I dunno...I think the first bubble was a boom through 95, 96, and 97. Netscape, Yahoo, Amazon, Craigslist, EBay all had real products that made money and changed how people did business. It didn't get to be bubblicious until about 1998, when people started getting venture funding for pet stores.
It was right around 97 that people started crying "bubble!", and I think that we're at about the same point in the economic cycle that we were then. Tail end of the midcycle phase. Assuming the housing bust doesn't tank the economy, the real bubble years are still ahead.
If we are in the midcycle phase, it's still a good time to start a company. Capital's not flowing freely enough that anyone can get funded, so those who bootstrap good ideas now stand to profit handsomely when money managers seek to pull all their capital out of the failing real estate market and into the stock and startup market.
It's not time to worry until VCs start giving out $15M to any idiot with a business plan. You don't want to be that idiot.
The fine point here is: there is a difference between a boom and a bubble. Boom == increase in activity supported by actual innovation. Bubble == increase in activity based on marketing fluff or other unsustainable models.
PG talks quite a lot about this kind of thing; in particular, he points out that a boom can sustain for as long as there is innovation (wealth-creation) to support it, and that there is no reason the economy can't support, say, 1000 people working on startups rather than 1000 people working for IBM.
Ok, isn't Web 2.0 a similar marketing fluff? I understand with all similarities it's not the same. I'm sure it is much better now, but add one more new factor, like the failure of Windows Vista for example, and you may have that critical mass for a new collapse.
"add one more new factor, like the failure of Windows Vista for example, and you may have that critical mass for a new collapse"
Forgive me, but I don't see the connection. How would the failure of Windows Vista do anything but help applications that run on the web? I can imagine some large things that could hurt this boom (economic collapse, maybe), but nothing small.
Web 2.0 has a lot of hype right now, but that doesn't make it marketing fluff. There is real substance here (and real profits, real innovation, and real users).
In contrast: here is a quick story about a company that I interviewed with in 1998. I don't remember the name; they were located South of Market in a really nice loft with lots of brick, glass, and chrome. Free lunch every day, free beverages, lots of perks. The business model: we are going to get your website's customers to fill out surveys. You are going to pay us for this. We will get the customers to fill out surveys by rewarding them with frequent-flier miles. I remember three things about this company, years later: how nice their loft was, how stupid and convoluted their business model was, and how arrogant they seemed to be about it. They acted like they were already a success.
In contrast, btw, the startup I did join was operating out of a cluttered office in Palo Alto that they'd got a really good deal on. Junk was everywhere, and the Founder/CEO asked me if I minded. I told him, "hey, it looks like a real startup." That company is still in business today. Frequent-Flier-Miles-for-Surveys, Inc: not so much.
Truth is, this guy needs to read PG's essays.