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"We're prepared to offer you a salary only slightly lower than what you're making now," the hiring manager across the table from me at Yahoo had said, "and"—he paused dramatically—"one thousand stock options." I wasn't blown away. Yahoo's stock was already at fifty dollars a share. If it went to a hundred, I would make fifty thousand dollars. But if the stock dropped and never reached fifty again, my options would be "underwater" and hold no value.

For tax reasons, it's advisable to buy your options at the time they're issued, which would have meant putting fifty thousand dollars of my own money on the table: fifty thousand dollars I would never see again if the company took a dive. Plenty of dot-coms did go under in the big bust the following year, leaving little in their wake but suburban bathrooms wallpapered with worthless stock certificates. And even though I would be putting out the money up front, I wouldn't actually take ownership of the options immediately. I would take possession or "vest" on a schedule that began with a "cliff" of one year, meaning that not one share would actually belong to me until I had completed twelve months at the company. Then I would earn the rest of my shares month by month over the next three years, at which point I would be fully vested. Until the company went public, however, I couldn't sell the stock to anyone but the issuer.*

When I read my offer letter from Google, I thought there must be a typo. I was prepared for the pay cut, but the comma was in the wrong place on the number of options granted. It was an order of magnitude larger than I expected. Google was offering me a large stake, but I would have to bet it all on the company moving into the black. If Google did well, so would I. Salary? That was just a free drink and a complimentary crab cake while I waited for the roulette wheel to stop spinning and my chips to come in.

I've never been a numbers guy, but no matter how I did the math, the results looked pretty good. The board would meet within a month to approve stock grants to new employees and set the price at which my shares would be valued. I had decided to buy the options to avoid the tax penalty and now I waited to find out what I would have to pay for them.

The email headlined "Strike price" pinged into my mailbox. I opened it. The board had approved my offer at a share price of twenty. Twenty cents. It felt a little high, given the company's lack of revenue or a proven business model, but not unreasonable. Unfortunately, I was broke. Even at twenty cents a share, I couldn't afford to buy my options. My capital was tied up in a significant stake I'd taken in plush toys and flame-retardant pajamas. I would have to borrow money from my parents.

Kristen considered my decision on its merits.

"You want to borrow money?" she lovingly inquired. "To buy worthless shares of a company that doesn't have any revenue? Are you out of your mind? Can't you buy the shares later? Will you get the money back if they go out of business? You know, the car keeps stalling and we need a sewer line cleanout." Then she said, "Fine. Do what you want. Are you sure you really want to do this?"

My parents were equally skeptical, but they were my parents. They dug deep into their retirement savings to lend me the money, though I'm sure they believed it would go flush, right down the toilet.

So I bought the shares and waited and watched each month as they ticked up a few pennies at the board meetings. It was all play money since there was no way to cash out. Yet I found it hard to resist calculating my worth, even if it was imaginary. I never spoke of it at work. It was very bad form to discuss compensation within the company. We were all there for the love of technology and to radically improve the world. Really, we were. Seriously. Mostly.

One month the board met and raised the stock a dime. Suddenly I could repair the backyard fence or re-pipe the bathroom. I couldn't actually