What Is A Serial Entrepreneur [How To Become A Serial Entrepreneur]

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Many dream of becoming an entrepreneur but have you ever thought there is something called serial entrepreneur? But what is a serial entrepreneur? In this article we are going to understand exactly what does serial entrepreneur mean and how to become a serial entrepreneur?

Launching a prosperous business is no walk in the park. Statistics reveal that one out of every five businesses doesn’t make it past the initial two years, and almost half never reaches the fifth anniversary. The reasons for failure are diverse – perhaps the marketing strategy falters, funds dry up before gaining momentum, or unforeseen challenges like a pandemic, war, or a cost-of-living crisis disrupt the business plans.

At times, the hitch might be that people simply aren’t interested in what you’re offering.

It requires someone bold, talented, and perhaps a bit fortunate to embark on a successful entrepreneurial journey. Therefore, when a founder not only establishes one but multiple successful businesses, that’s truly exceptional.


What is a Serial Entrepreneur?

A serial entrepreneur is someone who takes on the challenge of starting multiple businesses. They might sell or step back from one business before diving into another, or they might run several businesses simultaneously while entrusting leadership roles to others.

Beyond just establishing their own companies, these entrepreneurs often venture into investments or become involved in other early-stage startups that ignite their passion.

What is a serial entrepreneur?

This type of entrepreneur is typically adept at spotting new business opportunities and crafting a vision for a company. They find the most excitement in the early phases of a business, tackling tasks like conceptualizing products, building teams, and attracting investments.

Related: How to write a company profile

Ambitious and skilled at solving problems, they possess a robust tolerance for risk, a constant flow of new ideas, and a keen understanding of the market.

Related: 50 low-cost business ideas

Serial entrepreneurs come in diverse forms – from managing a street stall selling apples to co-founding a tech giant like Apple Inc. In reality, many serial entrepreneurs are active in multiple, unrelated industries.

Serial Entrepreneur Characteristics

There’s no specific recipe for evolving into a serial entrepreneur, but certain qualities can pave the way for founders to achieve a series of successes.

     Vision: Serial entrepreneurs are individuals brimming with ideas who can imagine a better world and chart a course to reach it.

     Problem-solving mindset: Serial entrepreneurs view challenges and hurdles as chances for growth and don’t easily give up when faced with adversity.

     Restlessness: Serial entrepreneurs quickly become bored. They possess inquisitive minds and are always contemplating what lies ahead.

     Drive: Serial entrepreneurs harbor a deep passion for their ventures. They link their work to a broader purpose that serves as motivation, whether it’s addressing customers’ pain points or revolutionizing an industry.

     Adventurous spirit: Serial entrepreneurs exhibit a high tolerance for risk and are unafraid to explore new avenues of approach things in unconventional ways.

6 Serial Entrepreneur Examples

When it comes to serial entrepreneurs you may know a few of the names. Here are few of the examples of serial entrepreneurs:

  1. Elon Musk
  2. Richard Branson
  3. Oprah Winfrey
  4. Jan Ryan
  5. Sarah Jane Thomson
  6. Lebona Moleli

1. Elon Musk:

“I don’t start companies just for the sake of it, but to accomplish things.” — Elon Musk (FCO Roundtable, 2012)

No compilation would be complete without the man who revolutionized electric vehicles, space travel, and online payments. Musk sold his initial venture, Zip2, for $307 million in 1999. Since then, he’s played a crucial role in shaping PayPal, Tesla, SpaceX, SolarCity, and The Boring Company. Musk’s ambitious dreams, coupled with his willingness to take significant risks, truly define him as a quintessential serial entrepreneur.

Related: 39 Entrepreneur lessons for your business

2. Richard Branson:

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

Few can boast of influencing the career of the Rolling Stones, journeying into space, and receiving knighthood from the Queen. This British entrepreneur’s business portfolio has, at different times, included a record label (Virgin Records, sold for $1 billion), a rail franchise, a mobile network, and an airline.

3. Oprah Winfrey:

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

While renowned as the talk-show queen who coaxes celebrities to open up on her couch, Winfrey has transformed her fame into a series of prosperous ventures. Her production company, Harpo, Inc., marked the first major studio controlled by a Black person. Oprah has founded a magazine, a radio channel, a television network, and co-produced a Broadway musical.

4. Jan Ryan

During the ’70s, when Ryan served as a product specialist at IBM, her division had a suggestion box where employees could drop ideas on index cards. Each week, the employee with the best idea would be rewarded with $100. Ryan was so successful in this competition that they eventually had to stop it.

“I realized I needed to be in a place where I could make a meaningful contribution,” she recalls.

Her opportunity came in 2005 when she was recruited to overhaul Sigma Dynamics, a startup specializing in predictive analytics software for anticipating customer behavior. As the CEO, she led the company through a successful relaunch, attracting notable clients such as Bank of America. Just a year later, Oracle acquired the company.

Observing the rise of social media, Ryan noticed a gap in utilizing the technology for customer service. To address this void, she founded Social Dynamx in 2009, a SaaS startup facilitating customer service through social media channels. The company was acquired by Lithium Technologies three years later.

“Serial entrepreneurs are drawn to trends that will disrupt society,” says Ryan, “but you don’t want to follow the crowd.”

5. Sarah Jane Thomson

The former director of sales and marketing, Sarah Jane Thomson, had a dream that led her to launch the media monitoring and consultancy firm, Ebiquity, in 1997. Testing out the idea with her husband during her maternity leave, Thomson was among the pioneers in using the internet to gather real-time advertising expenditure data for UK marketers.

Less than three years later, the couple listed the firm on a submarket of the London Stock Exchange. Although the Thomsons are no longer at the helm of the company, which generated $78 million in revenue in 2021, Sarah Jane has ventured into four more projects:

     In 2006, she launched First News, a children’s newspaper that is now distributed to nearly half the schools in the UK.

     In 2007, she founded Priority One, a company providing IT and cybersecurity services to businesses.

     In 2018, ThreatAware was introduced, a platform for businesses to manage cybersecurity tools.

     Also in 2018, Discover.Film was launched, a short film streaming service boasting over 1 million viewers per month.

Related: 20 Best entrepreneur tools

Sarah Jane Thomson, actively involved in all four companies, points out that the ability to achieve a better balance between family life and work was a significant factor that drew her to entrepreneurship.

“When I expressed my desire to move to a three-day week [after giving birth] to my boss at the time, he told me I had to choose — motherhood or a career,” says Thomson. “So, that determination fueled my ambition — to have the flexibility to work on my own terms.”

6. Lebona Moleli

Moleli’s journey into the business world began early when, at the age of 12, he honed his entrepreneurial skills by selling vegetables from his grandmother’s garden door to door. After spending 15 years in the field of marketing, including a stint at Coca-Cola, he decided to merge his professional expertise with the entrepreneurial spirit cultivated since childhood.

His initial venture, a market research company, turned out to be less successful, leading him to part ways with his partners after eight months without generating any income. Undeterred, Moleli persisted and has gone on to launch five more companies:

     In 2008, he founded The Marketing Kraal, specializing in outdoor advertising like billboards and wall murals.

     2009 saw the establishment of Lesaka Marketing, a consultancy developing marketing plans for small and medium enterprises.

     Thuto Travel and Tours, a shuttle and tours service, was founded in 2010.

     In 2015, Lebona Investments emerged, focusing on property investment, farming, and small-scale manufacturing.

     The most recent addition, in 2018, is the Mohope Brewing Company, a 100% Black-owned craft brewery.

Moleli highlights one of the perks of managing multiple companies: the avoidance of reliance on a single income stream, which can 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 might come across stories of accomplished entrepreneurs, making their achievements seem rare and unattainable. However, it’s worth noting that 30% of self-employed individuals are serial entrepreneurs. Here are a few tips that could assist you in joining their ranks.

Here are 4 steps to become a serial entrepreneur:

  1. Picking an industry
  2. Evaluating the idea
  3. Start trying
  4. Balancing the plates

1. Picking an industry

Moleli suggests delving into ventures within industries you know and understand well. On the flip side, Thomson admits she had little knowledge about the industries she entered. She recommends surrounding yourself with knowledgeable individuals.

“The key is to fill your gaps,” she advises. “There will always be people with more experience and expertise than you. The crucial aspect is to envision something compelling enough that you can inspire talented individuals to join you on your journey.”

2. Evaluating the idea

Moleli prefers conducting thorough market research, whereas Thomson leans towards “socializing” business ideas by sharing them with friends, family, and individuals within the target market, listening to their feedback.

Beginning with the right questions is crucial as well. Ryan emphasizes, “Inexperienced entrepreneurs ask ‘Can it be done?’ and ‘How do you make money with it?’ In reality, they should be asking, ‘Who needs this?'” She adds, “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 they tell you there’s no need for this, then you move on.”

3. Start trying

Some businesses can kick off with minimal to no investment. Thomson and her husband created a mock-up of their first product, using it to attract their initial paying customers. Moleli began with just his laptop and a few valuable connections in his network. On the other hand, some startups might need to seek early investments.

However, the crucial point is to initiate the process, as the initial stages will involve a lot of trial and error. “Take action,” suggests Ryan. “Then reflect, think about what is and isn’t working, and take action again.”

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

4. Balancing the plates

When questioned about how they manage with so much going on, all three entrepreneurs The Hustle interviewed highlighted the importance of delegating and forming a robust team around you. Ryan emphasizes, “The operative word is ‘team.'”

Moleli mentions, “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?

As per salary.com, the average annual base salary for a U.S. serial entrepreneur stands at $64,686, with most earning between $54k and $76k per year. However, in reality, the salary range for serial entrepreneurs is vast, spanning from zero to millions.

One contributing factor is the broad spectrum of ventures that serial entrepreneurs may lead — ranging from small corner delis and laundromats to billion-dollar tech giants employing tens of thousands.

In the initial stages, many entrepreneurs opt to reinvest profits back into the business rather than drawing a salary. Notably, Steve Jobs, the founder of Apple and Pixar, famously received a salary of just $1 per year as the CEO of Apple from 1997 to 2011. Clearly, his strategy proved successful.

In other instances, entrepreneurs may not receive a conventional salary as they are compensated through various means. For instance, Thomson pays herself in dividends and also generates income from her company stock.

Similarly, Musk earns his income through Tesla stock options that vest when the company achieves specific targets. After the company reported record quarterly profits in April, Musk is set to receive a bonus share payout worth $23 billion — and that’s just from one of his ventures.

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