Serial Entrepreneur: What Is It and How To Become One

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[vc_empty_space height=”20px”]Thinking about starting a business? What about starting multiple businesses at once or many over your lifetime? This isn’t just a fantasy; there are many people out there that do this every day. Some fail over and over until they succeed. Some get companies off the ground like it’s a sport. 

What Are Serial Entrepreneurs?

Serial entrepreneurs are people who start many different businesses with varying degrees of success. Some of them may start with just one business, sell it and move onto the next. Others start multiple businesses at once and delegate day-to-day responsibilities to managers. 

The exact definition can vary depending on who you ask. Some serial entrepreneurs fail over and over with no success, and others find success many times. There is no secret formula that is universally used by all “SEs.” 

Sir Richard Branson

You may have seen Mr. Branson’s name in news headlines lately for literally going into space. Born in 1950, England, Sir Branson is a prominent businessman, investor, and author. In the 1970s, he founded the Virgin Group. This company has over 400 businesses underneath its umbrella. 

In 2000, Sir Branson was knighted at Buckingham Palace for services to entrepreneurship. He even made Time’s 100 Most Influential People. Most of the businesses that are under him are involved in retail, music, and transportation. 

One of Sir Branson’s most recent projects is Virgin Galactic. Branson’s company owns a 24% stake in the company, and they plan on revolutionizing the transportation industry with flights to space for tourists. 

Branson believes that the most important aspect of a company, big or small, is the people in it. Collaboration and good listening skills are essential to the success of any business venture.  

Oprah Winfrey

Born in 1954, Oprah Winfrey is a talk show host, television producer, author, and many other things. She is also heavily involved in charity work and fundraising. She is most famous for the Oprah Winfrey Show, which ran for 25 seasons. 

Oprah is the founder and owner of numerous companies like Weight Watchers and Oxygen Media. 

Michael Rubin

Michael is an American businessman and executive chairman of Fanatics. The company is the top provider of sports memorabilia. He has started multiple successful eCommerce websites and even sold GSI Commerce to eBay for $2.4 billion in 1998. 

Rubin achieved some mild success in early life but also got into debt from bad investments and failed businesses. He eventually started a sports equipment company that became rapidly successful, with millions in sales each year. 

From then on, Rubin began making smart investments and business decisions that would ultimately make him a billionaire. 

Ideas and Inspiration

If you have a dream to create a company and provide value, that’s only the start. There are skills you’ll need to learn and people that you will need help from. Communities are an essential asset and driving force to thriving companies.

No More Flying Solo

Business is a team sport. If you have an idea for a product or service that you’d like to create, you need to surround yourself with like-minded people who believe in your goals. Be careful not to surround yourself with yes-men who do nothing but praise every idea you have. 

Sometimes, you need a dose of reality or a different perspective on possible challenges or problems. Most successful companies were started not by just one person, but by multiple partners. 

You could think of starting a company like raising a kid. It’s a lot easier when there are two parents rather than one. It’s also rare for a single person to have the capital necessary to start a company. 

With multiple starting partners, you can pool your ideas and financial resources to ensure a higher likelihood of achieving your goals. Like Bill Nye once said, “Everyone you will ever meet knows something you don’t.” 

The weight of this quote cannot be understated. We, as a species, are naturally cooperative and work much more effectively and efficiently in groups that communicate well. Although it is important to be firm in the way you conduct business, it’s also important to keep an open mind.

It’s possible, even likely, that your vision will be changed and altered by your partners depending on things like market research, financial capabilities, and even luck. You need to be flexible in these situations.

Prepare for the Worst

It’s true that serial entrepreneurs fail a lot—more than you might think. That’s because they are known for their achievements and not their failures. When constructing your business plan, you will need to account for everything that can and will go wrong. 

As far as investments go, it’s considered wise to only invest what you are willing to lose. It’s cliche at this point to hear “I risked it all,” but how many times have you heard people say that and they weren’t successful?  

Not very many because those people aren’t on TV or on the covers of magazines. Something that is rarely spoken of in interviews with entrepreneurs; insurance. It’s crucial to consider insurance options for assets acquired for your business. 

Something simple like a random flood can completely destroy your endeavor overnight, and the blow could have been softened if you had just gotten a policy.  

Always Tell Me the Odds

It’s sad but true; Huge numbers of business ventures fail. Many serial entrepreneurs like Sir Richard Branson will tell you all about the failed companies he started and that it took multiple tries to get a company to survive and thrive. 

There are those that risked more than they had and ultimately paid off. However, if you are partaking in a venture that will make you lose everything if it fails, you may want to reconsider your ideas. 

As an example, around 60% of new restaurants fail within the first year of opening, and almost 80% fail before their fifth year of business. The world of business is cruel and without mercy. You could have an idea that could change the world, and if one thing goes wrong, everything you worked for could collapse. 

It’s important to learn how others have failed because that is how you learn to succeed. Failed businesses are lessons for new entrepreneurs. Really listen to people who started restaurants, factories, etc., and figure out what went wrong. 

Reasons Companies Go Under

Companies die for all kinds of reasons, but they usually fall under a broad few issues: lack of capital, poor marketing, bad management. If your company’s starting budget is too tight, you won’t be able to account for a litany of problems that can and will happen.

What if your partner pulls out of the project? What if a supplier you were counting on is running a month late? What if the location you bought or leased has construction going on in front, and people can’t see your signs? 

Another big issue is management style and consistency. Maybe your personality doesn’t fit the industry that you chose to be in. These are things you will need to adapt to. If you decide to start a fishing boat company, but you don’t like to wake up before the sun rises, it might be time to rethink what lifestyle you’re expecting. 

Remember to treat people you hire not as robots but as people. If you succeed in that, you will have an easier time hiring and retaining talent. Learn how to delegate to your top employees. You aren’t Superman. You simply can’t do everything. 

A big reason why so many companies never take off is not having a clear vision and set of goals. Many people who start businesses will say things along the lines of “we’ll probably do this or that, and we’re thinking of doing this.”

This is a tell-tale sign that there is not a clear goal in mind and that those things they talked about will probably never happen. Don’t sit and think about giving an investor a call; do it. You and your partners need to be very proactive in the entire process. Nobody is going to show up and do everything for you. 

Hidden Risks

One of the possibilities in serial entrepreneurship is cashing out too early on successful startups. This particular risk is very difficult to calculate and predict. People sell shares in companies just to find out those shares doubled in value very shortly after all the time. 

Something you can do to mitigate the risk of missing out is retaining partial ownership in the companies you create and sell. This way, you can move on to new ventures while not missing out on the possibilities of future success. And if that company fails, it’s not like all of your assets were resting on the success of that company. 

Try, Try Again

Serial entrepreneurs are known for one thing: never giving up and trying over and over. These people are relentless, and that’s the kind of attitude you will need to become one. 




Serial Entrepreneurship: Learning by Doing? | The University of Chicago Press Journals

Frank Flynn: Are We Intuitively Cooperative or Selfish? | Graduate School of Stanford Business

The True Failure Rate of Small Businesses |



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