Starting a successful business is not easy. One in five businesses fail in the first two years and almost half never make it to their fifth birthday. Sometimes the marketing strategy is wrong. Sometimes the money runs out before the business gets momentum, or an unexpected pandemic/war/cost-of-living crisis throws a wrench in the works. 

Sometimes, people just plain old don’t want what you’re selling. 

It takes someone gutsy and talented (and probably a little bit lucky) to start a successful business. So when a founder comes along and succeeds with not one but multiple businesses, that’s pretty special.

What is a serial entrepreneur?

A serial entrepreneur is someone who starts multiple businesses. They may sell or step back from one business before starting another, or they may run multiple businesses simultaneously, delegating leadership roles to other people.

In addition to founding their own companies, they often invest or become involved in other early-stage startups that excite them. 

This kind of entrepreneur is typically an expert at identifying new business opportunities and creating a vision for a company. They tend to be most excited about the early stages of a business, including tasks like product conceptualization, team building, and attracting investments.

They are often ambitious problem-solvers with a strong stomach for risk, an endless list of new ideas and a keen understanding of the market.

Serial entrepreneurs come in all shapes and sizes — they could have a street stall selling apples or be the co-founder of Apple Inc. In fact, many serial entrepreneurs are active in several unrelated industries.

Serial entrepreneur characteristics

There’s no formula for becoming a serial entrepreneur, but there are some traits that can help lead founders to a string of success. 

  • Vision: Serial entrepreneurs are ideas people who can envision a better world and the route to get there.
  • A problem-solving attitude: Serial entrepreneurs see problems and obstacles as opportunities and don’t give up easily in the face of adversity. 
  • Restlessness: Serial entrepreneurs get bored easily. They have curious minds and are constantly thinking about what’s down the road.
  • Drive: Serial entrepreneurs are passionate about their ventures. They connect their work to a broader purpose that motivates them, such as solving customers’ pain points, or revolutionizing an industry.
  • An adventurous spirit: Serial entrepreneurs have a high tolerance for risk and are unafraid to try something new or do things differently.

Serial entrepreneur examples

The ones you know

“I don’t create companies for the sake of creating companies, but to get things done.” — Elon Musk (FCO Roundtable, 2012)
serial entrepreneur examples: Elon MuskThis list wouldn’t be complete without the man who has transformed electric vehicles, space travel, and online payments. Musk sold his first business Zip2 for $307m in 1999, and has since helped build PayPal, Tesla, SpaceX, SolarCity, and The Boring Company.  His outsize dreams, combined with his capacity for outsize risk, make him a quintessential serial entrepreneur.

“Business opportunities are like buses — there’s always another one coming.” — Richard Branson (Twitter, 2012)

 serial entrepreneur examples: Richard BransonNot many people can say they’ve played a role in the career of the Rolling Stones, traveled to space, and been knighted by the Queen. This Brit’s business empire has at one time or another included a record label (Virgin Records which he sold for $1B), a rail franchise, a mobile network, and an airline. 

“Create the highest, grandest vision possible for your life, because you become what you believe.” — Oprah Winfrey (Wellesley College Commencement Address, 1997)

 serial entrepreneur examples: Oprah Winfrey

The talk-show queen may be best known for getting celebs to bare their souls on her couch, but Winfrey has transformed her fame into a series of successful ventures. Her production company, Harpo. Inc, was the first major studio to be controlled by a Black person. She has founded a magazine, a radio channel, a television network, and co-produced a Broadway musical.

Successes from 3 continents

Jan Ryan (Austin, Texas)

 serial entrepreneur examples: Jan RyanSource: photo courtesy of Jan Ryan.

When Ryan was a product specialist at IBM in the ’70s, her division had a box where employees could leave ideas on index cards. At the end of every week, the employee with the best idea won $100. Ryan won so many times that they stopped running the competition.

“I knew I needed to move somewhere where I could actually contribute in a meaningful way,” she recalls. 

She got her chance in 2005, when she was recruited to revamp Sigma Dynamics, a startup that developed predictive analytics software that could help anticipate customer behavior. As CEO, she guided the company through a successful relaunch, attracting clients like Bank of America. Oracle acquired the company just a year later. 

As the use of social media grew, Ryan saw that no one was taking advantage of the new technology for customer service. To fill the gap, she launched Social Dynamx, a SaaS startup that helped companies provide customer service through social media channels, in 2009. The firm was acquired by Lithium Technologies three years later.   

“Serial entrepreneurs are attracted to trends that are going to disrupt society,” says Ryan, “but you don’t want to do what everyone else is doing.”  

Sarah Jane Thomson (London, England)

 serial entrepreneur examples: Sarah Jane ThomsonSource: photo courtesy of Sarah Jane Thomson.

The former sales and marketing director launched media monitoring and consultancy firm Ebiquity in 1997 after getting the idea through a dream. Thomson, who tested out the idea with her husband during her maternity leave, was among the first to use the internet to gather real-time advertising expenditure data for UK marketers. 

The couple listed the firm on a submarket of the London Stock Exchange less than three years later. The Thomsons are no longer running the company, which brought in $78m in revenue in 2021.  Sarah Jane has since launched four more ventures:

  • 2006: First News, a children’s newspaper that’s sold to nearly half the schools in the UK. 
  • 2007: Priority One, which provides IT and cybersecurity services to businesses.  
  • 2018: ThreatAware, a platform for businesses to manage cybersecurity tools.
  • 2018: Discover.Film, a short film streaming service with 1m+ viewers/month.

Thomson, who is active in all four companies, says the ability to better balance family life with work attracted her to entrepreneurship.

“When I told my boss at the time that I’d like to move to a three-day week [after giving birth], he said I had to decide — motherhood or career,” says Thomson. “So that’s what drove my determination — to be able to work to my own agenda.”

Lebona Moleli (Johannesburg, South Africa)

 serial entrepreneur examples: Lebona MoleliSource: photo courtesy of Lebona Moleli.

Moleli earned his business chops early, selling vegetables from his grandmother’s garden door to door at age 12. After 15 years in marketing — including a stint at Coca-Cola — he decided to combine his professional experience with the entrepreneurial spirit he developed as a child. 

His first attempt, a market research company, was a dud, and he parted ways with his partners after eight months without generating any income. But Moleli didn’t stop there, and has since started five more companies: 

  • 2008: The Marketing Kraal, which specializes in outdoor advertising, such as on billboards and wall murals.
  • 2009: Lesaka Marketing, a consultancy that develops marketing plans for small and medium enterprises.
  • 2010: Thuto Travel and Tours, a shuttle and tours service.
  • 2015: Lebona Investments, which invests in property, farming, and small-scale manufacturing. 
  • 2018: Mohope Brewing Company, a 100% Black-owned craft brewery.

Moleli says one of the advantages of running several companies is that you don’t have to rely on a single income stream, which could be risky.

“But money has never been my primary motivator,” he adds. “Starting a business is like bringing a child into the world. I enjoy watching the baby grow.”  

How to become a serial entrepreneur 

You may read about successful entrepreneurs and see their achievements as rare and out of reach, but 30% of self-employed people are serial entrepreneurs. Here are a few tips that could help you join their ranks.

Picking an industry

Moleli recommends pursuing ventures in industries you know and understand best. Thomson, on the other hand, says she knew very little about the industries she’s entered. She suggests surrounding yourself with knowledgeable people. 

“The key is [to] plug your gaps,” she says. “There will always be people better than you that have experience. The key is to envision something exciting enough that you can encourage talent to join your journey.”

Evaluating the idea

While Moleli prefers performing extensive market research, Thomson leans toward “socializing” business ideas by telling friends, family, and anyone who might be in your target market and listening to their feedback. 

Starting with the right questions is also key. “Inexperienced entrepreneurs ask ‘Can it be done?’ and ‘How do you make money with it?’ Really they should be asking, ‘Who needs this’?” says Ryan. “I have a radical customer-first orientation… It takes a lot of the risk out of it because if you start with the customer and if they tell you there’s not a need for this, then you move on.”

Start trying 

Some businesses can be started with little to no investment. Thomson and her husband made a mock-up of their first product and used that to get their initial paying customers. Moleli started out with just his laptop and a few useful connections in his network. Other startups may need to reach out to investors early on. 

But the key is to get going, as the early stages will be filled with trial and error. “Take action,” says Ryan. “Then reflect, think about what is and isn’t working, and take action again.”

“A good serial entrepreneur must be patient,” says Moleli. “Sometimes things take a while to reach fruition.”

Balancing the plates

When asked how they cope with so much on the go, all three of the entrepreneurs The Hustle spoke to emphasized the value of delegating and building a strong group of people around you. “The operative word is ‘team,’” advises Ryan. 

Moleli says, “You have to be able to multitask, [but] today the keyword is collaboration. I look for partners I can trust and partners that share my vision and understand how I work.”

How much do serial entrepreneurs earn?

According to salary.com, the average annual base salary for a US serial entrepreneur is $64,686, and most serial entrepreneurs earn between $54k and $76/year. In reality, the salaries of serial entrepreneurs can range from zero to millions. 

One reason is that serial entrepreneurs can helm a wide range of ventures — from corner delis and laundromats to billion-dollar big tech companies that employ tens of thousands of workers. 

During the early stages, many entrepreneurs will reinvest profits back into the business rather than draw a salary. Steve Jobs, founder of Apple and Pixar, famously earned just $1/year as the CEO of Apple during 1997 to 2011. Suffice to say, his strategy worked out well.

In other cases, entrepreneurs do not receive a salary because they are compensated in different ways. Thomson, for example, pays herself in dividends and also makes money off her company stock.

Similarly, Musk gets his gold from Tesla stock options that vest whenever the company hits certain targets. After the company reported record quarterly profits this April, Musk is due a bonus share payout worth $23B — and that’s just from one of his companies.

Subscribe to The Hustle Newsletter

Subscribe to The Hustle and Never Miss What’s Happening in Business & Tech

What did you think of this article? 

Give Feedback

Love

Meh

Hate

Originally published Jun 1, 2022 8:00:00 AM, updated June 01 2022

Topics:

Entrepreneurship