Answer by Jonathan Brill, Startup Specialist, on Quora

As a guy who exclusively works for tech startups, I have had a unique opportunity to observe a bunch of entrepreneurs in action. Some of them were more successful than others, and I’d say some of them wore it better than others.

With some of them, you could see it was very difficult. Maybe they spent their whole career doing middle management jobs in big companies and got to a point where they felt like they just had to do their own thing, or the money was too good. Those folks tended to really have a hard time with it. Some of the others though, they were like a fish in water. Here’s what I’ve noticed about those ones:

Working for someone else felt very unnatural, and made them unhappy to the point where doing their own thing was inevitable. The best founders I’ve worked for never thought about the risk of entrepreneurship versus the alternative because the alternative was never viable. I always think of this as the Jobs vs. Wozniak comparison. From reading the history, it seems Woz just wasn’t comfortable with the idea of so much risk and volatility; it took forever to pry him out of his corporate gig and he went right back as soon as he got the chance.

I don’t know that I want to raise my kid in a way so that they’d be unhappy if they had to do time in corporate America, but I think it’s constructive to raise them in a way so that they aren’t satisfied with hammering at the same nail every day. I’ve taken pains to start my kids on a path where they’re not going to go through a traditional education, they’re not going to be bound by traditional expectations of academic testing and success, and most of our “play” time is spent building things.

There’s nothing more valuable than trying again. It’s really easy to look at successful companies and chart their progress from the point where the hockey stick growth started. I’m at a company now where that’s the case. We quintupled in size in the last year and a half, so if you start the chart a year ago we’d look like a massive, immediate juggernaut that’s set to overtake IBM in the next few years. But that’s not what really happened. What really happened is the CEO and his founding team lived in grass huts and ate bugs for 5 years living off projects while they polished off the R&D on nights and weekends. This is normal, and people who think starting a business is about having a brilliant idea, working on it for a couple weeks, and selling it for $20m are going to actually get lucky and win that lottery or they’re going to go back to their cushy corporate gigs.

My kids know I don’t care about failure as much as I care about them trying again. We expect to fail early and often, the more spectacular the better. Actually succeeding or winning is anticlimactic; we try again and again to the point of clearly diminishing returns. They know that its important to keep trying for trying’s sake. Chat of course runs both ways. When they go over grandma’s house they don’t ask for a popsicle; they just wear her down with polite persistence until she’s making brownies at 2 AM because a 4-year-old doesn’t understand the concept of giving up.

Other than the intrinsic qualities already covered, there is a need to be able to convince others to follow you. We can call this leadership or the ability to manage, or even call it being bossy, but I don’t think any of those things are as accurate as just saying that you need to be able to persuade people to follow you. I’m using the word persuade deliberately. I don’t believe this happens accidentally or organically. If you want people to work towards realizing your idea, you need to deterministically persuade them to stop whatever they’re doing and do what you want them to do. I am a salesperson by trade, and have made a study of the arts of persuasion. This quality is very familiar to me.

My wife and I disagree about things constantly, like every day. Sure, the big things are covered, life, kids, politics, religion, etc. But things like where we should go on vacation or what we should have for dinner are treated as non-trivial mental challenges where we both get to dig in and flex our marital leverage. She’s in marketing, I’m in sales, and both of us are full of hot air. The rhetorical battles typically include setting off points like, “I guess I’d be OK with going to that place instead of this other one, but I’m not convinced it’s better. Convince me.” This isn’t casual conversation, but structured persuasive arguments and objection handling pulled from our day jobs, convincing G2000 decision makers to commit resources to whatever it is we’re selling at the moment. We don’t talk like this all the time, but it’s common enough that we hear these things coming from the kids. We don’t have a quiet household.

When my two-year-old wants something, he holds onto your face with both hands to make sure you’re making eye contact. My four-year-old daughter doesn’t let us just commit to taking her to the park on Saturday, she asks us to put it in our phones so we don’t forget. She closes us on taking her to the park. We laugh when we hear our words coming out of her mouth. The feedback from her classes and extracurriculars is that she’s off the charts on social engagement. She’s the first kid to “find a friend” at a local park or swimming pool. When she was three she’d walk up to kids and ask their name and offer hers in return until she found someone to play with. I’ve seen her go 0 for 6 and remain unfazed. I don’t think it’s enough to be outgoing; you need to be proactively social. They’re never really too young to learn this by example. My kids are always surprised when other kids don’t want to reciprocate socially. They just don’t know any other way to be.

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