What Was the Riskiest Choice You've Ever Made In Your Career?

what's up gary so um you know i just quit my job at radio after being on air since i was 16 years old i kind of risked everything for this new dash radio app i hope you've checked it out you got to tell me your favorite station but what was the riskiest thing you've ever done in your career because it was tough for me to leave something up in it for so long especially an institution like traditional radio in order to try something new with zero listeners today to disrupt that industry what was the toughest choice you ever made in your life or in business about leaving something that you've done to do something new you know again the uh the enormous uh excitement i have behind doing this show and thank you all for allowing me to do this show uh is predicated on the fact that i get to tell you things you've never heard before i'm going to say something that i've never ever have talked about before which is the toughest professional thing i've ever done my cliche answer historically has been you know leaving the wine library which is my first love and that's a very big truth but as i've started becoming a little bit more in tune with my own feelings and have given this thought the toughest thing i ever had to do and steve pay attention like this answer toughest thing i ever had to do believe it or not was make the decision that i was okay with putting myself out there it you know a lot of you probably have at this point forgotten because the garyvee persona and narrative has taken over my career in my wikipedia and things of that nature but the first 10 to 15 articles that have ever been written about me in the ap in the new york times in the wall street journal was wizkid bill's business that the establishment the business world the people that i look up to in ways maybe not specifically because they don't really have heroes but like respect their uh their opinions and um and their accomplishments i went from the narrative of being a great business operator that saw trends and executed it for the financial gain which is like something everybody deems to be so noble in business to being a self-promoter to being a social media guru to being an author um making the decision that i could accept the rolling of the eyes of the ivy league grads or the establishment to get bigger reach to build audience to jam with people to be human and extroverted and taking that step back or two or three in the minds of the top two or three percent um was a pretty interesting difficult decision for me knowing what the consequences were of putting myself out there and that i would be respected less for my business accomplishments because of it wasn't the easiest thing that i ever had to deal with and something that very honestly i still continue to deal with i now this is where you start getting into i don't know drock you want to make it dark but this is when you start getting into the darkness of it in a weird way it's i like the underestimation that comes along with it as well because the truth is the reason that entrepreneurship and business speaks to me especially in an american context um is that the truth is undefeated that ultimately you know if i go and execute multiple hundred million dollar businesses and make smart investments it's all net right like you may not like the fact that i don't dress up or that i curse on stage or that i self-promote or whatever you want to call it but if i execute you just have to eat it and so that was clearly dj that was clearly the toughest thing for me which was that i was consciously self-aware that i was entering a realm where i would start becoming more disrespected even though my accomplishments were going to be greater that mispositioning was something that uh that was tough