Talking to seasoned entrepreneurs, you start to see a pattern. No one’s journey is a straight shot to the top, and no one has all the answers. I’ve been lucky to chat with some of the most down-to-earth business builders, and one thing is clear—there’s no secret sauce, just a lot of grinding.
My conversation with Charles Gellman, the CEO and co-founder of HiDOHealth, was a perfect example of this. His story is full of lessons you don’t learn in a business school—they’re all lessons from the trenches.
Let’s get into it. Here’s what Charles’ journey taught me, and hopefully, what you can take away too.
Persistence: The Unsung Hero
Charles didn’t sugarcoat anything—being persistent is what kept him going. When he started out, he was just a kid hustling door-to-door selling candy. He talked about those early failures with a kind of ease, saying, “You’ll fail more often than you succeed, but that’s okay.” And honestly, that hit home. We’ve all been there, thinking that maybe if we’re smart enough, we can avoid the failures. But hearing it from someone who’s been through it reminded me that the setbacks are what make you stronger.
In Charles’ case, it wasn’t the big wins that defined him—it was the fact that he kept going after hearing “no” again and again. He took each failure as a lesson and moved forward.
Key Takeaways from Our Discussion:
- Expect rejection: You’re going to hear “no” more than you hear “yes,” and that’s part of the journey.
- Every little win counts: Whether you’re selling candy or launching a product, each step gets you closer to your bigger goal.
- Listen to your gut: No matter how many doors get slammed in your face, trust that inner voice telling you to keep pushing.
Don’t Try to Do It All Yourself
Charles learned this lesson the hard way. In his first startup, he tried to do everything solo, and it nearly sank him. He shared that while he was bootstrapping on his own, his competitors were out there with 50-person teams and millions in venture capital funding. Unsurprisingly, the solo route didn’t work. He realized that if he wanted to make it, he couldn’t do it alone.
When he launched HiDOHealth, he took a different approach. He brought in the right people early on—advisors, team members, co-founders. One key player was Dr. Donison, a former health plan administrator. She saw potential in HiDOHealth from day one, even when they were still in the early stages with a rough demo. That early belief from someone so experienced made a massive difference. It opened doors and gave them credibility they wouldn’t have had otherwise.
Charles’ shift from trying to go solo to building a team wasn’t just about survival—it was about setting his business up for success. It’s a reminder that we don’t have to have all the answers or do everything ourselves. In fact, we shouldn’t.
What I Learned from His Experience:
- A solid team is everything: You can’t be an expert at everything. Surround yourself with people who complement your weaknesses.
- Find people who believe in you: It’s not just about talent—it’s about finding people who share your vision and have your back.
- Start small, but build smart: Whether it’s co-founders, advisors, or early hires, getting the right people involved early will set you up for success later.
Reflections from the Interview
Listening to Charles’ journey, I couldn’t help but feel like I’ve heard this story before—not because it’s common, but because the struggles and victories are something every entrepreneur can relate to. No matter how unique your business or your idea, the grind is universal. There’s a lot of uncertainty in entrepreneurship, and Charles didn’t shy away from that. “You don’t know what’s going to happen, but you keep going anyway,” he said. That’s what it boils down to.
Entrepreneurship isn’t about having the perfect plan. It’s about having the guts to keep going when things don’t go as planned. Hearing Charles talk about the importance of being persistent and surrounding yourself with the right people reminded me that the obstacles are part of the process. You’re going to get knocked down, but how you respond is what really matters.
Here’s What I’m Taking Away:
- The road is never smooth: You’re going to get knocked down more times than you can count. But the trick is getting back up.
- Mistakes are your best teacher: The faster you make them, the faster you’ll learn what works.
- Keep your eyes on the goal, but be flexible: Plans change. Keep your goal in mind, but be willing to pivot when needed.
- Fail fast, move on: Don’t drag out a bad idea just because you’re afraid to start over.
- Mentorship can make the difference: Having someone in your corner who’s been through the same struggles can give you a huge advantage.
Final Thoughts
Charles’ story is a reminder that entrepreneurship is anything but predictable. There’s no straight line to success—you’re going to stumble, face rejection, and second-guess yourself along the way. That’s part of the deal. But if you stick with it and surround yourself with the right people, those setbacks start to look more like stepping stones. The grind isn’t easy, but it’s what sharpens you.
CONNECT WITH CHARLES GELLMAN:
LinkedIn: https://www.linkedin.com/in/mshicgellman/
Website: https://us.hidohealth.com/