- What is a Serial Entrepreneur?
- Traits of Successful Serial Entrepreneurs
- Challenges Faced by Serial Entrepreneurs
- Success Stories of Serial Entrepreneurs
Q: What is a serial entrepreneur?
A. A serial entrepreneur is someone who continuously starts and runs multiple businesses, often moving on to new ventures after establishing and stabilizing their previous ones.
Running a business is not the easiest thing to do; one business can be a source of constant headaches and worries.
Hence, it is no surprise that when most entrepreneurs finally find that one business that works, they hold it close to their heart and nurture it for a long period.
Then there are those entrepreneurs who are seemingly unbothered by the numerous challenges of running one business. So, they step things up by piling multiple businesses in their portfolio, actively running or co-managing all simultaneously. Those are your serial entrepreneurs.
These entrepreneurs are markedly different from traditional entrepreneurs in the sense that they are seemingly not content with handling only one business over an extended period. They thrive on launching multiple businesses, one after the other.
Their doggedness is a source of inspiration for many aspiring entrepreneurs and enthusiasts. Because why have one when you can have multiple and emblazon your name in the sands of time?
Today, we’ll look at the traits of successful serial entrepreneurs, some challenges faced in the various paths to becoming a serial entrepreneur, and some serial entrepreneurship examples to inspire you even more.
But first, who is a serial entrepreneur?
What is a Serial Entrepreneur?
Put simply, a serial entrepreneur is someone who continuously starts and runs multiple businesses, often moving on to new ventures after establishing and stabilizing their previous ones.
Most serial entrepreneurs prefer to delegate the managerial responsibilities of their matured ventures to professionals while retaining ownership.
Some others are more interested in selling businesses. They put in all the work to develop a business and sell it off once it reaches a certain level of maturity. That said, they may hold on to some of their successful businesses because of their sentimental value.
A study in the British Journal of Management recognizes two main types of serial entrepreneurs:
- Opportunist serial venturers: This category of serial entrepreneurs is comprised of entrepreneurs often on the lookout for more business opportunities, especially after the success of the first. They include:
- Group developers or organic serials.
- Group creators or serial deal makers.
- Defensive serial entrepreneurs (venture repeaters): Serial entrepreneurs in this category are often reactive, usually undertaking a second venture because there are fewer apparent alternatives. Here, an entrepreneur whose initial business was a buyout comes back to buy part or all of it, often due to loyalty to the company.
Across these types of serial entrepreneurs, you are bound to find some common serial entrepreneur personalities, such as:
- Persistence: For the serial entrepreneur, market shifts are no cause for jitters. They see problems as opportunities for growth.
- Innovation: Brainstorming ideas and innovating are a never-ending process. They believe that there is always a better way to do things.
- Adaptability: They will always aim to find new ways to address prevailing problems. They are those who adapt quickly to things like lockdowns by moving their operations online or hybrid with the help of virtual offices.
- Resilience: Even when they lose it all in a venture, serial entrepreneurs never lose the entrepreneurial spirit that pushes them to get up and going.
- Strong drive for success: They always push further to ensure the success of their ventures, even if it means partnering or making deals with others or hiring advanced professionals to undertake some managerial roles.
- Risk tolerance: Entrepreneurs are traditionally known for taking risks. Serial entrepreneurs take things up a notch by embracing risks across multiple businesses. They get accustomed to risks to the point that risks are mere blurry lines in a market report. If there is a chance at success, they are taking it.
These personalities are primary impact drivers pushing entrepreneurs to move from one business to the next. If you observe very successful serial entrepreneurs, you’ll see how these personalities blend into various winning traits.
Traits of Successful Serial Entrepreneurs
Some serial entrepreneurs have been around for decades and don’t have much to show for it.
Then there are those whose profiles are filled to the brim with success stories. What are the characteristics that keep these successful serial entrepreneurs ticking?
Innovation and Creativity
Serial entrepreneurs constantly seek new business ideas and solutions to problems, leveraging their creativity to launch successful ventures.
For successful serial entrepreneurs, idea hunting is a continuous process. They consider every idea worth a second thought.
To better grasp how successful serial entrepreneurs perceive innovation and creativity, let’s look at Sarah Jane Thomson.
Her first venture was Ebiquity, a media monitoring and consultancy firm launched in 1997.
She found the idea for the firm in the strangest place: a dream. You read right, a dream.
Back to the real world, she gave the dream/idea a second thought and more thoughts and finally tested it out with her husband during her maternity leave.
The firm rose to be a multimillion-dollar company, and she has since launched four additional ventures, including First News, Priority One, ThreatAware, and Discover.Film.
Successful serial entrepreneurs like Sarah tap into a mix of innovation and creativity to constantly develop new ideas and practical solutions, ensuring that their customers and clients always get value for their patronage.
Adaptability and Time Management
One cannot overemphasize the importance of being adaptable to changing market conditions and managing time effectively to juggle multiple businesses.
Considering that launching and/or running multiple businesses comes with inherent uncertainties and risks, adaptability and time management are paramount traits for serial entrepreneurs.
Serial entrepreneurs are adept at quickly assessing these risks and uncertainties and adapting to them in a timely manner. This adaptability empowers serial entrepreneurs to pivot quickly and maintain their positions as industry leaders when the dust settles.
Risk Tolerance and Resilience
Taking risks is an integral part of the entrepreneurial lifestyle. Resilience is the cushion that protects entrepreneurs from giving up when risky ventures result in losses and failures.
Risks may be financial, reputational, bankruptcy, economic, and environmental.
As daunting as these risks may be in the context of running one business, serial entrepreneurs are not entirely fazed by the idea of facing them across multiple businesses.
Therefore, it is not unusual to find that many successful serial entrepreneurs have high-risk tolerance and are resilient enough to handle failure on multiple fronts and still bounce back.
Take Jeff Bezos, for instance. In the early years of Amazon, he recognized that the company had a 70% chance of bankruptcy or failing, but that didn’t stop him. He informed the investors of the likelihood of losing all their investments and still went ahead with it despite the risks, according to Academy of Achievement.
Today, Amazon stands as an epitome of various success stories in a field of far too many failures. Jeff’s resilience keeps the company bouncing back from the many failures of its over 100 subsidiaries.
Networking and Leadership
Serial entrepreneurs tend to be good networkers and team builders, leveraging their leadership traits and charisma to keep important individuals and organizations within arm’s reach.
If it will get them what they need, they will place their expertise, ideas, exclusive data, money, and connections on the table. Similarly, they won’t hesitate to leverage similar offers from others.
For the serial entrepreneur, networking is a force multiplier that hastens business growth. Therefore, it is one of those traits of a serial entrepreneur that you must learn to ensure business ventures and startup success.
Strengthened by excellent leadership qualities, successful serial entrepreneurs are able to communicate their dreams and visions in a manner that effortlessly persuades people in their network, including employees and team members, to key into their business ideas. This translates to valuable support for the entrepreneur’s ventures.
Challenges Faced by Serial Entrepreneurs
These entrepreneurial traits, characteristics, and mindsets prepare serial entrepreneurs to face some common challenges, including:
- Work-life balance: Juggling multiple businesses at a time is a recipe for burnout, poor social life, and all the nasty things that come with them. To keep things in check, serial entrepreneurs leverage their time management and leadership skills to delegate roles and tasks to others while overseeing things from a managerial standpoint.
That’s how Sir Richard Branson is able to manage a company that controls over 400 companies and still have time to go powerboat racing and hot-air ballooning.
- High risk: Risks are considered a core of entrepreneurship. Because entrepreneurship usually involves navigating uncharted territories, entrepreneurs are often faced with high levels of risk without a solid reference point on how to handle them. For the serial entrepreneur, high risks come in multiples. So much so that there are assumptions that serial entrepreneurs are addicted to and love risk-taking.
Take Elon Musk, for instance. His ventures, which are worth billions today, are products of taking incredibly high risks. Yet, he insists he doesn’t like taking risks and has been quoted as saying, “I feel fear quite strongly.” Still, he’s known for having high-risk tolerance and would embark on any venture he considers important enough, even if the odds are not in his favor. He comes out mostly unscathed because:
- He and his teams conduct extensive market research and develop practical strategies for development and market penetration, even when the odds are low.
- He believes that failure is an option and is not afraid to fail. According to Elon Musk, “If things are not failing, you are not innovating enough.”
- Financial management: If you’ve ever managed a business, even if it’s a small storefront, you’d know that managing finances is not easy. Now, imagine doing so for multiple businesses with high potential. It doesn’t matter that they are sometimes backed by investors, serial entrepreneurs often have to put their skin in the game to ensure that a venture breaks even and yields returns for investors.
To keep bankruptcy and other financial risks at bay, serial entrepreneurs lean towards training and mentorships to sharpen their financial acumen. More importantly, they learn to separate their personal finances from their business and invest heavily on accounting software and experts to keep their books in order.
- Market adaptation: The market waits for nobody, not even billionaire serial entrepreneurs. Jeff Bezos has lots of failed products to show for that. Unstable economies and market fluctuations are a serial entrepreneur’s nightmare. You could have a good product that generates all the buzz today, only for a market shift to nullify its utility and relevance the following day, sending years of hard work down the drain.
Hence, serial entrepreneurs know to and do invest in continuous market research to forecast future consumer demands and improve their products or create new ones to retain relevance. This keeps them super agile and better prepared to proactively handle market challenges.
Success Stories of Serial Entrepreneurs
Some entrepreneurs have made their mark as some of the world’s top serial entrepreneurs. Their entrepreneurial success stories stand as inspiring serial entrepreneurship for individuals who have started their entrepreneurial journey and anyone on the path to becoming a serial entrepreneur.
Think of successful serial entrepreneurs like:
Elon Musk
Arguably the world’s most successful serial entrepreneur, who also moonlights as the world’s richest man. Elon Musk is the brain behind a bunch of multibillion-dollar companies.
When it comes to launching businesses, he maintains a straightforward approach. At a roundtable session at FCO in 2012, he said, “I don’t create companies for the sake of creating companies, but to get things done. I have to get other people involved, otherwise it would be just me.”
This principle can be seen in how Elon Musk has leveraged networks and leadership to create some of the most innovative companies currently on the face of the planet.
Elon’s journey to becoming a serial entrepreneur started as far back as when he was 10 years old, learning to program and creating Blastar, a game he sold for $500 when he was 12, according to Yahoo Finance.
Twelve years later, he co-founded Zip2 with Greg Kouri and Kimbal Musk. Zip2 was basically a virtual Yellow Pages. Five years later, the company was sold to Compaq Computers for $307 million in cash and $34 million in stock options.
With the proceeds from the buyout, he created X.com (not the Twitter you now know). Down the line, he merged X.com with Confinity, to create PayPal.
Although he was later ousted from PayPal, he maintained his equity stake in the company and cashed out upwards of $175 million when eBay acquired PayPal, according to Investopedia.
Armed with lots of money and an innovative, risk-taking head on his shoulders, he split the money into three companies:
- SpaceX – $100 million. Company currently valued at $200 billion.
- Tesla Inc – $70 million. Company currently valued at $792 billion.
- SolarCity – $10 million. Company acquired by Tesla in 2016, a deal worth $2.6 billion.
At the time he was making all these investments and juggling the development of these businesses, he was borrowing money to pay his rent.
Elon Musk is now also at the helm of other multibillion-dollar firms, including Boring Co., X (formerly Twitter), and Neuralink.
Oprah Winfrey
With a net worth of $2.8 billion, Oprah Winfrey is a self-made billionaire and the richest black woman in the world. You might know her from The Oprah Winfrey Show, but she’s done many other things.
Her journey to becoming a serial entrepreneur started in adolescence when she landed her first hosting job at 18. A path she stayed on, identifying and engaging various hosting opportunities until, thanks to a push from her network, she negotiated ownership rights to The Oprah Winfrey Show and started her own production company, “Harpo.” Consequently, she became a millionaire at 32.
From there, her entrepreneurial journey was forward ever, breaking different records along her path:
- She’s the first black American woman to own a production company.
- She has 46 Emmy Awards to her name.
- She was once the highest-paid TV star in the world.
- Hitting the $1 billion mark in 2003 made her the first black female billionaire.
In addition to hosting talk shows, Oprah Winfrey is a television producer, author, and actress. She has multiple businesses and projects to her name, including:
- Harpo, enveloping O, The Oprah Magazine, Harpo Radio, and the Oprah Winfrey Network (OWN)
- Oprah.com, a website Oprah uses to promote the things she loves, such as healthy eating and reading.
- Weight Watchers (WW International), a company that focuses on supporting sustainable weight loss
- True Food Kitchen, a restaurant chain focused on making healthy eating more available and accessible.
- Maven Clinic, an online platform focusing on fertility, pregnancy, and parenting.
- Oatley, a Swedish oat milk company
- Oprah Winfrey Homes, a real estate venture.
From childhood to adulthood, Oprah’s story has been one of resilience and a remarkable display of leadership and creativity.
Sir Richard Branson
Richard Branson’s entrepreneurial journey is one of the most outstanding examples of serial entrepreneurship ever.
His story is also one that’s best kept short or told in a full-length novel, so we’ll keep it short here.
With a very high risk tolerance, Richard Branson is one of the most daring entrepreneurs you’ll meet. This trait is evident in not just his business practices but also his general outlook on life.
His entrepreneurial business ventures span various fields, including wireless communications, radio stations, hotels, space tourism, hotels, record labels, radio stations, health clubs, finance, renewable energy, car racing, and megastores, among others.
At 15, he started his journey with a student magazine, which sold over $7,000 in advertising within the first year. Three years later, he abandoned ship and established the Virgin brand with the launch of Virgin Mail Order and Virgin Records a year later.
From there, Richard Branson was simply unstoppable. It was just him going from one venture to the next and to the next…and to the next!
According to him, “Frustration can be an enormous driver of change, if you are good at spotting the opportunity sitting right at the center of a problem.”
One could say that Richard Branson has been an incredibly frustrated individual because he’s spotted opportunities that have led the Virgin Group to birth 40 primary companies, which in turn controls more than 400 companies worldwide, according to Leaders.
Sir Richard Branson embodies every entrepreneurial trait you would expect of a serial entrepreneur.
Other Noteworthy Serial Entrepreneurs
Steve Jobs
Steve Jobs co-founded Apple in 1976 but was forcibly removed from the company in 1985. Troubled but resilient, he went ahead and launched NeXT in the same year, releasing the NeXT computer in 1988.
While juggling the various aspects of developing NeXT products, including NeXTstation and NeXTcube, he also recognized some great opportunities in Pixar. He invested $5 million in cash as capital, bought its technology rights for an additional $5 million, and became the chairman of Pixar.
Following his success with Pixar, he was brought back to Apple in 1997. At the time, Apple was struggling. Steve Jobs’ leadership, innovation, and creativity revived Apple and kickstarted the smartphone revolution. The rest, as they say, is history.
Andreas von Bechtolsheim
Andreas is better known for co-founding Sun Microsystems in 1982, which he nurtured into a multi-billion-dollar business. He was also one of the earliest investors in Google; took the high risk of writing out a check for $100,000 to Sergey and Larry, before Google was even established as a company.
Back to his own ventures, from Sun Microsystems he left to start Granite Systems in 1995, which he sold to Cisco Systems for $220 million within its first year. In 2001, he launched Kealia, a server technology company which he sold to Sun Microsystems and got himself back in Sun’s management team.
He also founded Arista Networks, Open Compute Project, and HighBar Ventures, through which he has invested in many tech startups.
Wrapping Up: Serial Entrepreneurs
It’s more comforting to assume that billionaire serial entrepreneurs were born wealthy and had lots of money at their disposal to kickstart their lives.
However, that’s not the case for all. Serial entrepreneurs like Steve Jobs, Jeff Bezos, and Andreas had regular middle-class childhoods. Oprah had it tough.
Further Reading:
- Technologies Powering Virtual Office Spaces
- Empowering Independence: A Guide for the Modern Independent Business Owner
- Maximizing Customer Value: A Guide to Customer Retention Analysis
- Green Marketing Definition: What It Is and How It Works
Their entrepreneurial mindsets were cultivated over time as they observed and learned from their environments and fields, identifying opportunities and creating innovative solutions and strategies for underserved markets.
With time, they became masters of various entrepreneurial characteristics and traits, from innovation and creativity to resilience, adaptability, leadership, and risk tolerance. This made them better-prepared to handle most entrepreneurship challenges by themselves or with support from their network.
As you embark on your entrepreneurial journey, consider having some moments of self-reflection to identify your entrepreneurial traits and those you need to improve on. Dig deeper into these serial entrepreneur success stories to surface more insights and inspirations.
Finally, leverage business growth tools, such as Alliance Virtual Offices services, to expedite your entrepreneurial success.
Learn more about Alliance Virtual Offices services and how they can help you establish a credible and professional business presence instantly across multiple locations.
