I was pretty excited about Web apps, which were a new thing then. (We planned eventually to make a whole suite of them; Viaweb Store was just the first.) So I probably would have worked on those in some way. Maybe I would have written some sort of general platform for building them, and/or written a book about that topic.
If writing web apps in other languages isn't still painful where have other languages/frameworks caught up?
The format of Ask PG seems to work pretty well. A mix of technical questions regarding YC applications, changes to HN, and interesting business questions tend to get deeper answers than is common within the limits of AMA.
There's still time for that. The current solutions leave much to be desired (although they're slowly moving in the right direction).
Following from that, if pg wasn't a "winner" there is very little to differentiate him from what 1,000,000 others have tried and failed. Circumstance and context are a frighteningly arbitrary decider, and therefore I don't think this question is particularly meaningful.
[edit: this is not to suggest that dumb luck alone is enough to create a success, it's just that intelligence and tact alone are often not enough to create success either]
discussing just such a hypothesis:
Where do you get the "success that has recently started to wane"? Berkshire Hathaway has continued to outperform the market, check 5 and 10 year charts here for example: http://www.fool.com/quote/NYSE/berkshire-hathaway-inc/BRK-A/....
Obviously they haven't had the same level of outsized successes, simply because BRK has grown much bigger, and it's harder to get good returns on larger amounts of capital. But there's no way you can conclude from Berkshire Hathaway's performance that it was just luck after all.
Also, see cs702's comment about how Warren Buffett identified 7 investors in 1984, all of whom went on to outperform the market: http://news.ycombinator.com/item?id=4476166
"The other catch is that the payoff is only on average proportionate to your productivity. There is, as I said before, a large random multiplier in the success of any company. So in practice the deal is not that you're 30 times as productive and get paid 30 times as much. It is that you're 30 times as productive, and get paid between zero and a thousand times as much. If the mean is 30x, the median is probably zero. Most startups tank, and not just the dogfood portals we all heard about during the Internet Bubble. It's common for a startup to be developing a genuinely good product, take slightly too long to do it, run out of money, and have to shut down."
With two such random linkages in the path between startups and money,
it shouldn't be surprising that luck is a big factor in deals.
And yet a lot of founders are surprised by it.
It's not on this topic but it definitely hits on it
To me it feels like any of those problems would require the world to be quite different from how it is.
There are a million possible failure cases for any startup, including a large number that are for all practical purposes out of your control - a car accident could disable a key participant, a better competitor could suddenly pounce on the scene, fraudsters could decide to make you a target, etc. With all due respect to PG, you don't have to change the world much to see Viaweb fail. Even with hindsight.
"If you can just avoid dying, you get rich. That sounds like a joke, but it's actually a pretty good description of what happens in a typical startup. It certainly describes what happened in Viaweb. We avoided dying till we got rich."
"There is an art, it says, or rather, a knack to flying. The knack lies in learning how to throw yourself at the ground and miss."
I think with respect to startups the quote is more than just funny, it captures the bravery and apparent foolishness but great rewards of the endeavor.
It's also a perfect description of how orbital mechanics work - the Moon is actually falling down towards us, it's just moving so fast in the other direction that it constantly misses the Earth :).
I agree with forgotusername's opinion about the luck plays a good part in life, but as long as the Viaweb's concerned, the luck had its minimal share because I still remember in one of pg's articles he was talking about how frequently they have written their code base in order to serve a user experience better than the competition. That's hardly got anything to do with luck.
And if you've ever read all his articles, you might have spotted sections talking about when and how the luck has been playing really impressive role; and there you got it: In the case of Bill Gate's Microsoft. How it suddenly became a multi billion dollar company almost overnight is plain luck.
Also when you consider for how much Viaweb was sold, which was about $50M, and compare it to other sales most of them as high as ~$1B, again there is no luck to be talked about.
Edit: essay I had in mind: http://www.paulgraham.com/avg.html
Do you mean not getting acquired, or never making any money or getting any traction?
If the former, he (I would surmise) would've been a lifestyler.