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Outthinkers

Outthinkers

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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/.

© 2025 Outthinker
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Épisodes
  • #150 — Scott Anthony: Disruptions and the Patterns That Shape Innovation
    Oct 14 2025

    Today we’re welcoming back our first-ever guest on the Outthinker Podcast, Scott Anthony—Senior Lecturer at Dartmouth’s Tuck School of Business and one of the world’s leading voices on innovation and transformation. Formerly a senior partner at Innosight, the consultancy founded by Clayton Christensen, Scott has spent decades helping global organizations navigate disruption, build strategic resilience, and create new engines of growth. He’s also the author of eight acclaimed books, including The First Mile, Dual Transformation, and his newest work, Epic Disruptions: 11 Innovations That Shaped Our Modern World.

    In this discussion, we uncover how disruption has driven human progress for centuries—long before the dawn of Silicon Valley. From the cannon fire that toppled ancient empires to the printing press that democratized knowledge, Scott shows that the forces behind disruption are anything but new. Through stories spanning from gunpowder to generative AI, he reveals how these enduring patterns continue to reshape industries, technologies, and societies today.

    Listeners will walk away with a richer understanding of how to spot and harness disruption rather than fear it. Scott explains how leaders can use history as a practical playbook—learning to make bold, informed decisions in fast‑changing environments. Whether you’re scaling a business or steering an enterprise through transformation, this is a conversation about seeing beyond the moment to shape what comes next.

    In this episode we cover:

    • What Clayton Christensen really meant by “disruptive innovation”
    • Why the term is so often misused—and how to tell sustaining vs disruptive innovation apart
    • The “ghosts” that haunt incumbents: past trauma, rigid habits, and identity fears that block change
    • What leaders can learn from the printing press, steel mini mills, and the iPhone
    • How to use history as a lens for seeing disruption before it strikes

    Episode Timeline:

    00:00 — Highlight from today’s episode
    01:10 — Introducing Scott Anthony and today’s topic
    04:00 — From consulting to academia: finding no “safe spaces” in the era of AI
    09:00 — Defining strategy: “a set of choices to achieve a designed aim”
    10:00 — Setting the record straight on Clayton Christensen’s theory
    16:30 — Bethlehem Steel, emotional ghosts, and leadership through disruption
    21:00 — From gunpowder to AI: how patterns keep repeating
    25:00 — The printing press and the unintended consequences of innovation
    30:00 — The hero’s journey of innovation—from Julia Child to Steve Jobs
    37:00 — Spotting modern disruptors: AI, robotics, and additive manufacturing
    41:00 — Where to learn more from Scott Anthony

    Additional Resources:

    Book Website: https://www.epicdisruptions.com
    Scott Anthony’s LinkedIn: https://www.linkedin.com/in/scottdanthony/

    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 outthinkernetworks.com/podcast

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    41 min
  • #149 — Adam Brotman: Building the Mindset of an AI‑First CEO
    Oct 7 2025

    Adam Brotman is the former Chief Digital Officer of Starbucks and Co-CEO of J.Crew, and co‑author of the e‑book AI‑First: The Playbook for a Future‑Proof Business and Brand. At Starbucks, he helped create one of the most admired digital customer experiences in the world and was named Chief Digital Officer of the Year. Today, as co‑founder of Forum3, Adam helps executives navigate the next era of business transformation—one where AI is no longer optional, but foundational.

    Over the past two years, Adam has interviewed some of the most influential voices shaping artificial intelligence—Bill Gates, Sam Altman, Reid Hoffman, and Ethan Mollick, among others. Through those conversations, he’s uncovered what separates companies that simply experiment with AI from those that truly transform.

    In this episode, we unpack what it really means to become an AI‑first leader—someone who doesn’t need to code or build models, but who develops the instinct and conviction to guide their teams into this new frontier.

    In this episode we cover:

    • What it means to be an AI‑first CEO and why it starts with an authentic “aha moment.”
    • Bill Gates’ perspective on AI as a tool for qualitative uplift, not just productivity.
    • The idea of the “middle era” of AI—why it feels messy, and how visionary leaders navigate it.
    • Lessons from Starbucks’ shift from digital‑first to AI‑first thinking.
    • Why the real ROI of AI lies in better decisions, faster, across every function.

    Episode Timeline:
    00:00 — Highlight from today’s episode
    01:15 — Introducing Adam + today’s topic
    02:30 — The AI‑first mindset: where transformation really begins
    06:00 — Bill Gates on why AI is bigger than any past tech shift
    10:00 — Quantitative vs. qualitative productivity
    12:00 — Inside “the middle era” of AI
    16:00 — Defining the AI‑first company and leader
    25:00 — Beyond ROI: reframing AI’s value
    28:00 — Research insights: why AI improves decision quality
    31:00 — From skepticism to the CEO’s “aha” moment
    33:00 — What’s next after the middle era
    38:00 — Closing reflections + how to keep learning from Adam

    Additional Resources:
    LinkedIn: https://www.linkedin.com/in/adambrotman
    Book & Company: https://www.forum3.com/ai-first-book

    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 outthinkernetworks.com/podcast

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    40 min
  • #148—Julia Austin: How Startups and Big Companies Turn Sparks Into Scale
    Sep 16 2025

    Our guest today is Julia Austin—former senior leader at Akamai, VMware, and DigitalOcean, with decades of experience helping organizations make the leap from startup to scale. She’s also studied and guided countless founders as a professor at Harvard Business School. Julia now distills those lessons in her new book, After the Idea: What It Really Takes to Create and Scale a Startup.

    In this conversation you’ll discover what separates ventures that thrive from those that stall. Every company begins with a spark, but too often innovators fall in love with ideas, overbuild too soon, or underestimate the hard realities of scaling and culture. Julia draws from experience spanning tech giants and countless startups to reveal how leaders can move from inspiration to momentum—and sustain innovation even as complexity grows.

    You’ll learn practical frameworks and stories for transforming early insights into long-term impact. Whether you’re a founder, strategist, or innovator inside an established business, this conversation offers tools for approaching discovery, scaling, and culture design.

    In this episode we cover:

    • Four types of scrappy experiments every innovator should run: ethnographic, “be the bot,” Wizard of Oz, and low fidelity prototypes
    • How to know if there’s really a there there in your market
    • Balancing beachheads and total addressable markets while keeping unit economics in check
    • Building competitive advantages through team, domain expertise, and partnerships
    • How to design org structures and cultures that reward experimentation and embrace productive failure

    Episode Timeline:

    00:00 — Highlight from today’s episode
    01:18 — Introducing Julia Austin and today’s topic
    04:45 — “If you really know me…” Julia’s art background
    06:30 — Julia’s definition of strategy as a “living, breathing map”
    09:15 — Lessons from Akamai and VMware on scaling from startup to global enterprise
    14:50 — The importance of discovery: why slowing down helps you go faster
    21:05 — Four types of experiments: ethnographic, be the bot, Wizard of Oz, low fidelity
    33:40 — Testing markets: TAM, beachheads, and unit economics
    42:20 — Building competitive advantage beyond the idea
    49:15 — Designing cultures that keep innovation alive at scale
    55:45 — Why celebrating failure fuels long-term breakthroughs
    01:02:10 — Julia’s book After the Idea and how to connect with her

    Additional Resources:

    • Book Website: https://www.aftertheideabook.com/
    • Julia Austin's LinkedIn: https://www.linkedin.com/in/juliaaustin




    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 outthinkernetworks.com/podcast

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    32 min
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