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

I Have Some Questions...

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

33:42

ChatGPT Agent is here! ↳ What the heck is it? ↳ How does it work? ↳ What do you need to know? Glad you asked, shorties. Join us for the answers. Square keeps up so you don't have to slow down. Get everything you need to run and grow your business—without any long-term commitments. And why wait? Right now, you can get up to $200 off Square hardware at square.com/go/jordan. Run your business smarter with Square. Get started today. Newsletter: Sign up for our free daily newsletter More on this Episode: Episode Page Join the discussion: Thoughts on this? Join the convo and connect with other AI leaders on LinkedIn. Upcoming Episodes: Check out the upcoming Everyday AI Livestream lineup Website: YourEverydayAI.com Email The Show: info@youreverydayai.com Connect with Jordan on LinkedIn Topics Covered in This Episode: ChatGPT Agent Mode Overview & Naming Live ChatGPT Agent Demo Walkthrough ChatGPT Agent Mode Availability & Pricing Operator vs. Deep Research Capabilities Explained ChatGPT Agent Virtual Computer Functions Spreadsheet and PowerPoint Generation in ChatGPT Mini RAG-Ready Agents with Data Connectors ChatGPT Agent Security and Biological Risk Classification Timestamps: 00:00 "Introducing ChatGPT Agent" 03:41 Potential Delay for Paid Plan Rollout 09:24 "Chat GPT Agent: New Tools Overview" 12:44 OpenAI-Microsoft Tensions Over Software Overlap 16:42 "ChatGPT's New RAG Feature Unveiled" 21:55 AI Agent with Weapon Risk 23:31 Agent Models: Boon or Bane? 29:05 "Agent Mode: Seamless Editing Integration" Keywords: ChatGPT Agent, Agent Mode, OpenAI, virtual computer, Agentic skills, Operator, Deep Research, browsing websites, web research, synthesizing information, Microsoft competitor, PowerPoint creation, Excel spreadsheet creation, terminal access, public API integration, connectors, data analysis, image generation, multi-agent environments, retrieval augmented generation, mini RAG, AI operating system, human-in-the-loop, security concerns, biology classifier, biological weapons classification, chemical weapons classification, O3 model, Google Gemini 2.5 Pro, agentic models, AI workflows, editable slide deck, Microsoft Office alternative, AI-powered presentations, spreadsheet automation, cloud-based agents, AI task automation, calendar integration, Gmail connector, Google Drive connector, Outlook connector, team collaboratio Send Everyday AI and Jordan a text message. (We can't reply back unless you leave contact info) Try Gemini 2.5 Flash! Sign up at AIStudio.google.com to get started. Try Gemini 2.5 Flash! Sign up at AIStudio.google.com to get started. Try Gemini 2.5 Flash! Sign up at AIStudio.google.com to get started.…

about a year ago 1:34:00

MP3•Episode home

🎙️ 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

23 episodes

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

I Have Some Questions...

published about a year ago

MP3•Episode home

🎙️ Episode Snapshot

👤 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.

🧭 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

23 episodes

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

All episodes

I Have Some Questions...

1
024: “Can You Charge More, And Sell More?” (lessons from Amanda Bedell) 5:51

5 days ago5:51

5:51

In this reflective follow-up to his interview with Amanda Bedell, Erik gets honest about the uncomfortable truths business owners face when it comes to profit. Most of us think we’re “doing okay” because revenue is coming in—but Amanda forces a deeper look. What stuck with Erik most wasn’t just Amanda’s strategic brilliance—it was how she translated financial complexity into real leadership decisions. She didn’t just talk P&Ls or pricing formulas. She talked about leadership responsibility, team clarity, and what it really takes to build something that lasts. 🎯 Top Insights from the Interview Profit isn’t passive—it’s a leadership choice. Amanda reframes profitability from a reporting outcome into a strategic driver, deeply embedded in your decisions. Most businesses are built on broken math. Pricing errors often happen because owners don’t fully calculate true unit economics—including overhead. You can’t outsource clarity. Bookkeepers, CPAs, and accountants are helpful—but they rarely help you lead a profitable business. Marketing changes the math. Your pricing isn’t just constrained by your costs and competitors—it can be elevated by how you position what you offer. Execution must go beyond strategy. Erik points out the crucial missing link: How do you lead your people to deliver on premium positioning? 🧩 The Personal Layer Erik shares a behind-the-scenes window into how Amanda’s workshop challenged and shifted his own assumptions around pricing. He opens up about his own frustrations with the esoteric language of profit from financial professionals—and contrasts that with Amanda’s refreshingly direct, actionable style. One standout reflection? The story of KFC’s pricing experiment: when they raised prices instead of lowering them, they sold more—not because of the product, but because of how pricing signaled value. That single story sparked a bigger idea about what it really means to lead with intention around price—and what most of us miss by pricing to fit in. 🧰 From Insight to Action Audit your pricing story. Not just the math—but how it connects to your marketing, your team’s ability to explain it, and the customer’s experience of it. Use price as a positioning tool. Where are you playing small because you’ve only considered the market’s ceiling—not your offering’s potential? Bring your team into the strategy. Great ideas in the office don’t matter if your frontline can’t deliver the promise (red carpet → red flags without clarity). Reflect on pricing as leadership. Erik challenges listeners to consider: Am I leading through my numbers—or hiding behind them? 🗣️ Notable Quotes “It’s one thing to build a red carpet offer. It’s another to get your team to roll it out.” “Marketing isn’t just about acquiring customers—it’s about justifying your price.” “You’re either building a business or selling a very expensive job to yourself.” “Profit is a leadership language. Most of us were never taught how to speak it.”…

I Have Some Questions...

1
023: “What does it take to build a profitable business?” ft. Amanda Bedell 51:18

7 days ago51:18

51:18

In this episode, Erik sits down with Amanda Bedell, a no-BS profit strategist with a story that flips the script on what most entrepreneurs think running a “successful” business looks like. Amanda unpacks the painful lessons from building a $2M+ bakery—with zero profit—and how that failure catalyzed her mission to help founders build profitable, sellable businesses. The conversation gets tactical and emotional, strategic and human—offering a masterclass in real business truth-telling. 👤 About the Guest Amanda Bedell is a profit coach and strategic advisor to entrepreneurs. After building and selling a multi-million-dollar bakery that lacked profit, Amanda made it her mission to help founders escape the "broke but busy" trap. Through her advisory work, she helps companies dial in their pricing, understand their unit economics, and turn passion-driven ventures into cash-positive, strategically-sound businesses. 🧭 Conversation Highlights The distinction between profit theory and profit practice —and why both matter. Why most business owners get pricing wrong—and how to fix it. The tactical tools Amanda uses to calculate pricing that actually covers overhead. The difference between markup and margin—and how misunderstanding this sinks businesses. The human side of profit: how shame, emotion, and identity tie into your P&L. Why strategic marketing isn't “fluff”—it’s core to profit design. 💡 Key Takeaways Profit isn’t automatic—it's designed. Most entrepreneurs think selling equals success, but Amanda reveals how easy it is to run a multi-million-dollar business into the ground without strategic pricing. If your unit economics are broken, you don’t have a business. It doesn’t matter how passionate you are or how great your product is. Pricing is emotional and mathematical. If you avoid the math because it feels hard or makes you uncomfortable, your business will suffer. Branding influences price elasticity. Smart strategic positioning can increase what the market will bear—if you deliver on the promise. Hard truth is kindness. Amanda’s approach isn’t soft—but it’s the leadership most business owners actually need. ❓ Questions That Mattered How do you set prices when the market doesn’t “feel” ready for the numbers you need? What do you do when you realize your dream business is failing financially? How can branding and marketing reframe customer expectations—and profit margins? How do you navigate the emotional wreckage that comes from business failure? 🗣️ Notable Quotes “Every decision you make in your business is a profit decision.” “I had a $2 million business and couldn’t pay myself. That’s not success.” “Most bookkeepers aren't business owners. Their job is to report the past, not build your future.” “You don’t need to get to the right margin overnight—you need a strategy to get there.” 🔗 Links & Resources BCC Business Consulting: https://bccbusinessconsulting.com Follow Amanda on Instagram: @amandabedell…

I Have Some Questions...

1
022: What If Reviews Could Actually Make You a Better Leader? 19:18

9 days ago19:18

19:18

In this mid-year solo riff, Erik dismantles the anxiety and avoidance that plague performance reviews. Instead of dreading the annual ritual, Erik lays out a practical, human-first framework that transforms reviews into accountability-driving, career-shaping conversations. Whether you're leading five or fifty, this episode offers a process that helps your people grow and helps you lead with confidence, clarity, and calm. ❓The Big Question How do we turn performance reviews from a dreaded chore into a powerful tool for growth and accountability? 💡 Key Takeaways The real purpose of a review is to drive change , not just check boxes. Setting expectations upfront makes everything smoother—for both leader and team member. Self-assessment first : letting the employee go first reveals more than you'd expect. Share the benchmark criteria in advance. T ransparency builds trust and better conversations. Get commitments in writing and ask how your team wants to be held accountable. 🧠 Concepts, Curves, and Frameworks The Review Reframe : Shift the goal from evaluation to transformation. Ownership Sequence : Let them self-assess → you respond → they commit → you align on accountability. Expectation Anchoring : Outline what’s coming—timeline, process, structure—to reduce anxiety. Surprise-Free Zone : Reviews should document what’s already been said, not deliver shocks. The Follow-Through Gap : Without documentation and accountability requests, nothing sticks. 🔁 Real-Life Reflections Erik shares how he went from dreading reviews to blocking off two hours and loving the clarity it brought. He recalls coaching teams of 16 slippery sales reps and learning to build the review muscle to regain confidence. Points out the trap of leaders who “save it all” for the review, realizing ongoing feedback beats stockpiling. 🧰 Put This Into Practice Send your review framework early and let them self-score. Script your review intro to clarify purpose, structure, and expectations. In the review, let them speak first and build on their reflections. Ask: “ What are you going to do differently? ” and listen for specifics (who, what, when, where, how). Follow up : Have them email their commitments and tell you how to hold them accountable. 🗣️ Favorite Quotes “The whole goal is to drive change, reinforce what’s working, and align on what’s not.” “People are far more likely to change if they tell you what they’re going to do.” “Very little in a great review should be a surprise.” “Don’t skip the last step: ‘How do you want me to hold you accountable?’ That’s where the trust builds.” “If you only give yourself 15 minutes to write a review, you’re not doing your people, or yourself, justice.”…

I Have Some Questions...

1
021: “Will You Adapt Before You’re Forced To?” (lessons from Justin Coats) 8:25

12 days ago8:25

8:25

Coming off the conversation with Justin Coats, Erik reflects on what stood out most — not just in what was said, but in the tone of how it was said. Justin’s outlook on AI is refreshingly optimistic, and not in a techno-utopian way. His confidence stems from deep proximity to the tools, but also from the pattern recognition of someone who’s rebuilt himself multiple times. This reaction is Erik’s way of pulling that thread further: What if Justin’s not just right — what if he's early? And what if we’ve been dramatically overvaluing busywork while underestimating what we're actually capable of? 🎯 Top Insights from the Interview Disruption is already here. Industries like marketing are being gutted. Legal, sales, and creative are next. If you feel safe, it might just mean you're early. You’re probably doing less meaningful work than you think. Erik revisits his own sales leadership role and admits — most of his 50-hour weeks only contained ~10 hours of real value. The “race to the bottom” isn’t inevitable. Companies won’t all optimize for cost. Many will reinvest efficiency gains into higher-margin or more meaningful work — and that opens new lanes. This is an invitation to create. Whether you’re laid off or leveraged, the tools are there. This is a once-in-a-generation opportunity to rethink what you want to build. AI won't replace you — but it might replace your inertia. Those who embrace the tools early will create massive leverage. Those who wait for a forcing function may be too late. 🧩 The Personal Layer There’s a vulnerability in this episode — Erik names his fear. Not just as a professional, but as a father, husband, and friend. He acknowledges the real human cost of change and the worry for people he cares about. But he also offers a hard truth: maybe the stuff we’re clinging to wasn’t that meaningful in the first place. He also shares a deep resonance with Justin Coats’s view that humans are wildly capable — and that what we really need now isn’t more motivation, it’s better attention to what matters. 🧰 From Insight to Action Audit your week. How many hours are you doing real work? What could be handed off to AI or automated systems? Practice noticing problems. Get less numb. Pay attention to the inefficiencies in your world — those are potential business ideas. Try one tool. Whether it’s Replit, ChatGPT, or Claude — spend an hour creating something small. Not researching. Building. Stop waiting for permission. AI has leveled the playing field. If you have a bias for action, you’re ahead of 95% of people. Talk to your people. If you lead a team or have peers you care about, initiate this conversation. Don’t wait for the crisis to come. 🗣️ Notable Quotes “Justin’s optimism isn’t naive. It’s earned. He’s been through reinvention — he knows what’s on the other side.” — Erik Berglund “If you’re waiting for the forcing function, you’re probably already behind.” — Erik Berglund “The opportunity is wide open in front of you — and you’re still early.” — Erik Berglund 🔗 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
020: “Can You Build a Culture Around Systems?” ft. Justin Coats 1:35:25

14 days ago1:35:25

1:35:25

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

19 days ago10:09

10:09

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

21 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

26 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...

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

28 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…

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

30 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.”…

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

5 weeks 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…

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

5 weeks 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…

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

5 weeks 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.”…

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

6 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

6 weeks ago1:34:00