CEOs and ABCs

Robert LoCascio went public at 33, helped invent web chat, and spent nearly three decades building LivePerson into a $6 billion company. What followed was not the ending he expected.

In this episode of CEOs & ABCs, Kevin Rice sits down with the founder of LivePerson for a rare and deeply honest conversation about leadership under extreme pressure, navigating macro events like the dotcom crash, 9/11, and COVID, and what happens when the greatest threat comes from inside the system. Rob opens up about activist investors, an unplanned exit from the company he built over 28 years, and the emotional toll that season took on his identity and his family.

Rob shares the hard-earned leadership lessons that shaped him, from the moment a board member told him “just don’t bullshit them,” to why the best response to chaos is often no response at all. He explains why slowing down during crises creates clarity, how fear-based decisions compound risk, and why your weakest links matter most when you’re under attack. The conversation also explores fatherhood, marriage later in life, and what it looks like to rebuild from scratch.

Today, Rob is starting again in a completely different space, building a kid-first AI product designed around safety, creativity, and bringing families back into connection. This episode is a masterclass in resilience, integrity, and what it really means to begin again when the game changes.

In This Episode You’ll Learn

- What it’s like to take a company public at 33
- How to lead through layoffs with honesty and integrity
- Why slowing down is critical during macro crises
- How fear distorts decision-making at the executive level
- What activist investors really do behind the scenes
- How leadership pressure spills into family life
- Why rebuilding sometimes means starting from zero
- How fatherhood reshaped Rob’s definition of success
- Why imposter syndrome may actually be your inner child
- How to think about AI, kids, and creativity responsibly

Top Takeaways

- Truth builds long-term trust, even in the hardest moments
- The worst decisions are made when fear is driving
- Macro events should be observed before they’re reacted to
- Weak leadership links are exposed under pressure
- You cannot dump the business onto your family and stay connected
- Success brings visibility, and visibility brings risk
- Resilience is modeled, not taught
- No one can take your ability to create and rebuild
- Starting over can unlock deeper purpose

About Robert LoCascio
Robert LoCascio is the founder of LivePerson and a pioneer of internet-era customer communication, credited with inventing web chat. He took LivePerson public in 2000 and led the company for nearly 30 years, growing it to a peak market capitalization of over $6 billion. Today, Rob is the founder of KID, a kid-first AI product designed to empower creativity, ensure safety, and strengthen family connection. He is also a father of three and a lifelong builder focused on integrity, imagination, and impact.

Jessica Serrano has spent nearly two decades shaping some of the world’s most loved food brands, but what makes her story hit is the way she’s built a life that can hold both motherhood and executive ambition.

In this episode of CEOs & ABCs, Kevin Rice sits down with the CMO of Bagel Brands (Einstein Bros and Noah’s Bagels) to talk about what it really takes to lead at a high level without feeling like you’re constantly choosing between work and family. Jessica shares the full circle moment of starting a new CMO role on the exact day her twin daughters started kindergarten, with three generations in one car on day one. From multi generational living and cross country moves to ruthless prioritization and energy protection, she breaks down the real systems that keep her grounded.

They also go deep on career growth, including the hard lessons that came with moving into the C suite, why conviction matters when you report to a founder, and how she evaluates roles using a skill building matrix so she doesn’t fall in love with the fireplace. If you’re trying to grow your career, stay present at home, and lead with clarity, this conversation will give you both perspective and practical tools.

In This Episode You’ll Learn

Top Takeaways

About Jessica Serrano

Jessica Serrano is the Chief Marketing Officer of Bagel Brands, home to Einstein Bros and Noah’s Bagels. She has led culturally resonant marketing across some of the biggest names in food, including leadership roles at Taco Bell and Burger King, and she helped drive brand and growth as CMO at Dig Inn. Jessica is known for blending business rigor with warmth and creativity, and for building teams and brand strategies that connect deeply with consumers while staying grounded in what matters most at home.

Rishad Tobaccowala believes work is changing more between 2020 and 2029 than it did in the previous fifty years. In this conversation, he joins Kevin Rice to unpack what those waves of change look like across society, demographics, technology, marketplaces, and emotion, and why return-to-office debates miss the bigger picture. Rishad shares practical ways leaders can design organizations around trust, flexibility, dignity, and outcomes so people and performance both thrive.

They dive into how to measure engagement instead of attendance, why skills will matter more than roles, and how to build cultures that create belonging while still raising the bar. Rishad also previews his new Rethinking Work Platform and show, a resource hub for leaders navigating the next era of work with clarity, courage, and humanity.

In this episode you’ll learn:

Top takeaways

About Rishad Tobaccowala
Rishad Tobaccowala is the founder of the Rethinking Work Platform, a new initiative helping leaders navigate a decade of unprecedented change with content, curated resources, and actionable guidance. A globally respected advisor and storyteller, Rishad has spent his career helping companies align people, technology, and strategy so work becomes both more human and more effective.

Links:

⁠Rishad Tabaccowala Home Page⁠

⁠What's Next? Podcast ⁠

⁠Rethinking Work by Rishad Tobaccowala ⁠

⁠Restoring the Soul of Business ⁠

In this raw, honest, and deeply reflective conversation, Kevin Rice sits down with Deborah Palmer Keiser, global operator, supply-chain builder, fear-tamer, and now COO of Pair of Thieves, to explore the cost of ambition, the courage to repair, and the surprising ways our kids teach us to lead.

Deborah spent three decades opening markets, fixing broken supply chains, and resurrecting brands across the world, from Gap and Williams-Sonoma to Victoria’s Secret, AllSaints, Boardriders, and Yeezy. She built a reputation as the operator companies call when it’s time to grow up and get serious. But behind the promotions, global travel, and relentless execution was a young daughter quietly taking inventory of all the moments her mom missed.

The turning point came when seven-year-old Tilly asked to see the family’s bank balance, not because she cared about money, but because she wanted to know why her mom kept choosing work over her. That one question cracked Deborah open. It sparked a five-year process of repair, reconnection, and relearning how to sit still long enough to paint nails, draw pictures, and rebuild trust one quiet moment at a time.

Deborah shares how being fully present with her daughter made her a better leader, more human, more honest, and more clear about her limits. She explains why becoming “truthfully unavailable” actually strengthened her teams, empowered emerging leaders, and deepened commitment across her orgs. And she reflects on what her daughter taught her about emotional articulation, empathy, and creating space for others to be fully themselves.

Together, Kevin and Deborah explore what it means to raise a young artist in a world that pushes safe careers, why fearlessness can be both a gift and a trap, and how childhood instability shaped Deborah’s early beliefs about success, security, and motherhood. They talk about global cultures that integrate family into daily life, and what America gets wrong about excellence, work, and worth.

This is a conversation about the long road back to connection, the humility of repair, and the kind of leadership that grows not from ambition, but from love.

In this episode, you’ll learn:
• Why a seven-year-old’s question about money became Deborah’s wake-up call
• How to repair a parent–child relationship after years of distance
• Why presence, not provision, is the foundation of trust at home
• How becoming “unavailable” at work actually made Deborah a stronger leader
• What global cultures teach us about integrating family into professional life
• How fearlessness can morph into self-isolation and what breaks the cycle
• Why dragging people uphill fails and how servant leadership changes everything
• How childhood instability shaped Deborah’s early beliefs about success
• What it means to raise a young artist in a world obsessed with productivity
• Why taking your dream all the way is the antidote to lifelong regret

Top Takeaways:
• You can provide for your kids and still lose connection with them. Repair requires presence, not perfection. • Kids often tell the truth adults avoid. Listening to them takes courage, but it changes everything.
• Leadership rooted in humanity invites teams to step up, not step back.
• Your greatest strengths, fearlessness, independence, self-reliance, can become your greatest limits if left unchecked.
• The stories we inherit from childhood quietly shape every decision we make as adults.
• Openness builds trust. Pretending to “hold it all together” builds distance.
• Culture is people. People stay (or leave) because of who you are, not what you produce.
• Every path is hard. You might as well choose the one that makes you feel alive.
• Taking your dreams seriously is an act of courage and self-respect—and the same is true for your kids.

About Deborah Palmer Keiser:
Deborah is a globally experienced operator and supply-chain leader who has scaled, stabilized, and transformed some of the world’s most iconic retail brands. Across 30+ years, she has held leadership roles at Gap, Williams-Sonoma, Victoria’s Secret, Boardriders, AllSaints, and Yeezy. Today, she serves as COO of Pair of Thieves, guiding mid-size brands through operational maturity and sustainable growth. A devoted mother and champion of young creatives, Deborah blends operational rigor with profound emotional wisdom—leading with transparency, service, and heart.

In this thought-provoking and deeply human conversation, Kevin Rice sits down with Amanda Slavin, educator, author, consultant, and creator of the Seven Levels of Engagement, to unpack why engagement, not productivity, is the real engine of learning, leadership, and parenting.

Amanda shares the origin story of her life’s work, starting with her own childhood report cards that all said the same thing: “Amanda talks too much.” What teachers saw as disruption was actually early evidence of her lifelong obsession with connection, curiosity, and conversation. That spark eventually led her to become a teacher, earn a master’s in education, study pedagogy across wildly different school environments, and discover a taxonomy that would shape the next decade of her career.

Together, Kevin and Amanda explore how the Seven Levels of Engagement help decode what’s really happening in classrooms, teams, and families. They talk about why kids melt down when parents get distracted, how quiet quitting begins long before someone stops performing, and why the real opposite of engagement isn’t disengagement, it's apathy.

Amanda also opens up about how she applies her framework at home with her five- and three-year-old, and why she collaborates with them on consequences instead of handing down punishments. She explains why connection is the cheat code in parenting, why incentives rarely create long-term motivation, and how repair, presence, and respect model emotional maturity for kids who rely on our nervous systems to regulate.

From bedtime battles to bored employees, from distracted leaders to overwhelmed parents, this episode is filled with real stories, practical tools, and the kind of grounded insights that make you rethink how you show up.

Whether you lead teams, raise tiny humans, or both, this conversation gives you a blueprint for building cultures of connection in every corner of your life.

In this episode, you’ll learn:
• Why engagement is not binary and why each of the seven levels matters
• How extrinsic rewards shortcut compliance but reduce creativity, curiosity, and connection • The difference between consequences and punishments and why one teaches while the other controls
• How a parent’s distraction can drop a child from “inspired and connected” to stressed and overwhelmed
• Why apathy, not disengagement, is the real danger zone in the workplace
• How to spot quiet quitting before it happens
• How to create psychologically safe cultures where people feel seen, valued, and motivated • Why presence and accountability matter more than perfection in parenting
• How the same engagement principles used at Google and Coca-Cola apply to bedtime routines
• Why respect is the foundation of every relationship from toddlers to executives

Top Takeaways:
• Distraction destroys connection faster than anything else.
• Consequences teach; punishments shame.
• Kids’ regulation relies on our regulation, until age 25.
• Engagement is nuanced; productivity alone is not a measure of alignment or meaning.
• Quiet quitting starts with feeling unseen long before performance drops.
• Intrinsic motivation fuels creativity, collaboration, and long-term commitment.
• Culture becomes real when values are measurable, not decorative.
• Repair is more important than getting it right the first time.
• Presence is the foundation of trust at home and at work.
• Apathy, not disengagement is what leaders must prevent.

About Amanda Slavin:
Amanda Slavin is an educator-turned-consultant, author of The Seventh Level, and creator of the Seven Levels of Engagement framework. With a master’s in education and years of experience inside classrooms across diverse environments, she spent a decade helping global brands, including Google, Coca-Cola, and Nestlé, build cultures of meaningful engagement. A mother of two young children, Amanda blends research-backed frameworks with real-life parenting, modeling respect, presence, and connection in the moments that matter most.

In this revealing and deeply personal conversation, Kevin Rice sits down with Adam Brotman, renowned digital innovator, CEO of Forum3, and former Chief Digital Officer at Starbucks, to explore how great leadership begins at home.

Adam shares the untold story behind Starbucks’ digital transformation, the strategy that reshaped the way millions of customers order coffee and connect with brands and the lessons that came from leading that change. From architecting mobile order and pay to stepping into the co-CEO role at J.Crew, Adam opens up about the costs of burnout, the courage to set boundaries, and the decision to become a primary parent.

Together, Kevin and Adam dive into the evolution of leadership, learning through failure, and the transition from ambition to purpose. They discuss how COVID redefined presence, why Zoom parenting became a gift in disguise, and what it means to raise grounded, creative children in an AI-native world. Adam also reflects on the values he hopes to pass on to his daughter, to be a good listener, a good learner, and a good friend and how those same principles guide his leadership today.

Whether you’re leading a company, navigating burnout, or redefining success beyond your career, this episode offers both practical wisdom and heart-centered reflection on what it truly means to build a meaningful life.

In this episode, you’ll learn
• How Starbucks’ digital flywheel became a blueprint for connection
• The warning signs of burnout and how to realign with purpose
• Why setting boundaries is a leadership superpower
• How becoming a parent reshapes your definition of success
• The lessons COVID taught us about presence and flexibility
• How to prepare your kids for an AI-driven future
• Why authenticity and reflection create stronger leaders

Top takeaways
• Great leadership starts with self-awareness and boundaries
• Burnout is a signal to realign, not a failure
• Parenting teaches empathy, patience, and humility, the same skills that drive effective teams
• The future of work will favor creativity, adaptability, and emotional intelligence
• Legacy is built through presence, not performance

About Adam Brotman
Adam Brotman is the co-founder and CEO of Forum3, author of AI First, and a celebrated digital innovator best known for architecting Starbucks’ digital transformation, including mobile order and pay. He previously served as co-CEO of J.Crew and co-founded Brightloom, a restaurant technology company. A proud father and husband, Adam is passionate about creating meaningful customer experiences and about helping the next generation prepare for a rapidly changing world.

In this thoughtful and wide-ranging conversation, Kevin Rice sits down with Nick Tran, President and CMO of the joint venture between Diageo and Main Street Advisors, to talk about what it means to design a life, not just a career.

Nick shares how taking a mid-career sabbatical and moving his young family to London became one of the most rewarding chapters of his life. Over three years and 23 countries, he learned that kids are far more adaptable than we give them credit for and that presence, not perfection, is what they remember most.

Together, Kevin and Nick explore how to balance ambition with intention, the importance of setting boundaries in high-pressure roles, and the mindset shifts that come from slowing down. Nick also opens up about his parenting approach from limiting social media and encouraging curiosity to teaching kindness, generosity, and resilience as the skills that will matter most in the future.

Finally, Nick reflects on his career path from leading global marketing at TikTok, Taco Bell, and Samsung, to helping others find their voice as leaders. He shares why he measures success by the number of people from his teams who have gone on to become CMOs, and why he believes personal branding is essential for every modern professional.

In This Episode You'll Learn:
• Why designing a life matters more than chasing titles
• How living abroad can reshape family connection and perspective
• The power of intentional parenting and setting family milestones
• Why screen time and social media guardrails are essential for kids
• How to teach generosity, kindness, and resilience through action
• Why curiosity and learning how to learn matter more than hard skills
• How to build authentic relationships that elevate your career
• Why personal branding is a critical leadership skill

Top Takeaways:
• Presence and boundaries create balance in demanding careers
• Travel teaches adaptability, empathy, and global perspective
• The best lessons for kids come from lived experience, not lectures
• Generosity and curiosity are the foundation of lifelong leadership
• Building others up is the true measure of success

About Nick Tran:
Nick Tran is the President and CMO of the joint venture between Diageo and Main Street Advisors, overseeing brands like Lobos 1707 and Ciroc Vodka. Previously, he led global marketing at TikTok, Samsung, Taco Bell, and Hulu, where his work helped define cultural relevance for modern brands. Nick is also a devoted father who believes leadership starts at home, through presence, purpose, and the courage to design life intentionally.

In this honest and energizing conversation, Kevin Rice sits down with Chris Andrews, Chief Information and Digital Officer at European Wax Center, to explore how leadership at work intersects with leadership at home.

Chris reflects on the milestone of dropping his twins at college and feeling joy instead of tears, the daily discipline that kept him present for family while leading large transformations, and how returning to Brazilian Jiu-Jitsu helped him rebuild health, clarity, and calm under pressure.

Together, Kevin and Chris unpack seasons of stress, the signals that work is intruding on family life, and why authentic leadership and supportive cultures matter more than ever. Chris shares the lessons he wants his kids to carry forward: kindness, resilience, and the courage to keep showing up even when it is hard.

In this episode, you will learn:

• Why physical health is a leadership advantage
• How Brazilian Jiu-Jitsu builds calm, confidence, and composure
• Practical ways to protect special family moments on a tight schedule
• How to notice when career pressure is crowding out presence at home
• Why authentic leadership deepens trust and connection with teams
• How to create a supportive work culture that lifts people up
• What career setbacks can teach you about grit and growth
• How to model kindness and resilience for your kids

Top Takeaways:

• Presence is built through discipline and protected rituals
• Health fuels better decisions and steadier leadership
• Authentic leadership starts at home and shows up at work
• Supportive cultures are created by consistent daily choices
• The legacy that matters most is who your kids become

About Chris Andrews: Chris Andrews is the Chief Information and Digital Officer at European Wax Center. He has led complex digital transformations at well-known multi-unit brands and is passionate about building healthy teams, supportive cultures, and a life where career and family strengthen each other. Outside the office, Brazilian Jiu-Jitsu keeps him grounded, focused, and calm under pressure.

In this candid and energizing conversation, Kevin Rice sits down with Deena DePhilips, CIO of Red Robin, to explore how becoming a mother transformed her leadership, her relationship with time, and her definition of success.

Deena shares the raw reality of stepping into the CIO role just five weeks after giving birth and the crash that followed when the old “workhorse” playbook stopped working. She opens up about rebuilding from burnout, trading perfectionism for presence, and shifting from doer to strategist by empowering her team.

Together, Kevin and Deena dig into parenting as a mirror for leadership, breaking generational patterns, and creating boundaries that protect what matters most. Deena lays out the three lessons that changed everything for her: deep focus in short windows, falling in love with fluidity, and embracing “done is better than perfect.”

Whether you are navigating a big promotion, new parenthood, or both at once, Deena’s story offers practical tools and hard-earned encouragement for leading with clarity at work and at home.

In this episode, you’ll learn:

• Why motherhood can be a launching pad, not a pause
• How to compress deep work into focused 60 to 90 minute sprints
• Tactics for choosing presence when work never truly turns off
• Why fluidity beats rigid routines in high-pressure seasons
• How to move from workhorse to strategist by empowering others
• Ways to protect sacred family time, especially bedtime rituals
• How parenting sharpens empathy, patience, and listening at work
• Why legacy is built through daily deposits in the connection bank

Top Takeaways:

• Presence over perfection creates more impact in both roles
• Focus and discipline matter more than long hours
• Let go or be dragged is a powerful mindset for change
• Done is better than perfect keeps momentum moving
• Work can be a passion, but family is the purpose that sustains it

About Deena DePhilips:
Deena DePhilips is the Chief Information Officer at Red Robin, where she leads enterprise technology and digital transformation. Known as both a workhorse and a visionary leader, she has built a reputation for simplifying complex systems and empowering high-performing teams. Deena is also a devoted mother who believes that work is her passion and her daughter is her purpose.