Back in 2019, I was convinced that I had finally reached the peak of my career. Summited my professional Mt. Everest, if you will. I had just completed the sale of YourCause to Blackbaud for more than $150 million, generated what was considered an impressive return for my investors, created liquidity for shareholders and employees alike, and within a decade had conceptualized, developed, launched, operated, and sold my business.
And no, this writing is not about how "unfulfilled" I felt afterward, or how I learned that "money doesn't buy happiness," or any of the other themes so commonly associated with moments like that. While those ideas may absolutely hold truth, and I could likely write an entire piece supporting each of them, I instead wanted to focus on a few things that surprised me, each of which ultimately played a significant role in bringing me back, full steam ahead, to doing what I love.
I was prompted to compile my thoughts because of the continual stream of questions that have come my way over the past several months asking things like, "Why are you getting back into the space?" or, in some cases, "Welcome back. The space really needs you."
So before jumping into the core insights that inspired me to write this post, let me first define both "the space" and "welcome back," as they help frame much of what I am about to share.
The other day, someone from my team mentioned that they had recently read one of my posts. I asked what they thought, and they responded, "To be honest, I skimmed it until I hit the bullet points." Fair feedback. They went on to explain how much easier bullet points are to digest than larger blocks of text like the ones above. So with that, I'll move directly into some of the key lessons and insights I have taken away throughout my journey back into the space, all of which I'll try to present in a slightly more 'skimmable' format. :)
Passion Is Everything
I loved what I was building at Tentacle, the company I founded after YourCause and before momoGood. Let's put aside for a moment the fact that we were essentially trying to outbuild Vanta on what felt like a comparatively shoestring budget. We were solving a very real information security problem, one that I had personally dealt with for years at YourCause and one that remains highly relevant today.
On paper, it checked all the boxes. I was once again building from scratch: product, technology, team, go-to-market strategy, all of it. In many ways, it was exactly the type of challenge entrepreneurs are supposed to love. Yet throughout those five years that I was building Tentacle, every time I received a non-Tentacle related phone call (most often connected to the CSR space), I found myself immediately clearing my calendar and genuinely excited to engage.
I loved revisiting the old YourCause playbook, making introductions across the industry, discussing "do good" strategies, and connecting with people who were truly trying to create meaningful change in the world. It did not take long for me to realize something important: I was becoming more energized by conversations about what I used to do than by conversations about what I was currently doing. My passion had never really left.
Passion truly is everything. It is what pushes you to go the extra mile for the people you serve. It is what keeps your mind turning late at night about how to improve, innovate, and solve bigger problems. It is what attracts talented people who want to build alongside you. Passion is the ingredient that transforms something from simply "good" into something memorable. And for me, realizing where my passion still lived became one of the clearest signals that it was time to come back, this time through momoGood.
Can't Just NOT Do Something About It
I have always been the type of person who pulls over to help someone change a tire. If I am being honest, there is something exciting about those moments for me. Whether it is wanting to play hero ball or simply proving to myself that I still know how to change a tire, I have always found it difficult to sit on the sidelines and watch a problem go unsolved, especially when I believe I have the ability to help.
And therein lies the second reason I decided to jump back into "the space." Over the years, as I mentioned earlier, I have watched the world of CSR and employee engagement from the sidelines. Admittedly, I did not have the same court-side view I once had, and I certainly was not an active player on the court, but I maintained enough visibility to recognize the slowing pace of innovation and the general lack of meaningful progress during my time away. In many ways, it made sense.
Most of the founders who carried real passion and conviction for the space had exited it, myself included. In doing so, many of the voices pushing for change, advocating for impact, and challenging the status quo slowly faded away. And much like seeing someone stranded on the side of the road with a flat tire, I eventually realized I could not just sit there and do nothing about it anymore. The best way I knew how to contribute was to jump headfirst back into it and, in many ways, pick up where I left off.
Feeling Valued Is Real
I am sure this is partially a result of getting older and accumulating a much wider range of life experiences, but jumping back into the space was heavily influenced by something I had not fully realized before: my desire to feel valued. I never really viewed myself as someone who actively seeks attention, recognition, or center stage, all things I previously associated with "feeling valued." My perspective on that has changed over time.
After leaving the space and stepping away from an industry where I had experienced a great deal of success, I slowly realized over those five years just how much I valued the feeling that the work we were doing actually mattered. That the work was appreciated. That it was making a difference. Without fully realizing it at the time, feeling valued for the work we were doing for nonprofits, CSR programs, employees, and communities became one of the biggest reasons I gave everything I had, day in and day out. That realization has since become a very important factor in how I make major decisions in my life, including this next chapter of my career.
I think much of that sense of value came from the influence and positive disruption we were creating within the space. It came from being one of the few groups genuinely asking how we could do more good for more people, in more communities, across more parts of the world. It came from collaborating with our customers to expand impact and from earning the trust of billion-dollar and trillion-dollar companies to help drive positive change within their communities. That sense of purpose and value is incredibly difficult to replicate elsewhere. And when you experience it long enough, you realize just how real it truly is.
Age Welcomes New Challenges
As we began putting momoGood together, we were pretty dead set on making this, for me, startup number four. The fourth pure startup journey. The fourth time taking an idea, building the technology, bringing it to market, and trying to scale it into a meaningful business. And right as we were about to press "go," we received a call from Edison Partners asking whether we would consider an alternative route. A very different type of challenge.
Instead of pursuing a pure build strategy, would we consider a build-plus-acquire model? The opportunity to partner with Kelly Ford, Vinny Olmstead, and others was incredibly compelling. It gave us the opportunity to acquire meaningful functionality, texting, ticketing, events, auctions, and more, while simultaneously gaining a strong customer base, recurring revenue, and an established team to build from. At the same time, it introduced a completely new set of challenges that I had never encountered before. There were uncertainties, complexities, and strategic dynamics that simply did not exist within the startup playbook I had become accustomed to over the previous 20+ years.
Partnering with private equity, versus building entirely on my own, was always going to be a dramatically different experience than what I had grown comfortable with throughout my career. As you can probably tell, I ultimately chose the private equity partner route. And while I spent a great deal of time thinking through the decision, it ultimately came down to the challenge itself. The challenge of pursuing momoGood through a build-and-acquire strategy felt entirely new to me, and I found myself increasingly drawn toward the idea of stepping into something unfamiliar.
It presented an opportunity to gain experiences and develop skills that I may never otherwise have had the chance to pursue. Over weeks of deliberation, I realized something interesting: as entrepreneurs get older, many of us begin to value and actively seek out entirely new challenges. And that is exactly what I have found in this chapter with momoGood.
If you are reading one of my posts for the first time, you might be asking yourself, "Why on earth does this guy do this?" Honestly, I would not blame you. I do not have a massive readership, and these posts certainly are not generating business for us. The process has become incredibly therapeutic for me. It gives me an opportunity to reflect on the people in my life, the experiences that shape me, and the moments that influence how I think, why I lead the way I do, and ultimately the decisions I make.
As always, I would genuinely love to hear your thoughts, perspectives, or feedback on this topic, or any others. And if you are simply looking for someone to talk to, I am always happy to be an ear to bend. Just reach out.
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