I once interviewed a candidate for a role at Astranis who said he had basically worked at a startup: yes, he worked at a big company, but his team was a small subset of the larger whole.

The big company? Amazon. The “small team”? …Amazon Web Services.

I struggled in the moment to understand the comparison, and have struggled since to articulate exactly why his equivocation was so horrifically false.

But now, I think I’ve got it.

Startup life is all about operating with constraints.

Take away the constraints, and you’re left with a normal, scaled-up company. No constraints, no startup.

And although it’s true that having only a few people on your direct team is one example of a constraint, it’s one of the least meaningful.

If you have only a few people on your direct team, the next question is simple: how much responsibility does your team have?

At a Series A startup, a business team of five people might be responsible for finance, HR, IT, facilities, supply chain, events, communications, PR/marketing, and more. At Amazon Web Services, I wouldn’t be surprised to learn that 5,000 people collectively cover those functions. So even if your direct team — say, procurement of a specific commodity — is just five people, you still are dedicating many orders of magnitude more time than would be spent on that kind of business task at a startup. (And the fact that Big Amazon spends 100x more time than you on similar tasks is no refutation of that fact.)

Even at a slightly higher level of abstraction, it’s probably the case that many folks claiming to be part of “smaller teams at bigger companies” are just ignoring all of the support functions that are taken care of behind the scenes. When a new hire starts in their “small” division, they almost certainly still get a laptop, and company log-ins, and new hire training, etc. from teams that are adjacent to “the small team.” So, really, they’re part of a small team within a massive support lattice. Which is not a small team at all.

To take this point one step further, consider the systems and the support available to a small team at a large company.

Big companies have an existing superstructure that protects the small team from risk.

You have a legal team that sets guidelines for what you can agree to with outside vendors, and templates for establishing any kind of agreement under the sun. You have nested layers of executives above you, all of whom provide air cover in the best case and scapegoats in the worst. Your parent company’s scale and brand name give you some weight to throw around with customers, regulators, and outside partners. And you have untold hundreds of people fighting for your interests behind the scenes: from lobbyists, to participants in regulatory proceedings, to fans on social media.

At a startup, you have no such superstructure, except that which you personally build.

And for support, just think of the difference between what a startup has to do to get access to experts, vs. what a small team at a big company has to do. Want to know how to navigate a challenging legal matter at Amazon? Just call any one of the 800 lawyers on staff.

If you’re at a startup, you will have to work through outside counsel — which could mean identifying and vetting a new specialty firm, navigating their onboarding (billing, engagement letter), getting them up to speed on the business, and more, even before you get any advice.

Perhaps the biggest difference of all is that a small team at a big company has backup, and a startup does not.

If you run out of money in your budget at a big company, your boss is in trouble; if you run out of money at a startup, you go out of business.

If you need more money at a big company, you can ask for it; if you need more money at a startup, you need to raise it from investors.

At a big company, you can focus on the tasks your division has been assigned, and expect them to stay mostly the same throughout the year. At a startup, focus is a luxury that you can only rarely afford, and you’ll inevitably spend your time fighting fires while letting others burn.

At a big company, you’ll only rarely do something for the first time, so you’ll have in-house experts to help you understand how everything works. At a startup, you have to figure things out by yourself.

There are two morals to this story. First, there’s really no equivalent of working at a startup, at least in the world of big tech. But second, many candidates from big tech don’t understand what startup life is really about.

Some candidates will be scared away by the facts of startup life, so it’s tempting, as a hiring manager, to underplay the challenges. You want to close candidates, so you want to tell them what you think they people want to hear.

But it’s far, far better to be honest — because for the right candidates, the challenges posed by startup life are the most exciting parts of the job.

I signed up for entrepreneurship on hard mode. I don’t want to join a company that has solved all of its problems, or at least all of the hard ones. I want the crazy, messy, terrifying, invigorating startup life. I want a job that tests my skills as much as it teaches me new ones, and a job that gives me nowhere to hide.

It’s just more fun that way — so if you tell me there are no challenges, I’ll tell you that there’s no point in hiring me.

Thanks for reading Silicon Valley Outsider! Here are a few past editions that you might like if you enjoyed this one:

• 🙏 An Outsider’s Search for Meaning

• 😱 Should I have shut down my startup?

• 👎 Pessimism is easy, but that doesn’t make it right

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