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.
Suzanne Heske
Suzanne Heske is a Partner at SPMB, where she leads the firm’s investment practice, recruiting senior investors, operating partners, and functional leaders across venture capital, private equity, and asset management. With a career that spans Wall Street and Silicon Valley, Suzanne brings rare insight into how capital and talent intersect and what it takes to lead in a rapidly evolving landscape. In this episode, Suzanne discusses succession planning, firm culture, and the surprising paths into VC leadership.
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.
Erik Blachford
Erik Blachford helped pioneer the online travel industry as a founding executive at Expedia, eventually serving as its CEO. Since then, he’s built a career as a board member and investor in iconic consumer tech companies, including more than 20 years on the board at Zillow. In this episode, Erik shares a wide range of insights on CEO leadership, company culture, board governance, and the future of AI. We also talk about his early jobs in adventure travel, his theater background, and how storytelling and cadence shape enduring organizations.
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.
Jenna Fisher
Jenna Fisher is a leading voice in executive search and the head of the Global CFO Practice at Russell Reynolds Associates. In this episode, she draws on insights from completing over 500 senior financial officer and board searches to offer a practical roadmap for executives aspiring to the C-suite. She talks about what boards are really looking for, why CFOs often become CEOs, and how to build the right narrative around your career. Jenna also shares key lessons from her book To the Top, including how to position yourself for succession, communicate your leadership potential, and align with the right opportunities at the right time. Whether you’re a rising finance leader or any executive planning a strategic career move, this conversation is a blueprint for owning your journey to the top.
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.