So, you know, I just quit my job at radio after being on air since I was 16 years old. I kinda risked everything for this new Dash Radio app. I hope you’ve checked it out. You’ve gotta tell me your favorite station. But what was the riskiest thing you’ve ever done in your career? […]
So, you know, I just quit my job at radio after being on air since
I was 16 years old. I kinda risked everything
for this new Dash Radio app. I hope you’ve checked it out. You’ve gotta 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 I’ve been at 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 enormous excitement I have behind doing this show
and thank you all for allowing me to do this show, is predicated on the fact
that I get to tell you things you’ve never heard before. I’m gonna say something
that I’ve never ever ever ever ever 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
with 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 to me. You’ll like this answer. The toughest thing I ever had to do, believe it or not, was make the decision that I was okay with putting myself out there. You know, a lot of you
probably have at this point forgotten because the Gary Vee persona and narrative has taken over
my career and my Wikipedia and things of that nature. But the first 10 to 15
articles that have ever been written about me in the
AP and the New York Times and the Wall Street Journal was, “Wiz Kid Builds Business.” That the establishment,
the business world, the people that I look up to in ways, maybe not specifically because I don’t really have heroes, but respect their opinions
and their accomplishments. I went from the narrative of being a great business operator that
saw trends and executed it for 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. 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 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’s very honestly I still continue to deal with. I, now, this is where you
start getting into the, I don’t know, DRock, if you
wanna make it dark. But this is where you start
getting into the darkest stuff. In a weird way, 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 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 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 wanna 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 gonna be greater. That mis-positioning was something that, that was tough.