What is a serial entrepreneur?

What is a serial entrepreneur?
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Entrepreneurship is the quintessential American dream. Everyone has a business they’d love to start and great ideas about how they’d run that enterprise if only they had enough cash. But while the typical entrepreneur may have one or maybe two business ideas at most, some go above and beyond and start or work on multiple ventures simultaneously.

Someone who starts new businesses one after the other might be referred to as a serial entrepreneur. Serial entrepreneurship is a gateway to massive profits, and many of the most successful businesspeople are serial entrepreneurs as opposed to single-venture startup executives.

Today, let’s explore what a serial entrepreneur is and what they do day to day, look at how they start new ventures, plus look at some examples of successful “multipreneurs.”


multiple ventures

What is a serial entrepreneur?

A serial entrepreneur is a businessperson who starts and runs not just one company but several simultaneously.

For example, a serial entrepreneur might start a business venture right out of college. They grow that business’s value for a few years, then sell it to another executive and start a new business because they had another great idea.

single business

This highlights the typical economic pattern for most serial entrepreneurs. They:

  • Start a business
  • Run it long-term until it turns a significant profit or until it starts to falter or fail
  • Sell the business and take the profits
  • Use the profits to start another company

Over their professional careers, serial entrepreneurs may start several or even dozens of different companies. They know, perhaps better than any other business professional, that failure is a part of the process. For a “multipreneur,” a business failing is just an opportunity to take those lessons and apply them to the next successful venture!

typical entrepreneur

What are the characteristics of serial entrepreneurs?

Most successful serial entrepreneurs have key characteristics that allow them to keep going where others might give up. These characteristics include:

  • A very strong drive to succeed: Entrepreneurship is difficult in any industry. Serial entrepreneurs need to be able to pick themselves up after failure and keep going.
  • Vision: Good serial entrepreneurs must be able to envision excellent business ideas by studying the market and identifying opportunities.
  • A problem-solving attitude: To be a serial entrepreneur, you can’t give up as soon as things get complicated.
  • High risk tolerance: Serial entrepreneurship practically guarantees failure at some point, so you need to be able to accept that and keep going anyway.
  • Curiosity: Most serial entrepreneurs are restless and can get bored very easily. They are always thinking about what’s next rather than what they did previously.
  • Good financial savvy: This trait can be rare, as more than 60% of surveyed business owners report that they don’t feel confident in their financial or accounting abilities. However, understanding at least the basic concepts of business finance can provide the foundation on which you can build a stable and successful company.

That said, no two serial entrepreneurs are exactly alike, with each having their own personality, fixations, and business desires.

start new ventures

Serial entrepreneur examples

Fortunately, there are many successful serial entrepreneurs to look up to and take as examples.

Oprah Winfrey

Oprah Winfrey is perhaps the most famous American philanthropist alive today. But she’s also a very well-known serial entrepreneur!

You might mostly know her from The Oprah Winfrey Show, but she began her career as a TV anchor in the 1980s. Shortly after, she established the Harpo Productions Inc. company, through which she launched her titular TV show. As the third woman to own her studio, this put her on the map in more ways than one.

But Oprah Winfrey didn’t stop there. She founded the Oxygen cable TV station and launched the Oprah Winfrey Network in 2008. Today, Winfrey manages the magazine named after her and has authored many books. Thanks to her entrepreneurship adventures, she has an estimated net worth of over $2.5 billion.

Elon Musk

Who can forget the name Elon Musk? Musk began his entrepreneurship career with Zip2, a searchable business directory that was like an online version of the Yellow Pages. He founded this company in 1995, then sold it four years later for $307 million.

Musk was not content to be done with just that victory, however. He then founded PayPal known for its online financial serviceswith a business associate, selling the company to eBay for $1.5 billion.

Today, Musk is most known for SpaceX and Tesla Motors: two companies pushing the boundaries of science and technology further than they’ve ever gone before. More than many other serial entrepreneurs, Musk proves that you can pivot from industry to industry and still find success with the right mindset.

Richard Branson

Sir Richard Branson got his start as a serial entrepreneur early when he was 20 years old in 1970. At this young age, he began a mail-order record business. From that venture, he eventually grew the Virgin Group. Now, the Virgin Group owns 40 different companies and more than 200 distinct subsidiaries.

In essence, Richard Branson has built a diversified conglomerate of businesses to ensure he will always remain wealthy! Odds are you’ve heard of several of Branson’s companies in the past, like Virgin Atlantic, Virgin Clothing, Virgin Music, and so on.

Andreas von Bechtolsheim

This serial entrepreneur is one of the original co-founders of Sun Microsystems, a 1982 company that eventually grew into a billion-dollar business. However, von Bechtolsheim then established Granite Systems to manufacture network switches for other companies. He sold his company to Cisco Systems for $220 million.

That’s not all von Bechtolsheim accomplished in a short timeframe! He next moved to develop a server technology company named Kealia in 2001, sold that to Sun Microsystems in 2004, and then helped to cofound Arista Networks in 2005.

As if that wasn’t enough, von Bechtolsheim was one of the first investors in Google. With a $100,000 investment, he eventually gained a net worth of well over $9 billion.

Rod Drury

Last but not least is Rod Drury, a serial entrepreneur from New Zealand who primarily operates in the technology sector. For example, 1995 saw him establish Glazier Systems, then sell that company for $7 million in 1999.

Next, Drury founded AfterMail, quickly selling the company for $15 million in 2006. Drury is most well-known for founding Xero in 2006, one of the first software-as-a-service (SaaS) companies. He sold $95 million worth of his Xero shares in 2017, but not before founding Pacific Fiber: a company that attempted (without success, unfortunately) to make a fiber-optic internet cable that connected the United States, Australia, and New Zealand.

net worth

Are you the next serial entrepreneur?

Serial entrepreneurs make and evolve industries. They are important individuals in a capitalist market and are often behind some of the biggest companies ever created. But although their success may seem out of reach, anyone can become a serial entrepreneur.

That includes you! With the right knowledge and drive, you can become a serial entrepreneur starting multiple successful business ventures. It all starts with taking the right classes, of course. Teachable can help you find the perfect courses to learn everything you need to succeed in entrepreneurship. Alternatively, you can use Teachable as an online course platform to build your audience and begin a career as a serial entrepreneur specializing in online teaching.

unique ideas


What is the difference between an entrepreneur and a serial entrepreneur?

The difference between an entrepreneur and a serial entrepreneur is their focus. With a traditional entrepreneur, the focus is on one single idea or business at a time. Most business owners are traditional entrepreneurs. They have one or two unique ideas, grow their businesses from scratch, and develop those businesses over time. In many cases, they never leave their initial enterprises

Serial entrepreneurs, on the other hand, never stay in one place for too long. Like sharks, they have to keep moving to survive and thrive. In that way, they may start one company, lead it for a few years, sell it and move on to another enterprise.

However, entrepreneurs and serial entrepreneurs have many of the same characteristics, like:

  • Imagination
  • Ambition to succeed
  • Creativity
  • Leadership skills

What are the skills needed to be an entrepreneur?

To be a successful entrepreneur (serial or standard), you need to cultivate certain key skills. These skills include:

  • Strong leadership skills, particularly if you plan to have many employees.
  • Good communication skills so you can market successfully and lead your companies to success.
  • Strong market understanding. You need to know what gaps currently exist in the market and how you can leverage them for profit.
  • A lot of drive. To succeed as an entrepreneur, you need to be willing to buckle down and do a lot of work, often working more than 12 hours day-to-day.

Can anyone become a serial entrepreneur?

Yes! Anyone can become a serial entrepreneur with the right idea and ambition. However, it might be wiser to start as a standard entrepreneur. Start one single business, see if it works successfully, then move to a new venture once you have a great idea and your current business is valuable enough that you can sell it for a profit.

Nahla Davies

Nahla Davies, Nahla Davies is a software developer and tech writer. Before devoting her work full time to technical writing, she managed—among other intriguing things—to serve as a lead programmer at an Inc. 5,000 experiential branding organization whose clients include Samsung, Time Warner, Netflix, and Sony.

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