Before we dive in, we have some exciting news—Opening the C-Suite is now Momentum Mode. Same podcast, same raw and real conversations, but with a sharper focus: how leaders build, sustain, and accelerate momentum in business. If you’re a founder, operator, executive, or investor navigating high-stakes decisions, Momentum Mode is here to help you push forward. And today, we’re talking about how CEO’s and interns alike can push through some of the biggest challenges today.
One of the biggest surprises for first-time CEOs isn’t the weight of decision-making, the pressure of quarterly results, or even the endless demands on their time. It’s the loneliness.
In our recent conversation with Dan Dal Degan—known to many as Triple D—this theme came up early and often. Dan, a seasoned SaaS executive, investor, and board member, has seen it all. He’s led companies through high-stakes acquisitions, scaled sales teams, and even been personally thanked by Marc Benioff in his autobiography for his contributions to Salesforce. But despite his deep expertise in growth and execution, his most impactful insights were about the human side of leadership.
The CEO’s Reality: Alone at the Top
Dan put it plainly:
“The first thing I realized as a CEO—after you get past the pomp and circumstance of the title—is that it's a lonely job. You can’t turn to your team with your biggest doubts, and you can’t always be fully transparent with your board. You’re expected to have the answers, but no one tells you how isolating that can feel.”
Many leaders assume that once they reach the top, they’ll finally have the autonomy to make decisions as they see fit. But the reality is different. As Dan explained:
“You get that mantle of responsibility, and you realize—oh sh*t—it’s now on me. The weight of every decision feels different when you’re the one accountable for it.”
The pressure to project confidence while navigating uncertainty is immense. CEOs often have no one they can confide in about their doubts or fears without risking perception issues from their board, investors, or team. And in a remote or hybrid world, this isolation has only deepened.
Finding a Safe Harbor: Why Every CEO Needs a Confidant
Dan’s approach to overcoming this challenge is simple but powerful: CEOs need a confidant. Someone outside their direct reporting structure who understands the pressures of the role but isn’t evaluating their performance.
“A lot of CEOs don’t have anybody on their board or in their network they can go to for those kinds of conversations. And that’s a problem. If you don’t have a safe space to process your fears and uncertainties, they just fester. I try to be that person for the CEOs I work with.”
That’s why Dan makes it a priority to be that person for the CEOs he mentors. As an independent board member—not tied to a specific investor—he provides support without ulterior motives.
“I make it clear from the beginning that success for me is not just a great financial outcome, but also ensuring that the CEO thrives and grows. Their career, their well-being—it all matters.”
Mentorship is Dying—And That’s a Problem
One of Dan’s more striking observations was how mentorship has fundamentally changed.
“Mentoring is dead. At least, the kind of mentoring that shaped so many of us. The spontaneous, unscheduled, informal conversations that happened in hallways, over lunch, or at the bar after work—that’s disappearing in a remote world.”
The shift to remote work has made those spontaneous interactions rare, leaving younger professionals without the same informal learning opportunities previous generations had.
So what’s the solution?
Companies must intentionally design mentorship. “It has to be programmatic,” Dan emphasized. That means structured mentorship initiatives, pairing experienced leaders with emerging talent, and finding ways to recreate the serendipitous learning moments that used to happen naturally.
Time is Your Most Valuable Asset—Treat It Like One
A major theme in our conversation was time—not just how CEOs manage it, but how they value it.
“Compared to money, time—you don’t know your balance. You can make more money. You can even get money back. But time? You can’t make more of it, and you don’t know how much you have left.”
That realization forces great leaders to be intentional about where they focus their energy. But it also means that when they give someone their attention, they need to be fully present. One of Dan’s mentors once told him:
“If you’re here, then BE here. Don’t check your phone, don’t think about the next meeting—just be present.”
For leaders, that means putting down the phone, making eye contact, and demonstrating to their teams that they genuinely care.
The Rhythm of Leadership: Why Every CEO Needs a Band
Beyond the boardroom, Dan is also a musician—something that’s deeply intertwined with his leadership philosophy. He believes that music, much like business, requires collaboration, adaptability, and an understanding of how different roles come together to create something greater than the sum of its parts.
“Every company should have a band. Music brings people together in ways that corporate initiatives never could. When you play music with people, you learn about them in a different way. And that kind of connection is what great teams are built on.”
In a world where remote work has eroded many traditional ways of bonding, leaders must find creative ways to build culture. Whether that’s through music, shared experiences, or intentional mentorship, the key is to foster human connection.
“Playing in a band forces you to listen, to adjust, and to find harmony with the people around you. That’s exactly what great leaders do in business. You can’t just play louder than everyone else—you have to create space for others and make sure the whole team is in sync.”
Dan’s passion for music also translates into how he approaches leadership development. He encourages executives to find creative outlets outside of work—whether it’s music, sports, or another passion—because those experiences help build resilience, problem-solving skills, and emotional intelligence.
“Great leadership isn’t just about numbers and strategy. It’s about connection, creativity, and knowing how to bring out the best in others. Music has taught me that, and I bring those lessons into every company I work with.”
Final Thoughts
The biggest takeaway from my conversation with Dan? Leadership isn’t just about vision and execution—it’s about relationships, trust, and human connection. The best CEOs understand that their role isn’t just about strategy; it’s about creating an environment where people thrive.
And sometimes, that starts with picking up a guitar.
What strategies have helped you combat the isolation of leadership? We’d love to hear your thoughts in the comments.
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