Valuations were a topic of robust conversation — and speculation — at the gathering of nearly 450 executives. One session sought to answer the question, Is there an enterprise bubble? Other hot topics included the future of media and the role of disrupters like Aereo, which offers network TV via the Net but does not pay broadcasters a transmission fee. Neil Ashe, CEO of global e- commerce for Wal-Mart Stores, promised that mobile tech would transform in-store shopping.

Amid all the talk of transformation, transparency, and innovation, speakers doled out practical advice on how to manage business in the fast-changing tech world. Chesky counseled upstarts to forge relationships with executives like Donahoe. “I’ve always [felt] I’ll be successful as long as I have the humility to take advice from people who have been where I hope to be one day.” Of course, it helps to find gurus you really like. –Stephanie N. Mehta

Uber: Big plans beyond hailing rides

It’s been three years since Travis Kalanick co-founded Uber to call up cabs and limos via smartphone. The startup has since rolled out in 35 cities, including hotspots such as Amsterdam, Paris, and Seoul. A pop-up Uber Aspen was launched for Fortune’s conference in just three days. But Uber is shaping up to be more than just a car service. At Brainstorm, Kalanick revealed he had held informal discussions with a large e-commerce company about utilizing drivers’ downtime for same-day delivery, for example. Uber is currently raising a round of funding at a rumored multibillion-dollar valuation. Kalanick dodged a question about that figure before saying, “The multiples that you see in the public market around companies that are growing 50% or 40% … and we could come in — well, shoot, I’m getting stuck. Shit.” He stopped himself there and the room exploded with laughter. –Jessi Hempel

Television: The future is interactivity

Nancy Tellem, president of Microsoft’s Xbox Entertainment Studios, has seen the future of TV — and she gave Brainstorm attendees a peek. Tellem runs the division responsible for creating original programming for the company’s popular games console. (Think Netflix’s House of Cards.) Her first project is a program based on the Halo games — not surprising considering the franchise has generated more than $3 billion in sales since its initial release in 2001. Microsoft (MSFT) is working with director Steven Spielberg on the show. “The next step was to go deeper in narrative into the Halo mythology,” Tellem explained. She described a more interactive viewing experience. Does that mean traditional television will die? Not exactly, according to the former CBS executive. “The package is going to change; you’re going to see à la carte options,” she said. “But TV is not going anywhere.” –Matt Vella

Murdoch: Not afraid to get things wrong

James Murdoch, son of mogul Rupert and deputy chief operating officer of 21st Century Fox, is not afraid of his mistakes. Speaking at dinner on the first night of this year’s conference, Murdoch seemed, if anything, wary of not taking enough missteps. “If you become paralyzed by your failures, you won’t grow,” he said. The obvious example: a phone-hacking scandal that set the stage for the splicing of the Murdochs’ lucrative television and film properties from less exciting old-media holdings. But Murdoch, 40, painted the split — News Corp (NWS). will consist of newspapers; 21st Century Fox, film and TV — as rational. “Each business makes much more sense separately,” he said. He has high hopes for TV in particular. “The business is going through a creative renaissance,” he said. “It’s a great period,” he added, before concluding that the days of “middle of the road” shows are over. –M.V.

Talking hip-hop and tech: Two forces changing American Culture

When Ben Horowitz, co-founder of Andreessen Horowitz, and Steve Stoute, CEO of Translation Advertising, got onstage, it wasn’t surprising that they kept returning to hip-hop’s relationship to tech. Horowitz is a die-hard fan, and Stoute has worked with the likes of Mary J. Blige and Eminem. Stoute said the mega-partnership between Jay Z and Samsung shows that marketing is changing. (It worked, he said: “Twenty million people went to go download the album on July Fourth.”) Horowitz talked about how prominent entrepreneurs influence culture. “Look at the old pictures of Bill Gates, and look at the new pictures of Jack Dorsey,” he said. “One was outside the culture, and the other is inside the culture.” –Brandon Southward

Univision is gunning for supremacy

Univision president Cesar Conde discussed the company’s rapid expansion — it has 14 cable and broadcast networks. The challenge is hanging on to viewers when there is so much other content besides traditional television. “It’s been an important growth trajectory,” said Conde, who plans to continue expansion into English-language channels. “It’s equally important for us as broadcast networks to constantly reinvent ourselves in the era we are living in now.” –Kurt Wagner

Gen. Stanley McChrystal on life after the military

Stanley McChrystal says he knew little about business when he left the military in 2010. He’s learned they have much in common. McChrystal, who now runs a consulting firm, is sharing these lessons with the likes of HP (HPQ). His main liaison? Todd Bradley, HP’s executive vice president of strategic growth initiatives. Both recounted operating in a less-than-supportive atmosphere. “Your responsibility is to dilute that ambivalence to create certainty,” Bradley concurred. –Miguel Helft

Startup Idol AnyRoad Is bringing tour guides into the 21st century

When Daniel and Jonathan Yaffe get worked up, they take turns speaking for each other. The effect isn’t so much finishing each other’s sentences as excitedly adding clause after clause.

But the brothers’ enthusiasm earned their startup, AnyRoad, the title of 2013 Brainstorm Tech Startup Idol. Launched earlier this year, San Francisco-based AnyRoad is a website for tour guides to list their services: a hike through Rio de Janeiro or a Tokyo sake tasting, for instance. The startup makes money by taking a small commission on tour fees. The Yaffes, San Diego natives, figure they are tapping into a $16 billion global market; just 5% of professional tour guides have websites.

Not surprisingly, the founders like to travel: Jonathan has been to 85 countries; Daniel, to 46. After UC Berkeley, Jonathan, now 31, trekked through Latin America, living like a nomad until he ran out of money. He eventually made his way to Japan, where he founded the progressive, Tokyo-based KAIS International School. Daniel, now 28, launched a magazine about alcohol, sold it, then penned a travel book about whiskey. “Drinking and traveling — how could I say no?” he jokes.

After years of travel and talking to local guides, the Yaffes started AnyRoad with $60,000 of their own money. The site is testing features to filter suggestions by type of food served, duration, and child-friendliness. The now three-man team plans to expand into Greece and Korea, and wants to be in 15 cities by next year. Come 2015, they want AnyRoad to be available in 10 languages.

AnyRoad won out over contestants with ideas ranging from helping students locate potential friends and dates nearby to crunching through the mounds of data created by intelligence agencies. Each startup was allowed five minutes to pitch its idea for a chance to win an office setup, courtesy of Herman Miller, maker of the Aeron chair, found in most Bay Area startups.

Ultimately, the Yaffes’ energy swayed judges Marissa Mayer, Jeff Richards, Dana Settle, and Casey Wasserman. “I like the idea of ‘software-eats-travel-guide booking,’ ” admitted Yahoo CEO Mayer. “And I think, in terms of local and travel, it’s about how familiar you are with the market. I like that you’ve actually been to these places.” –JP Mangalindan

Read more coverage of Brainstorm Tech from around the web

TechCrunch
All Things D
New York Times
PCMag.com
Variety
CNET

This story is from the September 2, 2013 issue of Fortune.