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The Science And Psychology Behind What Drives Serial Entrepreneurs

By some counts, serial entrepreneurs are responsible for a third of all new businesses. Clemson management professor Wayne Stewart has studied their hearts and minds.

Ask any entrepreneur how much blood, sweat, tears (and soul) they’ve put into their startup, and you’d get an imprecise answer at best. The long hours, the lack of resources, the simultaneous product and customer-network building—not to mention fundraising—often make the venture a one-time enterprise.

For some, the slip into a steady gig feels less like success and more like a life sentence. They prefer to exit stage left and start all over again. You could chalk it up to them being driven by the "not enough" trap or the restless by-product of too much fragmentation and a dearth of even five minutes of stillness in our current business culture. But you’d only be partially correct.

Turns out that while the mind of the entrepreneur has been carefully picked by scientists who discovered they do think differently than managers, serial entrepreneurs haven’t been under such close scrutiny.

That surprises Wayne Stewart, associate professor of management at Clemson University. Stewart’s research shows that habitual entrepreneurs have been around since the beginning of the Industrial Revolution (any time between 1780 to 1840, depending on who you ask), and they are a noteworthy group.

"We’ve seen some evidence that one-third of all ventures are initiated by serial entrepreneurs," he tells Fast Company, "And that those ventures have higher growth." Think: Dustin Moskovitz who founder-hopped his way from Facebook to Asana; Amit Kleinberger of Menchie’s, and veteran of three startup-to-IPO ventures Phil Fernandez of Marketo.


Three things, says Stewart. Simply put:

They are more driven by success, more likely to take course of action that is uncertain, and to do something unproven.

Starting multiple ventures flexes these founders’ risk taking, achievement, and innovation muscles. Though men scored higher than women on the risk-taking trait, both genders had an equal drive to innovate and achieve, Stewart’s research found.


In addition to these three common characteristics, Stewart says serial entrepreneurs tend to have a pretty tight focus on creating wealth and developing personally along with their idea for a product or service. But they may also be restless.

"If you are going to end one venture and go to another, you’re [probably] bored once you are into a daily decision-making managerial role," says Stewart.

Serial entrepreneurs may also have the itch to keep honing their ideas, he says. "Some research suggests entrepreneurs refine their vision with experience," explains Stewart. Like Twitter’s Jack Dorsey (which evolved from Odeo podcasting to Twttr) the founder may be working on a business and doing ok but the experience offers them a way to see how their original idea can be chiseled (or pivoted entirely) and turned into a whole new business.


Another piece of the psychological puzzle of serial entrepreneurs that’s not been investigated yet is failure. Fast or slow, failure often pocks startups’ first years. How to deal with a setback may be unique to serial entrepreneurs.

When we talk about subject of failure, what we don’t do [is talk about] how individuals respond. I suspect serial entrepreneurs are much more tolerant of failure. They have a much more rugged sense of self. They are more likely to pick themselves up, dust themselves off and say: I’ve learned this, I’m still capable, so I’m going to go at it again.

Stewart’s working on a paper right now on a theme that’s intimately tied to trip-ups: core self evaluation. He describes it as a mental combo pack that pulls together how the individual sees themselves and their ability to handle different circumstances and their sense of internal control (or belief in fate) over what happens. Those who have a higher self concept, says Stewart, generally tend to be more aggressive.

His hunch—which he’s quick to point out is currently just a general working hypothesis—is that serial entrepreneurs have tougher skins than one-time founders. In the real world, multiple-venture founders such as Redbubble’s Martin Hosking are channeling their energy from previous catastrophes into successful new enterprises.


A study released last month from the University of Western Ontario suggests that serial entrepreneurs aren't always able to turn those lessons into successively better ventures. Following Americans who founded more than one venture over the course of up to 25 years, author Simon C. Parker found that the entrepreneurs' performance didn't improve in subsequent startups.

The findings show that serial entrepreneurs obtain temporary benefits from spells of venturing which eventually die away. This implies that venturing generates benefits that spill over from one venture into subsequent ones, and it can provide a rationale for public policies that encourage re-entries by entrepreneurs, even if those entrepreneurs performed poorly in their first ventures.

Setbacks are inevitable, whether this is the founder’s second company or sixteenth. Stewart believes that serial entrepreneurs may have a better innate ability to quiet the negative thoughts that might plague a less resilient soul with self doubt.

There are ways in which serial entrepreneurs tend to think about their belief in their ability to handle the startup, their belief of the desirability of the venture, launching, and making it successful. These belief systems are informed by experience. To the degree that they come back to those fundamental traits, serial entrepreneurs are more psychologically durable.

What do you think it takes to be a serial entrepreneur? Share your thoughts in the comments below.

[Image: Flickr user Nuruzzaman Babu]

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  • tammi swanson

    I have started several businesses and I believe the reason is that I'm passionately driven by a belief in my ideas. I know that only I can make those ideas turn into realities. I have learned that even without any start-up capital, the passion behind the idea somehow manifests the vision. My weaknesses are obvious to me at this point (the day to day mundane management) and I try very hard to focus on those, improving hopefully, those weaknesses.

  • Eugen Ilie

    I like to think that an entrepreneur is and will be someone that wants to create better things, solve a business problem and they love to OWN it. Nothing drives them more than knowing it will be something part of their legacy and they can change people's lives along the way. We also know how hard it is to take it all over again after you did something great. Nothing is like starting it up all over again. But it all comes down to getting the flywheel in motion, as Jim Collins well said in "Good to Great". 

  • Dr Dion Klein

    Great article.  Tenacity and resilience are part of the S.Es makeup.  Along with that they seem to refuse to take 'no' for an answer.  They will eventually find a person to say 'yes' (either for funding, securing a sale, etc.)  

  • Lydia Dishman

    That's a great point about not taking 'no' for an answer. I think that falls under the resilience part of their brains, the thinking "if at first you don't succeed..."

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  • Warren Ritter

      Entrepreneurship and entrepreneurial start up opportunities first and foremost require enthusiasm and that's contagious. It fosters vision, creative thinking and creative action. It invigorates and inspires oneself, partners, customers, employee's etc.  It's out of the box. I hate that expression. One can't think out of the box. Something out of the box must think about them. And enthusiasm attracts such influence. It's actually very spiritual and fosters a visceral experience and invigorating days. Set backs are not things to be endured but challenges and opportunities in the mind of the entrepreneurial thinker and it's a rush. Just like a breakthrough. They have a vision and standing in it, they know things will come around. At the end of the day, week, quarter, one can reflect back upon it and see the results in way's that a hyper metrics based position in a traditional environment mutes ... and there can be a lot of money to be made, but I think more than that, and "that" is important, is it's lively. Living in a vision and taking action from that vision is ... enthusiastic living ... at least in the area of work life.

  • Lydia Dishman

    Thanks for taking the time to add your thoughts to this thread Warren. I agree, enthusiasm is necessary and can be contagious. A lot of the VC and angel investors I've spoken to tell me that the founder's passion for a project is often a big reason for them to invest.

  • Laturb

    I'm not sure that I necessarily fit the mould precisely of a serial entrepreneur, but I've started many companies that often fail. 
    If I'm impartially objective (if that's possible), my problem is that I see opportunity everywhere, and that can be a problem as the excitement of having discovered yet another route that satisfies my opportunistic character tends to distort the vision that I have for what I am already doing.
    However, to deal with the 'honeybee' part of my brain, I've forced myself not to take advantage of yet another great idea, and try and concentrate on the job in hand. That unfortunately, doesn't stop me from from dreaming and formulating what I think I a missing though.
    Finally, another aspect of my business character is that I have never chased money. It's more about evolving the idea into a success, which is really the reason why I get up in the morning.

  • Lydia Dishman

    Thanks so much for sharing your thoughts Laturb. I like the idea of a "honeybee" brain. Pulling focus is a challenge for many entrepreneurs, both serial and single venture, alike.