His father bought and sold cable companies. Craig and his 3 brothers were given one cable company in Washington state in trust. That one cable company was expanded and leveraged to make McCaw rich enough to buy lots of spectrum from the FCC. Then in 1986, "MCI sold its cellular and paging operations to McCaw for $122 million and McCaw Cellular emerged as the industry leader." One more piece to the puzzle was added to the tune of $3.5 billion when McCaw outbid BellSouth for control of LIN Broadcasting in 1989. Now McCaw had a nationwide network that he sold to AT&T for $11.5 billion in 1994.
Wireless technology was first developed by AT&T Labs in 1947 for law enforcement. Cellular was yet one more technology that AT&T Labs pioneered but AT&T failed to bring to market.
In 1998 - four years after selling to AT&T and becoming its largest shareholder - McCaw still had two publicly traded companies: Nextel and NextLink. According to a 1998 Forbes article, "The former is a mobile dispatch company with a checkered investment past, it uses a unique bandwidth and a set of radio phones created by Motorola, which were initially sold to truckers and cab companies." McCaw owned 30% of Nextel then. It is amazing that he won enough FCC spectrum auctions for Nextel to have a nationwide service footprint - after winning spectrum auctions for a nationwide network that was sold to AT&T.
"The latter is a small, competitive local exchange carrier (CLEC) created to install, maintain, manage and sell fiber-optic cable telephony services to businesses. Add one more piece to this collection – CablePlus – a small company that actually installs fiber optic cable networks and connections, and the McCaw telephony strategy comes into view: Telecommunications services anywhere, all provided by McCaw-controlled entities." Nextlink merged with Concentric to become XO, which after $7 billion in debt, went bankrupt in 2002, when McCaw separated from the company.
McCaw went to prep school with Bill Gates, who he partnered with "in Teledesic (where each started out with 45% ownership, since diluted), a satellite broadband (64 megabits of bandwidth per second–equal to 10 full motion video feeds) service, looks a lot less shaky. The idea is to put 288 satellites into low earth orbit (LEO) at a price tag of about $9 billion."
Then McCaw founded Clearwire. Here's that story:
"In 2003, McCaw signed a long-term lease agreement with a U.S.-based Spanish language broadcaster that held the country's largest 2.5 GHz license. In the next two years, McCaw would acquire nearly 1,000 such leases -- roughly 85 percent of the 2.5 spectrum band -- at an estimated 30-year cost of $5 billion. In 2005, the Federal Communications Commission deregulated the 2.5 band to permit its use for wireless broadband, and the value of McCaw's leases skyrocketed. His $5 billion investment was soon worth anywhere from four to ten times that much." [source]
Serial Entrepreneur indeed - all in telecom.