What makes serial entrepreneurs tick and what do they bring to the ecosystem

Entrepreneurs acquiesce that “no one in their right minds would choose to start up” as the “probability of making money and winning significantly keeps dropping”.

And yet, they choose to start up. They are willing to go through the grind, and put in blood, sweat, and tears. Most will work long hours, give up on their personal life, haggle with early customers, and pitch endlessly to investors… with a vision in mind. 

This may seem foolhardy to most, but entrepreneurs feel that slipping into the regular 9-to-5 grind is like a life sentence. 

What makes entrepreneurs think so differently?

The subject has been studied multiple times, including by Wayne Stewart, an associate professor at Clemson University in 2013. 

In an article that year, he wrote that research showed that serial or habitual entrepreneurs have been around since the Industrial Revolution. He added that over one-third of all ventures are initiated by serial entrepreneurs and have higher growth rates. 

For example, Facebook’s Dustin Moskovitz founded Asana while Amit Kleinberger, CEO of Frozen Yogurt, launched three startup-to-IPO ventures. 

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What drives these entrepreneurs?

Alex Peter, Co-founder and CEO, The Quartile Company, says, “Serial entrepreneurs are a rare breed of individuals who are fearless about taking the leap of faith (for the second time) and making things happen. If you take a step back and look at their lives, you notice something very interesting.

"These are individuals who have a lot to lose because of their previous exits, success stories, etc. Their success precedes them, which gives rise to doubts and performance based on others’ expectations, etc.” 

The reason some individuals choose to start up over and over again is the fact that they are driven by success, are high risk takers, and keen to do something unproven. 

As Mayank Bidwataka, a serial entrepreneur and Co-founder of Vokal and Koo, says, “It is a high that some want to experience again. They have already done this, and have experienced the joy of building something from scratch, reaching a certain scale, and even changing the lives of many people.” 

He adds that starting multiple times is about looking at achievement, innovation, and the ability to take risks over and over again. 

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Generating wealth

Research also shows that serial entrepreneurs have a strong focus on creating wealth and growing along with their product and company. This also makes them restless as individuals. 

Alex feels serial entrepreneurs have seen and dealt with the good, the bad, and the ugly. They have insights, ideas, and plans that are tried and tested. They have better ability to navigate through issues, experiment faster, and raise funds quickly.

“They have proven themselves to the market and to people - even if it is a failed venture, they have displayed the ability to build products, they understand operations, MVP, PMF, and GMT. This in turn brings in certain faith in the investors that the startup may show growth, create value, and succeed,” explains Sujeet Kumar, Co-founder of B2B ecommerce unicorn Udaan. 

Many second-time entrepreneurs are also angel investors and mentors. 

Sujeet himself has invested in startups like Vakilsearch and celebrity engagement platform Tring. Kunal Shah, Founder of Cred, earlier founded FreeCharge and has been an angel investor for a while now. 

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Creating jobs 

Research also shows that once the core hustle and building of products is done, these entrepreneurs are more likely to get bored with the daily decision-making and basic managerial role. They itch to build “the next big thing”. 

The operational experience that comes by working in such teams brings in a certain trust factor that makes it easier for them to hire talent, get funded, and even build the product.

With more companies being born, and more investment being pumped into the market, this translates into more jobs. 

“People are also willing to join you looking at your track record. This means more faith in the founders and startup ecosystem at large,” Sujeet says. 

These entrepreneurs end up refining their vision with time and experience. So, as the number of serial entrepreneurs keeps growing, the ecosystem evolves and grows along with it, meaning more jobs, funding, and talent in the market.