Becoming a CEO

What does it really mean to become a CEO? For Matt Blumberg, multi-time CEO, founder, author, and board member, the answer isn’t about titles or authority, it’s about responsibility.  Matt explains that the CEO carries the weight of the entire company, navigating the highest highs and lowest lows, often at the same time. Drawing on decades of experience scaling companies, leading through crises, a...

Why do so many succession plans fail? For Jay Hummel, Co-Founder of Wealth Advisor Growth Network, the answer is rarely about numbers - it’s about leadership. Jay believes leadership is about intentionality: preparing for succession well before it’s needed, building cultures defined by accountability, and having the courage to make decisions when others stall. He also unpacks why emotions often de...

What does it take to grow from hustling founder to seasoned CEO? For Eytan Wiener, co-founder of Quantum Networks and former CEO of GETIDA, the answer is grit, agility, and relationships. Eytan’s leadership journey wasn’t learned from theory. It was built through trial, error, and relentless persistence. From learning the hard way that money isn’t the ultimate motivator, to realizing that business...

What separates good CEOs from great ones? For Adam Enbar, co-founder and former CEO of Flatiron School, the answer is simple: it all comes down to people. Adam’s leadership philosophy is built on two principles: hire people who are better than you, and then trust them to do their work. He believes recruiting is the most important job of a CEO - more important than strategy, operations, or fundrais...

What does it really mean to lead at the highest level? For David Siegel, former CEO of Investopedia and Meetup, leadership isn’t about titles or power. It’s about culture, kindness, and carrying the weight of decisions no one else wants to make. In his time leading companies like Meetup and Investopedia, David learned that leadership is less about strategy and more about people. His philosophy - b...