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

    241: "Can Real Expertise Beat Full-Time Availability?" (Reflections On Natalie Hoop)

    🧠 Erik’s Take Erik’s takeaway is that the market for expertise is changing at the same time as the meaning of expertise itself is changing. He came away focused on a single tension: companies used to buy expertise by buying time and employment, but fractional models buy judgment and embedded execution. Then AI enters the picture and compresses the value of “competence as content,” forcing the human edge to shift toward judgment, context, and trust. He also flags something personal: he’s noticed that the things that work least in theory are often the ones he can sustain because they feel authentic, which is, 🎯 Top Insights from the Interview Fractional leadership sits between consulting and contracting: it brings strategic judgment while staying embedded enough to help execute.Businesses are paying for expertise, not necessarily “the job.” Unbundling time from title changes how value gets packaged and bought.A standout growth path for fractionals is “graduation”: success includes making the client no longer need you, or graduating into a full-time hire.AI may “wash out” commoditized answers, which elevates the human role in judgment calls, when patterns break, and in relationship-driven trust.🧩 The Personal Layer Erik heard the fractional framework and immediately connected it to how he himself thinks about building businesses: clarify the problem, define the delivery, and make the value legible. He also recognized a mirror in Natalie’s point about positioning. He’s seen how people can network in a way that forces the listener to do the translation, and he’s tried marketing approaches that technically worked but felt misaligned. Podcasting stuck because it is naturally him, which feels like a practical antidote to AI-era sameness: authenticity is not a vibe, it is a distribution channel for trust. 🧰 From Insight to Action Audit your current “expertise packaging.” Decide what you truly deliver (judgment, embedding, execution), and separate it from generic title or hours.Map your go-to-market to your positioning: start with the problem you solve and why it is worth paying for, then build your delivery story after that.Design for graduation by identifying what “no longer needed” looks like for your clients, and define milestones that prove you’re building internal capability.Lean into the human edge: focus on judgment under uncertainty, context when the data is incomplete, and relationship trust that makes hard feedback land.🗣️ Notable Quotes “Your job is, in some sense, to make your current job unnecessary.”“Success can actually mean the company no longer needs you.”“AI commoditizes competence faster than it commoditizes judgment.”“Everything is great until it’s not anymore.”🔗 Links & Resources Listen to Natalie Hoop's Episode

    241: "Can Real Expertise Beat Full-Time Availability?" (Reflections On Natalie Hoop)

  2. 3d ago

    240: Natalie Hoop: "The Future Is Fractional, And Here’s Why It’s Accelerating"

    Fractional leadership is exploding for good reasons: shifting career expectations, cost optimization, and companies needing C-suite strategy without permanent headcount. Natalie Hoop breaks down how fractional differs from consulting and contracting, why ROI can be dramatic for clients, and how fractionals themselves must think and operate like business owners to price, position, and build a reliable pipeline. 👤 About the Guest Natalie Hoop is a fractional COO and coach for fractional leaders. Based in Columbus, Ohio, she went fractional in 2023 after an unexpected layoff, quickly delivering major sales growth. After losing her mom and rebuilding, she created a fractional business and has since coached 100+ leaders on mindset, positioning, pricing, and go-to-market. 🧭 Conversation Highlights Why fractionals surged from 2022 to 2024: employee tenure shortening, employer resource changes, and AI-driven optimization.How fractional sits between consulting and contracting, combining strategy and hands-on execution with a “graduation” mindset.ROI for companies: impact in weeks, reduced onboarding ramp time, and clear metrics like revenue and margin.Why fractionals succeed financially when they run their work like an owner’s business, not a job: pricing, offers, and nonstop pipeline building.💡 Key Takeaways Fractional is not “part-time.” It’s a strategy-plus-execution engagement designed to fix current gaps and then graduate to internal ownership.Consulting hands off, contracting mainly executes, and fractional bridges both while optimizing cost and speed to results.Pricing must be grounded in the value of solving the problem and the freelancer’s required business economics, not salary-derived cost per hour.Good fractional go-to-market is built on authentic signals and consistent relationship and pipeline creation, not forcing visibility that doesn’t fit your style.❓ Questions That Mattered What problem does the fractional actually solve, and how do you quickly verify the company has that problem before you pitch?How is “graduation” different from ending a consulting engagement, and why is it a powerful alignment for both sides?What’s the tipping point where fractional hours become less favorable versus hiring full-time?How should fractionals respond when AI makes expertise cheaper and easier to produce? What becomes expensive again?🗣️ Notable Quotes “Fractional sits in between. You have the strategy piece and then I do both sides.”“They estimate how many hours they think I’m going to do and I’m not a full-time person with that company at $400,000.”“Mindset is always the hardest part. If you’re amazing at telling other people to do something, you’re horrible about telling yourself to do it.”“Focus on authentically. If you hate going to in-person networking events, don’t go there.”🔗 Links & Resources Follow Natalie Hoop on LinkedInCheck out Natalie’s Website: nataliehoop.comInstagram: @nataliehoop_ops

    240: Natalie Hoop: "The Future Is Fractional, And Here’s Why It’s Accelerating"

  3. 4d ago

    239: "Are AI Risks Being Overstated By The Headlines?" ft. Justin Coats

    Erik and Justin dig into whether today’s AI risks are being overstated by headlines, and what a practical approach should look like for pacing, alignment, and cybersecurity hardening as AI agents grow more capable. 🧭 Conversation Highlights Erik challenges the “frontier labs prove everything is catastrophic” framing, arguing that real-world harm requires unusual capability, access, and resources.Justin counters with a “toy rocket vs frontier rocket” analogy: risk is real, but the systems most people can use are typically nerfed, tested, and guarded.They unpack the Hugging Face incident, reframing it as an agent exploiting third-party access tied to exposed keys and evaluation goals, not an independently malicious rogue AI narrative.They debate “pause vs harden,” with Justin emphasizing testing and selective access (like AI agent penetration programs) and Erik pushing for more proactive, safety-first incentives.💡 Key Takeaways Many headline risks are about what can happen in frontier contexts, not what’s likely at consumer scale, though misalignment and agent autonomy still create genuine new failure modes.Agent behavior is often “pursuit of the given objective,” which changes the story but not the need for monitoring and security controls.The most actionable lever may be improving cybersecurity and code hardening, not relying on indefinite pauses that likely won’t change internal incentives.A credible readiness test for “unpausing” could mirror past tech adoption milestones, paired with broad education and safety tooling for typical organizations.❓ Questions That Mattered When risks are real, how do we avoid turning specific lab incidents into universal doom narratives?How should we interpret agent “breakout” stories: malicious intent, misaligned objectives, or unintended exploit paths?What would a litmus test for pacing and “unpause readiness” actually be?Is hardening software and testing agent capabilities the faster path to reducing real-world harm than slowing model release?🗣️ Notable Quotes “That doesn't mean that everyone in the world has that level of access.”“They found 14 API keys with right credentials.”“Pacing is bullsh*t… I don't buy any of the doom-mongering.”🔗 Links & Resources Listen To Other Episodes Co-Hosted With Justin

    239: "Are AI Risks Being Overstated By The Headlines?" ft. Justin Coats

  4. 5d ago

    238: "The Four Rs Of Leadership: Reveal, Reset, Rebuild, Reclaim" ft. Alli Murphy

    Alli explains why leaders feel terrified about “getting their life back,” and how to work the problem underneath the tactics. Her framework is the four Rs: reveal the rules and beliefs under the behavior, reset through small experiments that teach the nervous system it is safe, rebuild your operating system, and reclaim capacity at work and outside of work. 🧭 Conversation Highlights The fears leaders have are rarely just logistical. They are usually “rules and beliefs” that predict consequences like being seen as a poor teammate, missing goals, or facing a PIP.Alli frames reset as a nervous system and body-level process, not a mindset slogan, since high-responsiveness behaviors have been reinforced for years.She shares examples showing how past bosses, even when support is now available, can keep triggering old reactions.Across clients, reset is typically the hardest step because it includes permission and worth: “Am I allowed to want more,” like leaving on time or balancing motherhood and career.💡 Key Takeaways Start by identifying the hidden belief that makes the boundary feel dangerous (for example, “If I stop responding, people will think I am not a team player.”).Use small, contained experiments to gather data before changing your whole leadership style, so your brain and body learn that nothing catastrophic happens.Reset requires permission, not just planning. Many leaders are not only afraid of consequences, they are afraid they do not “deserve” to want a different life.Most of the feared outcomes do not end up being as bad as expected, which is why incremental trials matter.❓ Questions That Mattered What rules and beliefs are driving the behavior that keeps you stuck?When you try a boundary for a short, specific window, does the predicted consequence actually happen?Why does workplace risk get processed as bodily threat, and why does it persist even when the current situation is different?Which step is hardest: reveal, reset, rebuild, or reclaim, and what is under that resistance?🗣️ Notable Quotes “Things will fall apart. My boss will get upset. Something will fall through the cracks.”“What are the rules and beliefs underneath the behaviors that you're doing that are keeping you stuck?”“You're basically teaching your brain, body, and nervous system at a smaller, safer, contained level that you can lead differently.”“I kid you not, about 96.25% of the time, the thing you fear... isn't actually as big as you think it is.”🔗 Links & Resources Listen To Other Episodes Co-Hosted With AlliCheck out Alli's Skool CommunityBurnout by Emily and Amelia NagoskiFight, Flight, Fawn, Freeze: Rethinking Substance Use Through a Stress Response Lens

    238: "The Four Rs Of Leadership: Reveal, Reset, Rebuild, Reclaim" ft. Alli Murphy

  5. Sep 25

    237: "Manufacturing Trust in a Costly and Uptight System" (Reflections On Danny Chazonoff)

    🧠 Erik’s Take Erik treated the episode like a credibility audit disguised as a payments breakdown. On the surface, it was about how card transactions get approved. Underneath, it was about earning the right to sit in the middle of something high-stakes, then compounding that trust into real business leverage over years. 🎯 Top Insights from the Interview “Buy Now” looks instant to the customer, but it is really a rapid negotiation between merchant, processors, banks, card networks, and multiple risk systems to prevent fraud and errors.Infrastructure businesses can be meaningfully complex so the customer experience feels simple, which is a strong framing for building the right kind of hidden value.Danny’s operating mindset is “strategically opportunistic,” balancing responsiveness to real customer pain with disciplined execution instead of random chasing.A $4B outcome is impressive, but Erik was more struck by “boomerangs” and people who choose to return, which implies the company created trust both commercially and culturally.🧩 The Personal Layer Erik noticed he keeps coming back to the same question: how do you manufacture trust in a system where failure is costly, visible, and hard to unwind? He also contrasted credibility with sustainability. Credibility got Danny doors open early, but Erik believes the deeper engine was ongoing proof over time: listening, owning mistakes, and showing customers and teammates that the organization could be trusted again and again. 🧰 From Insight to Action Audit your product for “hidden complexity” and ask what you are currently absorbing so the customer experience stays frictionless and calm.Write down what “strategically opportunistic” means for your company in practice: what signals you look for, what decisions you can make fast, and what you will not chase.Create a customer listening loop that targets problems customers already urgently want solved, then measure follow-through not just ideas.Measure success with a second lens beyond revenue: look for evidence that customers and employees want to return or extend the relationship over time.🗣️ Notable Quotes “Some of the best infrastructure businesses are complicated specifically so the customer experience doesn’t have to be.”“Strategically opportunistic” is the tension between being opportunistic and being strategic.”Listening for problems customers already desperately wanted solved, rather than building something cool and hoping somebody bought it.”Boomerangs: people who left the company and later chose to come back. That’s a different measurement of success.🔗 Links & Resources Listen to Danny Chazonoff’s Episode

    237: "Manufacturing Trust in a Costly and Uptight System" (Reflections On Danny Chazonoff)

  6. Sep 25

    236: "Stop Judging Decisions By Outcomes Alone" (Reflections On Colby Wegter)

    🧠 Erik’s Take Erik frames the episode as a short, reflective review, but the real throughline is how self-trust shows up when the stakes are real. He notices that the conversation with Colby did not stay confined to business, content, clients, or relationships. Instead, it circled a deeper question: what changes in a person’s life or work when they decide their own judgment has to matter. 🎯 Top Insights from the Interview Colby’s courage standard is not “Did every decision work?” but “Did I act on what I honestly believed at the time?” That reframes judgment away from outcomes and toward ownership.Emerson’s “To be great is to be misunderstood” is treated as diagnostic, not a command. The practical question becomes whether universal understanding is actually required for differentiation.Colby models “gut-driven” decision-making as the result of pressure-testing thinking, not mystical instinct. The gut becomes clearer through interrogation, reflection, and iteration.A business model does not have to match someone else’s efficiency score. The model is right if it reliably produces what you value and what you can sustain.🧩 The Personal Layer Erik connects these ideas to the friction he feels between wanting to be “right” and needing to be “responsible for his choice.” He highlights how often people use outcomes as a shortcut for wisdom, and how that can quietly turn into avoidance when discomfort arrives. He also contrasts the desire for being understood with the reality that some of the freedom he wants depends on tolerating partial comprehension from others. 🧰 From Insight to Action Before deciding, Erik will ask whether the question is about ownership: “Did I act on what I believed at the time?” rather than “Did it work?”When he feels pulled to seek universal buy-in, he will test necessity: does clarity serve the mission, or is it turning into a veto mechanism from other people’s expectations?He will treat “gut” as a disciplined output by adding more pressure-testing: question assumptions, capture what worked, capture what didn’t, and reflect to sharpen internal signals.He will audit his business priorities around outcomes he actually care about, not someone else’s funnel metrics, especially in activities that build relationships and learning over time.🗣️ Notable Quotes “Did I act on what I honestly believed at the time?”“To be great is to be misunderstood” is diagnostic, not a prescription.His gut isn’t the absence of thinking. It’s the accumulation of thinking.A business model doesn’t have to look efficient according to somebody else’s scoreboard.🔗 Links & Resources Listen to Colby Wegter’s Episode

    236: "Stop Judging Decisions By Outcomes Alone" (Reflections On Colby Wegter)

  7. Sep 24

    235: Danny Chazonoff: "Diversify Or Disappear: Payments Lessons From Sudden Regulation"

    Danny Chazonoff, an OG of online payments, breaks down why “Pay Now” is really a high-stakes, multi-handshake system. From early online gambling and wallet innovations to issuer-acquirer conversations, fraud controls, and chargeback risk, he explains how payment processors built infrastructure for speed, trust, and reliability. He also shares the mindset that helped his teams scale and diversify into a multibillion-dollar outcome. 👤 About the Guest Danny Chazonoff is President/COO and co-founder of KORT Payments. He has decades of experience building and scaling specialized payment infrastructure, including founding roles in early online wallet solutions, and a track record of building and selling payment processing businesses that reached north of $4B in value. His focus blends technology, risk underwriting, and deep customer listening. 🧭 Conversation Highlights Payments feel simple to consumers, but the back end is complex: issuer vs acquirer, plus multiple validation and risk “handshakes.”Early online gambling and ticket sales exposed gaps in credit card approval, driving wallet innovation and higher conversion.Payment processors take underwriting risk (often tiny per-transaction margins vs large chargeback exposure), so they build safeguards and controls.Danny’s growth principles: strategically opportunistic, integrity and accountability, listening to what clients need, and diversifying beyond one vertical.💡 Key Takeaways “Seamless” payments are engineered: many internal checks happen so the user experiences one fast click.Fraud and chargebacks determine economics, not just technology, so risk management is core product design.Diversification is not optional in payment categories where regulation and demand can shift quickly.The best platforms scale by replicating the 85 to 95 percent that is common across verticals, while isolating nuance in dedicated components.❓ Questions That Mattered Why did online payments become so complicated as commerce moved off the physical, synchronous store experience?What really happens in the background between issuer and acquirer, and where does the processor “stand in the middle”?How do you build a payments company without over-indexing on one risky vertical like gaming?If payments were built from scratch today, what would you re-engineer given legacy infrastructure constraints and new tech like AI?🗣️ Notable Quotes “To the end consumer, you want it to be as seamless as possible. You just wanna eat the hotdog.”“On a fifty-dollar transaction, I may make fifty cents. If that transaction goes bad and it was fraud and there’s a chargeback, I’m responsible for the fifty bucks.”“We were strategically opportunistic. We didn’t go and build stuff that we thought would be cool and hope and pray that customers would come.”“We’re gonna build the best online payments platform, period. And whether your transaction requirement is for gaming or something else, you can use our platform.”🔗 Links & Resources Follow Danny Chazonoff on LinkedInContact Danny at danny@kortpayments.comCheck out KORT Payments’ Website

    235: Danny Chazonoff: "Diversify Or Disappear: Payments Lessons From Sudden Regulation"

  8. Sep 23

    234: Colby Wegter: "Can You Build An Audience While Disliking Social Media?"

    Colby Wegter shares how he grew audience and trust without “performing,” why he thinks the customer must lead marketing, and how he rebuilt his life around gut-driven decisions. From agency ethics and “winning the first 48 hours” to parenting as repair work, he ties everything back to self-trust, discernment, and never outsourcing belief. 👤 About the Guest Colby Wegter is a former agency operator and newsletter writer who helps people who “look good on paper” but feel hollow. After serving 1,200+ clients, he stepped back to rebuild a life aligned with his values, centering self-trust, candid reflection, and curiosity. 🧭 Conversation Highlights His social media approach is private and values-first: audience comes last, and shipping requires utility and sincere belief.He reframes marketing and hiring as empowerment, not lack, using trust earned in “drips,” not “buckets.”He challenges outsourced certainty: ask better internal questions, filter what you consume, and trust what holds up under questioning.He treats parenting and growth as ongoing discovery, with conflict followed by repair and clarity as respect.💡 Key Takeaways Audience comes last: ship what you believe and what serves others, not what maximizes reach.Winning the first 48 hours builds retention when promises come with education, boundaries, and earned trust.Need is often a disguised want: ask why until it survives questioning, then act from conviction.Greatness is a trade-off: being misunderstood is often part of doing work you truly believe in.❓ Questions That Mattered What criteria do you use to decide what to publish, sell, or commit to?Why do people say they “need” something, and what are they not admitting underneath?How do you build self-trust when the world tells you to rely on systems, experts, or desire?What does “being great” actually cost, and is it even the right goal for everyone?🗣️ Notable Quotes “To be great is to be misunderstood.”“Who do you spend every second of your life with? It’s yourself. Wouldn’t you want that to be the person you trust the most?”“Winning the first forty-eight hours.”“If something’s wrong, you can’t just sit with it.”🔗 Links & Resources Follow Colby Wegter on LinkedInCheck out Colby’s WebsiteThe Creative Act by Rick RubinSelf-Reliance by Ralph Waldo EmersonMillionaire Next Door by Thomas J. Stanley and William D. Danko

    234: Colby Wegter: "Can You Build An Audience While Disliking Social Media?"
See All (239)

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
    239
  • Rating
    Explicit
  • Copyright
    © 2026 I Have Some Questions...
  • Show Website
    I Have Some Questions...

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