The Reboot Chronicles with Dean DeBiase

Hosted by Dean DeBiase

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228

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Jun 2026

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About the show

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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60 recent

June 10, 202634 min

From Pilots to Production: Brian Bryson, Principal Analyst at MIT Technology Review

The conversation around artificial intelligence has shifted. It is no longer a question of what AI can do, it is a question of where it belongs inside an organization and how to integrate it into the fundamental operating system of a business. Brian Bryson, principal technology analyst at MIT Technology Review, has been tracking that shift closely, and his conclusion is clear: AI is no longer a technology problem. It is a change management problem. As one of the most trusted voices in technology research and analysis, Bryson helps senior executives, policymakers, and business leaders cut through the hype, understand what is real, and prepare for what is coming next. MIT Technology Review reaches millions of influential decision makers across technology and business, and Bryson sits at the center of that conversation, connecting technical breakthroughs in AI, quantum, and energy to the real-world business implications that matter most to the leaders navigating them.On this episode of The Reboot Chronicles Podcast, we sit down with Brian Bryson, principal analyst at MIT Technology Review, to unpack how AI adoption is evolving from experimentation to enterprise integration, what the most forward-thinking organizations are doing differently, why the convergence of AI, quantum, and energy represents the next major investment thesis, and how MIT is repositioning itself around the most consequential technology forces of our time. Bryson also shares his personal reboot story that taught him why slower is sometimes faster, and why rebuilding from the foundation up is the only way to build something that lasts.

June 3, 202636 min

Paratrooper to Portfolio Pro: Eric Schimpf, President of Merrill Wealth Management

Eric Schimpf left the Army on a Friday and walked into Merrill Lynch as a trainee on the following Monday morning. With no transition period, no legacy track, no shortcuts, just two suits, three ties, and a rusted-out Jeep he was encouraged to park several blocks away from the office. Thirty-two years later, Schimpf is president of Merrill Wealth Management, overseeing 25,000 associates, 1.7 million clients, and one of the strongest years in the firm's history, a record $20.7 billion in revenue across approximately $4T in assets. The path from West Point graduate and airborne ranger to the top of one of the world's most recognized wealth management franchises was built on the same principles Schimpf learned in uniform: discipline, clarity of mission, a willingness to do the work, and an unrelenting focus on the people in front of you.On this episode of The Reboot Chronicles Podcast, we sit down with Eric Schimpf, President of Merrill Wealth Management, to unpack the leadership philosophy behind one of the most significant turnarounds in wealth management. We discuss what the military taught him about leading at scale, how Merrill is thinking about AI as a productivity multiplier rather than a replacement for human advice, and what aspiring leaders need to do to position themselves for the next decade. Schimpf also shares his perspective on hiring veterans, why he believes the country will face a shortage of financial advisors, and how the firm's approach to training is designed to prepare for the future.

May 20, 202641 min

Building Command Centers And Motes To Harness AI’s Space Time Continuum, Daniel Newman - CEO Futurum

The technology research and advisory industry is being rebuilt from the ground up, and Daniel Newman is leading that charge from the inside. As CEO of Futurum, Newman has spent the last several years transforming what was once a traditional media and analysis firm into a real-time AI-powered intelligence platform serving technology buyers, enterprise investors, and the world's largest technology providers. As a seven-time bestselling author, frequent voice on CNBC, Bloomberg, and the Wall Street Journal, and a recognized name in enterprise technology analysis, Newman has built Futurum through disciplined bootstrapping, strategic acquisitions, and a willingness to reinvent the business model before the market forced his hand. With a major acquisition now in progress that will add hundreds of financial services firms and approximately $2Trillion in enterprise spend to the platform, Futurum is entering a new phase, one that Newman believes will redefine how decisions are made and how investors capitalize on the opportunity in the enterprise tech market. On this episode of The Reboot Chronicles Podcast, we sit down with Daniel Newman, CEO of Futurum, to unpack how he built and scaled one of the most influential independent technology research platforms in the world. We discuss why he saw the generative AI disruption coming before most of his peers and how Futurum is using AI to reinvent its own business model in real time. We discuss what enterprise leaders are still getting wrong about AI adoption and close with a personal reboot story that shaped Daniel’s approach to risk, resilience, and building through uncertainty.

May 13, 202646 min

Behind The Vault: America's Most Powerful Financial Dynasty Secrets Revealed, Justin Baer - The WSJ

Few journalists have spent more time inside the power centers of American finance than Justin Baer. As a senior editor at the Wall Street Journal, Baer has covered the biggest banks, brokers, and asset managers in the world, from the post-2008 regulatory battles to the pandemic economic shocks that rewrote the rules of investing almost overnight. His reporting has taken him inside Goldman Sachs, Morgan Stanley, Pimco, and dozens of other institutions that shape how capital moves through the global economy. Now he has turned that same lens onto one of the most influential and least understood firms in American finance, Fidelity Investments, in his new book The House of Fidelity, a rare behind-the-walls look at a company that has managed roughly $18 trillion across 83 million customer accounts while revealing almost nothing about how it actually operates.On this episode of The Reboot Chronicles Podcast, we sit down with Justin to unpack the hidden history of Fidelity, what the Johnson family dynasty tells us about the future of American investing, and what journalists and investors alike are getting wrong about artificial intelligence. Justin breaks down how Fidelity survived an existential crisis in the 1970s and came out the other side as the dominant force in American retirement savings, why being a private company turned out to be one of the greatest strategic advantages in financial history, how the democratization of investing really began and who deserves the credit, and what the current AI investment boom has in common with the fiber optic bubble of the late 1990s.

May 6, 202632 min

How Enterprise Tech Companies Are Fighting For Survival In The AI SaaSpocalypse, Mari Cross - Infor

Few executives bring the range of perspective that Mari Cross carries into the C-suite. As Chief Customer Officer at Infor, a roughly $3.5 billion enterprise software company with 17,000 employees, 2,000 partners, and 60,000 clients across 175 countries, Cross leads customer success, value engineering, and transformation teams spanning some of the most complex industries in the world. From discrete and process manufacturing to healthcare and public sector; her path to that seat ran through classical dance in Russia, sStanford business school, and senior roles at Adobe, Nielsen, and Gartner, long before customer experience became a board-level conversation. Today she is applying her diverse experience to one of the most significant transformations in enterprise technology, helping a company that spent years as an acquisition machine reinvent itself as a cloud-first, AI-powered, micro-vertical platform. Info was built around a simple but radical idea: enterprise software should drive outcomes, not just features.On this episode of The Reboot Chronicles Podcast, we sit down with Mari to unpack what it actually takes to modernize a legacy ERP company. Why Infor's micro-vertical strategy is outmaneuvering larger competitors, and what most enterprises get dangerously wrong about AI. Mari breaks down how an open architecture philosophy is changing what is possible for manufacturers and distributors. The last mile of AI adoption is harder than anyone admits. She shares her perspective on what Koch Industries brings to the table as a long-term investor, and what systems thinking, whether in music, mathematics, or enterprise software, has to do with being a great leader.

April 28, 202648 min

Trump’s Ten Commandments And What Really Drives High Impact CEOs, Jeffrey Sonnenfeld - Yale

Few people have spent more time inside the minds of the world's most powerful leaders than Jeffrey Sonnenfeld. As Senior Associate Dean and Lester Crown Professor at Yale School of Management and Founder of the Chief Executive Leadership Institute, Sonnenfeld has advised five US presidents and thousands of chief executives navigating crisis, succession, geopolitical shocks, and the ever-shifting expectations of corporate governance. A trusted voice across CBS, NBC, ABC, CNN, CNBC, Fox, the Wall Street Journal, the New York Times, the Financial Times, and Bloomberg, he has spent a lifetime decoding the human side of leadership through eight books, hundreds of articles, and decades of governance research. His latest book unpacks the strategic lessons from President Trump's leadership toolbox, arriving at a moment when executives everywhere are trying to understand a style of leadership unlike anything corporate America has encountered before.On this episode of The Reboot Chronicles Podcast, we sit down with Jeffrey to unpack how the world's top CEOs are approaching artificial intelligence, what Fortune 500 companies should actually do about China, and what leaders can and cannot learn from Donald Trump's playbook. Jeffrey breaks down how he built the Chief Executive Leadership Institute from a simple idea into the premier peer learning environment for global CEOs, why resilience from failure is the most important leadership lesson he teaches, how AI is reshaping both the C-suite and the classroom, and what civic duty has to do with corporate strategy.

April 21, 202640 min

CNBC’s Morgan Brennan On Re-Industrializing America, SpaceX IPO, And Next Generation Of Investing

The future of journalism is being reimagined real time, with rising stars like Morgan Brennan leading the way. As anchor of CNBC's Morning Call and host of Manifest Space podcast, Brennan brings a rare combination of editorial instinct, policy fluency, and operator-level curiosity to one of the most consequential shifts in modern media history. Having covered defense and emerging space economies for CNBC and produced shows with world leaders and elite entrepreneurs, she has operated at the intersection of markets, technology, and national security for more than a decade. Today, she is applying that experience to CNBC's mission to build the next generation of business news, one where trusted information moves at the speed of a retweet.On this episode of The Reboot Chronicles Podcast, we sit down with Morgan Brennan to unpack the Reindustrialization of America, the rise of defense and space as ground zero for industrial policy, and the future of morning news. She breaks down how CNBC is evolving from a linear television network into a multi-platform ecosystem. Why the developing world of retail investors is leading the next wave of financial media adoption and how defense spending and space commercialization are reshaping the American industrial base. Plus, we explore innovator's dilemma for traditional media companies slow to respond to the next generation of content consumption.

April 14, 202636 min

How To Reboot Old School Banking - Heath Tarbert, FMR Asst. Treasury Secretary & Circle President

The global financial system is being rebuilt from the ground up, and Heath Tarbert is helping lead that effort As President of Circle, the company behind USDC, the world's second largest regulated stablecoin, Tarbert brings a rare combination of regulatory authority, legal prowess, and market experience to one of the most consequential shifts in modern finance. Having served as Chairman of the CFTC, Assistant Secretary of the US Treasury, and Chief Legal Officer at Citadel Securities, he has operated at the center of global finance for decades, representing the United States at the G7, G20, the World Bank, and the Financial Stability Board. Today, he is applying that experience to Circle's mission of building the infrastructure for a global internet financial system, one where dollars move as easily and instantly as an email.On this episode of The Reboot Chronicles Podcast, we sit down with Heath to unpack the rise of stablecoins, the passage of the Genius Act, and what it means for banks, businesses, and consumers around the world. Heath breaks down how Circle has evolved from a stablecoin issuer into a full-stack internet financial platform, why the developing world is leading adoption, how ARC, Circle's new purpose-built blockchain, could become the economic operating system of the next generation of finance, and what the innovator's dilemma means for the banks that are slow to respond.

April 7, 202634 min

From The Set Of ABC’s Hit Show The Rookie To Republic Rum Founder, Eric Winter - Actor/Entrepreneur

Eric Winter didn't take one path. He took all of them. At once. The actor, best known as the no-nonsense Sergeant Tim Bradford on ABC's smash hit The Rookie, was once a pre-med student at UCLA on track to become a doctor. Then nearly a paramedic with the LA Fire Department, then a model, a soap opera actor, parallel paths until something clicked. While producing TV movies, pitching shows, and spinning up a podcast, another story was unfolding. On a trip to Puerto Rico to meet his future father-in-law he discovered an unexpected obsession with premium rum. That obsession became Palm Republic, an award-winning premium rum brand, 20 years in the making, now redefining what rum can be in one of the most crowded and competitive spirit markets in the world. But the headline in Eric’s story isn’t that he succeeded — it’s that he juggled it all at the same time without a playbook. Just the ambition to be a creator and build something to influence a category grounded in family and culture. On this episode of The Reboot Chronicles Podcast, we sit down with Eric Winter, actor, producer, entrepreneur, and co-founder of Palm Republic Rum, to unpack one of the most multidimensional reboot stories we've heard. Eric breaks down how a pre-med student from LA ended up on one of network television's fastest-growing shows. He explains why he built a rum brand instead of chasing the celebrity tequila wave. We discuss how patience and rejection prepared him for entrepreneurship better than any business school could. We explore his ambition for the brand and where he wants to take Palm Republic next.

April 2, 202634 min

Going Bankrupt Over a Doorbell: How Jamie Siminoff Inventor & Founder of Ring Changed the Game

Jamie Siminoff had bet everything; his savings, his family's security, and his reputation, on reinventing a device from the 1800s. At the time, he had no salary, almost no cash, and a company on the edge of bankruptcy. He had been rejected on Shark Tank with only days of runway left, not to mention a court-enforced restraining order from ADT effectively halting sales. He had $187,000 in the bank to barely cover operating expenses and needed just short of $1Million dollars to secure a four-letter domain name that could carry the brand. He was certain he was making one of the biggest mistakes in entrepreneurial history. And yet, Ring survived, and what followed became one of the most unfiltered, hard-earned comeback stories in modern entrepreneurship, ending with an acquisition by Amazon for over $1 billion with more than 100 million cameras deployed in homes worldwide.On this episode of The Reboot Chronicles Podcast, we sit down with Jamie Siminoff, inventor, and founder of Ring, to unpack one of the most unfiltered founder stories in modern tech. From the sleepless nights and bold bets to the mission-driven stubbornness that turned a simple doorbell into a global security platform. Jamie shares how he survived rejection, lawsuits, and the edge of bankruptcy. Why mission consistently outweighs money as his core motivator, and how Ring is positioning itself at the center of the AI economy by transforming more than 100 million cameras into an intelligent home platform. He opens up about his new book, Ding Dong, describing it as part business memoir and part therapy session, and one of the most honest accounts of what building a consequential, mission-based company is all about. Listen and subscribe wherever you get podcasts or at RebootChronicles.com