The Reboot Chronicles with Dean DeBiase

Hosted by Dean DeBiase

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236

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Aug 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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August 27, 202634 min

Breaking the Iteration Trap: Dave Wright, Chief Innovation Officer at ServiceNow

Most companies deploying AI are making the same mistake. They are using it to do what they already do, faster and cheaper, and then wondering why the return on investment does not materialize. Dave Wright calls this the iteration trap, and breaking out of it is the central argument of his new book, Infinite, co-written with ServiceNow futurist Brian Solas. As chief innovation officer at ServiceNow, Wright has watched the company grow from 300 employees to 30,000, worked alongside every CEO the company has ever had, and spent decades building the actual systems that run inside thousands of the world's largest corporations. His perspective on AI is not theoretical. It is grounded in what happens when organizations stop asking how to automate what they already do and start asking what they want to become. The difference between those two questions, Wright argues, is the difference between AI as an incremental efficiency tool and AI as a genuine operating model for business reinvention. On this episode of The Reboot Chronicles Podcast, we sit down with Dave Wright, chief innovation officer at ServiceNow, to unpack why most AI strategies are failing before they start, how IKEA turned a customer service automation project into a billion euro revenue stream, what a hybrid workforce of humans and agents actually looks like in practice, why every company needs a chief workflow officer, and what it means to lead innovation inside one of the fastest growing enterprise software companies in the world. Wright also shares what he has learned from working under four very different CEOs and why the chief innovation officer might be both the best and worst job in any company.

August 19, 202635 min

Lighting Up the AI Era: Michael Hurlston, CEO of Lumentum

Inside every AI data center, behind every GPU cluster, underneath every rack of compute and storage, there is a connection problem. For decades that problem was solved with copper. Copper cables connected computer storage to switching, and the system worked well enough. Then AI arrived and the speeds required to move data across those connections exceeded what copper physics can handle. The answer is fiber optics and the lasers that power them. That is the business of Lumentum, and it is why Nvidia wrote a two billion dollar check to make sure the supply was locked up. Under CEO Michael Hurlston, Lumentum has rebooted itself from a telecom-era optical components company into one of the most strategically critical infrastructure players in the AI economy. Revenue is on track to more than double from 1.5 billion dollars last year to over 3 billion this year. The stock has surged more than 1,500 percent. And the company is investing three years ahead of demand, building a new indium phosphide fabrication facility in Greensboro, North Carolina, to supply the laser chips that data centers will need as the conversion from copper to fiber optics accelerates. On this episode of The Reboot Chronicles Podcast, we sit down with Michael Hurlston, CEO of Lumentum, to unpack why lasers and fiber optics are the invisible infrastructure layer the AI economy cannot function without, how the company is managing the challenge of scaling from thousands of units per quarter to potentially hundreds of millions, why Lumentum is making a pure play bet on the data center opportunity while de-emphasizing other markets, and what it takes to lead a public company through rocket ship growth. Hurlston also shares the personal reboot story behind his career, including the catastrophic startup failure that ultimately sent him to Broadcom and set the foundation for everything that followed.

August 12, 202635 min

Automating the Future: Darragh de Stonndún, CEO of AIR

Every medical device implanted in a patient, every cell phone produced at launch scale, every vaccine vial filled at twelve hundred units per minute exists because of industrial automation. It is the invisible infrastructure behind modern manufacturing, and it is one of the fastest growing sectors in the global economy. Darragh de Stonndún has spent his entire career at the center of it. After leaving Ireland in 1998 in pursuit of the automation innovation happening in America, he spent decades building and leading automation businesses across the US, Germany, Ireland, and the UK. In August 2024, he co-founded AIR, an automated industrial robotics platform that has already acquired six best-in-class automation companies across three countries, grown to more than 500 employees, and is producing hundreds of millions in revenue. The timing could not be better. Reshoring, semiconductor expansion, and the race to automate manufacturing across life sciences, logistics, and consumer electronics are pushing the sector toward a hundred billion dollar market. AIR is building the platform designed to serve that market, and de Stondún is building it the same way he has always built machines: with precision, discipline, and an obsessive focus on getting every part of the system right. On this episode of The Reboot Chronicles Podcast, we sit down with Darragh de Stonndún, CEO of AIR, to unpack how he is building a unified automation powerhouse rather than a collection of acquired companies, why automation is no longer optional for manufacturers competing in a reshored America, how AI is reshaping what is possible in industrial robotics, what humans in the loop actually means on a factory floor, and why the biggest challenge in building AIR is not technology but separating signal from noise in a market moving faster than ever.

August 5, 202638 min

Rebooting Silicon: Raja Tabet, SVP at Synopsys

Every drone, autonomous vehicle, AI agent, and smart device running in the world today depends on silicon. And the software that enables that silicon to be designed, verified, and manufactured at scale is the domain of Synopsys. With nearly 28,000 employees and a clear path toward becoming a 10 billion dollar company, Synopsys has spent nearly four decades building the electronic design automation tools that chip companies cannot operate without. Now, with the acquisition of Ansys completed one year ago, Synopsys has expanded its platform from chip design into full system simulation, covering thermal, mechanical, fluid, and electrical considerations simultaneously. The result is a company that sits at the intersection of every major technology wave reshaping the global economy, from AI and data centers to autonomous vehicles, robotics, and quantum computing. Raja Tabet, senior vice president of strategic missions and technology at Synopsys, leads the forward-leaning portfolios at that intersection and has spent decades navigating the edge of what is possible in semiconductor design and systems engineering. On this episode of The Reboot Chronicles Podcast, we sit down with Raja Tabet, SVP at Synopsys, to unpack why silicon is the most fundamental enabler of the pervasive intelligence era, how the Ansys acquisition transformed Synopsys into a full stack partner for system builders across every major industry, what digital twin technology means for the future of data centers and product development, how Synopsys is navigating deep partnerships with Microsoft and Nvidia while remaining neutral across the broader ecosystem, and what the next generation of engineers needs to understand to stay relevant in a world where AI is handling more and more of the coding

July 29, 202637 min

The Age Rebellion: Lyndsey Simpson, CEO of 55 Redefined

The systems built around work, retirement, and aging were designed for a world where people lived to their seventies. That world no longer exists. A 70 year old today has the same mental and physical acuity as a 53 year old in the year 2000. The fastest growing group of new entrepreneurs in the United States and across Europe are first time founders over 50, who are three times more likely to succeed than their younger counterparts. And 75 percent of global wealth is held by people between the ages of 50 and 70, yet only 5 percent of advertising targets that demographic. Lyndsey Simpson saw this mismatch before most people were talking about it. After scaling one of the UK's largest HR and recruitment outsourcing firms, she made a deliberate pivot and launched 55 Redefined, an age inclusion platform now working with more than 300 global corporate partners including Amazon and Warner Brothers. Her mission is straightforward: add ten productive years to people's lives while helping companies unlock the commercial value of experience. Her new book, The Age Rebellion, is a practical manifesto for rejecting outdated assumptions about aging and designing the second half of life with intention. On this episode of The Reboot Chronicles Podcast, we sit down with Lyndsey Simpson, CEO of 55 Redefined, to unpack the business case for age inclusion, why retirement is a trap most people do not see coming, how self limiting beliefs about aging are literally shortening lives, and what it means to be an age pioneer in a generation that has no playbook to follow. Simpson also shares the unexpected moment that sparked her company, the data behind the return on experience, and the practical framework she uses to help people design what comes next.

July 22, 202636 min

Securing the Agentic Era: Eric Kelleher, President & COO of Okta

Identity has become the most critical perimeter in enterprise security, and no company is more focused on that reality than Okta. As President and Chief Operating Officer, Eric Kelleher has helped steer Okta through multiple reboots, from solving the functional problem of employee access management in the early cloud era, to repositioning the company as a core security platform, to now tackling what may be the most consequential challenge in enterprise technology: securing the identities of AI agents operating autonomously inside corporate networks. With nearly 3 billion dollars in revenue, more than 6,000 employees, and over 20,000 enterprise customers across every major industry, Okta is the infrastructure layer that organizations rely on to verify that the humans, systems, and now agents acting inside their companies are who they say they are and authorized to do what they are attempting to do. Before Okta, Kelleher helped write the SaaS playbook at Salesforce, scaling the company from roughly 50 million to 4 billion dollars in revenue, and built LinkedIn's first customer success organization, growing the talent solutions business to 2 billion dollars. On this episode of The Reboot Chronicles Podcast, we sit down with Eric Kelleher, president and COO of Okta, to unpack how identity became the new security perimeter, why the agentic AI wave is creating an entirely new category of security risk that most enterprises are not yet prepared for, how Okta's open standard for cross-app access is designed to give the industry a baseline for securing agents regardless of which vendor built them, and what the next five years of identity security will look like as the workforce shifts from human to machine. Kelleher also shares the personal reboot story behind his career, including what he learned from bankrupting a SaaS company during the dot-com crash while house poor in Silicon Valley with his first child on the way.

July 16, 202633 min

Building the Backbone of Global Finance: Peter Hughes, CEO of Apex

Twenty-three years ago, Peter Hughes found himself frustrated by the inconsistency in asset management and fund administration reporting across providers. Large clients received great service, smaller and newer asset managers, the ones who needed fast, reliable reporting most urgently, were left behind. So, Hughes built something different. Today, Apex is a multi-billion dollar financial services platform with 3.6 trillion dollars in platform assets, 13,000 employees, and more than 100 offices across 50 countries. The company processes billions in transactions for hundreds of financial institutions, asset managers, brokers, banks, fintechs, and Web3 innovators who rely on Apex to scale securely, compliantly, and globally. What Hughes built was not just another services firm. It was the infrastructure layer that lets companies expand internationally without the regulatory drag and legacy systems that slow things down. Now Apex is applying that same model to the next frontier, crypto, digital assets, tokenized markets, and institutional grade custody, enabling firms to operate in a world where finance is increasingly programmable and borderless. On this episode of The Reboot Chronicles Podcast, we sit down with Peter Hughes, CEO of Apex, to unpack how he built one of the most expansive financial services platforms in the world, how Apex survived the 2008 financial crisis, why tokenization is not about crypto speculation but about democratizing access to quality investments, and what the future of finance looks like when retirement portfolios are liquid, borderless, and on chain.

June 17, 202634 min

From the NBA to the Nation Building: Charles D. Smith, Chairman & CEO of Urban Icon Global

Charles D. Smith spent his career as one of the NBA's premier shot blockers and an Olympian, but the transformation that defined his second act required something far more difficult than anything he faced on the court. After retiring from professional basketball, Smith spent seven years in therapy rebuilding how he thought, communicated, and led, a process he describes not as a transition but as a full transformation. Today, Smith is chairman and CEO of Urban Icon Global, a company working directly with governments and civic leaders across Africa to design sports, entertainment, and economic development projects. His investment conferences and cross cultural initiatives have generated over a billion dollars in collaborations across five continents, connecting CEOs, dignitaries, private equity firms, and family offices from New York to Dubai. With operations now active in Zanzibar and expanding into Nairobi, Ethiopia, and Uganda, Smith is positioning Urban Icon Global to unlock a piece of the 40 billion dollar African sports and entertainment market, built on a humanitarian foundation rather than a real estate model. On this episode of The Reboot Chronicles Podcast, we sit down with Charles D. Smith, chairman and CEO of Urban Icon Global, to unpack how he rebuilt himself after professional sports, why he chose Zanzibar as the starting point for an East African expansion, how faith and relationships became the foundation of his business strategy, and what it takes to build a scalable platform in a market most investors still misunderstand. Smith also shares the personal story behind his approach to leadership, accountability, and legacy.

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.