The Sage Summit for 2016 was held in Chicago and featured keynote interviews with an impressive number of technology celebpreneurs including Sir Richard Branson, television Sharks Daymond John and Robert Herjavec, the actors Ashton Kutcher and Gwyneth Paltrow, plus Yancey Strickler, the CEO of Kickstarter.

Frankly, you never know how these things are going to turn out although I was pleasantly surprised that both the business observations and the jokes were much better than expected. I mean when Gwyneth starts talking about KPIs and multi-year business plans, it's a moment. And she had a great quote from a friend about intentionality, aiming high and not letting the naysayers get you down. Her friend said: "Where you look is where you go." And truer words were never spoken.

Sir Richard told a great story about buying his first plane for Virgin Airlines from Boeing. The salesman was willing to make the sale, but he suggested changing the name of the airline from Virgin because he said that otherwise the passengers would think that the airline wasn't willing to go all the way. He is always worth listening to and a class act as well.

And when Strickler said that Kickstarter had helped create more than 8,800 new businesses and non-profits since it began in 2009, it was a fairly amazing statistic. But when he added that Kickstarter users have pledged upwards of $2.5 billion for more than 110,000 projects, it was astounding. I was also amazed to hear that he has NO social media apps on his phone, although he fessed up to recently adding Twitter so he could follow the goings-on at the Democratic  convention.

Strickler said that he fears that the interruptive nature of our mobile devices is very bad for our sanity. "Social media is doing to our brains what smoking used to do to our lungs--it's mental sugar--and it's addictive," he said. Ashton turns off all the notifications on his phone and said  that it is always on "do not disturb" (except for calls from his wife) because that's the only way he can get anything done. He said that otherwise you're working for all the people who call and want you to do things on their schedule instead of setting and controlling your own agenda. On social media, Ashton also said that it was stupid and a waste of resources to chase every new social app or trend. Notwithstanding the Kardashians, he noted that celebrities go where the fans are while fans don't necessarily go where the celebrities are or want them to go. Trying to pile on to this week's latest bandwagon or hottest download is a great way to go bust.

When Ashton focused on what it takes to scale your business from a people perspective, he talked about a very important consideration that's a real challenge for companies as they grow, especially given the "can do" attitude of the startup world. He noted that, when you begin, everyone pitches in and does whatever it takes, but as you grow, this approach no longer works because no one has all the skills to be really good at everything. So it becomes critical for "people to stay in their lanes" and focus deeply on what they can do really well. New and different people will need to be recruited to the team to cover more specialized skill sets as you expand the business. I called this "sticking to your knitting" in a piece I wrote a while ago.

Daymond John said his mother was quite the negotiator. She borrowed $100,000 to help him in his business by mortgaging her home, which couldn't have been worth $75,000 max. He wasn't really sure how she came up with the cash, but he was sure glad that she did.  Daymond made some very interesting observations about the need to know what your strengths, weaknesses and interests are and to change and adapt your businesses accordingly. He discovered that he doesn't want to have hundreds or thousands of employees ever because that kind of scale makes it impossible to have any kind of real personal connections to the people working with and for you.  And he said that a critical skill for success was the willingness to ask for help and to admit to what you don't know.

Since a number of these folks are active investors themselves, they were all asked about what they look for in a deal and--as you would expect--it was much more about the entrepreneur than the idea. As Daymond noted, they all looked for people with the humility to ask for help and a willingness to learn from anyone and everyone they encountered. Ashton pointed out that the winners had a sense of generosity about them and a willingness to share and to help others that was contagious and readily apparent. He said that it was critical that successful entrepreneurs learn to manage and contain their emotions.

Making a difference and giving back was a part of everyone's comments although Ashton said that he thought that people who spent time worrying and talking about their "legacies" were assholes. When he was asked what he'd like people to say about him in 50 years, his answer: "Is he still alive and building shit?" totally brought down the house and was clearly the best line of the day.

To view the original article, visit