One of the assumptions people often make about my role as a Managing Partner at Rallyday is that building trust with portfolio company CEOs must come naturally. After all, I spent most of my career as a CEO myself. I have lived through the challenges of growing a company, leading teams, making payroll, navigating uncertainty, and carrying the weight that comes with being responsible for an entire organization.
That experience helps. It gives me empathy. It gives me perspective. It gives me a real appreciation for how lonely leadership can be.
But I have learned that trust is never automatic.
In private equity, trust does not come from a title, a board seat, or a résumé. It does not materialize because someone has operating experience or because an investor says they are founder-friendly. Rallyday was built by founders, for founders, with a purpose of empowering leaders to go even bigger and creating the most value for the most people through multiple forms of capital, not just financial capital. I believe in that deeply. But even then, those words only matter if a CEO actually feels them in the relationship.
And that takes time. It takes consistency. It takes real connection.
Many CEOs enter a private equity partnership during one of the most significant transitions of their professional lives. For the first time in years, and sometimes for the first time ever, they are no longer in full control of the business they built or have poured themselves into leading. They are now expected to work alongside new stakeholders who bring opinions, expectations, questions, and ideas. Even when the partnership is positive, it can still feel unfamiliar. Add in all the stereotypes that surround private equity, and it is not hard to understand why some CEOs begin cautiously.
At the same time, these leaders are usually highly confident in their understanding of the business, and rightly so. They know the customers, the employees, the market dynamics, and the company’s history better than anyone else. They have context no spreadsheet can fully capture. They have instincts shaped by years of hard decisions, missed sleep, and lessons learned the hard way. So when an outside partner arrives, even a well-intentioned one, the natural question is not, “What can I learn from you?” It is often, “Do you really understand what I am carrying?”
That is why I have come to believe that trust is not built first through credentials. It is built through connection.
The first step, for me, is understanding what matters most to the CEO.
Every leader has priorities that extend well beyond the quarterly board deck. Some care most deeply about culture and protecting what makes their company special. Some are relentlessly focused on serving customers at the highest level. Some are motivated by creating opportunity for employees and building a place where people can grow. Others are driven by innovation, by solving hard problems, or by fulfilling a personal vision they have carried for years.
If I want to be useful, I need to understand those motivations before I start offering advice.
That means listening before advising. Asking before assuming. Spending time understanding not just what the CEO is trying to do, but why it matters so much to them. In my experience, that is where the relationship begins to shift. When a CEO believes you genuinely care about what they care about, the conversation becomes more open. The candor increases. The defensiveness drops. The partnership starts to feel real.
This does not mean we avoid hard conversations. Quite the opposite. Trust is what makes hard conversations productive.
When trust is present, a CEO knows that challenge is coming from a good place. They know questions are meant to sharpen thinking, not undermine authority. They know disagreement is in service of a better outcome, not a power struggle. Without trust, even good advice can feel intrusive. With trust, even difficult feedback can feel supportive.
The second way trust gets built is by helping CEOs and their leadership teams become even better at what they do.
This is where I believe private equity can create its greatest value.
I do not view my role as having all the answers. I view my role as being a thought partner. Sometimes that means sharing lessons from my own journey as a founder and CEO. Sometimes it means offering pattern recognition from having seen similar moments across companies and industries. Sometimes it means connecting leaders to the right resource, advisor, or peer. Sometimes it means simply asking the question that helps the team see the issue more clearly.
The point is not to take over the steering wheel. The point is to help great leaders become even stronger leaders.
That distinction matters. CEOs do not need investors who are eager to prove how much they know. They need partners who can add value in a way that is practical, respectful, and aligned with the leader in the seat. At Rallyday, we talk a lot about bringing experiential, creative, and human capital alongside financial capital. In my mind, trust is what allows all of that to land. Without trust, even good support can feel like interference. With trust, support becomes leverage.
I have also learned that trust is built in the small moments, not just the big ones.
It is built when you follow through on what you say you will do. It is built when you show up prepared. It is built when you protect confidentiality. It is built when you give credit freely. It is built when you are honest about what you know and equally honest about what you do not know. It is built when a CEO feels that you are for them, not just evaluating them.
Those things sound simple. But in practice, they are everything.
Over time, I have learned, sometimes the hard way, that trust between a Managing Partner and a CEO is built much like any meaningful relationship. It requires patience. It requires humility. It requires consistency. It requires earning the right to be heard, not assuming it comes with the role.
My own background helps me empathize. Having built and led a company myself, and having served as a private equity-backed CEO, I understand the complexity of the seat in a way that is difficult to learn from a distance alone. But empathy alone is not enough. Trust is earned through actions, through repetition, and through a genuine commitment to helping another leader succeed.
At its best, the relationship between a private equity investor and a CEO is not one of oversight. It is one of partnership. Not performative partnership. Real partnership. The kind where both sides are aligned around building something exceptional. The kind where truth can be spoken candidly. The kind where ambition gets bigger because trust makes it safe to go there.
And when that kind of trust exists, extraordinary things can and do happen.
