The Reboot Chronicles with Dean DeBiase

Dean DeBiase
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The Reboot Chronicles Show with Dean DeBiase, highlights the world’s top leaders & CEO’s through engaging peer-to-peer conversations that audiences love, available wherever you get podcasts, with thousands of listeners, watchers, readers, and fans. - - About Host: Named “Growth Guru” by Inc., Dean DeBiase is a WSJ best-selling author, Forbes Contributor, speaker, Kellogg/Northwestern faculty member—and award-winning serial CEO who has led dozens of companies across diverse sectors, creating hundreds of products, thousands of jobs, and billions of dollars in revenue, capital, and value.

  1. 28 AGO

    Recognizing Life’s Serendipitous Moments To Pivot With Purpose, David Butler - Co-CEO Dimensional

    David Butler’s life is a classic reboot story, from the courts of NBA Basketball to Wall Street Titan and co-CEO of Dimensional Fund Advisors. A powerhouse in the boardroom and on the court, David’s career has been anything but conventional. A Rhodes Scholar candidate and Pac-12 Basketball Hall of Honor inductee, he was an All-American at UC Berkeley and drafted to the Boston Celtics. When his NBA career was sidelined by a strike and injury—David was faced with a serendipitous moment in his life that many would have missed—and pivoted with purpose, launching a remarkable Reboot journey shaped by discipline and a vision. A powerful force on the court, David has Rebooted Dimensional into a $850B powerhouse to become a leading global financial services group. Long before the me-too AI train, instead of chasing hot stock tips, they redefined the financial advice model with a systematic, research-based investment approaches that have outperformed their competitors. Listen in as we unpack David’s remarkable personal journey and how a former pro baller became a Wall Street Trailblazer.

    33 min

  2. 19 AGO

    How To Reshuffle And Reboot YouOrganization Like A Pro, Sangeet Choudary – CEO Platformation

    When a CEO steps into a company with the mindset of initiating a full-scale reboot, it’s not just a refresh—it’s a renaissance. My best reboots have been built on three foundational pillars: People - Platform - Passion. Platform (my favorite) often becomes the keystone of growth, especially when you reimagine it not just as infrastructure, but as a conduit—an engine of connection. Think of Amazon as the digital bridge between consumers and merchants, or Facebook as the social circuitry linking lives across the globe. Platforms, in their purest form, are the connective tissue of modern enterprise—rebooting how ideas, services, business models, and relationships flow between entities. And when done right, they don’t just support the business—they redefine it. Bestselling author, Sangeet Choudary - CEO of Platformation Labs, joins us to unpack all of this. A platform guru, he is an advisor to Fortune 50 CEOs, a Scholar at Dartmouth, a Fellow at UC Berkley, and holds key advisory roles in the Indian Government, World Economic Forum, Standard Bank, ING Bank and GPA—the largest food retailer in Latin America. Listen in as we explore his latest book, Reshuffle: Who Wins When AI Restacks, and explore what I write about in Forbes: how AI is transforming knowledge economies, shifting expertise to AI tools—fundamentally altering our workflows and organization power dynamics.

    34 min

  3. 13 AGO

    How To Cut Through All The AI Hype By Avoiding Easy Money Traps, Raj Mamodia - CEO Brillio

    Rewind to 2014, when the tech world was sort of dancing around the promise of the “digital future.”  The term “digital transformation” was just beginning to gain traction, and “cloud computing” had become the darling of boardroom conversations, though many enterprises were still hesitant to fully embrace it. At the time, if you were one of the rare leaders who could see past the noise and around corners, and understood that data, cloud, and AI would become the backbone of enterprise reinvention, you would be on track to be one of the fastest-growing tech service providers in the ecosystem.   That, at least, is the case for our next guest on the Reboot Chronicles Show, Raj Mamodia. Raj is the Founder and CEO of Brillio, a tech service provider that partners with Global 1000 corporations to reboot themselves for growth and success in our crazy digital age. While others chased hype cycles and easy exits, Raj built a company grounded in execution, innovation, and long-term value creation. Today, Brillio is on a trajectory toward becoming a multi-billion-dollar market leader in digital services. Listen in as Raj unpacks how he navigated the early fog of digital transformation, resisted the lure of short-term trends, and built a company that’s helping the world’s largest enterprises thrive in a tech-driven future.

    34 min

  4. 6 AGO

    What Really Matters In Our Short Time On Earth, Harry Kraemer – ex-CEO of Baxter & Kellogg Professor

    Leadership isn’t just about C-suite executives running big businesses. It’s about leading with values at every stage of your life, using tools to improve yourself, your work, your relationships—and rebooting yourself with balance to lead a better life.On this dynamic episode of The Reboot Chronicles Show, the world’s leading expert joins us to unpack all of this and much more. Harry Kraemer is the ex-CEO of Baxter, a best-selling author, and a Clinical Professor of Leadership at Northwestern University’s Kellogg School of Management. A friend and colleague, Harry has been a remarkable professor at Kellogg for over 20 years, has authored four impactful leadership-based bestsellers—and Chairman and CEO of Baxter—which he rebooted into a $12B company. Listen in for amazing insights and lessons that Harry has built over his decades as a top global CEO, professor, and author—with straight talk about what leadership is all about, why we should seek to understand before you are understood—and how to first relate and influence before you lead.

    33 min

  5. 30 JUL

    Unleashing 400M Digital Workers with AI-Powered Automation, Mihir Shukla - CEO Automation Anywhere

    Most every C-suite leader wants AI to help their people perform tedious tasks better. We still live in a world where we are stuck doing too many time-consuming, lower impact tasks - like organizing spreadsheets, manually processing forms and data entry, or swiveling information from app to app across your company’s hundreds of applications. Ugh. Helping the corporate world get closer to a reality where humans are not mired in low-efficiency tasks is Mihir Shukla, Co-Founder and CEO of Automation Anywhere, an Agentic Process Automation (APA) pioneer delivering agentic solutions that leverage AI agents to get work done faster, better and more reliably. A Silicon Valley veteran, Mihir is a multi-decade pioneer of automation and has a vision to fully deliver an autonomous enterprise, where 80% of work is done through automation or AI-assistance. But what happens to our jobs? For Mihir, it’s important to note that an autonomous enterprise doesn't eliminate human work - it redefines it. Employees transition from managing repetitive tasks to overseeing AI-driven systems and teams, with the ability to make strategic decisions, drive new business models and focus on delivering strategic impact. Sound good? With incredible market momentum, top-shelf partners and customers, top marks from analysts and a vision to fuel the future of work by unleashing human potential, they are at the forefront of empowering 400 million automations and AI agent ‘digital workers’ to shape the enterprise of the future – today.

    33 min

  6. 23 JUL

    Unwrapping A Retail Revolution One Candy Bar At A Time, Dylan Lauren - Dylan’s Candy Bar

    When it comes down to brands that put 110% into customer experiences, few have managed to create something as sweet as Dylan’s Candy Bar. Since opening around the turn of this century, Dylan’s has grown into the world’s largest confectionery emporium and a multi-channel lifestyle brand with more than 7,000 SKUs across categories from gourmet sweets and nostalgic treats to fashion, accessories, and home decor. Through a blend of nostalgia, style, and an immersive experience whenever you interact with their product, it is hard not to feel like a kid again. Often called the “Candy Queen”, Dylan Lauren is an entrepreneur, designer, daughter of fashion royalty, and CEO of Dylan’s Candy. The visionary who reimagined how the world experiences candy, Dylan has built one of the most iconic brands in retail-tainment, and become a cultural force – merging sweet nostalgia with cutting-edge design and philanthropic purpose.  Listen in as she unwraps where her inspiration comes from, how she unleashed her inner child to turn classic candy stores into a playground for all ages, why her childhood dreams and an eye for color helped her create a brand that tastes as sweet as it did decades ago—and what her next reboot looks like.

    32 min

  7. 16 JUL

    Building A Global Brand From Crates And Barrels, Gordon Segal - Founder Crate & Barrel

    Retail is a brutal industry where even the massive companies, that seem impossible to topple, can crumble. Crate and Barrel has long been a household name in American retail, which shaped how generations of consumers furnish their homes. What started as a small Chicago storefront in the 1960s has grown into a $2B global brand with over 100 locations, a powerful online presence, and sister brands like CB2 and Crate & Kids that continue to redefine the home shopping experience.In this episode of The Reboot Chronicles, we sit down with Gordon Segal, the co-founder of Crate and Barrel. As the Chairman and CEO, Gordon grew Crate & Barrel into a global home furnishings powerhouse, pioneering the accessible modern design movement that rebooted American retail through experiential store layouts, minimalist merchandising, and international sourcing. A pioneer in retail, Gordon helped create an accessible, design-forward brand long before “lifestyle retail” became a thing. Follow along as Gordon reflects on Crate and Barrel’s humble beginnings, keys to scaling a values-driven business, tough leadership transitions and reboots, and how staying true to culture remains a competitive advantage—even in an era of Amazon and Wayfair.

    32 min

  8. 7 JUL

    FICO Scores Often Mean No. Meet The Scientists Making It Say Yes, Sanjiv Das – President Pagaya

    When it comes to the financial industry the word “NO” seems like their favorite response—many banks have VP’s of No! To a promising borrower who gets denied due to a hard-set credit model, or a working parent who has a steady income but a short credit history, banks are likely to say no to both of their loan requests. One of the ways to resolve this is rebooting how FICO scores work—but good luck getting the big dog banks to learn a new system. Sanjiv Das, the co-founder and president of Pagaya, is rebooting all of it. They are not changing how FICO scores work, but the loan system as a whole. Pagaya is an AI-powered underwriting platform connecting lending partners, like VISA, Master Card, US Bank, Ally, and SoFI with a network of over 130 institutional investors. Founded in Israel and taken public on the NASDAQ, Pagaya has optimized AI to underwrite “second-look” loans—the kind traditional lenders might decline—by partnering with financial institutions that want to expand credit access without all of risk.The billion-dollar company has experienced massive growth, evaluated over $2.6T in loan applications and generated $32B in new credit across millions of consumers through point-of-sale, personal, and auto loans. That’s a lot of data! With hundreds of data scientists, they continue to lead the industry, expanding their platform capabilities, that go beyond the old traditional FICA score systems—and they just launched a new $1 billion POS lending program.Sanjiv explains it all, from their underwriting engine designed to see people not just profiles to the immense power AI has on this industry and why this venture was worth leaving retirement for.

    32 min
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The Reboot Chronicles Show with Dean DeBiase, highlights the world’s top leaders & CEO’s through engaging peer-to-peer conversations that audiences love, available wherever you get podcasts, with thousands of listeners, watchers, readers, and fans. - - About Host: Named “Growth Guru” by Inc., Dean DeBiase is a WSJ best-selling author, Forbes Contributor, speaker, Kellogg/Northwestern faculty member—and award-winning serial CEO who has led dozens of companies across diverse sectors, creating hundreds of products, thousands of jobs, and billions of dollars in revenue, capital, and value.

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