The Reboot Chronicles with Dean DeBiase

The Reboot Chronicles with Dean DeBiase

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.

Episodes

October 29, 2025 35 mins

Artificial Intelligence and the potential productivity benefits continue to be an area of focus across industries, yet AI’s influence now extends into our culture. From deepfakes and cloned voices to AI-generated art and virtual influencers, a new wave of synthetic content is transforming media and testing our ability to trust what we see and hear.

In this episode of The Reboot Chronicles,  Henry Ajder,founder of Latent Space Adviso...

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Launching a startup is daunting—especially when you're navigating the journey without guidance or mentorship. Even well-funded ventures struggle, and those that beat the odds are so rare they're dubbed "Unicorns." Our next guest on the Reboot Chronicles Show has helped countless start-ups become successful and redefined what we here at the Reboot Chronicles believe to be key components in rebooting organizations. 

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Most businesses are rapidly deploying AI to be more competitive, but some are struggling to adapt, or worse, think Microsoft Co-Pilot is enough adaptation. Sectors like consulting, accounting, and law firms, are in big trouble and many are facing an Opportunity Crisis. Our next guest is reaching that point in their evolution, but instead of being disrupted, they are choosing to reboot themselves as the disruptors who can create and...

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From Olympic runways to boardroom breakthroughs, Simon Arkel knows how to raise the bar—and clear it. On this episode of The Reboot Chronicles, we’re joined by this two-time Olympian and five-time NCAA All-American whose journey is a masterclass in reinvention. 

 Simon’s pole vaulting career was built on grit, resilience, and relentless pursuit—qualities that now define his impact in the healthcare industry. Simon has served as CEO ...

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You know the song MMMBop. You probably danced to it. But do you know the man behind it? Taylor Hanson went from topping charts in 27 countries to brewing up a business empire.  In an industry that often trades authenticity for applause, Taylor and his two brothers chose ownership over dependency—when he was just nine years old! Celebrity guests often bring star power—but few bring the depth of reinvention and a journey that ...

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Long before brand-building became a buzzword and athletes were expected to be media-savvy moguls, our guest on this episode of the Reboot Chronicles Show, Jan Stephenson, was already rewriting the rules.

Born under the sun-drenched skies of Sydney, Australia, she stepped onto the LPGA Tour in 1974 with a swing as fearless as her spirit—and a vision that would forever change the face of women’s golf. In a sport steeped in tradition,...

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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 a...

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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 consu...

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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, c...

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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 a...

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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 l...

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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 nos...

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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 c...

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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 ...

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Being the biggest leader in your industry sector doesn’t guarantee the future anymore. These days it can be quite the opposite, as we continue to witness big-dog leaders being dethroned by the next generation of agile tech-enabled competitors.On this episode of The Reboot Chronicles Show we have a sit down with Wayne Levings, a CEO, Chief Client Officer, and Executive Committee Member at Kantar, to learn from one of the biggest reb...

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These days, it’s not a matter of “if”, but when you or your organization will get hit with cybercrime. AI compounds the problem, arming lone attackers and organized gangs with cheap and easy tools to commit their misdeeds. It’s one thing when you know what might be coming, and quite another to defend against new exploits, the “unknown unknowns” that can tie your team up in knots and cause massive damage.This episode connects two to...

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It’s easy to get lost in the AI gold rush exploding around the globe. On this episode of The Reboot Chronicles Show, Appian CEO Matt Calkins explains why AI’s greatest value isn’t about replacing humans, but about helping organizations work faster or smarter. Now it is time for a moment of truth about the basic value of AI.

A great American entrepreneurial growth story, Matt has grown Appian from a scrappy basement startup to the mo...

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When it comes to fast food, people mostly focus on fast. With improving efficiency and a new sales-driven promotion every month, the faster a company can get food to customers, the better, right? Maybe not. Chick-fil-A developed a smarter idea—prioritizing People over Profits with Purpose and Faith.

 

On this episode of The Reboot Chronicles, one of Chick-fil-A’s founding C-Suite leaders, Steve Robinson, reveals untold stories on how...

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Most everyone remembers the tale of David and Goliath, one of the greatest underdog stories. We have seen the story repeat itself in business, across sectors from food and car companies to consumer products and tech. But what about AI? The AI computer chip wars are heating up—on fire actually—as companies attempt to topple the Goliath that Nvidia has become. Our David for this episode is Cerebras Systems, one of the rapidly-growing...

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The art of business growth often requires being in the right market, at the right time, with the right resources to make an impact—and mastering the discipline of what you are going to build, buy, and borrow. Most companies deploy a mixture of these three methods, but our guest on this episode has mastered the buy side, with a well-funded market-making acquisition machine. Rich Eknoian, CEO of World Insurance Associates, has built ...

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