Paul Graham - Essays

[7] Options have largely been replaced with restricted stock, which amounts to the same thing. Instead of earning the right to buy stock, the employee gets the stock up front, and earns the right not to have to give it back. The shares set aside for this purpose are still called the "option pool."

[8] First-rate technical people do not generally hire themselves out to do technical due diligence for VCs. So the most difficult part for startup founders is often responding politely to the inane questions of the "expert" they send to look you over.

[9] VCs regularly wipe out angels by issuing arbitrary amounts of new stock. They seem to have a standard piece of casuistry for this situation: that the angels are no longer working to help the company, and so don't deserve to keep their stock. This of course reflects a willful misunderstanding of what investment means; like any investor, the angel is being compensated for risks he took earlier. By a similar logic, one could argue that the VCs should be deprived of their shares when the company goes public.

[10] One new thing the company might encounter is a down round , or a funding round at valuation lower than the previous round. Down rounds are bad news; it is generally the common stock holders who take the hit. Some of the most fearsome provisions in VC deal terms have to do with down rounds-- like "full ratchet anti-dilution," which is as frightening as it sounds.

Founders are tempted to ignore these clauses, because they think the company will either be a big success or a complete bust. VCs know otherwise: it's not uncommon for startups to have moments of adversity before they ultimately succeed. So it's worth negotiating anti-dilution provisions, even though you don't think you need to, and VCs will try to make you feel that you're being gratuitously troublesome.

Thanksto Sam Altman, Hutch Fishman, Steve Huffman, Jessica Livingston, Sesha Pratap, Stan Reiss, Andy Singleton, Zak Stone, and Aaron Swartz for reading drafts of this.

Does "Web 2.0" mean anything? Till recently I thought it didn't, but the truth turns out to be more complicated. Originally, yes, it was meaningless. Now it seems to have acquired a meaning. And yet those who dislike the term are probably right, because if it means what I think it does, we don't need it.

I first heard the phrase "Web 2.0" in the name of the Web 2.0 conference in 2004. At the time it was supposed to mean using "the web as a platform," which I took to refer to web-based applications. [1]

So I was surprised at a conference this summer when Tim O'Reilly led a session intended to figure out a definition of "Web 2.0." Didn't it already mean using the web as a platform? And if it didn't already mean something, why did we need the phrase at all?

Tim says the phrase "Web 2.0" first arose in "a brainstorming session between O'Reilly and Medialive International." What is Medialive International? "Producers of technology tradeshows and conferences," according to their site. So presumably that's what this brainstorming session was about. O'Reilly wanted to organize a conference about the web, and they were wondering what to call it.

I don't think there was any deliberate plan to suggest there was a new version of the web. They just wanted to make the point that the web mattered again. It was a kind of semantic deficit spending: they knew new things were coming, and the "2.0" referred to whatever those might turn out to be.

And they were right. New things were coming. But the new version number led to some awkwardness in the short term. In the process of developing the pitch for the first conference, someone must have decided they'd better take a stab at explaining what that "2.0" referred to. Whatever it meant, "the web as a platform" was at least not too constricting.

The story about "Web 2.0" meaning the web as a platform didn't live much past the first conference. By the second conference, what "Web 2.0" seemed to mean was something about democracy. At least, it did when people wrote about it online. The conference itself didn't seem very grassroots. It cost $2800, so the only people who could afford to go were VCs and people from big companies.

And yet, oddly enough, Ryan Singel's article about the conference in Wired News spoke of "throngs of geeks." When a friend of mine asked Ryan about this, it was news to him. He said he'd originally written something like "throngs of VCs and biz dev guys" but had later shortened it just to "throngs," and that this must have in turn been expanded by the editors into "throngs of geeks." After all, a Web 2.0 conference would presumably be full of geeks, right?

Well, no. There were about 7. Even Tim O'Reilly was wearing a suit, a sight so alien I couldn't even parse it at first. I saw him walk by and said to one of the O'Reilly people "that guy looks just like Tim."

"Oh, that's Tim. He bought a suit."

I ran after him, and sure enough, it was. He explained that he'd just bought it in Thailand.

The 2005 Web 2.0 conference reminded me of Internet trade shows during the Bubble, full of prowling VCs looking for the next hot startup. There was that same odd atmosphere created by a large number of people determined not to miss out. Miss out on what? They didn't know. Whatever was going to happen-- whatever Web 2.0 turned out to be.

I wouldn't quite call it "Bubble 2.0" just because VCs are eager to invest again. The Internet is a genuinely big deal. The bust was as much an overreaction as the boom. It's to be expected that once we started to pull out of the bust, there would be a lot of growth in this area, just as there was in the industries that spiked the sharpest before the Depression.

The reason this won't turn into a second Bubble is that the IPO market is gone. Venture investors are driven by exit strategies. The reason they were funding all those laughable startups during the late 90s was that they hoped to sell them to gullible retail investors; they hoped to be laughing all the way to the bank. Now that route is closed. Now the default exit strategy is to get bought, and acquirers are less prone to irrational exuberance than IPO investors. The closest you'll get to Bubble valuations is Rupert Murdoch paying $580 million for Myspace. That's only off by a factor of 10 or so.

Does "Web 2.0" mean anything more than the name of a conference yet? I don't like to admit it, but it's starting to. When people say "Web 2.0" now, I have some idea what they mean. And the fact that I both despise the phrase and understand it is the surest proof that it has started to mean something.

One ingredient of its meaning is certainly Ajax, which I can still only just bear to use without scare quotes. Basically, what "Ajax" means is "Javascript now works." And that in turn means that web-based applications can now be made to work much more like desktop ones.

As you read this, a whole new generation of software is being written to take advantage of Ajax. There hasn't been such a wave of new applications since microcomputers first appeared. Even Microsoft sees it, but it's too late for them to do anything more than leak "internal" documents designed to give the impression they're on top of this new trend.

In fact the new generation of software is being written way too fast for Microsoft even to channel it, let alone write their own in house. Their only hope now is to buy all the best Ajax startups before Google does. And even that's going to be hard, because Google has as big a head start in buying microstartups as it did in search a few years ago. After all, Google Maps, the canonical Ajax application, was the result of a startup they bought.