The Reboot Chronicles with Dean DeBiase

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

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.

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.

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.

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.

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.

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.

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.

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.

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.