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Working at a startup is overrated, both financially and emotionally

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Re: Working at a startup is overrated, both financially and emotionally

#121
post #109

The author also fails to mention the stock option trap. I've seen offers at early state companies like this: * $150k base (take-home $100k) * $30k/yr options that expire 3 months after you leave or 10 years. You have to either set aside 30% of your take-home to invest in a extremely high risk single stock or you're chained to your desk until the company exits. If you golden handcuff your way to an exit, you better ho…

The ten year expiry is an IRS rule for issuing an ISO.

Re: Working at a startup is overrated, both financially and emotionally

#122
post #34

Earlier quoted context omitted.

> The author likely comes from a structured, religious background How on God's green Earth did you jump to that conclusion? Can't it just be a matter of personal preference, as you said it yourself?

>>> The author likely comes from a structured, religious background >How on God's green Earth did you jump to that conclusion? The author wrote: "From the ages of 19-21, I spent my time as a missionary for the Church of Jesus Christ of Latter-Day Saints, popularly known as the Mormon church. I worked 12 hours a day for two years straight with only Christmas and Mother’s Day off. [...] For this job, I was paid a total…

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Re: Working at a startup is overrated, both financially and emotionally

#123
post #83

I think this is a really good article, but I think that one of the things it misses is that a huge reason the math works out so badly for startup employees is because founders and VCs take the lion's share of the gains. I mean, in my experience at startups, founders typically own around 40% of the equity. The option pool for all other employees is around 10-20%. Now, I certainly believe startup founders deserve far m…

> what founders risk in terms of opportunity costs and lower wages is usually only slightly more than very early stage employees Maybe this is different for others, but my co-founder and I spent 2 years bootstrapping before we got our first customer. We gave up 2 years of wages and consumed our savings to do this with no assurance of success, and even after that first customer it was another full year before we had a…

It definitely is more risk. However when I evaluate startups I'm comparing them against other jobs. Stable income it may be but the runway is short, and depending on the founders it may or not be well communicated. So it is much less stable than a job in a big company. So to me I want a good multiplier.

Many of the payoffs I've seen for startups that did well for early employees put earnings on par with what I've done at a large company without the startup risk. And that's for the ones that do very well which is a low chance.

So in the end I personally would get a lot more stress and a lot less income to usually being equal in a great case.

So generally it doesn't seem that worth the risk, low control, and probably low payoff.

I'd actually be more likely to join a startup in some years when I'm financially at a retirement or FIRE point. But then it's like, working for a founder on their idea, and maybe the pressure to hold out for 5-10 years there for the actual payout.

Just my mental space around it.

Re: Working at a startup is overrated, both financially and emotionally

#124
The key thing I recommend is to *prioritize who you want to work for* (or have as clients). People who will care about your well-being. Find what they need and try to match your skills.

I had my own startup at some time, and worked for both other people's startups and for big corps. I used to maximize career and CV over quality of life. I was easy prey to assholes/takers/sociopaths. Burned 15 years of my life without much to show. On the upside, I really appreciate now working for good bosses and good leaders. I could easily earn 1.5-2x in a soulless corporate job. But I know my current employer would go out of its way to try to not screw me over while the 2x employer will throw me under the bus the second I stop being useful.

You can study or do research on your spare time. Good bosses will understand if you eventually move on. And some might even help you progress against their convenience.

Re: Working at a startup is overrated, both financially and emotionally

#125

I think this is a really good article, but I think that one of the things it misses is that a huge reason the math works out so badly for startup employees is because founders and VCs take the lion's share of the gains. I mean, in my experience at startups, founders typically own around 40% of the equity. The option pool for all other employees is around 10-20%. Now, I certainly believe startup founders deserve far m…

From my own household/wife I have a person who's worked her ass off for a hugely incompetent CEO who has a majority stake. When I say ass off I mean 12-14 hours a day even on weekends. A promise of unlimited holidays and then coercing all employees to work during government mandated holidays and now he's trying to scam her out of her less than 1% options by coercing her to write a maternity leave policy that would ma…

It's funny how often I got rejected after saying that I am not 24/7 available and that I believe that, if someone needs to have this kind of availability, it means that something in the company is not working and needs to be fixed. The words they used in the rejections were always something like: "we feel like you are not willing to put enough skin in the game" or "everyone else sees the opportunity here is is willing to work their asses off, why are you different?" It's specially funny to hear all this after the CEO has basically told me that they are planning for an exit in a couple of years, and being someone who has seems this first hand a few times., it usually means everyone works til the point of burn out and, in the end, the CEO gets handsomely while everyone else has a regular Wednesday.

Re: Working at a startup is overrated, both financially and emotionally

#126
post #92

Earlier quoted context omitted.

> Savings should only come into it if you're leaving before the liquidity event. Which is another way some startups screw people. If the company is not willing to budge on the "standard" 90-day exercise window, there shouldn't be any negotiation. Just walk away.

There are two types of options, NSO and ISO. You want ISO as an employee because it's better for taxes, but that has a 90-day exercise window set by the IRS. You can push for yourself paying higher taxes in exchange for more flexibility, but it's a tradeoff. https://carta.com/blog/pte-90-day-window/

Zach Holman one of the first github employees didn't get to exercise any of his options for the aforementioned reasons. When they tell you to throw your life away to believe in the vision, nobody tells that 24 y/o to get a lawyer to understand what that actually means.

He compiled a list of startups with sane exercise windows:

https://github.com/holman/extended-exercise-windows

Re: Working at a startup is overrated, both financially and emotionally

#127
post #6

It also makes a huge difference if the startup is your primary source of income or not. My wife worked for several startups, all of which failed. But since I had a more stable paycheck, it wasn't so bad, and we just treated the extra startup income as a bonus, and had very low expectations on cashing in on the equity.

Problem is, how do you support this? You must have made a lot of money to both (a) support your family, and (b) pay for the childcare that your wife would have been too busy to help very much with. Either that, or you lived in a low cost of living area and were able to do some kind of price/salary arbitrage. And if the solution was "make a lot of money", then that again makes childcare doubly important, because if yo…

Why do you assume they have children? Not everyone choose to have children and frankly, that's a great decision. I'm a parent but I subscribe to the feeling that instead of assuming everyone has/wants kids, we should praise people who don't.

Re: Working at a startup is overrated, both financially and emotionally

#128
The article is quite comprehensive and well written. There's also a lot of assumptions and false alternatives, like that people work to maximize financial outcome or that there's an equalprobable choice between working for startup or for FAANG.

My opinion is to try working for early stage startups while one is young and idealistic, choosing it by heart, thus maximizing its chances to success. Getting familiar with different techs and stacks. Getting a good networking while visiting meetups and hackathons. Even if the startup won't fly, it will help to get much more interesting position in established company later.

Re: Working at a startup is overrated, both financially and emotionally

#129
I would love to see more small-ish companies in a niche with a good product, and competent people that are maybe slowly growing, but not on the rocket ship ride. That kind of environment has always felt like a place where you can get good work done.

Re: Working at a startup is overrated, both financially and emotionally

#130
post #119

Earlier quoted context omitted.

From my own household/wife I have a person who's worked her ass off for a hugely incompetent CEO who has a majority stake. When I say ass off I mean 12-14 hours a day even on weekends. A promise of unlimited holidays and then coercing all employees to work during government mandated holidays and now he's trying to scam her out of her less than 1% options by coercing her to write a maternity leave policy that would ma…

I’ve never had these abuses working for a startup. I feel like you have to push back against things instead of just going with it. Or choose the position better because they sound like bad jobs regardless of the type of business. That’s what I can’t help thinking when I hear that because I’ve now worked for 5 different startups and while there was some crunch time occasionally the majority by far was an 8 hour day an…

We either need agents who will negotiate on the employees behave or some kind of training that is part of a 4 year degree. Negotiations and finances are hard - this is why some people are good at selling and some are not. Engineers are usually good at their primary job and usually not that good at defending against other social engineering tactics founders use

edit: don’t want to blame founders, they also need to preserve their equity for future employees but there has to be a better balance

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