In 2000, even as my dot-com era startup was burning through its remaining capital, I started work on this little card game. I made a somewhat desultory effort to find a publisher for it, without success, and eventually released it as a free download.
You play as a great venture capital firm (Eine Kleine Perkins, Flathead Partners, noidealab!, Arse Alliance, and Gossamer Venture Partners), investing in start-ups and trying to take them public before the inevitable crash. Companies are founded by playing "business plan" cards, of which there are thirteen, for firms like Muttscape, Thiefster, and iPotempkinVillage; a company is "funded" when one of the players leads an investment round by placing money on the business plan card. Every turn, companies have to pay their burn-rate out of that money, or go bust.
You improve the value of a company (but also generally increase its burn rate) by "attaching" cards representing entrepreneurs, strategic alliances, buzzwords, or positive press. Initially, a company has to consist of at least six cards (the business plan, plus five attachments) to go public, but as the game goes on, the "IPO limit" decreases as the dot-com mania progresses (until, by the end of game, even a newly-funded company with no traction might be able to go public). Sooner or later, however, the "Dot Crash" card comes up, any all companies that haven't gone public yet are toast, and any unliquidated investments are history.
Cynical, maybe a little too random for serious gamers, but kind of fun, I think. The links are to the rules and cards; unfortunately, I'm not a graphic designer, so they're basically just text. You'll also need some Monopoly money, dice, and some counters to represent share ownership by the different players.