There are two buried leads in the Segment/Twilio news:

1) This is the biggest YC acquisition by a large margin. Cruise was next at $1B.

2) The company was setup so that everyone on the team shared in this win, including alumni. Let's expand on this...

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2/ Point #2 was long-term thinking that started many years ago when they eliminated the post-employment exercise time limit (typically 90 days) from their employee option agreements. This is *KEY* https://twitter.com/calvinfo/status/622550129518612481

3/ It means that exiting employees who couldn't afford to exercise their options after they left the company didn't need to, and still very much benefited from this exit. Unfortunately, most startup employees don't exercise when they leave.

4/ Instead of only those who were already well-off, who could put the cash up to exercise becoming *even richer*, this changed the lives of a substantial number of households. Perhaps 100s have dramatically increased financial freedom.

5/ This speaks to the incredible character and long-term thinking of the founding team.

Major key: they now have a whole roster of talented folks who they can call on for the rest of their careers. These folks can trust that they'll be taken care of. Very powerful.

6/ It's tempting to get cajoled into not doing this or ditching it by the rest of the cap table, some of whom see alumni as "deserters" or "unbelievers" undeserving of a windfall, but the reality is that these sorts of restrictions just amplify privilege.

7/ I am THRILLED that so many of my hard-working colleagues and former colleagues can now live a life freer of the burden of financial pressure, one of the key ways capitalism terrorizes labor.

8/ They can choose to leave bad bosses. They can choose to leave unethical companies. They can take unpaid leave to care for family members. They can choose to work on things that are fulfilling and empowering, not only for the paycheck.

9/ While we definitely need to continue to work towards more equitability for labor, it's refreshing to see a bright spot in the darkness, particularly when it's so personal.

10/ @holman has compiled a dope list of startups with extended exercise windows. You should work for one. It says a lot about the character of its leadership. https://github.com/holman/extended-exercise-windows

11/ Disclaimer: I am an employee of Segment, and these are my views, not Segment nor Twilio's or any other entity for that matter. None of this information is confidential.

12/ Bonus: it wouldn't be a great tweetstorm without a glaring grammar/spelling error.