Entrepreneurship is Not as Glamorous as it Looks| DailyVee 452
Really enjoyed getting to have this fireside chat because I think that it's a super important conversation that needs to be had regarding the current state of ...
- 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.
- 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.
- 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?
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.
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.
- 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’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 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.
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.
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 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.
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.
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.