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 Advisory and program lead of Generative AI and Business at the University of Cambridge joins us to discuss this shift. Henry has spent the better part of a decade decoding how synthetic media will alter trust and creativity. He is with us today to help understand what a synthetic age of media really means for business, leaders, governments, and everyday people.
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.
Brad Feld is a legendary figure in the startup world whose influence runs deep and wide. As co-founder of both the Foundry Group and Techstars, Brad has helped shape the very ecosystem that fuels innovation today. He was an early investor in breakout successes like Zynga and Fitbit, spotting potential long before they became household names. Beyond investing, he's also a prolific author whose books have become essential reading for founders navigating the rocky-road highs and lows of entrepreneurship.
Through his success and headline investments, Brad has built a legacy through his philosophy of giving first, radical honesty about mental health, and a pursuit of personal and professional rebooting. Join us for a deep dive into Brad Feld’s remarkable journey, as we uncover the stories, insights, and hard-won lessons that can help you—and continue to shape the future of business.
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 lead the next generation of business.
Jim Peko is CEO of Grant Thornton, part of Grant Thornton International, an $8 billion group with 76,000 employees in hundreds of offices worldwide. Jim is making no small plans for their reboot; they have brought in a top private equity partner to think bigger and accelerate Jim's plans. Listen in as we unpack this ambitious reboot and how, through a billion-dollar investment from New Mountain Capital, they plan to supercharge the AI-enabled services sector—and how you can be an AI disruptor.
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 across multiple ventures, most notably steering DeepLens, a pioneering platform for clinical trial patient-matching, through its successful acquisition by Paradigm Health. Today, he’s at the helm of Ryght Inc., where he’s harnessing generative AI to revolutionize Biopharma site selection—making it faster, smarter, and more cost-effective.
Simon’s journey is one of ongoing evolution from early promise to Olympic excellence, and now a visionary leader reshaping healthcare through technology. Join us as we unpack the many reboots that shaped his path—and explore what’s next on his horizon.
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 includes global fame, entrepreneurial grit, and a mission-driven future.
On this episode of the Reboot Chronicles Podcast, Taylor shares his remarkable musical career journey, where they have sold 16 million records, with eight Top-40 Albums, three Top-40 singles, and three Grammy nominations. This musical fame was only their beginning. Today, Taylor is the co-founder of Hanson Brothers Beer Company, a craft brewery rooted in community and creativity, and is actively developing a nonprofit initiative focused on civic engagement and social impact. In a business that often sidelines authentic voices, Taylor’s path underscores the power of speaking up, standing firm, and creating ventures that reflect your values. Listen in for some fun stories and a few surprises.
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, Stephenson brought charisma, controversy, and championship grit, capturing 16 LPGA titles, including three majors, and earning Rookie of the Year honors in her debut season.
But her legacy isn’t just etched in scorecards—it lives in the way she turned golf into a stage, and herself into a story of inspiration, resilience and lasting impact by transforming reboot moments into opportunities. Having beat cancer twice, she is fierce in the face of adversity; showing no signs of slowing down as she shares her passion with her foundation, as an entrepreneur and a champion for the sport of golf around the world.
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 Dimension 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.
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.
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 chairman 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.
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.
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.
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.
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.
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 reboots of our decade.For Kantar, the struggle over the last decade has been real, as they have been through multiple reboots, adapting to the global power shifts in the market. The first reboot came with a mandate to breakup some of the pieces and spinout the company from the WPP Mothership through a partnership with Bain Capital. Now on their own, Kantar is a $3.5B marketing data and analytics powerhouse with 25,000 employees operating in 100 countries. With massive backing from Bain they have an opportunity to invest in next-gen areas, like AI and automation, and seize what’s next. But it won’t be easy to fight back and disrupt the disruptive disruptors.Watch or listen as we unpack this exciting reboot in progress, as they search for the perfect balance of AI and human-driven data—with a sneak peek into the future in this frothy hyper-competitive market being disrupted by AI.
When it comes down to brands that put 110% into customer experiences, few have managed to create something as sweet 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.
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 topics we’ve been talking about on the show: AI, with all its hype, and cybercrime, which is becoming more and more of a threat in line with our ever-expanding digital footprints. Between phishing links, deepfakes, and scam calls, more than a trillion dollars were lost globally last year alone, and today’s guest on the Reboot Chronicles, DataVisor CEO Yinglian Xie, is combating the surge. Yinglian is a former Microsoft Researcher that turned tech entrepreneur with a new mission in mind; to stay as many steps ahead of cybercriminals as possible. At the cutting-edge intersection of AI, cybersecurity, and fintech, she has built a company that isn’t just fighting fraud, it’s redefining how the world protects itself in real time. And for those of us who continue to get sketchy emails in our inboxes—this is good news!
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 most successful software IPO of 2017 with only $10 million of pre IPO capital. Most CEOs don’t raise capital so efficiently before going public—which is one reason we wanted him on the show. I guess also because Dean did the same thing, as the CEO of Autoweb, which he took public at a billion-dollar valuation. It’s a small club…but getting bigger with AI companies.
This rapidly growing group now has a $2B market cap and thousands of employees that have rebooted into a ‘Process AI’ firm built to enable a ‘worker’ model for organizations.Hot off the heels of their World Conference, where they unpacked the future of tech, and how to put AI to work, Matt cuts through the hype to help us peer around corners with a realistic take on what’s next for our organizations and our lives.
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 they did it—in good times and bad. Steve was the founding Chief Marketing Officer of Chick-fil-A, where he and Founder Truett Cathy, built the most unconventional franchise model by doing something the world’s top corporations struggle with—prioritizing People over Profits. And it worked.
After some setbacks, Steve went on to create the most iconic fast-food advertising campaign—that not only differentiated them in a sea of fast-food sales-focused chains—but rebooted an industry. Now with over 3000 locations Chick-fil-A is one of three brands with U.S. sales over $20 billion, along with McDonald’s and Starbucks.
He went on to became a Chick-fil-A board member and authored Covert Cows and Chick-fil-A: How Faith, Cows, and Chicken Built an Iconic Brand. It, and this episode, is the inside story of how they rebooted the sector, turning prevailing theories of fast-food marketing upside down while building one of the most successful and beloved brands in America.
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 AI chip powerhouses that has built some of the world's fastest supercomputers. This increase in speed wasn’t just a few percent faster either, tests are showing that Cerebras' work came in up to 75 times faster than their competitors. Cerebras CMO, Julie Choi, joins this episode of The Reboot Chronicles Show for an insider’s look into how they created the next-gen technology which is driving their record-breaking success. Julie has seen Cerebras through their $700 million in funding, filing to take the company public to raise $1B, and building strategic partnerships with businesses like the Mayo Clinic and the Department of Energy. Now, on a mission to accelerate generative AI by building a new class of AI supercomputer, that could change the course of progress, Julie shares stories about both the nerdy side of chips and the future of technology as this industry hits breakneck speeds around the globe.
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 one of the fastest-growing insurance companies in the world, which has acquired hundreds of companies that serve over 300,000 clients through 250 carriers in 300 locations—and they are just getting started again.World continues to lead the market, and their acquisition hot streak, with an additional $1B investment from Goldman Sachs—rocketing them to a $2 billion premium platform. Rich and his team are living the aggressive growth story that most CEO’s only dream about. Follow along as we unpack the secrets of this record-breaking organization, how they are leveraging AI technology, along with the spoils and tough challenges that come with the journey.