I Have Some Questions...

Erik Berglund
  • 5.0 (42)
  • Management
  • Updated Daily

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. 

  1. 22h ago

    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 success as an engine for opportunity across employees, families, and communities. 👤 About the Guest Scott Lauray is founder and principal of ProVia Partners, delivering business valuation, M&A advisory, and fractional CFO support for privately held companies. After leadership roles in large international organizations, he shifted in 2010 to focus on the entrepreneurial middle market and build guidance tailored to owners preparing for growth and ownership transitions. 🧭 Conversation Highlights How valuation and transaction advisory support practical owner decisions, not just accounting outputsWhy the entrepreneurial middle market needs tailored financial leadership and strategyPreparing for ownership transitions by strengthening enterprise value before major movesThe bigger purpose: business success as a driver of opportunity for communities💡 Key Takeaways Good valuation work should map to owner intent and real-world decision-making.M&A readiness is built over time through stronger operations, financial clarity, and strategy.Fractional CFO leadership can bridge gaps between growth and disciplined execution.Owner success creates ripple effects across employees, families, and local communities.❓ Questions That Mattered What does enterprise value mean in the context of an owner’s actual goals and timing?What signals whether a business is truly “sale-ready” or “transition-ready”?Where do many owners underestimate the planning required for successful outcomes?How can financial advisors translate complex analysis into clear next steps for leadership teams?🗣️ Notable Quotes “Businesses create opportunity, and when owners succeed, employees, families, and communities benefit.”“I made a deliberate shift in 2010 to focus on the entrepreneurial middle market.”“Our team performs business valuation services and supports privately held M&A and strategic financial leadership.”🔗 Links & Resources Follow Scott Lauray's LinkedIn

    221: Scott Lauray: "The Quiet Metrics That Increase Saleability"

  2. 1d ago

    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 and the Four Languages (read, see, hear, experience), plus why trust, authenticity, and even lighting and audio matter for message delivery. 👤 About the Guest Joshua Altman is an experienced storyteller and strategist who leads Beltway Media, a DC-based communications firm. With over two decades of experience, including multimedia journalism at The Hill covering high-stakes federal policy and elections, he now helps startups and agencies refine messaging, elevate brand, and build trust with customers, investors, and the public.  🧭 Conversation Highlights Joshua explains fractional comms as an internal-employee model: take 10 to 20 hours a week off founders and leaders who are doing communications ad hoc.Two frameworks anchor the work: Story-Narrative-Brand and the Four Languages model (read, see, hear, experience) to map how audiences actually take in information.They push for early engagement, even day one, because shaping perception and building trust are easier before misinformation or negative impressions take hold.Trust and authenticity beat polished “AI slop,” and even simple production basics like clear audio and decent lighting are required for the message to land.💡 Key Takeaways Communications is always happening, so the goal is to make it intentional and organized, not just louder.Mapping message through read, see, hear, and experience reveals gaps across touchpoints like ads, pitch decks, hold music, and events.Fractional works best when it is not “one-off projects,” but an ongoing process with a minimum commitment and a seat at the table from early on.Authenticity builds trust, but only if your content is actually perceivable: good enough audio and lighting are non-negotiable.❓ Questions That Mattered How can a company recognize it is doing “random acts of communication” without measuring time, control, or strategy?Why are strategy and frameworks more valuable than simply removing the CEO’s communications burden?What truths must a business accept before fractional comms makes sense (even from day one)?If “crazy” sometimes works, how do you know when experimentation creates upside versus unintended negative consequences?🗣️ Notable Quotes “Unlike an agency we are there like an internal employee, but fractionally.”“Communications is an ongoing process. You’re always doing it, whether you’re thinking about it consciously or not.”“Authenticity almost always [is] the deciding factor, with a couple of caveats.”“Quantify how much time you are spending on this.”🔗 Links & Resources Follow Joshua Altman's LinkedInCheck out Beltway Media

    220: Joshua Altman: "How Much Is Disorganized Comms Really Costing You Per Month?"

  3. 2d ago

    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 Highlights Justin defines super apps as AI workspaces that combine model access, agents, and computer or browser use in one interface.Erik pushes on the human side of adoption and asks whether waiting for the tech to mature actually reduces the real cost.They discuss how change management needs education, executive buy-in, and AI champion teams that represent more than just IT.Justin explains context windows (AI attention span) and then tokenomics: tokens measure workload, credits measure billing, and measurement is still messy.💡 Key Takeaways Super apps are less about a new tool and more about consolidating how work happens, which forces a new way to interact with your systems.Waiting for “fully baked” AI does not remove the human adoption problem. Humans are slower, so competitors build advantage while you stand by.Good adoption looks like: leadership using it, education for everyone, and an AI champion group embedded across functions.Tokenomics and context windows are becoming operational concerns. If you cannot measure and manage usage, costs and performance turn into guesswork.❓ Questions That Mattered Will adopting super apps get easier from a change management standpoint, or will it keep demanding constant iteration from teams?How should companies think about their tech stack being partially commoditized and what pushback comes from the original tools?If a super app depends on a small number of operators, what happens when key people leave and the wiring breaks?What does it mean when an AI says the chat is too long, and how should teams manage context and summarize threads?🗣️ Notable Quotes “Humans need their hand held until they don't.”“Context window is your AI's attention span.”“Tokens measure the underlying AI model's workload. Credits are the product's own usage and billing currency.”🔗 Links & Resources Listen To Other Episodes Co-Hosted With JustinRead the Article 'What a Forgotten 100-Year-Old Government Report Says About Who We Are'

    219: "Why You Cannot Shortcut The Human Part Of AI Implementation" ft. Justin Coats

  4. 6d ago

    218: "Is Promising Outcomes the Worst Thing We Could be Doing?" (Reflections On Jaclyn Orent)

    🧠 Erik’s Take Erik 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 define the result, set the plan, and solve the problem. He keeps circling back to three tensions Jaclyn named: letting go is a skill, specificity can become a ceiling, and early goals can manufacture clarity without actually creating it. He also noticed something personal while reviewing the episode: high-performing patterns are often strategies to avoid feeling first, and that shows. 🎯 Top Insights from the Interview Letting go is practical when it becomes a sequence: feel what is real, release judgment, then accept reality without rushing to fix it.Outcome-selling can unintentionally limit value when the promised result becomes a ceiling, especially in developmental and leadership work.Premature goals create a forcing function that shapes attention and decisions before the vision is actually clear, making certainty feel manufactured.🧩 The Personal Layer Erik admitted that his own strengths can become constraints. He recognizes how easily the impulse to solve can be a way to escape discomfort, and how often his brain wants to reduce uncertainty immediately. He also felt a sharper sensitivity around “defining the result” because it is how he has been rewarded in business. The episode challenged him to loosen the grip without losing direction, to create enough clarity to move while leaving room for emergence. 🧰 From Insight to Action Practice Jaclyn’s three-step letting-go loop before problem-solving: name the feeling, drop the good-or-bad judgment, then accept what is true right now.When offering outcomes, separate “bounded deliverables” from “developmental impact,” and explicitly leave space for value that can expand beyond the first container.Before committing to a measurable goal, ask whether the underlying vision is truly clear, or whether the goal is mainly managing the discomfort of uncertainty.🗣️ Notable Quotes Letting go isn’t a simple decision. It’s a sequence: feel what you’re feeling, release the judgment, and accept reality as it currently exists.Sometimes the thing creating progress is also the thing limiting what might be possible.A number can create the feeling of clarity without creating actual clarity.Exploration and commitment are both valuable, but they need to happen in the right order.🔗 Links & Resources Listen to Jaclyn Orent's Episode

    218: "Is Promising Outcomes the Worst Thing We Could be Doing?" (Reflections On Jaclyn Orent)

  5. 6d ago

    217: "How Do You Create AI Coaching That Adapts Over Time?" (Reflections On Gavin Lorenzo)

    🧠 Erik’s Take Erik 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 person learns, gets stuck, adapts, and responds. He also feels the conversation complicate the regulation instinct. It is not just “should we regulate,” but “who gets to decide what these tools can do” and what values get embedded. Finally, he leaves with a more intellectual spark: if AI can model people well enough, it could turn theories of human behavior into operating hypotheses, 🎯 Top Insights from the Interview Understanding is not the same as remembering. Erik reframes Tellbloom-style personalization as building a predictive model of how someone operates over time.Regulation is a second-order question of governance. The real issue is who decides access, capabilities, and embedded values.AI-enabled human modeling could enable falsifiable learning loops. Erik highlights the move from “a theory sounds right” to “does it improve the interaction.”Ethics is not cleanup work after launch. Erik emphasizes privacy, consent, and transparency as product design constraints, not paperwork.🧩 The Personal Layer Erik notices his own friction point: he agrees AI needs guardrails as capability grows, yet he worries regulation can be captured, slow, or incentivized toward incumbents and politics. He also recognizes the temptation to reduce personalization to “better memory” because it is measurable and easier to ship. The episode pushes him to hold a more demanding standard: if the interaction is coaching, education, leadership, or decision support, then the product has to adapt with real human-level nuance, not generic helpfulness. 🧰 From Insight to Action If you are building or buying AI that interacts with people, define “understanding” as a behavior-improving capability, not just personalization as recall.Design governance into the product. Make transparency, retention limits, and consent visible to users from day one.Treat people frameworks as testable operating hypotheses. Instrument the experience so you can measure whether a model improves outcomes for that person.When discussing regulation, shift the conversation from slogans to decision rights: who sets capabilities, who audits, and how values are encoded.🗣️ Notable Quotes “Understanding isn’t the same thing as memory.”“The deeper question is: who gets to decide what these tools can do.”“Move from ‘this theory sounds right’ to ‘this model either improves the interaction or it doesn’t.’”“If your product helps AI understand people more deeply, then privacy, consent, transparency, and use aren’t cleanup work later.”🔗 Links & Resources Listen to Gavin Lorenzo's Episode

    217: "How Do You Create AI Coaching That Adapts Over Time?" (Reflections On Gavin Lorenzo)

  6. Aug 13

    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 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 LinkedInCheck out the Cultural Catalyst NetworkPower 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. MaxwellGene Keys: Unlocking the Higher Purpose Hidden in Your DNA — Richard Rudd.

    216: Jaclyn Orent: "Your Founder Problem Isn't Lack of Clarity, It's Avoiding Letting Go"

  7. Aug 12

    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. 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 LinkedInContact Gavin at gavinlorenzo11@gmail.com

    215: Gavin Lorenzo: "Can AI Actually Understand Humans Without Human-Grade Self-Awareness?"

  8. Aug 11

    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 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

    214: "Accuracy Through Repetition: When Should You Let AI Work More Independently?" ft. Justin Coats
See All (219)

5
out of 5
42 Ratings

About

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. 

Information

  • Creator
    Erik Berglund
  • Years Active
    2025 - 2026
  • Episodes
    219
  • Rating
    Explicit
  • Copyright
    © 2026 I Have Some Questions...
  • Show Website
    I Have Some Questions...

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