the Learn-It-All™ podcast

Are you letting fear of discomfort hold you back from your next massive career breakthrough?

In this episode of The Learn-It-All™ Podcast, Damon sits down with D1 swim team captain, model, and MBA candidate Andreea Dragoi to discuss how elite athletic training builds a high-performance mindset that business schools simply cannot replicate. Andreea dives deep into how her upbringing in Romania fueled her relentless, fearless drive to think outside the box, try new things, and never take "no" for an answer.

Together, Damon and Andreea unpack why high-performance habits like waking up at 5:30 AM to dive into a cold pool translate into invaluable business assets. Andreea shares practical mental strategies for overcoming imposter syndrome as a young leader, blocking out the superficial "noise" of social media, and learning to "focus on your lane" to ensure long-term success.

If you are looking to build learning agility, break out of your comfort zone, or understand how to lead highly ambitious team members, this episode will provide the ultimate playbook for athletic discipline and professional growth.

📘 Get a FREE copy of The Learn-It-All Leader Book: https://dl.bookfunnel.com/3ingcx2pp5

In this episode, you’ll learn...

1. Why doing what makes you uncomfortable can open doors that staying safe never will.
2. How to train your mind to “enjoy the pain” and push past the psychological barriers that tell you to stop.
3. Why being coachable means accepting feedback you may not want to hear and actually applying it.
4. How ambitious people can lose their edge when life gets too comfortable, and how to reconnect with the reason you started.
5. Why confidence comes from repeatedly putting yourself in situations that scare you, not waiting until you feel ready.
6. How to stay focused on your own lane when social media makes everyone else’s life look perfect.

Timestamps

• 00:00 Episode preview and introduction
• 00:57 The fearless mindset behind Andreea Dragoi’s success
• 02:23 The two people who shaped her drive
• 03:16 Moving to America alone at 18
• 05:28 What American culture could learn from Romania
• 08:12 The brutal discipline of a D1 swimmer
• 09:04 How to become 1% better every day
• 11:26 The difference between learn-it-alls and know-it-alls
• 13:31 The race she lost before it even ended
• 15:50 Turning rejection into your next opportunity
• 17:12 How sports built her confidence beyond the pool
• 18:03 Two tricks for performing under pressure
• 19:49 How an introvert learned to own the room
• 20:55 Why companies keep hiring former athletes
• 22:44 What ambitious young employees need from leaders
• 23:35 The leadership style that kills motivation
• 25:14 How Andreea uses AI to work smarter
• 29:54 Why everyone needs to learn how to sell
• 30:27 Advice for an eight-year-old with big dreams
• 31:19 The truth about imposter syndrome
• 32:15 Why we care so much about other people’s opinions
• 33:00 The social media reality nobody wants to admit
• 34:20 The hunger that keeps high performers moving
• 35:35 Damon’s challenge: Get uncomfortable and take the risk

About Andreea Dragoi

Andreea Dragoi is a Division 1 varsity swimmer and captain at San Jose State University, currently completing her accelerated MBA program. Born and raised in Romania, Andreea moved to California at the age of 18 to pursue both her academic and athletic passions. In addition to her athletic achievements, Andreea has successfully navigated roles in modeling and pageantry. She is a passionate advocate for learning agility, leveraging artificial intelligence in marketing, and encouraging the next generation of leaders to push past their comfort zones.

Resources and Mentions

Andreea Dragoi’s LinkedIn: https://www.linkedin.com/in/andreea-dragoi-270377235/

Andreea Dragoi’s Instagram: https://www.instagram.com/dragoi_andreea/?hl=en

Andreea Dragoi’s Website: https://andreeadragoi.com/

Podcast Contact Information:

Website: www.learnit.com

Email: [email protected]

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Getting stuck at $2 or $3 million isn't a market problem. It's a blind spot problem.

Bryan Clayton, founder of GreenPal, escaped the trap so many founders fall into — becoming the biggest obstacle to their own growth — and scaled his first company past $10M.

In this episode, you will learn:

• What helped Bryan break through a years-long plateau in the business
• The hiring mistake that cost him years
• How to get brutally honest feedback on demand.

His story will help you stop being the bottleneck and turn AI into your biggest advantage.

Topics discussed:

(00:00) Introduction

(00:39) Constructive Dissatisfaction

(01:51) The Hidden Blind Spot

(03:03) Know-It-All vs. Learn-It-All

(06:45) Start Here With AI

(09:47) Breaking The $3M Plateau

(11:57) The Hiring Mistake That Cost Years

(14:03) Why You Hate Your Culture

(15:52) Resisting Feedback

(20:21) Ask AI to Roast You

(23:35) Selling The Business

(26:21) Life After The Exit

(29:59) Starting Over At Zero

(33:01) 3 Things to Do in the Early Days

(36:16) Finding A Blue Ocean

(41:11) Going Into New Markets

(43:50) The Road To A Million

(45:44) Advice For Stuck Founders

Connect with Bryan Clayton:

• https://www.yourgreenpal.com/
• https://www.instagram.com/bryanmclayton/
• https://www.linkedin.com/in/bryan-clayton-a96b33214/

Resources Mentioned:

• 𝘉𝘶𝘪𝘭𝘵 𝘵𝘰 𝘚𝘦𝘭𝘭: 𝘊𝘳𝘦𝘢𝘵𝘪𝘯𝘨 𝘢 𝘉𝘶𝘴𝘪𝘯𝘦𝘴𝘴 𝘛𝘩𝘢𝘵 𝘊𝘢𝘯 𝘛𝘩𝘳𝘪𝘷𝘦 𝘞𝘪𝘵𝘩𝘰𝘶𝘵 𝘠𝘰𝘶 by John Warrillow
• 𝘌𝘹𝘵𝘳𝘦𝘮𝘦 𝘖𝘸𝘯𝘦𝘳𝘴𝘩𝘪𝘱: 𝘏𝘰𝘸 𝘜.𝘚. 𝘕𝘢𝘷𝘺 𝘚𝘌𝘈𝘓𝘴 𝘓𝘦𝘢𝘥 𝘢𝘯𝘥 𝘞𝘪𝘯 by Jocko Willink
• 𝘉𝘭𝘶𝘦 𝘖𝘤𝘦𝘢𝘯 𝘚𝘵𝘳𝘢𝘵𝘦𝘨𝘺 by Renée Mauborgne and W. Chan Kim

About the Guest:

Bryan Clayton started mowing lawns as a teenager with a push mower. Twenty years later, he’s the CEO of GreenPal — the app Entrepreneur Magazine calls the Uber for lawn care.

Before GreenPal, Bryan built one of Tennessee’s largest landscaping companies growing it to over $10 million a year before selling it.

Now he’s doing it again — this time with technology. GreenPal connects 300,000 homeowners with reliable lawn pros, handling thousands of jobs every day all over the US.

Bryan’s on a mission to bring AI into one of the oldest industries out there — helping small lawn care businesses use data and automation to compete like big companies.

From pushing a mower to building a $30 million tech platform, Bryan’s story is all about grit, adaptation, and how old-school hard work can thrive in a high-tech world.

Great leaders aren't born. They're always in the making.

New episodes of The Learn-It-All Podcast with Damon Lembi every week.

📘 Get a free copy of The Learn-It-All Leader: https://dl.bookfunnel.com/3ingcx2pp5

Subscribe on YouTube: https://www.youtube.com/@TheLearnItAllPodcast?sub_confirmation=1

Upskill yourself and your team with Learnit: https://www.learnit.com

Follow Damon Lembi:

• LinkedIn: https://www.linkedin.com/in/damonlembi
• Instagram: https://www.instagram.com/damonlembi

This episode was produced by Podcast Boutique https://www.podcastboutique.com

#LearnItAll #DamonLembi #Leadership #LeadershipPodcast

What do you do when you are the youngest, least experienced person in the room, but you are still asked to lead? It is a terrifying reality that many young leaders and entrepreneurs face early in their careers. The instinct is to jump in and prove you have everything under control, but true leadership requires a completely different approach.

In this episode of The Learn-It-All™ Podcast, Damon sits down with leadership expert, professor, and former nuclear submarine officer Jon Rennie to break down how to successfully lead people who know more than you.

Drawing from his high-stakes military background on a nuclear submarine and his experience running eight manufacturing companies, Jon shares why the ultimate answer to your team's problems already exists within the four walls of your organization, if you are humble enough to look for it. Jon and Damon discuss how to break down corporate silos by getting out of the corner office, why you must establish high relational trust to survive a crisis, and how to practically lead just like playing chess or the guitar.

Whether you are a corporate executive trying to cut through the management filter or a solo entrepreneur hiring your very first employees, this conversation provides an actionable roadmap to shifting your perspective from being a "non-useful body" to a highly respected, resilient leader.

📘 Get a FREE copy of The Learn-It-All Leader Book: https://dl.bookfunnel.com/3ingcx2pp5

In this episode, you’ll learn...

1. Why the best way to earn respect when your entire team is older and more experienced than you is to remain present, observe carefully, and get up to speed quickly so you don't become a liability.
2. How to eliminate "us vs. them" mentalities between salary and hourly workers by forcing managers to work side-by-side on the shop floor to face reality and see the true root causes of operational problems.
3. Why senior leaders must resist the urge to immediately hand over answers, and instead use coaching questions to let employees struggle, learn through failure, and build authentic ownership.
4. Why building deep, authentic relationships during normal times gives leaders the leverage and leeway they need to keep their teams motivated and unified when unexpected disruptions hit.
5. Lessons from the Navy submarine community on creating an onboarding culture of positive peer pressure and strict accountability where every single person actively adds value to the mission.

Timestamps

• 0:00 Introduction
• 0:55 What to do when your team knows more than you
• 2:04 How young leaders earn respect fast
• 3:38 Why proving yourself can backfire
• 5:46 The “us vs. them” culture hiding in your business
• 6:54 Fridays on the Floor: the habit that changed everything
• 9:28 The management mistake that keeps problems hidden
• 11:45 How to get honest ideas from the front line
• 14:57 Respect is not soft leadership
• 16:55 The union story that did not end perfectly
• 18:21 What corporate leadership misses that submarines get right
• 20:43 Why nobody wants to be a NUB
• 23:36 Leadership is learned by doing, not reading
• 24:36 How to let future leaders fail safely
• 28:14 What changed most in Jon’s leadership style
• 30:03 The danger of becoming a know-it-all
• 31:28 How great leaders find signal in the noise
• 34:30 Why hard times build another gear
• 35:57 What resilient leaders actually do in a crisis
• 38:10 The fastest way to start rebuilding trust
• 40:49 Why fake plastic leaders lose the room
• 41:37 What younger leaders understand about BS
• 44:27 If your team goes quiet, pay attention
• 45:13 The future needs leaders who can handle messy people
• 46:57 Where to connect with Jon Rennie
• 47:36 Damon’s challenge: listen, learn, lead

About Jon Rennie

Jon is a former U.S. Navy submarine officer who later led eight manufacturing businesses for three global companies over a 22-year corporate career. In 2016, he founded AccuGrid Technologies, a manufacturing company serving the electric utility industry, and now serves in a strategic leadership role. Jon teaches business and leadership at Thales College and hosts the globally ranked Deep Leadership podcast, which sits in the top 1.5% worldwide.

Resources and Mentions

You Have To Watch book: https://www.amazon.com/You-Have-Watch-Journal-Following/dp/B09XJFFJ6H

All in the Same Boat book: https://www.amazon.com/All-Same-Boat-Organization-Submariner/dp/B0942FWMKK

Jon Rennie’s LinkedIn: https://www.linkedin.com/in/jonscottrennie/

Jon Rennie’s YouTube: https://www.youtube.com/@DeepLeadershipPodcast

Jon Rennie’s Instagram: https://www.instagram.com/jonsrennie/

Jon Rennie’s X: https://x.com/jonsrennie

Podcast Contact Information:

Website: www.learnit.com

Email: [email protected]

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Everyone says they're "adopting AI"—but the bills are landing and no one's sure what tokens, logins, or dashboards actually prove. The harder truth: most "AI failures" are human ones in disguise.

In this episode of the Learn-It-All™ podcast, Damon Lembi kicks off a new monthly series with Learnit's Chief AI Learning Officer, Christa Hill. In a rapid-fire "agree or disagree" format, they go six rounds on the questions every leader is stuck on.

🚀 Get your team into the top 3% of AI users in North America in about four weeks with Learnit's AI Kickstarter: https://www.learnit.com/lp/ai-skills-program

In this episode, you'll learn:

• Why token usage is the wrong first metric to measure
• The hidden cost of the marathon chat session
• Why "show, don't tell" hackathons beat login counts for tracking real adoption.
• How to answer the "what's in it for me?" question that stalls adoption in management
• And much more!

Timestamps:

• 00:00 - Introduction: a new monthly series with Christa Hill
• 01:08 - Round 1: Is token usage the right adoption metric?
• 02:00 - Should you track logins and sessions instead?
• 03:17 - Why long chat sessions quietly burn tokens
• 03:56 - Hackathons and "show, don't tell"
• 05:13 - Round 2: Is "just adopt AI" a strategy?
• 06:10 - Raise the literacy floor first
• 07:28 - Why leaders must model the behavior
• 08:52 - Answering "what's in it for me?"
• 11:03 - Ask your AI what it can't do in your job
• 13:00 - The non-binding social contract
• 15:17 - Round 3: If I keep failing, am I doing it wrong?
• 16:23 - The Jenga test for working at the edge
• 17:34 - Does AI stifle critical thinking, or sharpen it?
• 18:18 - The $18,000 mistake and who's at fault
• 21:21 - You own what AI produces
• 23:00 - Christa's Easter-egg swear jar
• 23:30 - Round 4: Do you meet people where they are?
• 24:53 - Christa's honest take on adoption fatigue
• 28:40 - Timeboxing and stacking small wins
• 29:54 - Why there's no finish line
• 30:23 - Round 5: Are the jobs coming back?
• 32:07 - Why the comeback jobs look different
• 32:57 - White Castle and the plumber that fooled Mom
• 35:13 - Round 6: AI adoption or better work?
• 36:51 - Rethinking performance reviews
• 38:08 - Smash or Pass: the tools lightning round
• 38:42 - Claude Cowork (smash)
• 39:26 - Copilot's surprise 10-out-of-10
• 41:47 - Canva (pass, for now)
• 42:49 - Gamma and the death of the fancy deck
• 44:00 - Wispr Flow (smash): throw away your keyboard
• 45:39 - Christa's final challenge: think bigger
• 46:26 - Damon's closing: adoption starts with you

About Christa Hill:

Christa Hill is the Chief AI Learning Officer at Learnit, where she leads the AI Kickstarter program and teaches AI literacy to leaders and teams. She's in live classrooms most of the week, helping organizations move from first exposure to real adoption—and helping leaders navigate the human side of change: fear, resistance, and "what's in it for me?"

Resources and Mentions:

• Soren Kaplan's Inc. article: https://www.inc.com/soren-kaplan/half-of-ai-job-cuts-will-be-reversed-by-2027-gartner-says-heres-the-real-lesson/91361788
• Learnit AI Kickstarter program: https://www.learnit.com/lp/ai-skills-program
• Wispr Flow (voice-to-text): https://wisprflow.ai
• Claude & Claude Cowork: https://claude.ai
• Microsoft Copilot: https://copilot.microsoft.com
• ChatGPT: https://chatgpt.com
• Canva: https://www.canva.com
• Gamma: https://gamma.app

Great leaders aren't born. They're always in the making.

New episodes of the Learn-It-All™ podcast with Damon Lembi every week.

📘 Get a FREE copy of The Learn-It-All Leader Book: https://dl.bookfunnel.com/3ingcx2pp5

Subscribe on YouTube: https://www.youtube.com/@TheLearnItAllPodcast?sub_confirmation=1

Upskill yourself and your team with Learnit: https://www.learnit.com

Follow Damon Lembi:

• LinkedIn: https://www.linkedin.com/in/damonlembi
• Instagram: https://www.instagram.com/damonlembi

Are your employees silently resisting your latest technology mandates, or are you accidentally destroying trust by throwing down executive edicts?

In this episode of The Learn-It-All™ Podcast, Damon sits down with executive coach and change management expert Sue Bethanis to unpack why the AI economy demands a massive shift from traditional "change management" to high-empathy leadership. For 30 years, Sue has helped executive teams navigate monumental shifts, from the .com bust and the Great Recession to COVID-19 and now generative AI. She reveals why simply commanding workers to adopt tools like ChatGPT or Claude creates widespread anxiety and stalling, and explains why true productivity takes time, experimentation, and psychological safety.

Damon and Sue dive deep into what sets human leadership apart in a world where anyone can access the same data with the push of a button. You’ll discover how to move your team from functional users to fluent innovators by sharpening human-centric skills like taste, discernment, creative judgment, and deep design thinking.

Whether you are a risk-averse senior leader trying to protect your organization or a change agent pushing for rapid iteration, this conversation delivers actionable coaching frameworks to replace workplace tension with curiosity, grace, and meaningful connection.

📘 Get a FREE copy of The Learn-It-All Leader Book: https://dl.bookfunnel.com/3ingcx2pp5

In this episode, you’ll learn...

1. Why the AI era is uniquely threatening to knowledge workers
2. Why sending top-down corporate mandates fails miserably, and how leaders can put on a coaching hat to physically sit with team members, practice empathetic listening, and lower adoption anxieties.
3. How to step away from rigid timelines and instead iterate with your employees by identifying real pain points, engaging in rapid prototyping, and fostering a culture that celebrates "failing fast".
4. Why true innovation means shifting focus away from the repetitive "making" process and spending your energy on developing a unique market perspective and creative vision.
5. A 3-step physical reset to prevent corporate blowouts
6. Why it is completely okay if you aren't seeing massive, instantaneous productivity spikes a year into deployment, and how viewing the tool as a partner on a "tandem bike" helps build sustainable, long-term velocity.

Timestamps

• 00:00 Episode preview and introduction
• 01:19 Why AI feels different from every past disruption
• 02:53 The hidden pattern behind every major change
• 03:58 Why leaders accidentally make resistance worse
• 05:02 The shift from driving change to inspiring it
• 06:42 Why empathy is now a leadership skill
• 08:40 The trust problem slowing AI adoption
• 10:15 Where leaders should actually start with AI
• 12:07 Why “fail fast” needs more grace
• 13:29 The Slack message that exposed AI fear
• 15:01 The ROI mistake companies keep making
• 16:53 Why humans are still responsible for AI output
• 18:16 The real skill that separates people in the AI economy
• 20:55 The sand pile lesson for unpredictable change
• 23:16 What leaders can learn from a late-night parenting moment
• 26:39 The question that buys leaders time
• 27:34 How to repair trust after losing your cool
• 29:08 What sports teach leaders about pressure
• 31:08 Balancing intensity with empathy
• 34:52 Why critical thinking has become non-negotiable
• 36:26 How AI can help you influence upward
• 38:59 Why audience context changes every decision
• 40:09 The difference between AI advice and human coaching
• 43:22 Why the best leaders still ask for coaching
• 45:29 Where to connect with Sue Bethanis
• 46:09 Damon’s challenge to every leader using AI

About Sue Bethanis

Sue Bethanis is the Founder and CEO of Mariposa Leadership, an elite executive coaching and leadership development firm celebrating its 30th anniversary. For three decades, Sue has coached top-tier executives at iconic Silicon Valley tech companies, including Apple, Yahoo, Pinterest, and Amazon, guiding them through massive economic and technological disruptions. Alongside tech veteran Ethan Evans, she co-teaches the highly acclaimed Maven course, "Cracking the C-Suite in the AI Economy," where she trains senior leaders to scale corporate culture, build executive presence, and act as strategic change agents.

Resources and Mentions

Sue Bethanis’ LinkedIn: https://www.linkedin.com/in/suebethanis/

Mariposa Leadership website: https://mariposaleadership.com/

From Resistance to Resilience: Our Roles as Change Agents in AI Adoption: https://levelupwithethanevans.substack.com/p/from-resistance-to-resilience-our

Cracking the C-Suite in the AI Economy: https://maven.com/ethan-evans/cracking-the-c-suite

Podcast Contact Information:

Website: www.learnit.com

Email: [email protected]

Subscribe to the Learn-It-All Podcast: Youtube I Apple I Spotify

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Are you working incredibly hard but still feel like something is missing? In an era of AI integration, market volatility, and relentless global economic issues, it’s easy to default to a head-down hustle mentality. But the truth is, you can’t outwork velocity.

In this episode of The Learn-It-All™ Podcast, Damon sits down with executive coach and author Angus Nelson to reveal why the single most expensive bottleneck in any business today isn't weak strategy or broken systems, it's a disregulated nervous system. If your inner operating system is running on scarcity, control, and fear, your decision-making stalls, brain fog rolls in, and talent hemorrhages. Angus shares how high performers can shift their framing from external accolades back to internal sovereignty and personal power.

Tune in to discover how to bridge the knowledge-action gap, transform your psychology from a victim mentality into full agency, and learn a practical blueprint to stop white-knuckling your way through life so you can finally remember "who the f*** you are."

📘 Get a FREE copy of The Learn-It-All Leader Book: https://dl.bookfunnel.com/3ingcx2pp5

In this episode, you’ll learn...

1. How to identify a disregulated nervous system in corporate leadership through micro-moments, like snapping at a spilled coffee or offloading self-trust onto consultants and advisers.
2. The dangers of "people-pleasing" and micromanagement behaviors, revealing how stepping into a situation to "help" is often just a guise for a leader trying to enforce control out of fear.
3. The secret to becoming the most powerful person in any room by adopting a psychological framework of nothingness: having nothing to gain, nothing to prove, and nothing to lose.
4. The mechanics of the C³ Protocol: Clarity, Capacity, and Composure, and how moving through these three pillars allows leaders to stop reacting blindly to chaos and start moving with swiftness and auditing their own behavior.
5. How to execute a 10-Minute Revolution using a daily sequence of affirmation, identity work, and concrete choices to pull your idealized future self directly into your current day-to-day actions.
6. The power of the "Spice Girl Principle" in coaching to cut through what leaders don't want, forcing absolute honesty regarding their true desires and personal destinations.

Timestamps

• 00:00 - Introduction
• 01:06 - Why high performers still feel stuck
• 02:42 - The tiny signs your nervous system is running the show
• 04:01 - When “helping” becomes control
• 05:19 - What resilience actually means under pressure
• 09:30 - When AI makes people question their value
• 10:43 - The dangerous phrase leaders can’t afford anymore
• 13:38 - The $72,000 failure that changed Angus’ life
• 17:32 - Why great coaching requires telling the truth
• 20:52 - What happens when leaders finally give themselves permission
• 33:11 - Why the inner critic is not actually the enemy
• 35:29 - Damon’s honest fear as a business owner
• 38:04 - The Spice Girl principle for getting honest
• 39:50 - What human success really means
• 41:35 - How stable leaders become magnetic
• 47:45 - The leaders who changed what people believed was possible
• 50:13 - Three signs you need a nervous system upgrade
• 55:07 - The 10-minute revolution
• 58:59 - How to walk like the person you’re becoming
• 1:02:34 - What Angus hopes readers say one year later
• 1:04:08 - Where to get Neuro-Resilient Leader book
• 1:05:50 - Damon’s final challenge to listeners

About Angus Nelson

Angus Nelson is the author of Neuro-Resilient Leader and the founder of Evolve Leadership. He helps entrepreneurs and high-performing leaders install Leadership Stability, the ability to make clear, high-stakes decisions without burnout by recalibrating the nervous system. He has advised executives at Cisco, FedEx, and Workday and shares his C³ Protocol: Clarity, Capacity, and Composure, with leaders navigating pressure, uncertainty, and rapid change.

Resources and Mentions

Neuro-Resilient Leader book: https://www.amazon.com/Neuro-Resilient-Leader-Internal-Operating/dp/1636988792

Angus Nelson’s LinkedIn: https://www.linkedin.com/in/angusnelson/

Angus Nelson’s Website: https://angusnelson.com/

Angus Nelson’s YouTube: https://www.youtube.com/@coachangusnelson

10 Minute Leaders: https://angusnelson.com/10-minute-leaders

Evolve Leadership Podcast: https://podcasts.apple.com/us/podcast/evolve-leadership/id1040543696

Podcast Contact Information:

Website: www.learnit.com

Email: [email protected]

Subscribe to the Learn-It-All Podcast: Youtube I Apple I Spotify

Follow Damon Lembi: Linkedin I Instagram I Facebook I X

Are you getting on planes you don't actually need to be on? It is easy to confuse your corporate role with your personal identity, especially when you are a high performer consistently hitting the president's club. But what is the hidden cost of chasing that next title, bigger team, or salary increase?

In this episode of The Learn-It-All™ Podcast, Damon sits down with Strategic Advisor, Author, and Top-Ranked Podcast Host Billy Keels to discuss what happens when your identity gets completely wrapped up in your corporate lifestyle. Billy shares his personal wake-up call from October 2012, when he found himself boarding a flight for an executive meeting in Germany on his son's third birthday, physically feeling sick because he was far away from the people he wanted to be with. He dives deep into the corporate "busy-ness" that keeps high achievers frantic and explains why every corporate relationship eventually ends.

If you are a high-earning corporate executive trying to figure out how to stop being just a corporate number, manage the chaos of a side business, and gain control of your calendar, this conversation provides a strategic roadmap to designing a life where your job becomes completely optional.

📘 Get a FREE copy of The Learn-It-All Leader Book: https://dl.bookfunnel.com/3ingcx2pp5

In this episode, you’ll learn...

1. Why Billy’s flight on his son’s third birthday exposed the hidden cost of tying your identity to your corporate role
2. How high performers can separate their title from their values before the next promotion, paycheck, or business trip starts making decisions for them
3. Why “spending time” with family is not the same as “investing time,” and how intentional presence changes the way leaders show up at home
4. How to calculate your optionality number so your job becomes a choice instead of a financial dependency
5. Why every corporate relationship eventually ends, and how to build a backstop before layoffs, leadership changes, or personal crises force your hand
6. How Billy helps executives reclaim time, structure a side business, and stay successful at work without sacrificing the life they say matters most

Timestamps

• 00:00 - Introduction
• 00:53 - The birthday flight that changed Billy’s life
• 02:27 - When the plane took off and his heart sank
• 06:21 - Why high achievers keep choosing the job
• 07:32 - When your title becomes who you are
• 10:15 - The three-part clarity framework
• 11:47 - Spending time vs. investing time
• 13:28 - Finding your optionality number
• 19:09 - Why high achievers struggle to ask for help
• 20:41 - The scary part of finally opening up
• 23:38 - Moving out of victim mentality
• 26:57 - Are you just a corporate number?
• 29:35 - Why companies protect themselves first
• 31:57 - How to build optionality while keeping your paycheck
• 34:34 - Do you really need to work those extra 15 hours?
• 36:21 - The path to making your role optional
• 37:26 - What money is actually for
• 39:00 - What truly high performers have in common
• 41:46 - Why successful executives reach out for help
• 43:14 - When a high income still does not feel like freedom
• 48:46 - How to define what “being present” actually means
• 50:55 - When real change starts to show up
• 54:34 - The two types of executives Billy helps most
• 56:45 - Why podcasting can change your life and brand
• 01:00:16 - How podcasting built Billy’s confidence and network
• 01:04:21 - The fatherhood practice Billy is most proud of
• 01:06:08 - Where to connect with Billy
• 01:08:02 - Damon’s challenge: Are you getting on planes you do not need to be on?

About Billy Keels

Billy Keels is a national best-selling author, host of the top 1.5% globally ranked “Going Long Podcast”, and expert/go-to executive coach for enterprise-level executives around the world. Based in Barcelona, Spain, Billy is an international speaker and elite advisor to ambitious C-level leaders looking to maximize their positions and opportunities while maintaining their existing career security and stability. Billy is on a mission to help high earning executives multiply their options for the future.

Resources and Mentions

Billy Keels’ website: https://www.billykeels.com/

Billy Keels’ LinkedIn: https://www.linkedin.com/in/billykeels/

The Going Long Podcast: https://www.billykeels.com/podcast

The Pathway to Optionality: https://www.makeitoptional.com/

Podcast Contact Information:

Website: www.learnit.com

Email: [email protected]

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Are you ready to transform your failures into your greatest competitive advantage?

In the high-stakes world of Major League Baseball, even the best players fail seven out of ten times. In this episode, Damon sits down with 30-year veteran sports journalist Ken Davidoff to discuss how the resilience learned on the diamond can be the ultimate blueprint for success in the boardroom and at home. Drawing from his book, 101 Lessons from the Dugout, Ken shares powerful stories of Hall of Famers and everyday leaders who mastered the art of "tagging up", pausing to control reactions before they spiral. Whether you are a first-time manager struggling with a "rough outing" or a parent trying to help your child navigate the pressures of youth sports, this conversation offers actionable strategies on building trust through "small ball," prioritizing under pressure with "fielder’s choice" logic, and leading with the authenticity of a World Series manager.

Stop playing "not to lose" and start learning how to pace yourself through the grind of any season.

📘 Get a FREE copy of The Learn-It-All Leader Book: https://dl.bookfunnel.com/3ingcx2pp5

In this episode, you’ll learn...

1. Why accepting failure, digesting it, and moving on is a prerequisite for both professional growth and mental strength.
2. Why taking a literal three-second pause before reacting to a frustrating email or a spilled glass of juice can prevent "volcano" moments and preserve your relationships.
3. Why you shouldn't always "swing for the fences" early on; instead, focus on being consistent, meeting people, and building a foundation of trust that allows you to take bigger risks later.
4. A simple mental framework for deciding where to "step on the gas" when your to-do list is overflowing or your child is struggling with multiple subjects.
5. Why the most revered leaders are defined not by their "scorecard" stats, but by their authenticity, curiosity, and how they treat everyone from the janitor to the CEO.
6. Why taking pride in your space and "cleaning up your own messes", literal or metaphorical, sets a standard that transcends winning or losing.

Timestamps

• 0:00 - Introduction
• 1:16 - Baseball’s brutal lesson about failure
• 2:31 - The dropped catch nobody forgot
• 4:23 - What leaders can learn from a bad outing
• 5:34 - When parents make youth sports harder
• 6:22 - How 101 Lessons from the Dugout began
• 8:50 - The hidden power of the on-deck circle
• 12:29 - What kids learn when they sit on the bench
• 14:43 - The Little League catch Ken still remembers
• 16:48 - The baseball rule that can stop your anger
• 19:43 - Why “small ball” built Ken’s career
• 21:49 - How one quiet story earned years of trust
• 24:55 - How to repair a damaged relationship
• 27:36 - David Wright’s lesson for struggling kids
• 29:37 - The World Series moment that proved chapter 92
• 32:13 - Why Don Mattingly is remembered without a ring
• 34:54 - The lesson Ken wishes made the book
• 37:39 - How fielder’s choice teaches priorities
• 41:00 - What great managers do differently
• 43:41 - The two lessons Ken hopes families actually use
• 44:15 - How parents can stop chasing wins through their kids
• 46:05 - Damon’s final challenge for coaches, parents, and leaders

About Ken Davidoff

Ken Davidoff is a renowned sports journalist who spent 30 years covering Major League Baseball for major outlets, including the New York Post. Throughout his career, he has interviewed thousands of players, managers, and agents, covering legendary teams and historic World Series matchups. Ken is currently an adjunct professor of journalism at a college in Massachusetts. He is the co-author of 101 Lessons from the Dugout: What Baseball and Softball Can Teach Us About the Game of Life, a book that translates the timeless wisdom of baseball and softball into life lessons for parents, children, and professionals.

Resources and Mentions

101 Lessons from the Dugout book: https://www.amazon.com/101-Lessons-Dugout-Baseball-Softball/dp/B0F7H3553S

Ken Davidoff’s LinkedIn: https://www.linkedin.com/in/ken-davidoff-220b7a4/

Ken Davidoff’s Instagram: https://www.instagram.com/kendavidoff/

Podcast Contact Information:

Website: www.learnit.com

Email: [email protected]

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What if the secret to elite leadership isn't a natural-born talent, but a learned skill forged through vulnerability and connection? Many emerging leaders struggle with imposter syndrome, questioning if they are "good enough" to lead more experienced peers or step into high-pressure roles.

In this episode of The Learn-It-All™ Podcast, Damon sits down with Kieran Read, former captain of the legendary New Zealand All Blacks, to discuss the transition from high-performing individual contributor to world-class leader. Kieran reveals why the most impactful leaders lead through authentic action rather than "big speeches," how to build trust by initiating care and connection first, and the importance of having the courage to be "uncomfortable" to achieve true growth.

Whether you are a first-time manager or a senior director, Kieran’s insights on "horizontal leadership" and empowering those around you will help you develop the confidence to lead your team toward excellence.

📘 Get a FREE copy of The Learn-It-All Leader Book: https://dl.bookfunnel.com/3ingcx2pp5

In this episode, you’ll learn...

1. Why trying to emulate a "movie version" of a leader often fails, and how sticking to your personal values and personality builds more trust and connection with your team.
2. How to build a foundation of care and connection through simple daily interactions like sitting with someone new at lunch, before attempting to hold people to high levels of accountability.
3. Strategies for young leaders to gain respect from senior team members by utilizing their expertise and focusing on owning your specific role rather than trying to do everything yourself.
4. Why a leader must "flip a switch" from disappointment back to work to best prepare their team for the next challenge.
5. Why the number one job of a coach or leader is to build a team member's confidence until they are ready to believe in their own "invincibility".

Timestamps

• 0:00 - Introduction
• 1:17 - The dream Kieran Read never thought was realistic
• 2:52 - When a coach sees the leader before you do
• 4:50 - The first thing new leaders should figure out
• 7:33 - How to lead people older and more experienced than you
• 9:11 - The leadership mistake TV teaches you to make
• 10:25 - The loss that taught Kieran he was trying too hard
• 11:47 - Why the best teams don’t depend on one leader
• 13:28 - The phone call every New Zealand kid dreams of
• 15:04 - Walking into a locker room full of legends
• 20:03 - What to do when your ego gets bruised
• 21:39 - What Richie McCaw quietly taught about leadership
• 25:13 - Taking over after a legend without copying him
• 27:38 - Why leaders need to connect before they correct
• 30:26 - The hidden weight of leading under pressure
• 32:12 - How trust makes hard conversations easier
• 34:02 - The conversation leaders avoid until it costs them
• 38:38 - The price of being someone people look up to
• 40:50 - The seven-month reflection that changed his next chapter
• 44:38 - Why belief has to come before confidence
• 46:13 - The coach’s real job isn’t technical
• 47:12 - Inside Kieran’s Human Endeavour leadership program
• 49:59 - Why leadership is learned, not born
• 51:26 - The snowball effect of better leaders
• 52:07 - The legacy that matters more than winning

About Kieran Read

Kieran Read is a legendary figure in international sports, having captained the New Zealand All Blacks 52 times during a career that included two World Cup championships. Rising from a self-described "shy kid" to a global leader, Kieran transitioned into professional leadership coaching after a period of intense self-reflection and academic study of applied management. Today, he is a keynote speaker and the creator of The Human Endeavour, a program dedicated to distilling his years of high-performance experience into actionable leadership pillars for the corporate and sporting worlds.

Resources and Mentions

Kieran Read’s LinkedIn: https://www.linkedin.com/in/kieran-read-00821384/

Kieran Read’s Instagram: https://www.instagram.com/kieranread08/

The Human Endeavour Program: https://www.redseed.com/kieranread-leadership

Kieran Read’s website: https://www.kieranread.co.nz/

Podcast Contact Information:

Website: www.learnit.com

Email: [email protected]

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Are you settling for stagnant performance because you're wrestling with a deep-seated lack of confidence or the "imposter syndrome" mask?

In this episode of The Learn-It-All™ Podcast, Damon sits down with executive coach and author Quinn Harwood to dismantle the barriers that keep high-performing emerging leaders from reaching their next level. Quinn shares his journey from professional basketball with the Los Angeles Lakers and Los Angeles Clippers, where a teenage Kobe Bryant showed him the true meaning of "next level" confidence, to coaching thousands on how to bridge the gap between performance and results. They dive into the psychology of the "hypocrite monster," the critical pivot from a victim mentality to radical ownership, and why a "gateway habit" at the end of your day is more impactful than your morning routine.

If you are a millennial or Gen Z leader feeling stuck in your career growth, this conversation provides a clear roadmap to align your mission with your money and build unshakeable resilience.

📘 Get a FREE copy of The Learn-It-All Leader Book: https://dl.bookfunnel.com/3ingcx2pp5

In this episode, you’ll learn...

1. How to defeat the "hypocrite monster"
2. Why moving from "the blame game" to a solutions-based mindset is the ultimate game-changer for reducing stress and achieving consistent results.
3. The "Kobe Level" of confidence: How to move past an intrinsic lack of confidence by attacking your growth gaps with a "Mamba Mentality."
4. Why developing social skills and the ability to influence emotions is the only way to bridge the connection void created by remote work and technology.
5. Why closing out your day with a "midnight mirror" reflection is more critical for your vitality than focusing solely on morning habits.

Timestamps

• [00:00] Introduction
• [01:01] The hidden reason high performers stay stuck
• [01:51] What Kobe Bryant revealed before the NBA
• [03:35] Where real confidence actually comes from
• [08:26] How leaders build belief without lowering standards
• [10:31] The three zones of becoming strong in life
• [12:11] What three injuries taught him about belief
• [14:13] The hypocrite monster every leader has to face
• [15:29] Why GrowthTime! had to become a fable
• [18:33] The ownership lesson most young leaders miss
• [21:37] When ownership gets replaced by victimhood
• [24:21] The coaching question that exposed the real problem
• [26:44] The village called Youville
• [29:19] Why ego quietly keeps leaders stuck
• [31:46] How to find purpose when everything feels fuzzy
• [33:35] Why AI cannot replace emotional intelligence
• [36:15] The remote work trap future leaders need to understand
• [39:41] Why learning without action changes nothing
• [42:26] What empowered confidence really feels like
• [43:51] The adulting gift every graduate needs
• [45:03] Why people hire Coach Q when they feel stuck
• [48:24] The gateway habit that changes everything
• [51:06] Where to connect with Coach Q
• [51:53] Damon’s challenge: ownership, growth, and getting unstuck
• [52:39] Damon and Madison unpack the Coach Q conversation
• [53:28] Is Learnit really a confidence intervention?
• [55:44] How to act before anxiety takes over
• [59:25] The uncomfortable truth about psychological safety
• [01:00:16] Why leaders should celebrate failure first
• [01:03:00] The lesson Damon learned from his daughter’s bike race

About Quinn Harwood

Quinn Harwood is an executive coach, author, and former professional basketball player. After a career that included stints with the Los Angeles Lakers' summer league and the Los Angeles Clippers, Quinn transitioned into leadership, serving as a general manager for high-performance organizations before moving into full-time coaching. He is the author of GrowthTime!: The Clear Path to Unlock Your Best Life and Leadership, a coaching fable designed to help emerging leaders navigate their personal and professional growth journeys. Quinn is dedicated to helping "mission movers" align their values with their careers through his coaching and his "Monday Movers Mindset" newsletter.

Resources and Mentions

GrowthTime!: The Clear Path to Unlock Your Best Life and Leadership book: https://www.amazon.com/GrowthTime-Coaching-Fable-Unlock-Leadership/dp/B0F1G847H4

Quinn Harwood’s LinkedIn: https://www.linkedin.com/in/quinn-harwood-455517108/

Quinn Harwood’s website: https://coachqharwood.com/

Podcast Contact Information:

Website: www.learnit.com

Email: [email protected]

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Follow Damon Lembi: Linkedin I Instagram I Facebook I X