The billionaire might be making more music investments like AEG.

John Malone, the billionaire investor most responsible for cable TV's presence in more than 100 million U.S. homes today, is doubling down on his two music-led investments and could be interested in making another bet or two if the right music asset comes to market.

Most notably Malone is very close to taking full control of SiriusXM after the company increased its stake to 49.6% in recent days. Assuming regulatory approval, Liberty Media should become the controlling holder of the U.S. satellite radio company, a monopoly, which has more than 22 million subscribers and forecasts adding 1.8 million new subscribers by the end of the year.

Malone's financial engineering and risky bets are legendary in the business world, but the deal to take a 40% stake in Sirius is, by his own admission, one of his best. At the peak of the financial crisis in 2009, a desperate Mel Karmazin, CEO of Sirius, needed a $530 million loan to help the company avoid bankruptcy. Malone lent Sirius the cash at an eye-watering 15% and attached warrants that eventually gave Liberty Media a 40% stake in the satellite radio company. Today 40% of SiriusXM is worth $4.2 billion.

Malone also now owns more than one-quarter of Live Nation Entertainment, the world's largest concert promoter and leading ticketing company, and he's secured an option to increase that holding to 35%. Malone came to own Live Nation through his original holding in Barry Diller's IAC/InterActiveCorp before it spun out to Ticketmaster.

Liberty Media chief executive Greg Maffei has led the push to make the holding company more strategic in its acquisitions and getting rid of small, non-controlling stakes.

"The music space is a great space and there will always be an enduring interest in music," Malone says. "[SiriusXM and Live Nation] have found interesting ways to grow. Just because music is popular doesn't always mean it's possible to make money from it."

This is one reason why Malone and Maffei are slightly indifferent to the idea of investing in music assets because they're music assets. They're nothing if not conscious of valuation metrics even as many other financial investors have vied to buy up song publishing catalogs, beloved for their steady cash flow and diversified revenue streams.

"We've looked at some of the publishing businesses, but candidly, those already in the business have way more synergies than we do to be able to justify paying those valuations," Maffei says.

Liberty Media and Malone aren't sentimental about their investments.

"Malone likes the subscription business of Sirius, which generates a lot of free cash flow, while Live Nation is a market leader with a ticketing business that generates plenty of cash," says Brett Harriss, an analyst at Gabelli & Co., which owns shares in both. "It probably says less about their love for music but more about these businesses ability to generate cash and maintain sustainable barriers to entry. They're not about to buy a record label."

One asset on the market is Phil Anschutz's Anschutz Entertainment Group, whose assets include Los Angeles' Staples Center and AEG Live, the No. 2 live entertainment business after Live Nation. Reports have put valuations of AEG assets at up to $10 billion.

Maffei says Liberty Media will have a look at the assets but is realistic about the likelihood of having to deal with a lot of regulatory pushback from rivals if it made a serious move.

"Phil Anschutz has built a very interesting portfolio of businesses and assets, some of which fit in with our existing businesses," Maffei says. "But I'm not sure if we'll have the ability, or rather be allowed to buy some of those assets that fit in with Live Nation because of the regulatory scrutiny which it already faced during the Ticketmaster merger."

And what if AEG were to break up some of the assets for sale? "I don't know what they're going to do," Maffei says.

Questions? Comments? Let us know: @billboardbiz

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