Sir Richard Branson met with a dozen entrepreneurs from Chicago’s 1871

Sir Richard Branson met with a dozen entrepreneurs from Chicago’s 1871, a huge start-up incubator with more than 325 companies (which are operating on a single floor in a 75,000 square foot space), to hear brief descriptions of their businesses and answer their questions. Branson was his usual relaxed, thoughtful and irreverent self even in the midst of the media frenzy surrounding the opening of his first Virgin hotel (soon to be a chain of at least 20 others) in the Windy City.

Lead by 1871 CEO Howard Tullman who first summarized the Chicago and Illinois startup scene and 1871’s own growth and remarkable results to date, the far-ranging conversation ran the gamut from packages (Package Zen), pot and pets (Wondermento) –to people, planes (OpenAirplane) and porn – and all the way from slipped disks to outer space - 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 on investors’ aversion to investing in pot-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 were as likely as not to turn into great entrepreneurs.

Asked by the CEO of Georama what he thought about future travel becoming more video-based and virtual with folks traveling world-wide 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 cash advances to the very poor in underdeveloped countries, he challenged everyone to use their entrepreneurial skills to make a real difference by taking on the world’s problems. He added that they needed to look for new and novel approaches because just being another “me-too” business in any industry was a certain path to failure. 

As to choosing the best opportunities (and running the risk of missing others), he 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”, and he added that you shouldn’t fear missing the boat because there were always more chances and new things coming along and that it was most important 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, Sir Richard 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 promotion stunts with sunk planes and balloons over the years and even an ad that showed a sinking boat with a prominent Virgin logo and the line – “next time, Richard, take the plane”.

And asked about strong branding by the owner of Crowdtap and the origin of the name Virgin, Branson said that it was hard today to come up with a good brand name because so many names were taken. As to the Virgin name, he had narrowed the choices down to two – Virgin and Slipped Disk records – and he happily choose Virgin 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 right there in the Shag Room. He was promptly gifted the demo unit by its builder on the spot and he jumped up (in his smashing red socks) and started dancing to Frank on top of the nearby ottoman. 

Wrapping up the give-and-take session, and after shooting a bunch of selfies lead by the developer of the SELFIE app at 1871, he 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.