Gen X vs. Gen Y entrepreneurs

August 6, 2010

making moves

Matt Wilson, co-founder of, is a digital marketing strategist at Shadow Concepts LLC. Follow him on Twitter as he urges people to start businesses they are passionate about. This is part of the kickoff to a series on social entrepreneurship. The views expressed are his own.

When it comes to starting a business there are advantages and disadvantages to taking the leap at various points during your lifetime and there are distinct differences between entrepreneurs from different generations.

Gen Y entrepreneurs, also referred to as “millennials,” are famous for their .com start-ups like Facebook and College Humor, but equally as infamous for their entitled attitudes and over-exuberance. These young entrepreneurs are fresh out of school (some because they’ve dropped out all together) and have decided to take the world by storm, with or without their parents support. For millennials there is little to lose: no mortgages, no families, and not a whole lot of obligations. Besides, if you find yourself unemployed, ski towns out west are always hiring. Try doing that when you’re 36.

The generation born after the baby boomers knows better than that. Gen X entrepreneurs aren’t looking to risk it all on a roll of the dice. Instead, their business plans are much more thought out, not just to impress investors, but also to prove to their spouses and families that dropping half of the dual-family income will work out in the long run. Entrepreneurs at this stage in their life have a lot more to lose and the opportunity cost of the salary they’ve been accustomed to will weigh heavily on their minds.

Fed up with their 9-5 job and tired of being pushed around working for someone else, Gen Xers have been saving for the opportunity to start their own company. Which means they often they have their own capital to start with and can also look for funding from friends who trust their track record. Whereas Gen Yers look to start businesses on a shoestring budget or look to their parents for start-up capital.

Millennials aren’t concerned with their non-existent track records, either, which is part of the reason why they catch flack for being a bit arrogant. They are sick of their elders saying: “You can’t possibly know business if you’re under 30.”

Author and founder of RainmakerThinking, Bruce Tulgan, put the generational divide into perspective:

Here’s the short story about Generation Y: If you liked Generation X, you’re going to love Generation Y, because they’re like Generation X on fast forward with self-esteem on steroids. And they’re going to be the highest performing workforce in the history of the world. These entrepreneurs run on pure passion. They’ve learned a lot from their parents and have always been told they could do anything in the world.

Furthermore, millennials have a much easier time finding mentors and help for their small businesses. Colleges and universities have entrepreneurship programs or access to incubators and organizations like the Collegiate Entrepreneurs’ Organization. And baby boomer business leaders love to extend a helping hand to young people. Gen Xers have the work experience, have taken time to learn a trade or an industry and have working relationships with people who will be able to accelerate their progress. One of the best ways to find a business idea is to find a new niche in an industry you’ve been working in for years.

Regardless of your experience level or generation, it will be entrepreneurs that will lead us out of the recession. Who would you bet on: Gen X or Gen Y?


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This article says nothing, let alone proves anything. As great as facebook is, it’s really not producing anything let alone creating many jobs. And “college humor”, give me a break.

And what happens when the snarky, self-entitled 20 something’s fall flat on their face? Who are they going to cry to/get help from then when their parents’ retirement funds have been too beaten down to help them out? Furthermore, what happens when they find out all the b.s. their parents fed them about being so great, and so special is nothing but, b.s.?

At-any-rate, until my generation (Y) starts coming up with real ideas, real solutions, and real products that create real jobs/wealth I’ll won’t hold my breath.

The real question is do they (gen Y) have the resilience to bounce back after they come face to face with something they never dreamed of, let alone experienced in their lives’- failure and poverty? After-all, it was my understanding that at least 50% of start-ups fail. Grim reality is an x-factor that no bright-eyed member of generation (Y) is prepared for mentally, emotionally, or financially.

Posted by skomalley | Report as abusive

I don’t really see how they can have any sense of what’s right and what’s wrong in the business world at that age. Sorry, there more to creating a business than jumping the shark in your underware.

Posted by lkline | Report as abusive

There are many important differences between GenX and Millennial entrepreneurs, even if you compare them at the same points in their development (e.g., the young GenX dotcom entrepreneurs of the 1990s). Millennial entrepreneurship is also a global phenomenon, and the characteristics that make them successful in the US are also quite hopeful in emerging economies.

Posted by robsalk | Report as abusive

i’m from GenX (born 1967) and i didn’t wait for anyone to give me my identity either. i graduated college in 1991 during that recession and immediately set out to be my own business, and sell my talent to others on my own terms. so far it’s worked. glad to hear that the kids are ready to take over. i want the kids to know that we’ve been waiting for you to come of age for a long time. you’re going to be implementing the new world that we collectively create. we’ll be behind you. just treat us well please. we’re all doing this together. the people of the future will be grateful for the cooperation with which we hand them an amazing new world.

Posted by telyawot2 | Report as abusive

My money is on Gen-Y. Not only because I am part of this generation, but because there are still so many untapped niche markets left to be discovered that being under 30 is a definite advantage. We have nothing but time to try, fail, and try again until we start making money doing something we love.

Posted by Roy_Roca | Report as abusive

Glorified teenagers don’t have a clue — just mystical ideas that are opposite old hippy ideas, but just as useless.
The generation referred to in this opinion are a bunch of theorists who think they know it all, but don’t even know how to mow a lawn.

Posted by RudyHaugeneder | Report as abusive

It’s really not a matter of Gen X or Gen Y – market dynamics will push the winners to the top.

What the question should be is: what resources can, should and are we providing to these rockstars both at home and in the classroom? Access to resources (knowledge, mentors, capital) makes 80% of the difference.

These days, most educational institutions revolve around tests and theory; with very little practical application. Theory does not drive a knowledge-based economy, practical application does. This is why we see growing support for science and technology magnet schools. As a society we are obsessed with test scores and GPA.

Entrepreneurship is not an easily quantifiable graded metric, but it is the fundamental underpinning of our economy.

Best regards,


Posted by GaryWhitehill | Report as abusive

Does this apply to the under 30 crowd living with mom and dad because they can’t find a job?

Posted by BB1978 | Report as abusive

Let me say that I have had the chance to talk to these guys and they are nothing but professional.

There is no-more 9-5. People are much more educated now in a sense that technology has sped up the learning curve. Things are done faster and more efficient.

On the contrary, I feel it IS necessary to “pay your dos,” which I am sure these guys are more than willing to do.

I wish them the best and I think they are spearheading a new generation.

Posted by mikearone | Report as abusive

I’m a Gen-X entrepreneur. Had the nest egg to get it going, going gone. Now that it is gone and I really have not more than bullocks I am truly optimistic about my prospects for the future. I no longer have but one channel of income but several. All are showing growing revenues and profits, meager as they may be or they are showing growth in concept and supporting technologies.

I no longer focus on all the planning activities that are recommended in the blogosphere, incubators, and entrepreneurship programs. They are like training programs. But they do not drive revenue or deliver the service. And the day is just too short to not get to cash.

The best training is to do it even if it means losing your bank roll. The very nature of entrepreneurship suggests this is more likely the outcome. And in fact to anyone who has not resolved their fear of financial insecurity surrounding startups should just keep slinging the resumes.

In the meantime, I just do my business; some of it for present day income, and some of it for the big hit low probability of success high risk income.

Posted by mudduckk | Report as abusive

I don’t want to dive into the Gen Y/X discussion, but rather just make 2 points:

1) Matt Wilson (author of this post) is The Man. He has been a mentor and good friend to me and I have enjoyed looking up to him while he figures out his way more and more as a young entrepreneur.

2) I want to refute what the first commenter “skomalley” said: “As great as facebook is, it’s really not producing anything let alone creating many jobs.”
Okay, no offense but this is high quality ignorance right here. Facebook isn’t producing anything, or creating many jobs? You’re kidding around, right? They have over 1,300 employees. That’s no small feat for a company started just 5 years ago. And “not producing anything”? How about their “Open Graph” initiative ( ngraph), arguably one of the widest reaching and ambitious projects of any technology company in recent memory?
If you need any more evidence to reveal just how absurd the point that ‘Facebook isn’t producing anything’ is, just read Michael Arrington’s post “The Age of Facebook” from a few months ago: -of-facebook/
Arrington is one of the most respected/influential people in technology, and he compares Facebook to Google and predicts that in the next decade, Facebook will have as much (if not more) success as Google.

Posted by JohnExley | Report as abusive

I am a GEN X (1973) Entrepreneur and GEN Y has nothing, absolutely NOTHING on us OR our Baby Boomer parents! We started it all! We created it all! We built it all! We suffered it all! We carried it all! We fought it all! We outlasted (and still outlasting) it all! We GEN Xers and B-Boomers, man, we are SURVIVORS! Our parents had to survive and they taught us how to survive and we took it and thrived. Even in failure and setbacks, we — GEN Xers are relentless, persistent and invincible. Because we were raised with CORE VALUES, CORE BELIEFS it drove us (it continues to drive us) to withstand every temptation to give up, sell out, quit and fail. GEN Y are pathetic! These kids had everything with a “touch of the button.” No, we still had to figure out how to put a RECORD on the HI-FI, not how to cruise the Web on VIA WI-FI. TV did not play all night because it went off at midnight. We created all the cool, slick dance moves these kids do! Our parents and WE created all the timeless music that these GEN Yers just keep sampling, rehashing, reworking and rewarming over and over and over. GEN Y are not CREATIVE. You CREATE out of “lack” out of “survival.” When you are “handed” and “entitled” you simply REUSE, RECYCLE and REDEFINE. I am glad to be a GEN Xer and extra glad to have come from B-Boomers! I am glad that I am an ENTREPRENEUR so that I will NOT have to work for a GEN Yer and perhaps can hire them and teach them — what they lack — Real business, real work ethic, real life.

Posted by LPATWILLFILM | Report as abusive