Fostering The Entrepreneurial Spirit With Stu McGowan, Entrepreneur OG

My dad, Stu McGowan, is the OG of entrepreneurs. He started his own video production company when he was still in college, ran that for 25 years and then totally switched gears and went into rehabbing houses about 10 years ago. For my entire life I’ve watched my dad work his ass off all day and night, creating two really successful businesses and raising seven kids along the way.


Five out of those seven kids are now working on some kind of independent business. Our businesses range from my brother Evan’s company BrandYourself to my brother Nick’s handyman business to my sister Lila’s tattoo parlor.


I recently came across an article by Tim Berry, president of Palo Alto Software Inc., about how his five kids are all entrepreneurs too and everyone is always asking him how he did it. He had two answers:


  1. He didn’t push his kids in any particular direction.
  2. He encouraged his kids to pursue an education for the sake of learning, not for the sake of preparing for a specific career.


I was curious to see if my dad agreed with what Berry had to say, so yesterday I called him repeatedly on FaceTime until he finally picked up and made him talk to me for a few minutes.

Here’s what he had to say about raising entrepreneurs and fostering the entrepreneurial spirit.


So the first thing Berry says is that you can’t push your kids in any particular direction.

That’s huge. That’s absolutely enormous. I learned that from my dad, of all people.


Really? How?

Because here’s my dad and he does this very specialized thing…


He had the coolest job his whole life [Ed note: he was a helicopter pilot], he loved what he did, and he never, ever made any inclination that I should do anything like follow in his footsteps and be a pilot, or anything else for that matter.



So that was something you felt like you wanted to do with us as well?

No, no the point is that most people do something similar to what their parents do: they’re professionals or they’re in the trades or whatever. It’s not very likely that someone is going to break out of what they grew up with.


I knew that and I never tried to put any aspirations on any of you guys. It was really important to me that you just grow up and figure it out and have a really strong base. In our family it couldn’t have been better because you got both. You had mom working 35 years at UVM and her job is professional and then me being an entrepreneur, but with steady income.


If your dad did that for you and you did that for us, do you think that’s evidence that not pushing your kid toward anything in particular fosters entrepreneurs?

I won’t say it fosters an entrepreneur but I think that living with the example of an entrepreneur in your family is pretty damn important.


I will say that if you push them in a particular direction, they’re more than likely to go in that direction. Even if you just guide them.


We sort of guided you but not really, like we guided you towards college. But we always said, “Try to find something you really want to do.”


I think we couldn’t have been a better example for you guys because you got to see two very different ways of putting the world together and you were able to make your choice. Mom never said, “I want you to work at the university, I want you to be a potter.” We were very, very careful about that.


So to me it doesn’t necessarily mean you’re going to be an entrepreneur but you definitely have more of an option.


The second thing Berry talked about was pursuing education for the sake of learning, not in preparation for a specific career.

Yeah, for mom that’s it. That’s why she’s still gets on Evan’s shit about not finishing college and she just won’t leave him alone. It’s become satire now with those two. She was 100% about that and I was a little bit more pragmatic.


Truthfully my pragmatism was probably [good]… I didn’t foresee the recession happening as badly as it did but I’ve been reading some stuff lately about this gigantic generation that’s exactly your age who went to college for learning instead of preparation and they’re all fucked right now. They are just part of the underclass and they’re going to be there for a long time.


Then do you think that statement isn’t quite true?

I’m not saying it’s not true, I’m saying it would be wonderful, in an ideal world for everybody to do that for their kids. I do believe that the thing that will be the most advantageous for anyone out there in the world right now is having the ability to think and having a liberal education. That’s what allows you to not just be an entrepreneur but also to be able to fit into corporations and small businesses that are being operated more and more like entrepreneurial businesses.


Being an entrepreneur is really being able to get past convention and being able to get past your own fear and safety and security. It’s not an easy thing to do, Em…


It’s very difficult. Imagine someone who has no example, has no nothing, even thinking that they can do that. They just can’t. Mostly they can’t do it.


Do you recommend raising kids to be entrepreneurs?

Well, that’s the thing. I think if you raise kids the way I think that guy did and certainly the way we did, the point is that you have possibilities. But that in and of itself is a difficult thing because… I know it will work out but it’s a hard, hard thing to know that you’ve created a situation for your kids where they’re going to have to potentially struggle and figure it out what they want to do.


For example, my friend from high school? His kids are going to be professionals. There’s no question that’s what they’re gonna do. They might be entrepreneurs, maybe, but they don’t have as much choice as you guys.


They’re gonna be okay. They’re gonna be in that class, that’s what they’re gonna be. But they’re also gonna be limited.


When you raise kids without limits in terms of what they can do in the world, that’s a great thing but on the other hand it’s a double edged sword. We’re sitting here watching all of you guys now in your twenties and thinking, “Oh boy… I hope it works. I hope it works.”


If what you do is raise your kids with open possibilities, yes. That in and of itself is an entrepreneurial way to raise kids: not to be entrepreneurial but to be able to have opportunity. Any opportunity.


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