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. 1d ago

    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 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 Kowski 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 demandsThe “three tiers” of communication: articulate, educate, persuadeA broker’s job is to spot yellow flags, then pull in the right experts fastIndustry-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 LinkedInCheck out IBA’s Website: ibainc.com

    207: Gregory Kovsky: "The Hidden Barriers To Becoming a Real Business Broker"

  2. 2d ago

    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. Drawing from decades of experience spanning hospitality, technology, finance, HR, and operations, Olivia shares why culture isn't a soft concept—it's a business system. Together, they unpack the post-COVID shift in employee values, the hidden power of hospitality leadership, Disney's remarkable employer brand, and why resilient cultures behave more like lungs than rulebooks.  👤 About the Guest Olivia Bryant is a culture strategist, operations leader, and Chief Operating Officer executive whose career spans hospitality, enterprise technology, finance, and organizational development. After helping lead large-scale people initiatives—including work surrounding the historic Citrix-TIBCO merger—Olivia returned to her roots in hospitality, where she now helps restaurant organizations blend operational success with purposeful culture-building. She is also the creator of The Culture Chat, where she explores leadership, culture, and the future of work. That podcast is filled with insightful conversations about organizational culture and best practices that drive success in today’s diverse workplace.  🧭 Conversation Highlights Culture as an operational system: belief, resilience, assimilation, and accountabilityTurning data into real decisions: guest sentiment, reviews, sales signals, and milestonesHiring and onboarding for “people who chose the industry as a career,” not just a jobChange management recipe: buy-in, change champions, honest pain points, and measurable progress💡 Key Takeaways Culture is happening either way. The choice is whether you build it consciously and measure what matters.Data closes the loop, but it has to become action via milestones, feedback, and training.Strong hospitality cultures run on belief and reinforcements, not posters and perks.Resilient culture needs cadence, flexibility, and a tolerance for fluctuation during change.❓ Questions That Mattered How do you hire for genuine buy-in and not just enthusiasm you can say in an interview?What feedback loops actually improve the guest experience beyond lagging KPIs?What makes culture on purpose resilient through leadership changes and major shifts?How do you gather “data not anecdotes” without undermining human service?🗣️ Notable Quotes “If you don't have accountability you have culture, but it's probably not the culture anybody wants to be part of.”“Culture on purpose needs resilience, like lungs that can compress and expand through change.”“The heartbeat of culture is what people actually live, not what’s on the poster.”“The statement is: it's being built regardless. You're either building it consciously or you're building it unconsciously.”🔗 Links & Resources Follow Olivia on LinkedInCheck out Vine Hospitality's Website: vinehospitality.comListen to ‘The Culture Chat’ Podcast

    206: Olivia Bryant: "Culture Breaks When Values Become Words"

  3. 3d ago

    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 because humans add customer value. 🧭 Conversation Highlights AI can replace tasks, but it does not automatically replace jobs, because jobs are bundles of quality, judgment, coordination, and accountabilityCustomer value is what expands markets, and AI can help companies identify where humans actually add valueCoding, radiology, and customer-facing roles show the pattern: automation changes work, it does not necessarily reduce the number of rolesHistorically, technology threats often follow a paradigm shift (ATMs versus digital banking), not the technology itself (the iPhone point) instead of the ATM point alone (teller work)💡 Key Takeaways Job displacement will be real for individuals, and transitions can be painful, but the larger scale effect may be more opportunity createdMcDonald’s kiosks illustrate the idea that automation can redirect human time toward customer experience roles, not necessarily cut headcountEven where AI is a strong tool (developers, radiology), the human contribution often shifts to architecture, security, care coordination, and patient guidanceThe risk of mass job loss is more tied to whether markets shrink due to paradigm shifts, not whether AI exists❓ Questions That Mattered How do we distinguish AI replacing tasks from AI replacing entire jobs?Where, in a specific company, do humans add the most customer value, and can AI reveal that faster?Is the real threat to jobs the automation itself, or the paradigm shift that changes customer behavior and market demand?When creative tools automate production, what happens to the overall market for creative services, and who gets new access?🗣️ Notable Quotes “AI is good at replacing tasks, but not really automatically replacing jobs.”“Jobs are made or lost because markets grow or shrink.”“The technology itself isn’t what's going to take it. It's the replacement of the task… that’s when people no longer need you.”“The future isn’t jobless. The future isn’t… high income everywhere. It is very redesigned around more and more human value.”🔗 Links & Resources Listen To More Solo EpisodesGoldman Sachs — How Will AI Affect the US Labor Market?Anthropic — The Anthropic Economic IndexJames Bessen / IMF — Toil and TechnologyAmerican College of Radiology — The Radiologist Shortage: A Workforce UpdateCNN — McDonald’s Touchscreen Kiosks Were Feared as Job Killers. Instead, Something Surprising Happened

    205: AI Will Disrupt Tasks, Not Entire Jobs

  4. 4d ago

    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 solve the problem on their side of the table. 🧭 Conversation Highlights Delegation often reveals process, skill, or expectation breakdowns that were already present, especially when you assign “new-to-them” work.Don’t confuse urgency with control: jumping in too aggressively can damage trust and make people afraid to take the next opportunity.Use a conversation to coach: get curious, ask open-ended questions, clarify success, and help them build their own repeatable approach.In high-pressure moments, you may need to help or provide options, but preserve agency so the person learns and owns the outcome.💡 Key Takeaways Treat delegation failures as “visibility,” not proof of incompetence. The flashlight was just overdue.Protect trust while solving the problem. If the person feels vulnerable, your response can either build safety or shut it down.Your goal is repeatability, not just getting the current project finished. Empower the person to solve it again in the future.When you must intervene for timeline or stakes, do it in a way that still keeps the person in charge of choices and next steps.❓ Questions That Mattered What “rats or spiders” are showing up when delegation isn’t working, and what breakdown is actually underneath it?What does success look like to you, and where do we meet versus where do we miss?How do we enhance trust so the person can ask for help and learn instead of hiding mistakes?When urgency forces you to step in, how can you still preserve the person’s control and ownership?🗣️ Notable Quotes Delegation is just finally revealing that those things were going wrong the whole time.The problems were already there, and now you can finally fix them.If you can remember that the person you're leading in this situation is vulnerable, and if you insert yourself aggressively back into it, you will tear to shreds whatever trust you might have been b uThe next time you delegate, you'll have a lot more confidence because you went through that with them.🔗 Links & Resources Listen To Other Episodes Co-Hosted With AlliCheck out Alli's Skool Community

    204: "How To Coach Through The Delegation Mess" ft. Alli Murphy

  5. Jul 23

    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, why stable cash flow beats optimistic projections, and what separates companies that are attractive acquisition targets from those that struggle to command premium valuations. Along the way, they explore the differences between private equity and venture capital, the frameworks Speycide uses to evaluate businesses, and why AI, robotics, and Industry 4.0 technologies may reshape the future of North American manufacturing. 👤 About the Guest Eric Wiklendt is the Managing Director of Speycide Equity, a private equity firm focused on acquiring and growing middle-market manufacturing businesses. Before joining Speycide, Eric served as President and CEO of Kellex Heat Transfer Systems and held leadership roles at Eaton and Hilti. His background spans mergers and acquisitions, manufacturing operations, strategy, and value creation across industrial businesses. Today, he helps identify, acquire, improve, and grow manufacturing companies through what Speycide calls a "Fix and Build" strategy. 🧭 Conversation Highlights The Difference Between Corporate Acquisitions and Private Equity. Eric explains that corporate buyers and private equity firms may both acquire businesses, but they play entirely different games. Corporate acquirers typically buy businesses under the assumption of long-term ownership and focus heavily on strategic synergies. Private equity firms operate within defined hold periods and focus on creating measurable value that can be realized within a specific timeframe. The result is a fundamentally different approach to evaluating opportunities, structuring deals, and defining success. The Hidden Framework Behind Value Creation. Eric walks through Speycide's internal system for evaluating businesses: Portco Value Creation System (PVCS)Multiple Accretion Framework (MAF)Process Assessment Framework (PAF)Human Capital Assessment Framework (HCAF)Together, these frameworks help answer a single question: With demographic trends creating long-term workforce shortages, he sees AI, robotics, automation, digital twins, and advanced manufacturing technologies becoming essential infrastructure rather than optional upgrades. In his view, the factories of the future won't eliminate people—they'll shift people into maintaining and improving the systems that run production. 💡 Key Takeaways Private equity and venture capital operate under fundamentally different return models.Great investors underwrite controllable outcomes, not optimistic possibilities.Stable, repeatable cash flow is one of the most valuable characteristics a business can possess.Process quality often matters more than individual talent.Human capital remains the hardest variable to predict in any business.A single source of truth creates alignment and better decision-making.❓ Questions That Mattered What makes private equity different from corporate acquisitions?How should founders think about building a company that someone wants to buy?Why do investors care so much about process and cash flow?How do you evaluate human capital before acquiring a business?What makes a company scalable?🗣️ Notable Quotes "We don't pay for anecdotes and assertions. We pay for cash flow." "What we really want are companies with $100 million revenue, with systems, processes, and people." "Culture tells people what to do when nobody is telling them what to do." "Together everybody achieves more." 🔗 Links & Resources Follow Eric Wiklendt on LinkedInCheck out Speyside’s Website: speysideequity.com

    203: Eric Wiklendt: "What No One Talks About in M&As About Adding Value"

  6. Jul 22

    202: Vincent Azzolina: "What Does It Take to Lead in a Zero-Mistake Environment?"

    Vince Azzolina shares how his career pivoted from CFO to COO at Myers Wells Service, moving from behind-the-scenes finance to hands-on operational leadership. They discuss incentives, the shift from cost-per-barrel to hourly pay to reduce unsafe driving, and how safety and engagement became core to profitability and retention. 👤 About the Guest Vince Azzolina is COO of Myers Wells Service, an oil and gas trucking provider headquartered in Western Pennsylvania. He leads financial performance and strategy while overseeing business operations. Previously, he worked at Volvo North America running purchasing for Volvo and Mack in North America. 🧭 Conversation Highlights Why his CFO-to-COO transition happened in the 2019 timeframe, driven by ownership wanting deeper operational engagementHow rate model changes and a safety bonus program helped reduce speeding and accident severityWhat it takes to lead through high-pressure, demanding customer environments and equipment availability challengesHow technology and AI are being explored to ease admin load, improve maintenance, and strengthen safety systems💡 Key Takeaways Aligned incentives can drive performance, but they must be designed to avoid unintended safety pressure.Safety culture is both a values system and an economic strategy through reduced accidents, insurance exposure, and turnover.In a service business, people are the primary asset, so training, communication, and trust are operational strategies.AI and new tech are only useful when they remove real operational pain, like Excel-heavy reporting and integration gaps.❓ Questions That Mattered How do you grow as a leader when you shift from CFO comfort with data to COO needs for trust and delegation?What incentive design reduces unsafe behavior without undermining delivery performance?Is safety truly more profitable, and where does the economics show up beyond lawsuits and insurance?What does “predictive” safety look like when human factors like fatigue are involved?🗣️ Notable Quotes "There are a lot of things that aren't our fault but are still our responsibility.""If you're a safe company, you're a profitable company.""Our people are our asset.""I've become a big believer in engagement and being present.""I don't need to be meddling in this. I trust them.""I would love to look back three years from now and say we figured out how to use AI to make our people's lives easier.""We want people to retire here.""Safety is the first topic of discussion with every customer and the first topic of discussion inside our company."🔗 Links & Resources Follow Vincent Azzolina's LinkedInCheck out Myers Well Service’s Website: myerswellservice.com

    202: Vincent Azzolina: "What Does It Take to Lead in a Zero-Mistake Environment?"

  7. Jul 21

    201: "Vision First Or Tools First: The Hidden Step Before Any AI Implementation" ft. Justin Coats

    Erik and Justin unpack Paul Rotzer’s AI maturity “eight pillars” and use it to frame what leaders should do after the hype: step back, explore what AI can do, choose a priority problem, then build vision, strategy, governance, literacy, and measurement in that order. 🧭 Conversation Highlights AI adoption is a forcing function: excitement about what AI can do often triggers the harder question of what the business should actually solve first.Justin argues for a mindset shift from “pick the perfect problem” to acknowledging an unsolved problem set, learning AI capability, then applying it deliberately.Governance quickly turns practical as teams hit token limits, spend tracking gaps, and model availability changes during real adoption.Early value often starts in communication and as an individual thought partner, but real ROI comes when leaders provide guardrails, education, and space to iterate.💡 Key Takeaways Start with exploration, but don’t skip selection: the ability to do many things can paralyze you if you do not stack-rank what matters.Vision and literacy shape what happens next. Without a clear “why AI,” tool knowledge alone will not translate into durable adoption.Adoption is iterative: one department, one strategic goal, then replicate. “Go slow to go fast” beats trying to tackle everything at once.Token cost governance is becoming unavoidable. Plan for consumption monitoring, model selection, and policy before limits surprise you.❓ Questions That Mattered When leaders see AI capabilities expand, how do they choose problems instead of chasing shiny possibilities?Do you treat AI literacy and vision as prerequisites, or as learning that happens after you start piloting?Where should a company look first for a beachhead of value across teams like revenue, ops, finance, and internal product?Will tokenomics and pricing changes push more companies toward hybrid models like hybrid seat plus usage, or on-prem and open source?🗣️ Notable Quotes “If you can do everything, you can do nothing.”“Stop spinning, choose one problem set, learn about AI in general and what it's possible and capable of doing, then choose that problem.”“Tokenomics part is going to become part of your governance.”“You’re going to pay for the tokens that we consume.”🔗 Links & Resources Listen To Other Episodes Co-Hosted With JustinRead the referenced Article

    201: "Vision First Or Tools First: The Hidden Step Before Any AI Implementation" ft. Justin Coats

  8. Jul 20

    200: "Need Vs Want: The Abundance Shift That Changes Everything" ft. Alli Murphy

    Erik and Alli Murphy unpack why “Operation Off Duty” caught so much attention, and how the simple act of asking for permission to rest creates real communication, less resentment, and more alignment in everyday life. 🧭 Conversation Highlights Alli explains the reel’s resonance: a curiosity hook plus an honest moment about needing permission because self-permission feels harder.Erik reframes the concept as giving people a vehicle to say what they actually want in relationships, including the quiet desire to do nothing sometimes.They connect “want vs. need” and the value of taking a step back to ask what you really want right now, not just what you think you should need.Alli shares a practical way to run the play: declare it, share it, set the timeline, and make the goal doing nothing for the specified window.💡 Key Takeaways People often need permission to rest, not because they are unwilling, but because they feel obligated to justify it.The value of Operation Off Duty is that it turns an unspoken desire into something you can communicate without blame.Want is an observation and an opportunity, while need can be a scarcity filter that narrows what feels possible.A simple playbook works: tell your household, clarify duration, and explicitly define what “off duty” means.❓ Questions That Mattered Why did Operation Off Duty land so hard with people: permission, curiosity, or the goofiness?How do couples actually surface what they want in the moment, especially when “we should be together” gets in the way?Am I asking for what I need, or am I avoiding what I want because I think I’m not supposed to want it?What’s the first step for someone who wants to try it: how do you roll it out with the people who matter?🗣️ Notable Quotes “We have permission to do these things, but it was me sharing the honest story about how I would walk around and be like, ‘I want permission from my husband so that I don't have to give permission to’“It almost gives you permission to have permission. That’s very meta.”“The goal all of a sudden is to do nothing… and that made it more palatable.”“Hey, TJ, I just learned about this ridiculous idea… I wanna have an operation off duty.”🔗 Links & Resources Listen To Other Episodes Co-Hosted With AlliCheck out Alli's Skool Community

    200: "Need Vs Want: The Abundance Shift That Changes Everything" ft. Alli Murphy
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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
    205
  • Rating
    Explicit
  • Copyright
    © 2026 I Have Some Questions...
  • Show Website
    I Have Some Questions...