the Learn-It-All™ podcast

You can’t solve 21st-century problems with 20th-century mindsets—and today’s guest is on a mission to change that. 

In this episode, Damon sits down with Erin Lewellen, CEO of Tilting Futures, to unpack how immersive, global learning experiences are transforming the next generation of leaders. From building self-awareness to teaching systems thinking and reducing bias, Erin shares how her team is reshaping leadership education—and what every company can learn from their model. 

Whether you lead a team, a classroom, or a company, this conversation will challenge how you think about growth, feedback, and the power of perspective. 

In this episode, you’ll learn: 

• Why self-awareness isn’t innate—it’s a muscle 
• The “look in the mirror” rule every leader should follow 
• How Tilting Futures develops young leaders from 100+ countries 
• Why discomfort and difference drive transformational growth 
• The #1 interview strategy to find self-reflective employees 
• How to build a feedback culture rooted in trust, not fear 
• The hidden cost of “meetings after the meeting” 
• What most orgs get wrong about defining values 
• How leaders can model curiosity and restraint in meetings 
• Why you need to stop saying “they” and start saying “we” 

Timestamps: 

• 00:00 – Can you teach self-awareness—or is it innate?  
• 01:45 – “Look in the mirror”: Erin’s foundational leadership habit  
• 03:30 – What Tilting Futures is and how it works  
• 05:35 – Why ages 17–22 are the sweet spot for impact  
• 07:10 – Teaching empathy through global immersion and collaboration  
• 08:50 – Travel as a tool for leadership and adaptability  
• 11:30 – Erin’s Cape Town story: Context, humility, and lifelong change  
• 14:45 – Leading meetings with curiosity and silence  
• 15:55 – What changes in student mindset after 4 months  
• 18:00 – The research: Reduced bias, more agency, stronger leadership  
• 20:40 – How global cohorts shift perspective and prejudice  
• 22:45 – Systems thinking and asset-based problem solving  
• 25:30 – Behind the scenes: Building Tilting Futures’ internal culture  
• 28:00 – “There is no ‘they’, only ‘we’”: One of their core principles  
• 30:30 – How Erin interviews for curiosity and growth mindset  
• 34:15 – Why soft skills are the hardest—and most critical—to teach  
• 35:45 – Encouraging disagreement to find the best idea  
• 38:00 – Practicing emotional honesty in meetings  
• 40:30 – Ditching “the meeting after the meeting”  
• 42:00 – Aligning staff and student values: One unified culture  
• 44:25 – Keeping values alive in every meeting  
• 46:45 – How this generation of students is different  
• 49:30 – The Zimbabwean biomedical engineer who redefined her mission  
• 52:00 – Erin’s why: Helping young leaders unlock their impact  
• 54:00 – Scholarships, access, and how to get involved 

About Erin Lewellen: 

Erin Lewellen is the CEO of Tilting Futures, a nonprofit redefining global education through immersive leadership experiences. With operations in Cape Town and Malaysia, Tilting Futures equips young adults from over 100 countries with the skills, networks, and self-awareness needed to solve complex global challenges. A former high school basketball coach and champion of inclusive leadership, Erin brings a systems-level perspective to everything from education reform to organizational culture. She’s also a Forbes contributor and advocate for integrating “soft” (human) skills into every stage of leadership. 

 Resources & Mentions: 

• Tilting Futures website 
• Erin Lewellen on LinkedIn 
• Forbes article: The Soft Skills That Can’t Be Replaced By AI 
• Apply to Take Action Lab 

Connect With Us: 

• Uplevel yourself and your team at Learnit.com 
• Email us: [email protected] 
• Follow Damon on LinkedIn 
• Follow Damon on Instagram 

Why does stress feel so normal in the workplace? Why does our mind default to the worst case scenario? And what’s the cost of this being our normal day to day life? 

In this episode, Damon sits down with Derek Sloan, who’s a licensed therapist, executive coach, and founder of Abridge Leadership to explore why so many professionals silently battle negativity and self-doubt, and what leaders can do to break the cycle. 

Whether you're navigating organizational change, dealing with anxious thoughts, or trying to model vulnerability in a remote workplace, this episode offers practical tools backed by psychology and made for the real world. 

In this episode you’ll learn: 

• What The 80% Rule is—and how it can transform how you lead 
• The hidden cost of “normalized” workplace stress 
• Why vulnerability is a leadership superpower (when done right) 
• The difference between confidence and self-efficacy 
• How to spot fear-based thinking on your team 
• Practical ways leaders can create clarity, safety, and connection 
• And so much more! 

Timestamps: 

00:21 – Why our brains default to negativity (60,000 thoughts, 80% negative) 

01:53 – The thought-emotion-behavior chain: how negativity spreads 

03:42 – What happens when dysfunction is normalized at work 

05:45 – Breaking down The 80% Rule (3 surprising stats) 

09:00 – Addressing real pain vs. future-focused fear 

10:25 – The traps leaders fall into under stress 

12:23 – A case study: when a promotion becomes a source of burnout 

16:05 – What leaders can do during times of uncertainty 

18:45 – The power of focusing on controllables 

19:24 – 3 controllables: showing up as your best, staying hopeful, being transparent 

22:30 – Why vulnerability matters more than ever 

25:15 – Healthy vs. unhealthy vulnerability: where leaders get it wrong 

29:09 – Understanding fear: how our brains exaggerate the future 

33:27 – Self-efficacy vs. confidence—and why both matter 

36:05 – How to give better feedback (that actually develops talent) 

39:14 – Recognizing negativity loops in your team 

41:39 – Why listening—not fixing—is your leadership edge 

44:00 – The post-COVID shift: employees expect to be cared for 

45:32 – Can remote work ever match in-person connection? 

48:21 – Why loneliness is a hidden workplace epidemic 

50:15 – Final takeaway: Take inventory. Where are you now—and how long have you been there? 

About the Guest: 

Derek Sloan is a Licensed Professional Clinical Counselor (LPCC), Certified Clinical Trauma Professional (CCTP), and National Certified Counselor (NCC), He has experience in providing mental health and behavioral health services to individuals, couples, and groups. He founded and continues to operate a private practice in Kentucky. 

Derek is also a Certified Executive Coach and has a passion for leadership development. This has been a lifelong pursuit through his graduate degree in organizational leadership, building businesses, and leadership coaching/consulting. He works with executive leaders in top-level and industry-leading organizations, helping them enhance their emotional intelligence, communication skills, and decision-making abilities. His mission is to help organizations achieve their goals by prioritizing both leadership and mental health. 

Resources & Mentions: 

• Follow Derek on LinkedIn 
• Visit Derek's Leadership company Abridge Leadership 
• Man’s Search for Meaning by Viktor Frankl 
• Derek’s Podcast: Mental Stillness 
• Damon's appearance on Mental Stillness: https://podcasts.apple.com/us/podcast/38-special-guest-damon-lembi/id1717076433?i=1000703632140

Connect with Us: 

• Uplevel yourself and your team with our trainings: www.learnit.com 
• Email us: [email protected] 
• Follow Damon on LinkedIn and Instagram 

The 5 Truths Every New Leader Needs to Hear

Becoming a leader isn’t just a promotion—it’s a complete identity shift. You’re no longer just executing the work. You’re coaching others to do it well. And that requires a new mindset, a new skillset, and a new set of daily habits.

In this solo episode, Learnit CEO Damon Lembi breaks down the 5 truths he wishes every first-time leader knew. Whether you’re fresh in the role or mentoring someone who is, this episode is your tactical, no-fluff guide to making the leap from top performer to people-first leader.

In this episode, you’ll learn:

- Why leadership is about coaching, not doing

- The #1 mindset shift you must make in week one

- How to build trust by giving others autonomy (and space to fail)

- Why the best leaders are great listeners—first

- How to model the habits you want your team to follow

- The key conversation to have with your boss (today)

- What to do when your company won’t invest in your development

- Why mistakes are inevitable—and what to do when you make one

- How to lead without pretending to have it all figured out

Timestamps:

00:00 – The biggest professional shift: from player to coach

01:00 – Truth #1: You win through your people, not by doing it all

01:45 – Why delegation is really about building trust

02:00 – The mindset shift: you're building a team of heroes, not being the hero

02:30 – Truth #2: Don’t rush in—start by listening and learning

03:20 – Why curiosity builds credibility and connection

03:50 – Truth #3: Model the behavior you want from your team

04:30 – Leadership is a constant stage—how are you showing up?

04:45 – Truth #4: Own your success—don’t wait for others to invest in you

05:15 – How Damon recommends new leaders start growing (even on their own)

06:00 – The $14 tool that every new leader should use

06:30 – Truth #5: You will make mistakes—so learn fast and lead through it

07:10 – The hard lesson Damon learned about avoiding tough conversations

08:00 – The recap: 5 truths every new leader needs to thrive

08:30 – Final thought: Great leaders aren’t born or made—they’re always in the making

Resources & Mentions:

Damon’s book: https://www.learnit.com/learn-it-all-leader-book-by-damon-lembi

Learnit’s Delegation Greenlights E-Book: https://www.learnit.com/resources/delegation-greenlights-guide

Learnit’s Delegate to Scale Your Impact Course: https://www.learnit.com/courses/delegate-to-scale-your-impact

Learnit Article on New Manager Training Skills: https://www.learnit.com/blog/new-manager-training-skills

The Learn-It-All Podcast with Chris Dyer: https://www.youtube.com/watch?v=hBUHOPtR6Yk

Learnit Live Event:

https://www.youtube.com/watch?v=vjLFoCepWOw

Connect With Us:

Uplevel yourself and your team at Learnit.com

Email us: [email protected]

Follow Damon on LinkedIn

Follow Damon on Instagram

The modern workplace runs on meetings. But too often, those meetings become time sinks instead of value drivers. 

People scramble to take notes, miss critical insights, and leave unclear on what to do next. Meanwhile, leaders drown in back-to-back calls with no bandwidth to spot patterns or coach teams effectively. And yet... what if meetings weren’t the problem, but the raw material for your company’s next big leap? 

In today’s episode, Damon is joined by Richard White, CEO and founder of Fathom breaks down his best lessons as a 3x founder and how he’s building the future of work. 

In this episode, you’ll learn: 

• Why retention—not revenue—should be your first startup focus 
• How Richard built a viral product without a sales team for 12+ months 
• The underestimated power of onboarding and customer support 
• How to create a freemium product that actually drives word of mouth 
• Why AI will soon give every employee a “highlight reel” of what matters most 
• The truth about building in the AI era: it’s not about features—it’s about output quality 

Timestamps: 

00:00 – Richard’s early builder mindset and why he couldn’t be an employee 

01:22 – Why articulating the “why” is a founder’s core job 

02:07 – Finding his tribe in the first batch of Y Combinator 

04:25 – How confidence and founder networks shaped his journey 

05:44 – The trap of over-relying on advice vs. trusting your instincts 

07:51 – Why Richard calls UserVoice his “founder finishing school” 

08:38 – Lessons in cross-functional leadership and scrappy execution 

11:05 – Advice for technical founders who undervalue sales 

12:33 – The insight that sparked Fathom: meetings are broken 

14:44 – How he hired a “sales team” with nothing to sell 

15:05 – Why he delayed monetization and focused on retention first 

17:57 – Building customer feedback loops into the product 

19:32 – From 1,000 users to viral growth via the Zoom Marketplace 

21:50 – The psychology behind freemium and referability 

24:42 – Why onboarding was a 9-month engineering priority 

26:47 – Balancing new features with polishing the UX 

28:58 – The contrarian view: meetings aren’t bad—meeting waste is 

29:22 – How Fathom reduces meeting bloat and improves async sharing 

31:36 – Using Fathom to streamline the hiring process 

33:39 – What’s next: AI that watches every meeting and summarizes insights 

36:05 – Generating case studies and internal docs from conversation data 

36:52 – Cross-org AI search and the power of complete data sets 

37:59 – What separates great AI products: obsessive quality control 

39:51 – The future belongs to teams that can turn conversations into knowledge 

Resources Mentioned: 

• Fathom 
• Connect with Richard White on LinkedIn 
• UserVoice 

About the Guest: 

Richard White is the founder and CEO of Fathom, a free AI-powered meeting assistant that helps teams skip note-taking and unlock insights from every call. He’s a three-time founder, early YC alum, and product-obsessed builder who believes meetings are the new knowledge base—if we capture them right. 

Connect With Us: 

• Level up your sales team at Learnit.com 
• Email us: [email protected] 
• Follow Damon on LinkedIn 

Leadership isn’t just about vision. Instead it’s about showing up in the everyday moments if you want to shape great teams, cultures, and results. 

There’s myth that some people are “born leaders” but in today’s episode, leadership expert Dr. Scott Allen shares why leadership is learned, practiced, and most importantly, deeply personal. 

In this episode you will learn: 

• Why the idea of “natural-born leaders” is outdated 
• The science behind charisma (and how to develop it) 
• What leadership styles have in common with golf clubs 
• The difference between authority and influence—and why influence wins 
• Why “thinking partners” are essential for every leader 
• How to combine knowledge, skill, mentorship, and experience for true growth 

Timestamps: 

00:14 – Are leaders born or made? 

01:49 – What science says about charisma and learnable leadership 

03:48 – How problem-solving, negotiation, and communication can be developed 

06:00 – Leadership styles and the “golf club” metaphor 

08:42 – Making leadership training stick: from hacks to habits 

09:43 – Why self-awareness is foundational to great leadership 

12:08 – Character, curiosity, and the power of learning 

13:02 – Can self-awareness be taught? 

15:36 – Curiosity as a leadership superpower 

17:02 – Coaches who deflect blame vs. leaders who take ownership 

18:12 – Empathy, ego, and the limits of expertise in leadership 

20:26 – Why catchers make great managers 

21:43 – Influence: the real heart of leadership 

24:07 – Trust as the currency of leadership 

25:48 – Influence tactics: from logic to coalitions 

28:18 – Timing and persuasion in leadership conversations 

30:01 – Why knowledge alone isn’t enough—real-world learning is essential 

33:22 – The five domains of leadership learning 

35:27 – Creating learning organizations with psychological safety 

37:54 – The role of thinking partners in leadership development 

41:04 – How to find (and build) your bench of thinking partners 

46:57 – Why one partner won’t solve everything—and that’s the point 

49:01 – “Who you are is how you lead” – Scott’s favorite leadership quote 

50:39 – Final thoughts on responsibility, reflection, and showing up for others 

About the Guest: 

Dr. Scott J. Allen is an award-winning educator, keynote speaker, and leadership expert. 

With over 17 years as a professor and more than 60 peer-reviewed publications, Scott brings academic rigor, humor, and real-world insight to every engagement. 

He's co-authored several books on leadership and hosts Practical Wisdom for Leaders—a podcast ranked in the top 2.5% globally. He also publishes a weekly newsletter for busy practitioners, highlighting four leadership articles. 

Scott energizes audiences at marquee organizations such as Toyota Motor North America, Cleveland Clinic, NASA-Glenn, Nestlé, Progressive, Whiting Turner, Sam's Club, the Federal Reserve Bank of Cleveland, and Progressive through his dynamic keynotes, workshops, and retreats. 

Whether on stage or in the boardroom, Scott’s expertise in leader development, the future of work, and executive communication empowers leaders to drive meaningful, lasting change. 

Resources & Mentions: 

• Connect with Scott on LinkedIn: https://www.linkedin.com/in/scott-j-allen/  
• Visit Scott's Website: www.scottjallen.net 
• Listen to his Podcast: https://www.scottjallen.net/podcast  
• HBR Article: Leadership That Gets Results by Daniel Goleman: https://hbr.org/2000/03/leadership-that-gets-results  
• Influence by Robert Cialdini: https://a.co/d/hl0KHmq  
• Pre-Suasion by Robert Cialdini: https://a.co/d/hl0KHmq  
• Gallup’s workplace engagement stats: https://www.gallup.com/workplace/654911/employee-engagement-sinks-year-low.aspx#:~:text=In%20the%20latest%20reading%2C%20from,than%202020's%20high%20of%2036%25 
• Tiny Habits by BJ Fogg: https://a.co/d/81197UZ  
• Atomic Habits by James Clear: https://a.co/d/81197UZ  

Connect With Us: 

• Learn more about our leadership and team development trainings: www.learnit.com 
• Email us: [email protected] 
• Follow Damon on LinkedIn and Instagram 

Damon Lembi never set out to become a podcaster. But 2 years, 160+ episodes, and thousands of conversations later, he can say this with confidence: podcasting has been the single most transformative tool in his professional growth.

In this solo episode, Damon breaks down the 8 ways podcasting has made him a better leader, communicator, and human being and why every professional should seriously consider stepping behind the mic.

In this episode, you’ll learn:

- Why podcasting is the ultimate communication gym

- How storytelling on-air can make you more persuasive off-air

- What podcasting does for your confidence and clarity

- The hidden networking power that comes with each episode

- Why podcasting forces you to become a better listener and improviser

- How hosting a show accelerates your learning and thought leadership

- The simple way to turn one podcast guest spot into 10 pieces of content

- Why your personal brand matters (even if you don’t think it does)

Timestamps:

00:00 – Damon’s confession: The one unexpected thing that changed his career

00:35 – #1: How podcasting sharpened his communication

01:10 – #2: Why repetition made him a better storyteller

01:50 – #3: Overcoming fear and building confidence through reps

02:30 – #4: 10x network growth—and the power of asking

03:00 – #5: How the mic made him a better listener at work and at home

03:45 – #6: Learning to improvise and build trust fast

04:20 – #7: The accelerated learning effect (and why it feels like free coaching)

05:15 – #8: How podcasting helped him build a real, visible personal brand

06:10 – Guesting vs. hosting: Where to start and what tools to use

06:50 – Why you don’t need followers—just courage

07:10 – A final reflection: Podcasting made me better. It can do the same for you.

Resources & Mentions:

Episode with Marques Ogden: https://youtu.be/dqsRJhGIeFI?si=98MKdtArx30guTBE

Episode with Stephen M.R. Covey: https://youtu.be/iP6cnAqNwIc?si=pl6lCTHKgM9v-sn5

Episode with Doug Conant: https://youtu.be/418p49ClihY?si=YuLozGLm4VsFXM1B

Episode with Dr. Jessica Kriegel: https://youtu.be/TUJ-8zUolI4?si=UNYpf_LwQ5pzi2Ni

Episode with Matt Dixon: https://youtu.be/0LpEfvxsOYs?si=mAEJwxIREFnmeg3g

PodMatch: Tool to book guest spots: https://www.podmatch.com/

Opus Clip to make podcast clips: https://www.opus.pro/

Pat Flynn’s Guide: How to Start a Podcast in 2025: https://www.smartpassiveincome.com/

Connect With Us:

Level up your sales team at Learnit.com

Email us: [email protected]

Follow Damon on LinkedIn

Follow Damon on Instagram

The traditional way of selling in B2B businesses no longer works. Win rates are at an all-time low. Sales reps are burning out faster than ever. Quotas are missed quarter after quarter. And so what are teams trying? To just do more. More calls. More demos.  

But the solution isn’t more. First, you have to break the cycle you are stuck in. 

In today’s episode, Damon is joined by Dave Brock. He’s a legendary sales advisor, executive coach, and author of The Sales Manager Survival Guide. He's here to break down what’s wrong with the way we train sales teams today, and how modern leaders can build cultures that actually drive performance. 

In this episode, you’ll learn: 

• Why most sales teams are stuck and what it really takes to break the cycle 
• How business acumen and curiosity outperform slide decks and sales pitches 
• The real reason tenure is shrinking in sales and what to do about it 
• How to coach your team effectively  
• What Dave is building with AI and why it might be the future of learning 

Timestamps: 

00:00 – What’s going wrong in sales today? 

02:10 – Why win rates are declining and panic is missing 

05:27 – Are people losing their drive to achieve? 

07:34 – COVID’s effect on employee disconnection 

08:49 – Culture, belonging, and why people leave 

10:32 – What great leaders do differently 

12:22 – The math doesn’t work: ramp time vs. tenure 

15:56 – How short-term thinking hurts everyone 

16:36 – Why most sales cycles end in no decision 

18:59 – The key to building trust: problem-first conversations 

21:23 – The pitch is dead—long live collaboration 

23:39 – Why salespeople lack business acumen 

24:42 – The real role of subject matter experts 

26:20 – The $500k SDR: a credibility case study 

29:23 – Where to find your next great SDR 

31:15 – Brand damage from bad conversations 

33:56 – One-size-fits-all coaching doesn't work 

34:55 – What frontline managers get wrong 

36:58 – Directive vs. non-directive coaching 

38:56 – Coaching inside every conversation 

42:32 – Using improv to teach collaborative coaching 

44:59 – Coaching in “cracks of time” 

45:54 – What’s changed since The Sales Manager Survival Guide 

47:52 – Preview of Dave’s next book: Sales Executive Survival Guide 

49:05 – Using AI as a debate partner, not a crutch 

51:25 – Learning faster through collaborative AI tools 

53:59 – Dave’s master prompt strategy for ChatGPT and Claude 

54:18 – What keeps Dave curious after decades of success 

56:35 – What extreme sports and Wu-Tang taught him about innovation 

59:28 – Why mentoring high schoolers keeps him sharp 

Resources Mentioned: 

• Partners in EXCELLENCE Blog 
• Follow Dave Brock on LinkedIn 
• Sales Manager Survival Guide by Dave Brock 
• AI Driven Leader by Jeff Woods 

About the Guest: 

Dave Brock is the author of Sales Manager Survival Guide. He leads Partners in EXCELLENCE, which helps sales leaders rethink coaching, culture, and customer engagement. Dave’s recent work includes AI-powered sales learning tools based on curiosity, problem solving, and trust-building. 

Connect With Us: 

Level up your sales team at Learnit.com 

Email us: [email protected] 

Follow Damon on LinkedIn 

Follow Damon on Instagram 

If you want to be a successful leader in today’s fast paced world, stop focusing on just hitting your targets in business. Instead, you need to focus on understanding your team, so that they can help you achieve more than you could on your own. But how do you do that? 

In today’s episode, Damon is joined by Kerry Rockers, an executive coach, HR veteran, and passionate advocate for helping leaders build more human-centered workplaces. 

In this episode, you’ll learn: 

• Why great coaching isn’t about fixing people, but about helping them hear their inner voice again 
• How to navigate career pivots with clarity and confidence 
• The difference between leading and managing—and why it matters now more than ever 
• Why HR is more strategic than it’s ever been 
• Simple shifts to help your team find meaning in their work 

Timestamps: 

00:20 – The true goal of coaching: helping people remember what they already know 

02:14 – Coaching the ambitious vs. the stuck: what’s different? 

03:34 – What makes someone “coachable”? 

04:26 – Kerry’s journey from HR executive to full-time coach 

06:47 – How HR has evolved in the past 20 years 

07:50 – Making the leap to entrepreneurship (even if it’s unexpected) 

09:26 – How to approach a career pivot with intention 

12:19 – Why experimenting and networking is key to a successful transition 

13:58 – Tools for gaining clarity on what you want next 

15:44 – How to learn in a way that works for you 

16:40 – Why more people are searching for meaning in work 

18:07 – How Kerry helps clients discover their values 

19:52 – The calendar and checkbook audit: aligning time and values 

20:20 – How managers can help their team feel more connected to their work 

22:21 – Listening for values in everyday conversations 

23:52 – One simple way to become a better listener 

24:52 – A powerful 1:1 question Kerry uses to surface meaning 

26:36 – What to do if you’re not good at receiving feedback 

28:03 – The trust cost of canceling 1:1s 

30:02 – What a “stay interview” is and why every manager should use it 

33:12 – How to keep top talent even when change isn’t possible 

33:44 – One mindset shift middle managers need to build trust 

35:50 – The story of the leader who helped Kerry make a pivotal leap 

39:23 – Tools for increasing self-awareness (and why it matters) 

42:08 – Can self-awareness be taught? 

43:18 – How StrengthsFinder helped one client reframe chaos into purpose 

45:46 – How to work better with different strengths on your team 

47:07 – Final thoughts on intentionality, curiosity, and leadership 

About the Guest: 

Kerry Rockers is a certified executive coach and former global HR executive with over two decades of experience. Kerry has consulted and coached leaders across multiple business lines and functions (Technology, Digital Channels, Wholesale Banking, Corporate Support teams etc.) with significant experience working internationally.  Her business acumen and broad experience working with teams and leaders during times of change help her quickly understand her coaching client's challenges.   

Resources Mentioned: 

• Kerry Rockers' Website 
• Connect with Kerry on LinkedIn 
• CliftonStrengths Assessment 

Connect With Us: 

Uplevel yourself and your team with our trainings: www.learnit.com 

Email us: [email protected] 

Follow Damon on LinkedIn: https://www.linkedin.com/in/damonlembi/ 

Follow Damon on Instagram: https://www.instagram.com/damonlembi/ 

In this solo episode, Learnit CEO and bestselling author Damon Lembi shares 12 powerful truths he’s learned over the years that he wishes someone had told him in his 20s.

From managing money and making bold career moves, to saying no, navigating failure, and redefining your identity, Damon gets real about the missteps and wake-up calls that shaped who he is today.

In this episode, you’ll learn:

- Why time—not money—is your most valuable asset

- How to stop making decisions you’ll regret

- A 5-part plan to take control of your finances (without needing to be a CPA)

- What most people get wrong about failure

- How to know when it’s time to quit the job, relationship, or habit

- Why your job title isn’t your identity—and what matters more

- A mindset shift that makes confidence inevitable

- The secret to avoiding burnout (especially if you're a top performer)

- How living abroad can completely change the way you lead

Timestamps:

00:35 – #1: Time is the only asset you can’t get back

02:00 – Why you need to be intentional about your relationships

03:00 – Are you overworking or failing to delegate?

04:00 – #2: Money management tips Damon wishes he learned earlier

06:00 – #3: Stop making emotional decisions—use “purposeful awfulizing”

07:30 – #4: Get comfortable with failure (and why not trying is the real risk)

08:10 – #5: Don’t stay stuck—recognize the sunk cost fallacy

09:00 – #6: Life isn’t linear—adaptability is the superpower

10:30 – #7: Take action—confidence comes from reps, not perfection

11:45 – #8: Learn to say no—and avoid the “VIP curse”

13:00 – #9: Don’t avoid tough conversations (especially as a leader)

14:30 – #10: Your identity isn’t what you do—it’s who you are

15:40 – #11: You’ll regret the chances you didn’t take

16:50 – #12: Travel, live abroad, and widen your worldview

17:55 – Damon’s challenge to listeners: Pick one, apply it this week

About Damon Lembi:   

Damon Lembi is a 2x 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 & Mentions:

Damon’s book: The Learn-It-All Leader: https://www.amazon.com/dp/B0BZXKR784?ref_=cm_sw_r_ffobk_cp_ud_dp_4NRSE6WY9TWPASVJZ2H2

Gary Ridge’s book: Any Dumb Ass Can Do It: https://a.co/d/hTV9gD0

Erin Lewellen and Tilting Futures: https://www.tiltingfutures.org: https://tiltingfutures.org

Connect With Us:

Uplevel yourself and your team with our trainings: www.learnit.com

Email us: [email protected]

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Have you ever wondered what it takes to succeed in a high-stakes business? 

It’s not a simple life. There’s things to gain, but also things to lose. Today’s episode is an incredible cautionary tale for those of you who are building your way to success. 

In today’s episode, Damon is joined by Butch Meily, former PR strategist to Reginald Lewis, a leveraged buyout dealmaker, and now humanitarian—to discuss his powerful memoir From Manila to Wall Street. 

In this episode you’ll learn 

• Why proximity to power can be both a blessing and a burden 
• The personal cost of chasing high-level success 
• What business titan Reginald Lewis taught Butch about leadership, identity, and pressure 
• How Butch transitioned from PR executive to global humanitarian 
• Why “ordinary lives” often lead to the deepest happiness 
• And so much more. 

Timestamps: 

00:00 – Intro to Butch Meily 

00:29 – The cost of attaching yourself to powerful people 

01:30 – Why Butch finally wrote his memoir 

02:36 – Who the book is for and how it's structured 

03:50 – Butch’s first meeting with Reginald Lewis 

05:17 – Reg’s early PR battle and the New York Times story 

07:10 – Getting screamed at in a Bentley: Butch’s first ride with Reg 

08:49 – The emotional toll of working under constant pressure 

10:35 – Life regrets and the wisdom of Barbara Bush 

12:10 – Can you have both success and happiness? 

14:02 – Leveraged Buyouts 101 + the Beatrice takeover story 

18:55 – Where Reg’s courage really came from 

20:10 – Reg’s mantra: Keep going no matter what 

22:18 – The role of luck and hard work 

23:27 – Why America is still the land of opportunity 

25:03 – Butch’s “candy cane” vision of America vs. Reg’s experience as a Black man 

27:14 – The pressure of being “not a Black success—but an American success” 

29:21 – The Hamptons mansion fire: real-life suspense 

34:12 – Reg passes away, then Butch’s father dies days later 

37:39 – Butch is fired—then brought back by an unexpected new CEO 

40:12 – How Loyda Lewis led with grace, faith, and fierce business savvy 

42:34 – Would Reg like the book? And why Butch wrote it now 

44:36 – Butch’s new life: humanitarian work and startup mentorship 

46:01 – Final lesson: why “ordinary” is extraordinary 

Resources Mentioned: 

• From Manila to Wall Street by Butch Meily 
• Butch Meily LinkedIn
• Butch Meily’s Website 
• Reginald F. Lewis Museum 

 About the Guest: 

Butch is the author of the memoir, From Manila to Wall Street – An Immigrant’s Journey With America’s First Black Tycoon. 

Butch’s current job is President of the Philippine Disaster Resilience Foundation (PDRF), a private sector disaster management organization that includes the major business groups in the country.  He helped found PDRF, turning it into a global role model for private sector involvement in calamities. The organization operates the world’s first national private sector Emergency Operations Center. Philippine Long Distance Telephone (PLDT), his parent company, received the 2016 Prince of Wales Business in Community UPS International Disaster Relief Prize for its work in organizing PDRF after Typhoon Ketsana in 2009 and mobilizing it during Super Typhoon Haiyan in 2013. 

Butch has worked in conflict situations in the southern Philippines including a terrorist siege in 2013 and an ISIS-inspired rebellion in 2017. 

Butch wears several hats. He heads IdeaSpace Foundation, a technology accelerator for early-stage startups, and QBO Innovation Hub, a public private partnership launched to mentor startups. Until December 2020, he served as president of Pacific Global One, an aviation firm affiliated with PLDT. 

Previously, Butch was First Vice President and Special Assistant to the chairman of PLDT and president of PLDT Smart Foundation.  Prior to joining PLDT, he served as Vice President, Communications for TLC Beatrice International, a food company in New York and Paris and the main subject of his book.  He has worked with several New York public relations firms and a financial startup there. 

Butch graduated from the Ateneo de Manila University and earned an MA in Journalism and Communications from the University of Florida (UF), becoming the first honors graduate of the program. He returned to UF as a Freedom Forum Distinguished Professor and received a Distinguished Alumnus award and was named to the school’s Hall of Fame. He started but did not finish his MBA at Northwestern University. He has taken writing classes at Grub Street and at New York University’s Continuing Education Program, a long time ago. 

In 1997, he established a permanent scholarship in his father Joe Meily’s name, at the Ateneo. That same year, he made a small donation to the College of Journalism and Communications at the University of Florida. 

Connect With Us: 

Uplevel yourself and your team with our trainings: www.learnit.com 

Email us: [email protected] 

Follow Damon on LinkedIn: https://www.linkedin.com/in/damonlembi/ 

Follow Damon on Instagram: https://www.instagram.com/damonlembi/