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I Have Some Questions...
Most people know the headline of a leader’s story. Few know the path it took to get there. This podcast goes beyond titles, book launches and business wins, to explore the lived journey behind the thought leader.
Through deep, unhurried conversations, we uncover the moments that shaped them—the doubts, pivots, convictions, and quiet breakthroughs that built their body of work.
Each episode features authors, coaches, executives, and bold thinkers who have forged their own path. Instead of rehearsed talking points, they’re invited into a space where thoughtful questions unlock something more human. The result is a layered conversation that reveals not just what they preach, but how they became the kind of person who can teach it.
Because we believe the best stories aren’t always told—they’re revealed. And when brilliant people are given the right questions and the room to answer them fully, what emerges is insight you can feel, frameworks you can apply, and a deeper understanding of what it truly takes to lead, create, and contribute at a meaningful level.
Episodes
225 episodes
227: Vincent Van den Broeck: "The 1% Survival Mindset That Rebuilt Everything"
Vincent Van den Broeck, founder of the UID Club and author of Everything Feels Impossible Until It’s Done, shares how hospitality sparked his creative drive, and how a life-threatening accident became a mirror for building resilience, non-negot...
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226: "From Job Loss Headlines To Real Adoption, What Changes When Teams Use AI Well?" ft. Justin Coats
Erik and Justin reset the conversation from AI tactics back to the “grand dream,” sharing optimistic, near-term business use cases, especially in healthcare and logistics/robotics.🧭 Conversation HighlightsErik and Just...
225: "Is AI Literacy Missing From Classrooms While Work Is Being Redefined?" ft. Asher Albertini
Asher Albertini, an 18-year-old high school senior and former LearnAir intern, shares what AI has changed for him in school, friendships, and career thinking, and how his generation should prepare for a future where entry-level work gets redefi...
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224: "The Hidden Cost Of Staying Comfortable" ft. Carl Loeb
With Erik out, Justin Coats steps into the host chair for a conversation with veteran creative Carl Loeb about what happens when generative AI enters the creative process—and why the answer isn’t to resist it or surrender to it.Carl draw...
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223: "Are Your Numbers Telling The Real Story or Just a Misleading One?" (Reflections On Scott Lauray)
🧠 Erik’s TakeErik treated the episode like a “numbers as a compass” field guide. What stayed with him wasn’t finance trivia, it was the discipline of turning ratios and variances into sharper questions. He also realized he keeps c...
222: "The Value of Communicating From Day One" (Reflections On Joshua Altman)
🧠 Erik’s TakeErik frames this as more than a communications discussion. The real question, for him, is timing: how fast a company can learn what it is, how it should describe itself, and whether the rest of the business is ready t...
221: Scott Lauray: "The Quiet Metrics That Increase Saleability"
Scott Lauray shares how ProVia Partners helps middle-market owners make confident financial decisions, from business valuation to M&A advisory and fractional CFO work. He connects enterprise value with real owner goals, and frames business ...
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220: Joshua Altman: "How Much Is Disorganized Comms Really Costing You Per Month?"
Erik talks with Joshua Altman about why communication gets “random acts” treatment, and how fractional chief communications officers bring strategy and consistency without full-time cost. Joshua shares two core frameworks, Story-Narrative-Brand...
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219: "Why You Cannot Shortcut The Human Part Of AI Implementation" ft. Justin Coats
Justin Coats breaks down the idea of “super apps” for AI and what that really means for corporate adoption, change management, security, and tokenomics.🧭 Conversation HighlightsJustin defines super apps as AI workspace...
218: "Is Promising Outcomes the Worst Thing We Could be Doing?" (Reflections On Jaclyn Orent)
🧠 Erik’s TakeErik treated this as a compact leadership debrief, not just a recap. The uncomfortable through-line for him was the idea that forward movement can come from releasing control, even when his natural instinct is to defi...
217: "How Do You Create AI Coaching That Adapts Over Time?" (Reflections On Gavin Lorenzo)
🧠 Erik’s TakeErik treats this “short review” as a real question, not a tech demo. The core shift for him is moving from AI personalization as memory, to AI personalization as understanding: a predictive model of how a specific per...
216: Jaclyn Orent: "Your Founder Problem Isn't Lack of Clarity, It's Avoiding Letting Go"
Jaclyn Orent joins Erik to unpack her path from legacy sales success to a mission focused on culture change. She explains “selling from force vs. from listening,” the science language behind her work on surrender and consciousness states, and h...
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215: Gavin Lorenzo: "Can AI Actually Understand Humans Without Human-Grade Self-Awareness?"
Gavin Lorenzo explains why AI struggles to truly understand people, not just store facts. He shares how Tellbloom builds a “third-party”-like model of a user by learning from passive interactions, then uses that context to improve responses. Th...
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214: "Accuracy Through Repetition: When Should You Let AI Work More Independently?" ft. Justin Coats
Erik and Justin tackle viewer-submitted AI questions in a practical Q&A focused on trust, compliance, meeting recording boundaries, and how to scale an AI pilot without losing control.🧭 Conversation HighlightsTrust...
213: "The Hidden Gap Between Human Behavior and Organizational Design" (Reflections On John Marshall)
🧠 Erik’s TakeErik treats this short review as more than “culture talk.” The conversation with John Marshall keeps circling back to a hard truth: our systems can evolve, but humans bring the same familiar dynamics into every room. ...
212: "Supply Chain People Are Accountable For Everything, But Responsible For Nothing" (Reflections On John Kill)
🧠 Erik’s TakeErik treated the episode like a field report from inside the parts of business most people never notice. After listening to John C. Kill, he came away less focused on “supply chain” as a function and more focused on s...
211: John Marshall: "Psychological Safety Is Not the Counterpart of Conflict"
John Marshall argues the hardest challenge of becoming an interplanetary species is not rockets, it’s psychology. He explains how “humescence” helps individuals and organizations redesign inner, interpersonal, and communication systems so missi...
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210: John Kill: "The Real Truths Surrounding the Supply Chain Industry"
John C. Kill explains why supply chain stays invisible until it breaks, using the “duck paddling under water” metaphor. He shares what friction really looks like: last-mile trucking pressures, supplier consolidation, weather and geopolitical ri...
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209: "Are Your AI Tools Updating Faster Than Your Team Can Handle?" ft. Justin Coats
Erik and Justin dig into how fast-moving AI platforms are changing (sometimes without warning) and what business leaders can do to avoid broken workflows, plus a few concrete examples like GPT Live voice, ChatGPT Work, and Atlas being retired.<...
208: "Navigating Through Uncomfortable Ceiling Talks" ft. Alli Murphy
Erik and Alli unpack what it feels like when a leader realizes a person might be at their ceiling. They compare different coaching approaches, including changing assumptions about the role, using outside perspective, and running short “experime...
207: Gregory Kovsky: "The Hidden Barriers To Becoming a Real Business Broker"
Selling a business is often the largest financial transaction of an entrepreneur’s life—but according to Gregory Kovsky, most business owners underestimate how complex the process really is.In this conversation, Erik sits down with Grego...
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206: Olivia Bryant: "Culture Breaks When Values Become Words"
What happens when an HR executive, hospitality operator, and culture strategist all show up in the same person?In this conversation, Erik sits down with Olivia Bryant to explore one of the most misunderstood topics in business: culture. ...
205: AI Will Disrupt Tasks, Not Entire Jobs
Erik argues that AI will displace some tasks and some people, but the bigger story is job redefinition and hiring growth driven by unlocked market value. He lays out five examples, contrasting “tasks” AI can replace with “jobs” that exist becau...
204: "How To Coach Through The Delegation Mess" ft. Alli Murphy
Delegation doesn’t go wrong because you delegated. It goes wrong because something underneath was already broken, and now you can see it. The real work for a senior leader is to respond in a way that protects trust while helping your people sol...
203: Eric Wiklendt: "What No One Talks About in M&As About Adding Value"
In this conversation, Erik sits down with Eric Wiklendt, Managing Director at Speycide Equity, to pull back the curtain on private equity, acquisitions, and the future of manufacturing. Eric explains how investors think about value creation, wh...
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