I thought I'd be there forever until the day I did it.
You know, it's funny.
I never had a conversation with my dad
about me leaving day-to-day.
It just kind of happened.
It was like crazy to think about.
Was also a time where,
probably the toughest time my career
was with my dad and I weren't clicking.
There was a point where the business got so big
and I was getting the credit
and I was starting to get the credit in the press
and I feel like I could have done a better job
of giving my dad more credit
but I think at some level
(sighs) I was struggling subconsciously
without even realizing it that I owned nothing of it.
And now I'm married
and you know, here I am at 30, 31, 32 years old,
I'm not paying myself a lot of money at all.
You kinda wake up and you've put,
you know, a decade of 15-hour days,
360 days a year into something,
you've built something and watched it grow
from 4 to 60 million in revenue.
And you've never you've never really made
more than $150 000 a year.
I just started getting so much of the credit,
that it started undermining
my dad's own feelings for himself.
It's almost like he was getting wiped out of history
and it was an interesting difficult time.
What it took for me to get outta that moment was
the ability to start over.
(dramatic music)
- [Director] Did you feel like there was a point where
you felt maybe unfulfilled by what,
even though you were fulfilled,
helping your dad doing all this,
you were unfulfilled.
There was something else that was there for you,
that you wanted to chase,
you wanted to pursue it?
- Yeah, I mean I could feel like, me changing.
You know, the obsession with building
the biggest wine retail company in America was fading.
And my curiosity about this Web 2.0
evolution of the Internet was rising.
And I was starting to realize
it wasn't that I was a great wine merchant,
it was that I was a great communicator.
And, my career started to shift.
(dramatic music)
At some levels, you don't realize
when something is dying down when you're in it.
And I didn't realize how much
fire something new and fresh
and wide open and so grand, you know,
I'm coming from the wine business, which is incredible
and I missed it so much I got back into it,
but this whole world of like,
this is the changing media landscape,
this is the communication change,
this is going to affect the world.
I often use the analogy of a lightning bug
that just goes to the light and gets zapped.
I always wondered,
does that bug know that they're about to get zapped
but they just can't help it?
There's an enormous sense of destiny
that runs through my body.
You know, I just
I just feel it.
The most important thing I'd think about
when I think about getting to happiness
is not so much owning anything.
It's the ability to not hear anything but yourself.
There's nothing more powerful than
when everything gets quiet
and the only thing that penetrates
is your own voice and that voice isn't judging you.
- [Director] When you look back now,
at the kid who felt pressure
or the kid who felt an obligation.
what would you say that kid now?
- I would tell that kid
to stay the course 'cause he's gotta figure it out.