Episodes

  • Trust, Crisis & Why Elon Left Money on the Table

    Trust, Crisis & Why Elon Left Money on the Table
    Mar 31 2026
    Spencer Penn evacuated his engineer from Ukraine the day before Russia invaded. What he did next — and why it worked — reveals more about leadership trust than most books on the subject. Penn is CEO and co-founder of LightSource, a procurement AI company that grew from two people in a garage to 64 employees. In this episode, he traces the company's origin to a $30 billion problem he watched firsthand at Tesla — car parts sourced via spreadsheets and email — and the moment he hired a Ukrainian developer off GitHub who would later need to get out of the country overnight. Penn and Felicia Shakiba debate whether Elon Musk could have been even more successful with a different leadership approach, what separates mature from immature leadership mindsets, and a reframe on strengths that most leaders get completely backwards: the capability that comes easiest to you is almost certainly your highest ROI — and most people are blind to it. Chapters: 00:00 The Genesis of LightSource 04:35 Finding the First Believers 14:45 Building Trust Through Adversity 19:15 The Gift of Opportunity 21:54 Balancing Leadership Decisions 24:15 The Importance of Values in Leadership 25:58 New vs. Experienced Leaders 29:15 The Complexity of Leadership Traits 31:55 The Impact of Leadership Style 36:30 Strengths vs. Weaknesses in Leadership Subscribe to the LeaderbookAI Podcast for conversations with leaders shaping the future of work, leadership, and AI. Subscribe to the LeaderbookAI Brief: https://leaderbookai.substack.com/ 🎧 Listen to the podcast: https://leaderbook.ai/podcast We create high-performing powerhouses. Let's talk: https://leaderbook.ai/contact Connect with Felicia on LinkedIn: https://www.linkedin.com/in/feliciashakiba
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    47 mins
  • How to Find AI Unicorns Before Everyone Else

    How to Find AI Unicorns Before Everyone Else
    Mar 24 2026
    How do top venture capitalists find AI unicorns early? In our 100th episode 1-hour special, Marina Davidova, Managing Partner at Silicon Valley's DVC, shares how her team uses AI agents, community-driven diligence, and sharp founder pattern recognition to identify breakout startups before the market catches up. From repeat founders and engineering mindset to distribution, adaptability, and founder energy, this conversation reveals what VCs are really looking for — and how AI is changing the investment process. Chapters 00:00 How should venture firms automate with AI? 00:48 Why Marina believed in AI early 03:42 Moving to Silicon Valley and standing out as an investor 06:31 Four unicorns in four years 08:49 What Marina looks for in unicorn founders 12:49 Can entrepreneurial mindset be taught? 15:18 How DVC’s investor community drives the funnel 18:27 How AI agents screen startup deal flow 20:24 What happens in the community discussion process 25:05 Red flags, green flags, and difficult decisions 29:31 The founder who looked perfect on paper 31:17 Adaptability vs. consistency in startups 34:32 How fast DVC makes investment decisions 37:26 What founders actually spend early rounds on 41:42 The patterns Marina sees in breakout founders 45:46 Why some technical founders struggle to sell 48:00 The responsibility of choosing future AI leaders 52:13 Why founders need a trusted tribe Subscribe to the LeaderbookAI Podcast for conversations with leaders shaping the future of work, leadership, and AI. 🎧 Listen to the podcast: https://leaderbook.ai/podcast We create high-performing powerhouses. Let’s talk: https://leaderbook.ai/contact
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    58 mins
  • The AI Transformation Most Leaders Get Wrong

    The AI Transformation Most Leaders Get Wrong
    Mar 17 2026
    What does it really take to lead a successful AI transformation inside an organization? Many companies focus on implementing AI tools. But according to Glenn Mathis, Former CEO of Integris, the real challenge isn’t technology — it’s trust, clarity, and culture.
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    31 mins
  • The Biggest Mistake Revenue Leaders Make With AI

    The Biggest Mistake Revenue Leaders Make With AI
    Mar 10 2026
    What’s the biggest mistake revenue leaders make with AI? Companies everywhere are racing to automate sales—research, outreach, forecasting, and pipeline management. But according to JD Miller, many organizations are about to make a critical mistake: automating processes that were already broken. JD Miller, CRO Operating Partner in Residence at Rothschild & Co. / Five Arrows Capital, shares how private equity-backed companies should approach AI in sales, why trust and human connection still drive revenue, and how leaders can experiment with AI without increasing risk. His conclusion: AI should make sellers more human—not replace them. ⸻ Chapters 00:00 The Role of AI in Sales Transformation 08:26 Measuring AI’s Impact on Revenue 13:23 Real-World Applications of AI 21:18 Leadership’s Role in AI Adoption ⸻ Subscribe to the LeaderbookAI Podcast: https://leaderbook.ai/podcast We create high-performing power houses. Let’s talk: https://leaderbook.ai/contact
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    35 mins
  • AI Trained on Love

    AI Trained on Love
    Mar 3 2026
    Can AI learn love—or at least empathy? Cory Lopes-Warfield, CEO of Lovings, shares his unconventional founder journey from homelessness and hospitality to building Lovings AI. We discuss Nova, an AI agent trained to respond from a “love” framework, and what empathetic AI really means in practice. Cory explains the real risks of AI, how agents are reshaping entrepreneurship, and why the future may belong to leaders who combine human judgment with intelligent machines. Chapters 00:00 Introduction and Personal Background 00:46 The Journey from Homelessness to Entrepreneurship 07:29 Transitioning to Tech and Learning to Code 12:45 The Concept of Empathetic AI 17:49 The Development of Nova and Its Unique Features 26:21 Growth Strategies and Future Vision 28:44 The Philosophy of Love in AI Subscribe to the LeaderbookAI Podcast: https://leaderbook.ai/podcast We create high-performing power houses. Let’s talk: https://leaderbook.ai/contact
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    35 mins
  • How the President of LA Galaxy Wins

    How the President of LA Galaxy Wins
    Feb 23 2026
    How do leaders turn a struggling organization into a winning culture? Tom Braun, President & COO of the LA Galaxy, shares the leadership decisions behind rebuilding one of MLS’s most iconic clubs. He explains how trust, authenticity, and small operational wins helped restore momentum with players, staff, and fans. This episode explores what sports leadership can teach CEOs about culture, alignment, and driving performance under pressure. Chapters 00:00 From Investment Banking to Sports Leadership 06:59 Authenticity in Leadership 10:47 Rebuilding Momentum and Fan Experience 18:16 Building Trust and Community Engagement 20:27 Investing in Youth Development 25:13 Creating a Memorable Fan Experience 28:14 LeaderbookAI_Outro.mp4 — Subscribe to the LeaderbookAI Podcast: https://leaderbook.ai/podcast We create high-performing power houses. Let’s talk: https://leaderbook.ai/contact
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    31 mins
  • LeaderbookAI Trailer

    LeaderbookAI Trailer
    Feb 5 2026
    AI automation and leadership that creates value. Join Felicia Shakiba on LeaderbookAI (formerly CPO PLAYBOOK) for candid conversations with CEOs, executives, investors, and innovators who are making the decisions that matter. From timeless leadership principles and decision-making frameworks to cutting-edge AI automation strategies—this podcast gives you the insights you need to lead with confidence. Whether you're navigating leadership challenges, evaluating investment opportunities in private equity, implementing business process automation, or building your organization's strategy around machine learning and emerging technologies, you'll find practical diagnostics and real-world wisdom here. Some episodes focus on core leadership. Others dive deep into AI automation and how technologies like generative AI are reshaping business. All of them deliver actionable value for leaders and investors. Real insights. Real results. Real talk about what drives business success. New episodes weekly.
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    Less than 1 minute
  • Alignment in Action: Introducing LeaderbookAI

    Alignment in Action: Introducing LeaderbookAI
    Jan 20 2026
    What does real alignment look like—when leadership, strategy, and execution finally match? In this bonus episode, Felicia Shakiba shares an important update: CPO PLAYBOOK is becoming LeaderbookAI. This isn’t just a podcast name change—it reflects the evolution of the entire business. Episode 95 explored the cost of misalignment inside organizations. Here, we practice what we preach. LeaderbookAI represents the expanded work behind the show today: AI-enabled transformation, value creation planning for private equity and investors, world-class executive coaching, M&A integration, compensation and organizational design, and leadership development directly tied to business outcomes. Felicia also thanks the listeners who’ve helped build this show into the top 6% of podcasts worldwide, as it approaches 100 episodes and prepares for Season 5. Same conversations. Same rigor. A name that finally matches the impact. Welcome to LeaderbookAI.
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    3 mins