the Learn-It-All™ podcast

FREE Download The Learn-It-All Leader book

Every top performer has one leadership skill that rarely shows up in job descriptions, training programs, or performance reviews: self-awareness.

Most leaders don’t need another framework.

They need the truth about what’s actually driving how they lead.

In this solo episode of The Learn-It-All™ Podcast, Damon Lembi breaks down why self-awareness is the foundation behind every great leader, top performer, and high-functioning team.

Through powerful personal stories, from getting called out by legendary Arizona State baseball coach Jim Brock, to lessons from his father on respect, to hard-earned insights on discipline, feedback, and failure, Damon shows why leadership doesn’t start with strategy.

It starts with looking honestly at yourself.

This episode introduces a simple but transformative idea: becoming the “historian of your own life.” When you understand the people, experiences, and beliefs that shaped you, you unlock the ability to lead with intention instead of default.

If you’ve ever struggled with feedback, confidence, hiring, or consistency as a leader, this episode will challenge how you think and how you show up.

What You’ll Learn in This Episode

1. Why self-awareness is the most important leadership skill and why most leaders avoid it
2. How to become the “historian of your own life” and uncover the beliefs shaping your decisions
3. The hidden cost of acting like a know-it-all leader, especially in hiring and team building
4. A simple but powerful interview hack to spot genuine character versus performance
5. How worrying about what others think kills confidence, risk-taking, and growth
6. The leadership lesson Damon learned from two completely different role models, his father and grandfather
7. Why discipline, health, and mental clarity directly impact leadership performance
8. The turning point moment when harsh feedback from Coach Jim Brock changed Damon’s trajectory and what it teaches about accountability and growth
9. Why quitting drinking became a competitive advantage in Damon’s leadership and life

Key Takeaway

Self-awareness isn’t soft.

It is one of the hardest and most valuable skills you can build as a leader.

The best leaders don’t just learn more.

They understand themselves better and use that awareness to lead, decide, and grow differently.

Reflection Question for Leaders

Who is the “Coach Brock” in your life, the person who challenged you, called you out, or believed in you before you believed in yourself?

And more importantly, how are you showing up as that person for someone else?

Timestamps

• 00:00 – The brutal 7AM wake-up call at Florida State
• 00:56 – “Get your running shoes”: the morning Coach Brock called everyone out
• 01:34 – Damon gets called a “slow-thinking, slow-footed sloth”
• 02:34 – Five stories that shaped Damon’s leadership
• 03:17 – The first leadership lesson: treat everybody with respect
• 03:35 – How Damon’s mom taught him to make people feel welcome
• 04:25 – The parking garage story that revealed Damon’s dad’s character
• 05:38 – The interview mistake that made Damon’s team lose a great candidate
• 06:19 – Why “know-it-all” leaders push talented people away
• 07:39 – Damon’s hiring hack for spotting prima donnas early
• 08:37 – The hidden cost of caring too much about what people think
• 10:01 – How Damon’s insatiable appetite for learning started with his dad
• 11:44 – Why a learning mindset matters more than ever in the age of AI
• 12:01 – Damon compares the two biggest male influences in his life
• 12:37 – Mental toughness, discipline, heart, and the “trust tax”
• 14:02 – Why quitting drinking made Damon a sharper leader
• 15:06 – The swing that changed Damon’s baseball season
• 15:55 – The trophy Coach Brock always wanted Damon to have
• 16:31 – Who was the Coach Brock in your life?
• 16:56 – How to become that person for someone else

About Damon Lembi

Damon 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/FTZRCJB

How Leaders Learn by David Novak: https://www.amazon.com/How-Leaders-Learn-Master-Successful/dp/164782754X

Jason Menzo on The Learn-It-All Podcast: https://www.youtube.com/watch?v=OqJJz9bgOwM

Danielle Clark on The Learn-It-All Podcast: https://youtu.be/lD4yRHSob_0

Podcast Contact Information:

Website: www.learnit.com

Email: [email protected]

Follow us on LinkedIn and Instagram for updates.

What 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:

1. 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.
2. How to build your “tribe by design” by surrounding yourself with people who protect your dreams, challenge your thinking, and help you grow.
3. The self-awareness question DJ uses during tough moments: “What story am I telling myself right now?” and how that story shapes your outcome.
4. Why failure should expand your perspective, not shrink it, and how to pull the right lessons instead of letting one bad experience define you.
5. How trust is built through small, high-quality interactions when leaders are fully present and genuinely willing with their time.
6. 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.
7. How DJ uses intentional daily practices like meditation, journaling, exercise, sleep, and solitude to stay grounded, disciplined, and effective as a leader.

Timestamps

• 00:00 Episode preview and introduction
• 03:05 Why top performers struggle when they become leaders
• 04:35 The fastest way leaders accidentally burn themselves out
• 06:07 How to build your tribe by design, not by accident
• 09:19 The slow drip poison of surrounding yourself with dream killers
• 11:26 Why honest feedback only works when trust is already there
• 14:51 The paradox that hits when you need people the most
• 15:54 The self-awareness question that can pull you out of autopilot
• 20:38 The Mark Twain lesson most leaders learn too late
• 22:31 How DJ turned one of his hardest seasons into deeper service
• 26:45 The warrior principles leaders can use today
• 28:49 The six tribal roles that still apply to modern leadership
• 30:27 The hard choice every chief has to make
• 35:12 How great leaders bring hidden potential out of their people
• 40:21 The elder lesson DJ says is hard to unhear
• 42:56 Why humility keeps leaders green and growing
• 44:33 The ego trap that keeps leaders stuck
• 50:51 Why you cannot be a warrior when you are falling apart
• 51:41 The habits DJ uses to protect his energy and leadership
• 55:52 Why getting older is automatic, but becoming an elder is not
• 57:48 Why organizations bring DJ in to build resilience and mental toughness
• 1:00:27 Where to find DJ Vanas

About DJ Vanas

DJ 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 Mentions

The Warrior Within book: https://www.amazon.com/Warrior-Within-Power-Serve-Protect/dp/0593423011

The Tiny Warrior book: https://www.amazon.com/Tiny-Warrior-Personal-Discovery-Achievement/dp/0740733885

DJ Vanas’ LinkedIn: https://www.linkedin.com/in/djvanas/

DJ Vanas’ website: https://nativediscovery.com/

Discovering Your Warrior Spirit: https://www.youtube.com/watch?v=-_fisn9PJJU

Podcast Contact Information:

Website: www.learnit.com

Email: [email protected]

Follow us on LinkedIn and Instagram for updates.

What 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:

1. 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.
2. 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.
3. 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.
4. Tyler’s four protective walls of insecurity: intensity, insensitivity, inactivity, and isolation, and how those patterns quietly block connection, trust, and real leadership.
5. 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.
6. 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.

Timestamps

• 00:00 Episode preview and introduction
• 01:02 Why new leaders feel like they don’t belong
• 02:56 The leadership indictment most bosses miss
• 03:44 Why “just do your best” is terrible advice
• 07:10 The fastest way to kill team trust
• 09:17 The moment someone’s belief changed Tyler’s life
• 13:30 The missing piece of leadership most people skip
• 14:40 Why the lowest person in the room should speak first
• 17:42 The pressure trap of trying to have all the answers
• 20:04 How to make people feel smart instead of small
• 22:13 What it feels like to stop proving yourself
• 25:12 Why mindset is a daily reset, not a one-time fix
• 29:58 The story Tyler hid for years
• 33:13 The two questions nearly everyone is quietly asking
• 37:59 How leaders should handle guilt after layoffs
• 42:47 The baseball analogy that explains better leadership
• 46:44 Why AI makes human leadership more important
• 49:48 You have to do the work yourself, but not alone
• 50:37 Why lone wolves usually aren’t as strong as they think
• 54:26 What you hide controls you
• 58:59 Can vulnerability make you look weak?
• 01:02:34 The ultimate compliment Tyler hopes readers give him
• 01:04:36 Where to connect with Tyler Dickerhoof

About Tyler Dickerhoof

Tyler 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 Mentions

The Things We Hide book: https://www.tylerdickerhoof.com/book

Tyler 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/@thetylerdickerhoofshow

Damon Lembi on The Tyler Dickerhoof Show: https://www.youtube.com/watch?v=aEK-kk6-wlU

Podcast Contact Information:

Website: www.learnit.com

Email: [email protected]

Follow us on LinkedIn and Instagram for updates.

AI 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:

1. Why the strongest AI leaders are not obsessing over every new tool, but are instead leading with confidence, empathy, vulnerability, and clarity through constant change
2. Why 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 processes
3. Why framing AI around tasks, workflows, and outcomes reduces fear better than telling people they need to reinvent their entire job
4. How 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 teams
5. Why employer expectations, customer expectations, and employee expectations have all gone up, and why Danielle believes people who refuse to lean in risk getting left behind
6. Why 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 upskilling

Timestamps

• 00:00 - Episode preview and introduction
• 02:58 - The tech is ready, the humans aren’t
• 04:24 - What thriving leaders are doing that frustrated leaders aren’t
• 07:50 - 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 human
• 11:48 - How eBay got 9,000 employees to lean into AI
• 14:54 - The two expectations leaders now have that change everything
• 16:57 - What to do when executives want roi faster than people can adapt
• 22:29 - How to use AI in hiring without losing the human judgment
• 27:14 - Why AI coaching may help people ask for support they’d never ask a human for
• 30:41 - Danielle’s surprising take on ChatGPT vs Gemini for giving feedback
• 35:53 - The real risk of AI fatigue and how to avoid it
• 37:50 - Why learning and development suddenly has a bigger seat at the table
• 40:40 - What C-suites actually want to hear from L&D right now
• 43:02 - Why grace and psychological safety matter more than perfection
• 46:48 - What will still be fundamentally human five years from now
• 48:39 - Damon’s closing challenge for leaders navigating AI change

About Danielle Clark

Danielle 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 Mentions

Danielle Clark’s LinkedIn: https://www.linkedin.com/in/danielle-clark-sf/

Learn-It-All Press: Book a discovery call at www.learnitallpress.com

Podcast Contact Information:

Website: www.learnit.com

Email: [email protected]

Follow us on LinkedIn and Instagram for updates.

Why 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:

1. Why achieving your biggest goals can still leave you empty if your life is built around outcomes instead of meaning
2. Jim Murphy’s “PALMS” framework: possessions, achievements, looks, money, and status, and why so many people chase them, hoping they’ll finally feel loved and enough
3. What the A.J. Brown moment revealed about sudden visibility, success, and why external validation still doesn’t create lasting fulfillment
4. Why impostor syndrome is often a self-centered fear loop of “What do they think of me?” and how humility helps break it
5. How top performers develop courage by becoming willing to feel embarrassment, uncertainty, failure, and discomfort
6. The crucial difference between confidence and belief
7. How to stop treating life like a series of transactions and start building one with purpose, presence, courage, and peace

Timestamps:

• 00:00 Episode preview and introduction
• 01:15 The core of inner excellence: learning and growing every day
• 03:56 The question that shaped Jim’s life: how to stay calm under pressure
• 06:45 What it really means to feel fully alive
• 08:55 What to do when life feels like pure suffering
• 09:07 The “PALMS” trap: possessions, achievements, looks, money, and status
• 11:04 Impostor syndrome and how humility dissolves it
• 12:29 Happiness vs. joy and why most people chase the wrong one
• 13:44 Why ego is the biggest blocker to extraordinary performance
• 15:06 Why “the best possible life” matters more than performance alone
• 17:10 The Michael Phelps principle and accurate self-awareness
• 21:17 How Jim coaches clients: WTF, DWTF, and lifestyle design
• 23:24 The one trait elite performers all seem to have
• 26:34 What being fully present actually means
• 28:02 The two-minute presence practice
• 29:14 Why you can’t be grateful and anxious at the same time
• 30:18 The Float Up Tool and getting out of mental transactions
• 31:27 Damon’s phone reminder trick for becoming more present
• 32:15 How to help kids become mentally tough
• 33:14 Why belief matters more than confidence
• 34:09 The golf story that changes how you think about good and bad outcomes
• 37:45 Jim on ego, fame, and wanting everyone to think he was the best
• 39:48 The two turning points that changed Jim’s life
• 40:50 Jim’s reaction when the A.J. Brown moment exploded
• 42:56 Jim’s new book The Best Possible Life
• 45:10 What makes Inner Excellence different from sports psychology
• 46:37 AI, unlearning, and adapting to the future of work
• 47:36 Damon’s closing challenge on gratitude, comparison, and serving others
• 48:06 Where to connect with Jim

About Jim Murphy

Jim 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 Mentions

Inner Excellence: Train Your Mind for Extraordinary Performance and the Best Possible Life: https://www.amazon.com/INNER-EXCELLENCE-Extraordinary-Performance-Possible/dp/1734654805

The 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/1734654848

Jim Murphy’s LinkedIn: https://www.linkedin.com/in/innerexcellence/

Jim Murphy’s Instagram: https://www.instagram.com/innerexcellencejimmurphy/?hl=en

Jim 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.com

Email: [email protected]

Follow us on LinkedIn and Instagram for updates.

What 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 Learn

1. Why CJ got pushback for buying his clients cocktails — and how that moment revealed everything wrong with the system he was in
2. The difference between a financial professional who’s technically sharp and one who’s actually right for you
3. Why you don’t need a lot of money to benefit from a great advisor — you need a goal you’re not confident executing alone
4. How CJ thinks about AI: not as a threat, but as the thing that finally frees advisors to do the human work that actually builds trust
5. Why he tells aspiring financial professionals to major in psychology and minor in finance
6. What “doing the right thing when no one is looking” looks like inside a company built around it

Chapters

• 00:00 Episode preview and introduction
• 00:54 What CJ Davidson saw inside traditional financial services
• 03:48 The “art and science” of financial advice
• 05:14 The client mixer idea that challenged the old playbook
• 09:27 Moving from advisor to leadership and teaching fiduciary thinking
• 11:41 Seeing how “the soup was made” inside corporate finance
• 14:33 Why CJ helped build Proxy Financial
• 16:22 How to test a business hypothesis before going all in
• 17:50 Building a mission-aligned culture on a distributed team
• 19:03 How to choose a financial advisor who is actually the right fit
• 25:26 Proxy Financial’s long-term vision and advisor succession
• 28:06 Ethics, temptation, and doing the right thing when no one is looking
• 30:25 How AI is changing financial advice without replacing human trust
• 33:45 Where listeners can connect with CJ Davidson
• 35:33 CJ’s take on confidence vs. arrogance

About CJ Davidson

CJ 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 Mentions

CJ 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/0593418573

Podcast Contact Information:

Website: www.learnit.com

Email: [email protected]

Follow us on LinkedIn and Instagram for updates.

What 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 place
• How 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 move
• The difference between confidence and arrogance, and why Vincent says failure taught him more than books, podcasts, and “pocket MBAs” ever did
• Why empathy, politics, decisiveness, and relationship-building are still the real human advantage in an AI world
• Why mentorship is everything, and why real leaders should see developing people as part of their legacy

Timestamps

• 00:00 Episode preview
• 00:42 The first question to ask before saying yes to leadership
• 02:29 Why leadership is not for everybody
• 04:59 What to do if you have already accepted the wrong leadership role
• 08:04 Vincent Wanga’s improbable path into creativity and leadership
• 10:02 Getting kicked out of school and rebuilding from scratch
• 12:24 What to do after losing your dream job
• 15:31 Delusional optimism, entrepreneurship, and betting on yourself
• 19:06 The branding project that humbled Vincent’s ego
• 25:17 Scaling a team 20x and the leadership lesson that stayed with him
• 31:03 Why Vincent wrote The Art of Direction
• 35:36 Gen Z, alternate paths, and redefining leadership
• 37:16 The human skills that matter most in the AI era
• 42:08 How leaders should handle executive pushback and boardroom politics
• 47:24 AI as a tool, not a crutch
• 53:13 Why mentorship is everything
• 58:24 What leadership could look like 20 years from now
• 01:01:22 Where to connect with Vincent Wanga

About Vincent Wanga

Vincent 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 Mentions

The Art of Direction: Personal Perspectives on the Path to Creative Leadership: https://www.amazon.com/Art-Direction-Personal-Perspectives-Leadership/dp/B0DXJ4MLG7

Vincent 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/0066620996

The 7 Habits of Highly Effective People by Stephen R. Covey: https://www.amazon.com/Habits-Highly-Effective-People-Powerful/dp/0743269519

Podcast Contact Information:

Website: www.learnit.com

Email: [email protected]

Follow us on LinkedIn and Instagram for updates.

What 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:

1. Why Ray Lane says people leave for context and get recruited away for content, and what that means for retaining top performers
2. What IBM taught him about discipline, structure, and leadership development, and what EDS taught him that IBM never could
3. Why Ross Perot’s interview style forced Ray to stop hiding behind company credentials and explain why he was the right person
4. What Oracle looked like when Ray joined, why customers had lost confidence, and how bad the mess really was behind the scenes
5. How Ray rewrote Oracle’s sales rules, ripped up bad customer contracts, and moved the company away from short-term wins that destroyed long-term trust
6. The difference between a diminisher and a multiplier, and why Ray believes leaders should inspire people, not shrink them
7. Why most founders are not automatically entrepreneurs, and most entrepreneurs are not automatically CEOs
8. What Ray looks for in a startup pitch, including why a founder should be able to explain the problem and opportunity in 30 seconds

Timestamps

• [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 back

About Ray Lane

Ray 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 Mentions

Ray 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/0451163532

Multipliers book by Liz Wiseman: https://www.amazon.com/Multipliers-Best-Leaders-Everyone-Smarter/dp/0061964395

Podcast Contact Information:

Website: www.learnit.com

Email: [email protected]

Follow us on LinkedIn and Instagram for updates.

What 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:

1. What Damon believes parents and coaches get wrong when they make excuses instead of helping kids grow through setbacks
2. The story of not making a youth soccer team and the tough-love lesson Damon’s dad gave him that stayed with him forever
3. How Damon rebounded after striking out four times in one game at Arizona State, and what his coach said that restored his confidence
4. Why Little League is not really about winning or losing, but about showing up, giving your best, being a good teammate, and having fun
5. How youth sports help kids develop the confidence, discipline, and courage they’ll later need in leadership, business, and life

Timestamps

• 00:00 – Opening memories of Little League and the joy of getting ready for the season
• 01:15 – Damon’s salute to parents and coaches who make youth sports possible
• 01:47 – The lifelong skills kids learn through sports, from teamwork to discipline
• 02:09 – Why parents and coaches need to let kids fail instead of bubble wrapping them
• 02:28 – Damon’s story of not making the soccer team and the lesson his dad taught him
• 03:18 – Striking out four times against Michigan and what happened the next day
• 04:21 – Why sports gave Damon the courage to lead teams and work with thousands of leaders
• 04:43 – What Little League is really about, and why winning is not the point
• 05:38 – Damon’s message to parents about support, perspective, and having a great season
• 06:00 – Closing thoughts and who this episode should be shared with

About Damon Lembi

Damon 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/FTZRCJB

Coach Steve Knudsen: https://www.facebook.com/steve.knudsen.9?mibextid=wwXIfr

Podcast Contact Information:

Website: www.learnit.com

Email: [email protected]

Follow us on LinkedIn and Instagram for updates.

What 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:

1. Why Warren Buffett’s question became the mindset shift Jim needed when he was tempted to fall into a victim mentality at Blockbuster.
2. 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.
3. 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.
4. 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.
5. 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.
6. 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 Keyes

About Jim Keyes

Jim 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 Mentions

Education is Freedom book: https://www.amazon.com/Education-Freedom-Future-Your-Hands/dp/1637588003

Jim 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/@jkeyesauthor

Harvard Business School Case on Blockbuster, Netflix, and Redbox: https://hbsp.harvard.edu/product/KEL616-PDF-ENG

The Learn-It-All™ Podcast: The Ask Approach with Jeff Wetzler: https://www.youtube.com/watch?v=FmuBcUBlvOk

Podcast Contact Information:

Website: www.learnit.com

Email: [email protected]

Follow us on LinkedIn and Instagram for updates.