In the final rounds of a mature start-up looking at IPO in 12-24 mo. Entire comp won’t equal my current base but would hope for potential stock bump later. I’m pretty done with my large holding company job (i do feel agencies are dying) but my guaranteed salary is pretty high. Am I crazy to walk away from this? I could ride holding company out for as long as I can or take the risk and jump brand side hoping for potential stock jump. Thanks in advance for any insight/experience.

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How much risk can you absorb? If you have a family or outstanding debts you might need to think differently.

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Are you chasing a creative work challenge? Or comp?

How much more time do you have before you can retire (assuming you want to someday)?

How much do want to risk that timeline?

12-24 months before an IPO is an eternity in which a lot can go sideways. You ready for that?

Do you really believe in the mission of the new company? Or is it just a job?

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If your unhappy at your current place and you think you’ll be happier at the new one, then I think that alone would make it worth it. One thing to note about “equity”. If your granted stock at a strike price (price per share when they build the offer letter) that is before ipo, it’s probably a fairly high price. The value you would get when your stock finally vests will be higher but when you go to buy it you’ll be paying capital gains on it. Factor the amount of tax over the amount of potential profit. If that number isn’t high enough for you, you may want to negotiate on the base salary.

Lots of people forget about the tax implications of stock and get blinded by the “potential to be rich”

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I’m in a position that can take on some risk. (double income no kids)

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Hmm...what’s your foresight on the company’s success in IPO + beyond? I know it’s hard to say for sure but curious if you’ve evaluated their market/their runway and funding/their growth so far etc.

Separately i’m curious why your total comp isn’t coming close to your current base salary. How far off are they?

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The reason I ask is because if they’re doing well, they shouldn’t be very far off/should ideally be able to beat it - given they’re mature and close to IPO. So i’m assuming at least series C/D, especially if they need an ECD-level creative. I don’t want to jump to conclusions just yet but my immediate concerns are they’re either not doing well or they’re lowballing.

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Looks like you’re just after higher compensation. Evaluate what day to day job will make you happiest. Otherwise, if chasing cash is your objective, just make make a few ballsy plays on the stock market.

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Thank you all!

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Appreciate the responses. I’m willing to go down a bit in comp to get into tech category. What is missing in the comp picture is how much equity they will offer.

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