Five Years In: The Story of Cloud Nine and What Comes Next

Five years ago, I was approaching my 40th birthday and found myself asking some bigger questions: What’s next? What am I meant to do? Where can I make the greatest impact?

As I recently joked on the “Coffee with Cagnetta” podcast, I decided I was either going to have a third baby or start a business.

Well, the third baby didn’t happen. Cloud Nine did.

But the truth is, Cloud Nine’s story started long before 2021.

Looking back, there have always been two parts of me that seemed destined to come together: entrepreneurship and service. I was the kid who loved selling Girl Scout cookies and setting up lemonade stands. I went to business school and loved the entrepreneurial side of business. At the same time, I was raised by parents who taught me that giving back wasn’t something you did occasionally. It was simply part of life.

So when I entered the nonprofit sector, I never saw business and mission as opposites. I became fascinated by what could happen when you brought an entrepreneurial mindset into organizations working every day to strengthen communities.

That idea followed me through nearly two decades of nonprofit work. Eventually, it became Cloud Nine.

Two Jessicas and an Idea

In 2021, I co-founded Cloud Nine Nonprofit Advisors with Jessica Munday, a close friend, mentor and talented entrepreneur who remains an important part of this company’s story.

I still love the way we described the idea back then: What if we put our superpowers together?

We had different strengths and experiences, but we shared a belief that we could build something meaningful for our families while giving nonprofits the kind of strategic support we knew they needed.

So, we jumped.

There was no perfect roadmap. There were two Jessicas with an idea, a lot of energy and a willingness to figure things out as we went. We were finding clients while serving clients, building processes while doing the work and learning in real time what Cloud Nine could become.

Those early clients took a chance on a young firm and trusted us with something incredibly important: their missions. Over time, the idea became a company. We welcomed clients, expanded our services and built a team of people who believed in the work as much as we did.

Our mission became simple: Help nonprofits transcend the challenges they face.

This year marked a significant transition as I became the sole owner of Cloud Nine. Our paths as business partners have changed, but my gratitude for what Jessica and I built together has not. Her strengths, vision and entrepreneurial spirit are woven into the foundation of this company, and her fingerprints will always be part of its story.

What Building Cloud Nine Taught Me

The first five years were not only about building a business. They changed me as a leader.

One of the most defining periods came early in Cloud Nine’s story when I lost my dad suddenly in 2022. Anyone who has experienced grief knows it doesn’t politely wait until your calendar clears.

I was a new entrepreneur. Clients were counting on us. I was a wife and a mom. And suddenly, I was also trying to navigate a world without my dad in it.

My response was to push.

I worked harder, stayed busy and poured myself into growing Cloud Nine. For a while, I think I wore some of that intensity as a badge of honor. That’s what entrepreneurs do, right? We hustle. We grind. We figure it out.

Except I’ve learned that isn’t the whole story.

I haven’t lost my ambition. If anything, I’m more excited about what is possible for Cloud Nine than I have ever been. But I no longer believe building a great company is measured by how exhausted I am at the end of the week.

I’ve learned to trust my team, create space, be present with my family and protect the things that bring me joy. I’ve learned that saying “not right now” can sometimes be just as important as saying “yes.”

Those lessons have also shaped the kind of company I want Cloud Nine to be.

From early on, we made a conscious decision that Cloud Nine wouldn’t simply be a collection of contractors. We wanted to build a place where talented people could create careers, grow professionally and still have full lives outside of work.

Because you don’t build a great company by burning out great people, including yourself.

That is also why one of our values, Bringing Joy in All We Do, means more to me today than it did five years ago. The nonprofit leaders we work alongside carry enormous responsibility, and when Cloud Nine enters the room, I want us to bring expertise, strategy, accountability and ideas. But I also want us to bring energy, possibility and a sense that the work can feel lighter without ever losing sight of how much it matters.

Joy isn’t the absence of hard things. It’s something we choose to bring with us through them.

What Comes Next

Five years later, I find myself asking some of the same questions I asked at 40: What’s next? What are we meant to build? Where can we make the greatest impact?

I’ve started calling the answer Cloud Nine 2.0.

This next chapter isn’t about changing everything that got us here. It is about taking what we have learned and becoming much more intentional about where we are going.

Artificial intelligence will certainly be part of that future, but we are trying not to start with the tools. The tools will change. Instead, we are starting with the problem: What challenge are we trying to solve? And if technology gives us time back, what are we going to do with that time?

For us, the answer is more time listening to our clients, more time thinking and strategizing and more time asking better questions. It means more time helping nonprofit leaders work through the challenges that keep them awake at night and less time letting inboxes, meetings and administrative work dictate the day.

In other words, more time doing the deeply human work that brought us here in the first place.

And when I think about what I want Cloud Nine to look like at 10 years old, of course growth matters. Revenue matters. A healthy business allows us to invest in our people, innovate and serve more organizations.

But the measure that matters most to me is impact: how many nonprofits are stronger because we were beside them, how many leaders feel better equipped to lead and how many communities are stronger because those organizations are thriving.

That is our North Star.

At 40, I thought I was starting a business. Five years later, I realize I was continuing a journey I had already been on most of my life: finding the intersection between entrepreneurship, service and purpose.

I am deeply grateful to Jessica, our team, our clients, our families and every person who believed in Cloud Nine before there was much of a track record to believe in. Five years in, the why is clearer than ever. Thriving communities need thriving nonprofits, and I want Cloud Nine to keep becoming the kind of partner those organizations deserve.

That’s what I’m carrying into the next five.