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> It's been almost exactly 4 years

Funny how often you read that in resignation posts. Four years is typically when one's shares become fully vested. At this point there's no way for him to make significantly more money from working at Stack Exchange.

It's perfectly logical to quit now, to either 1. Relax (maximizing family happiness) or 2. Start a new company (maximizing economic opportunity).

Considering how recently they pivoted into a VC-backed company it seems rather too soon for a co-founder to be jetting though. Wonder if Spolsky regrets backdating their vesting schedule (if that's what they did). Might be a bit of a cautionary tale for founders.

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All money issues aside, 4 years is also around the time you tend to get really sick of working on the same problem with the same codebase. And that's an outside bound, when the problem and codebase you were working on were both good ones. The wall gets hit even sooner if you're working on something less interesting.

All IMO and IME, of course.

All money issues aside, 4 years is also around the time you tend to get really sick of working on the same problem with the same codebase.

Four years, incidentally, is also the length of time a PhD used to take, in both the sciences and the humanities. Now it's stretching towards six - seven for the sciences and ten for the humanities, which may contribute to burnout.

There's also some speculative research that 4 years is about how long monogamous love of a wife can last barring other factors. It's been a while since I read about it, I think it was reasoned that presumably because in the old days when you fell in love you had a kid and by the time the kid turned 4 they didn't really need the full support of the father anymore to survive, so the father can start looking around and try to spread his genes further now the initial investment of the one is complete... I didn't find much evidence supporting this view at the time, and indeed the notion of "monogamous love" was itself poorly defined. But it's still fun to speculate on why 4 tends to show up so often in human activities.

Rubbish. "Barring other factors" is a qualification big enough to drive a tractor trailer through, filled with millions of counter-examples on both sides. Many fathers love their mate for life or at least decades. Many others abandon her before the child is born. Whatever explains this variance is not biology.

What evidence point to 4 years as normative? What evidence suggests that a 4-year-old doesn't need a father? "OK, kid, I see you're walking and making sentences. Here's a knife and some flint. Good luck."

Most (all?) evolutionary psychology reeks of unbased speculation sprinkled with sciency words.

No, it's 7 years, and I have that on the high authority of an old Marilyn Monroe flick.

http://en.wikipedia.org/wiki/The_Seven_Year_Itch

4 years may be speculative, but the principle is not. For those interested, Google "Coolidge effect"

It's funny how far we have come from working for the same company for all your life.

People who worked for the same company all their life did it for the pension. Those companies tended to care more for the people that worked for them. Those were the good-old-days when people were valued.

I would be willing to stay at the same company all my life, however it is clear that corporations are not really interested in this.

Relax? Start another company? Jeff has just had twins.

This has nothing to do with relaxation, or for that matter vesting schedules.

When my wife and I were about to have our twins we had read that it takes about 170 hours a week to take care of baby twins. Remember, there's only 168 hours a week.

Now that they've just turned a year old I can safely look back and vaguely recall that: Yes it probably took about that much time to take care of the little guys.

Good luck, Jeff!

Perhaps they meant 170 person-hours per week? That would be doable by a couple.

I think people without kids, when their friends with kids say they're so busy, don't realize is that all the work with kids is sporadic. You never get to get "in the zone" when child raising. I can't just change diapers for half a Saturday afternoon so I don't have to change diapers all week.

When kids are first born they need to eat every 2-3 hours including night-time. And a feeding can take anywhere from 15-45 minutes, with a diaper change per-feeding. If you're in the boat that Jeff or I were in you were very fortunate if your twins were both on the same schedule -- offset schedule twins are exhausting and relentless.

Oh, and 50% of twin births are C-sections and my wife was no exception. So her only jobs for the first six weeks were to recover, breastfeed, pump breast milk, eat, and sleep. Daddy took 6 weeks off work (3 unpaid) and pretty much had to do everything else until my wife recovered from her major abdominal surgery.

Not asking for pity or sympathy. I'm just saying that I don't know how people handle newborn twins without help from friends and family. It would be impossible.

We had friends with twins - theirs born about the same time as our first. Around four months when we were just beginning to get our life into some semblance of order I asked them if that was the case for them.

The look I got I might as well have asked them if they'd just been to the moon. Four months in and things were still massively hard work 24 x 7.

Twins are HARD and anyone who has them has my respect.

But, does it amount to less work total for the same number of children?

I think it's hard to view that way because of the way the work and pressures come.

I have two kids a couple of years apart. The youngest one is still at an age where sleeping at night is an on-off business but the oldest one is now fine.

With twins you wouldn't get that as they're both at the bad sleeping stage at the same period and that's something which re-enforces - two non-sleeping children at the same time is way worse than two non-sleeping children sequentially as there will be a period where you'll almost never get a good night.

Similarly my older child can now feed herself which means that meal times with the two of them are easier than they would be if both needed feeding.

Over all time, it might average out to close to the same amount of work per child (in later life they might entertain each other a bit more being the same age), but there are two or three years at the beginning where you're going to be severely punished.

Also financially there's no hand me downs with twins - they both want / need stuff at the same time.

I see that you're giving 110% trying to make that statement make sense.

I had a friend to help me.

From my personal experience, it's not just about vesting. It's about energy. For many folks, after 3-4 years, things just aren't the same.

Jeff's baby is all grown up. He's poured his heart and soul into this thing. Time to catch his breath, refocus priorities, and move on to something new.

Perhaps (I am speculating, not dictating) this is exactly why four-year vesting periods work. If a large chunk of people burn out or get bored after four years, a five year vesting period would create sullen, unproductive boat anchors. A three year period would have people jumping ship to found something new while they are still able to bring their prowess to bear growing the company. But after four years, both parties have maximized their gain from each other.

It's common to re-up soon-to-vest employees with additional options, especially founders.

I've always been slightly surprised that founders accept vesting at all.

What is to stop the VC from firing you the day before your options mature?

Then you would effectively have worked for them for free for 2 years, and for a low salary for a year and 51 weeks after that, all at 70 hours a week.

I would never give anyone the opportunity to do that to me.

The stock vests over time. Four years isn't the typical time for stock to vest; it's the typical time to be fully vested. Usually it's 1/4 per year for 4 years.

Vesting doesn't just protect investors. It also protects cofounders. Suppose you start a venture 50/50 with a buddy. After a year, he leaves, and three years later you've bootstrapped the company into a $100m business. Without vesting, your cofounder would still be entitled to 50%. With vesting, he would get 25% of 50%, or only 12.5%.

Sorry to be nit-picking, but the percentage of shares issued that the departed cofounder holds after 4 years would be 20%. It's not helpful to look at percentages during the calculation: look at absolute number of shares. If 1 share vests each month, the remaining founder has 48 after 4 years, the departed one retains 12, hence 20%.

Of course, this ignores any further shares the remainin founder might issue to himself by investing his own money or assets (he holds a majority stake, so that shouldn't be too difficult)

1. The standard vesting arrangement is four years with a one-year cliff. This means 25% of your stock (as a founder) vests at the end of the first year, and the remainder vests month-to-month for the next three. In your scenario it sounds like the founders have been at it for two years before their first financing.

2. Why does the VC even have the right to fire the founders or CEO? The board has that right, and presumably the VC is on that board, but their rights are defined in the financing agreement. Control is an important negotiating point when raising a round of financing.

3. Why would a VC want to invest in a company where the founders have completely vested? What's to stop them from running off with the money, so to speak?

4. That said, I've seen incorporation documents where some small portion of the founders' stock is vested immediately (maybe 5%), and the remainder follows the standard four-year vesting, one-year cliff arrangement. This makes it a little harder to raise money and the VCs might insist on changing the vesting schedule as part of the financing agreement. Generally it's just easier to have everyone on the same vesting schedule, that way nobody can object.

1. That's the standard vesting arrangement for non-founders. I have trouble imagining a cliff for founders.

It's normal in my experience. A cliff of some kind has been part of every incorporation agreement I've seen or signed.

http://startuplawyer.com/incorporation/why-your-startups-fou...

http://www.startupcompanylawyer.com/2007/07/19/what-should-t...

Moreover, if I were working with a co-founder, I would (and have) insist we vest on that schedule, and certainly not monthly from day 1.

There are a few reasons:

1. I don't want my co-founder leave before a year and having a chunk of the company. Likewise, I want to do right by my co-founder. If I leave before a year is up, it wouldn't be right for me to own a chunk of the company.

2. It's inequitable for the founders to have different vesting schedules than employees. What happens if someone joins the team pre-financing? If they get the same terms as the founders, then what about an early employee vs. a later employee? It makes for a weird, political situation.

3. It makes it easier to raise money. If you're vesting on the same terms as your investors they have no basis to negotiate over that term; they'll just check the box and move on. It passes the "blink test."

These are just my experiences, so YMMV.

Vesting of shares does not necessarily imply that you give anyone the right to fire you. For example, a company with several founders might choose to use vesting even if they never take or need VC funding, to deal with the case where a founder voluntarily chooses to leave early on. And while an arrangement with a VC could potentially grant them the ability to fire a founder, it doesn't necessarily have to, and I've seen plenty of cases where the founders did not agree to such terms (especially in cases of VCs signing on with well-established companies).

"What is to stop the VC from firing you the day before your options mature?"

A severance option in your contract which would make it even more lucrative for you if they tried to get rid of you without a really, really good reason (like a criminal conviction).

Because your shares vest gradually over time, so that by the time you get to year 4, you're well over 75% of the way there.

> What is to stop the VC from firing you the day before your options mature?

Perhaps they'd like people to actually consider taking investment money from them in the future?

Your "cliff" is typically one year, anyways.

As others have suggested, you would have likely vested 98% of your stock by then by then (typically 4 year terms with 1 year cliff, vesting monthly after the first year).

There are also often trigger clauses, which cause your stock to vest instantly when certain conditions are met. Being fired without cause (and cause here typically means a criminal conviction) is typical, although this can be structured to only take effect if the firing takes place after a liquidity event ('double trigger').

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