline growth without replicability isn’t an asset- it’s exhaustion with better branding. As Eleanor says, “You know what lights me up? A fuck ton of money in the bank.” Not for ego. For stability. For leverage. For protecting your team. 25:30 – 35:00 | The Visionary Myth & The Operator Reality Is it beneath a visionary to care about operations? We challenge the false binary of visionary vs. integrator - especially in bootstrapped companies. Most founders must build the first draft of their operating spine. Hiring someone to fix undefined chaos isn’t delegation. It’s avoidance. If you eat what you kill, you don’t get to skip this stage. 35:00 – 41:30 | Money, Power & Structural Access Eleanor shares a powerful story about starting her first business alongside a male peer. Same starting point. Different guidance. Different outcomes. She was directed toward self-improvement. He was introduced to capital, acquisitions, and operators. This is the structural reality behind why many women-led businesses plateau. It’s not a lack of ambition. It’s a difference in access, introductions, and infrastructure. 41:30 – 55:00 | Health, Wealth & Standards We close with a conversation about health, burnout, and scaling without sacrificing your nervous system. Eleanor shares how a fast-scaling company tripled revenue and burned out nearly the entire team in the process. Growth without standards is reckless. She shares what real boundaries look like inside Safi Media, the non-negotiables that keep her team focussed and functional. Scaling isn’t just about velocity. It’s about the standards you refuse to violate in pursuit of it. This episode is for the founder who is tired of being the all-in-one operating system. The one who knows they're capable of more - but knows they need to calm the chaos to scale. Because Wealthy Leadership isn’t endless hustle. * It’s infrastructure. * It’s power-aware design. * And it’s building a company that doesn’t demand your entire existence to survive. Connect wirh Eleanor: LinkedIn: https://www.linkedin.com/in/eleanorbeaton/ [https://www.linkedin.com/in/eleanorbeaton/] https://safimedia.co/ [https://safimedia.co/]

THE PERFORMANCE PARADOX: High Agency, Smarter Hiring & Elite Performance with Alex Auerbach

What do NFL quarterbacks, startup founders, and WNBA expansion teams have in common? Pressure. Decision making. And the ability to regulate themselves when it matters most. In this episode of Builders Season 3, I sit down with Alex Auerbach, performance psychologist to the Jacksonville Jaguars, advisor to the Toronto Tempo (WNBA expansion team), executive coach to founders and VCs, and builder of multiple ventures inside and outside of professional sport. This conversation is about elite performance. Not the Instagram version. The real version. We unpack high agency, hiring without bias, reframing stress, rest as a strategic weapon, and what it actually means to build a meaningful and maximized life. In this episode, we explore: ✅ 00:00 – 07:00 Introductions & Finding Your Edge The episode kicks off with the straight up facts on why job simulations beat a “good handshake,” before we dive into Alex’s background. We discuss his journey from clinical psychology to peak performance work in professional sport, and how he used experimentation and elimination of distractions to build his own ventures. ✅ 07:00 – 10:30 Athletes vs. Entrepreneurs: What’s Actually Different? Alex breaks down the real similarities between elite athletes and elite leaders - and where the comparison falls apart. ✅ 10:30 – 15:30 High Agency, Self-Regulation & Ownership We go deeper into internal locus of control- or what we call high agency. Alex explains why elite performers pair extreme ownership with self-regulation, and how the ability to control your thinking, physiology, and emotional response directly impacts team performance. ✅ 15:30 – 29:30 Stagnation vs. Plateaus & The Excitement vs. Stress Reframe This section is deeply tactical. We unpack threat vs. challenge framing, the “stress is enhancing” mindset, and four ways to reinterpret pressure so it becomes fuel instead of friction. ✅ 29:30 – 37:00 The Pursuit of Excellence & Predicting Success Alex discusses his personal drive to push human limits and how he transitioned from evaluating 300+ NFL/NBA draft prospects to bringing that same psychological rigour into the corporate world to solve the "fit" issue in executive hiring. ✅ 37:00 – 46:00 Designing Your Leadership Style From observing polarizing figures like Nick Saban to defining what it means to be a servant leader, we talk about the power of intentional leadership design. ✅ 46:00 – 57:00 Meaningful & Maximized: Redefining Success We pivot into how he defines success today - meaningful and maximal. We unpack core values, seasons of intensity, and why “having it all” is absolutely possible, but not in equal increments or equal velocity. ✅ 57:00 – 1:01:20 Building a Startup Inside Pro Sports Alex shares what it’s like advising the WNBA expansion team, the Toronto Tempo. We talk about velocity, visibility, real estate, and what founders can learn from organizations that must launch an MVP that is immediately ready to compete for a championship. ✅ 1:01:20 – 1:09:20 The Tactical Playbook: Hiring Without Bias This is a must-listen for anyone building a team. Alex breaks down exactly how to use structured interviews, job simulations, and hiring committees to dramatically increase your success rate. ✅ 1:09:20 – 1:21:20 Rest, Burnout & Sustained Elite Performance We close with something hustle culture still misunderstands: recovery. Stress without recovery leads to breakdown. Stress with recovery leads to growth. This episode is for the builder who wants to reliably and sustainably perform at an elite level. Because growth in business and leadership isn’t just about revenue. * It’s about agency. * It’s about regulation. * It’s about hiring well. * It’s about recovering strategically. And it’s about building a life that feels meaningful - not just impressive. Connect with Alex: https://www.linkedin.com/in/alexauerbachphd

AS WITHIN, SO WITHOUT: The Convergence of Cause & Commerce with Christian LeFer

Builders, this one goes deep. 🎧 In this episode, I sit down with Christian LeFer, CEO of Instant Nonprofit, for a wide-ranging conversation about justice, bureaucracy, leadership awakening, and what it actually means to build impact at the convergence of cause and commerce. Christian has helped start thousands of nonprofits, redesigned a broken approval process, and built a company rooted in emotional intelligence, culture, and conviction. This conversation isn’t about charity optics. It’s about alignment. Power. Process. And learning when to push - and when to pause. In this episode, we explore: 00:00 – 09:00 | Justice, Special Olympics & Becoming a Builder Christian shares how growing up with a developmentally disabled sister shaped his deep sense of justice and service. 09:00 – 16:00 | Bureaucracy, 501c3s & The “Love Letter to a Bureaucrat” Why is starting a nonprofit often harder than starting a business? Christian breaks down the friction inside the 501c3 process and how he engineered dramatically faster IRS approvals by designing applications that made agents’ lives easier. 16:00 – 24:00 | High EQ as Competitive Advantage We explore why emotional intelligence is not a “soft skill” but a strategic lever. From turning refunds into raving fans to listening without defensiveness and validating customers instead of hiding behind policy, Christian shares how empathy builds trust — and how trust compounds into long-term advantage. 24:00 – 31:00 | Breakdown, Shadow Work & The Inner Rebuild This is the chapter most founders don’t talk about. Business strain. Relationship strain. Identity strain. Christian opens up about the personal collapse that forced him to confront unresolved trauma, self-talk, and misalignment. Out of that awakening came a powerful leadership principle: as within, so without. 31:00 –37:00 | Culture as a Safe Container Why does safety fuel creativity? We unpack how vulnerability - done intentionally -strengthens teams, and how building a culture of acceptance creates the psychological safety required for innovation. 37:00 – 44:00 | Wealthy Leadership: Throttle Up vs. Throttle Back Christian reflects on the shift from grinding harder to allowing space. We explore persistence versus patience, structure as a path to freedom, and optionality as a true form of wealth. 44:00 – 51:00 | Conviction, Discourse & Leading in a Fractured World The conversation widens to culture and society. Christian shares his views on free speech, capitalism, and institutional trust — and why leaders can’t afford to retreat from difficult conversations. Wealthy Leadership isn’t just about revenue; it’s about participating in shaping the world you want to live in. 51:00 – 1:02:00 | How Nonprofits Fit into Smart Business Strategy We break down what a 501c3 actually is and how nonprofits can strategically complement for-profit companies. 1:02:00 – End | Process Over Tools & Building Anti-Fragile Systems We close with a discussion on why process is king. Christian shares how clear articulation of strategy drives alignment, and why systems that grow stronger under stress -inspired by Antifragile - are essential for long-term resilience. This episode is for Builders who: * Want to integrate impact into their business model * Care about culture as much as cash flow * Feel the tension between force and flow * Believe leadership is both internal and external This is a thoughtful, grounded conversation between two operators who believe business can be both profitable and principled. 🔗 Connect with Christian LeFer: Facebook:https://www.facebook.com/InstantNonprofit Instagram: https://www.instagram.com/instantnonprofit [https://www.instagram.com/instantnonprofit] LinkedIn: https://www.linkedin.com/company/instantnonprofit [https://www.linkedin.com/company/instantnonprofit] https://www.youtube.com/@InstantNonprofitUSA [https://www.youtube.com/@InstantNonprofitUSA]

PLAY IN THE RIGHT SANDBOX: IPO Failure, Avoiding the Agency Trap & How to Build Assets Instead with Eric Berman

Builders, this one goes deep. 🎧 In this episode, I sit down with Eric Berman - Founder/CEO of Speakeasy Mastermind- for a wide-ranging conversation about ownership, follow-through, community, and what it actually means to build success that lasts. Eric has been building companies since the early days of the internet. He’s helped scale platforms, worked alongside names like Brian Tracy and Jack Canfield, lived through near-IPO highs and market-crash lows, and spent decades inside the agency world. This conversation isn’t about hype. It’s about what you learn when you’ve been in the arena long enough to see the patterns. We talk about the invisible cost of agency life, why most entrepreneurs underestimate follow-through, and how community becomes a strategic advantage, not a “nice to have”- as the game gets more complex. In this episode, we explore: 00:00 – 13:00 | Becoming a Builder & The Crash Eric’s early path into entrepreneurship, why building from nothing lit him up, and the reality of the "IPO that never happened"- being weeks away from a massive exit and watching it disappear. 13:00 – 24:20 | Resilience & The Pivot How to navigate the aftermath of a market crash. We unpack resilience, identity, and why skills can’t be taken away, even when money can. Plus, how Eric pivoted to working with legends like Brian Tracy. 24:20 – 36:00 | “I Am Responsible” The mindset that changed how Eric leads, navigates setbacks, and builds trust with clients and teams. Radical ownership as a leadership unlock. 36:00 – 48:00 | The Agency Trap The realities of service businesses, capped upside, and the moment Eric realized he’d been climbing the “wrong ladder”. Why the agency model often traps founders in a cycle of revenue without asset value. 48:00 – 52:30 | Follow-Through as a Superpower Why high follow-through is rarer than vision - and why it quietly separates builders who scale from those who stall. 52:30 – 59:30 | Asset Equity & Redefining Success Why Eric is shifting from clients to partners, plus a candid look at fatherhood, presence, and how his definition of success has evolved. 59:30 – End | Speakeasy & The Power of Community How Speakeasy Mastermind was born, why entrepreneurship is lonelier than we admit, and why in-person community matters more than ever in an AI world. This episode is for Builders who: • Are successful - but questioning the game they’re playing • Feel the tension between growth and alignment • Want leverage, ownership, and freedom- not just revenue • Know community matters, but haven’t found the right room yet This is a grounded, honest conversation between two operators who’ve seen enough cycles to know what actually matters. 🔗 Connect with Eric Berman: https://www.linkedin.com/in/ericberman/ [https://www.linkedin.com/in/ericberman/], https://www.instagram.com/ericbberman [https://www.instagram.com/ericbberman]