5 CEOs Get Brutally Honest About Leadership in Today’s World

There’s a unique energy that exists when you put five CEOs around one table. At our latest The CEO Roundtable episode, that dynamic played out in full. I sat down with Danny Wirtz (Chicago Blackhawks, Breakthru Beverage), Ashley Thompson (MUSH), Gregg Majewski (Craveworthy Brands), Emily Groden (Evergreen) and Luke Saunders (Farmer’s Fridge) to explore what it actually means to be a CEO in today’s world. It was an open, candid exchange of hard-won lessons, gut decisions and the kind of self-reflection that only comes from leading through highs and lows.

One of the big takeaways from this discussion was the emotional rollercoaster of entrepreneurship and leadership. Nearly everyone at the table shared stories about the personal weight of leading a company. Emily spoke about how lonely it can feel at the top, and Danny emphasized that when you’re in the driver’s seat, there’s nowhere to hide, specifically when you’re the CEO of a professional sports team. Gregg put it simply: “It’s not sexy.” These weren’t just war stories — they were reminders that leadership comes with a cost, one that can’t be measured in valuations or press headlines.

Related: 5 Founder-CEOs Come Together to Discuss the Realities of Leadership, Entrepreneurship and What It Takes to Succeed

Another powerful theme was letting go — or at least, learning to. Each of these leaders started their company or took over a legacy one with a clear vision, but as their businesses grew, so did the need to trust others to execute. Luke talked about the complexity of scaling Farmer’s Fridge and the moment he realized he couldn’t do everything himself. That same sentiment echoed across the table. Ashley, now with a larger team and investment behind MUSH, spoke about balancing hands-on energy with leadership maturity. Growth, it turns out, means giving up control to gain momentum.

We also dug into the unique pressures of consumer-facing businesses. All five leaders are selling something you can touch, taste or experience — products that depend on branding, shelf space and customer emotion. Whether it’s the nostalgia of Evergreen waffles or the boldness of Craveworthy’s restaurant portfolio, these founders are shaping what Americans eat and how they feel about it. That means rapid feedback loops, tight margins and constant adaptation. No one at the table is insulated from inflation, supply chain pain or labor shortages, but each of them is trying to build resilience into their operations.

One thing I didn’t expect — but probably should have — was how deeply personal the conversation got. Gregg described feeling almost addicted to the chaos of startup life. Ashley shared how imposter syndrome creeps in, even after massive success. Danny talked about inheriting not just a brand, but a legacy. And Luke reminded us that startup culture isn’t always the mental health haven people think it is. There was vulnerability in the room, and it made the dialogue more honest — and frankly, more useful — for anyone trying to understand modern leadership.

Related: How the CEO of This Iconic Pizza Brand Is Building on 50 Years of Deep-Dish Dominance and Fueling Sustainable Growth

As the moderator, my goal wasn’t to extract soundbites. It was to give space for complexity. This wasn’t a panel of untouchable icons. These are people navigating real-time decisions in messy, evolving markets. The biggest lesson? Being a CEO today means knowing yourself just as well as you know your P&L. Also, when you’re the CEO of a large organization, you have a heavy responsibility to lead with integrity, to serve your employees and customers and to utilize business “for good.” Otherwise, what are we doing here?!