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What I Wish I'd Known About Equity Before Joining a Unicorn

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Re: What I Wish I'd Known About Equity Before Joining a Unicorn

#451

This has caused me some level of sadness in the past. I worked for a startup (started 6mo after founding with only 20 people and stayed for 8 years to 200+ people and 50million in revenue). During a number of phases, I worked for months at a time giving up weekends, late nights, holidays and even vacation time to get product out the door and beat the competition. I racked up 50k options, mostly all for less than a do…

8 years of weekends, late nights, holidays and vacation for a net of $200K after taxes? That's ~25K/year so if you would've worked a regular 40 hour week, 20 hours of contract work at anything more than $35/hour would have put you ahead. And you would've still had weekends, nights and vacation.

Yeah, that's the calculation that bums me out too. It's one of the reasons I am somewhat loathe to ever put in too much "extra" time anymore. I enjoy being a part of a startup for more than just the lottery ticket aspect, I enjoy creating things from scratch, etc. But the days of burning the candle at midnight are gone.

Re: What I Wish I'd Known About Equity Before Joining a Unicorn

#452

This has caused me some level of sadness in the past. I worked for a startup (started 6mo after founding with only 20 people and stayed for 8 years to 200+ people and 50million in revenue). During a number of phases, I worked for months at a time giving up weekends, late nights, holidays and even vacation time to get product out the door and beat the competition. I racked up 50k options, mostly all for less than a do…

> None of the thousands of extra hours I worked (I kept track) counted for anything Yep, that's exactly what your management was counting on.

Yeah, it's the fact that time isn't regarded as an asset being contributed is what burns my mind. For the salary I received, I think there is a reasonable expectation from the company's point of view that they get 40-50 hours of work. Anything beyond that, in my humblest of opinions, is me investing in the company. There is a logistical problem in accounting for this, obviously, and I'm far from naive on this and other points, but the underlying point remains.

Re: What I Wish I'd Known About Equity Before Joining a Unicorn

#453

This has caused me some level of sadness in the past. I worked for a startup (started 6mo after founding with only 20 people and stayed for 8 years to 200+ people and 50million in revenue). During a number of phases, I worked for months at a time giving up weekends, late nights, holidays and even vacation time to get product out the door and beat the competition. I racked up 50k options, mostly all for less than a do…

Fair enough, but you could not have known that your options would not go underwater either. At the end of the day, options let you become an investor on the cheap. Hindsight is 20-20. I think the only nice way to do it is a long window for exercising options. Lets you benefit from your hours and also protects you from the risk if it goes south.

Re: What I Wish I'd Known About Equity Before Joining a Unicorn

#454
post #434

This has caused me some level of sadness in the past. I worked for a startup (started 6mo after founding with only 20 people and stayed for 8 years to 200+ people and 50million in revenue). During a number of phases, I worked for months at a time giving up weekends, late nights, holidays and even vacation time to get product out the door and beat the competition. I racked up 50k options, mostly all for less than a do…

I have a similar experience -- albeit only 2 years -- when I left I was faced with $30k (pre-tax) and didn't have the money and was actually in debt. Not to mention the battle scars: anemic, overweight, depressed, and cynical. Luckily I've recovered now and started my own company. In addition to a 10 year exercise window I try to educate our employees and potential employees on this matter and to be as transparent as…

I think an important point would be to ensure a meaningful work-life balance is maintained. Many folks may contribute "too much" time believing that extra time is going to somehow count in someway other than in simply getting product out sooner (though not necessarily of high quality). I was in an environment that was somewhat pressurized, to say the least.

Re: What I Wish I'd Known About Equity Before Joining a Unicorn

#455

This has caused me some level of sadness in the past. I worked for a startup (started 6mo after founding with only 20 people and stayed for 8 years to 200+ people and 50million in revenue). During a number of phases, I worked for months at a time giving up weekends, late nights, holidays and even vacation time to get product out the door and beat the competition. I racked up 50k options, mostly all for less than a do…

Thank you for sharing! Very helpful!

No problem!

Re: What I Wish I'd Known About Equity Before Joining a Unicorn

#456

Earlier quoted context omitted.

The US really does have a lot of problems with their tax system to be honest. For a country whose citizens outwardly hate tax, you'd think they would have one of the best, most straightforward, and fair tax systems in the world. But instead you have one of the most convoluted, loopholey, broken systems in the world. Whereas in countries where taxes aren't as "hated" (Europe, Canada, etc) they don't pay a cent to file…

It's pretty funny. You get the same tax load in most of canada compared to california, yet the tax laws have far less gotchas like these and you get universal health care. The canada gotcha's are: 1. Everything is more expensive. 2. Housing is overpriced in employement metros except alberta. 3. You get paid a lot less than the USA anyway. 4. Canada's stock market is pretty much flat compared to the USA in the past de…

And availability of TN only helps

Re: What I Wish I'd Known About Equity Before Joining a Unicorn

#457
post #453

This has caused me some level of sadness in the past. I worked for a startup (started 6mo after founding with only 20 people and stayed for 8 years to 200+ people and 50million in revenue). During a number of phases, I worked for months at a time giving up weekends, late nights, holidays and even vacation time to get product out the door and beat the competition. I racked up 50k options, mostly all for less than a do…

Fair enough, but you could not have known that your options would not go underwater either. At the end of the day, options let you become an investor on the cheap. Hindsight is 20-20. I think the only nice way to do it is a long window for exercising options. Lets you benefit from your hours and also protects you from the risk if it goes south.

Yeah, I get that and realized I could have easily lost money too. It's not that it was painful to me when the company sold, though it did bug me then too, but at the moment of my exit interview and I was given the reminder that I could purchase within 90 days. It was in that moment that I really didn't like that my invested time had no value. Granted, it wasn't the first time in my life I realized this, it's just that I had never invested so much before.

Re: What I Wish I'd Known About Equity Before Joining a Unicorn

#458

Earlier quoted context omitted.

We have a few tie-ins too, but only for Bitbucket stuff like feature branches and occationally Confluence. What's a better alternative to Jira though?

We switched off JIRA and created our own workflow in Trello. No one is sad.

How big is your team? I couldn't imagine using something like Trello to manage tickets across multiple projects of even a modest sized company.

Re: What I Wish I'd Known About Equity Before Joining a Unicorn

#459
post #414

This has caused me some level of sadness in the past. I worked for a startup (started 6mo after founding with only 20 people and stayed for 8 years to 200+ people and 50million in revenue). During a number of phases, I worked for months at a time giving up weekends, late nights, holidays and even vacation time to get product out the door and beat the competition. I racked up 50k options, mostly all for less than a do…

Did you consider using something like ESO Fund to finance the exercise of your options? If so, why did you decide not to use them? Assuming they're willing to do the deal, if your alternative is letting the options expire worthless, it seems like a no-brainer to take a loan with no recourse unless there's a liquidity event. You wouldn't have made the full $300k, but at least a solid portion of it.

The story I related was at my previous company from about 4 years ago. I had never heard of ESO Fund until this moment. Thanks for the info, I will definitely look into that (I currently have a lot of options at my current startup).

Re: What I Wish I'd Known About Equity Before Joining a Unicorn

#460
post #424

This has caused me some level of sadness in the past. I worked for a startup (started 6mo after founding with only 20 people and stayed for 8 years to 200+ people and 50million in revenue). During a number of phases, I worked for months at a time giving up weekends, late nights, holidays and even vacation time to get product out the door and beat the competition. I racked up 50k options, mostly all for less than a do…

I'm sorry this has happened to you. I hope it can serve as a warning to other HNers that companies are not your friends, and that it's never worth investing yourself like crazy in it as an employee. Any employer will throw you under the bus as soon as possible, and possibly has already planned that in the contract you signed. That applies to three person startups all the way to gigantic multinationals. Enjoy your per…

Very much this. There is a bit of a lie we all participate in at many companies of nearly every size, though sometimes much more so at small startups. The lie is that we are all on the same team and all in this together. In reality, the team are those who actually own the company by virtue of the money they've put in (i.e., investors). Time is regarded as a non-asset, regardless of how much you invest into the company. So everyone else is there to help the real team succeed, and in so doing, hopefully get a little money yourself. Now, sure, I hope to find rewarding work and such, but I also choose riskier startups because of the potential upside (though likely small).

Sure there is always the possibility of landing work at a unicorn that is worth billions, but I think the problem is that many of us are too willing to give up parts of our lives in the hope of some very unlikely return. Either the industry needs to figure out how to value time as an asset in a meaningful way, or crazy startup-hours need to stop.

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