Outthinkers

Outthinker

The Outthinkers podcast is a growth strategy podcast hosted by Kaihan Krippendorff. Each week, Kaihan talks with forward-looking strategists and innovators that are challenging the status quo, leading the future of business, and shaping our world.Chief strategy officers and executives can learn more and join the Outthinker community at https://outthinkernetwork.com/. 

  1. #159 — Dr. Brent Ridge: The Kindness Operating System for Hiring, Culture, and Growth

    3日前

    #159 — Dr. Brent Ridge: The Kindness Operating System for Hiring, Culture, and Growth

    Dr. Brent Ridge is the co-founder of Beekman 1802, a skin health brand that began with goat milk soap made at a dining room table and scaled into a nationally recognized business with a devoted community. Brent trained in medicine (geriatrics), built his career in New York City, and even helped launch Martha Stewart’s Healthy Living division—before a recession, a rundown farm, and a herd of goats rewrote his path. He’s also the co-author of G.O.A.T. Wisdom, a new book that distills Beekman’s hard-won lessons into practical principles for entrepreneurs who want to build something that lasts. In this conversation, you’ll learn how to spot real trends before they’re named, build a brand identity customers can feel in seconds, and turn a purpose like kindness into a measurable operating system—not just marketing. In this episode we cover: Why “the true measure of authenticity is longevity” (and how brands lose trust chasing viral moments)The Beekman origin story: layoffs, a farm, goats—and turning constraints into a strategy advantageA simple but powerful strategic question: “Where does this not exist?” (and how it opened the luxury door)Trend sensing without getting trapped by algorithms: building your own daily “signal system”How defining your company as “skin health” (not “beauty”) changes everything—from product to positioningTurning kindness into culture, community, and commercial momentum (inside the company and out) 00:00 Introduction to Out Thinkers Podcast 00:30 Defining Authenticity in Business 01:23 Meet Dr. Brent Ridge: From Medicine to Entrepreneurship 02:01 The Birth of Beekman 1802 02:36 Building a Brand with Kindness 04:56 Early Life and Career of Dr. Brent Ridge 07:02 Strategic Moves: From Medicine to Martha Stewart 08:26 Launching the Martha Stewart Center for Living 18:08 The Power of Personal Branding and Sales 21:22 Navigating Trends and Building Legacy 25:01 Seeing Trends in Unlikely Places 26:30 The Birth of Beekman 1802 28:26 The Science Behind Goat Milk 30:32 Rebranding as a Skin Health Company 31:35 The Power of Brand Identity 37:57 Building a Culture of Kindness 40:43 The Kindness Ecosystem 48:22 Conclusion and Final Thoughts Additional Resources Book: G.O.A.T. Wisdom (Brent Ridge)Beekman 1802: https://beekman1802.com/Brent Ridge on LinkedIn: https://www.linkedin.com/in/brent-ridge-md-0641791/Kindness Research Foundation: https://www.kindness.orgThank you to our guest, our executive producer Zach Ness, our editor James Pearce, and the Outthinker team. If you enjoyed this episode, please follow, download, and subscribe. I’m your host, Kaihan Krippendorff—thank you for listening. Follow us at outthinker.com/podcast

    50 分鐘
  2. #158 — Jana Werner & Phil Le-Brun: How to Build an Organization That Learns and Adapts Fast

    1月20日

    #158 — Jana Werner & Phil Le-Brun: How to Build an Organization That Learns and Adapts Fast

    Jana Werner is a global executive advisor and Executive in Residence at Amazon Web Services, where she works with Fortune 500 leadership teams on organizational transformation and enterprise strategy. She holds a PhD in uncertainty dynamics in projects and has contributed to academic research and teaching at institutions including Oxford and the London School of Economics. Phil Le-Brun spent 31 years at McDonald’s, serving as International CIO and leading technology delivery across more than 120 countries. He is now an Executive in Residence at AWS, serving as an enterprise strategist and evangelist, with advanced degrees in systems thinking. Together, they are the authors of The Octopus Organization: A Guide to Thriving in a World of Continuous Transformation. Most large companies still operate like machines. Rigid hierarchies, tight controls, and permission-based decision making may deliver predictability, but they quietly kill ownership, learning, and innovation. By contrast, the most adaptive organizations operate more like living systems, distributing intelligence, empowering teams, and enabling continuous transformation. Companies like Amazon demonstrate how decentralization, clarity, and ownership can create alignment rather than chaos. This episode explores how leaders can replace command-and-control structures with environments where innovation becomes everyone’s job. In this episode we cover Why the “organization as a machine” model is breaking downThe Octopus Organization metaphor and distributed intelligence in actionHow clarity and context enable decentralized decision-makingOwnership vs permission and the pigs-and-chickens lessonWhy real innovation must be embedded across every layer of the organizationHow curiosity and intelligent failure drive continuous transformation Episode Timeline 00:00 Highlight and introduction to the Octopus Organization 02:00 Guest introductions and background 04:30 If you really know me… personal stories from Jana and Phil 07:40 Defining strategy as choice and what not to do 10:00 Tin Man vs Octopus organizations 13:30 How decentralization increases alignment 16:00 Ownership, permission, and single-threaded leadership 20:00 Amazon leadership principles and disagree-and-commit 22:30 Creating organizational clarity at scale 26:00 Focus, subtraction, and the mountaineering story 28:30 Durable needs and strategy at Amazon 30:30 Complicated vs complex systems in transformation 33:00 Curiosity, experimentation, and intelligent failure 36:00 The monkey-on-a-pedestal lesson 38:00 Centralized vs decentralized innovation 41:00 Lighting a thousand fires and continuous transformation 44:00 Why this model outperforms traditional change programs 45:30 Where to learn more and connect with the authors Additional Resources Book: The Octopus Organization Website: https://www.theoctopusorganization.com Jana Werner LinkedIn: https://www.linkedin.com/in/janawerner1/ Phil LeBrun LinkedIn: https://www.linkedin.com/in/phillebrun/ Watch now on Youtube: https://youtu.be/qcD2GmX5uUI Thank you to our guest, our executive producer Zach Ness, our editor James Pearce, and the Outthinker team. If you enjoyed this episode, please follow, download, and subscribe. I’m your host, Kaihan Krippendorff—thank you for listening. Follow us at outthinker.com/podcast

    46 分鐘
  3. #157 — Mark Thompson: What Boards Really Look for When Choosing a CEO

    1月6日

    #157 — Mark Thompson: What Boards Really Look for When Choosing a CEO

    Mark Thompson is a CEO coach and author of CEO Ready. Born and raised in Silicon Valley and now working across emerging tech hubs, Mark prepares leaders for the leap from elite operator to enterprise chief. He’s worked with CEOs ranging from Richard Branson and Evan Sharp (co-founder of Pinterest) to Dr. Jim Yong Kim (former president of the World Bank) and Dave Chang (founder of Momofuku). Most executives assume the CEO seat is the natural “next step” for the highest performer. But Mark argues you earn readiness twice: first by delivering results, and then by winning belief outside your swim lane. In other words, performance gets you shortlisted—but it doesn’t get you selected. In this episode, Mark lays out the seven stakeholders who decide your fate as a CEO candidate (the board, investors/owners, peers, employees, customers, the current CEO, and you). We talk about what each group actually wants, how to build trust across the enterprise, and why the best CEO candidates develop “conversational fluency” across functions so they can lead beyond their lane. In this episode we cover: •Why “elite performance” only gets you halfway to CEO—and what earns belief the second time •The seven stakeholders who decide CEO readiness (and how to build a plan for each one) •How to show up to the board as more than a functional expert •Turning peers into partners (before the role forces the shift) •Building fluency across functions so you can lead the whole enterprise—not just your function Episode Timeline: 00:00 Introduction to Outthinkers Podcast 01:23 Meet Mark Thompson: CEO Coach and Author 02:06 The Seven Stakeholders of CEO Success 02:42 Mark's Unique Coaching Methods 04:10 Personal Insights and Strategy Definition 06:30 The Reality of Becoming a CEO 08:58 Navigating Board Dynamics 20:57 Interacting with the Board: Key Strategies for Aspiring CEOs 21:28 Listening and Broadening Your Perspective 22:44 Understanding the Role of Strategy Officers 26:36 Navigating Peer Dynamics and Leadership Transition 33:03 Building Relationships with the CEO 35:44 Engaging with Investors and Owners 39:56 The Importance of Customer Influence 44:17 Final Thoughts and Resources for Aspiring CEOs Additional Resources: •Mark Thompson: Chief Executive Alliance — https://chieexecutivealliance.com Watch now on Youtube: https://youtu.be/wuh4Rn7erxU Thank you to our guest, our executive producer Zach Ness, our editor James Pearce, and the Outthinker team. If you enjoyed this episode, please follow, download, and subscribe. I’m your host, Kaihan Krippendorff—thank you for listening. Follow us at outthinker.com/podcast

    46 分鐘
  4. #156 — Bill George: Authentic Leadership, Purpose & Performance

    16/12/2025

    #156 — Bill George: Authentic Leadership, Purpose & Performance

    Bill George is one of the most influential leadership thinkers of our time. A former CEO of Medtronic and long-time Harvard Business School professor, he’s served on the boards of Goldman Sachs, ExxonMobil, Novartis, and the Mayo Clinic. His books including True North and True North: Emerging Leader Edition—have shaped how thousands of leaders approach purpose, values, and character. When performance pressure rises, it’s easy for leaders to drift from their values chasing quarterly metrics, external validation, and “style” over substance. Bill argues the opposite: sustainable performance springs from purpose, self-awareness, and a culture people believe in. We explore how to stay grounded as expectations, visibility, and success scale. You’ll learn how authentic leaders make the hard calls without becoming “nice at the expense of necessary,” choose metrics that drive meaning (not gaming), and build teams that keep you honest, learning, and aligned. In this episode we cover: •Authentic leadership: what it is and isn’t •Purpose-first strategy •The Medtronic metric: measuring outcomes people feel, not just inputs •Making tough people & portfolio decisions without losing your values •Building your leadership circle for honest feedback & growth •Short-term vs. long-term: preventing KPI gaming and hollow wins Episode Timeline 00:00 Introduction to Outthinkers Podcast 00:35 Bill George on Medtronic's Impact 01:40 Bill George's Leadership Journey 05:00 Defining Strategy and Purpose 10:32 Authentic Leadership Explained 12:45 Challenges and Examples of Leadership 16:04 Personal Growth and Leadership 20:53 Developing Self-Awareness as a Leader 22:15 Facing Crucibles: Overcoming Tough Times 23:47 Exercises for Self-Discovery 25:33 The Power of Small Groups 27:32 Long-Standing Support Systems 29:28 Assessing Leadership Values 33:01 Effective Metrics for Leadership 39:56 Engaging with Bill George Additional Resources •Bill George — Website: https://www.billgeorge.org •LinkedIn: https://www.linkedin.com/in/williamwgeorge/ •Book: True North: Emerging Leader Edition •Book: True North •Kaihan Krippendorff: https://www.outthinker.com Thank you to our guest, our executive producer Zach Ness, our editor James Pearce, and the Outthinker team. If you enjoyed this episode, please follow, download, and subscribe. I’m your host, Kaihan Krippendorff—thank you for listening. Follow us at outthinker.com/podcast

    42 分鐘
  5. #155 — Jon Levy: Team Intelligence, Glue Players, and the Culture That Executes Strategy

    02/12/2025

    #155 — Jon Levy: Team Intelligence, Glue Players, and the Culture That Executes Strategy

    Meet Jon Levy — behavioral scientist and author of Team Intelligence: How Brilliant Leaders Unlock Collective Genius and the NYT/WSJ bestseller You’re Invited. Jon has spent years studying human behavior and leadership mechanics, advising companies on how to build teams that actually perform—beyond leadership myths and buzzwords. We often hire “A-players,” roll out values, and assume great leadership traits will carry us. Then reality hits: strategy doesn’t execute itself—teams do. Jon explains why the smallest unit of performance is the team, why stacking stars backfires, and how culture and language shape what people actually do. If you’re trying to align leaders who don’t buy the data, this one’s for you. You’ll learn how to engineer collective intelligence—the practical habits, roles, and rituals that raise a team’s game, how to recruit and empower “glue players,” and how to make strategy felt when spreadsheets won’t persuade. In this episode we cover: Culture as operating system: the sayings, status cues, and rituals that drive behavior (Apple’s “surprise and delight,” LEGO’s “fireside”).Bursty communication: why teams should “work together, then work apart” to boost problem-solving.Glue players: high-EQ, team-first multipliers (and why too many stars tank performance).Make the implicit explicit: roles, skills, and “player cards” that speed decisions.Trust, not traits: honesty, competence, benevolence—and dealing with the dark tetrad at work.When data won’t convince: crafting a narrative that makes people feel the better future. Episode Timeline 00:00 Introduction  00:36 Coming Up... 01:47 Unpacking Team Intelligence with John Levy 02:47 Insights on Leadership and Team Dynamics 05:13 The Role of Culture in Organizations 13:49 The Impact of Language on Behavior 16:54 The Concept of Glue Players 18:14 The Key to Predicting Success in Basketball 19:02 Characteristics of Glue Players 21:25 The Importance of Team Dynamics 23:49 The Antwerp Diamond Heist: A Lesson in Teamwork 27:52 Making Implicit Knowledge Explicit 29:36 The Dark Side of Team Dynamics 31:29 Understanding Trust in Teams 34:06 The Role of Emotion in Strategy 35:02 Conclusion and Final Thoughts Additional Resources Jon Levy — Website: https://www.jonlevy.comBook: https://www.jonlevy.com/team-intelligenceLinkedIn: https://www.linkedin.com/in/jonlevytlbThank you to our guest, our executive producer Zach Ness, our editor James Pearce, and the Outthinker team. If you enjoyed this episode, please follow, download, and subscribe. I’m your host, Kaihan Krippendorff—thank you for listening. Follow us at outthinker.com/podcast

    36 分鐘
  6. #154 — Christina Farr: The Storyteller’s Advantage for Strategy and Growth

    20/11/2025

    #154 — Christina Farr: The Storyteller’s Advantage for Strategy and Growth

    Christina Farr is an investor, startup advisor, and former health-tech journalist. She’s the author of The Storyteller’s Advantage: How Powerful Narratives Make Businesses Thrive and the creator of the Second Opinion newsletter, where she decodes healthcare and technology for leaders. Most leaders try to move markets with features, roadmaps, and metrics. But the winners often move them with narrative—stories that rally investors, customers, and teams to build the future with them. Christina unpacks how great storytellers create belief that becomes momentum. You’ll learn a simple framework to make your strategy legible and compelling, how to pick the right plot for your message, and practical ways to craft origin stories, pitch decks, and CEO communications that persuade. In this episode we cover: The SOAP framework: Surprise, Openness, Authenticity, PathosSeven classic plots for business (from David vs. Goliath to Rebirth) and when to use eachCase studies: PillPack vs. incumbents; Apple’s comeback; Microsoft’s reinvention; WeWork’s cautionary taleFundraising and sales: decks that move capital and customersLeading in tense moments: speaking to charged issues without fracturing culture Episode Timeline: 00:00 – Highlight from today’s episode 01:05 – Introducing Christina + the power of narrative in business 03:05 – “If you really know me…” 04:20 – What is strategy? Story as prognostication 07:10 – Why story beats data alone in pitches, sales, and retention 10:55 – The SOAP framework (Surprise, Openness, Authenticity, Pathos) 18:40 – Engineering surprise; calibrating vulnerability 22:00 – Seven plots leaders can borrow (with modern brand examples) 28:45 – Case study: PillPack’s David vs. Goliath playbook 32:40 – Rebirths and tragedies: Apple, Microsoft, WeWork 36:10 – Origin stories that travel (and ones that don’t) 38:10 – CEO comms on divisive topics, without breaking culture 39:20 – Where to learn more from Christina Additional Resources: Book: The Storyteller’s Advantage — Christina Farr (Basic Venture) -https://basic-venture.com/titles/christina-farr/the-storytellers-advantage/9781541704299/Newsletter: Second Opinion - https://secondopinion.media/Christina Farr on LinkedIn - https://www.linkedin.com/in/christinafarr/Thank you to our guest, our executive producer Zach Ness, our editor James Pearce, and the Outthinker team. If you enjoyed this episode, please follow, download, and subscribe. I’m your host, Kaihan Krippendorff—thank you for listening. Follow us at outthinker.com/podcast

    39 分鐘
  7. #152 — Mark Crowley: Lead From The Heart, Build Belonging, And Boost Performance

    04/11/2025

    #152 — Mark Crowley: Lead From The Heart, Build Belonging, And Boost Performance

    Mark Crowley is a longtime financial services leader who led consistently top-performing teams over a 25-year career. He’s the author of Lead From the Heart and the newly released The Power of Employee Well-being, a frequent contributor to Fast Company, and host of the Lead From the Heart podcast. In 2013, Mark was the first to publicize Gallup’s finding that only 30% of U.S. employees were engaged—helping ignite a decade-long debate about what truly drives performance. In this conversation, we explore why feelings and emotions—not dashboards—drive behavior, how the heart–brain connection shapes decisions at work, and why belonging outperforms “boss quality” as a predictor of retention. Mark connects lived leadership to research—from Oxford’s wellbeing–productivity link to HeartMath’s work on coherence—and shows how caring (not coddling) creates the conditions for sustained results. Whether you lead a business unit, a project team, or a transformation office, this episode will reframe how you raise performance by raising wellbeing—with specific, near-term moves any leader can make this week. In this episode we cover: Why traditional engagement efforts flatline—and why wellbeing is the more powerful lever for performanceThe Oxford evidence: how self-reported wellbeing maps directly to productivity in real workBelonging > boss quality as a driver of retention—and how leaders actually build itCaring vs. being nice: creating psychological and emotional safety without lowering the barA practical definition of strategy: know where you’re going, plan with rigor, pivot fast when reality disagrees Episode Timeline: 00:00 – Introduction 01:10 – Guest introduction and the case for feelings over dashboards 03:05 – “If you really know me…” and how Mark learned to lead from the heart 06:45 – Managing differently: proof from 25 years of top-performing teams 09:30 – Mark’s definition of strategy: plan hard, pivot faster 12:20 – Why wellbeing (not satisfaction) sets the stage for peak performance 15:10 – What wellbeing actually is—and why managers determine most of it 18:05 – Up to 95% of behavior is emotion-driven: implications for leaders 20:30 – Engagement stalled; the Oxford call-center study on wellbeing → productivity 25:40 – Caring vs. nice; HeartMath and the science of coherence 31:00 – Selecting and developing leaders who elevate others (not just individual stars) 36:10 – Belonging as the #1 driver of retention—and how to create it 39:20 – Where to start: know yourself, clarify values, design team-first systems 42:15 – Reward the team first (then individuals) to eliminate zero-sum competition 44:10 – How to keep learning from Mark + close Additional Resources: Website: https://markccrowley.comLinkedIn: https://www.linkedin.com/in/markccrowleyBooks: Lead From the Heart; The Power of Employee WellbeingPodcast: Lead From the Heart Thank you to our guest, our executive producer Zach Ness, our editor James Pearce, and the Outthinker team. If you enjoyed this episode, please follow, download, and subscribe. I’m your host, Kaihan Krippendorff—thank you for listening. Follow us at outthinker.com/podcast

    45 分鐘

關於

The Outthinkers podcast is a growth strategy podcast hosted by Kaihan Krippendorff. Each week, Kaihan talks with forward-looking strategists and innovators that are challenging the status quo, leading the future of business, and shaping our world.Chief strategy officers and executives can learn more and join the Outthinker community at https://outthinkernetwork.com/. 

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