Ask HN: Joining a Late Series Startup in SV. Please Help

So yellow/red flags:

1. ARR in the XX mil, but you are taking a pay cut?

2. You will declutter the tech stack and work on exciting products?. Usually in a startup (or any other company) - you touched it, you own it. So once you declutter the tech stack, I am not sure that you will have time to work on the other exciting projects (or even if they will still be relevant).

3. Why do you even need to declutter the tech stack? what happen to the original programmers? what happen to proper process? do they have unit tests? CI/CD? Can you sandbox this code in a micro service and just call it?

4. The option thing looks like they are increasing your switching cost. I.e. once you buy the options than you will be limited in your moves both inside and outside the company.

1. I should have been clear, I am not taking a pay cut in the base but the overall pay(base + rsus)

2. I am glad they were upfront and honest about it. The manager said 50:50 split.

4. Yeah I agree with this.

So the manager can be honest, but it is usually not even his call. The company will likely to put a lot of value on the maintenance side (which bring the money) and less on new projects (which get postponed if there are any issues in the maintenance side).

I do not think that the manager is lying to you. TODAY he see it as 50/50. But what happen if the cluttered project is late? What happen if there is a need for new features in the cluttered project. I would accept the job only if you are ok staying in the cluttered project team for at least a year or two.

Thanks for the insight you are dead right about the managements view.

Don't spend any money until you are sure you'll be getting a return -- def. not on day one.

I've never actually heard of a compensation structure which has >$100k of options to even spend on day one. Most of the time they are vested on a schedule.

There's 1 year cliff for vesting but apparently one can excercise at the current strike price on day one and that's pretty common among other startups with folks who want to avoid the AMT

Imo you are taking on a huge risk. Your shares will be worth nothing the majority of the time. In the future if your shares are worth a lot and you need to pay taxes that will be a nice problem to have.

It's "83(b) election." It's interesting a late stage startup is offering this. But do NOT do it.

Do this only for very early stage startups where your total expense might be a few thousand dollars for maybe 1% or more of the startup. At most, you lose a few thousand dollars.

Spending $100K to optimize possible future taxes is a bad idea. At this stage, you should just think that future AMT is a good problem to have. Put the $100K in safer instruments.

At some point in the future, if it becomes clear that the company is on path for an ipo I could pay for it then.

I will hold off until then.

That's a common way to save on taxes by paying a bit upfront. It's usually not done at such a late stage because of the cost when the strike price is high. It's more common in pre-A or at least pre-B companies when the strike price is smaller.

I certainly wouldn't drop 100k unless they offer a commensurate signups bonus (the 100k goes to the company so they could give you a bonus of $100k if you exercise the options which should help, though you'd still be on the hook for the taxes on that bonus).

Cash is king - keep your savings in the account. We're really overdue for a rebalancing of the economy and you want the cash at that time. That is a gaurantee. This startup, where it could succeed will more likely not go public.

Keep your current job or get a job that pays you better, but hold on to your CASH!

Don't take a pay cut.

Big companies are offering $400k+ for E5 (mid-senior) engineers. No startup in the world will be able to match that in liquid compensation.

Then they should raise enough money to afford their employees. (Or make their equity meaningful, with longer exercise windows or by loaning the money for early exercise).

They have raised a significant amount but have been stingy in the stock options grant.