Building Community and Connection as a Founder: Don’t Try to Go It Alone

Part 2: Building Community and Connection as a Founder: Don’t Try to Go It Alone
by Tom Wallace

Many people say, “It’s lonely at the top,” but does it have to be? Isolation is harmful to any founder’s well-being and mental health, and fortunately, it’s within our control to avoid it. Choosing to go it alone is just that—a choice. Instead, we can surround ourselves with supportive individuals who also challenge us. There are many ways to foster a sense of community and connection as a founder, all of which are good for our mental health, increase our chances of success, and make the journey more enjoyable.

My journey as a founder began at the age of twenty-three, and it was somewhat unique in that I started my first company with my best friend. Many people advised us against this, warning that it was a bad idea and predicting we would end up hating each other. That was four decades and four companies ago. He is still my best friend, and we are still in business together today. Having a business partner you can trust, share both the good and bad times with, who will tell you when you’re being a jerk, and who always has your back makes building a company from scratch a little easier and, in my experience, far more enjoyable and rewarding.

Create a Culture of Ownership

It’s often said that “entrepreneurship is a team sport,” and I wholeheartedly agree. A founder’s success is directly tied to the quality of their team, especially their management team—the individuals closest to them on their journey. Even without co-founders or official partners, you can build a team that thinks and acts like founders. Creating a culture of ownership among the management team is crucial for any founder’s success. This requires concerted effort, and it goes without saying that sharing equity can go a long way in enhancing a sense of ownership. When done right, the rewards are immense. Treat people like co-founders, and they will act like founders; they will work harder, be more loyal, and share the burden when times get tough.

Value Your Team’s Success as Much as Your Own

Once I came to the profound realization that my team not only recognized but deeply valued my care and dedication towards their success—equivalent to my own—the dynamics of our collaboration shifted. This understanding facilitated smoother operations and fostered a sense of unity and mutual respect within the team. Furthermore, deliberately acknowledging and giving credit to others whenever possible was transformative. It boosted morale and instilled a profound sense of belonging and significance. By making each team member feel valued and integral to our collective success, we forged a culture where everyone felt invested in something truly extraordinary.

Be a Strong Leader vs. the “Perfect” Manager

Being a CEO at twenty-three, I made countless mistakes. I wasn’t the fastest learner and often had to make the same mistake more than once before learning the lesson. The most important lesson I learned was understanding what authentic leadership entails. I initially believed leadership meant getting people to follow me by always working harder than everyone else, having the right answers most of the time, being the best closer, being an uber-manager, and never letting my guard down or appearing vulnerable.

Over time, I realized these perceptions were ego-driven and not the true path to effective leadership. I mistakenly thought that as the founder and CEO, I had to be almost superhuman. The unnecessary pressure I put on myself was detrimental to my mental health and my team’s well-being. Eventually, I came to understand that I didn’t need to be a perfect manager and that management really wasn’t even my thing. What mattered was being a strong leader, and that was something I could do.

Understanding that leadership isn’t about being a superhero but instead being open about my shortcomings and mistakes earned me respect from my team. Owning up to my mistakes publicly and sharing them with my team gave them the confidence to take risks and make their own mistakes, leading to a surge in innovation. Recognizing that my ego should never dictate important decisions but rather learning to trust my heart and intuition allowed me to evolve into a leader others wanted to be around and were also happy to follow.

Join a CEO Peer Group for Strategic and Emotional Benefits

Early in my career, one of my best decisions was to join a CEO peer group, a concept that was less common in my early days than it is today. Once a month, a small group of us would convene to discuss our challenges, share our problems, and seek advice and counsel from one another. These CEO mastermind groups proved invaluable throughout my career, offering me and my fellow founders a sense of camaraderie and support in navigating the complexities of building and scaling a company.

To an outsider, our monthly CEO meetings might have seemed like group therapy, and in many ways, they were. These groups benefited me in numerous ways. Not only did I forge lifelong friendships, but I also gleaned invaluable insights from my fellow CEOs. I discovered that many of my challenges were not unique, and my peers could relate to them and offer excellent advice on overcoming them. I highly recommend that any founder seek out and join one of these groups. The time invested will be far outweighed by the strategic and emotional benefits gained.

Leave Behind the Fear-based Mindset

One of the primary motivators for many of us founders is fear. For me, it was primarily the fear of failure. The thought of having to admit to my parents, siblings, and friends that I had failed, that my company hadn’t succeeded, was terrifying to me. The fear of proving the naysayers right was also a powerful driving force. I was determined to prove to the world that I could succeed against the odds. Over the years, I lost countless nights of sleep worrying about losing customers, failing to secure important deals, or the possibility of key team members leaving. Operating from this fear-based mindset took a toll on my mental health and wasn’t at all conducive to success.

Eventually, I realized that focusing so much on fear was detrimental to my well-being and counterproductive. The law of attraction suggests that what we focus on, we attract. I was focusing on fear far too much. I made a conscious decision to change this narrative. I asked myself, “What if I were fearless?” I rejected Andy Grove’s “Only the Paranoid Survive” mentality and embraced a different approach – I would be fearless.

I began to shift my perspective and made a commitment to myself: I wouldn’t waste my time and energy worrying about what I didn’t have or what could go wrong next. Instead, I chose to focus on what I did have. Shifting to a fearless mindset was liberating and empowering. It made me excited about the possibilities, about what might happen if we took risks and weren’t afraid to fail, if we, as a team, were goddamn fearless! I often used to ask myself, “What’s the worst thing that could happen?” and realized I could live with it, whatever that was. It might hurt like hell, but it wouldn’t kill us. Fortune favors the bold!

Embrace the Struggle on the Less Traveled Road

I also started to embrace the journey of an entrepreneur – the struggles and successes, the highs and the lows. I was truly grateful and appreciated the opportunity before my team and I. As Robert Frost famously wrote, “Two roads diverged in a wood, and I – I took the one less traveled by, and that has made all the difference.” I reminded myself that this is precisely what I signed up for; I deliberately chose the less traveled path—the path every founder takes, fully aware that it’s the fucking brutally hard road. I willingly accepted that adversity would lurk around every corner, and the odds were stacked against me and my team.

I began to see setbacks in a different light, considering that perhaps they were meant to be. Maybe, just maybe, the universe was trying to communicate something to us—like we didn’t really need that particular customer, or the target market we were pursuing wasn’t the right fit, and we should explore other avenues. I learned that dwelling on what happened isn’t as crucial as how my team and I responded, not reacted. Blaming someone for the situation wasn’t productive; focusing on where we go from here and how we can address and fix the problem was far more critical.

Being a Founder is Creating Something Out of Nothing

Building a company from scratch is incredibly challenging. Ryan Nece, a former NFL player who won a Super Bowl and afterward became an entrepreneur, once told me that building a business is much more challenging than playing football at the highest level in the NFL! While each of us founders has a unique journey, we all share common battle scars earned from creating something out of nothing. The journey ahead will be difficult, so my advice is simple: don’t go alone. For your own well-being and mental health, it’s crucial to share both the tough times and the victories with others.

I still frequently remind myself that there’s nothing else I’d rather be doing and nowhere else I’d rather be. The results can be remarkable when a founder fosters a company culture where every team member feels like an owner, like a true partner. My passion lies in assembling an exceptional team, setting crazy goals, and relentlessly working together to achieve them. And that’s precisely what I’m doing. I would tell myself I’m not just suited for this; I was made for it.

Personally, I’ve experienced more success than I perhaps deserve. Was luck involved? Undoubtedly. But there was also a great deal of hard work, perseverance, strategic planning, and teamwork. When you surround yourself with partners, other founders and advisors, and trusted team members, it’s never lonely at the top – because you’re not alone.

Related Stories


Subscribe to the Florida Funders Newsletter to stay close to what we're building.