- Merrill Lynch, the largest full-service stock brokerage in the world, introduced discount online trading
- IBM announced that it would stop selling PCs through retailers in the U.S. and would sell PCs only over the web
- Encyclopedia Britannica placed its encyclopedia for free on the Internet, swapping two centuries of book sales for an online advertising strategy
- Microsoft and Intel became the first "new economy" companies, and the first Nasdaq issuers, to be included in the Dow Jones Industrial Average
- 289 iPOs raised $24.66 billion in 1999, compared to 42 iPOs raising $1.96 billion in 1998
- iPOs represented 60% of the total number of IPOs in 1999, compared to 14% of IPOs in 1998
- the average iPO ended the year 266% above its offering price, compared to an average appreciation during 1999 for non-Internet related IPOs of only 59%; the Nasdaq Composite was up 86% in 1999 and the Dow increased 25% for the year
- the average iPO closed 90% above its offering price on its opening day
- of the 30 largest first-day gains in IPO history, 29 occurred during 1999, and nearly all were iPOs
Click and Mortar
- In May 1999, eBay, founded in 1995, acquired Butterfield & Butterfield, founded in 1865 and now the third largest auctioneer of fine and decorative art and collectibles in the U.S., for $235 million in eBay stock.
- Wit Capital, an Internet investment banking and brokerage firm established in 1996, acquired SoundView Technology Group, an investment banking firm founded in 1979, for $310 million (paid mostly in Wit stock) in January 2000.
- In January 2000, Charles Schwab, the largest discount online brokerage, agreed to acquire U.S. Trust, a money management firm founded in 1853, for $2.9 billion in stock in order to create a full-service brokerage and wealth management company.
- In the biggest M&A transaction in history, America Online agreed in January 2000 to acquire Time Warner, the largest media and entertainment company in the world with roots dating to the 1920s, in a stock merger valued at $350 billion.