Last week, Sir Richard Branson met with me and a dozen entrepreneurs from our Chicago incubator, 1871, to talk about their businesses and answer their questions. Branson was his usual relaxed, thoughtful, and irreverent self, even in the midst of a media frenzy surrounding the opening of his first Virgin hotel (soon to be a chain with at least 20 others) in the Windy City.

Our conversation ran the gamut, including topics like packages (Package Zen), pot, pets (Wondermento), people, planes (OpenAirplane), and porn, with more than a few important tidbits of business advice and philosophy thrown in from a guy who's truly been there and done it all.

On people and delegating, his advice was simple: Find people smarter than you to run the day-to-day operations as soon as you can, so you can keep focused on the future. Responding to a question from the founder of HerbFront about investors' aversion to funding marijuana-related businesses, Branson (after noting that he had enjoyed many a spliff himself) spoke passionately about the need to decriminalize all drug abuse and to treat it as a health problem--instead of an excuse to lock up a bunch of kids who have the potential to turn into great entrepreneurs.

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When Branson was asked by the CEO of Georama what he thought about future travel becoming more video-based and virtual (folks traveling worldwide without leaving their homes), he reminded everyone that he did own an airline, so he wasn't really that enthused about the prospect, but then he went on to say that online video certainly worked well for sex, so who knew what might be coming down the pike.    

On the issue of social entrepreneurs, after hearing about SHIFT's business of providing cash advances to the very poor in underdeveloped countries, Branson challenged everyone in the room to use his or her entrepreneurial skills to make a real difference by taking on the world's problems. He added that entrepreneurs needed to look for new and novel approaches, because being just another "me-too" business in any industry was a certain path to failure.

When it comes to choosing the best opportunities (and running the risk of missing others), Branson told the co-founder of We Deliver that he himself accepted way too many challenges and that he was known around his businesses as "Dr. Yes." Branson added that you shouldn't fear missing the boat, because there were always more chances and new things coming along. It's most important, he said, to focus on being the best you could be at what you were doing. But smart operators should also keep one eye out for the folks trying to leapfrog you--and you need to be ready to leapfrog them right back.  

When the maker of the MagicTags iPhone app asked him about being included in a classic Apple commercial, Branson said that the best type of advertising is when it's for someone else and you don't have to pay for it. Then he recalled some of his early PR and promotional stunts with sunken planes and balloons over the years--even an ad that showed a sinking boat with a prominent Virgin logo and the line, "Next time, Richard, take the plane."   

After the owner of Crowdtap asked Branson about branding and the origin of the name Virgin, Branson said that it was harder today to come up with a good brand name, because so many names were taken. As for the Virgin name, he had narrowed the choices down to two: Virgin and Slipped Disk Records. Good thing he chose Virgin, Branson quipped, because Slipped Disk would have been an awful name for an airline.  

Shown the Bluetooth-enabled Gramovox music player offering a classic Sinatra tune, Sir Richard asked how he could get one to keep. After Branson was gifted the demo unit by its builder, on the spot, he jumped up (in his smashing red socks) and started dancing to Frank on top of a nearby ottoman.    

After wrapping up the session (and after shooting a bunch of selfies, lead by the developer of the Selfie app at 1871), Branson left the group with a most compelling comment. He said: "Between all of you, you can run the world."  

And then, lo and behold, Chicago Mayor Rahm Emanuel appeared.