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5 Tips on Raising Kids to Be Entrepreneurs

Tim Berry
Tim Berry
Apr 14, 2015 · 5 min read

I’m an entrepreneur, founder of Palo Alto Software. My wife and I are parents of five grown-up children, all involved with startups (Curious? check out Palo Alto Software, Rebelmouse, and HavePresence.) Does this just “happen” by osmosis, or did my wife and I do something specific to create it? Was it a good idea? And would I recommend other people do the same thing?

First, I should admit, we really didn’t plan it that way. I fell into entrepreneurship not because I believed in it in principle, but rather because I wanted to do what interested me and earn enough money to support the family. That became a software business in the heart of the Silicon Valley during the first PC boom; I was an entrepreneur with a Stanford MBA degree. And we never thought about raising entrepreneurs, just healthy, well-educated, happy, productive people.

So what happened? Have I learned anything about this that might help you? I’ve talked to my wife about it, as a reality check. And here’s what we think we’ve discovered, five pieces of advice for you as a parent:

1. Let them study what they want, not what you want

My wife and I believe in education. Period. Note we don’t say “business education”; I know just as many entrepreneurs with liberal arts degrees as those with business or technical degrees. So don’t push your kids into courses that promise to be the “hot fields” where opportunity exists — unless they’re already interested in one of those fields. Even then, by the time they’re out of school, the business landscape will shift several times, and what’s “hot” now will almost certainly have cooled down by tomorrow. Let them immerse themselves in learning they enjoy, subjects that already hold their interest, and they’ll find the way to learn what they need to succeed.

Of course, this approach to school pertains to higher education, not Mrs. Johnson’s fourth-grade reading class (basics are still basics)! Furthermore, I strongly disagree with the idea that kids be encouraged to just slide through school simply because a selected few of the richest entrepreneurs out there were dropouts. A handful of true giants in business lack a lot of “conventional” education, true — but for every one of them, there are a few hundred thousand others who’ve stayed the course and have the degree. Life, not to mention work, is just simpler with an education.

We practiced what I’m preaching here. We encouraged our kids to study whatever they wanted to study; but we also encouraged them to get all the way to the degree, and to study hard. All of them have college degrees now, two of them have grad degrees, and none of them studied business or entrepreneurship. Liberal arts was fine with us (not surprising, I suppose, since I’m a liberal-arts-first guy who started a software company).

2. Reject gender stereotypes

If your daughter loves tech, math, and science, let her study as much of it as she can handle. If your son loves art, music, or philosophy, don’t wonder if his brain just isn’t “sharp enough” for the nitty-gritty of “real life.” Stereotyping in either direction is unacceptable; don’t do it, and don’t accept it from others.

3. Don’t push

Resist the temptation to program your kids to enter any specific occupation, and especially don’t pressure them with expectations of following in your footsteps. If you invest the time and energy to encourage your kids in terms of being educated, don’t nullify all that effort by trying to shoehorn them into your own picture of what they should grow up to be. They’re supposed to do what they want, remember? Not what you want. Or are we still in the 19th century — when it didn’t work that well, either?

Doubt this? Try this trivia question: name a major movie in which a central character was supposed to go into his or her parents’ business but didn’t. Answer: tons, because this is more than a cliché: it’s an archetype. Kids have been doing this for thousands of years: witness Abraham trashing his dad’s store in the Bible! Come to think about it…Jesus didn’t end up a carpenter, either. In The Godfather, Don Corleone wanted Michael to be a senator, not the next don. And for a more recent example, take Hiro in Heroes.

Sure, it’s okay to hope they’ll want to get involved. It’s okay to dream. It’s okay to make some tentative plans to hand things off when the time comes. Maybe they will love what you do and want to do it, too. But freedom to choose is essential. Working in the business has to be their choice, not yours.

4. Trash the rose-colored glasses

We lived in a culture that gives trophies to every kid on the team, and redefines every defeat as a victory. We may have been helicopter parents on occasion (especially with our younger ones), but we didn’t try to protect them from reality either. We didn’t pretend they always won. Lemons happen, but lemonade isn’t always realistic, and they learned that. And some of the best ideas entrepreneurs ever get come from trying one thing, and then another, and then a third, until one “clicks” and they take off.

In our case, I’m not saying we were wise, or smart; maybe just lucky; and maybe even chronically broke, during all those years we were struggling with Palo Alto Software before it finally took off. Even if we might have wanted to wrap cocoons around our kids and buffer them from disappointment, trying, and struggle, it’s hard to actually do that when you’re bootstrapping a startup. All of our kids had to do their own homework and buckle down on occasion to do the hard things that came up.

5. Live your life, not theirs

Be an accidental, unintentional, role model. Let them see you enjoy your work when you do; and don’t pretend when you don’t. Show them where the money comes from, how your business works, how you grow it and adapt it. Let them participate in some of the details. Let them see you (and your spouse, if your spouse is so inclined) working the business goals, having realistic expectations, and dealing with setbacks. Let them see you as you are with what you do — and know it’s not the end of the world when things go wrong. From this, they’ll absorb something better than false “self-esteem”: they’ll know that it’s okay to try new things, it’s okay to experiment, and it’s okay if they don’t hit ultimate “pay dirt” the first time. They’ll still survive, and so will their parents!

People don’t always find their best place right away. Sometimes it takes one or two (or a dozen) false starts on the way to hitting one’s stride and finding the perfect fit. So don’t push your kids into corners. Let them work where they want, with whom they want, on what they want; let them learn by doing, and even learn by failing.

Entrepreneurship isn’t necessarily a better way of life than any other, but when it works, it’s a great way to work…and live. Bottom line? In the best of all possible worlds, you’ll end up with well-educated, hardworking people who know where your business came from, and why, and have a good understanding of that when they figure out where they want their lives to go. And they’ll have what they need to go there.

Originally published at

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