The Reboot Chronicles with Dean DeBiase

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 Founder 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.

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 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.

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.

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.