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 appl

I Have Some Questions... is a business podcast hosted by Erik Berglund, with 216 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Erik Berglund hosts I Have Some Questions..., a business show with 216 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #221

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

  Aug 20, 20261h 26m

  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 outputs Why the entrepreneurial middle market needs tailored financial leadership and strategy Preparing for ownership transitions by strengthening enterprise value before major moves The 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

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  Episode #220

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

  Aug 19, 202657 min

  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 LinkedIn Check out Beltway Media

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  Episode #219

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

  Aug 18, 202657 min

  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 Justin Read the Article 'What a Forgotten 100-Year-Old Government Report Says About Who We Are'

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  Episode #217

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

  Aug 14, 202610 min

  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

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  Episode #216

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

  Aug 13, 20261h 16m

  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.

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