Hey! 👋 I have an interview coming up for a Chief of Staff position at a startup currently in stealth mode. Position is unpaid at first but will be offered equity. What concerns does this impose? Anyone navigate this situation before? Thanks!

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A startup that I’ve recently been advising thought it was going to be funded in June and it may still be another several months. Just be aware that securing funding can sometimes take a lot longer than anyone anticipates (and often does).

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Attorney is spot on; last year - rather than a lump sump of a few million from a VC one company I worked at had to resort to small checks from family offices for 8 months. 0% interest days are far behind us. This is the new normal; you need to make the decision and calculus of weighing risk and reward.

Don’t listen to these jokers, if the role sounds like fun AND you can afford to do it go for it! I’ve worked at a couple of startups and support a few others and absolutely prefer it to my prior roles at F500 companies.
Eyes wide open though, decent chance this company won’t make it and you’ll likely be underpaid for the first year or two, even if they are successful at raising capital. Be honest with yourself about your personal motivations (money? Title? Experience? Peer group?) no right or wrong, just be clear about it.
Sounds exciting!

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I want to be just like you…someday

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I wouldn’t even waste my time with something like that unless it’s a huge amount of equity a.k.a. your cofounder or you truly believe in the idea and if that’s the case, you might as well just invest your own money into it.

Equity especially in a stealth start up that’s probably pre-product, pre-customers, and pre-revenue is worthless. Essentially working for free and you’re most likely just gonna do all the work for the cofounder as an admin.

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If they’re stealth mode and unfunded, then they’re too early stage to truly need a chief of staff

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Y Combinatir's big new thing is that you should get a CoS hired right away.

They should pay you, OP, unless they're giving you co-founder-like equity. Don't fall for the "we'll all bootrap together" malarkey.

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Concerns might be that…. It’s literally unpaid.

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Prospective pay doesn’t put food on your table. You’re better off starting your own company.

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why would they need a chief of staff if they literally don’t have any money to pay their employees

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Ask to see the records of any funding or have him/admit the startup is unfunded

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On my list of top questions to ask!

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My friend took a position at a series A start-up for below market pay. They said they’d give her a raise at series B, but they didn’t.

My lesson from this is to be DEEPLY skeptical promises of future pay. Any startup will always have pressure to keep there operational costs low especially by advisors and board. They have every reason to try to exploit you.

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Run from that interview.

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The cardinal rule is you ALWAYS get paid for your time. Equity is a farce. Anyone posting that kind of role is either unfunded, a total amateur that should not be taken seriously, or has a nefarious intentions (my money is on serial killer).

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No way would I work for free. Get your equity in writing before committing.

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Hard pass. How are you going to pay your bills for the first couple of years assuming this firm doesn’t go under right away? For a title?

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Unless they are giving you massive preferred equity with voting rights, I would be very very hesitant. Most likely you’ll spend so much time and energy and the founders will pocket everything and will leave you with nothing.



What’s difficult is you’ll be working for free-doing them a favor—but they will lean on you as if they’re paying you. If you do it take partial w in shares, and part as a note payable, which is secured against the assets of the company. If things fall apart and they have to liquidate, note holders get paid before shareholders - who usually get nothing. Question: why did these guys have to publicly list this position? They should have been able to harvest their personal networks for someone to take this. Check on their reputations any way you can.

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I just really want to be a Chief of Staff. But maybe this is the wrong way going about it.... Thanks for the comments!

What kind of company is it? Why would a start up need a Chief of Staff? Is it a non-profit?

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I know nothing of this world but working unpaid pre funding at a start up surely deserves a co founder title?
I see nothing wrong with this - I would prefer equity to salary.

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