Interested in Serial Entrepreneurship? Read This First

Serial entrepreneurs own more than one business at a time. While serial entrepreneurs can profit tremendously from multiple ventures, it requires a skillset not all business owners possess.

Launching a startup and expanding your business may be a dream shared by many, but other aspiring entrepreneurs are much more interested in sparking new ideas that launch businesses over and over again.

Entrepreneurship is on the rise -- in 2019 alone, 472 million entrepreneurs launched over 100 million startups across the world. Thanks to advances in digital technology, it’s easier than ever to start your own business and become an entrepreneur.

However, not every entrepreneur is interested in managing a startup once it becomes sustainable. Instead, some prefer to move on to new ventures that require the same level of creative energy and determination that it took to launch their first business.

If you love the idea of launching a new product or forming a disruptive business that can change the way we live, but aren’t tied to managing that company for the next decade, you might be interested in exploring serial entrepreneurship.

Overview: What is a serial entrepreneur?

There are many different types of entrepreneurs, but a serial entrepreneur is one who focuses on growing an idea from conception to fruition, then moves on to the next big business idea. Essentially, a serial entrepreneur will take their business idea, launch a business, get it running, and move on once the business reaches a certain level of maturity and success.

Serial entrepreneurs may end up selling their businesses, or they might retain ownership and delegate daily operating responsibilities to others. Those who opt to retain ownership typically have built successful entrepreneurial teams capable of managing the company, which means the entrepreneur can essentially step down or back from their leadership role.

How do serial entrepreneurs manage several businesses?

If you decide to become a serial entrepreneur and want to retain ownership of your businesses, you’ll need to manage several businesses at one time. Even though you won’t be handling the day-to-day tasks of running your businesses, you’ll still want to play an active role in all of your companies to ensure revenue generation is up and new product launches or expansions are successful.

This will require a strong, accountable, and trustworthy leadership team. You’ll also need to check in on your businesses anywhere from once a week to a few times a month to ensure there are no red flags in any business or sales plans. Quarterly reviews with all shareholders will also be important in analyzing the previous quarter’s numbers and setting the right course for short- and long-term goals.

5 characteristics of serial entrepreneurs

Not everyone is cut out to be a serial entrepreneur. It requires a certain skill set and willingness to move on once a company becomes sustainable. If you’re interested in this type of business role, here are five serial entrepreneur characteristics you’ll need to develop.

1. Goal-setting skills

When you’re a serial entrepreneur, setting specific and measurable goals is essential to your success. Since you’ll move on to the next venture once your current company is up and running, you’ll need to set a concrete goal to help meet your timeline.

For instance, instead of saying, "I want this app to be sustainable in the near future," you’ll set specific goals such as, "I want to generate $1 million by the end of 2021," or "I want to reach 500,000 subscriptions in the next quarter." When you set SMART goals, you give yourself measurable outcomes to work toward, so you can begin quantifying and tracking your progress.

2. Excellent time management

Time management might be one of the biggest challenges for entrepreneurs. Serial entrepreneurs are responsible for multiple companies. In order to keep abreast of any new changes, business ideas, and challenges, you’ll need to develop excellent time management skills, so you can work smarter and not harder.

It requires a bit of insight to discover how to work most efficiently. You can meet several times a week per business and still find you have questions, unfinished tasks, and responsibilities to handle. Instead, decide how your time is best spent. Reviewing notes from important conference calls and checking in with leadership once a week or month might be a more valuable use of your time.

It’s important to figure out how you can save time since you’ll be juggling management responsibilities for several businesses. If a large issue arises, you’ll need to be able to quickly free up time to pitch in, without sacrificing your responsibilities to your other companies.

3. Flexible thinking

Change is constant, and the ability to change direction on a dime in order to profit and uncover better solutions is a quality all serial entrepreneurs share. It’s easy to become rigid in the way you think. Doing things the same way simply because that’s how it’s always been done will thwart anyone hoping to become a serial entrepreneur.

The marketplace can change without warning, and new technologies are released every day. A strong serial entrepreneur will quickly adapt to work with new ideas and innovations rather than trying to fight against them.

4. Optimism

Being an entrepreneur can be difficult. You must handle rejection, setbacks, and on occasion, even business failures. A serial entrepreneur knows not every plan will lead to success. Rather than getting hung up on what went wrong, a true entrepreneur looks at why a particular plan failed and learns from these mistakes.

Having an optimistic spirit and outlook is crucial in a business world full of constant rejection and skepticism. You’ll need to be able to believe in yourself and your ideas fully and confidently to make it as an entrepreneur.

5. Curiosity

Entrepreneurs are curious by nature. They love learning, testing theories, and exploring ideas -- even if they fall flat. New business ideas spring from curious minds. To keep building new, innovative companies, you’ll need to be continuously curious and creative in your brainstorming approach.

A serial entrepreneur doesn’t run multiple businesses simply because they want to build wealth or multiple streams of income. While those factors do draw individuals to entrepreneurship, it’s curiosity and exploration that allows a business owner to successfully grow and launch multiple startups.

4 examples of famous serial entrepreneurs

Many of the more famous and well-known entrepreneurs are actually serial entrepreneurs. Even though they are closely associated with one particular startup or product, these four serial entrepreneurs successfully run multiple businesses.

1. Elon Musk

Elon Musk is best known for Tesla, but before joining the electric car giant, he was a successful serial entrepreneur. He made and sold his own video games, founded Zip2, a digital content company that helped other newspapers and print media get online, and joined and expanded PayPal. While Musk has revolutionized Tesla, he’s also working on his next venture, SpaceX.

2. Oprah Winfrey

You undoubtedly know Oprah Winfrey as a television personality, but may not have thought of her as a serial entrepreneur before. But she is. Winfrey founded Harpo, her own production company, Oxygen Media, and several other print and publishing companies. She also owns OWN, the Oprah Winfrey Channel, where she produces and stars in multiple TV shows and movies.

3. Sir Richard Branson

Perhaps one of the most famous serial entrepreneurs of all time, Sir Richard Branson started his entrepreneurial goals early. He founded his own student-run print magazine called Student and later went on to found the first mail delivery record service, Virgin, which eventually spun off into a recording studio and record store.

Branson has since founded multiple companies in the travel, beverage, and broadcasting sectors and remains one of the top serial entrepreneurs in the world.

4. Wayne Huizenga

Wayne Huizenga was another notable serial entrepreneur who founded three multibillion-dollar companies to date. Huizenga first launched Waste Management in the late 60s, then Blockbuster in the 80s, and lastly, AutoNation in the late 90s. He also owned three different sports teams in his lifetime: Miami Dolphins, Florida Marlins, and Florida Panthers. He also founded multiple other startups. Huizenga passed away in 2018.

Is serial entrepreneurship right for you?

There are many ways to become an entrepreneur if you have the determination and confidence to make your visions happen. If you’d like to eventually own multiple companies, a career as a serial entrepreneur or serial investor might be right for you. Just make sure you plan out specific goals, hire dependable and reliable management teams, and work on improving your time management skills.