My Journey to Becoming a CEO: Lessons Learned Along the Way

From Barista to Business Leader: My Journey to Leadership

Before I became the COO and eventually the CEO of a multi-million-dollar, bootstrapped business, I lived many lives. I transitioned from being a barista to a bookkeeper. I studied film and theatre, then ran a high-end jewelry store. I never had a clear plan for my life, much less an MBA. But by the age of 25, I had nearly a decade of management and training experience. This experience was earned not through theory but through my proximity to people, systems, and responsibilities.

In the wake of the 2008 crash, I moved from San Francisco to New York City with a simple question:

Could I make it there?

Within two weeks, I found a well-paying job in marketing and customer service. This role provided me with a front-row seat to leadership lessons in all their forms: the good, the bad, and the deeply instructive.

Taking a Leap of Faith

After almost two years of feeling like I was trading parts of myself for a paycheck, I made another leap into uncertainty. I joined forces with two founders whose early-stage startup aligned deeply with my values. For $10 an hour, I became their office manager, working out of a home office. Little did I know, I had just committed to what would become 11.5 of the most fulfilling, exhausting, growth-demanding, and meaningful years of my life.

We built the proverbial plane while flying it.

I co-led the team with one of the founders, who became my business partner for nearly eight years. Together, we navigated a self-funded buyout of the third founder. We stayed ahead of ruthless competition and worked with an exceptional executive coach. This coach helped us think beyond survival and into sustainability. We built one of the healthiest and most genuinely supportive workplace cultures I’ve ever experienced. Against the odds, we beat the statistic that less than 5% of all businesses make it to $1M in annual revenue, and we kept growing beyond that. The biggest takeaway was that I learned a lot, and quickly.

Reflecting on My Journey

When I reflect on this time in my life, the answer to my initial question seems clear:

Yes, I've made it.

Champagne popped, and story over. But the reality was that along the journey, imposter syndrome was a constant companion. I burned out more than once. I made countless mistakes. Despite leading a team of nearly 200 people at our peak, I also experienced profound and unexpected loneliness alongside our success. So, it didn't always feel that way.

I stepped into the CEO role prior to our first acquisition and later stayed on as VP of Business Development to formally build our B2B arm. After our second acquisition, I looked at the gray hairs earned through keeping everything “up and to the right.” I found myself asking a quieter, more essential question:

What now? I can’t have gone through all of this just to get us here...

And then, I started hearing the answer: I wanted to pay it forward.

Embracing Coaching

Within a year, I earned my coaching credential through the International Coaching Federation. I began coaching leaders through my independent practice. The intensive coaching training, combined with my lived experience, allowed me to walk alongside founders. I provided guidance so they could hopefully make fewer mistakes and avoid acquiring so many gray hairs along the way. Soon after my credentialing, kismet intervened and connected me with Mochary Method, a boutique coaching firm specializing in CEOs of rapidly scaling startups. I said yes to what felt like a natural continuation of my path.

Now, after more than three years and over 3,000 hours coaching founders and leaders, I remain deeply energized by this work. I am continually inspired by the leaders I partner with, their courage, their vision, and their willingness to grow. Supporting them in accessing their own clarity, strengthening their teams, and amplifying their impact for good feels less like a career choice and more like the culmination of everything that came before.

The Work I Was Shaped For

This is the work I was shaped for: slowly, imperfectly, and with purpose. I’ve learned that every experience, every challenge, and every success has led me to this moment. It’s about more than just business; it’s about connection, growth, and the journey we all share.

The Importance of Connection

Connection is vital in both personal and professional realms. As I reflect on my journey, I realize how essential it is to build relationships. These connections foster collaboration and innovation. They help us navigate challenges and celebrate successes together.

When we connect with others, we create a support system. This network can provide encouragement during tough times and celebrate our achievements. I encourage you to nurture these connections. Reach out to someone you admire or someone who inspires you. You never know where that conversation might lead.

Lessons Learned Along the Way

Throughout my career, I’ve learned valuable lessons that I want to share. First, embrace vulnerability. It’s okay to admit when you don’t have all the answers. This openness fosters trust and encourages others to share their thoughts and ideas.

Second, prioritize self-care. Burnout can sneak up on you, especially in high-pressure environments. Make time for yourself. Whether it’s a walk in nature or a few quiet moments with a book, find what rejuvenates you.

Lastly, always be open to learning. The world is constantly changing, and so should we. Seek out new experiences, attend workshops, and engage with mentors. This mindset will keep you adaptable and ready for whatever comes next.

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