The AI Transformation Most Leaders Get Wrong

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

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.

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

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

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

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.

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.

What if your growth problem isn’t your product, pricing, or team—but misalignment? We’re joined by Dr. Philippe Bouissou—Apple alum, bestselling author of Aligning the Dots, and the mind behind the A4 Precision Alignment™ methodology that’s fueling faster, more sustainable revenue growth for companies around the world. With a PhD in chaos theory and a resume that includes scaling Apple’s eCommerce from zero to $350M under Steve Jobs, Philippe has spent 30+ years advising CEOs, investing $44M in startups, and sitting on 23 boards. He’s the founder of Blue Dots Partners, where he and a team of elite CEOs decode growth through alignment. Chapters 00:00 The Pressure of Growth: Understanding Misalignment 03:01 The Core of Growth: Alignment with Target Market 06:01 Dimensions of Alignment: Addressing Customer Pain 09:01 Perception vs. Messaging: The Communication Gap 12:02 Frictionless Transactions: The Buying Process 14:59 Delivering Delight: The Customer Experience 17:50 Diagnosing Misalignment: The CEO's Challenge 20:55 The Importance of Internal Alignment 23:51 First Steps to Realignment: A Practical Approach 26:59 Understanding Market Truth: The Customer's Perspective 29:55 Final Thoughts: Simplifying Growth Strategiesbles frictionless transactions and sustainable growth at scale. — Subscribe to the LeaderbookAI Podcast (formerly CPO PLAYBOOK): https://leaderbook.ai/podcast. Want to create 10x the value of your business or investments? Let’s talk: https://leaderbook.ai/contact

What do you do when the world changes faster than your workforce can adapt? Carlee Wolfe, AVP, Leader Development and Organizational Effectiveness, Hyatt Hotels, shares how she’s helping over 125,000 employees stay ahead—by building leadership capabilities that thrive in uncertainty and unlock transformation. Carlee reveals how Hyatt diagnoses leadership gaps, drives behavior change at scale, and develops future-ready leaders through a culture of continuous learning, curiosity, and experimentation. From AI adoption to people-first transformation, this episode is packed with strategy, humanity, and actionable insight. Chapters 00:00 Navigating Leadership in Uncertain Times 02:00 The Impact of Sports on Leadership Development 02:58 Understanding Leadership Roles at Hyatt 03:54 Identifying Leadership Capability Challenges 08:01 AI's Role in Leadership and Organizational Change 12:02 Overcoming Barriers to AI Adoption 14:11 The Dangers of the 'All-Knowing' Leader 16:54 The Importance of Continuous Learning in AI Transformation 18:40 Learning Out Loud: A Leadership Approach 21:10 Curiosity as a Business Competency 24:45 Diagnosing Leadership Capability Gaps 28:28 Building Leadership Capabilities at Scale 32:49 Sustaining Leadership Development 37:04 First Steps for CEOs in Leadership Development — Subscribe to the LeaderbookAI Podcast (formerly CPO PLAYBOOK): https://leaderbook.ai/podcast Want to create 10x the value of your business or investments? Let’s talk: https://leaderbook.ai/contact

What does it mean to be an AI-native employee—and why will they win? Thibault Imbert, Chief Product and Growth Officer at The Brief, joins Felicia Shakiba to break down what it truly means to work, think, and create in an AI-first world. From conversational AI to real-time prototyping with voice and visual tools, Thibault explains how AI-native employees are redefining productivity, creativity, and leadership in the modern workplace. This episode explores how AI automation, machine learning, and generative AI are transforming day-to-day work—reshaping decision making, accelerating innovation, and enabling smarter business process automation. Leaders will learn what AI-native workflows look like in practice, why speed and experimentation now drive value creation, and how empathy and human judgment remain essential even as enterprise technology advances. Chapters 00:00 Introduction and Setting the Stage 04:30 The Journey of AI Transformation 09:52 Mastering Conversational AI 15:52 Visual Creation and Concepting Ideas 23:10 Voice as a Creative Output 27:45 Prototyping and Building in Real Time 32:58 Innovative Tools for Research and Presentation This episode is a masterclass in purpose-driven leadership, capital discipline, and building companies that last. — Subscribe to the LeaderbookAI Podcast: https://leaderbook.ai/podcast We create high-performing power houses. Let’s talk: https://leaderbook.ai/contact