Podcast
the Learn-It-All™ podcast
Hosted by Damon Lembi · EN
The Learn-It-All™ podcast is built on the conviction that the leaders worth following aren't the ones with all the answers. They're the ones who never stop learning. If you've chosen growth over coasting, and curiosity over the comfort of being the smartest person in the room, you're a learn-it-all. And this podcast is for you.
Host Damon Lembi is a 3x bestselling author, CEO of Learnit, and someone who has spent 30 years watching what separates leaders who keep growing from those who quietly become the ceiling that limits everyone around them.
Each episode features real conversations with top executives, founders, NYT bestselling authors, and world-class athletes — people who've faced adversity, made costly mistakes, and done the hard, unglamorous work of growing. They share what they learned — and unlearned — to lead at the next level.
Great leaders aren't born or made. They're always in the making.
Let's not do that work alone.
Stay curious. Keep learning.
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61episodes
Episodes
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292. The Ancient Leadership Principle That The Top 1% Leaders Know | DJ Vanas
May 501:02:25Tap to summarizeWhat if the strongest leaders aren’t the ones who fight alone, but the ones who know how to serve, protect, and build a tribe around them?In this episode of The Learn-It-All™ Podcast, Damon sits down with internationally acclaimed speaker and bestselling author, DJ Vanas, to unpack an ancient leadership principle that still separates top leaders from average managers: real warriors are contributors, protectors, and servants who develop themselves so they can serve others at a higher level.DJ reframes the warrior through a Native American tribal lens, far away from the Hollywood version of toughness. He explains why great leadership is about building your tribe by design, earning respect rather than chasing approval, giving honest feedback with care, and building trust through small, high-quality interactions where people feel seen, heard, and supported.Damon and DJ also explore resilience, self-awareness, humility, lifelong learning, and why leaders cannot serve well if they are falling apart themselves. From DJ’s Air Force experience to the wisdom of elders and his own personal challenges, this conversation is packed with practical leadership lessons for anyone who wants to lead with courage, serve with purpose, and become the kind of person others can count on.In This Episode, You’ll Learn:Why “if I want it done right, I’ll do it myself” is the fastest path to burnout and how great leaders learn to delegate and develop others instead.How to build your “tribe by design” by surrounding yourself with people who protect your dreams, challenge your thinking, and help you grow.The self-awareness question DJ uses during tough moments: “What story am I telling myself right now?” and how that story shapes your outcome.Why failure should expand your perspective, not shrink it, and how to pull the right lessons instead of letting one bad experience define you.How trust is built through small, high-quality interactions when leaders are fully present and genuinely willing with their time.Why you can’t lead at a high level if you’re falling apart and why self-care is a non-negotiable part of leadership, not a luxury.How DJ uses intentional daily practices like meditation, journaling, exercise, sleep, and solitude to stay grounded, disciplined, and effective as a leader.Timestamps00:00 Episode preview and introduction03:05 Why top performers struggle when they become leaders04:35 The fastest way leaders accidentally burn themselves out06:07 How to build your tribe by design, not by accident09:19 The slow drip poison of surrounding yourself with dream killers11:26 Why honest feedback only works when trust is already there14:51 The paradox that hits when you need people the most15:54 The self-awareness question that can pull you out of autopilot20:38 The Mark Twain lesson most leaders learn too late22:31 How DJ turned one of his hardest seasons into deeper service26:45 The warrior principles leaders can use today28:49 The six tribal roles that still apply to modern leadership30:27 The hard choice every chief has to make35:12 How great leaders bring hidden potential out of their people40:21 The elder lesson DJ says is hard to unhear42:56 Why humility keeps leaders green and growing44:33 The ego trap that keeps leaders stuck50:51 Why you cannot be a warrior when you are falling apart51:41 The habits DJ uses to protect his energy and leadership55:52 Why getting older is automatic, but becoming an elder is not57:48 Why organizations bring DJ in to build resilience and mental toughness1:00:27 Where to find DJ VanasAbout DJ VanasDJ Vanas is an internationally recognized speaker, bestselling author, and enrolled member of the Ottawa Tribe of Michigan. Through his work, DJ teaches leaders and organizations how to apply traditional warrior principles to modern leadership, resilience, service, and personal development. He is the author of The Warrior Within and The Tiny Warrior, and has delivered his message to hundreds of tribal nations, corporations, government agencies, schools, and leadership teams across the country. Drawing from Native American traditions, his Air Force background, and decades of work with servant leaders, DJ helps people strengthen their mindset, build resilience, take better care of themselves, and serve their tribe with courage, humility, and purpose.Resources and MentionsThe Warrior Within book: https://www.amazon.com/Warrior-Within-Power-Serve-Protect/dp/0593423011The Tiny Warrior book: https://www.amazon.com/Tiny-Warrior-Personal-Discovery-Achievement/dp/0740733885DJ Vanas’ LinkedIn: https://www.linkedin.com/in/djvanas/DJ Vanas’ website: https://nativediscovery.com/Discovering Your Warrior Spirit: https://www.youtube.com/watch?v=-_fisn9PJJUPodcast Contact Information:Website: www.learnit.comEmail: podcast@learnit.comFollow us on LinkedIn and Instagram for updates.
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291. The One Rule That Separates Great Leaders From Average Managers | Tyler Dickerhoof
Apr 2801:06:20Tap to summarizeWhat if the leadership trait you’re most proud of is the exact thing quietly breaking trust with your team?In this episode of the Learn-It-All™ podcast, Damon Lembi sits down with leadership coach and author of the book The Things We Hide, Tyler Dickerhoof, to unpack the one rule that separates great leaders from average managers: stop making leadership about proving yourself, and start making it about bringing out the best in other people. Tyler explains why first-time leaders need belief poured into them, why vulnerability builds credibility instead of weakening it, and why trying to be the smartest person in the room usually backfires. He also breaks down his BEST framework for leadership, the “four walls” of insecurity that sabotage connection, and why AI will only make human leadership, self-awareness, and authentic communication more valuable.If you’re leading through change, fighting impostor syndrome, managing team performance, navigating layoffs, or trying to become a more confident and emotionally intelligent leader, this conversation with Damon Lembi and Tyler Dickerhoof is packed with practical leadership advice you can use right away.In This Episode, You’ll Learn:How Tyler’s BEST framework starts with helping people understand what they’re uniquely great at, because “go do your best” is useless if nobody knows what their best actually looks like.Why leaders lose trust when they compete with their own team, and how better leadership means helping people raise their floor, find their ceiling, and serve others with their strengths.The shift from trying to be the smartest person in the room to becoming the kind of leader who makes other people feel smart, seen, valued, and worthy.Tyler’s four protective walls of insecurity: intensity, insensitivity, inactivity, and isolation, and how those patterns quietly block connection, trust, and real leadership.What Tyler means by “what you hide controls you, what you face transforms you,” and how authentic vulnerability can deepen relationships without turning into weakness or oversharing.How Tyler’s personal story and the message behind The Things We Hide are really about helping people realize they are not alone, and that the things they hide do not have to define how they lead.Timestamps00:00 Episode preview and introduction01:02 Why new leaders feel like they don’t belong02:56 The leadership indictment most bosses miss03:44 Why “just do your best” is terrible advice07:10 The fastest way to kill team trust09:17 The moment someone’s belief changed Tyler’s life13:30 The missing piece of leadership most people skip14:40 Why the lowest person in the room should speak first17:42 The pressure trap of trying to have all the answers20:04 How to make people feel smart instead of small22:13 What it feels like to stop proving yourself25:12 Why mindset is a daily reset, not a one-time fix29:58 The story Tyler hid for years33:13 The two questions nearly everyone is quietly asking37:59 How leaders should handle guilt after layoffs42:47 The baseball analogy that explains better leadership46:44 Why AI makes human leadership more important49:48 You have to do the work yourself, but not alone50:37 Why lone wolves usually aren’t as strong as they think54:26 What you hide controls you58:59 Can vulnerability make you look weak?01:02:34 The ultimate compliment Tyler hopes readers give him01:04:36 Where to connect with Tyler DickerhoofAbout Tyler DickerhoofTyler Dickerhoof is a leadership coach, speaker, podcast host, and the founder of Impact Driven Leader. He describes his mission as helping people build the self-awareness, tools, and community they need to lead with more authenticity, connection, and impact. He is also the author of The Things We Hide, a book focused on the fears, insecurities, and old wounds that shape how people show up in leadership, relationships, and life.Resources and MentionsThe Things We Hide book: https://www.tylerdickerhoof.com/bookTyler Dickerhoof’s website: https://www.tylerdickerhoof.com/Tyler Dickerhoof’s LinkedIn: https://www.linkedin.com/in/tylerdickerhoof/Tyler Dickerhoof’s Instagram: https://www.instagram.com/tyler_dickerhoof/The Tyler Dickerhoof Show: https://www.youtube.com/@thetylerdickerhoofshowDamon Lembi on The Tyler Dickerhoof Show: https://www.youtube.com/watch?v=aEK-kk6-wlUPodcast Contact Information:Website: www.learnit.comEmail: podcast@learnit.comFollow us on LinkedIn and Instagram for updates.
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290. You're Not Behind (Yet): How Leaders Need To Adapt With AI | Danielle Clark
Apr 2100:50:01Tap to summarizeAI is not waiting for your team to catch up. If leaders keep treating artificial intelligence like a side experiment instead of a business shift, they are going to fall behind.In this episode of the Learn-It-All™ podcast, Damon Lembi sits down with Danielle Clark, VP of Global Talent at eBay, to unpack what AI leadership actually looks like inside a global company, and why the real challenge is not that the tech is not ready. It is that most humans are still learning how to work with it.Danielle breaks down how leaders can guide teams through AI adoption, workplace transformation, and the future of work without creating panic, resistance, or empty hype. She explains why the best leaders are not starting with shiny tools. They are starting with the core problem, the workflow, and the outcome they are trying to achieve. From AI upskilling and employee enablement to AI in recruiting, onboarding, coaching, and learning and development, this conversation explores how organizations can build more capacity, move with more velocity, and still keep the human side of work front and center.Danielle shares what it takes to create momentum at scale, how eBay approached AI essentials and ambassador networks, why human judgment still matters most, and what leaders must do now if they do not want their teams and themselves to get left behind.In This Episode, You’ll Learn:Why the strongest AI leaders are not obsessing over every new tool, but are instead leading with confidence, empathy, vulnerability, and clarity through constant changeWhy Danielle says the companies getting traction are the ones willing to throw everything up in the air and rethink workflows from the ground up, instead of just tweaking old processesWhy framing AI around tasks, workflows, and outcomes reduces fear better than telling people they need to reinvent their entire jobHow eBay drove adoption by combining executive sponsorship, experimentation, AI Essentials training, and an AI ambassador network that translated tools into real use cases for different teamsWhy employer expectations, customer expectations, and employee expectations have all gone up, and why Danielle believes people who refuse to lean in risk getting left behindWhy learning and development has a huge opportunity right now to earn a bigger seat at the table by acting as a scalable business partner in AI upskillingTimestamps00:00 - Episode preview and introduction02:58 - The tech is ready, the humans aren’t04:24 - What thriving leaders are doing that frustrated leaders aren’t07:50 - How do you tell someone it’s time to rethink their job?09:38 - Where AI helps most and where work still needs to stay human11:48 - How eBay got 9,000 employees to lean into AI14:54 - The two expectations leaders now have that change everything16:57 - What to do when executives want roi faster than people can adapt22:29 - How to use AI in hiring without losing the human judgment27:14 - Why AI coaching may help people ask for support they’d never ask a human for30:41 - Danielle’s surprising take on ChatGPT vs Gemini for giving feedback35:53 - The real risk of AI fatigue and how to avoid it37:50 - Why learning and development suddenly has a bigger seat at the table40:40 - What C-suites actually want to hear from L&D right now43:02 - Why grace and psychological safety matter more than perfection46:48 - What will still be fundamentally human five years from now48:39 - Damon’s closing challenge for leaders navigating AI changeAbout Danielle ClarkDanielle Clark is the VP of Global Talent at eBay, where she leads work across areas including recruiting, learning and development, onboarding, and performance-related talent initiatives. A former consultant, Danielle brings a sharp perspective on leadership, workforce transformation, and how companies can adopt AI without losing the human skills that matter most.Resources and MentionsDanielle Clark’s LinkedIn: https://www.linkedin.com/in/danielle-clark-sf/Learn-It-All Press: Book a discovery call at www.learnitallpress.comPodcast Contact Information:Website: www.learnit.comEmail: podcast@learnit.comFollow us on LinkedIn and Instagram for updates.
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289. The Reason You Still Feel Empty After Getting Everything You Wanted | Jim Murphy
Apr 1400:48:58Tap to summarizeWhy do so many high achievers still feel empty after getting everything they thought they wanted?In this episode of The Learn-It-All Podcast, Damon Lembi sits down with Jim Murphy, #1 New York Times bestselling author of Inner Excellence, to unpack why success without meaning still leaves people anxious, restless, and unfulfilled. Jim explains why chasing what he calls the “PALMS”: possessions, achievements, looks, money, and status, can never satisfy the deeper human need for love, acceptance, peace, and purpose.Drawing from his own journey from failed baseball dreams to coaching elite athletes, CEOs, and world-class performers, Jim shares why the best possible life is not built on transactions or external validation, but on learning and growing every day, becoming more self-aware, and pursuing what makes you feel fully alive. Damon and Jim also discuss the moment NFL player A.J. Brown from the Philadelphia Eagles helped send Inner Excellence into the spotlight, and why that breakthrough only reinforced Jim’s deeper message: fulfillment does not come from fame, money, recognition, or finally “making it.”The conversation also explores how to overcome impostor syndrome, master the ego, become more present in a distracted world, raise mentally strong kids, and understand the powerful difference between belief and confidence. If you’ve ever hit a goal and still felt like something was missing, this episode will help you rethink success, emotional resilience, inner peace, and what it really means to live with inner excellence.In This Episode, You’ll Learn:Why achieving your biggest goals can still leave you empty if your life is built around outcomes instead of meaningJim Murphy’s “PALMS” framework: possessions, achievements, looks, money, and status, and why so many people chase them, hoping they’ll finally feel loved and enoughWhat the A.J. Brown moment revealed about sudden visibility, success, and why external validation still doesn’t create lasting fulfillmentWhy impostor syndrome is often a self-centered fear loop of “What do they think of me?” and how humility helps break itHow top performers develop courage by becoming willing to feel embarrassment, uncertainty, failure, and discomfortThe crucial difference between confidence and beliefHow to stop treating life like a series of transactions and start building one with purpose, presence, courage, and peaceTimestamps:00:00 Episode preview and introduction01:15 The core of inner excellence: learning and growing every day03:56 The question that shaped Jim’s life: how to stay calm under pressure06:45 What it really means to feel fully alive08:55 What to do when life feels like pure suffering09:07 The “PALMS” trap: possessions, achievements, looks, money, and status11:04 Impostor syndrome and how humility dissolves it12:29 Happiness vs. joy and why most people chase the wrong one13:44 Why ego is the biggest blocker to extraordinary performance15:06 Why “the best possible life” matters more than performance alone17:10 The Michael Phelps principle and accurate self-awareness21:17 How Jim coaches clients: WTF, DWTF, and lifestyle design23:24 The one trait elite performers all seem to have26:34 What being fully present actually means28:02 The two-minute presence practice29:14 Why you can’t be grateful and anxious at the same time30:18 The Float Up Tool and getting out of mental transactions31:27 Damon’s phone reminder trick for becoming more present32:15 How to help kids become mentally tough33:14 Why belief matters more than confidence34:09 The golf story that changes how you think about good and bad outcomes37:45 Jim on ego, fame, and wanting everyone to think he was the best39:48 The two turning points that changed Jim’s life40:50 Jim’s reaction when the A.J. Brown moment exploded42:56 Jim’s new book The Best Possible Life45:10 What makes Inner Excellence different from sports psychology46:37 AI, unlearning, and adapting to the future of work47:36 Damon’s closing challenge on gratitude, comparison, and serving others48:06 Where to connect with JimAbout Jim MurphyJim Murphy is the author of Inner Excellence and The Best Possible Life, and one of the leading voices on mindset, presence, performance, and fulfillment. A former professional baseball player, Jim turned a painful end to his athletic career into a years-long search for what creates true peace, courage, and extraordinary performance under pressure.Today, Jim works with elite athletes, executives, teams, and organizations to help them overcome mental blocks, perform at a higher level, and build lives rooted in meaning rather than ego or external validation. His work centers on what he calls inner excellence: training the mind and heart to live with more love, wisdom, courage, self-awareness, and presence.Resources and MentionsInner Excellence: Train Your Mind for Extraordinary Performance and the Best Possible Life: https://www.amazon.com/INNER-EXCELLENCE-Extraordinary-Performance-Possible/dp/1734654805The Best Possible Life: How to Live with Deep Contentment, Joy, and Confidence--No Matter What: https://www.amazon.com/Best-Possible-Life-Contentment-Confidence-No/dp/1734654848Jim Murphy’s LinkedIn: https://www.linkedin.com/in/innerexcellence/Jim Murphy’s Instagram: https://www.instagram.com/innerexcellencejimmurphy/?hl=enJim Murphy’s website: https://innerexcellence.com/Jim Murphy’s newsletter: https://innerexcellence.substack.com/Inner Excellence Retreats: https://innerexcellence.com/retreats/Podcast Contact Information:Website: www.learnit.comEmail: podcast@learnit.comFollow us on LinkedIn and Instagram for updates.
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288. How to Get the Most Out of Your Financial Advisor (Most People Don’t) | CJ Davidson
Apr 700:35:45Tap to summarizeWhat happens when you’re good enough to get in the room — and then don’t like what you see?CJ Davidson spent years grinding his way up in traditional financial services. Cold-calling attorneys from a $5 street tie. Earning trust one client at a time. Building something real.And then, when he finally got a seat in the leadership meetings, he realized the client wasn’t even in the conversation.That moment didn’t break him. It built Proxy Financial.In this episode of The Learn-It-All Podcast, Damon sits down with CJ — Founder and CEO of Proxy Financial — to talk about what it actually takes to build a culture where doing the right thing when no one is looking isn’t a policy. It’s the whole point.This one goes well beyond financial advice. It’s about curiosity over compliance, art over script, and what happens when you stop asking permission to do things that just make sense.In This Episode, You’ll LearnWhy CJ got pushback for buying his clients cocktails — and how that moment revealed everything wrong with the system he was inThe difference between a financial professional who’s technically sharp and one who’s actually right for youWhy you don’t need a lot of money to benefit from a great advisor — you need a goal you’re not confident executing aloneHow CJ thinks about AI: not as a threat, but as the thing that finally frees advisors to do the human work that actually builds trustWhy he tells aspiring financial professionals to major in psychology and minor in financeWhat “doing the right thing when no one is looking” looks like inside a company built around itChapters00:00 Episode preview and introduction00:54 What CJ Davidson saw inside traditional financial services03:48 The “art and science” of financial advice05:14 The client mixer idea that challenged the old playbook09:27 Moving from advisor to leadership and teaching fiduciary thinking11:41 Seeing how “the soup was made” inside corporate finance14:33 Why CJ helped build Proxy Financial16:22 How to test a business hypothesis before going all in17:50 Building a mission-aligned culture on a distributed team19:03 How to choose a financial advisor who is actually the right fit25:26 Proxy Financial’s long-term vision and advisor succession28:06 Ethics, temptation, and doing the right thing when no one is looking30:25 How AI is changing financial advice without replacing human trust33:45 Where listeners can connect with CJ Davidson35:33 CJ’s take on confidence vs. arroganceAbout CJ DavidsonCJ Davidson is the Founder and CEO of Proxy Financial. He works closely with financial advisors and business owners who want to do right by their clients while building businesses designed to last. His approach is centered on ethical, relationship-first financial advice, long-term protection, and sustainable growth. CJ also takes a holistic view of wealth that includes health, perspective, and balance.Resources and MentionsCJ Davidson’s LinkedIn: https://www.linkedin.com/in/cjdavidsonplanner/Proxy Financial’s website: https://www.proxyfinancial.com/Marked Unread Podcast: https://www.proxyfinancial.com/marked-unread-podcast/Working Genius: https://www.tablegroup.com/workinggenius/Unreasonable Hospitality book: https://www.amazon.com/Unreasonable-Hospitality-Remarkable-Giving-People/dp/0593418573Podcast Contact Information:Website: www.learnit.comEmail: podcast@learnit.comFollow us on LinkedIn and Instagram for updates.
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287. Leadership Expert: “Before You Accept A Promotion, Ask Yourself This…” | Vincent Wanga
Mar 3101:02:30Tap to summarizeWhat if the promotion you want is the very thing that could derail your career?In this episode of The Learn-It-All™ Podcast, Damon Lembi sits down with Vincent Wanga, award-winning creative executive and author of The Art of Direction, to unpack the first question every high performer should ask before becoming a leader: why? Vincent explains why leadership is not just the next step for top individual contributors, why chasing money, power, and glory is a dangerous reason to say yes, and why leading people is ultimately an empathetic and selfless pursuit. He also breaks down the difference between execution skills and leadership skills, why some of the best performers fail once they move into management, and how to know whether leadership is actually aligned with who you are.Drawing from his own improbable career, from getting kicked out of art school to freelancing his way back into the industry, scaling teams in high-growth tech, and learning hard lessons through failure, Vincent shares practical leadership advice for emerging leaders, entrepreneurs, executives, and ambitious professionals navigating career growth in an AI-driven world.Damon and Vincent also explore delusional optimism, accountability, confidence versus arrogance, corporate politics, mentorship, and the human skills that matter most in modern leadership, including empathy, decisiveness, adaptability, and relationship-building. If you are wondering whether leadership is the right path for you, or how to become a stronger leader without losing yourself in the process, this conversation is packed with real-world insight.In This Episode, You’ll Learn:Why the first question to ask before accepting a leadership role is not about salary, title, or power, but why you want it in the first placeHow great executors get pushed into leadership roles that do not fit them, and what to do if you already took the job and know it was the wrong moveThe difference between confidence and arrogance, and why Vincent says failure taught him more than books, podcasts, and “pocket MBAs” ever didWhy empathy, politics, decisiveness, and relationship-building are still the real human advantage in an AI worldWhy mentorship is everything, and why real leaders should see developing people as part of their legacyTimestamps00:00 Episode preview00:42 The first question to ask before saying yes to leadership02:29 Why leadership is not for everybody04:59 What to do if you have already accepted the wrong leadership role08:04 Vincent Wanga’s improbable path into creativity and leadership10:02 Getting kicked out of school and rebuilding from scratch12:24 What to do after losing your dream job15:31 Delusional optimism, entrepreneurship, and betting on yourself19:06 The branding project that humbled Vincent’s ego25:17 Scaling a team 20x and the leadership lesson that stayed with him31:03 Why Vincent wrote The Art of Direction35:36 Gen Z, alternate paths, and redefining leadership37:16 The human skills that matter most in the AI era42:08 How leaders should handle executive pushback and boardroom politics47:24 AI as a tool, not a crutch53:13 Why mentorship is everything58:24 What leadership could look like 20 years from now01:01:22 Where to connect with Vincent WangaAbout Vincent WangaVincent Wanga is a creative leader, entrepreneur, and author of The Art of Direction: Personal Perspectives on the Path to Creative Leadership. Originally from Kenya and raised in the Twin Cities, Vincent built a two-decade career across design, branding, entrepreneurship, agency leadership, and high-growth tech. His journey has included early setbacks, major reinvention, executive leadership, and hard-earned lessons around accountability, resilience, empathy, and business outcomes.Resources and MentionsThe Art of Direction: Personal Perspectives on the Path to Creative Leadership: https://www.amazon.com/Art-Direction-Personal-Perspectives-Leadership/dp/B0DXJ4MLG7Vincent Wanga’s website: https://www.vincentwanga.com/Vincent Wanga’s LinkedIn: https://www.linkedin.com/in/vincent-wanga/Good to Great book by Jim Collins: https://www.amazon.com/Good-Great-Some-Companies-Others/dp/0066620996The 7 Habits of Highly Effective People by Stephen R. Covey: https://www.amazon.com/Habits-Highly-Effective-People-Powerful/dp/0743269519Podcast Contact Information:Website: www.learnit.comEmail: podcast@learnit.comFollow us on LinkedIn and Instagram for updates.
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286. Why Most Founders Aren’t Ready to Scale | Ray Lane
Mar 2401:15:22Tap to summarizeWhat does it really take to walk into a company everyone says is finished and turn it into a comeback story?In this episode of The Learn-It-All™ Podcast, Damon Lembi sits down with legendary operator and investor Ray Lane for a masterclass on leadership, company turnarounds, founder potential, and scaling a business without losing the plot. Ray shares the hard-earned lessons that took him from an unexpected first leadership role in college to IBM, EDS under Ross Perot, the high-stakes turnaround of Oracle, Kleiner Perkins, and now GreatPoint Ventures.This conversation goes deep into how to turn around a struggling company, what great founders do differently, why most technical founders make the same go-to-market mistake, and how leaders build organizations that can actually scale. Ray breaks down what Oracle looked like when he arrived, why the company had become a “wild wild west,” how he rebuilt customer trust, and why leadership is not just about winning battles but winning the war. He also explains the critical difference between a founder, an entrepreneur, and a CEO, what he looks for in startup pitches today, and why the first 30 seconds of a founder’s explanation can tell you almost everything.If you are a founder, executive, operator, investor, or aspiring leader trying to understand startup leadership, software company scaling, sales organization transformation, venture capital founder advice, or how great leaders inspire performance, this episode is packed with practical insight and real-world stories from the front lines of Silicon Valley.In This Episode, You’ll Learn:Why Ray Lane says people leave for context and get recruited away for content, and what that means for retaining top performersWhat IBM taught him about discipline, structure, and leadership development, and what EDS taught him that IBM never couldWhy Ross Perot’s interview style forced Ray to stop hiding behind company credentials and explain why he was the right personWhat Oracle looked like when Ray joined, why customers had lost confidence, and how bad the mess really was behind the scenesHow Ray rewrote Oracle’s sales rules, ripped up bad customer contracts, and moved the company away from short-term wins that destroyed long-term trustThe difference between a diminisher and a multiplier, and why Ray believes leaders should inspire people, not shrink themWhy most founders are not automatically entrepreneurs, and most entrepreneurs are not automatically CEOsWhat Ray looks for in a startup pitch, including why a founder should be able to explain the problem and opportunity in 30 secondsTimestamps[00:00] Episode preview and introduction[02:29] Ray’s first leadership role and the surprise of becoming fraternity president[04:21] Setting a bold goal and scaling the fraternity from 25 to 125 brothers[06:54] How college leadership built Ray’s confidence and social fluency[09:11] IBM’s culture, structure, and the belief that anyone could become CEO[10:38] The call that pulled Ray from IBM to EDS[11:48] Ross Perot’s intense interview and why Ray wanted in[13:01] What EDS taught Ray about hiring, P&L ownership, and pressure[15:26] Trial and error leadership versus the IBM playbook[19:28] Facing risk, buying software, and learning to take responsibility[22:08] Why Ray left EDS and the leadership lesson behind it[24:19] Booz Allen, rapid growth, and the CEO path Ray thought he wanted[25:21] The recruiter call about Oracle and why it did not look attractive[29:11] Ray’s four-hour meeting with Larry Ellison[31:16] Oracle’s broken model and the vision that changed Ray’s mind[35:13] Rewriting Oracle’s rules and rebuilding the business[36:58] Why Oracle was worse than Ray expected when he got inside[40:35] The data that shocked Ray most: customers disliked Oracle[42:30] Killing Sybase and building Oracle’s applications and consulting engine[51:22] Multipliers vs diminishers and Ray’s leadership philosophy[54:28] Winning battles versus winning the war[59:05] Why Oracle taught Ray more than IBM or EDS ever did[01:01:05] “Be a leader, inspire people,” and the difference between managers and leaders[01:04:10] What Ray Lane looks for in founders today[01:06:41] Why most founders get go-to-market wrong[01:09:29] From Oracle to Kleiner Perkins to GreatPoint Ventures[01:13:37] The kind of AI and healthcare founder Ray wants to backAbout Ray LaneRay Lane is a veteran technology executive, operator, and investor best known for helping lead one of the most important turnarounds in enterprise software history at Oracle, where he served as President and COO. Before Oracle, he built his leadership foundation at IBM, sharpened his operator instincts under Ross Perot at EDS, and later became a senior leader at Booz Allen Hamilton. After Oracle, Ray spent 14 years as a Managing Partner at Kleiner Perkins, working closely with founders and high-growth companies, and he is now the Co-Founder and Managing Partner of GreatPoint Ventures, where he focuses on backing entrepreneurs solving major problems in healthcare and the enterprise, especially through AI.Resources and MentionsRay Lane’s LinkedIn: https://www.linkedin.com/in/raymond-lane-wvu68/GreaPoint Ventures website: https://www.gpv.com/On Wings of Eagles book by Ken Follett: https://www.amazon.com/Wings-Eagles-Inspiring-Spirit-Countrymen/dp/0451163532Multipliers book by Liz Wiseman: https://www.amazon.com/Multipliers-Best-Leaders-Everyone-Smarter/dp/0061964395Podcast Contact Information:Website: www.learnit.comEmail: podcast@learnit.comFollow us on LinkedIn and Instagram for updates.
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285. Little League Baseball Teaches Kids to Fail — Here’s Why That’s a Good Thing | Damon Lembi
Mar 1800:06:11Tap to summarizeWhat if the very thing parents try hardest to protect their kids from is exactly what helps them grow?In this solo episode of The Learn-It-All™ Podcast, Damon Lembi shares why Little League baseball teaches kids to fail, and why that’s one of the greatest gifts youth sports can offer. From the excitement of opening day and breaking in a new glove with his dad, to striking out four times in one game at Arizona State, Damon reflects on the life and leadership lessons that started on the baseball field.This episode is a powerful reminder for parents, coaches, and leaders that youth sports are about far more than wins and losses. They teach kids how to show up, compete, be a good teammate, handle disappointment, and build resilience through failure. Damon also challenges parents not to “bubble wrap” their kids or make excuses when things do not go their way. Instead, he makes the case for letting failure become a learning moment that builds courage, confidence, and character.If you care about raising resilient kids, coaching with intention, teaching confidence through sports, or helping young athletes handle failure, this episode is packed with practical perspective and hard-earned wisdom from Damon’s own journey in Little League, college baseball, leadership, and life.In This Episode, You’ll Learn:What Damon believes parents and coaches get wrong when they make excuses instead of helping kids grow through setbacksThe story of not making a youth soccer team and the tough-love lesson Damon’s dad gave him that stayed with him foreverHow Damon rebounded after striking out four times in one game at Arizona State, and what his coach said that restored his confidenceWhy Little League is not really about winning or losing, but about showing up, giving your best, being a good teammate, and having funHow youth sports help kids develop the confidence, discipline, and courage they’ll later need in leadership, business, and lifeTimestamps00:00 – Opening memories of Little League and the joy of getting ready for the season01:15 – Damon’s salute to parents and coaches who make youth sports possible01:47 – The lifelong skills kids learn through sports, from teamwork to discipline02:09 – Why parents and coaches need to let kids fail instead of bubble wrapping them02:28 – Damon’s story of not making the soccer team and the lesson his dad taught him03:18 – Striking out four times against Michigan and what happened the next day04:21 – Why sports gave Damon the courage to lead teams and work with thousands of leaders04:43 – What Little League is really about, and why winning is not the point05:38 – Damon’s message to parents about support, perspective, and having a great season06:00 – Closing thoughts and who this episode should be shared withAbout Damon LembiDamon Lembi is a 3x bestselling author, the host of The Learn-It-All™ Podcast, and CEO of Learnit – a live learning platform that has upskilled over 2 million people. Drawing from his prior baseball career, Damon brings an athlete’s perspective to leadership. Through his journey, he has gained invaluable insights into what helps organizations grow, how great leaders learn, and why learn-it-all companies outpace their competitors every time.Resources and Mentions:Connect with Damon: https://www.linkedin.com/in/damonlembi/Download Damon’s book: https://BookHip.com/FTZRCJBCoach Steve Knudsen: https://www.facebook.com/steve.knudsen.9?mibextid=wwXIfrPodcast Contact Information:Website: www.learnit.comEmail: podcast@learnit.comFollow us on LinkedIn and Instagram for updates.
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284. Former CEO of 7-Eleven and Blockbuster on Confidence, Reinvention, and Why Education Is Freedom | Jim Keyes
Mar 1701:06:25Tap to summarizeWhat if the biggest thing holding leaders back is not failure, disruption, or AI, but fear?In this episode of The Learn-It-All Podcast, Damon Lembi sits down with Jim Keyes, former CEO of 7-Eleven and Blockbuster, for a conversation on confidence, reinvention, lifelong learning, and the mindset it takes to lead when the stakes are high. Jim reflects on helping lead a major turnaround at 7-Eleven, stepping into Blockbuster during one of its most turbulent chapters, and the hard-won lessons that came from navigating crisis instead of running from it.Jim also shares his story of bumping into Warren Buffett during the Blockbuster years, when he was slipping into a victim mindset, and how Buffett’s challenge became the wake-up call he needed to keep fighting rather than give up. Damon and Jim use that story to unpack a bigger idea: confidence is not something you’re simply born with. It is built on knowledge, faith, preparation, and the willingness to keep learning in the face of adversity.The conversation also explores Jim’s belief that education is freedom, why a degree is a license to learn, and how leaders can turn change into opportunity rather than fear. If you care about leadership development, business reinvention, executive confidence, change management, learning agility, and the future of education in an AI-driven world, this episode delivers both perspective and practical wisdom.In This Episode, You’ll Learn:Why Warren Buffett’s question became the mindset shift Jim needed when he was tempted to fall into a victim mentality at Blockbuster.How a student wearing an “Education Is Freedom” shirt at Columbia stopped Jim in his tracks and helped him realize that education was never just about money, but about freedom, options, and a bigger life.Why Jim believes confidence is not something you’re born with, but a learned skill built through knowledge, preparation, repetition, and the belief that you can learn your way through almost any problem.What most people still miss about the Blockbuster case study, and why the lazy “Netflix beat Blockbuster” version leaves out the hard stuff leaders actually need to understand.How Jim borrowed from Sam Walton’s playbook at 7-Eleven to cut through 12 to 15 layers of management and make sure every store heard the same priorities directly from leadership.Why leaders need change, confidence, and clarity to keep fear from spreading through a company during periods of uncertainty.Timestamps[00:00] Episode preview and introduction[02:00] When learning first became Jim’s path to freedom[03:08] The Columbia T-shirt that led to Education Is Freedom[04:27] “Money’s just a way of keeping score”[06:21] Fear, insecurity, and why confidence is learned[11:50] Knowledge, faith, and the game-changing Warren Buffett story[17:32] Why the Blockbuster story is richer than the easy headline[21:19] “I never lose. I win or I learn.”[22:51] The Sam Walton communication lesson Jim used at 7-Eleven[26:24] Change, confidence, clarity, and the CEO mindset[27:18] Pilot training, neuroplasticity, and replacing fear with knowledge[33:46] Character, personal brand, and what sustainable leadership really looks like[38:41] Why smart leaders stop hearing the truth[44:55] The human skills AI still can’t replace[46:20] Breadth of learning vs narrow specialization[49:38] The why of learning in a fearful, polarized world[53:11] Why Jim is more hopeful about Gen Z than most people[55:21] Jim’s case for reinventing education with technology[01:00:17] Ignorance as the root cause and the JFK-style challenge[01:01:56] The butterfly story and why the future is in your hands[01:04:39] Where to connect with Jim KeyesAbout Jim KeyesJim Keyes is a business leader, author, speaker, and educator best known as the former CEO of 7-Eleven and Blockbuster. He led a major turnaround at 7-Eleven, later took the helm at Blockbuster during one of the most difficult periods in the company’s history, and today shares leadership lessons drawn from those experiences worldwide. Jim is also the author of Education Is Freedom, a book and message centered on lifelong learning, adaptability, and the idea that education creates options, confidence, and opportunity.Resources and MentionsEducation is Freedom book: https://www.amazon.com/Education-Freedom-Future-Your-Hands/dp/1637588003Jim Keyes’ website: https://www.jameswkeyes.com/Jim Keyes’ LinkedIn: https://www.linkedin.com/in/james-keyes-a0947215/Jim Keyes’ Instagram: https://www.instagram.com/jkeyesauthor/Jim Keyes’ TikTok: https://www.tiktok.com/@jkeyesauthorHarvard Business School Case on Blockbuster, Netflix, and Redbox: https://hbsp.harvard.edu/product/KEL616-PDF-ENGThe Learn-It-All™ Podcast: The Ask Approach with Jeff Wetzler: https://www.youtube.com/watch?v=FmuBcUBlvOkPodcast Contact Information:Website: www.learnit.comEmail: podcast@learnit.comFollow us on LinkedIn and Instagram for updates.
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283. Why Your Brain Shuts Down Under Pressure | Rob Kalwarowsky
Mar 1000:43:56Tap to summarizeWhy do 89% of leaders freeze under pressure while a small few get clearer, calmer, and more decisive?In this episode of The Learn-It-All Podcast, Damon Lembi sits down with executive coach, keynote speaker, and Capitalizing on Chaos author Rob Kalwarowsky to unpack what really happens to leaders during uncertainty, stress, burnout, and high-stakes decision-making.They dig into what Rob calls inner chaos, that feeling of being at war inside your own head, and why the best leaders are not the ones who pretend to be fearless, but the ones who know how to steady themselves in real time. Rob explains why saying “I’m human” can be a powerful leadership tool, how fight, flight, freeze, and fawn show up at work, and why leaders should never engage their teams from a dysregulated state. They also explore the hidden cost of perfectionism, the danger of people-pleasing leadership, the trap of trying to do everything yourself, and the mindset shift that helps emerging leaders stop freezing and start taking action.Rob also shares his personal story from MIT-trained engineer and elite athlete to surviving a mental health crisis, rebuilding from the inside out, and helping leaders find clarity, peace, and better performance in chaotic times. If you want to become a calmer, more effective leader in uncertainty and make better decisions without burning yourself out, this episode is for you.In This Episode, You’ll Learn:Why so many leaders freeze in uncertainty, and how an amygdala hijack shuts down logic, decision-making, and leadership when chaos hits.How the phrase “I’m human” can help leaders regulate faster, create empathy, and build trust with their teams in real time.Why inner peace and clarity make it easier to say yes to the right priorities and no to everything pulling you off your path.Why asking for help is the first courageous move when burnout, overwhelm, or darker thoughts start to spiral.Why Rob believes this chaotic season is a once-in-a-lifetime opportunity for leaders willing to take action while everyone else freezes.Timestamps:00:00 – Episode preview and introduction01:41 – Why chaos feels higher than ever03:42 – What an amygdala hijack does to leaders04:46 – The real-world power of saying “I’m human”07:31 – Why high achievers need grace, not just grind09:46 – Rob’s backstory: MIT, engineering, and a toxic culture13:05 – The first step when burnout turns dangerous15:38 – Why this is the right moment for Capitalizing on Chaos18:16 – Why fight-or-flight kills team engagement21:03 – Fawn, feedback, and the cost of being too nice23:19 – The DIY leader trap26:25 – The fastest way to spot if you’re the bottleneck28:39 – Imposter syndrome in new and emerging leaders35:35 – Two tools to ask for a raise, date, or promotion39:04 – What executives are struggling with right now40:45 – Why 89% of leaders freeze under pressure42:05 – Where to connect with RobAbout Rob KalwarowskyRob Kalwarowsky is an executive coach, keynote speaker, and the author of Capitalizing on Chaos. A Canada-born, MIT-trained mechanical engineer and former national team water polo player, Rob began his career in engineering before a toxic work environment and personal mental health crisis changed the course of his life. Today, he helps leaders navigate inner chaos, burnout, self-leadership, decision-making, and performance under pressure so they can lead with more clarity, calm, and impact.Resources and MentionsCapitalizing on Chaos Book: https://www.amazon.com/Capitalizing-Chaos-Executives-Succeed-Disruption-ebook/dp/B0FMQBYYBWRob Kalwarowsky’s website: https://www.robkalwarowsky.com/Find Your Reason Worksheet: https://www.robkalwarowsky.com/reasonRob Kalwarowsky’s LinkedIn: https://www.linkedin.com/in/rob-kalwarowsky/Podcast Contact Information:Website: www.learnit.comEmail: podcast@learnit.comFollow us on LinkedIn and Instagram for updates.
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