The Rise of the Serial Entrepreneur

If entrepreneurship is in your blood, if you’re always looking for your next opportunity, if you can never be satisfied working for someone else…you might be a serial entrepreneur. Some people just aren’t satisfied unless they’re able to start a business. Even if they’ve already started other successful companies, this is the mentality of the serial entrepreneur: they are constantly seeking new opportunities to start and grow a company.

Here are a few inspiring lessons that other business owners can learn from serial entrepreneurs.

What Makes a Serial Entrepreneur?

The definition of serial entrepreneur is someone who starts multiple businesses, one after another. It doesn’t matter if every business succeeds — of course, it’s better if your successes outnumber your business failures — but the important thing is that serial entrepreneurs have an innate drive to keep coming up with new business ideas and starting new companies.

Some serial entrepreneurs operate in the same industry, while others jump from one industry to another depending on where their latest inspiration and expertise can best be developed. Many serial entrepreneurs start a business, grow it to a certain level of success, sell the business to new owners and use their profits from the sale to fund their next entrepreneurial venture.

Why Do Serial Entrepreneurs Buy and Sell Businesses?

Serial entrepreneurs are often creative, restless visionaries — they see the potential to create and build something new, and then they want to move on to a new challenge. Serial entrepreneurs are often more excited about starting, building and growing a business than they are about managing a business for the long term.

Some serial entrepreneurs buy small startups that they see as a good fit to merge into their company, or because they see the potential to buy an existing business and then help it grow. But serial entrepreneurs often prefer to start their own companies and then sell the business at a big profit once they have built the company up to a certain level of value.

“Buy low, sell high” is the mantra for serial entrepreneurs — they typically want to invest in businesses that have strong growth potential and that are being undervalued by the market. Serial entrepreneurs will often see promise in a company that other people have overlooked, or they will have confidence in their own ability to maximize the strengths of a company by bringing in new leadership and a new strategic vision.

What Are the Traits of a Serial Entrepreneur?

Serial entrepreneurs often have a self-deprecating sense of humor about how it’s impossible for them to ever work at a regular job. They typically are smart, creative, visionary and comfortable with taking risks. They have a restless energy, they want to keep moving forward in life, they want to keep building things and they want to keep growing.

Serial entrepreneurs tend to have all sorts of different personalities. Some are more outgoing and charismatic, while others are more introverted and analytical. Some are natural sales people, while others are more technically minded. Some have deep expertise in a particular industry, while some are jacks-of-all-trades.

But one thing that connects all serial entrepreneurs is a seemingly inextinguishable passion for starting and building businesses. They are idea-generating machines. They have the focus and drive and appetite for financial risk that helps them create something out of nothing, and to keep doing it again and again.

What Are the Risks and Drawbacks of Being a Serial Entrepreneur?

Sometimes a serial entrepreneur will find themselves being overextended, financially or otherwise. It can be risky to own multiple businesses at once. Some serial entrepreneurs find that while they love the early stages of building a business, they are not a good fit for being a long-term CEO for managing a more mature company. These entrepreneurs typically need to learn how to delegate to others and partner with other talented executives who have complementary strengths. If you’re a serial entrepreneur, it’s important to find good business partners and trusted executives who can help you manage the parts of the business where you might not have as much passion or expertise.

Another pitfall for serial entrepreneurs is that they sometimes take excessive levels of financial risk — they might sell a company and then eagerly invest the profits in a new business or industry where they don't understand the competitive landscape as well. Don’t assume that what worked at your previous business will work in your new one. Serial entrepreneurs need to be willing to continuously learn and grow and challenge their assumptions.

Ideally, over time, the serial entrepreneur can use their series of businesses as a kind of property ladder — gradually starting and building several profitable businesses and reinvesting the profits into more lucrative companies.

If you’re a creative, energetic, idea-generating, risk-taking person who can’t wait to get started with your next exciting venture, you might be a serial entrepreneur! Just be sure to manage your risks and partner with good people along the way. The best serial entrepreneurs understand that although they have powerful skills, smarts and strategic visionary sense, they don’t know everything and they need other good people to help them succeed.

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