Alex MacCaw

Don't feel bad. The issue here is the relationship with the company & Carta and overall corporate concerns, not much about employee equity.

Briefly:

- In a startup you're granted options. Contract that allows you to buy certain amount of company shares at a specific price (”strike price”, also known as “exercise price”), which is usually the fair market price at the time when your options are granted. Options do not give you ownership of stock, instead they provide you rights to purchase stock at a favorable price.

- Fair market price is the price of the stock based on the company’s current valuation (set by an outside evaluator). Early stage companies the fair market valuation 20-30% of the valuation investors pay.

- Exercising your options means purchasing all or some of your shares and becoming a shareholder in the company. For example, if your strike price is $1.50 and you exercise your option for 1,000 shares, your exercise will cost $1,500 (1,000 x $1.50) plus any potential taxes, and you will be a holder of 1,000 shares. Now if in the future the company IPOs with a stock price of $100 you can sell those shares and get $100k or gain $98.5 per share.

- Exercise window is the time you can buy your options. Commonly in US startups required you to purchase the shares within 90 days of you leaving the company or you lose it. More employee friendly startups have extended exercise windows that let you keep the options for 7 or 10 years.

- Early exercise. Employee…

Forgive me, I wrote that last night. I realize now my post does sound very preachy and I should not guilt trip you into keeping your job! I showed you sympathy instead of empathy. So here's an actual advice:

take 1 year off with your girlfriend to travel around the world and brainstorm business ideas. http://blog.alexmaccaw.com/how-to-travel-around-the-world-for-a-year/ Alex Maccaw spent $22.000 (you'll spend at worst +-$44K with your girlfriend) and most of that money went into the flight tickets he bought at http://www.oneworld.com/ (check it out, you can design your own journey around the world). There are many ways to make it even cheaper.

If you want to gain some kind of following or traction, you could have a blog where you describe your adventures and realizations about business, life, everything.

I'm telling you because this is one of my dreams as well. I highly recommend you to read the whole article... you may even find out that you like the idea of programming on the road.

If you're interested in other nomadic-related articles, check out: https://news.ycombinator.com/item?id=8971345

I'm impressed that Stripe has been able to maintain it's culture over the years, as it grows in headcount and size. I recall reading this blog from 2012 (although I read it in 2014): https://blog.alexmaccaw.com/stripes-culture

And the consistency between then and now is fairly impressive. Ambition and Optimism seem like codified values that have emerged over time. But the one thread that is consistent is their thoughtfulness on hiring.

It should be no surprise to anyone here though, given that their interviewing doesn't consist of the standard 4-5 leetcode questions, but rather much more thoughtful rounds like a bug squash, architecture, and lots of hands on coding - algorithm rounds exist, but kept to a minimum.

Not to say that this is good and should be the new standard - just that it is extremely thoughtful and was going against the grain. Wish more companies would think about their hiring practices from first principles and didn't just copy Google

If you can spare the time, read 'Venture Deals' by Brad Feld and also http://blog.alexmaccaw.com/an-engineers-guide-to-stock-options

Also, it's not clear from your post what you mean by 'shares should be vested'. Do you mean one of the following?

- The shares will be granted immediately, and fully vest only if/when the business closes the VC round

- The shares will be granted and fully vest at the same time, only if/when the business closes the VC round?

- The shares will be granted if/when the business closes the VC round, but will vest over some period of time after that

You say that the 1% is being offered as a reward for work you have done. If the shares are for _past_ work, then there should be no need for them to vest over a period of years. You've already earned them. If they vest in a normal fashion (4 year, 25% per year, 1 year cliff) then you're being incentivised for _future_ work, and not rewarded for previous work.

Great post by Sam. For employees, I'd also refer to Alex MacCaw's An Engineer’s guide to Stock Options[1]. Alex used to work at Stripe, and at the end of his article he shares some intersting bits of stock tax alternative not covered by Sam:

If you can’t afford to exercise your right to buy your vested shares (or don’t want to take the risk) then there’s no need to despair – there are still alternatives. There are a few funds and a number of angel investors who will front you all the cash to purchase the shares and cover all of your tax liabilities

And he goes further:

If you’re interested in learning more about financing your stock options then send me an email[2] and I’ll make some introductions. I’ve set up an informal mailing list, and have a group of angel investors subscribed who do these kinds of deals all the time.

[1] http://blog.alexmaccaw.com/an-engineers-guide-to-stock-options

[2] the link is to alex at alexmaccaw.com

I don't mean to be pointlessly negative, but this is the kind of post that makes me chuckle a bit at the idea of Svbtle being 'the future of journalism', and a hallmark for posts of a superior quality. There's nothing particularly actionable or novel, which would be excusable if it were at least interesting.

I don't mean to disparage Alex -- a lot of his posts have been incredible, such as how he implemented asynchronous image uploading (http://blog.alexmaccaw.com/svbtle-image-uploading) -- but this would benefit from showing it to an editor and asking for advice.