Andrew Rubin
Andrew Rubin is the founder and CEO of Illumio, the market leader in zero trust segmentation and cybersecurity innovation. Under his leadership, Illumio has grown to a multibillion-dollar valuation while shaping how enterprises contain breaches and protect digital ecosystems. In our conversation, Andrew reflects on the naïveté and optimism that fueled his entrepreneurial journey, the cultural mindset required to sustain innovation at scale, and why resilience and authenticity matter as much as strategy.
Cheryl McKissack Daniel
Cheryl McKissack Daniel is the CEO of McKissack and McKissack, the oldest minority-owned professional design and construction firm in the United States. She is also the author of a powerful new book, The Black Family Who Built America: The McKissack’s Two Centuries of Daring Pioneers. In the conversation, Cheryl shares the incredible story of her family’s legacy and their impact on American infrastructure. She also discusses the challenges and importance of succession planning, re-engineering a legacy company, and the invaluable role of company culture. It’s a candid look at what it takes to build a lasting enterprise.
Michael Crandell
Michael Crandell is the CEO of Bitwarden, a leading open-source password management platform trusted by millions of individuals and enterprises worldwide. A serial entrepreneur, he previously co-founded RightScale, guiding it through hypergrowth to a successful acquisition. In this conversation, Michael shares insights on scaling distributed teams, maintaining a strong culture in security-focused organizations, and why open-source transparency builds long-term trust. He also reflects on how his leadership style has evolved across multiple ventures.
Joe Moglia
Joe Moglia’s journey is unlike any other. A journey from the sidelines to Wall Street to the boardroom and back to the gridiron. As the former CEO and Chairman of TD Ameritrade, he delivered a 5X return to shareholders. As the Head Football Coach at Coastal Carolina, he built a powerhouse program from the ground up. In this episode, Joe shares the principles behind his “BAM” leadership philosophy, lessons in risk-taking and reinvention, and how to lead with clarity, accountability, and heart across any arena.
Monica Molenaar and Anne Fulenwider
Monica Molenaar and Anne Fulenwider are the co-founders and co-CEOs of Alloy Women’s Health, a fast-growing telehealth platform redefining care for women navigating hormonal changes. In this candid conversation, they share the deeply personal origins of Alloy and unpack the widespread medical gap in menopause care, highlighting how limited training and systemic shortcomings have left many women underserved. We also explore lessons from their second-act careers, the realities of building a mission-driven company, and the power of curiosity, trust, and timing in both leadership and life.
Linh Peters
Linh Peters has held senior marketing leadership roles at some of the world’s most recognizable brands, including Starbucks, Walgreens, Calvin Klein, and Target. In this episode, she shares what it takes to lead brand transformation at scale, how to build customer-centric teams, and why short tenures and fractional roles are reshaping the CMO landscape. We also explore her work as an executive coach, the challenges of translating strategy across industries, and what today’s marketing leaders need to succeed in an ever-evolving landscape.
Ajay Prakash
Ajay Prakash is the co-founder and CEO of Rinse, a company redefining laundry and dry cleaning through a managed marketplace model built on trust, technology, and consistency. In this conversation, Ajay shares his decade-long journey building Rinse from an idea into a multi-city operation with W2-employed valets, a growing brick-and-mortar presence, and a clear vision for national scale. We explore the lessons learned from scaling a service business, the intentionality behind hiring and culture, and why Ajay believes in playing the long game in both business and in life.
Hannah Gordon
Hannah Gordon spent over two decades breaking barriers in the NFL, culminating in her role as Chief Legal and Administrative Officer of the San Francisco 49ers. In this episode, she shares lessons from a remarkable career built on purpose, perseverance, and integrity — and why she made the bold decision to pause at the peak of her success to focus on family. We explore her strategic leadership style, her views on inclusive hiring and cultural alignment, and her book SZN of Change, a practical journal for leading with joy and authenticity.
Dr. John Hillen
John Hillen is a former U.S. Assistant Secretary of State, CEO, decorated Army officer, and professor of leadership and strategy. In this episode, John shares insights from his latest book, The Strategy Dialogues: A Primer on Business Strategy and Strategic Management, offering practical tools for executives navigating complexity. We discuss how dialogue sharpens strategic thinking, why leaders must build a shared vocabulary around strategy, and what separates effective decision-makers from reactive ones. A must-listen for current and aspiring C-level leaders.
Sherri Coale
Sherri Coale is a Hall of Fame basketball coach, educator, author, and speaker known for her profound ability to lead with heart and humanity. As head coach of the University of Oklahoma Women’s Basketball team for 25 years, she built a powerhouse program rooted in connection, trust, and high standards. The program experienced incredible success during this time, including 19 consecutive NCAA Tournament appearances and back-to-back Final Fours. She’s the author of Rooted to Rise and The Compost Files, two lyrical works on leadership, life, and becoming.