In this high-energy episode of The Learn-It-All Podcast, host Damon Lembi is joined by John Golden, Chief Strategy and Marketing Officer at Pipeline CRM and host of the SalesPop podcast. Together, they dig deep into the art of decision-making, the power of authenticity in leadership, and the lessons learned from the dot-com era—offering actionable advice for anyone looking to future-proof their business or career. John shares personal stories about trusting his gut, being deliberate with growth, and why admitting you don't know is the ultimate mark of expertise. From the importance of resilience and learning from mistakes, to navigating VC/PE relationships and thriving in an AI-driven world, this episode is packed with wisdom for founders, leaders, and ambitious professionals alike. 

In this episode, you’ll learn: 

• Why authenticity—not bravado—is the key to earning trust as a leader 
• How to assess “the why” behind big career or business decisions (and how John’s gut instinct saved him from a bad move) 
• What founders and business leaders today can learn from the triumphs and failures of the dot-com boom and bust 
• Smart, intentional ways to grow your company without overextending (including when and how to bring on VC/PE partners) 
• Why being willing to admit mistakes—and learn from them—sets the best leaders apart 
• How “fractional” and contractor talent can turbocharge your business without risky overhead 

Timestamps 

00:00 – The power of admitting mistakes and authentic leadership 

01:09 – Why you’re never 100% ready: advice for big leaps 

03:46 – When “the why” isn’t strong enough: a dot-com era cautionary tale 

07:01 – Should you take the “wrong” job just to pay the bills? 

08:08 – John’s move to Silicon Valley: seizing unexpected opportunities 

09:34 – Lessons from the dot-com boom and bust (and AI parallels) 

14:58 – Practical advice for founders: bootstrapping, VC/PE diligence, and controlled growth 

18:37 – Balancing gut instinct with due diligence 

20:56 – Leveraging fractional, contract, and remote talent strategically 

22:51 – John’s pivotal career moment: setting your sights on the CEO role 

25:01 – Why (and how) people limit their own potential 

27:54 – Overcoming fear of failure—and fear of success 

29:29 – Imposter syndrome and why you should apply for the job anyway 

30:27 – The value of authenticity (and how to show it as a leader) 

32:20 – Failing forward: why mistakes are fuel for growth 

33:58 – The value of humility and vulnerability in leadership 

35:11 – Where to connect with John and find SalesPop 

About John Golden 

John Golden is the Chief Strategy and Marketing Officer at Pipeline CRM and the host of SalesPop, a podcast with over 1,500 episodes featuring top leaders and sales innovators. With a distinguished background in sales strategy and executive leadership, including experience navigating the boom and bust of Silicon Valley’s dot-com era, John is known for his candid, authentic approach to business. He specializes in helping founders and business leaders future-proof their organizations by building on solid fundamentals, leveraging gut instinct, and hiring resilient, authentic teams.  

Resources Referenced 

• Pipeliner CRM 
• SalesPop Podcast 
• SalesPop on YouTube 
• John Golden on LinkedIn 

Podcast Contact Information: 

Website: www.learnit.com 

Email: [email protected] 

Follow us on LinkedIn and Instagram for more updates. 

What separates good leaders from truly transformative ones? In this powerful full-episode conversation, Damon welcomes Ken Gavranovic—seasoned tech executive, Thinkers50 honoree, and serial builder of billion-dollar businesses—to The Learn-It-All Podcast for a no-holds-barred exploration of leadership, entrepreneurship, and the future of work in the AI era. Ken unpacks his unique path from humble beginnings to leading 18 exits and owning $3B in P&L, revealing how the world’s best leaders don’t just excel individually—they elevate everyone around them. From the lessons hidden inside failed startups to why AI is redefining the playing field, this episode is overflowing with hard-won wisdom, tools, and real talk for leaders who want to level up themselves and their teams. 

Packed with actionable advice, personal stories, and candid reflections, this episode is your blueprint for becoming not just a high performer, but a meta performer—one who inspires, coaches, and wins with others. Whether you’re scaling a startup, transforming a legacy business, or aspiring to lead with more impact, you’ll leave fired up and equipped to turn learning into lasting results. 

In this episode, you’ll learn: 

• What it means to be a “meta performer”—and how great leaders elevate entire teams, not just themselves 
• How Ken went from scrappy founder to building a $200M company from the ground up 
• The critical difference between measuring outcomes vs. activity (and how to actually set targets that drive results) 
• Why money alone won’t make you happy—and what true success and options look like as a leader 
• How to ask better questions, foster a culture of feedback, and avoid becoming a bottleneck as you scale 
• What AI means for every business: why it’s a massive equalizer, and how to find quick wins (without making million-dollar mistakes) 
• The career-defining lessons you’ll learn at a failed startup (that big companies can’t teach you) 

Timestamps: 

00:00 – How “meta performers” level up those around them 

00:33 – Welcome to the Learn-It-All Podcast: About Ken and what’s ahead 

01:43 – Ken’s first questions when starting something new 

02:19 – The childhood experiences that shaped Ken’s entrepreneurial drive 

05:33 – Money, happiness, and the real options of wealth 

07:44 – What mentors look for: Grit, honesty, and taking care of others’ capital 

08:25 – Building Web.com from scratch: The inside story 

11:33 – Mistakes of the dot-com era (and lessons for AI today) 

14:51 – Why neither “experience” nor youth guarantee right answers 

17:13 – Outcomes vs. activity: How busywork derails companies 

18:08 – Measuring results at New Relic: Asking the right questions 

21:16 – How to coach with questions instead of answers 

22:35 – Moving from high performer to meta performer (and why it matters) 

25:18 – Elevating your team: From leadership to “teamship” 

27:23 – Is it the product or the people? How Ken evaluates startups and investments 

31:37 – AI’s disruptive power, past and future: What’s next for leaders 

35:02 – AI, jobs, and the future of work 

40:19 – How to start leveraging AI today (without melting down your org) 

43:24 – The power of prompt engineering for every professional 

46:49 – The future of leadership—and why vision still sets winners apart 

48:18 – The best career risk advice for aspiring founders 

50:18 – The one thing you need with data to run your business well 

51:13 – Where to connect with Ken and closing thoughts 

About Ken Gavranovic 

Ken Gavranovic is a renowned technology executive, global keynote speaker, and a member of Thinkers50. He built Web.com from scratch to $200 million in revenue and has led 18 successful exits, overseeing $3 billion in P&L. Ken’s leadership at companies like New Relic and Cox Automotive have helped scale products and organizations to global prominence. Known for his passion for elevating teams and building winning cultures, Ken is also an active advisor, investor, and advocate for data-driven, people-first leadership. 

Resources & Mentions: 

• KenGavranovic.com 
• Ken on LinkedIn 
• Book: Amp It Up by Frank Slootman 
• Book: Never Eat Alone by Keith Ferrazzi 
• Thinkers50: Thinkers50 
• New Relic: New Relic 
• Book (referenced): Small Ball, Big Results by Joel Goldberg 
• The Learn-It-All Podcast with Doug Conant 
• The Learn-It-All Podcast with Stephen M.R. Covey 
• The Learn-It-All Podcast with Richard White 
• The Learn-It-All Podcast with Keith Ferrazzi 

Podcast Contact Information: 

Website: www.learnit.com 

Email: [email protected] 

Follow us on LinkedIn and Instagram for more updates. 

Successful teams rely on energy, resilience, and community—and middle managers need all three now more than ever. In this practical solo episode, host Damon Lembi shares game-changing strategies for navigating the toughest seat in business: the middle. Drawing inspiration from a chaotic day at his son’s nursery school, Damon unpacks the real-world stressors facing today’s middle managers and delivers three essential tips you can start using immediately. From protecting your sleep to reimagining meetings, plus a surprising approach to building your own peer support circle, this episode is packed with mental, physical, and tactical tools to help you thrive—not just survive. Damon also shares a bonus “book of wins” exercise to keep your motivation high against all odds. 

Whether you’re feeling overwhelmed, burnt out, or just looking to sharpen your leadership edge, you’ll find tangible steps and inspiration right here. 

In this episode, you’ll learn: 

• Why self-care is the first and most critical step for every middle manager’s success 
• How a structured “3-2-1” evening routine can boost your sleep—and next-day performance 
• Simple but powerful meeting habits that drive clarity, manage time, and energize your team 
• How to create your own peer community for insights, support, and resilience 
• The surprising effect of reflecting on your wins—and how to build a practice that fuels you through challenges 

Timestamps: 

00:00 – The middle manager paradox: pressure from above, responsibility below 

00:30 – Why middle managers are often overlooked—but absolutely essential 

01:05 – Tip #1: Clarify your priorities (especially when they’re unclear) 

01:45 – Damon’s morning habit: setting his “Big 3” 

02:15 – How clarity protects your time, team, and sanity 

02:50 – Tip #2: Know how your boss defines success 

03:25 – The misalignment trap: working hard on the wrong things 

04:10 – Pro tip: Ask “What’s the #1 thing you need from me this week?” 

04:40 – Tip #3: Lead your team how they want to be led 

05:15 – Story: learning to adapt for a direct report with a hearing difference 

06:00 – “Chameleon leadership” and psychological safety 

06:45 – Recap: Clarify priorities, align with your boss, flex to your team 

07:10 – Damon’s challenge: Pick one tip and try it this week 

07:30 – Free training gift + Learnit.com plug 

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) 
• James Laughlin’s forthcoming book: Habits for High Performers 
• James Laughlin on LinkedIn 
• Mamie Kanfer Stewart on LinkedIn 
• 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. 

In this inspiring episode of The Learn-It-All Podcast, Damon sits down with Ed Hajim—Wall Street veteran, philanthropist, and author—to uncover the extraordinary journey that took Ed from foster homes and orphanages to the helm of major institutions. Ed shares his hard-won lessons on leadership, resilience, and the transformative power of trust and gratitude. Through candid storytelling, he reveals the mindset shifts that propelled him forward, the role creativity and self-awareness play in lasting leadership, and why giving back is the ultimate personal reward. Whether you’re a seasoned exec or just starting your professional path, this conversation is packed with wisdom on overcoming adversity, developing future-ready skills, and leading with heart. 

In this episode, you’ll learn: 

• Why “Who am I?” is the essential question for every leader—and how to start answering it 
• How adversity in Ed’s childhood forged his resilience and leadership philosophy 
• The difference between leadership in the military versus the business world 
• Why trust and gratitude aren’t just feel-good values but practical tools for success 
• How to turn early setbacks into lifelong fuel for growth 
• Actionable ways leaders can shape a culture of creativity and care—no matter the size of the organization 
• The surprising power of giving back, both at work and in your community 

Timestamps: 

00:00 – Ed on trusting people—and learning from being let down 

01:21 – The most important question: Who are you? 

03:58 – Are leaders born or made? Ed’s journey to discovering leadership 

09:08 – Ed’s remarkable childhood: orphanages, foster care, and early adversity 

13:49 – How Ed learned to forgive and love his imperfect father 

17:51 – Turning disadvantage into advantage: adaptability & resilience 

18:07 – What kept Ed from a “victim mentality” and on a positive path 

20:07 – The shift from mistrust to radical trust in business 

22:51 – Lessons from military service: building teams, discipline, and personal growth 

24:07 – Leading when you’re younger or less experienced than your team 

26:32 – Military vs. business leadership: the power of thinking outside the box 

27:51 – How Ed fosters creativity and innovation as a leader 

31:08 – The secret to culture, strategy, people, and knowing your weaknesses 

32:17 – Deflecting credit and the power of gratitude in leadership 

34:35 – On never blaming others and embracing early failure as a gift 

36:09 – Turning mistakes into learning and the dangers of playing the victim 

41:56 – Ed’s fable “The Island of the Four Ps” and why leadership lessons stick as stories 

45:15 – Why passions shift—and how to keep evolving 

47:30 – How Ed helped his kids develop grit (despite privilege) 

51:11 – What still excites Ed every day: purpose after success 

52:32 – The unexpected impact of being rejected from a golf club 

54:11 – The joy and impact of giving back: scholarships and community 

57:31 – Ed’s four realms of life: self, family, work, and community 

60:04 – What’s next for Ed Hajim—and his campaign for practical education 

63:04 – Where to connect with Ed and get his books 

64:02 – Final thoughts: Helping others see their own greatness 

About Ed Hajim 

Ed Hajim is a celebrated Wall Street veteran with more than 50 years of leadership experience. Despite a turbulent childhood spent in foster care and orphanages, Ed rose to become the chairman of the University of Rochester’s board, where he made the single largest donation in school history. Over his multifaceted career, Ed has led top investment firms, authored two acclaimed books (“On the Road Less Traveled” and “The Island of the Four Ps”), and become a passionate advocate for mentorship and community giving. His remarkable journey is a testament to resilience, lifelong learning, and the belief that anything is possible with the right mindset. 

Resources & Mentions: 

• Ed Hajim's Website 
• Ed Hajim on LinkedIn 
• On the Road Less Traveled by Ed Hajim 
• The Island of the Four Ps by Ed Hajim 
• Doug Conant (Leadership reference) 
• Tom Mendoza (NetApp leadership reference) 
• Harvard Business School Alumni Association 
• Growth Fund of America 

Podcast Contact Information: 

Website: www.learnit.com 

Email: [email protected] 

Follow us on LinkedIn and Instagram for more updates. 

In this dynamic episode of The Learn-It-All Podcast, host Damon Lembi welcomes serial entrepreneur and AI expert Didi Azaria, co-founder of Sisense and current CEO of Workiz. Together, they unpack why leaders must resist the urge to chase every shiny object and instead get obsessed with their niche. Didi shares hard-earned lessons on niching down, building execution-driven teams, and how leaders can leverage AI as a force multiplier—without losing their company’s humanity. Packed with actionable stories and candid reflections, this episode is a roadmap for anyone ready to thrive amidst rapid technological change. 

From strategic focus to the practical application of AI, Didi reveals the habits that separate reactive leaders from proactive innovators. Whether you’re running a tech unicorn or a local field service business, you’ll find plenty of inspiration to start moving, iterate fast, and never stop learning. 

In this episode, you’ll learn: 

• The case for “movement over perfection”—why you must build momentum before you know the full plan 
• How to embrace and implement AI as a leadership superpower, not just a productivity tool 
• Didi’s journey from tinkering with modems at 13 to scaling Sisense into a unicorn (and what he’d do differently next time) 
• The power of niching down: why saying “no” is the hardest and most important skill for entrepreneurs 
• How to build a culture where radical feedback and innovation bubble up 
• Why relentless execution (not just brilliant ideas) is the true driver of success 

Timestamps: 

00:00 – Why movement trumps waiting: Build momentum first 

01:47 – Didi’s bets on the future of AI and business 

04:18 – How leaders should respond to FOMO and tech overwhelm 

07:42 – Didi’s entrepreneurial journey: from modems to Sisense 

13:50 – The real cost of missed calls for field service companies 

15:13 – Lessons from scaling Sisense: niching down for growth 

17:44 – The power and challenge of saying “no” as a founder 

20:19 – How self-awareness shapes Didi’s leadership approach 

23:20 – Creating a culture where feedback and candor flow 

25:15 – Harnessing frontline feedback to drive innovation 

26:57 – Why execution beats ideas—and how to fail fast 

29:51 – “Never give up”—but always be willing to iterate 

30:05 – From overthinking to shipping fast: How Didi’s approach has evolved 

31:29 – Getting unstuck: Breaking big goals into action 

34:51 – AI empathy in action: Stories from the frontline 

40:58 – Final reflections: The importance of curiosity and finding your niche 

About Didi Azaria 

Didi Azaria is a serial entrepreneur, AI evangelist, and business leader with a passion for leveraging technology to solve real-world problems. As co-founder of Sisense, he helped scale the company into a data analytics unicorn, earning recognition as an AI patent-holder and visionary in the space. Now, as CEO of Workiz, Didi is revolutionizing the field service industry through automation and AI, empowering small businesses to compete on a whole new level. Known for his transparency and hands-on leadership, Didi distills decades of experience into actionable insights for leaders navigating change. 

Resources & Mentions 

• Didi Azaria on LinkedIn 
• Workiz website 
• Sisense  

Podcast Contact Information: 

Website: www.learnit.com 

Email: [email protected] 

Follow us on LinkedIn and Instagram for more updates. 

In this episode of The Learn-It-All Podcast, Damon welcomes digital transformation leader Tariq Munir to demystify what it really takes to future-proof your business in the age of AI. Drawing from his impressive background leading transformations at giants like PwC and PepsiCo, Tariq reveals why successful change is less about technology—and all about people, mindset, and culture. Together, they uncover the keys to becoming an AI-ready organization, share actionable strategies from Tariq’s new book Reimagine Finance, and explain why finance teams are uniquely positioned to drive game-changing innovation. Whether you’re a CFO, people leader, or aspiring digital change agent, this episode is a playbook for leading transformation that lasts. 

From navigating automation bias to fostering a growth mindset, you’ll learn real-world tactics that move your organization beyond buzzwords—and into continuous improvement. Plus, Tariq delivers hard-won advice for anyone ready to shift from back-office number cruncher to strategic business partner. 

In this episode, you’ll learn: 

• Why mindset (not just technology) is the true driver of sustainable digital transformation 
• Tariq’s definition of “AI readiness” (and why big budgets aren’t required to start) 
• The five principles from Tariq’s transformation playbook that every finance leader should know 
• How to overcome common traps like automation bias and the “highest paid person in the room” effect 
• Why today’s top CFOs are moving beyond accounting to become change agents and business co-pilots 
• The skills and career experiences future leaders will need to thrive in the era of constant change 

Timestamps: 

00:00 – Why behavior and mindset matter most in transformation 

00:26 – Welcome and Tariq’s intro & background 

01:43 – Transformation isn’t about tech—mindset and culture come first 

03:16 – What does “AI ready” actually mean for organizations? 

07:46 – Tariq’s journey and why finance is ripe for innovation 

11:23 – Blueprint: Building a new finance organization from scratch 

12:55 – Lessons learned (and assumptions challenged) from writing his book 

15:35 – Tariq’s five-principle transformation playbook 

16:38 – Two questions every leader asks about change 

21:03 – Why it’s critical to start with “why”—not just action 

23:31 – The unique vantage point of CFOs and why they should lead transformation 

29:01 – The rising importance of critical thinking 

30:19 – Parsing automation bias and urgency traps 

33:19 – Balancing gut instinct with a data-driven discipline 

36:16 – How to keep the “highest paid person in the room” from hijacking innovation 

38:51 – From “I” and “T” profiles to “M” profiles—future leader development 

48:20 – The one section of the book everyone should read 

50:27 – How to instantly boost your confidence and become a translator between business and technology 

51:36 – The evolving CFO: Finance + operations in the next 2-3 years 

53:25 – Final advice: Shift from a victim mentality to an ownership mindset with AI 

57:43 – Where to find Tariq Munir and Reimagine Finance 

About Tariq Munir 

Tariq Munir is a digital transformation expert with over 20 years’ experience guiding global companies—including PwC, AkzoNobel, and PepsiCo—in harnessing data and artificial intelligence to drive profit, boost efficiency, and spark organizational change. After rising through finance roles at multinationals, Tariq now focuses on helping CFOs and business leaders elevate from transactional thinking to strategic transformation. His approach: blending deep domain expertise with a passion for developing people and culture as the real sources of sustainable advantage. He is the author of Reimagine Finance: The CFO’s Leadership Playbook for the Age of AI, Data, and Digital. 

Resources & Mentions: 

• Website: https://tariqmunir.me 
• LinkedIn: Tariq Munir on LinkedIn 
• Book: Reimagine Finance: The CFO’s Leadership Playbook for the Age of AI, Data, and Digital 
• Simon Sinek’s Start With Why (link) 

Podcast Contact Information: 

Website: www.learnit.com 

Email: [email protected] 

Follow us on LinkedIn and Instagram for more updates. 

Success in leadership (and on the field) isn’t just about innovation or stats—it’s about authenticity, trust, and knowing how to bring people along for the ride. 

In this inspiring conversation, Damon sits down with Jennifer Langton, former Senior Vice President of Player Health and Innovation at the NFL, to explore how bold leadership, relentless curiosity, and being your authentic self can move mountains—even when you’re the outsider in the room. Jennifer shares battle-tested lessons from breaking barriers as a young athlete, leading game-changing health initiatives, rolling out transformative technology, and championing both personal and organizational growth. Whether you’re launching big changes like AI or stepping into your first management role, this episode is packed with actionable insights on leading with conviction, leveraging difference as strength, and always learning. 

In this episode, you’ll learn: 

• How Jennifer built unshakeable confidence by embracing her unique story, even when she felt like an outsider 
• What to do when you’re leading experts—without being one yourself (and why asking “outsider” questions is powerful) 
• Jennifer’s “Langton Roadmap” framework to align your strengths with your organization’s mission and make bold career moves 
• The secret to driving behavioral change and technology adoption inside large, legacy organizations (think: NFL, Viacom, Atari) 
• How to overcome fear and resistance around AI—by putting people at the center of digital transformation 
• What sports taught Jennifer about leadership, resilience, and identity—and how those lessons shaped her personal and professional journey 

Timestamps: 

00:00 – Jennifer’s philosophy: Solve with a human-centered approach 

01:32 – Breaking barriers: Jennifer’s all-boys lacrosse story 

04:58 – How to earn trust as a new/younger leader 

06:44 – What happens if you’re not authentic 

08:00 – Using difference as strength when you’re the outsider 

11:47 – Confidence and asking the “right” questions 

13:56 – Recovering from setbacks: injury and loss 

17:40 – The Langton Roadmap: a framework for career growth 

22:14 – Driving behavior change with technology in large orgs 

24:35 – Using pilots and feedback to roll out innovations 

33:48 – Building the NFL Digital Athlete and leading without being a subject matter expert 

38:22 – Why you don’t have to have all the answers—just be curious 

40:41 – Advice for parents about kids in sports and navigating risk 

44:31 – Leaving the NFL: Reflections and the power of impact 

46:36 – Serving clients as a keynote speaker and consultant 

50:28 – The jaw-dropping power of AI in health and sports 

52:50 – Addressing fears about AI and how to bring people along 

56:10 – Final lesson: Be yourself—it’s your greatest leadership tool 

About Jennifer Langton 

Jennifer Langton is an award-winning strategic executive with extensive leadership experience. As CFO of Atari to Senior Vice President of Innovation at the NFL, Jennifer has driven transformative initiatives with measurable impact. Most recently, as SVP of Player Health and Innovation at the NFL, Jennifer spearheaded groundbreaking advancements in athlete safety and performance, setting a new standard in football that will impact other sports and industries.Now, Jennifer is committed to inspiring others through keynote speeches at prestigious events and offering advisory services that empower individuals and organizations to embrace innovation, inspire change, and lead with purpose. Her mission is to harness emerging technologies and navigate complexities, paving the way for transformative innovation in sports and beyond. 

Resources Referenced: 

• Jennifer Langton’s website: jenniferlangtoninc.com 
• Jennifer Langton on LinkedIn: linkedin.com/in/jenniferlangton 
• NYU Langone Health: Concussion Center (referenced contextually for resources about concussions and athlete health) 
• For more on youth sports safety: CDC Heads Up Initiative 

Podcast Contact Information: 

Website: www.learnit.com 

Email: [email protected] 

Follow us on LinkedIn and Instagram for more updates. 

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.