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January 21, 2025

The serial entrepreneur – what makes them tick

The serial entrepreneur

Richard Branson, Elon Musk, Bill Gates, Oprah Winfrey, Steve Jobs, Jeff Bezos. These icons are united by massive wealth and impressive legacies. They represent a unique breed of entrepreneurs who repeatedly build and lead multiple businesses, often across different industries, and achieve extraordinary success.

Unlike traditional entrepreneurs, who focus on a single company throughout their career, serial entrepreneurs thrive on the challenge of building, scaling and exiting businesses, constantly seeking new opportunities and innovations.

While it’s rare for serial entrepreneurs to reach to the legendary heights of Richard Branson, the factors that drive them are strikingly consistent. What defines this select band isn’t just their ability to spot opportunities – it’s their commitment to pursue them. This remarkable drive and mindset can offer valuable lessons for anyone seeking a more entrepreneurial mindset.

So, what makes these serial entrepreneurs tick?

Key character traits of serial entrepreneurs

Despite their unique backgrounds, experiences and aspirations, serial entrepreneurs tend to share two key character traits that drive their motivations.

Confidence

Launching a business is inherently risky, and doing it repeatedly requires savviness, grit and a strong stomach for risk. Studies suggest that entrepreneurs with low-risk aversion are likelier to be serial entrepreneurs and feel comfortable in a seemingly perpetual state of uncertainty. Some can compartmentalise it, many even enjoy it. But what this really boils down to is confidence. Serial entrepreneurs thrive in risky environments because they have confidence in their ability to find the solution. This confidence also means they can better recover from failure and are more likely to try again.

Curiosity

Serial entrepreneurs often display a boundless appetite for learning and figuring things out. Whether it’s acquiring technical knowledge, understanding market trends or delving into new industries, their curiosity drives them to constantly explore and innovate. While some entrepreneurs are content with a single successful business, serial entrepreneurs are perpetual learners and growers. They’re always asking, what’s next?

Key motivations among serial entrepreneurs

The desire to solve

“I don’t create companies for the sake of creating companies, but to get things done.” — Elon Musk.

Serial entrepreneurs tend to be natural disrupters and inherent problem solvers, constantly asking “How can this be done faster or better”. Instead of viewing obstacles as roadblocks, they see opportunities for innovation.

Their ventures often reflect a deep desire to address problems. Take serial entrepreneur Marc Lore, who has built and sold four businesses in 25 years. One of his first ventures, Diapers.com, addressed the needs of overwhelmed parents by offering fast delivery of diapers at competitive prices. The company was acquired by Amazon in 2011 for US$550 million. Later, he launched Jet.com, an e-commerce platform that optimised pricing and logistics to save customers money. Walmart purchased Jet.com in 2016 for US$3.3 billion. Two very different problems, both solved with innovative customer-centric solutions.

The drive to execute a plan

“It’s not about ideas. It’s about making ideas happen”, Scott Belsky, co-founder of Behance Inc

Serial entrepreneurs are dreamers with a plan. They don’t just have vision, they know how to execute it too – and they get a kick out of it. From the thrill of navigating challenges to orchestrating resources, they find satisfaction in taking abstract concepts and ideas and breaking them into actionable steps.

The satisfaction of solving problems and seeing the tangible impact of their work becomes addictive, too. Achieving successful outcomes offers validation and momentum, inspiring them to obsessively refine processes. Each milestone reflects their ability to make change happen. It’s this push to act, rather than just imagine, that fuels creation and reinvention.

For many serial entrepreneurs, a company loses its lustre after they’ve exited and sold to a major corporation. Working within slower-moving, hierarchical structures can quickly become frustrating, and the inability to implement solutions fast or drive change at the same pace they’re accustomed to, can feel stifling.

So, they move on to the next problem.

An insatiable appetite for growth

“Business opportunities are like buses — there’s always another one coming.” Richard Branson.

Serial entrepreneurs tend to be restless individuals with an insatiable need to grow, create and conquer. This growth mindset is rooted in their desire to continually challenge themselves and push boundaries.

Although money may not be the main goal, their wealth definitely plays a key role, allowing serial entrepreneurs to use the profits from one project to fund the next, dreaming bigger and taking bolder risks each time. For example, Elon Musk used proceeds from the sale of PayPal to fund Tesla, SpaceX, and SolarCity. Similarly, Richard Branson has leveraged the success of Virgin Records to enter industries as diverse as aviation and space tourism.

Regardless of whether a founder’s first business was a success or not, this drive for growth not only fuels their ambitions but also, according to some research, makes serial entrepreneurs more likely to succeed. According to recent data, repeat founders have consistently raised larger funding rounds from VCs across all stages of the startup lifecycle globally for more than a decade. Nearly half – 49% – of unicorn startup founders in the United States have previously started at least one company, rising to 65% in Europe.

Failure – better than not trying

“I knew that if I failed, I wouldn’t regret that, but I knew the one thing I might regret is not trying.” Jeff Bezos.

Most academic studies agree that setbacks along the way fuel rather than diminish serial entrepreneurs’ determination. Rather than causing them to shy away from further risk, missteps are seen as learning opportunities, which minimises the psychological impact of setbacks.

Some research has found that experienced entrepreneurs use failure to build “entrepreneurial capital,” which includes skills, knowledge and networks they can leverage in future ventures. In other words, it spurs them on.

Unlike novices, serial entrepreneurs show a greater capacity to learn from their mistakes, enabling them to enhance their strategies, improve their tactics, and increase their chances of success over time​.

Sara Blakely, founder of Spanx, openly discusses the role of failure in her journey. Growing up, her father would regularly ask her, “What did you fail at today?” This ingrained a mindset where failure wasn’t feared but embraced as part of growth. Similarly, Jeff Bezos has highlighted how Amazon’s failures, like the Fire Phone, paved the way for groundbreaking successes like AWS and Alexa. For these entrepreneurs, the willingness to try, fail, and learn is far more important than playing it safe.

Final words – the thrill of the unknown

Serial entrepreneurs aren’t deterred by uncertainty or the prospect of failure. In fact, it often motivates them. Each new venture presents a new challenge and represents an opportunity to step into the unknown, solve a problem and turn bold visions into transformative realities. Their ability to find clarity in chaos often leads them to tackle projects that others deem too risky or unconventional, whether it’s pioneering electric cars or disrupting traditional industries.

What makes serial entrepreneurs tick is not the destination, but the journey itself – the constant push to grow, create and conquer the next frontier. It’s the reason they keep coming back for more. Ultimately, it’s not just about achieving success, though this is undeniably addictive.