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What I tell people who ask if they should work for a startup

Working at a startup is a lot like SV Season 1, less like SV Seasons 2+

The primary factor, maybe the only factor, when deciding between a corporate job and a startup job comes down to personal outlook. Do you want a job or do you want an adventure?

And that question shouldn’t be answered lightly.

Startup is hard. It’s hard in ways that corporate jobs aren’t. If you’re really doing startup, you’re going to be underfunded, under-resourced, and basically a small-time player in the shadow of your corporate competition. You’re always looking over your shoulder, waiting for the other economic shoe to drop. And you’re not always going to be able to console yourself with company-underwritten massages or blow off steam on the company ping-pong table.

Yeah, I know perks and diversions are a hallmark of startup lifestyle, but if they’re spending money on these things in the early days, they’re overspending and diluting their growth— I’ve been down that road.

But we in startup also tend to complain too much about how hard startup is. Corporate life is hard too, just in different ways. I remember the lack of speed and flexibility you find in the corporate world. I remember that you usually have to wait days, weeks, or months for decisions or meetings to get resources to actually get the work done that you’re supposed to get done.

What’s worse: Not having the money to get something done or having the money but having to jump through a hundred hoops to get access to it?

So anyway, over the last few weeks I’ve had several calls with people who are friends of my friends and are moving to the hotbed of startup and quality of life that is the Raleigh/Durham region. One of the many cool things about this place is you can either go to Cisco or Red Hat or Cree (and soon maybe Apple and/or Amazon) and hop into a cube or you can walk a few blocks away and join any number of startups, from freshly-founded to soaring-towards-IPO.

OK, not so many of the latter, at least not those that publicly talk about it. But they’re here.

The reason these calls come to me is because those people I’m talking to have spent at least some time, if not their whole career, in startup. These conversations usually start around what startup is like in Raleigh/Durham. It’s hard. But it’s hard everywhere.

The conversations almost always end up in a discussion about whether or not the person wants to do startup again.

I get it. If you’re actively looking for a new job, you’re walking away from something. At best, you want to use mental muscles you haven’t used yet. At worst, you’re walking away from the explosion with your backside charred.

The good news is I’ve had that conversation a hundred times. And I can state, beyond the shadow of a doubt, that choosing between startup life and corporate life comes down to whether or not you want to live the adventure.

Here’s what I tell them.


Most of the bigger startups and even some of the smaller ones can be competitive about money if they’re serious. And even if they’re not competitive, they can offset the base salary by tying future money to success in a greater proportion.

In other words, you can level the money game if you work a contract that has you making a substantial bonus and even a bump when the startup hits its milestones. Shoulder the risk, reap the reward.


Corporate jobs aren’t safe. Layoffs happen just as regularly as startups run out of money, if not more often.

And this also factors into the adventure equation. When I was between startups back about 10 years ago, I looked up a former mentor of mine who had at one time helped me fund a splinter startup attached to his business. We got bought within a year and everyone did well.

He wound up at a giant company and while we grabbed lunch in his corporate cafeteria, he told me that where he was now was “a great place to just, you know, hide out.”

That made me incredibly sad. But that’s a safe job. No risk, little reward. And if that kind of security is appealing to you, then your answer to the adventure question is zero. Zero adventure.

Big Risk = Big Payoff

Most startups don’t have a big payoff. In fact, I’d tell you that even most of the successful startups are high risk, medium payoff — unless you’re a founder and you don’t get pushed out or super-diluted, or you’ve made the right deal at the right time (see the base salary vs future money equation above).

Most startup employees end up with a nice bonus check when the startup exits. But you also wind up putting off things like 401Ks or low-deductible health insurance or outside investing for so long that you end up breaking even or a little better most of the time.

Yes, all it takes is one home run (or a couple triples) to flip the equation. But you have to be more than an employee for this to have it work out for you. You have to be part of the adventure. No one rides for free.

Old Boy Network

Yeah, there’s an OBN in startup too, and it’s an odd, hard-to-figure out network that changes from city to city and from stage to stage. But all the bad things you hear about the corporate world, from shunning to backstabbing to sexism, it’s all here in startup too.

At least in the corporate world you can figure out ways around it sometimes because it’s usually all the same type of people pulling the strings. In startup they kind of pick and choose who the favors go to. I’ve never been on the right side of it, so I don’t know what the math is there.

But I can tell you that in startup it’s easier to work around it by making a shit-ton of money for your company. Even then though, you’re only as good as your last shit-ton.

Which leads me to my grand point.

It is not a sexy adventure.

It’s a grind just like anything else. Your talent is going to get you far, maybe further than in the corporate world, but there are a million other outside factors working against you. You’re never going to be ready for all of them, so flexibility and internal fortitude are key.

The payoff though, like any good adventure, is something you can look back on and cherish. I tell my kids all the time — don’t value things, value the experience. This is why you do startup. We don’t all make it to the end rich. In fact, the older I get, the more I’m convinced that getting rich couldn’t be more out of phase with the actual goal.

The goal is to live the adventure — good, bad, and ugly. If that’s what you want, then go into startup. If not, then find a good place to hide out until you’re ready to jump in.

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