Entrepreneurship is Not as Glamorous as it Looks| DailyVee 452

oh so pumped correct my alternate ego who loves television commercials that is super passive I think by never relenting from the conversation with myself about the reality of the situation inevitable you'll get to the moment of clarity if you spend every minute recognizing this is a [ __ ] problem and you know the quicker I dress 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 like if you're listening to us right now you're like [ __ ] that sounds depressing like what's fun about that it's the truth if you want you know it's just 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 and that's what you know I know it's like being an athlete like if you want to work out every day and eat healthy and like watch mail like it seems so much more glamorous you know I think one of the things 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 [ __ ] best at and then one of 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 to build and then find operators who've done it I think 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 as I say that was the starting place to identify who are the people I should initially surround myself with just 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 you like that one I think it's you know 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 you know I think that for example just being selfish for a minute I think I've done too much of that at Wine Library in vaynermedia which is 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 how do you think about having humility and pride in your voice at the same time I think is what the creates play authentic communication so with my team like knowing 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 you know then we would sit down and talked 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 you want 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 know 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 are you still very much focused on you're obviously early in the business focusing on getting the value out of that relationship of mentorship no I similar to you Gary like I'm so self-critical so I constantly probably to the detriment every evaluating like where the weaknesses in my business and myself what's coming up in 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 like put that into practice so it's a little bit about correcting a beer when you have team members who were kind of underperforming how do you know either I mean for me fear is just never

a good strategy even when it's not working you know I I'm flabbergasted by people's inability to understand how much more positive in optimal 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 you know there's always a great way to do it I mean 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 that we onboard them properly because I care so much about the final taste and when it when it's bad I feel like you know to me for all of us that are leaders here CEO c-suite what have you work for them and so you're in control and so for me you know I think there's a time for critical feedback you know to me the cadence of positive reinforcement but you may want to look at this and you think about your words carefully and you want to do it positive I do think there's a come-to-jesus moment I think you know after giving positive reinforcement but you may want to work on this there is a time of like you probably suck you know and that's okay like maybe we suck you know takes two to tango but we need to figure this out because 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 and Lola would love to hear what's different about what you're looking for and maybe what differences I see in men versus women so this is something that Rachel and Britt and the birches I like I've done a lot of female you know what am I looking for I'm looking for good [ __ ] businesses and so like obviously over the last half decade as the conversation properly has been focusing on the numbers that are matching up you know one thing you know Rachel's like always ragging on me for not talking enough about how much female founder ship I've done you know that is insane like I don't know that's that like I just like I don't really pay attention to much believe it or not like that is unbelievably ridiculous and so you know I remember so I wrote the first check into Birchbox right and so 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 remembered them getting super pumped and emotional and not you know like pretty emotional and I remember um just was like what's like who awesome like I was palm too but I was like you know like and they were just like we've gotten so many knows you know like we needed this yes and I was like cool like I've seen that before like I would 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 like the winter you know like that perfect like I don't know if it was April or May but it was that day I think we all know what they that was and I was ironically less busy back then so I could actually walk home and I live in the Upper East Side in that 30 block walk I remember somewhere around halfway being like wait a minute like is it possible like 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 [ __ ] business and maybe I'm and at the time it was very social media and it was a different world maybe because I came from a retail background it clicked but no question it was a time when I went through my mind of like holy [ __ ] are they getting knows because they're women and to be very frank I want to be 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 going to be great opportunities for me in female found businesses if the market back to this 2% [ __ ] was gonna view it I like to me I don't care if you're an alien you know like the only like only Patriot fans are the things that I usually don't invest in but like it's utterly embarrassing to me and not as a guy it's utterly embarrassing me to me as a business person in the game of merit wins that those stats exist but I'll be very frank about this and I'm a big big fan from afar of how Cindy Gallup communicates this [ __ ] them like I'm being dead serious like 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 like 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 you know Harvard Business School Finance VC that's making a subconscious bias for bias decision the Internet is the middle and we don't have to play and like 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 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 you know to me it's like hearing that number like where I really go in my head is like good hopefully that makes all these badass women in here think about alternative ways to raise money because I don't think he sees in their current state is all that exciting I never felt like Gary C's gender like you treat business because I want to [ __ ] win it's insane to me it's I'm and there are other men out in the world like Gary like one of the reasons why I asked you here is I'm a true believer that feminism will only reach its pinnacle if men are a part of the conversation and yeah it's just looking for new ways to raise money like I don't enjoy the VC ecosystem and I have many strategic investors at McMahon question you