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Reading: Dave Ramsey’s EntreLeadership: Sometimes, It’s Lonely at the Top
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FundsForBudget > Debt > Dave Ramsey’s EntreLeadership: Sometimes, It’s Lonely at the Top
Debt

Dave Ramsey’s EntreLeadership: Sometimes, It’s Lonely at the Top

TSP Staff By TSP Staff Last updated: October 15, 2025 3 Min Read
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Dave,
When I started my business, I never realized just how lonely leadership can feel. The weight of every decision, pressure to protect the culture and having very few peers who understand how heavy things can be is overwhelming sometimes. How did you stay grounded and connected during the early days of building your company?
Derek

Derek,
I’m going to be honest with you. The reason you feel like you’re doing it all alone is because you’re doing it — all alone. And you’re right. It’s heavy, and it gets lonely. But it’s one of the prices you pay when you decide to own and run a business and serve others. For better or worse, it goes with the territory.

When I first started, I didn’t know of any businessmen’s groups or support organizations for small-business leaders. So, I took a pretty simple route and began calling and emailing other businesspeople and ministry leaders, asking if they’d like to do a weekly Bible study together. It wasn’t something I was teaching; I just wanted to get in a room and connect with people.

Putting together that little group turned out to be one of the best things I’ve ever done. We learned so much about God, our faith and ourselves over the 14 years we met together. We went through a lot of life together — good and bad. Eventually, we began learning about each other’s businesses and careers, and we began exchanging ideas that helped us all learn and grow professionally as well. Of course, now I have a wonderful team around me, and things aren’t so lonely anymore. My leadership team is made up of men and women of all ages. They’re all very mature, sophisticated and smart. We’re here for each other every day.

That said, I still think it’s extremely important to associate with people who are at, and beyond, the level you find yourself. It doesn’t matter if you’re talking about spiritual development or everyday business practices — the principle’s the same. So, I’d suggest finding a local civic club or advisory group, something that features group coaching like we do in EntreLeadership. Ask about becoming a member of something like this, or just start attending meetings of your local Chamber of Commerce and introduce yourself. My guess is you’ll find plenty of folks in the same place you are, and with the same concerns you have.

I really appreciate the honesty and vulnerability in this question, Derek. God bless you, and best wishes!
Dave

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