- I was so pumped.
(woman laughs)
Look at this.
- [Woman] Ridiculous.
- [Man] Greg is being interviewed.
- Greg.
My alternate ego who loves television commercials
and is super passive.
(techno music)
- How do you get to the moment of clarity?
- I think by never relenting from the conversation
with myself about the reality of the situation.
Inevitably you'll get to the moment of clarity
if you spend every minute recognizing
this is a fucking problem and the quicker I address it
and understand it and respect it,
the quicker I'm gonna get to the solution.
Listen, this is why it's so scary.
This is why I don't like that everybody
wants to be an entrepreneur.
If you're listening to us right now
you're like, fuck, that sounds depressing,
what's fun about that?
It's the truth.
- [Rachel] I know I always tell people,
if you want to make money, this is not the route.
- To me, you can make money this way.
If you don't want to deal with
unbelievable amounts of pressure,
if you don't have the stomach for the pain...
It's like being an athlete.
If you wanna work out every day and eat healthy,
it seems so much more glamorous.
- I think one of the things
that I had learned in particular from you
is to be extremely self aware as a founder.
So when I started the business,
I essentially had a chat with myself
and had myself acknowledge
what are the things I'm the fucking best at?
And then what are the things that I should not be doing?
And step one was to surround myself with people
who could do all the things that I am not great at.
I'd say step three was having the foresight
to know what type of company I wanted to build,
and then find operators who'd done it.
I don't need to reinvent every aspect of the wheel.
There are things that Gary does every single day
that are tried and true to building a great company
that I can learn from.
So I would say that was a starting place
to identify who are the people
I should initially surround myself with.
- Just to jump back before I move on,
one thing I've been thinking a lot about
is building up self esteem and confidence.
How do you find the right balance
between instilling confidence
versus creating delusion and entitlement?
I think it's an extremely fine--
(audience laughs)
You like that one?
I've been spending a lot of time on this,
I'm just curious to get your perspective on it.
I think it's an extremely fine line and
I think that, for example,
just being selfish for a minute,
I think I've done too much of that
at Wine Library and VaynerMedia,
which has then created an undercurrent of entitlement
which takes a lot of time to then correct
and it's painful to start introducing
radical candor to massive optimism.
How do you think about it?
- Having humility and pride in your voice at the same time
I think is what creates authentic communication.
So with my team, no one gets penalized
for making small mistakes, because we're all human.
I would say the big thing is
if things were happening over time
and we gave someone the benefit
to show growth in their role,
then we would sit down and talk about,
okay, how do we put you on a performance review
that makes sense for the business
and help you achieve these certain milestones?
So I think the fact that I have such humility with my team,
like, Gary and I had a board meeting yesterday.
I left the board meeting, I go back to my office,
and of course my team wants to know
how the board meeting went.
I told them exactly how it went.
Because there's nothing to hide.
So I told them the good, the bad,
and having that level of humility, I think,
is the balance with having pride in your own voice.
- Have you studied, you're so early in your career,
you're on this path, but you are getting attention
and you're out and about.
Have you started mentoring yourself?
Have you thought about what that chapter looks like
or are you still very much focused on,
you're obviously still early in the business,
focusing on getting the value
out of that relationship of mentorship?
- [Rachel] No.
Similar to you, Gary, I'm so self critical.
I constantly, probably to a detriment,
every moment of the day,
I'm evaluating where the weakness is in my business
in myself, what's coming up on my calendar
that I feel like I need help with.
And I'll tell you,
I feel like one of the most underutilized words
in business right now is help.
And I've actually put that into practice.
- [Audience Member] So you talked a little bit
about correcting entitlement--
(audience laughs)
And I'm kind of wondering for both of you,
basically you could either rule with love or fear.
When you have team members who are kind of underperforming,
how do you know when it's time to do either of the two
or when to cut your losses?
- For me, fear is just never a good strategy
even when it's not working.
I'm flabbergasted by people's inability
to understand how much more positivity and optimism,
even if you thought about
how Rachel articulated when somebody was struggling,
how do we put you on a plan
that works for the business and works for you?
the thought that fear or negativity
is a good idea is ludicrous.
There's always a great way to do it.
I'll tell you, one of the things I'm trying to do
a better job of is I'm spending way more energy
on the way we exit somebody properly
than the way we onboard them properly
because I care so much about the final taste.
And when it's bad, I feel like
for all of us that are leaders here,
CEO, C Suite, what have you, you work for them.
And so you're in control and so for me,
I think there's a time for critical feedback.
To me, the cadence of positive reinforcement,
but you may want to look at this
and you think about your words carefully
and you wanna do it positive,
I do think there's a come to Jesus moment, I think,
after giving positive reinforcement,
but you may want to work on this.
There is a time of like, you probably suck.
And that's okay, maybe we suck, it takes two to tango,
but we need to figure this out 'cause nobody's winning here.
My point of view is if you're not able to be
the bigger person in every situation
when you have the leverage,
you're weak and you're creating vulnerability.
- You said you invested in Rachel and MikMak and LOLA.
So I'd love to hear what's different
about what you're looking for
and maybe what differences you see
in men versus women in fundraising.
- This is something that Rachel and Britt and...
I've done a lot of female...
What am I looking for?
I'm looking for good fucking businesses.
(audience laughs)
(audience applauds)
Obviously over the last half decade
as the conversation properly has been focusing
on the numbers that aren't matching up,
Rachel's always ragging on me for not talking enough about
how much female foundership I've done.
That is insane.
I don't know that stat.
I don't really pay attention to much, believe it or not.
That is unbelievably ridiculous.
So I wrote the first check into Birchbox, right?
And that was six or seven years ago
and I remember that meeting like it was yesterday.
We were in Starbucks in Midtown
and they were pitching
and they probably got about 60 words in
and I said I was in.
And I remember them getting super pumped and emotional.
Pretty emotional.
And I remember I just was like, awesome.
I was pumped, too, but I was like...
(audience laughs)
And they were just like, we've gotten so many nos.
We needed this yes.
And I was like, cool, I've seen that before,
I didn't think much of it.
And it was super interesting,
it's probably around this time of year,
it was that first really nice day in New York City
after the winter, you know that perfect,
I don't know if it was April or May but it was that day,
I think we all know what day that was.
And I was, ironically, less busy back then
so I could actually walk home,
and I live on the Upper East Side.
And in the 30 block walk,
I remembered somewhere around halfway being like,
wait a minute.
Is it possible...
The business was so obvious to me, it was like,
we're gonna get samples and sell them.
I was like, that's a great fucking business.
(audience laughs)
And at the time it was very social media
and it was a different world,
maybe 'cause I came from a retail background it clicked
but no question, it was a time
when it went through my mind of, holy shit,
are they getting nos because they're women?
And to be very frank, I'm a pretty transparent dude,
I intuitively, this is not, I'm not proud of this...
I wonder, and I don't know if it's true or not,
but I wonder if I even subconsciously
recognized that there was gonna be
great opportunities for me in female-founded businesses
if the market, back to this two percent bullshit,
was gonna view it--
Like, to me, I don't care if you're an alien.
Only Patriot fans are the things I usually don't invest in.
(audience laughs)
It's utterly embarrassing to me.
And not as a guy.
It's utterly embarrassing to me as a businessperson
in the game of merit wins
that those stats exist.
But I'll be very frank about this.
and I'm a big, big, big fan from afar
of how Cindy Gallop communicates this: fuck them.
I'm being dead serious, fuck VCs.
There's plenty of high net worth individuals out there,
there's plenty of other ways to get dollars,
or just make money from the beginning.
I'm so thrilled that the internet is here
because, no, I mean this, the mature internet
is unbelievably the middle layer.
It is the layer that we build on.
And that person isn't some 52 year old
Harvard Business School finance VC
that's making a subconscious biased or biased decision.
The internet is the middle, and we don't have to play.
And first of all, the whole VC ecosystem,
forget about men and women,
is not an exciting game to begin with.
Their model is predicated on pushing 20 businesses
way too hard and way too fast
with the hope that one breaks through
and pays for the whole nut.
It is so not founder-friendly in the scheme of things.
So to me, it's like, hearing that number,
where I really go in my head is like, good!
Hopefully that makes all of these badass women in here
think about alternative ways to raise money.
Because I don't think VCs in their current state
is all that exciting.
(audience applauds)
- I have to say,
I've never felt like Gary sees gender.
You treat business as an athlete--
- [Gary] 'Cause I want to fucking win.
(audience laughs)
It's insane to me.
- He's the best.
(audience laughs)
And there are other men out there in the world like Gary.
One of the reasons why I asked Gary to be here is
I'm a true believer that feminism
will only reach its pinnacle
if men are a part of the conversation.
(audience applause)
- 100%.
- [Rachel] Look for new ways to raise money.
I don't enjoy the VC ecosystem
and I have many strategic investors at MikMak.
- Question.
(piano music)