000: Welcome To “I Have Some Questions…” I Have Some Questions... podcast

#MBA #Careers #Business #Podcasting Education #Self-Improvement #Erik Berglund

30:23

Tiffany Yu is the CEO & Founder of Diversability, an award-winning social enterprise to elevate disability pride; the Founder of the Awesome Foundation Disability Chapter, a monthly micro-grant that has awarded $92.5k to 93 disability projects in 11 countries; and the author of The Anti-Ableist Manifesto: Smashing Stereotypes, Forging Change, and Building a Disability-Inclusive World. As a person with visible and invisible disabilities stemming from a car crash, Tiffany has built a career on disability solidarity. Now that she has found success, she works to expand a network of people with disabilities and their allies to decrease stigmas around disability and create opportunities for disabled people in America. Episode Chapters 0:00 Intro 1:26 When do we choose to share our disability stories? 4:12 Jay’s disability story 8:35 Visible and invisible disabilities 13:10 What does an ally to the disability community look like? 16:34 NoBodyIsDisposable and 14(c) 21:26 How does Tiffany’s investment banking background shape her advocacy? 27:47 Goodbye and outro For video episodes, watch on www.youtube.com/@therudermanfamilyfoundation Stay in touch: X: @JayRuderman | @RudermanFdn LinkedIn: Jay Ruderman | Ruderman Family Foundation Instagram: All About Change Podcast | Ruderman Family Foundation To learn more about the podcast, visit https://allaboutchangepodcast.com/…

I Have Some Questions... «
000: Welcome to “I Have Some Questions…”

about a year ago 5:49

MP3•Episode home

🎙️ Episode Snapshot

In this launch episode of I Have Some Questions…, Erik Berglund sets the stage for a podcast built on one radical belief: that great leadership begins not with answers, but with better questions. He shares the personal journey that led him to this insight, the mission behind the show, and what listeners can expect from future episodes—interviews, solo deep dives, and a whole lot of leadership exploration.

❓ The Big Question

What if asking better questions is the most powerful leadership skill no one ever taught us?

💡 Key Takeaways

Curiosity, not charisma, is the underrated cornerstone of great leadership.
Most pivotal leadership moments begin with a powerful question—not a polished answer.
Many essential leadership skills (like balancing empathy with accountability) aren’t taught, but they can be explored through inquiry.
Lead with Questions will blend interviews with solo explorations to uncover the “why” behind powerful leadership decisions.

🧠 Concepts, Curves, and Frameworks

Language of Leadership: A business Erik founded to help leaders refine what they say and how they say it.
Speechcraft: A tool using AI roleplay to enhance soft skills like leadership and difficult conversations.
The Unspoken Curriculum: The leadership lessons no one teaches—like how to unlock others’ potential or what “accountability” really means.

🔁 Real-Life Reflections

Erik’s leadership journey began at 18, managing a house painting crew, which planted the seeds of his curiosity-driven approach.
He later scaled to leading sales teams and eventually left corporate to coach and build leadership-focused ventures.
Key turning points often came from internal questions, not external accolades.

🧰 Put This Into Practice

Reflect on your own leadership journey: What moments were shaped by powerful questions?
Ask yourself: What have I been told to do as a leader that no one actually taught me how to do?
Identify one question you’d love to hear answered on the podcast and send it Erik’s way.
Challenge your team with a curiosity-driven prompt this week—see what emerges.

🗣️ Favorite Quotes

“I think curiosity and good questions is the core skill for leadership.”“I can’t guarantee we’ll always get to the bottom of an answer. But ideally, we’ll build better frameworks—and better questions.”

19 episodes

000: Welcome to “I Have Some Questions…”

I Have Some Questions...

published about a year ago

MP3•Episode home

🎙️ Episode Snapshot

❓ The Big Question

What if asking better questions is the most powerful leadership skill no one ever taught us?

💡 Key Takeaways

Curiosity, not charisma, is the underrated cornerstone of great leadership.
Most pivotal leadership moments begin with a powerful question—not a polished answer.
Many essential leadership skills (like balancing empathy with accountability) aren’t taught, but they can be explored through inquiry.
Lead with Questions will blend interviews with solo explorations to uncover the “why” behind powerful leadership decisions.

🧠 Concepts, Curves, and Frameworks

Language of Leadership: A business Erik founded to help leaders refine what they say and how they say it.
Speechcraft: A tool using AI roleplay to enhance soft skills like leadership and difficult conversations.
The Unspoken Curriculum: The leadership lessons no one teaches—like how to unlock others’ potential or what “accountability” really means.

🔁 Real-Life Reflections

Erik’s leadership journey began at 18, managing a house painting crew, which planted the seeds of his curiosity-driven approach.
He later scaled to leading sales teams and eventually left corporate to coach and build leadership-focused ventures.
Key turning points often came from internal questions, not external accolades.

🧰 Put This Into Practice

Reflect on your own leadership journey: What moments were shaped by powerful questions?
Ask yourself: What have I been told to do as a leader that no one actually taught me how to do?
Identify one question you’d love to hear answered on the podcast and send it Erik’s way.
Challenge your team with a curiosity-driven prompt this week—see what emerges.

🗣️ Favorite Quotes

“I think curiosity and good questions is the core skill for leadership.”“I can’t guarantee we’ll always get to the bottom of an answer. But ideally, we’ll build better frameworks—and better questions.”

19 episodes

#MBA #Careers #Business #Podcasting Education #Self-Improvement #Erik Berglund

All episodes

I Have Some Questions...

1
020: “Can You Build a Culture Around Systems?” ft. Justin Coats 1:35:25

1 day ago1:35:25

1:35:25

🎙️ Episode Snapshot Erik sits down with AI implementer, systems thinker, and neesh.ai founder Justin Coats for a future-forward conversation that spans war zones to workflow. From wrenching helicopters in the Marines to designing AI frameworks for SMBs, Justin's journey is anything but linear — and that’s exactly why his perspective hits so hard. Together, they explore the human side of exponential tech, the slow pace of adoption, and what it really means to lead in a world that’s changing faster than we can comprehend. 👤 About the Guest Justin Coats is the founder of neesh.ai , a company helping individuals and organizations level up their AI literacy and integrate intelligent systems into their operations. A U.S. Marine veteran turned Amazon entrepreneur turned AI advocate, Justin’s credibility comes not just from what he knows — but from how he builds. He's hosted AI conferences, worked one-on-one with late adopters and early tech execs alike, and is committed to ushering humanity into the new era of AI-enabled work. 🧭 Conversation Highlights Justin’s path from military mechanic to entrepreneur to AI systems builder The “aha” moment when ChatGPT transformed an hour of brainstorming into a full marketing plan Why step 1–8 of most tasks should be handed to AI and why 9 & 10 belong to us The danger of confusing comfort with alignment and why this era is forcing people to reevaluate their lives AI as a leveler: why for the first time in history, tech might actually democratize opportunity What kids will grow up understanding that adults currently can’t fathom 💡 Key Takeaways AI is the great reset — everyone is starting at square one, and those who learn how to wield it early will set the pace for others. The future belongs to the generalist — people who can creatively think, spot opportunities, and wield tools. You don’t need to dream bigger, you need to start smaller — identifying annoying, overlooked problems can be a goldmine when paired with AI. The 80% trap is real — most human energy is spent on rote tasks; AI can unlock the time and space for higher-level thinking. We are the gap generation — caught between analog mindsets and AI-native futures, our job is to bridge the chaos into clarity. ❓ Questions That Mattered What’s actually happening under the hood of these “language models” and why does it matter? How long will humans remain “in the loop”? Is this tech a forcing function or just an opportunity most people will ignore? 🗣️ Notable Quotes “We’ve trained humans for decades to be robots. Now we’re shocked when real robots do it better.” — Justin Coats “AI isn’t taking over — it’s giving you a shot to actually think. Most of us haven’t done that in a long time.” — Justin Coats “Humans are slow. That’s not an insult — it’s just the truth. And that’s why we build tools.” — Justin Coats 🔗 Links & Resources neesh.ai – Justin's company Check out Justin’s LinkedIn for more info about his upcoming event: AI in the West…

I Have Some Questions...

1
018: “Can You Lead Without Knowing Where You’re Going?” (lessons from Brendan Burns) 10:09

7 days ago10:09

10:09

🧠 Erik’s Take This solo debrief is as much a mirror as it is a microphone. Erik reflects on his conversation with Brendan Burns—coach, hedge fund founder, and a pivotal influence in his own journey—and uses it to explore the uncomfortable but critical tension between external success and internal clarity . What happens when even the best in the game can’t quite articulate their mission? What does that say about the rest of us? 🎯 Top Insights from the Interview Even Experts Miss Their Own Blind Spots : Despite all of Brendan’s skills, templates, and success, the clarity of mission and fear-handling frameworks still felt elusive. That’s not a failure—it’s reality. Plumber with a Leaky Sink Syndrome : Just because you help others with mission, vision, and values doesn’t mean you’ve nailed your own. And that’s okay, but it’s worth naming. Company vs. Life Alignment : The need for clarity hits harder in business, because leadership demands communication. But in life, ambiguity often goes unnoticed until it doesn't. The “Life Fund” Concept Is More Than a Thought Experiment : Pairing wealth management with intentional personal development could redefine how high performers grow—and how coaching reaches them. Hindsight Strategy Is Still Strategy : Sometimes, we only realize how smart a move was after the fact. Brendan’s investor-coaching overlap might be just that. 🧩 The Personal Layer Erik doesn’t hold back here. He admits he hasn’t articulated a clear mission for his business, even as he coaches others through that very process. He opens up about his hesitancy to engage in a deep personal retreat, not out of fear of cost, but of disruption . And he shares how parenting, personal frameworks, and upcoming growth decisions are surfacing new questions. This is Erik, not just the coach or strategist, but the human navigating ambiguity in real time. 🧰 From Insight to Action Revisit Your Mission : Whether you’re a founder or solopreneur, if you haven’t done the work to articulate your mission and values, now is the time. Especially if you’re adding people soon. Name the Fear (Without Needing to Solve It Yet) : If there’s something you’re avoiding (a conversation, a coach, a retreat), naming it clearly is the first courageous act. Look Back for Origin Stories : What skills from your past—degrees, roles, hobbies—still shape how you think and lead today? There’s wisdom in the rearview mirror. Design Your Own “Life Fund” : Whether you’re wealthy or not, think about investing equally in your financial health and your personal growth. Success Doesn’t Answer the Big Questions : Achieving your goals won’t automatically clarify your purpose. Do that work on purpose . 🗣️ Notable Quotes “Some of the best people in the world don’t know how they do it—but they still do it well.” “In business, friction makes the need for mission more obvious. In life, we can coast without it.” “The genius moves we make in business? Sometimes we only see them in hindsight.” 🔗 Links & Resources Brian’s Coaching Website Listen to Brian’s Podcast Connect with Brian on Instagram…

I Have Some Questions...

1
017: “Is There a Difference Between Success and Satisfaction?” ft. Brendan Burns 56:16

9 days ago56:16

56:16

🎙️ Episode Snapshot Erik welcomes coach, podcaster, and hedge fund founder Brendan Burns —his former coach and the catalyst behind the creation of Language of Leadership . This isn’t just a reunion; it’s a deep dive into Brendan’s unconventional path from law school and hedge funds to transformational coaching and multi-business leadership. The conversation explores the questions that matter most when navigating career transitions, building purpose-driven businesses, and choosing alignment over achievement alone. 👤 About the Guest Brendan Burns is a multi-hyphenate success: hedge fund founder, transformational coach, Cornell-educated attorney, and former investment banker. Known for helping entrepreneurs build high-impact businesses from a place of deep alignment, Brendan’s unique blend of tactical business savvy and emotional intelligence makes him one of the most sought-after coaches for founders and coaches alike. Through his coaching, podcasting, and now hedge fund leadership, he’s helping leaders grow in wealth, impact, and self-awareness without losing themselves in the process. 🧭 Conversation Highlights From Wall Street to Coaching : Brendan's shift from hedge fund life to entrepreneurship was a personal awakening rooted in therapy, coaching, and self-discovery. The Question That Changed Everything : “What if it does work?” became Brendan’s guiding principle when starting over. Selling from Vision, Not Fear : Why money-only goals fall flat—and why mission-centered entrepreneurs create deeper impact and longer-lasting businesses. Coaching Wealthy Clients : Brendan’s hedge fund model doubles as a backdoor to personal transformation for investors, combining capital management with emotional and life growth. The ROI of Self-Investment : Erik and Brendan share vulnerable stories about early coaching experiences, what made the difference, and how perception is often the biggest block. 💡 Key Takeaways Mission Beats Metrics : Sustainable businesses come from alignment, not ego. Purpose is the foundation that drives everything else. You Can't Coach What You Haven’t Lived : Brendan’s emotional breakdown in the finance world gave him the empathy and perspective he now brings to his clients. The First Sale is to Yourself : Before you convince the world, you must believe your dream is possible . Brendan’s journey proves that starts with mentorship and mindset. Curate Your Circle : Oversharing your dream with unsupportive people can crush it. Find those who believe and build with them. ❓ Questions That Mattered “Why this path? What does coaching give you that finance couldn’t?” “How do you stay aligned as an entrepreneur when new opportunities keep showing up?” “What’s the role of fear in keeping founders stuck?” 🗣️ Notable Quotes “There’s no reason I should be alive—not addicted, not in pain. But coaching helped me get here. Now I help others do the same.” “Don’t just build a business. Build a mission.” “Some hedge funds manage wealth. We manage wealth and transform lives.” 🔗 Links & Resources Brian’s Coaching Website Listen to Brian’s Podcast Connect with Brian on Instagram…

I Have Some Questions...

1
015: “What Happens When You Finally Ask the Real Questions?” (lessons from Kyle Nelson & Eli Libby) 10:20

14 days ago10:20

10:20

🧠 Erik’s Take This reaction is more than a recap—it’s a confession. Erik shares his very real fear of solitude, of discovering he’s off course, and of what clarity might demand of him if he dares to seek it. It’s a vulnerable, reflective breakdown of the Kyle & Eli episode, and a deeper dive into why structured solitude might be the leadership development most of us are avoiding. The hardest part isn’t asking the questions, it’s what the answers will require of us. 🎯 Top Insights from the Interview Clarity Requires Commitment : Erik names what most people won’t: certainty obligates us . When you know what’s right, you can’t unknow it. And that’s terrifying. Solitude is the Shortcut to Alignment : ResetOS reframes solitude from scary to strategic. It’s all about intentional reflection. Conviction Is a Better Compass Than Momentum : When you’re already in motion, it’s hard to pause. But pausing might save you from racing in the wrong direction. We Overvalue Comfort and Undervalue Realignment : It’s easier to stay “kind of right” than to be forced into action by clarity. 🧩 The Personal Layer Erik doesn't hide here. He talks openly about why he's afraid to do a solo retreat—not because he can’t face himself, but because he might realize he has to make changes he’s not ready to make. He also opens up about his admiration for Kyle & Eli’s partnership: the depth of mutual respect, the shared vision, the decision to build with each other, not just next to each other. And in his signature self-coaching tone, he invites listeners to examine the questions they might be running from—not because they're silly or unoriginal, but because they're real. 🧰 From Insight to Action Here’s how Erik is thinking about applying the episode’s lessons: Schedule the Solo Time : Don’t wait for space— create it. Name the Fear : Articulate what you’re actually afraid of—action, not awareness, is often the culprit. Consider the Cost of Not Knowing : Wouldn’t you rather discover you’re on the wrong road early, before you’ve gone too far? Use What Ifs Strategically : Ask: “What if I had clarity?” instead of just “What if I’m wrong?” Don’t Disqualify Your Questions : Even the “unoriginal” ones matter deeply when they’re your questions. 🗣️ Notable Quotes “Certainty demands something of us. That’s why we fear it.” “I’d rather know I’m wrong than wish I had known.” “You’re not afraid of what you’ll see—you’re afraid of what you’ll have to do about it.” 🔗 Links & Resources 🌐 ResetOS.co – Take the Clarity Assessment, join the Reset newsletter, or explore solo retreat options 👤 Kyle Nelson on LinkedIn 👤 Eli Libby on LinkedIn…

I Have Some Questions...

1
014: “What Does It Take to Realign Your Life and Business?” ft. Kyle Nelson & Eli Libby 52:38

16 days ago52:38

52:38

🎙️ Episode Snapshot Erik sits down with long-time friends and co-founders Kyle Nelson and Eli Libby , the creators of ResetOS , a clarity operating system designed to help high performers realign their internal compass before life forces them to. This episode dives deep into the transformational power of structured solitude, explores how pain can become purpose, and reveals how friendship and reflection can build more than just businesses—they can build lives. 👤 About the Guests Kyle Nelson and Eli Libby are the co-founders of ResetOS , a personal clarity system built from their own stories of burnout, tragedy, and healing. Over 12 years of friendship and five businesses, they’ve seen success, suffered major losses, and built a unique process to help others find alignment through solo retreats. Their mission is to help people reconnect with who they are—and why they do what they do—before it’s too late. 🧭 Conversation Highlights From Collapse to Clarity : Kyle’s story of losing everything, from home to identity, and Eli’s rapid series of losses reveal the crucible that forged ResetOS. The Fear of Solitude : Why most people resist the very stillness that could change their life and how Kyle & Eli help them face it. Loneliness vs. Solitude : The program teaches how structured solitude can actually be the cure for chronic loneliness. Co-Founder Chemistry : How 12 years of friendship, deep assessments, and mutual respect shape their work and keep ego in check. 💡 Key Takeaways Fear Is the Gatekeeper to Growth : Most people resist solitude not because they fear being alone, but because of what they'll discover (and have to do with it). Your Answers Are Already Inside : The right structure and questions can help uncover what no coach or course can offer: internal clarity. Mature Misalignment Looks Like Success : Even people with the house, the job, the kids, and the money still wonder, “Why am I not fulfilled?” Partnership Requires Practice : The relationship between Kyle & Eli is a testament to what’s possible when founders prioritize mutual vision, honest questions, and emotional intelligence. ❓ Questions That Mattered “What happens if you don’t disconnect?” “Is this really the road I want to be on?” “What does fulfillment mean to you , not just to your industry?” “Can I be successful without being aligned?” “How do I lead my life without knowing what I believe?” 🗣️ Notable Quotes “Fear is just an excuse dressed up as logic. And it’s usually hiding a lie.” “You’re not afraid of the mirror—you’re afraid of what it’ll require once you see clearly.” “Solitude isn’t loneliness. It’s the space where you finally hear yourself.” “Most of us make life-changing decisions based on one dimension of ‘what if.’ What if we explored them all ?” “The answers aren’t out there. You just haven’t asked yourself the right questions yet.” 🔗 Links & Resources 🌐 ResetOS.co – Take the Clarity Assessment, join the Reset newsletter, or explore solo retreat options 👤 Kyle Nelson on LinkedIn 👤 Eli Libby on LinkedIn…

I Have Some Questions...

1
013: What If Motivation Isn’t the Problem? 28:38

18 days ago28:38

28:38

🎙️ Episode Snapshot In this solo episode, Erik takes a sledgehammer to one of the most overused and misunderstood leadership questions: “How do I motivate my people?” He breaks down why motivation isn’t your job, and how alignment is the real lever leaders should be pulling. From hiring to training, development to retention, Erik reframes every step of the employee journey through the lens of alignment and shares the practical conversations that make it possible. ❓ The Big Question What if the problem isn’t that your people lack motivation, but that your leadership lacks alignment? 💡 Key Takeaways You can’t motivate people. Motivation is internal. You can inspire, but inspiration fades fast. Alignment is the lever. Match what your people naturally want with what the business needs. Three alignment questions revolutionize interviews: What skills do you want to grow? What experiences do you want to live through? What responsibilities do you want to bear? Training fails when it lacks connection. Tie learning and feedback to what matters to the individual. Retention thrives on trust. The best way to keep your team is to understand their evolving motivations and speak directly to them. 🧠 Concepts, Curves, and Frameworks The Alignment Loop : Hire for it Train into it Develop through it Retain because of it Rules of Engagement : Questions to ask your team to understand how they operate, what drives them, and how to give feedback that actually lands. Misalignment ≠ failure : Acknowledging misalignment with honesty builds more trust than false positivity ever will. 🔁 Real-Life Reflections Erik shares the frustration he felt in early interviews hearing everyone say they wanted to be a manager until he changed the question set. He walks through powerful real examples of using alignment to shape feedback: reframing “you’re late” as a barrier to earning peer trust. Reflects on a personal turning point—realizing that trying to "motivate" people was exhausting and ineffective. Alignment made the job feel energizing again. 🧰 Put This Into Practice Update your interview flow : Start asking about skills, experiences, and responsibilities. Build alignment profiles : Know what each team member is actually trying to get out of work. Lead with why it matters to them when giving feedback, not just why it matters to you or the company. Have alignment check-ins : Especially for team members in year 2–5, when coasting and quiet quitting often sneak in. Be honest about misalignment : It’s okay to say “this task doesn’t align with your goals—but we still need to crush it.” 🗣️ Favorite Quotes “Inspiration expires. Alignment sustains.” “Most people work to live not live to work. Leadership is about making work worth it.” “Acknowledging misalignment can build more trust than pretending it doesn’t exist.”…

I Have Some Questions...

1
012: “Are You Settling for ‘Good Enough’ on Your Team?” (lessons from Alex Kudelka) 7:59

21 days ago7:59

7:59

🧠 Erik’s Take In this reflection, Erik breaks down his conversation with Alex Kudelka and extends the dialogue into a deeper meditation on one of the hardest (and most human) aspects of business: adding the right people . Whether it's a co-founder or a hire, getting the “who” right is make-or-break—and Erik’s vulnerable look at how pressure can lead to premature decisions is a powerful leadership check-in. This episode is a mirror for every founder and operator navigating the tension between urgency and fit. 🎯 Top Insights from the Interview The “New Color” Phenomenon : When you finally hire the right person, it’s like seeing a color you didn’t know existed. You can’t believe you ever settled for less. Mental Readiness > Job Description : Before writing the external job spec, leaders need to do the internal work, clarifying what they really want, and whether they’re willing to wait for it. Co-Founders vs. Hires : If you can name the deliverables, it’s a job. If it’s about mindset or relational complement, then it might be a co-founder. Rules of Engagement Matter : Whether it’s hiring or partnering, success often depends on how well you’ve defined the rules for when things get hard. The Universal Lesson : Whether in business, friendships, or life, being intentional about who you bring close is worth slowing down for. 🧩 The Personal Layer Erik opens up about his own past pressures in hiring—especially in sales roles—and how easy it is to “cave” when urgency outweighs clarity. His honesty about never having a co-founder is refreshing and prompts meaningful reflection about the risks and rewards of sharing the entrepreneurial load. This episode captures Erik’s growing conviction that the people decisions in business are the deepest, hardest, and most impactful. 🧰 From Insight to Action Erik suggests these real-life applications of the episode’s lessons: Pressure Test Yourself First : Ask, Am I willing to wait for the right person, or am I just trying to solve a short-term problem? Create Your Rules of Engagement : Whether hiring or partnering, define how you’ll handle conflict, misalignment, and tough calls. Revisit Your People Circle : Are you intentionally curating the right people in your business and in your personal life? Practice Better Questions : Vetting people well is a learnable skill. It starts with the right questions and active listening. 🗣️ Notable Quotes “Don’t write the job description until you’ve had the internal conversation with yourself.” “Am I willing to bear the pressure and not make the wrong hire? That’s the first question.” 🔗 Links & Resources Outdo Growth – Alex's company helping digital founders scale Alex Kudelka on LinkedIn – Follow for startup wisdom and leadership insight…

I Have Some Questions...

1
011: “Can You Scale a Business Without Diluting Your Magic?” ft. Alex Kudelka 1:01:49

23 days ago1:01:49

1:01:49

🎙️ Episode Snapshot Erik sits down with startup builder and Outdo Growth founder Alex Kudelka for a deeply honest and tactical conversation on what it really takes to build early-stage ventures. From co-founder dynamics to hiring pitfalls, from founder-led sales to the myths of scaling too early—this episode is a goldmine for founders navigating the messy middle of growth. The conversation balances strategic frameworks with hard-won lessons, all wrapped in Alex’s direct, insightful delivery. 👤 About the Guest Alex Kudelka is the founder of Outdo Growth , a startup builder and marketing services company powering the growth engines behind multiple digital entrepreneurs. A multi-time founder with exits and failures under his belt, Alex thrives in the zero-to-one stage, bringing an unmatched ability to build, test, pivot, and scale emerging ventures. He’s commercially minded, operationally savvy, and refreshingly transparent about what works (and what doesn’t). 🧭 Conversation Highlights Startup Love Language : Alex thrives in the pre-50M, pre-500 employee zone where curiosity, chaos, and creativity collide. Iteration with Paranoia : Testing quickly is vital, but over-pivoting kills momentum. The magic is in data and discipline. Co-Founders Are Like Spouses : Your partner must be battle-tested, supportive, and complementary. Otherwise, it won’t work. Founder-Led Sales Isn’t Optional : Until you've sold it yourself (a lot ), you don't have product-market fit. Hiring Fails and Frameworks : Outdo hired 50 people in 6 months. Only 18 remained. The lesson? Hire slow, ask better questions, and match energy to the actual role. 💡 Key Takeaways Love the Process, Not the Outcome : Founders who fall in love with testing and tinkering—not just the end goal—have more success (and fun). Healthy Debate Builds Stronger Startups : Co-founders must disagree well. Set “rules of engagement” for how to spar and commit. You Can’t Skip PMF : Selling something 10 times doesn’t mean it’s ready to scale. Rinse and repeat until signals are undeniable. Scope Creep Kills Service Businesses : Don’t be everything to everyone. Know your lane and stay ruthlessly focused. Responsibility is Revealing : In interviews, ask about the skills they want to build, the experiences they enjoy, and the responsibilities they crave. ❓ Questions That Mattered “How do you know when you’ve found true product-market fit?” “What do too few founders ask themselves before scaling?” “How should co-founders disagree, and how often should they?” “What do you listen for in a great interview answer?” 🗣️ Notable Quotes “Startup building is childlike creativity mixed with healthy paranoia.” “Most founders either over-pivot or scale too soon. Both can kill a business.” “Just because someone bought it once doesn’t mean you’ve nailed it.” 🔗 Links & Resources Outdo Growth – Alex's company helping digital founders scale Alex Kudelka on LinkedIn – Follow for startup wisdom and leadership insight…

I Have Some Questions...

1
010: Are You Ready to Lead an AI-Empowered Team? 39:53

25 days ago39:53

39:53

🎙️ Episode Snapshot In this solo episode, Erik unpacks the deeper leadership challenge that AI is creating—not just how to use the tools, but how to lead people who are using them. From data aggregation to automation to creation (and now even talent development), Erik lays out the evolving landscape and what it demands of leaders. He calls on listeners to ask better questions, adopt new hierarchies, and build resilient, QA-rich systems that keep humans accountable, creative, and connected. ❓ The Big Question How do you lead people who are armed with AI superpowers without losing clarity, accountability, or culture? 💡 Key Takeaways AI isn’t just a toolset—it’s a leadership test. The speed and scale of AI output challenges how leaders assess, guide, and trust their teams. The top three business uses of AI today—aggregation, automation, and creation—each carry serious leadership risks. The fourth emerging use of AI—talent development—is a game-changer and a hopeful counterpoint to fears of job loss. Leadership structures must evolve : Think more editors, fewer creators, more QA layers, and a rethink of how strategy is built. If you lose your talent pipeline, you lose your future leaders. AI could flatten that path unless you actively rebuild it. 🧠 Concepts, Curves, and Frameworks 3 Primary AI Functions : Assimilation & aggregation, automation, and creation. 4 Core Leadership Risks in an AI-augmented workplace: Data without understanding (false insights) Automation without purpose (efficiency ≠ effectiveness) Content without clarity (more ≠ better) Team structures that don’t evolve (hierarchy misalignment) QA/QC Layer : Not optional. Needed to catch hallucinations, false causality, and mission drift. The Strategic Pyramid Shift : From strategist → creator → editor… to strategist → agent → many editors . 🔁 Real-Life Reflections Erik shares a cautionary tale from a global manufacturing firm that measured the wrong data for 10 years—up and to the right… until it wasn’t. He reflects on his early experiences at Yahoo! and the long tail of technological adoption lag in the workforce. Compares historical tech transitions (Internet, smartphones) to what we’re seeing with AI now and how the leadership failure modes are eerily familiar. 🧰 Put This Into Practice Install a QA layer : Don’t trust AI outputs blindly—teach your team how to verify, synthesize, and question. Don’t automate confusion : Only automate what’s been clarified and vetted. Rethink your hierarchy : Especially in creative teams, consider where you need editors and where strategy needs to scale. Protect the development path : Find ways for people to learn the craft before they wield the super tools. Invest in AI-powered learning : Tools like Erik’s Speechcraft offer a powerful counterweight to skill erosion. 🗣️ Favorite Quotes “Just because your team can create more content doesn’t mean they’re creating the right content.” “The person using the tool might be wildly talented with AI and know absolutely nothing about your business.” “Two things can be true: AI might replace your job and help you rapidly re-skill into your next one.”…

I Have Some Questions...

1
009: “Are You Committed to the Process or Just the Result?” (lessons from Alex Boyd) 9:15

4 weeks ago9:15

9:15

🧠 Erik’s Take Coming off a powerful interview with Alex Boyd, Erik takes a moment to unpack the core themes that resonated most. This reflection is a masterclass in translating deep conversation into leadership action. What stood out was Alex’s but his clarity, vulnerability, and the fearless questions he asks himself. For Erik, this was a model of self-aware leadership worth emulating. 🎯 Top Insights from the Interview Self-Reflection without Shame : Alex models the power of examining yourself honestly, without layering guilt or judgment. That subtle but crucial distinction makes real growth possible. Don’t Over-Forecast : Inspired by Warren Buffett, Alex warns against getting too specific in future predictions. Planning matters, but adaptability wins. Commitment to Process : From daily financial check-ins to larger business rhythms, Alex’s success is built on intentional, repeatable systems. Ease ≠ Comfort : A powerful juxtaposition. Ease allows for flow and clarity; comfort often signals stagnation. Leaders should know the difference. Rethinking AI & Talent Development : The episode opened with a strong take on how AI will reshape organizational structures, leadership, and skill-building. Alex and Erik challenge us to design with intention. 🧩 The Personal Layer Erik doesn’t just observe Alex’s ideas—he tests them against his own life and leadership. His resistance to daily financial reviews? That’s real. But so is his recognition that routines—like workouts and journaling—are his equivalent “process.” He reflects on the tension between his desire to engineer outcomes and the reality of unpredictability. This episode became a mirror: how are you setting up your process? Are you confusing comfort with ease? 🧰 From Insight to Action Here’s how Erik suggests applying this episode to your own leadership: Audit Your Self-Talk : Are you layering judgment onto your reflections? Practice nonjudgmental awareness. Define Your “Process Stack” : Identify 3–5 processes that consistently help you perform at your best—personally and professionally. Revisit Forecasting : Be specific in effort, flexible in outcome. Don’t build brittle projections. Ease vs. Comfort Check : Where are you staying “comfortable” at the expense of real progress? Rethink Your Organization for AI : If you’re using AI, are your leadership systems adapting alongside your tools? 🗣️ Notable Quotes “Comfort might be a yellow flag. Ease, on the other hand, is a signal of systems working well.” “Don’t over-forecast. Be specific with effort, flexible with outcome.” “Be a kind leader, not a nice leader. That’s the difference between long-term care and short-term comfort.” 🔗 Links & Resources 💼 Connect with Alex Boyd on LinkedIn 📈 RevenueZen 🧠 Wildfront (coming soon)…

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008: “What’s the Secret to Sales That Don’t Suck?” ft. Alex Boyd 1:34:00

4 weeks ago1:34:00

1:34:00

🎙️ Episode Snapshot In this layered and laugh-filled conversation, Erik sits down with multi-time founder and investor Alex Boyd to talk about the collision of AI, leadership, and personal transformation. What begins as a conversation about technology and team-building morphs into a masterclass on intentional leadership, career evolution, and building with clarity. From building software tools in 20 minutes to learning when (and how) to fire someone, this episode is equal parts real talk and roadmap for the next-gen leader. 👤 About the Guest Alex Boyd is a founder, investor, and product strategist with deep roots in the startup and agency world. He’s the co-founder of: Wildfront – a micro PE firm focused on product-led growth and lean teams. Aware – a tool for managing relationship-based influence on LinkedIn. RevenueZen – an agency known for thought-leadership marketing. Alex blends technical curiosity with a philosopher’s mindset. With a background in philosophy and a long career in GTM strategy, Alex brings rigor, creativity, and deeply human insight to how products—and people—grow. 🧭 Conversation Highlights The three primary applications of AI—and why only one of them really excites Alex. Why AI isn’t killing creativity, but is redefining what counts as creative value. How to avoid “perception gaps” when AI creates the illusion of competence. Alex’s evolution from agency operator to product investor, and how he built a life of ease , not hustle. Why the most dangerous employees are the ones you know should go—but feel like you can’t fire yet. Erik and Alex unpack what it means to lead imperfectly but powerfully in the face of complexity. 💡 Key Takeaways AI requires a team re-architecture. The best companies are replacing typers with thinkers and editors, not just automating. Output isn’t everything. Quality still trumps quantity, and leaders must coach teams through false confidence from AI-generated work. You don’t need a five-year plan. You need a strong feedback loop and the courage to pivot when the data tells you to. Leadership is learning to tolerate storms. Holding discomfort while staying honest and curious is the real job. ❓Questions That Mattered What happens when creativity becomes editing, not ideation? Are we eliminating the training grounds that once produced great leaders? How do you build a business that supports your best thinking? 🗣️ Notable Quotes “The problem isn’t AI—it’s the perception gap it creates in people who think it did the job.”“We’re replacing thinkers with editors, and it changes everything about how you build a team.”“You don’t have to lie—but you don’t have to answer every question someone asks you, either.”“I’m not comfortable, but I have ease. That’s the life I want.”“I don’t plan 10 years out—but I do check my QuickBooks twice a day.” 🔗 Links & Resources 💼 Connect with Alex Boyd on LinkedIn 📈 RevenueZen 🧠 Wildfront (coming soon)…

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007: Are You Leading the Person or Fighting the Generation? 21:27

4 weeks ago21:27

21:27

🎙️ Episode Snapshot In this unfiltered, freewheeling solo riff, Erik tackles a controversial leadership question: How do you lead Millennials and Gen Z? Not from a place of judgment, but of lived experience. As a millennial himself, Erik offers a deep and human-centered take on why these generations behave differently at work, what they’re really optimizing for, and how leaders of all ages can unlock their performance by honoring their context, not criticizing it. This isn’t a generational rant, it’s a leadership reframe. ❓The Big Question What if Millennials and Gen Z aren’t lazy or entitled but simply responding rationally to a world that changed underneath them? 💡 Key Takeaways Generational distrust is earned. Millennials and Gen Z watched institutions crumble so loyalty isn’t assumed, it’s earned. Security no longer makes sense. These generations don’t chase pensions—they chase alignment, autonomy, and joy. They will give you their best but only if it aligns with what matters to them. True leadership means meeting people where they are, not where you wish they were. 🧠 Concepts, Curves, and Frameworks “The Ground is Not Stable” : The mental model shaping Millennial and Gen Z risk-taking. Corporate Loyalty is Dead : Because people watched it die. The North Star Test : If you don’t know what really motivates them, you can’t lead them. Surfer vs. Farmer Mindset : Boomers/X: Cultivate the land. Millennials/Z: Read the waves. 🔁 Real-Life Reflections Erik shares his own decision to walk away from a high-paying, low-effort corporate role to coach soccer and be present for his daughters. From music festivals to side hustles, Erik sees deep intentionality where others see distraction. His challenge: Stop asking “What’s wrong with them?” and start asking, “What matters to them?” 🧰 Put This Into Practice Ask This First : “What are you optimizing your life for right now?” Reframe Career Conversations : Lead with values and autonomy. Build Incentives Around Life Goals : Help your people earn what they care about , not just more salary. Stop Managing, Start Surfing : Build systems that flex with volatility because that’s what they expect. Ditch the Judgment Lens : Curiosity and context always outperform critique. 🗣️ Favorite Quotes “The problem isn’t that Gen Z is lazy. The problem is you don’t know what they’re optimizing for.” “If you know what lights someone up, you can align their fire with your mission. That’s leadership.” “Most of us aren’t disengaged. We’re just not going to kill ourselves for a system we don’t trust.”…

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006: What The F Is Accountability? 46:39

4 weeks ago46:39

46:39

🎙️ Episode Snapshot In this no-BS episode, Erik breaks down a word that everyone uses but few truly understand: accountability . Born from a career-defining moment when he couldn’t answer the question in a final interview, Erik shares the story that sparked his obsession with this misunderstood leadership cornerstone. He unpacks the real definition of accountability, why most leaders default to consequences instead of coaching, and how to build a culture where expectations are clear, feedback is proactive, and accountability is transformational. ❓The Big Question What does it actually mean to be accountable and how do you create that in yourself and others? 💡 Key Takeaways Accountability is not perfection. It’s a process of owning, communicating, diagnosing, and solving. True accountability happens before the deadline, not after it. Consequences ≠ accountability. You can have accountability without punishment. Holding someone accountable is a conversation , not a confrontation. To get accountability, you must first set expectations that include clarity, confirmation, and commitment . 🧠 Concepts, Curves, and Frameworks The 5 Steps of Accountability : Do what you said you'd do. If you can’t, proactively communicate before the deadline. Self-diagnose the failure—what broke down? Solve for the future —what will you do differently? Finish the job —take corrective action and communicate the next step. The Accountability Conversation : Ask questions that guide people through these 5 steps. Set-Up for Accountability : Clarity : What’s the goal? Confirmation : What’s your plan? Commitment : When will you start or finish? Consent : How can I hold you accountable? 🔁 Real-Life Reflections Erik revisits the gut-punch of a job interview that he didn’t get because he couldn’t clearly define how he held people accountable. He shares the evolution of his thinking: from vague expectations and blame to crystal-clear frameworks that create buy-in and growth. 🧰 Put This Into Practice Use the “When Did You Realize?” Question : This single prompt can transform reactive excuses into proactive awareness. Don’t just assign, ask for their plan. Make sure people tell you how they’ll meet your expectations. Make accountability normal. Use neutral, curious tone and open-ended questions to de-escalate defensiveness. Always ask : “How can I hold you accountable to that?” It changes everything. 🗣️ Favorite Quotes “Doing what you said you’d do is only step one. The real question is: What do you do when you don’t?” “We’ve confused accountability with consequences. They are not the same thing.” “Clarity is kindness, but confirmation is power. Get them to say it back to you.”…

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005: "What If You’re One Swing Away from Breakthrough?” ft. Brian Lofrumento 48:27

4 weeks ago48:27

48:27

🎙️ Episode Snapshot In this energizing and deeply reflective conversation, Erik sits down with serial entrepreneur, podcaster, and speaker Brian Lofrumento , whose 17-year journey has taken him from a soccer blog started in college to over 1100 podcast episodes and a newly launched nonprofit. They unpack what really drives entrepreneurs past the wantrepreneur stage, why "just ship it" is more than a Nike slogan, and how self-awareness and leadership begin with better questions. 👤 About the Guest Brian Lofrumento is the creator and host of The Wantrepreneur to Entrepreneur Podcast , author, and founder of multiple ventures including a new nonprofit dedicated to empowering change through entrepreneurship . He’s obsessed with helping people take imperfect action, embrace discomfort, and discover clarity through doing. With over 1100 podcast episodes under his belt, he brings a unique lens on leadership, growth, and how to create momentum that lasts. 🧭 Conversation Highlights 💡 Beyond Passion : Why passion is a great start, but not the whole story, and how curiosity and consistency are more predictive of success. 🧱 “Just Ship It” Culture : The overlooked importance of publishing over perfecting, and how feedback from the market refines your ideas. 🛠️ The Leadership Litmus Test : How understanding others’ (and your own) love languages creates trust, alignment, and long-term success. 💡 Key Takeaways Consistency outpaces brilliance : Most people quit too early; success often comes to those who simply stick around. Start small, but start : Even a half-baked blog post or idea can become a catalyst for exponential growth. Lead with reflection : Weekly rituals like solo coffee dates with deep questions can shape who you become. Legacy is a choice : Building something that outlasts you starts with what you prioritize today. ❓ Questions That Mattered “What patterns have you seen in the entrepreneurs who actually make it?” “What do you want your life to look like in a year?” “How do you differentiate between noise and true signal as an entrepreneur?” “What’s a powerful question you ask yourself consistently?” 🗣️ Notable Quotes “Do anything long enough and it won’t be the wrong thing.” “If you want someone to understand you, you have to speak in their love language.” “Entrepreneurs are just people who keep swinging the axe one more time.” 🔗 Links & Resources Follow Brian on LinkedIn Check out the Wantrepreneur to Entrepreneur Podcast Find out more about Brian's nonprofit, Through Entrepreneurship…

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004: How Do People Get Better at Things? 34:53

4 weeks ago34:53