Before I started as CEO of Insureon, I enjoyed a fairly comfortable executive position with a major insurance company. Sure, I had a lot of responsibility--that comes with having 20,000 direct reports--but I also had staff to take some of the load off. Need research on a possible distribution channel? Contracts drawn up for a client? Numbers for a new market? No problem. My team could handle it.

But my first day at Insureon, it was just me. I went from running the show to running out to buy pens. That day, I had one thought: "What have I gotten myself into?"

At least half of you are rolling your eyes and thinking, "He had to buy his own office supplies. Poor guy!" But hear me out. This story isn't about buying pens; it's about the shift in thinking that has to come if you're going to make it in the long term as an entrepreneur.

Going it Alone Doesn't Mean Doing it All

We tend to think of entrepreneurs as trailblazing lone wolves. They cut away from the rat race to chase their vision and put their dreams into motion. It's a romantic notion, and it's not entirely untrue.

But I'm here to tell you that no dream or empire has ever been realized without the help of a team. When you start your own business, you quickly learn two things:

  1. You can't do it all yourself.
  2. You need people you can trust to help run the business.

Look at the example of Harry Gottlieb, CEO of the Chicago-based gaming company Jellyvision. Gottlieb founded the company in 1989 and ran it until 2012 when the board promoted his then-president Amanda Lannert. In the press release announcing Lannert's promotion, Gottlieb said, "I mean, look, Amanda has essentially been doing 89 percent of the CEO job since 2008. Since we've doubled our revenue three out of the last four years--AND she can finish my sentences, I figured I'd just better hand over the keys."

But that doesn't mean Gottlieb has been run out of the company. As the Chicago business magazine Crain's points out, he's been focused on product development--an area that seems to be a better fit for his skill set. The combo seems to be working out, too. According to another Crain's interview, Jellyvision's revenue now tops $20 million.

It's a powerful lesson in leadership: sometimes being in charge means knowing when to let your team take the reins.

The Team Has to Come First

I may be at the helm of Insureon, but I can't lose sight of the fact that I'm not an expert in all arenas. In fact, if I want the company to thrive, I have to let other people take charge of the areas where I fall short.

Isn't that exactly what being part of a team is all about?

Getting the right people in the right roles is the key to building a successful company, but it usually means identifying your own shortcomings. You would never sacrifice your business for an individual who doesn't fit their role, so that needs to go double for you.

It's hard to delegate responsibilities, especially when you're the one with the most at stake. But if you don't entrust at least some of your duties to people with the appropriate skill sets, you risk even more.