"We were in discussions with both Uber and Lyft, but when we evaluated both companies, we thought that Lyft is a better entry point for us. Because at that time, Uber's price was at a plateau of its highest height. So we invested in Lyft, and we have a very good relationship with .... the management," Alwaleed said in an interview on CNBC's "Squawk Box. "But Uber still is a great company, obviously, and Uber is the company that began with this whole idea of shared rides. Our choice was to go with Lyft but it doesn't mean that Uber is not good."
Alwaleed, who runs Kingdom Holding, made his comments on the heels of a Wall Street Journal report that another Saudi fund, state-owned Public Investment Fund, was struggling to deal with a disappointing investment in Uber.
Uber lost key staffers in operational roles this year, including co-founder and CEO Travis Kalanick. The company is recovering from a damaging workplace culture investigation and a series of scuffles with regulators.
Uber's latest challenge has been to smooth things over with London regulators, who stripped the company of its license to operate in London. Alwaleed said he's confident the company can recover.
"We have a new CEO there, just appointed, and I think we should give him the time to get the company back on track. Travis was a genius in what he did, he is very smart," Alwaleed said. "Uber is at the vanguard of this project. Uber's going to make it for sure, no doubt about that."
Uber and Lyft, like many other companies, are looking at new ways to approach transportation. As more companies lean toward "the Tesla path" of electric vehicles, Alwaleed said Saudi investors are looking to diversify away from oil-related assets.
Alwaleed's reach extends far beyond transportation technology — he's also a prominent investor in Twitter. That company competes for advertising dollars with the like of Google and Facebook, but hasn't had the same quick ascent to dominance in the industry.
"Our investment in Twitter is part and parcel of a plan whereby Kingdom Holdings is moving from the old investments that we had to the new investments, like JD.com in China, like Twitter, Lyft, and Careem, which is another ride-hailing [company] in the Middle East," Alwaleed said. "We are very optimistic about that, obviously —Twitter. It's not going to be easy because now they're facing some difficulties. But our entry point was very reasonable so right now it's holding our breakeven point. So any good news from Mr. Jack Dorsey and his team at Twitter will reflect very much on Twitter."
Alwaleed said he thinks Twitter's rivals are monopolies. But while he has wound down his stake in Apple, he said he doesn't agree with calls for more regulation on big tech.
"Clearly, behemoth companies like Google, Amazon, Facebook, Apple, Microsoft — these are giants," Alwaleed said. "We have seen a lot of voices in the United States where we need to regulate what's happening on Facebook, and to a lesser extent on Twitter. ...We've seen in the '90s and early 2000s they were trying to break up Microsoft and it failed completely. I think it's a free market, there should be free competition."
Alwaleed also rubs shoulders with technology titan and Microsoft co-founder Bill Gates. In addition to philanthropic work with the Bill and Melinda Gates Foundation, Alwaleed helps Gates run luxury lodging brand Four Seasons.
In July, The Wall Street Journal reported that the Four Seasons management struggled to get on the same page internally. But Alwaleed told CNBC on Monday he's in almost constant communication with Gates.
"The media blew this out of proportion," Alwaleed said.