7 Signs You Might Be A Serial Entrepreneur

Do you think you’re a serial entrepreneur? These seven signs should help you decide.
Co-founder, KISSmetrics
December 06, 2011

Serial entrepreneurship has become a trendy business model lately. Start a business, grow it until you can sell and then do it all over again.

That might sound attractive, but it’s really not a lifestyle for everyone. Yet there are people out there who do it and love it.

Do you think you’re a serial entrepreneur? These seven signs should help you decide.

You are restless after three or four years

I’ve known successful first-time entrepreneurs who complain of being bored after a few years. In fact, they feel like they might have leaned their career against the wrong wall.

Some will feel guilty about their restlessness. They think they should be grateful that all their hard work has paid off. I ask them, “Have you ever thought that maybe it’s time for you to move on and start something else?” In other words, think like a serial entrepreneur.

Have you ever felt that way? Being restless is not a bad thing. Don’t try to change who you are. Instead, view that restlessness as a sign that it’s time to move on. Start looking for your exit strategy.

You are curious and customer-centric

Some entrepreneurs start a successful business and then transition with it into the mature stages of the company, helping build a company that will be around for awhile. Think Jeff Bezos and Mark Zuckerburg.

Other entrepreneurs don’t want any part of the routine-management side of running a business. They are idea people and won’t rest until they can turn every idea into a business.

But it’s not just about coming up with the idea or inventing something cool and new. These entrepreneurs look at problems from the customer perspective.

If you run into issues and think, I bet I’m not the only person who feels this way, look at your business through your customers’ eyes. Try a quick AdWords test to see if you can generate interest.

Or you might do a simple video like Dropbox founder Drew Houston did and share it with people to see if they have the same problem. If you find significant interest, you’ll start to figure out how to turn this idea into a product—even while running your current business.

If that sounds like something you would do, then you are probably a serial entrepreneur.

You have more fear of regret than of failure

I’ve never been afraid of failing. However, I am afraid of regret. I don’t want to look back on my life and feel bad that I missed an opportunity. I want to take risks and live life to the fullest. That means I like to start lots of businesses.

We hear this a lot: “Failure is not an option.” Well, serial entrepreneurs know better than to say that, because it’s not true. You will fail. It may not be your first business, but it might be your second or third.

You will fail as a leader and an innovator, too. You’ll fail countless ways, but for serial entrepreneurs, each failure is one more lesson on the way to getting it right.

You started a business before you could drive

Most entrepreneurs aren’t forming startups because they are greedy. Sure, they hope that in four years they can sell their business for $100 million dollars. But that’s not what really drives entrepreneurs.

What really motivates entrepreneurs is the challenge of making money. And they’ve had this drive from a very young age. I know that I did.

I was a sophomore in high school when I caught the bug. I was making six figures before I graduated and I let it go to my head for a little while. Until I realized it wasn’t so much the money I enjoyed, as it was the challenge.

You recognize your current startup won’t make money

A good serial entrepreneur will step away from her current business and evaluate how it is doing. Is it making enough money to reward you, your team and your family? Or, are you wasting time trying to keep it from sinking too fast?

Let’s say that you realize your company may never be profitable. I’ve known some entrepreneurs who were relieved by that news…not because they had a sadistic side. No, they were eager to start on another project. Closing down their current one gave them permission to do that.

You simply know you want to start another company

Nothing will persuade you. You’ll take the payout when an offer comes, if it comes, or you’ll find some other way to back out of your current business because you want to start another company. It’s as simple as that.

You already have your hands in two or three businesses

If your business card gives your title as “co-founder” and lists two or more companies, you are a serial entrepreneur.

You don’t always have to build and then sell, moving from one project to the next to be considered a serial entrepreneur. You might like the idea of keeping your nose in each business to mentor, advise or lead. But you have to ask yourself: Can you make that kind of commitment without sacrificing your family

If you are one of us

Do you show any of these signs of being a serial entrepreneur? If so, I wish you luck on your business-building career, and I hope to run into you at some point in the future.

What other signs indicate that a person might be a serial entrepreneur?

Co-founder, KISSmetrics