Author name: Kyle Gray

What if the biggest obstacle in your business isn’t the problem you’re trying to solve—but the question you haven’t been willing to ask? In this episode of The Story Engine Podcast, I sit down with executive coach and Vistage chair Ken Proctor to explore the power of asking better, tougher questions. Ken shares how his own failures taught him that leaders don’t necessarily need more answers—they need someone willing to challenge them, uncover their blind spots, and help them see what’s really driving their decisions.

We dive into the “ghosts” that can quietly shape the way leaders operate, from fear and insecurity to old stories carried from childhood into business. Ken explains why asking uncomfortable questions can create more respect than simply trying to be liked, while I explore my own experience of discovering how a single comment from my father influenced years of decisions in my career. This conversation is ultimately about using honest questions to break out of familiar patterns, create greater self-awareness, and move toward more alignment and integrity as a leader.

I’ve built a lot of businesses over the years, but some of my biggest lessons came from the ones that went painfully wrong. In this episode of The Story Engine Podcast, I sit down with serial entrepreneur Tom Matzen, who has built 94 businesses, taken companies public, built franchise models, and experienced both enormous wins and multimillion-dollar losses. We dig into one of the most painful chapters of his career: turning a company valued at $21.4 million into $10 million in debt in just six months after stepping away from the business and trusting the wrong person. Tom shares what that experience taught him about intuition, accountability, checks and balances, and the dangerous difference between delegation and simply abdicating responsibility.

But the conversation goes far beyond what went wrong. Tom explains why entrepreneurs can accidentally build businesses that are completely dependent on them—and why becoming “indispensable” can actually become a liability. He introduces his Omega Method, built around organic growth, machine leverage, equity expansion, growth alliances, and asset accumulation, with the goal of creating more profit and more freedom while allowing the founder to spend more time in their zone of genius. We also get into AI and automation, strategic partnerships, acquiring rather than building from scratch, and the powerful story of how losing another business ultimately led Tom to create Icon Maker. This is a conversation about turning painful business failures into frameworks, freedom, and a completely different way of building.

I’ve spent a lot of time thinking about the patterns that quietly shape how we lead, love, and live—and this conversation with Bryan Post took that exploration somewhere much deeper. Bryan has spent nearly 30 years working with families, adopted and foster children, parents, CEOs, entrepreneurs, and high-performing executives. His central message is powerful: when we experience stress, we don’t simply become stressed—we can actually regress emotionally, allowing old fears, traumas, and survival patterns to take control. In this episode, we unpack his “Fear to Love” methodology and explore why the same emotional patterns he sees in children can show up in highly successful adults who have mastered business, achievement, and grit but still struggle with relationships, connection, and a deeper sense of meaning.

What really stood out to me was Bryan’s emphasis on going beyond simply thinking about our trauma or inner child. Real transformation, he argues, requires us to slow down, enter the emotional experience, breathe through it, and learn to meet our pain without shame or judgment. Bryan shares his own deeply personal story—from being conceived under traumatic circumstances and moving through foster care and adoption, to a pivotal night when he collapsed on the floor after a painful marriage experience, and eventually to a powerful moment in Sacramento where he openly processed his own emotional overwhelm in front of a group. We also talk about why successful people can climb the first mountain of financial and professional achievement only to discover an emotional void when it’s time to climb the second mountain of meaning. If you’ve ever wondered why you can be incredibly capable in one area of your life while feeling completely overwhelmed in another, this conversation offers a fascinating look at what may be happening underneath the surface.

What happens when the traits you spent your life fighting become the very things that allow you to serve others? In this episode of The Story Engine Podcast, I sit down with Jennifer Hill, a self-described former “asshole” who has transformed decades of misunderstanding, broken relationships, self-hatred, and personal development into what she now calls her superpower: human connection. Jen shares the brutally honest moment when someone finally told her that her behavior was hurting people—and how that confrontation started a decades-long journey of learning to understand herself, embrace her autistic brain, and turn the way she naturally sees and connects people into a gift.

Then the story takes an unexpected and heartbreaking turn. Just as Jen and her business partner Julian were preparing to sell their technology company, Julian suddenly passed away, the acquisition fell apart, and Jen found herself on her knees in Lisbon asking God and the universe what she was supposed to do next. Her answer became the Jennifer Hill Tribe—a community designed around belonging, safety, generosity, and meaningful human connection. We talk about how the tribe grew from a simple request for 10 members into a thriving community, why so many successful entrepreneurs still feel like they can’t fully be themselves in other rooms, and how Jen uses her unique ability to connect people to create relationships that become friendships, business partnerships, and sometimes even romance. Most importantly, we explore why the story that nearly breaks you may eventually become the exact story that helps someone else survive their hardest day.

In this episode of The Story Engine Podcast, I sit down with Dr. Torrie Thompson to unpack one of the most frustrating experiences in health: doing everything “right” and still feeling terrible. We talk about the hidden toxins in our homes, products, and environments that can quietly accumulate over time—and why so many symptoms that we’ve been taught to accept as “normal” may actually be signs that something deeper is going on. From scented trash bags and household chemicals to mold, heavy metals, environmental toxins, and gut issues, Torrie explains why her approach starts with extensive data and testing rather than guessing. She shares how she uses comprehensive labs to identify what is actually happening inside someone’s body, then combines that information with personalized, data-backed protocols and a team-based approach to help people clear what’s holding them back.

But the most powerful part of our conversation is Torrie’s own story. She became sick at just 12 years old and spent 15 years going from doctor to doctor while being told that her labs were “perfect,” despite debilitating headaches, weakness, insomnia, depression, weight gain, brain fog, and severe bone pain. It wasn’t until she began digging through years of old lab work herself that she discovered clues pointing toward Lyme disease, co-infections, mold, and environmental toxins—things that had been missed for years. We also take a deeper look at the transformation that happened when she finally began getting answers: having the energy to work out again, play tennis, get through the day without needing a nap, and ultimately feel like she had her body and her life back. Along the way, I help Torrie tell this story in a way that reveals not only the data behind her work, but the deeply personal reason she became so passionate about helping others find answers.

What happens when the challenges you’ve spent years trying to overcome become the very experiences that shape who you’re capable of becoming? In this episode of The Story Engine Podcast, I sit down with Tom LeNoble, a former executive at companies including MCI, Palm, Walmart.com, and Facebook, who has been given six months to live three separate times and has lived with metastatic cancer for the past fourteen years. Rather than allowing those diagnoses to define his life, Tom has built his philosophy around three powerful principles: risk, resilience, and reinvention.

We dig into what it actually looks like to stop living in the past, stop waiting for a “do-over,” and start using your past as evidence of what you’re capable of. Tom shares how his childhood, health crises, and willingness to take enormous risks—including leaving a dream corporate position to join a then-little-known Facebook—shaped the way he now advises executives and professionals. We also explore the hidden problems beneath the problems people bring to coaching, the six forms of energy that can become imbalanced, why curiosity and psychological safety can accelerate change, and how “acting as if” can help you move toward a life that doesn’t yet exist. This is a conversation about resilience, but more importantly, it’s about what becomes possible when you decide that your past can inform your future without controlling it.

In this episode of The Story Engine Podcast, I sit down with Barry Goldstein, a longtime music producer and creative collaborator who has spent more than 40 years exploring how music can magnify mission, unlock creativity, and help us move through the blocks that keep us from our next level. We dive into the idea of the “last 3%”—that frustrating gap between knowing you have something great and actually being able to fully express its potential. Barry explains why solving that final piece doesn’t necessarily require more effort, more analysis, or more information. Sometimes, it requires getting out of the thinking mind and into a deeper state of intuition, coherence, creativity, and flow.

Barry also shares the deeply personal story that led him to rethink his entire relationship with music. At the height of his career as a major-label record producer in New York City, the work he had once loved became repetitive, stressful, and creatively draining. His search for a way back to the joy he experienced as a 14-year-old musician eventually led him to experiment with music created at 60 beats per minute—music he describes as “decomposing” rather than composing. What began as an experiment for his own healing unexpectedly became a tool that people used for sleep, anxiety, childbirth, dementia, and other transformational experiences. We also explore the moment Barry realized just how powerful that work had become while watching thousands of people experience breakthroughs during a walking meditation at a Dr. Joe Dispenza event in Cancun. This conversation is ultimately about more than music—it’s about remembering why we create, learning to trust what we don’t yet know, and discovering what becomes possible when we bring the heart and mind back into alignment.

I’ve spent a lot of time thinking about alignment—not just as a personal-growth concept, but as something that directly affects how we lead, build businesses, make decisions, and live our lives. In this episode of The Story Engine Podcast, I sit down with Esther Wildenberg, an executive coach, entrepreneur, consultant, and AI business owner who has spent more than 20 years helping leaders recognize when they’ve drifted out of alignment and find their way back. Esther describes alignment as the place where our purpose, passion, heart, identity, and actions are working together—and when they are, we create a kind of inbound energy that attracts the right people, opportunities, and growth.

We get very practical about what happens when that alignment disappears. Esther calls it “founder’s fatigue”: when we become obsessed with everything that isn’t working, blame our employees, clients, finances, or circumstances, and convince ourselves we simply don’t have enough time. She explains why stepping away from the business can actually be one of the most productive things an entrepreneur can do, including her unconventional three-day process of removing clients from their normal environment—and even taking away their phones—to create enough space for clarity. We also dive into Esther’s own experience during the COVID pandemic, when a company pivot, a newborn son in the NICU, isolation, and an identity crisis forced her to completely rethink how she was living and leading. Ultimately, this conversation is about learning to step out of the trenches, reconnect with yourself, and create the kind of business and life that actually supports the person you want to become.

What if the very experiences you’ve been trying to leave behind are actually the things that qualify you to play a bigger game? In this episode of The Story Engine Podcast, I sit down with Markus Kaulius, a multi-exit entrepreneur, investor, author, and longtime student of personal development, to unpack the beliefs, habits, health, and faith that have shaped the man he is today. Markus grew up poor, in a broken family, and describes himself as starting “behind zero”—but instead of seeing that history as baggage, he learned to recognize it as the source of his work ethic, resilience, and ability to connect with people. We dig into why we so often write successful people off by assuming they were simply born that way, and how doing that protects us from having to challenge our own beliefs, identity, and assumptions.

Then we go much deeper. Markus shares the system he uses to create the life he wants: identifying the habits that support that life, putting those systems in place, and trusting them long enough to work. We explore why health should come first if you want to give your best to your family and your work, why faith is about more than religion and can include having genuine faith in your own purpose, and what happened when Markus hit one of the lowest points of his entrepreneurial life during COVID. After his business dropped 70% in a single month, he found himself leading from fear and holding an all-hands meeting that made him realize he had become the leader he never wanted to be. What happened next completely changed the trajectory of his company. This conversation is ultimately about learning to see obstacles differently, moving from scarcity to abundance, and realizing that you may be much closer to playing the bigger game you were designed for than you think.

What happens when you’ve built the successful career, hit the milestones, created the life everyone tells you that you should want—and yet, deep down, you know something is wrong? In this episode of The Story Engine Podcast, I sit down with Melissa Marina, a subconscious healer and intuitive channel for top entrepreneurs and founders, to explore what happens when high achievers finally stop compromising their deepest desires. Melissa shares the story of graduating with honors, winning entrepreneurship awards, landing a great corporate job, and seemingly doing everything “right”—while privately feeling miserable, coping with wine and cigarettes, and wondering why success wasn’t making her happy.

We dive into the patterns that keep ambitious people stuck, including people-pleasing, limiting beliefs, unsupportive relationships, old identities, and the pressure to pursue goals that no longer feel meaningful. Melissa walks me through her Release, Reveal, Rise framework for clearing the patterns holding you back, reconnecting with your deeper purpose, and building a new identity and lifestyle around what you actually want. We also explore one of the most powerful themes of the conversation: sometimes what looks like a business or money problem is actually connected to your relationships, your identity, or the life you’ve been afraid to ask for. This episode is ultimately about something much bigger than making more money—it’s about creating a life where success, fulfillment, family, freedom, and purpose can actually coexist.