Go to the founder of a startup, and tell them you want them to give back their stock. Tell them it’s in their best interest. Tell them they can earn it back, if they stick around for a while. Sound crazy? It probably will to them. Yet bizarrely enough, it’s the right thing to do.

This is founder vesting, and companies are regularly destroyed by ignoring it. Let me explain with a hypothetical…

Imagine AcmeCorp, a new startup. Jack and Jill are the founders. They incorporate and give themselves each a million shares – in other words, splitting the company 50/50.

The next day, Jack has a change of heart. Startups are a lot of work! He quits AcmeCorp and takes a cushy executive gig at a fortune-500 tech firm. Jill’s left solo.

Years pass. Jill first works without salary, then pays herself a pittance. She bootstraps the company, starting with consulting and moving on the develop a highly successful web service. As she brings on staff, she issues stock to new employees, ultimately handing out a half-million shares of the company. Eventually she’s the CEO of a 50-person firm, pulling down a respectable $200,000 per year as the CEO; nearly as much as Jack’s pulling down at his gig (not including his benefits and bonuses).

When the company is finally sold, it’s a great success – $100 million exit. And here’s what happens.

For her million shares, Jill gets $40 million. The employees’ half-million shares net them $20 million. And Jack? He gets a call one afternoon to be told that, for sitting on his duff for the past five years, he’s worth a cool $40 million, same as Jill.

Obviously something’s wrong with this picture. The problem is that stock grants without vesting are a lousy way to reward behavior.  Value is awarded in a big block at the beginning, even though the contribution is (or isn’t) provided over a long period of time. This is like paying someone four years worth of salary in a lump sum on his or her hire date.

The most obvious solution, of course, is to not issue all the stock at once but instead, to treat stock like salary – give it out in small chunks over time. Unfortunately this is a terrible idea. As time goes on, the stock gets progressively more valuable, and the tax impact to the founders gets worse and worse. Plus the strike price, if they are options, gets higher and higher.

As I’m sure you’ve gathered by now, the solution is – vesting. If up-front stock grants are a hack to minimize taxes, then vesting is the hack to the hack. It’s the tweak that keeps incentives aligned. The founders get their stock at the beginning in a big whack, but the company has the right to take it back for a negligible amount of money (the “repurchase agreement”). And as time goes on, that right erodes, so the net is the same. The founders’ stake grows over time, while still letting the founder keep ownership of the stock from a legal standpoint as it appreciates, allowing long-term capital gains treatment, favorable initial tax treatment, voting rights, and all that jazz.

“But wait!” the novice founder cries out. “If I build lots of value and sell the company after just a year or two, I get the shaft! My stock won’t be vested, and I’ll lose out!” Yes you will, young Padawan, unless you include acceleration in your vesting schedule. Acceleration is the final hack to the hack, which brings the Force back in to balance.

Acceleration comes in two flavors. There’sAcceleration on change of control,” (aka single-trigger acceleration), which means that if the company is sold, some or all your stock vests. Yay! Then there’s “Double-trigger acceleration,” which means that if the company is sold, AND you’re fired, then some or all of your stock vests. Sort of yay!

The former is obviously better for the acceleratee. But keep in mind that a deal may be hard to get done, if the acquirer knows that all the stock incentives to stick around disappear when the deal closes.

Double-trigger, or a mix of single- and double-, is often a nice compromise to keep the company marketable, while rewarding people for their hard work. This is often more of an issue for employees, who join later, and will still be vesting when a transaction happens, and who can’t leave en-masse if the transaction is to go through. For reasons of company lifecycle timing, founders are usually fully vested by the time a deal happens.

Regardless, the important thing is this: Founder vesting is founder friendly, the exact opposite of what most people think. It keeps the balance between working founders, who build the company up, and absent founders, who leave early. You want it. Don’t fight it. In fact, don’t wait for an investor to tell you that you need it – get it done when you incorporate. Just remember to pair it with acceleration on change of control!

And now, some suggestions for vesting schedules.

  • Use a four-year vesting cycle for founders, the same as you eventually will for employees.
  • Put founder vesting in place before you start to raise money. Investors will be impressed that you know what you’re doing. If your vesting terms are reasonable, they’ll be accepted without argument. And when you’re negotiating terms, it’s better to have fewer things that matter to you on the table.
  • If there’s a “trial period,” for example, people working part-time for a few months, then consider a cliff that expires after the trial. That means the first vesting doesn’t occur until the trial period is over, and then you vest a lump of however much you would have received anyway. Stock is best used for people who are totally committed, so the stock accumulation shouldn’t kick in until the commitment does. The obvious exceptions to this are strategic advisers, who will only ever be partially committed but where that level of commitment is all the company wants and needs.
  • If there’s a meaningful commitment of resources in advance of the vesting agreement, it’s reasonable to “fast forward” the agreement by an appropriate amount. For example, if you’ve been working full time for a year before vesting is in place, it would not be unreasonable to start with one-quarter of your stock vested already and put the rest on a three-year schedule.
  • Stock that is in payment for resources doesn’t need to vest.  For example, if the company is split 50/50, but then one founder puts in $100,000 in exchange for 10 percent, then the 10 percent that they get should not vest. Since the value is delivered up front, the stock should be too. (Obvious corollary: investor stock is granted outright and does not need to vest)
  • For founders, accelerate 50 percent of the remaining unvested stock on change of control (single-trigger), and 100 percent of the rest double-trigger. This is reasonable and fair, and makes it very unlikely that you’ll leave much value on the table.
  • It is generous, but not unreasonable, to consider double-trigger acceleration for some or all of your employees. However, you may cause yourself problems during M&A down the road – check with your lawyer first.
  • Try to avoid single-trigger acceleration for non-founders whenever possible. Not only is it sure to cause issues during M&A (the acquirer will be worried that everyone vests & leaves after the transaction), but an acquirer may make changing these terms a condition of a deal, which just leads to ugly.
  • Get the legal paperwork for your stock agreements sooner rather than later, to start the capital gains clock ticking. This can easily be a seven digit difference if you happen to have an early exit (ask me how I know).
  • File your 83(b) elections the day your incorporation goes through. You have 30 days to do it, and then you’re screwed forever. If you’re not sure if this applies to you, ask your lawyer. If they’re not sure, fire them and hire someone else. This is one of the most common, avoidable, and expensive mistakes founders make.
  • One last thing: The founder vesting arguments assume multiple founders. If you’re a solo founder, you might skip founder vesting, and hope no one notices…

Founder vesting may sound terrible. But when paired with reasonable acceleration, it’s a good thing for everyone.