Alex MacCaw
blog.alexmaccaw.com · Personal blog · on HN since 2012
Alex MacCaw, a startup founder and former Stripe engineer, writes on stock options, career advice, company culture, and web development.
What HN saysCommenters point to his stock options guide as covering the basics in excellent detail for engineers, and to his post on Stripe's culture.
78HN people shared it
21linked it in comments
98stories submitted
5.0Kstory points
8 months agolast shared
2012people per year2026
Most-shared posts
- 1An Engineer’s guide to Stock Options13 people · 994 points · first shared 2013 · 154 comments on HN
- 2What it’s like to work for Stripe4 people · 287 points · first shared 2012 · 57 comments on HN
- 3Advice to My Younger Self4 people · 8 points · first shared 2019 · discussion on HN
- 4How to travel around the world for a year3 people · 246 points · first shared 2013 · 149 comments on HN
- 5APIs that will transform the Web in 20133 people · 233 points · first shared 2012 · 105 comments on HN
- 6Humble Beginnings3 people · 148 points · first shared 2012 · 25 comments on HN
- 7All you need to know about CSS Transitions3 people · 118 points · first shared 2013 · 11 comments on HN
- 8An Asynchronous Image Uploading Interface for Svbtle3 people · 43 points · first shared 2012 · 16 comments on HN
- 9How yield will transform Node.js3 people · 18 points · first shared 2013 · 1 comments on HN
- 10Asynchronous UIs - the future of web user interfaces3 people · 10 points · first shared 2013 · 1 comments on HN
- 11SEO in JavaScript Web Apps2 people · 82 points · first shared 2013 · 51 comments on HN
- 12Abba - JavaScript a/b testing2 people · 80 points · first shared 2013 · 16 comments on HN
- 13Time to First Tweet2 people · 63 points · first shared 2013 · 10 comments on HN
- 14JavaScript ‘wake’ event2 people · 44 points · first shared 2013 · 7 comments on HN
- 15How not to write recruiting emails2 people · 22 points · first shared 2013 · 9 comments on HN
What HN people wrote when they linked it
pawelwentpawel · 2016-12-20
Can anybody share some info on how taking stock options in a US company differs from a UK one? A lot of the reading applies to US market. I'm wondering if any of the advice is not transferrable.
Also, I believe that this is a good read - https://blog.alexmaccaw.com/an-engineers-guide-to-stock-options
Peroni · 2016-09-21
This post covers all the basics in excellent detail. Written by an engineer, for engineers: https://blog.alexmaccaw.com/an-engineers-guide-to-stock-options
SeeDave · 2016-04-10
I agree, to a certain extent, but mostly for the initial load. I remember reading an interesting article about how twitter does exactly this with "time to first tweet" being the defining metric. Beyond that, I think stateless services/web sockets/DOM-manipulation would best serve users who have a need for real-time updates and dynamic content.
For reference: https://blog.alexmaccaw.com/time-to-first-tweet
ryanSrich · 2015-12-23
There are several options one must weigh when they are deciding on job offers.
Where you work is so important and yet so many people seem to put such little effort into negotiation, risk assessment, runway, overall comp, etc. etc.
If you're taking equity in place of a market rate salary you better to be absolutely 100% sure you know you're taking a massive risk and forfeiting real dollars for hypothetical dollars that 9.999/10 will never exist.
Note: A great read about equity http://blog.alexmaccaw.com/an-engineers-guide-to-stock-options
elliotz · 2014-04-16
It's a great policy. Stripe was doing this 2 years ago: http://blog.alexmaccaw.com/stripes-culture Anyone know if they still do it, even after growing?
sobes · 2013-12-11
Congrats! Though I'm curious to know what you mean by "real" startup. What's a fake one?
One of the most important questions to ask is how they're funded. Most startups fail, and funding is the most accurate proxy for stability. At the very least you'll know if it'll be around long enough for you to learn something while working there.
Also, if you're getting stock options, I suggest you read this article (tells you what questions to ask so that you understand what they're worth):
http://blog.alexmaccaw.com/an-engineers-guide-to-stock-options
maccman · 2013-10-12
Or Saigon - had a great time there.
http://blog.alexmaccaw.com/traveling-writing-and-programming
rahimnathwani · 2015-02-13
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.
Red_Tarsius · 2015-02-10
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
DanielRibeiro · 2014-04-18
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
johnhess · 2016-08-03
I really like this one: https://blog.alexmaccaw.com/an-engineers-guide-to-stock-options
andygcook · 2015-12-22
Alex McCaw mentioned in Clearbit's launch post earlier this year that Svbtle is using their API to auto populate their sign up form:
http://blog.alexmaccaw.com/clearbit
My guess is that Magic is using Clearbit's API as a base, then layering on their own scraped data sources as well, which is a pretty common strategy for these types of APIs.
teachingaway · 2014-09-17
explanation of stock options generally - http://blog.alexmaccaw.com/an-engineers-guide-to-stock-options
ds_ · 2013-12-19
One way: It leverages generators, which helps in avoiding callback hell (http://blog.alexmaccaw.com/how-yield-will-transform-node)
Koa is written by the same author as express.
neilk · 2013-08-17
Yes, it's called "JavaScript". Specifically, combining generators with promises.
http://blog.alexmaccaw.com/how-yield-will-transform-node
Definitely not as clean as a whole new language, but you can program like this today, at least in bleeding edge node and some recent browsers.
jmduke · 2013-01-11
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.
grinich · 2012-11-28
Well, maybe. Alex works at Stripe. And wrote about having a browser API for payments.
http://blog.alexmaccaw.com/one-click-signups-and-purchasing
astrojams · 2012-08-12
Your guy is posting the front end code no?: http://blog.alexmaccaw.com/svbtle-image-uploading
enra · 2024-01-06
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…
pliao39 · 2019-08-28
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