the Learn-It-All™ podcast

In this episode of The Learn-It-All Podcast, host Damon Lembi sits down with Nick Damoulakis, founder and CEO of Orases, recently ranked as the #1 AI and custom software company in the US. Nick’s journey from a college dorm room to leading a nationally recognized tech firm is packed with hard-won lessons on leadership, resilience, and the future of work. The conversation covers everything from Nick’s notorious brush with a Beatles copyright lawsuit to his foundational beliefs on transparency, failing fast, and building teams that weather any storm. Nick also takes us inside the practical steps organizations must take to become truly AI Ready—including why it has to start at the top, and the frameworks he uses to enable company-wide transformation. If you’re passionate about leadership, culture, or the coming wave of AI, you’ll find idea after actionable idea in this episode. 

In this episode, you’ll learn: 

• How Nick turned a college copyright crisis into a launchpad for a thriving tech company. 
• Why vulnerability and transparent failure-sharing are core to building a psychologically safe team. 
• The “bison story” and Nick’s playbook for leading through adversity and economic downturns. 
• Nick’s step-by-step, psychology-driven method for creating real buy-in during major organizational change. 
• What “AI readiness” really means, the three kinds of AI leaders every company needs, and why a Chief AI Officer isn’t a silver bullet. 
• How to spot and empower volunteer innovators, and why small wins are the key to sustainable transformation. 

Timestamps:

00:00 – Three types of AI leaders in organizations 

00:22 – Welcome & Nick’s intro: the path from guitar tabs to CEO 

01:36 – Nick’s first boardroom: sued by Sony & BMG in college 

03:36 – Turning crisis (and near-expulsion) into a full-time tech job 

05:14 – The “Lingo” story: courage, candor, and faking it ‘til you make it 

08:27 – Advice for leaders on stepping out of their comfort zones 

11:44 – Emotional intelligence and social sensitivity in leadership 

14:33 – Surviving downturns: dot-com bust, the Great Recession, COVID 

16:13 – Nick’s framework for helping CEOs correct toxic cultures 

17:15 – When Nick realized he was “the problem” and how he changed 

20:32 – The turning point: recovering from losing $450k in billing 

25:39 – How to prepare for and communicate through scary company meetings 

30:09 – Creating a culture where people never want to let you down 

32:09 – Psychological safety, “oopsies,” and sharing fast failures 

36:09 – How Nick helps teams disrupt themselves and embrace change 

38:59 – Change management, the 8-step model, and enlisting volunteers 

40:29 – AI readiness: why it must come from leadership, not consultants 

43:00 – What incentives, skills, and resources organizations need to make AI practical 

45:48 – Simple wins: Nick’s AI agent example and democratizing innovation 

50:20 – The “Three Buddha Questions” for overcoming any challenge 

About Nick Damoulakis 

Nick Damoulakis is the founder and CEO of Orases, named the #1 AI and custom software development company in the US by Clutch and recognized by Gartner as a top 25 emerging specialist consultancy. Nick’s career began in a college computer lab, launching one of the first online guitar tab archives—a venture that earned him fans, a lawsuit from major record labels, and eventually, his first big tech break. Over nearly 25 years, Nick has guided Orases through economic storms, industry disruption, and his own leadership evolution, developing repeatable frameworks for AI transformation and healthy company culture along the way. He’s a sought-after expert on AI readiness and organizational change, known for his candid stories and actionable strategies. 

Resources & Mentions: 

• Orases Website: https://orases.com/ 
• Nick Damoulakis LinkedIn: https://www.linkedin.com/in/nickdamoulakis/ 
• Vistage (CEO Peer Group) 
• Collective Edge by Colin Fisher 

Podcast Contact Information 

Website: www.learnit.com 

Email: [email protected] 

Follow us on LinkedIn and Instagram for more updates. 

In this empowering solo episode, Damon Lembi tackles imposter syndrome head-on, drawing inspiration from Oprah’s conversations with icons like Obama and Beyoncé, to moments of his own self-doubt on stage and in the boardroom. Damon unveils his proven four-step framework for overcoming the fear and uncertainty that plagues even the most accomplished professionals. Whether you’re a new manager, a seasoned leader, or someone ready to take your shot at something bigger, this episode delivers actionable advice, practical exercises, and a rallying call to step out of your comfort zone and into your next level. 

From labeling your fear to harnessing the power of deliberate practice, this is your roadmap to building confidence, beating self-doubt, and leading with courage. 

In this episode, you’ll learn: 

• Why even the most successful people struggle with imposter syndrome (and why that’s normal) 
• Damon's four-step framework to overcome self-doubt and step confidently into new opportunities 
• The power of “purposeful awfulizing” to reframe your biggest fears 
• Why action (not just planning) is the secret ingredient to building real confidence 
• The role of deliberate practice in mastering new leadership skills 
• How letting go and learning from every experience accelerates your growth 

Timestamps: 

00:00 – Imposter syndrome isn’t a weakness—it’s a human experience 

00:40 – Damon’s story: Coaching baseball in his 20s with no experience 

01:30 – Learning to lead when you feel unqualified 

02:00 – Why confidence often comes after the reps, not before 

02:40 – Brené Brown, Jamie Foxx, and others who’ve spoken up about this 

03:20 – Reframing imposter syndrome as a signal—not a flaw 

04:00 – Lesson #1: You don’t have to be the expert—just be in service 

04:30 – Lesson #2: Get radically honest about your fears (then move anyway) 

05:15 – Lesson #3: Curiosity beats confidence 

06:00 – Lesson #4: Preparation quiets the noise 

06:45 – Lesson #5: Talk to yourself the way you’d talk to a friend 

07:30 – Damon’s go-to journaling prompt when imposter syndrome hits 

08:15 – A challenge to leaders: Name where you're holding back 

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 & Mentions: 

• Damon Lembi LinkedIn 
• Learnit 
• Learn It All Leader (Book by Damon Lembi) 
• The Learn-It-All Leader for Kids (Kids Bood by Damon Lembi 
• Learnit 45-Day Free Trial for Teams: learnit.com/free 
• Learnit Give and Receie Feedback Class 
• Learnit Delegation class 
• Learnit Listening class 

Podcast Contact Information: 

Website: www.learnit.com 

Email: [email protected] 

Follow us on LinkedIn and Instagram for more updates. 

What if not every executive needs to be a “leader,” and the secret to scaling smart is building trust, not just in people, but in processes? In this thought-provoking episode of The Learn-It-All Podcast, Damon Lembi sits down with Curtis Hite, CEO of Improving, to explore the transformative power of conscious capitalism, purpose-driven business, and the nuanced difference between leaders, managers, and administrators. Curtis pulls back the curtain on the culture strategies that helped Improving grow to over 2,000 employees, $280M+ in revenue, and repeated “Best Place to Work” awards. Discover how trust is turned into action, and why “inspire, not require” is more than just a motto. Plus, Curtis shares the inside scoop on Improving’s internal engagement platform, AI’s real-world impact, and why celebrating (not bashing) capitalism is more urgent than ever. 

Packed with actionable advice for executives, culture builders, and anyone rethinking what it means to lead, this episode is a roadmap for scaling teams, winning hearts, and transforming companies from the inside out. 

In this episode, you’ll learn: 

• Why Curtis believes we need to “stop bashing capitalism and start elevating it,” and how conscious capitalism creates positive change 
• The foundational role trust plays in culture-building, and how Improving operationalizes it using Stephen M.R. Covey’s “Speed of Trust” framework 
• How to create a best-in-class culture at scale, without falling into the trap of “command and control” 
• Why not every executive should be a leader, and how to optimize for leaders, managers, and administrators 
• The power of visibility and engagement with Improving’s proprietary “Engage” platform (and how it can transform accountability) 
• How to embrace artificial intelligence as a superpower for executives, and the easiest first step to get started 

Timestamps: 

00:00 – Curtis on why not all executives are leaders, and why that’s okay 

01:43 – The case for celebrating (not bashing) capitalism 

03:34 – The big myths about capitalism, poverty, and progress 

05:43 – What is conscious capitalism, and how does it differ from stakeholder capitalism? 

07:27 – “Inspire, not require,” why framing matters in business initiatives 

10:56 – Curtis’s entrepreneurial journey: from defense tech to CEO 

13:55 – Turning shame and setbacks into entrepreneurial drive 

16:04 – The story behind the “Improving” brand and company 

17:13 – How to scale culture with 2,000+ employees and 17 offices 

19:24 – Real-world examples of values-driven local flexibility 

22:00 – Vetting for “we” vs. “me” cultures in acquisitions 

24:06 – How to shift a team from “me” to “we,” practical trust behaviors 

26:32 – Institutionalizing trust: trainings, trustpods, and everyday habits 

29:05 – All about Improving’s “Engage” platform: visibility, coins, and real impact 

32:20 – Handling pushback and building engagement for all personality types 

33:47 – Will “Engage” launch as a product? 

34:40 – Why not every executive is, or should be, a leader 

39:12 – The dangers of promoting only “leaders,” and how to build a balanced org 

44:19 – How Improving is leveraging AI now, and what every executive should do next 

47:37 – Staying agile with a 10-year vision in a fast-changing world 

50:49 – How Curtis continues to learn, grow, and seek feedback, even after winning major awards 

52:41 – Damon’s takeaways: why team, trust, and frontline ideas matter most 

About Curtis Hite 

Curtis Hite is the CEO and founder of Improving, a technology consulting and training company he launched in 2007. Under his leadership, Improving has grown to over 2,000 employees with 17 offices and revenues surpassing $280 million, winning more than 100 “Best Place to Work” awards along the way. Curtis is a leading advocate of conscious capitalism, trust-based leadership, and scalable, values-driven culture. His unique approach to executive roles, culture-building, and employee engagement has made Improving a standout in both growth and workplace excellence. 

Resources & Mentions: 

• Improving Website 
• Curtis Hite on LinkedIn 
• Conscious Capitalism Movement 
• “Conscious Capitalism” by John Mackey & Raj Sisodia 
• “The Speed of Trust” by Stephen M. R. Covey 
• YPO – Young Presidents’ Organization 
• Blue Ocean Strategy 
• Peter Bissonnette – Shaw Communications 

Podcast Contact Information: 

Website: www.learnit.com 

Email: [email protected] 

Follow us on LinkedIn and Instagram for more updates. 

In this actionable episode of The Learn-It-All Podcast, Damon Lembi sits down with Greg Satell, renowned transformation expert and bestselling author of Cascades: How to Create a Movement that Drives Transformational Change. Together, they unpack why organizational change efforts so often fail, the psychology of resistance, and how bold leaders can actually get people aligned without creating change fatigue or endless internal battles. Greg doesn’t just talk theory—he delivers proven frameworks for diagnosing resistance, earning “keystone wins,” and spreading transformation by movement, not mandate. Whether you're wrestling with skeptics or plotting your next big initiative, this episode is stacked with practical wisdom for anyone facing change at work or beyond. 

In this episode, you’ll learn: 

• The five types of resistance to change (and why only four are rational) 
• Why shared values, not just purpose, are the true foundation for successful transformation 
• How to spot “change fatigue” and set limits on how much change your organization can handle 
• The secret to keystone wins: start small, iterate with enthusiasts, and scale from early successes 
• How movements, not mandates, create truly lasting organizational change 
• Strategies for handling skeptics and building momentum through peer networks instead of persuasion 

Timestamps: 

00:00 – Change fatigue, why most transformations burn out, and the mandate vs. movement dilemma 

01:24 – The real reason change fails: resistance (what the data shows) 

02:59 – The five categories of resistance: trust, fatigue, switching costs, incentives, and identity 

09:33 – When (and when not) to engage with skeptics or “identity-based” resistors 

13:41 – The power of shared values (and how LGBTQ+ rights found common ground) 

15:45 – Discovering shared purpose and values—what leaders must do first 

18:25 – Why values come with real costs (IBM’s culture turnaround story) 

23:50 – The myth of “constant change”: why too many initiatives sink organizations 

25:17 – Tipping points: you only need 10–20% early adopters to drive major change 

28:30 – Why peer networks (not memos) spread new behaviors 

30:20 – Don’t try to “boil the ocean”: the keystone change playbook for rapid scaling 

35:37 – Why you always start with enthusiasts (and iterate in small groups) 

38:21 – What the Agile movement got wrong about signaling and shared values 

39:48 – Why learning from failure is the backbone of every movement 

47:24 – How 5 kids in a Belgrade café sparked 50+ revolutions 

48:01 – What Greg Satell has unlearned after two decades of studying change 

54:37 – The power of belief: why “going where the energy is” matters most 

About Greg Satell 

Greg Satell is an internationally recognized expert on transformation, organizational change, and innovation. He is the author of Cascades: How to Create a Movement that Drives Transformational Change and a frequent keynote speaker on leadership in times of disruption. Greg has helped Fortune 500s, global nonprofits, and city governments rethink how they mobilize people and win lasting buy-in for bold ideas. He is known for blending research-backed frameworks with compelling real-world stories, from corporate turnarounds to civic revolutions.  

Resources & Mentions 

• Greg’s website: GregSatell.com 
• Connect with Greg on LinkedIn. 
• Greg’s book: Cascades: How to Create a Movement that Drives Transformational Change 
• IBM turnaround and Lou Gerstner’s management: Who Says Elephants Can't Dance? by Lou Gerstner 
• “Identity” by Francis Fukuyama:  
• PwC research on change fatigue: PwC Global Workforce Hopes and Fears Survey 2022 

Podcast Contact Information: 

Website: www.learnit.com 

Email: [email protected] 

Follow us on LinkedIn and Instagram for more updates. 

The best teams aren’t just about skill, they’re built on clarity, trust, and the science of group dynamics. 

In this episode of The Learn-It-All Podcast, Damon welcomes group dynamics expert Dr. Colin M. Fisher, professor at University College London and author of the new book The Collective Edge. Drawing on remarkable stories from the worlds of jazz, sports, and business, Colin reveals the hidden psychology that keeps teams stuck, and the practical steps leaders can take to foster high-performing, resilient groups. From his unique background as a professional jazz musician to his groundbreaking research on team behavior, Colin removes the myths around teamwork and shares how anyone, from managers to family members, can build better groups, drive innovation, and create a true sense of belonging. 

Get ready for actionable insights you can use to launch teams with purpose, set goals that actually unite people, and transform both work and personal relationships. 

In this episode, you’ll learn: 

• Why most teams get group purpose wrong, and how to launch with clarity and connection 
• The underlying psychology that drives in-group favoritism and how to overcome it for bigger impact 
• The surprising science behind “collective intelligence”, including what truly predicts team success 
• How to set vivid, powerful goals that galvanize teams (and bust the myth of “just working hard”) 
• Why structure matters more than process, and how misdiagnosing this derails even talented groups 
• How social sensitivity and psychological safety fuel innovation, motivation, and creative improvisation 

Timestamps: 

00:00 – The real reason teams fail: hidden group dynamics 

01:43 – Why today’s problems require collective (not just individual) solutions 

03:12 – Colin Fisher’s journey from jazz musician to group dynamics scholar 

05:57 – The “click” moment in group improvisation, and why it matters 

07:52 – Core message of The Collective Edge and its target audience 

11:04 – Are teams or individuals behind today’s breakthroughs? Surprising research results 

13:54 – The hidden teams behind famous leaders, inventors, and tech “geniuses” 

15:53 – The #1 mistake founders make when launching teams 

18:39 – What a “strong launch” looks like (and why daily rituals matter) 

21:08 – Goal clarity: making “vivid” goals that truly align teams 

24:15 – How JFK and Bill Gates set goals that sparked genuine buy-in 

27:43 – Social sensitivity: the ultimate predictor of team performance 

30:28 – How to spot and develop social sensitivity in hiring and team building 

33:44 – Why starting with skills and perspectives matters most 

35:25 – Designing high-impact tasks for authentic collaboration 

38:19 – The real difference between psychological safety and autonomy 

41:23 – Structure vs. process: how to rig the game in your team's favor 

44:28 – Why sports and music teams get structure right (and business leaders rarely do) 

45:06 – The longevity secrets of the Rolling Stones (and what one-hit-wonders miss) 

50:38 – Mythbusting: Does diversity cause conflict? 

52:10 – Mythbusting: Is competition always a motivator? 

56:07 – Why trust falls are overrated, and what builds real collaboration 

59:02 – Final takeaway: build for healthy groups, not just high-performing individuals 

About Colin M. Fisher 

Colin M. Fisher is a professor at University College London and a leading researcher in group and team dynamics, fascinated by how people improvise, collaborate, and build creative solutions in teams. Before academia, Colin was a professional jazz trumpet player, which shaped his understanding of group “flow” and improvisation across language, culture, and experience. Today, he works with organizations, writes for publications, and teaches leaders how to transform everyday groups into high-performing, psychologically safe teams. He’s the author of The Collective Edge, which synthesizes decades of research and real-world stories to help anyone build better groups anywhere. 

Resources Referenced: 

• Colin’s website 
• Colin on LinkedIn 
• The Collective Edge by Colin M. Fisher 
• Research by Stefan Wuchty, Brian Uzzi, and Benjamin F. Jones: “The Increasing Dominance of Teams in Production of Knowledge” 
• Team of Rivals by Doris Kearns Goodwin 
• Jim Collins: Big Hairy Audacious Goals (BHAG) 
• Daniel Pink 
• Adam Grant 
• Annie Duke 
• Amy Edmondson's "The Fearless Organization" 
• The Social Network (film) 

Podcast Contact Information: 

Website: www.learnit.com 

Email: [email protected] 

Follow us on LinkedIn and Instagram for more updates. 

In this powerful episode of The Learn-It-All Podcast, host Damon Lembi digs in with executive coach and Career Benders founder, Angie Callen to reveal why authenticity is a performance tool, how generational dynamics shape workplace trust, and what you—and every leader—can do to rally a motivated, loyal, and thriving team. 

Discover Angie's journey from civil engineering to entrepreneur, her best practices for individual growth plans, and the key conversations every manager should have with their team. From perfectionism and the myth of work-life balance to actionable tools like values exercises and curiosity-driven reflection, this episode is packed with ideas for anyone ready to take ownership of their career and lead with purpose. 

In this episode, you’ll learn: 

• The real reasons employees leave: How generational values and management misalignment fuel the leadership gap. 
• Why authenticity isn’t just a buzzword—and how to leverage it to build trust and team engagement. 
• How self-awareness, journaling, and curiosity can help you find passion and purpose at work. 
• Tips for managing and motivating different team members as individuals, not units. 
• Strategies for middle managers faced with culture clash and organizational resistance. 
• Why executive presence, confidence, and self-reflection are critical in the modern workplace. 

Timestamps: 

00:00 – Why teams aren't motivated by the same things 

01:11 – Study: 64% of employees trust robots more than managers 

02:02 – The generational gap in leadership and communication styles 

03:52 – Why authenticity matters in leadership 

06:41 – Angie's career path: from engineer to entrepreneur 

08:26 – From art galleries to coaching—embracing “career tumbleweed” 

11:32 – Why most people never find passion in their work (and how to start) 

13:20 – Taking ownership of your career trajectory 

14:04 – Tips for small, low-risk career pivots 

15:30 – Using journaling and reflection to clarify your strengths 

17:14 – The leader’s responsibility: motivating and developing teams individually 

19:38 – Simple exercises to get to know your team faster 

23:49 – Coaching frustrated middle managers: tackling organizational roadblocks 

26:32 – The biggest current challenges for today’s leaders 

28:56 – Building confidence through coaching (and why it matters) 

33:48 – Why AI can’t replace human-to-human coaching 

34:05 – How Angie’s coaching style has evolved 

37:58 – Angie’s ideal clients—and her unique coaching philosophy 

41:02 – Must-have free resources for stuck middle managers 

42:05 – Final advice: You have more control over your career than you think 

About Angie Callen 

Angie Callen is a former civil engineer turned executive coach, podcast host, and the founder of Career Benders. With a colorful journey spanning engineering, nonprofit leadership, entrepreneurship, and career coaching, Angie specializes in helping professionals—especially technical leaders—find their authentic path and unlock their leadership potential. Her coaching focuses on self-awareness, confidence, and finding purposeful, aligned work. Angie is known for practical, people-first strategies that inspire growth and real results. 

Resources & Mentions: 

• Career Benders Free Resources – Core Values exercise and other tools mentioned by Angie 
• Angie Callen on LinkedIn 
• Career Benders official website 
• The Modern Coach Co. – For more on Angie’s work with coaches 
• Ikigai concept (More on Ikigai from PositivePsychology.com) 

Podcast Contact Information: 

Website: www.learnit.com 

Email: [email protected] 

Follow us on LinkedIn and Instagram for more updates. 

In this purposeful solo episode of The Learn-It-All Podcast, host Damon Lembi pulls back the curtain on three of the most undervalued leadership skills: the art of consistently showing up, the power of pausing under pressure, and the critical ability to let go and move forward. Damon combines personal anecdotes, practical advice, and frameworks from top experts to help leaders at any level build the resilience and trust needed for high-performing teams—especially in today’s fast-moving, AI-first environment. Whether you’re a new manager or an aspiring executive, you’ll leave with actionable takeaways for leading with presence, poise, and purpose. 

In this episode, you’ll learn: 

• Why showing up—even when you don’t want to—is the backbone of true leadership 
• How “the pause” can defuse tension and change the trajectory of tough conversations 
• The difference between letting go and avoidance—and how leaders can move past mistakes without grudges 
• Simple, science-backed practices to reset after conflicts and stay present for your team 
• How carrying unresolved issues undermines culture and drains team performance 
• Real-world rituals Damon uses to keep his promises and be consistently reliable 

Timestamps: 

00:00 – What most people get wrong about leadership 

00:30 – Why the small, invisible habits build real trust 

01:00 – Skill 1: Show up—even when you don’t feel like it 

01:45 – Why inconsistency breaks trust and erodes culture 

02:20 – Damon’s example: Recording at 7AM on a Sunday 

03:10 – Anchor to purpose when motivation fades 

03:45 – Skill 2: Practice the pause in tough moments 

04:15 – What the body tells you before you snap 

04:45 – Damon’s tip from Cynthia Kane: One breath + ground yourself 

05:30 – Why excited leaders need the pause too 

06:00 – The power of slowing the energy in a room 

06:30 – Skill 3: Learn to let go (without avoiding or resenting) 

07:00 – Mike Robbins’ framework: Let it go or deal with it 

07:30 – Why option 3 (resentment) kills culture 

08:00 – Resetting between meetings and relationships 

08:30 – Recap: Show up, pause, let go 

09:00 – Weekly challenge + free gift: 45 days of Learnit training 

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 & Mentions: 

• Damon Lembi LinkedIn 
• Learnit 
• Learn It All Leader (Book by Damon Lembi) 
• The Learn-It-All Leader for Kids (Kids Book by Damon Lembi) 
• Cynthia Kane’s book: The Pause Principle 
• Cynthia Kane on The Learn-It-All Podcast, Episode 182 
• Mike Robbins’ website: mike-robbins.com 
• Learnit 45-day free training offer

Podcast Contact Information: 

Website: www.learnit.com 

Email: [email protected] 

Follow us on LinkedIn and Instagram for more updates. 

When was the last time you worked ON your business, not just IN it? In this eye-opening episode, host Damon Lembi welcomes Dr. John Hillen—former U.S. Assistant Secretary of State, multi-time CEO, board chairman, and award-winning strategy professor—to break down what strategic thinking actually means for today’s leaders. Drawing from his hot new book, The Strategy Dialogue, John argues that strategy isn’t just for Fortune 500 boardrooms; it’s a muscle every leader can—and must—develop, regardless of company size. From unearthing the difference between “strategic planning” and “strategic thinking” to practical ways to shift your mindset, this episode is packed with actionable frameworks, real-world case studies, and wisdom to help you stop reacting and start leading. 

If you’ve ever felt too busy to look beyond your to-do list, you’ll learn why only 4% of leaders naturally think strategically—and how to join them. Plus: stories from the Berlin Wall, lessons from the rise of Netflix, the fall of Blockbuster, and what grocery stores can teach you about your true strengths. Whether you’re an entrepreneur, executive, or aspiring strategist, this episode will change the way you see your business, your role, and your future. 

In this episode, you’ll learn: 

• What separates strategic leaders from busy taskmasters (and why ownership of strategy can’t be delegated) 
• Why “strategic thinking” is not the same as “strategic planning,” and how to make it a daily habit 
• The 4% mindset: How truly strategic leaders map the ecosystem, spot patterns, and connect the dots long-term 
• Real-life case studies: Why Netflix disrupted Blockbuster, and how Trader Joe’s and Whole Foods each leverage hidden strengths 
• How to identify your company’s core competency (hint: ask your customers, not your marketing team) 
• Tools and frameworks—from SWOT and “TOES” to actionable, Socratic dialogues—for thinking and leading strategically in any environment 

Timestamps:  

00:00 – The “strategic muscle”: why leaders must work ON the business 

00:30 – Damon introduces John Hillen & today’s episode 

01:26 – Why strategy is the heart of leadership 

02:49 – Common excuses leaders use to avoid strategic thinking 

04:51 – Only 4% of executives think strategically (and what the other 96% do instead) 

07:36 – John’s background: Berlin Wall, Desert Storm, and the roots of strategic thinking 

12:14 – How global experience shapes perspective and context 

14:24 – Why John wrote The Strategy Dialogue & teaching strategy through dialogue 

19:14 – Strategic thinking vs. strategic planning: Key differences 

23:36 – Using “scenario planning” and creativity in traditionally rigid industries 

24:51 – The essential mindset shift: think forward, ask better questions 

26:26 – Why companies like Blockbuster and Kodak get disrupted 

30:28 – Netflix’s three business model pivots: lessons in strategic agility 

32:35 – How to get honest about your true strengths—ask your customers 

35:49 – Whole Foods vs. Trader Joe’s: Different strengths, different strategies 

37:21 – Beyond SWOT: the TOES framework for action-oriented strategy 

44:40 – Can AI help with strategic thinking? The human judgment difference 

47:00 – Why “how you think” is more important than “what you decide” 

51:24 – How often should you revisit your strategy? 

58:40 – Strategy, clarity, transparency, and public policy examples 

1:00:10 – John’s final advice: Work on your business, not just in it 

About Dr. John Hillen  

Dr. John Hillen is an award-winning strategy professor, best-selling author, and sought-after business leader with a career spanning the military, government, academia, and boardrooms. A former U.S. Assistant Secretary of State and CEO of multiple companies, John has taught leadership and strategy at Duke, George Mason, and other top universities. His latest book, The Strategy Dialogue, distills decades of experience into practical lessons for leaders at every level. Find out more at johnhillen.com or connect with John on LinkedIn. 

Resources & Mentions: 

• The Strategy Dialogue by John Hillen 
• John’s website: johnhillen.com 
• John Hillen on LinkedIn 
• Patrick Lencioni, author referenced and blurb contributor 
• StrengthsFinder tool mentioned 
• Clayton Christensen and his work on disruptive innovation 

Podcast Contact Information:  

Website: www.learnit.com 

Email: [email protected] 

Follow us on LinkedIn and Instagram for more updates. 

Winning in the remote world isn’t just about logging in—it’s about knowing yourself, mastering communication, and finding where you fit.  

In this episode, Damon Lembi sits down with Michelle Coulson, founder of Remote Rebellion, to crack open the realities of remote and hybrid work. Michelle draws on her years as a recruiter and leader of remote teams to explore what it truly takes to thrive (or hire) in the remote-first era. From cutting through workplace distractions to the psychology of choice, Michelle and Damon address the often-overlooked challenges and opportunities facing both companies and job seekers today. Whether you’re looking to land your first remote job, level-up your virtual team, or simply want a more fulfilling work-life balance, you’ll walk away with actionable strategies, honest insights, and plenty of inspiration to support your remote journey. 

In this episode, you’ll learn: 

• Why freedom of choice is the #1 motivator for remote workers (even before money) 
• The real traits that set top performers apart in remote environments—and why structure still matters 
• Common mistakes organizations make when “going remote” and how to set intentional policies 
• How to stand out in an increasingly competitive remote job market—personal branding, communication hacks, and more 
• What recruiters are really looking for in remote candidates (plus Michelle’s favorite filtering trick) 
• Why authentic networking and feedback fuel both hiring and personal growth in a virtual world 

Timestamps: 

00:00 – Michelle on freedom of choice and productivity 

01:21 – Rethinking the work-life equation 

02:55 – How the Pandemic turbocharged Remote Rebellion 

03:29 – The case for office and remote: pro-choice work life 

04:37 – Bad reasons companies force return-to-office 

05:54 – Helping employers design meaningful in-person work 

07:31 – The hardest part of running a remote-first company 

08:58 – Must-have skills for remote success (communication rules!) 

12:54 – Building effective team communication across cultures 

16:38 – Helping late-career workers go remote 

19:51 – Why remote jobs are so competitive right now 

22:05 – Does remote really make people happier and more productive? 

23:45 – Finding and landing remote roles: personal branding, networking 

28:19 – Michelle’s filtering hack for serious applicants 

30:22 – Why you shouldn’t mass-apply (and how you’re part of the problem) 

33:39 – Can you become a great leader if you’ve only worked remotely? 

36:44 – Michelle’s virtual remote career fair: bringing humanity back 

40:24 – How Michelle helps orgs recruit for remote readiness 

44:55 – Honesty about “remote-first” and setting expectations 

46:22 – Who thrives in Michelle’s Remote Job Academy 

49:13 – The future of remote and hybrid work 

51:32 – The value of external feedback and keeping a success journal 

54:29 – Where to connect with Michelle 

About Michelle Coulson 

Michelle Coulson is the founder of Remote Rebellion, a company dedicated to empowering individuals to design their work around life—rather than the other way around. With a background in recruitment and having managed remote, cross-continental teams, Michelle specializes in helping both organizations and job seekers master remote work. Her practical, candid approach cuts through the noise, offering real-world insights on talent attraction, communication, and what it actually takes to succeed virtually. Michelle has also hosted global remote job fairs and leads her own Remote Job Academy.  

Resources & Mentions 

• Remote Rebellion website 
• Michelle Coulson on LinkedIn 
• Learnit: www.learnit.com 

Podcast Contact Information: 

Website: www.learnit.com 

Email: [email protected] 

Follow us on LinkedIn and Instagram for more updates. 

How would your life change if you realized your greatest power isn’t what happens to you—but how you choose to think about it? In this eye-opening episode, Damon sits down with world-renowned mental toughness coach Chris Dorris to unpack the real meaning of mental mastery. Chris shares why our states—and ultimately our lives—are shaped by the content we choose to fill our minds with. Through engaging exercises, candid stories, and actionable mantras, Chris reveals how to break free from victimhood, conquer self-doubt, and start creating your best days on purpose. 

Listeners learn why most of our suffering is learned—not inevitable—and why unlearning is the true path to excellence. Whether it’s overcoming imposter syndrome, rewiring how you respond to adversity, or empowering those around you to ditch the blame game, this episode is packed with the tools, mindsets, and mantras to help you close the gap between the life you have and the life you want. 

In this episode, you’ll learn: 

• Why “create the state, don’t wait” is the key to lasting happiness and performance 
• How your thoughts instantly shape your moods—and simple exercises to prove it 
• The origins of victim mentality and how to break free from it (for yourself and others) 
• The power of “Catch, Own, Replace”: a framework to shift from low to high-grade thinking 
• How visualization and mental rehearsal rewires your brain for success—no matter your circumstances 
• What the “success story folder” is, and how to use it to build belief and confidence on tough days 

Timestamps: 

00:00 – Chris’s “Best Damn Day of My Life” ritual and the science of choosing your mood 

03:56 – Real-time exercises: moving yourself across the emotional spectrum 

08:58 – Why mental toughness is about unlearning and the story of “Benny and the Car Keys” 

15:42 – How to catch, own, and replace sabotaging thoughts 

20:44 – Visualization, neuroscience, and the POW golfer story 

25:54 – Why complaining is the enemy—and what people get from victimhood 

28:53 – Breaking out of the blame game: stories, strategies, and permission 

33:20 – The flat tire lesson: responding to setbacks with mastery 

43:20 – Creating excellence from everything—Damon’s personal story with adversity 

54:38 – Why wishing on birthday candles is a waste: teaching kids to “decide” 

56:24 – Recap: the habits and mantras of mental mastery 

58:45 – The “Success Story Folder”: what it is and how to start yours 

59:05 – How to connect with Chris and access more mental toughness tools 

About Chris Dorris 

Chris Dorris is a globally acclaimed mental toughness coach, author, and performance consultant who has dedicated his career to helping people close the gap between how life is and how they want it to be. As a coach to elite athletes, business leaders, and high-achievers, Chris’s impact has reached millions through his books, daily mental mastery tips, and engaging seminars. His actionable philosophy centers on unlearning limiting beliefs, cultivating emotional mastery, and equipping individuals to create excellence in every aspect of their lives.  

Resources & Mentions 

• Chris Dorris’s website: ChristopherDorris.com 
• Chris Dorris on LinkedIn: https://www.linkedin.com/in/chrisdorris/ 
• Daily Dose Mental Toughness Tips: ChristopherDorris.com/DD 
• The Book of Mental Toughness Mantras by Chris Dorris: order here 
• Byron Katie’s Work: thework.com 
• Steve Chandler Audio on Victim vs. Ownership Mindset: Listen here 

Podcast Contact Information: 

Website: www.learnit.com 

Email: [email protected] 

Follow us on LinkedIn and Instagram for more updates.