In his final Founder Stories interview with host Chris Dixon, Mayor Bloomberg begins by offering advice to those wrestling with a career decision – becoming an entrepreneur or joining a bigger company.
Having tasted both worlds, Mayor Bloomberg points out “big companies have more structure but you have a little more security. Small companies, a lot less structure but a lot higher payoff.” While he thinks transitioning from a bigger company to a smaller company is easier than the opposite, he notes “if you have a vision and want [to strike out on your own], do it.” He honestly admits however, “I don’t know whether I would have had the courage to go do it if I hadn’t gotten fired.”
Speaking from first hand experience, the Mayor tosses another option into the mix – public service. Similar to the private sector, he believes “it’s hard work, it’s being willing to stand up for what you believe” but recognizes “the payoff isn’t in dollars, it’s in satisfaction.”
It seems appropriate that success he’s had in these three sectors occurred in “The City That Never Sleeps.
“I am not smarter than anybody else but I can out work you – and my key to success for you, or anybody else is make sure you are the first one in there every day and the last one to leave. Don’t ever take a lunch break or go to the bathroom, you keep working. You don’t ever know when that opportunity is going to come along.” He continues, “every opportunity I ever had, it was I think an awful lot of them was because I was there at the time. And that is the one thing you can control. You can’t control your luck, but the harder you work, the luckier you get.”
Also important, “that drive to look at the bight side.” Adding, “there’s never been a day that I haven’t looked forward to going into work, even the days I knew I was going to get beaten-up, even the day I knew I was going to get fired – I’d never been fired before, I wonder what it is like, ok, let’s go find out.”
Mayor Bloomberg shares many more personal insights during the interview. Make sure see them all by watching the entire video.
Episode I is here. Episode II is here.
Past Founder Stories episodes featuring leaders of Bump, Dropbox, MeetUp, Instagram and many other startups are here.