I Have Some Questions...

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 how identity-based marketing helps cultural catalysts opt in, align, and execute systemic change from the top down.

👤 About the Guest

Jaclyn Orent is CEO and co-founder of the Cultural Catalyst Network. After nearly 20 years in sales and sales leadership, she shifted toward emotional intelligence, mindfulness, and consciousness research to help leaders create culture change inside organizations. Her work connects inner transformation with measurable organizational outcomes, designed for founders, CEOs, and leaders who want to be

🧭 Conversation Highlights

• How her “identity as a salesperson” shifted into realizing alignment, not performance, is the real lever for results.
• A research-informed framework for surrender: feel feelings, release judgment, accept reality as it is, and use it to change leadership state.
• Why forcing goals can burn people out and why moonshot clarity requires committing from the heart, not only the spreadsheet.
• How the network uses the shared identity “cultural catalyst” to create opt-in alignment and peer groups that bridge silos for culture change at scale.

💡 Key Takeaways

• Leadership state matters: what leaders carry in fear, anger, or apathy shapes outcomes, communication, and team behavior.
• Surrender is practical: feeling feelings, releasing judgment, and accepting reality enables clearer execution and pivoting.
• Systemic change is top-down: developing founders and CEOs creates nonlinear impact across the whole organization.
• Identity beats persuasion in sales: when people self-identify as cultural catalysts, motivation becomes intrinsic and action becomes easier to coordinate.

❓ Questions That Mattered

• What does it mean to “sell from force” versus “sell from listening,” and how does that change results?
• What are the three steps of surrender, and what is the hardest part for leaders to practice?
• How can founders sit in uncertainty without preemptively locking into the wrong quantified goal?
• How does an identity-based label like “cultural catalyst” create real execution inside organizations, not just inspiring language?

🗣️ Notable Quotes

• “Just because I have the skill set to develop people that really sell from a place of alignment doesn’t mean I need to be [in sales].”
• “People keep telling you to let go. I don’t know how to let go.”
• “Fear is force, and acceptance is power.”
• “Instead of selling an outcome, I actually need to connect to a dream of the ideal client.”

🔗 Links & Resources

• Follow Jaclyn Orent on LinkedIn
• Check out the Cultural Catalyst Network
• Power vs. Force: The Hidden Determinants of Human Behavior — Dr. David R. Hawkins.
• Letting Go: The Pathway of Surrender — Dr. David R. Hawkins. 
• 10x Is Easier Than 2x — Dr. Benjamin Hardy & Dan Sullivan. 
• The 5 Levels of Leadership — John C. Maxwell
• Gene Keys: Unlocking the Higher Purpose Hidden in Your DNA — Richard Rudd.

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. The conversation also covers testing, privacy, and the governance challenges raised by frontier models like Fable.

👤 About the Guest

Gavin Lorenzo is the founder of Tellbloom, working from Georgia with support from the Alabama Entrepreneurship Institute. A second-time founder, he built his way from an AI tutor for LSAT prep to a mission focused on helping AI understand humans. His current work includes a Chrome extension that analyzes how you interact with Claude or ChatGPT to personalize prompts more effectively.

🧭 Conversation Highlights

• Tellbloom’s goal: maximize AI’s understanding of humanity, moving beyond “memory” into predictive behavior and intuition-like grasp.
• Gavin’s origin story: building an LSAT tutor revealed AI’s limits in personalization and context formation.
• How Tellbloom tests progress: A/B testing many “pipelines,” persona-based fine-tuning, and benchmarking before wide deployment.
• Governance and safety: why model access, export controls, and safeguards matter, and why governance cannot be left solely to model companies.

💡 Key Takeaways

• Personalization fails when it depends too heavily on a user’s ability to articulate themselves; passive observation is a better data source.
• “Understanding” is hard to define, but Gavin frames it as the ability to accurately predict and adapt in a way that feels human.
• To make squishy human modeling testable, you need repeatable suites, personas, and benchmarks.
• As models get more powerful, regulation and privacy become central product and societal design problems, not afterthoughts.

❓ Questions That Mattered

• What does it mean for AI to “understand” a person, beyond recalling facts or recursing into retrieved memory?
• Where is the line between building a cool tool for yourself and solving a real, horizontal customer problem?
• How do you make psychology-like ideas falsifiable by testing them through an AI “template of intelligence”?
• If frontier models can be used for harm or circumvent safeguards, what governance framework should govern capability, access, and rollout?

🗣️ Notable Quotes

• “It’s really not possible to build those [models] programmatically without randomness and variance.”
• “You cannot alter what the circus is doing unless you are inside the circus.”
• “AI is going to have to understand [people] and intuit that understanding, or else it becomes a generalizing agent.”

🔗 Links & Resources

• Follow Gavin Lorenzo's LinkedIn
• Contact Gavin at [email protected]

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 Highlights

• Trust AI at work by treating it like human trust: start slow, use tasks you can verify, and measure over repetition.
• For compliance constrained data, begin with low-risk admin work, then use governance, vendor requirements, and existing industry frameworks to guide decisions.
• Decide which meetings to record by setting expectations, understanding legal/consent needs, and only recording when there is a defensible reason to keep it.
• Scale an AI pilot when measured outcomes hit agreed benchmarks, including ROI and intangibles like morale and “intelligence debt.”

💡 Key Takeaways

• Trust is earned over time. Use oversight at first, then loosen it only as the system proves itself repeatedly.
• If data is sensitive, don’t start with frontier use cases. Start with safe tasks and align adoption to org policy and vendor compliance requirements.
• Recording is not default permission. Socialize expectations, declare the recording approach, and be ready to stop if the topic crosses privacy lines.
• Scaling is not about vibes. Define pilot success metrics up front, then compare benchmark results against your trade-offs. Don’t confuse speed with accuracy. Measure both where you can.

❓ Questions That Mattered

• How do I know when to trust AI at work versus slow down and check it?
• If I work with protected data, what are the first steps to use AI safely and compliantly?
• Which meetings should be recorded by default, and where are the privacy boundaries?
• What should an AI pilot prove before a company scales it, and when should it stop? (Also: how do we choose the right tools and train people as they change?)

🗣️ Notable Quotes

• Trust with humans is built over time, so with AI you should start slow too.
• Accuracy through repetition moves your trust level up, especially when you have a rubric or rule set to measure against.
• If it’s not clear why you’re recording, why are you doing it?
• You might have a massive increase in employee morale and happiness, but the ROI might not match right away, and that trade-off matters.

🔗 Links & Resources

• Listen To Other Episodes Co-Hosted With Justin

🧠 Erik’s Take

Erik 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. The stakes change, the tools change, the mission context changes, but the interpersonal variables stay stubbornly human. Erik’s takeaway is that culture cannot be left as vibes, slogans, or “someone will handle it.” It has to be engineered into the operating reality: articulated, localized, inspected, grown, normalized, and sustained.

🎯 Top Insights from the Interview

• Humans remain the most unpredictable system variable, even when the mission looks wildly technical.
• Interpersonal dynamics persist through growth, even when the org and tools get bigger and the consequences get heavier.
• ALIGNS reframes culture as an operating system, not a poster, by making the how visible and repeatable.
• A real business stage exists where culture infrastructure must arrive before a full internal enablement team does.

🧩 The Personal Layer

Erik admits he initially resisted the “playing house” framing because it can sound like it minimizes stakes. But he sees John’s sharper point: it is not about lowering stakes, it is about acknowledging that the interpersonal dynamics do not scale away. Erik also notices the practical discomfort in his own leadership instincts, especially around accountability conversations. His mind keeps returning to the same pattern: what gets rewarded and avoided becomes the real culture, whether leaders explicitly intend it or not.

🧰 From Insight to Action

• Audit the “how” in your organization: where do people learn what matters through rewards, norms, and silence?
• Operationalize culture with a repeatable loop: articulate expectations, localize them by role, and inspect whether reality matches the language.
• Build culture infrastructure earlier than you think you need it, especially before growth fractures informal norms into microcultures.
• Create safe pathways for the hard thing to be said sooner, so truths surface before they become expensive failures.

🗣️ Notable Quotes

• We’re all just playing house, but the house gets bigger, the tools get better, and the consequences get heavier.
• If humans are one of the most unpredictable variables, then it would be poor engineering not to design around them.
• Culture isn’t just something you believe in. It’s something you have to define, inspect, reinforce, and maintain.
• If you don’t define the how, people will make it up. Usually not maliciously. Usually not consciously.

🔗 Links & Resources

• Listen to John Marshall's Episode

🧠 Erik’s Take

Erik 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 supply chain as a proving ground for trust. He kept returning to the same paradox: when everything is working, it looks normal, but when it breaks, the organization suddenly realizes how much invisible work has been happening all along. The practical tension that stuck with him is that leaders often budget for supply chain as a cost. The interview reframed it as operational trust,

🎯 Top Insights from the Interview

• Supply chain failures are often symptoms, but someone still has to do the hidden work to make reality match the plan
• The say/do ratio is internal trust currency, and it determines whether people believe hard messages as truth or as excuses
• Last-mile is not just transportation, it is communication lag between consumption, vendors, and stakeholders
• Technology creates leverage only when it targets real communication delays and preserves human judgment

🧩 The Personal Layer

Erik noticed he naturally talks about systems, software, and process improvements, but this conversation pulled him back toward a human-centered definition of competence. He resonated with the idea that supply chain can be accountable for everything while being held responsible for nothing. That dynamic mirrors other leadership spaces where one team owns the outcome but not the initial cause. He also felt a personal nudge: his credibility is not a personality trait, it is a pattern created by closing loops, telling the truth early, and following through often enough that people stop second-­g­

🧰 From Insight to Action

• Audit where communication lag creates waste or surprise, then pick one delay to fix instead of adopting tools for their own sake
• Build a say/do habit in leadership: commit clearly, update early, and document what you promised versus what happened
• Treat supply chain partners as trust builders, not just cost centers, and align incentives to resilience outcomes
• Strengthen the “who to call and what to ask” capability by capturing playbooks for breakdown moments

🗣️ Notable Quotes

• Supply chain is like duck feet paddling under the water, smooth on top, work everywhere beneath.
• The say/do ratio is the currency of trust inside the company.
• When you’ve earned credibility, you can deliver bad news without drama.
• The last-mile problem is also a communication problem, not only a transportation problem.

🔗 Links & Resources

• Listen to John Kill's Episode

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 missions teams can handle stress, conflict, and sabotage. The goal is mission performance and accelerated learning, powered by psychologically safe, conflict-ready culture that scales.

👤 About the Guest

John Marshall is founder of Humescence, a human-centered leadership and cultural development company. His work blends executive coaching, immersive leadership training, and culture enablement consulting. He helps leaders turn individual self-understanding into collective capability by aligning systems with how humans actually think, feel, and behave.

🧭 Conversation Highlights

• The “interplanetary mission team” problem: interdependence, prolonged isolation, and high-stakes stress amplify default interpersonal patterns.
• Culture as an engineered system: optimize for human capacity, not just avoid catastrophes, and create feedback loops that measure and improve.
• A framework called ALINES: articulate, localize, inspect, grow, normalize, sustain to make culture actionable and scalable.
• Why live, human facilitation matters for heart-centered skills, beyond what information alone can deliver.

💡 Key Takeaways

• Tech is increasingly abundant, but competitive advantage is the human element: how people communicate, integrate insights, and work through conflict.
• A culture that works is not “nice.” It is psychologically safe, explicitly conflict-capable, and built to surface what would otherwise stay unsaid.
• Default behaviors are rooted in subconscious “operating systems,” so change must happen at deeper levels, not just via training content.
• Sustainable culture requires systems that persist through hiring, onboarding, performance reviews, coaching, and leadership transitions.

❓ Questions That Mattered

• If stakes are higher, why do interpersonal dynamics still revert to basic human needs and triggers?
• How do you engineer culture so it produces predictable outcomes without flattening human differences?
• What forcing functions are pushing companies to address culture earlier instead of reactively after attrition or conflict?
• Why does John emphasize in-person, human-to-human facilitation when digital training is easier?

🗣️ Notable Quotes

• “The last frontier for us would be scaling the systems so we can solve for interplanetary travel.”
• “A psychologically safe culture should actually be highly competitive, conflict driven.”
• “Culture isn’t ‘we all get along’. This is the emotional workplace.”
• “Ninety percent of the gold comes off of questions because of the live, facilitated experience.”

🔗 Links & Resources

• Follow John Marshall's LinkedIn
• Check out Humessence.com

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 ripple effects, and why supply chain teams fail only when “the wheels come off.” He also digs into low-risk practice, leadership trust, vendor relationships, and how AI should augment people, not replace them.

👤 About the Guest

John C. Kill is a seasoned supply chain leader with 25 years in procurement and resilience. He has held senior roles at GE Transportation, Vestion, Bluebird Corporation, and Finish Thompson, and most recently served as Chief Procurement Officer at Vesa Manufacturing, including rapid rescues when suppliers fail. An MBA holder and Six Sigma Greenbelt, he also contributes through Penn State business.

🧭 Conversation Highlights

• Supply chain is “accountable for everything but responsible for nothing,” so success demands breadth, tenacity, and relationship skill.
• Current headwinds include trucking/driver shortages, logistics consolidation, downstream impacts from global disruption, and weather-driven supplier failures.
• Failure prevention is built through “low-impact” exercises that train teams to respond like it’s the end of the world, without real catastrophe.
• Trust and leadership in crises rely on a strong “say-do ratio,” plus honest, non-offensive communication up and down the org.

💡 Key Takeaways

• Great supply chain work is practiced, not improvised: run controlled simulations so real emergencies feel familiar.
• Relationships are operational infrastructure. Vendors help faster when they stay profitable and treated fairly.
• AI is best used to save grind work and expand capability, while preserving human judgment and entry-level learning.
• Resilience comes from drilling beyond direct suppliers and using dashboards for multi-layer risk, not just stocking inventory.

❓ Questions That Mattered

• Why does supply chain stay under the radar until disruption enters the national lexicon?
• What does it feel like internally when supply chain “fails,” and what does recovery actually require?
• How do you teach teams to handle expensive crises by rehearsing low-risk versions first?
• How can supply chain become a strategic advantage, not just a cost center, especially post-COVID?

🗣️ Notable Quotes

• “It’s the duck sliding across the pond. You don’t see how furiously the little webbed feet are paddling underneath.”
• “In the supply chain world, we’re accountable for everything but responsible for nothing.”
• “Give your people low-impact exercises so they build muscle memory before the true crisis.”
• “If you can’t tell harsh truths with care and concern, you won’t earn the trust people need to follow you.”

🔗 Links & Resources

• Follow John Kill's LinkedIn

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.

🧭 Conversation Highlights

• AI updates follow iterative deployment, so changes land when features are ready, not on a schedule, and teams often notice only when something breaks.
• Justin argues for an “AI champion” steward who monitors release notes, tests impacts, and keeps adoption coherent across the organization.
• They debate the real value of integrated voice and “rambling,” clarifying the difference between dictation mode and interactive conversational voice.
• Key release-note examples include GPT Live voice, ChatGPT Work (desktop and web), and retiring Atlas, with browser functionality moving into the ChatGPT desktop app.

💡 Key Takeaways

• Treat AI updates as a continuous operating condition, not an occasional event, and plan for ongoing process iteration.
• You can automate the “watching” with agents, but humans still need to validate what changed and what it affects in your specific workflows.
• Don’t frame browser-tool changes like Atlas as failure. Reframe as consolidation into a more integrated “work inside the app” model.
• Clarity and role ownership matter. Small, focused teams with clear AI use cases adapt faster than teams that keep spinning up committees.

❓ Questions That Mattered

• How do you stay updated when AI platform changes arrive without a predictable schedule?
• What’s the right balance between automated monitoring (agents) and human interpretation?
• Does more conversational, live voice reduce the usefulness of “rambling,” or does it complement other voice modes like dictation?
• When tools like Atlas disappear, how should leaders communicate the change so it does not feel like chaos or constant churn?

🗣️ Notable Quotes

• “In this era of AI, we’re in the era of iterative deployment… No one’s going to tell you a new update’s happening.”
• “So you as a human being… the representative of the advancement of AI in your organization, you still need to read it.”
• “It is possible… [but] you still need to read it. You need to be on the forefront.”
• “I would increase your sometimes to, you know, almost an absolute of always.”

🔗 Links & Resources

• Listen To Other Episodes Co-Hosted With Justin

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 “experiments” to replace gut-feeling with confidence.

🧭 Conversation Highlights

• Erik frames the moment of realizing someone may be at “the ceiling” as uncomfortable, doubly so because leaders worry they could be wrong or be the problem.
• Alli shares her own example: she suspected a direct report had hit capacity, but she later discovered the issue was role fit and the person rose after adjustments.
• They discuss how to diagnose the real situation: Alli emphasizes mentorship, peer feedback, and mapping what the role actually needs against what the person does well or not well.
• Erik adds a practical approach: create a time-bound experiment and ask, “Why do I believe this will ever be different?” so the leader can act from reality, not fear.

💡 Key Takeaways

• Before you act, separate role fit from capacity. Sometimes the ceiling is really a mismatch between what the job demands and what the person is wired to deliver.
• A first step can be admitting the possibility to yourself (and only then, as needed, to others). It’s intimidating, but avoiding it usually keeps the problem hidden.
• Short, structured tests beat vague optimism. Build an “experiment” that answers whether improvement is likely within a reasonable timeframe.
• Even if someone cannot grow into the hardest parts of the role, that doesn’t automatically mean exit. Think about how to keep them in the work they do well, with honest expectation-setting.

❓ Questions That Mattered

• Is this person genuinely at their ceiling, or are they in the wrong role for what they do best?
• Am I the one getting in their way, or have my expectations and feedback been unclear?
• What evidence do I have that change is possible in a short, meaningful timeline?
• If they cannot do the top requirements, what is the right long-term plan for how they contribute?

🗣️ Notable Quotes

• “We rise to our highest level of incompetence.”
• “Fun fact of the day: you never surprise people in a performance review.”
• “If you're willing to acknowledge that... what if I'm wrong? What if I'm the problem?”
• “Why would I believe this will ever be different?”

🔗 Links & Resources

• Listen To Other Episodes Co-Hosted With Alli
• Check out Alli's Skool Community

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 Gregory Kovsky, President and CEO of International Business Associates (IBA), to unpack the realities of business brokerage, M&A advisory, and what separates elite dealmakers from average brokers. Gregory shares lessons from more than 30 years in the industry, including why so many businesses never sell, how experience changes outcomes, and why communication—not information—is often the most valuable asset in a transaction.

Along the way, they explore negotiation, AI, leadership, business evolution, and the surprising similarities between business brokerage and heart surgery.

👤 About the Guest

Gregory Kovski is President and CEO of International Business Associates (IBA), the Pacific Northwest’s oldest and largest business brokerage firm. With 30+ years of experience and 300+ personal transactions, he leads a team across 10 offices in Washington and Oregon and has helped complete 4,400+ deals. He blends brokerage, finance, and licensing expertise, and publishes and speaks on buying and,

🧭 Conversation Highlights

• Why barriers to entry are too low for what business brokerage actually demands
• The “three tiers” of communication: articulate, educate, persuade
• A broker’s job is to spot yellow flags, then pull in the right experts fast
• Industry-specific nuance and process discipline matter for long, emotionally loaded retirement exits

💡 Key Takeaways

• Business brokerage is not one skill. It spans accounting, taxes, finance, law, insurance, real estate, licensing, and psychology.
• A good broker is a facilitator: recognize risk, educate clients, and coordinate experts, not claim omniscience.
• Communication wins deals: clarity in the moment, plus referenceable written materials.
• Screen brokers like you’d screen a surgeon: track record, specialization, and experience under pressure.

❓ Questions That Mattered

• What should the minimum licensing and continuing education bar be for business brokers to match the complexity of the work?
• Why do so many deals fail or leave sellers regretting the outcome, and what predicts those outcomes?
• How is technology and AI changing information asymmetry in business sales, and why does lived execution still matter?
• How should an entrepreneur vet a broker: personal trust, firm scale, and industry-specific experience all at once?

🗣️ Notable Quotes

• “A good business intermediary needs diverse knowledge and experience to professionally represent their client.”
• “Our job is to get people to shake hands.”
• “If you don’t know about them, if you don’t understand them, how can you guide a client through that sale process?”
• “There’s nothing good that happens from forcing anything.”

🔗 Links & Resources

• Follow Gregory Kovsky's LinkedIn
• Check out IBA’s Website: ibainc.com