The Truth About Entrepreneurship: It’s Lonely as Hell, and I’d Do It Again
The Loneliness of Being an Entrepreneur
And Why I Still Talk About My First Business at 24
Being an entrepreneur is often romanticized — the freedom, the passion, the grind. What people don’t talk about enough is the isolation. Behind the Instagram quotes and late-night laptop sessions is a reality many founders quietly endure: being an entrepreneur can be incredibly lonely.
You’re the Only One Responsible
When you start something from scratch, it’s yours. That sounds empowering, but it also means the weight is on you. Every decision, every mistake, every sleepless night — it’s all on your shoulders. There’s no boss to ask for help, no safety net. You might have advisors or investors, but when things go sideways, they’re not the ones picking up the pieces.
Friends and Family Don’t Always Get It
Start talking about revenue or burn rate at a family dinner and watch eyes glaze over. Your friends might be rooting for you, but they often don’t understand what you’re doing — or why you're working 14-hour days on something that’s barely paying the bills. Over time, the disconnect grows. You start skipping social events, answering fewer texts. It’s not intentional — you’re just consumed. But the result is distance.
I Still Remember the Start Like It Was Yesterday
When I started my first business at 24, it was the most exciting time of my life. I had no safety net, no corporate safety blanket — just raw drive, and a loan from my dad that I’ll always be grateful for. That money didn’t just help me get started. It gave me belief. Someone I looked up to was willing to bet on me.
I launched in Florida and hit the ground running. I was working 16 hours a day, seven days a week. It wasn’t glamorous — but I loved it. The pressure didn’t scare me. It fed me.
One thing that kept me grounded through the chaos was fitness — something else my dad drilled into me. No matter how packed my days were, I always trained. Whether it was lifting weights or hitting the gym, I showed up. That daily discipline helped me stay sane. It reminded me that I could push through — even when everything else felt uncertain.
Why I Still Talk About It — Even Now
Now I’m 47. I’ve sold businesses. I’ve started others. I’ve had wins I couldn’t have imagined back then — and failures that taught me more than any book ever could.
But I still talk about that first business because it shaped who I am. Not just as an entrepreneur — but as a man.
That time in my life was raw. Real. Nothing was handed to me. I had to earn every inch. And when you go through that kind of fire early on, it leaves a permanent mark. It teaches you what you’re made of.
Sharing that story matters — especially for the ones just starting out. Not everything has to be polished. Not every story ends with a million-dollar exit. Sometimes, it’s just about being in the fight and refusing to quit.
You Hide the Struggles
Entrepreneurs are expected to project confidence. Investors want to hear you're killing it. Customers need to believe in your product. Your team looks to you for stability. So even when things are falling apart, you smile through it. You pretend everything’s fine, because that’s what the job demands. That constant masking? It’s exhausting. And it feeds the loneliness.
Success Doesn’t Solve It
Even when things start to work — when revenue grows, when people notice — the pressure only shifts. Now you’re worried about scaling, about competition, about keeping everything from slipping through your fingers. You’ve still got no one to really talk to about it. Success might change your circumstances, but not always your isolation.
What Helps
The loneliness won’t disappear overnight, but there are ways to manage it:
Find real peers. Join groups where founders speak honestly — not just about wins, but about failures, doubts, burnout.
Be honest. With yourself and with others. Vulnerability isn’t weakness. It’s human.
Get a therapist or coach. You need someone in your corner who isn’t a cofounder or investor.
Make space for life. Relationships, hobbies, rest — these aren’t distractions. They’re lifelines.
Final Word
Being an entrepreneur can be deeply rewarding. But let’s stop pretending it’s all passion and hustle. The road is long and often lonely. You don’t have to walk it in silence — and you’re not the only one who feels this way.
That’s why I tell my story. Because 24-year-old me had no clue what was ahead — only belief and discipline. And even now, with decades of experience, I go back to that version of myself. Because he didn’t have it all figured out — but he showed up, every day.
So if you’re just starting your journey, here’s what I’ll say:
Keep showing up. Keep building. Stay in the fight. You’re not alone.