For the first fifteen years of my career, I worked for other people. Sometimes it was fun. Sometimes it wasn't. Seven years ago, I started my first business and I've started three more since, along with a venture capital fund, a SuperPAC, a family foundation and this column.

Being an entrepreneur - even with all of the risk, stress and headaches that come with it - is almost always fun. And when you think about it, being an entrepreneur really means you call the shots, set the parameters, and execute your own ideas - how can that not be better than doing what someone else wants?

Becoming an entrepreneur was a step along the way of pursuing "happiness." And as a parent, when you ask me what I want most for my children, the answer is, predictably, "for them to be happy." So if being an entrepreneur makes me happy, and if my kids and I share at least some similar traits, then it stands to reason that I should give my kids the tools they'd need to become entrepreneurs too.

And that's where I run into trouble.

The tools for success

I can give my kids a good academic education by sending them to really good schools and making sure they're doing their homework, reading, and not watching tv or playing too many video games. I can give them a good cultural education through travel and exposure to lots of different activities and ideas. I can give them a good civic education by encouraging/ forcing them to volunteer, by participating in organized religion, and by being politically aware and engaged.

But it seems highly possible that none of this teaches them the skills they'd need as entrepreneurs need to take risks, ignore naysayers, get up off the carpet time and time again, and look at things differently.

In fact, by diligently giving them so much opportunity, exposure and support, I'm probably making it almost impossible for them to develop the skills they'd need if they wanted to be entrepreneurs too.

I'm a first generation American. We grew up upper middle class. It wasn't a hardscrabble life by any stretch of the imagination, but I definitely had to make my own way. When things went wrong (in a six year span, I worked for a Governor in Rod Blagojevich not long before he ended up with a 14-year jail sentence, followed by a job at Lehman Brothers right as they took down the global economy), it was on me to make them right.

I didn't have a trust fund or a network of friends from a private school to rely on. And while none of this remotely makes me Aldous Huxley, it did force me to be resilient. It forced me to confront - and get used to - conflict, rejection, and failure.

My kids will undoubtedly have a privileged childhood and be handed every advantage imaginable. Odds are, they'll go from prestigious private schools to prestigious colleges. And based on their personalities to date, it seems like they'll both be well-rounded, kind, compassionate, intelligent, thoughtful people.

But are they getting the skills and training they need to be successful entrepreneurs? Probably not. And would any parent in their right mind deny their children resources, opportunities and advantages just to make them tougher and more resilient? None that I know.

Raising a generation of entrepreneurs

Maybe raising a generation of entrepreneurs doesn't really matter. But if the fight over immigration policy and H1B visas is based, at least in part, around needing to import talent that we can't seem to grow here in the U.S., then from a public policy perspective, it does matter.

And if growing up privileged makes you less likely to develop the skills needed to become a successful entrepreneur and if developing new entrepreneurs does matter to our economy, then that's all the more reason to double down on providing all of the other skills that budding entrepreneurs in schools in working and middle class communities will need - technical skills like computer science but also a better sense of how business works, how ideas are developed, how you can think both analytically and creatively, how to listen, how to ask for help, how to be flexible (skills that are all too often ignored in favor of rote learning).

There are startups with new pedagogies and ideas like Altschool (one of our portfolio companies) and organizations like Girls Who Code (one of our clients) who are doggedly teaching skills like coding and programming to kids in underprivileged communities. So some seedlings of the necessary infrastructure are in place.

But if we're relying on today's elite students to become tomorrow's entrepreneurs, we're probably going to be disappointed. And if we think our public schools are good enough as is to teach the skills to kids who, by necessity, will have more of the inherent traits necessary to become entrepreneurs, we're sorely mistaken.

If America's place in a global economy is to outpace everyone else in ideas, creativity, engineering and human capital, we're not set up to maintain that role for long. Because the children of today's successful entrepreneurs are probably the last people we can count on to be tomorrow's risk takers.

And we're not doing nearly enough to help the nation's countless non-privileged children take the lead either. As a new world in Washington radically re-thinks immigration policy, tax policy and education policy, they should take this all into account.

If not, in ten or twenty years, we'll find ourselves scratching our heads, wondering what happened - and working for someone else.