Gen Y and the Modern American Dream: When is the right time to found?

At Startup Institute, I meet tons of successful, sometimes failed, but always hopeful entrepreneurs on a daily basis. When the conversation inevitably turns towards work, in a crowd of (aspiring) entrepreneurs, I always ask, “So, what do you want to be doing?” About 80% of the time people will answer, “Well, I want to be a founder.”

Thinking about this, my mind started racing. I became curious about the question of the founder. I started to wonder, why does everyone want to be a founder? Is this is the modern American dream? Forget the white picket fence, let’s build a software company! Did they all go see The Social Network together and get mesmerized by the oozing sex appeal of an angsty, hoodie-wearing Jesse Eisenberg? Is this just part of my generation? Has everyone been bitten by the startup bug?

I dare you to try one Google search using the keywords “Gen Y” and “entrepreneurship.” You will inevitably find dozens of articles about how this generation, more than any previous, is more entrepreneurially-minded. In fact, Gen Y is almost two times more likely to major in entrepreneurial studies while and college, with the goal of starting their own business soon after. One study states that half of recent college graduates believe that being self-employed is more secure than having a full-time job. And why wouldn’t they? Let’s take a look at the some of the most successful companies of our time and their founders (hint: they all have something in common).

  • Microsoft: Bill Gates (20) & Paul Allen (22)
  • Google: Sergey Brin (25) & Larry Page (25)
  • Apple: Steve Jobs (21) & Steve Wozniak (26)
  • Facebook: Mark Zuckerberg (20)

Did you see the pattern? All of them were in their twenties when they founded their companies. Is it any wonder that this generation has such a fascination with the idea of technology, startups, and being your own boss?

But these companies are one in a million. What about your typical, everyday startup- how often do they succeed, and who are their founders? Dharmesh Shah provides some insight in his blog with some interesting facts and figures that point towards the exact opposite demographic of this fresh-faced twenty-something, Gen Y, go-getter. Here are some facts Dharmesh sites:

  • Average age of founders is 40
  • The majority of founders are serial entrepreneurs, with the average number of businesses launched of 2.3
  • 75.4% had worked as employees at other companies for more than six years before launching their own companies

So, what about this idea of age and time to found. Is now the time, or should you wait to have some more experience under your belt before taking the leap?

In truth, there may not be any one right time to found a company or join an early-stage team. The numbers seem to contradict themselves in the age dilemma. The numbers I’ve quoted don’t make it any clearer. And what’s worse- startups have ridiculously high failure rates, be it with young founders or old. So what’s the secret sauce? Ultimately, what it comes down to is you, the individual with your own careful combination of passion, grit, determination, experience, team, idea, market potential, and a myriad other things that make for a successful entrepreneur and startup.

So what about Gen Y- a group that, ironically, derives its uniqueness through their shared focus towards entrepreneurship? In the end, age doesn’t and shouldn’t matter, whether you’re twenty or sixty, you can be a founder. What the twenty-somethings of Gen Y have in advantage over others is that they have nothing to lose and everything to gain. With little expectation of a lifestyle to maintain, a fresh perspective, tons of energy, and a clear focus towards entrepreneurship, the twenty-somethings of Gen Y are poised to make a big splash on the startup ecosystem for years to come.


Kailey is Program Manager at Startup Institute. She is responsible for building relationships with partners of Startup Institute Boston. She enjoys connecting the most innovative companies in Boston with the amazing talent pool at SIB. Leading the charge on student engagement both inside and outside of the program to promote the unique SIB culture, Kailey ensures that students become integral members of the Boston startup community and tech ecosystem.

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