WeWork Stories Pt 1

and thank you very much for Gary for uh doing this for us I'm super excited I've posted a few other uh we work stories events and I know this one is going to be the best yet so I'm totally St ever not yet but will never be one better than this that's it we're done that's uh so cool I want to actually start I'm going to ask a few questions I want to get a little bit more information about Gary I actually haven't spent that much time um chatting with him before so I'm going to start when he was pretty young and we'll work our way up and then we'll open up for Q& A um there was Gary I'm really curious you had a quote I think somewhere online about how when you were 8 years old you were out there actually selling 11 a as other kids are just still learning how to squeeze it um I'm really curious about sort of you know with your background uh and coming over here um to the United States as a child how what really drove that sort of passion for you uh to really create something when you were eight should have been running through spring I think yeah I mean I ran through sprinklers as well like slip and slide and plenty of other things as well but um you know it's crazy I me it goes back to being five or six years old and trying to sell stuff you know at some level you know DNA is one powerful thing and um it's just something that has always been there I've never filtered the world without thinking about business it's just been in my brain you know I've always thought about how can I sell this or how can I do that it's just it's there and so to me it didn't seem weird to me like when it started snowing I did not think about building a snowman I was like looked you know oh I should make a quick note my sister is literally in labor right this second so I just want you to all know how much I'm committed to commitments cuz family is my thing and I'm getting the hell out of usually as I told you on the phone I was going to stay a little longer and shake some hands and kiss some babies but I'm out I got to go to Jersey and uh see my new niece hopefully will be arriving any minute um but speaking of thank you speaking of that my sister like it started snowing and I would just look at my sister's face you I was eight she was four and I was like get your [ __ ] shovel we're going to work you know and so like you know that's like I was pumped when it would snow because I knew that I was going to shovel driveways and make cash and you know a lot of people around me know that I don't I'm not obsessed about scale I like putting in the work I like the dirt under my fingernails I'm proud of it I think it matters more than I think we think I think we're living through a culture of a lot of smart people right now especially in our space here that are very predicated on the math and the analytics and the efficiencies I take enormous pride in caring about that stuff but I think you need to put in the work and putting in the work has been something that's always just come very natural to me I mean we've seen it through I mean your life right after college you decided to really take get your hands dirty with your parents' business and back in I think it was 2006 you started the Thunder show which was amazing uh for those of you who don't know Gary started saying Wine Library TV where he would rate these wines and he had this unique way of getting even the uh least common denominator of wine connoisseurs myself included to sort of understand somebody is here from Istanbul that was what that was such an awesome conference it was it really was thanks for being here yeah thanks for coming yeah sorry I'm [ __ ] to totally F I'm here to stay on my toes by the way get very used to it um so when you did that this was a great show we all loved it but you at one point I think he back in 09 maybe or maybe a little bit later than that you decided to stop and stopping almost anything is really tough you know that momentum how do you come to that as an entrepreneur well I mean it was 2011 I did a thousand episodes of Wine Library TV and a month before I decided 3 or four months earlier that 5 years of five days a week putting out a 25 minute show was a good run right it you know it's not and I decided that I was going to retire and at the last minute maybe 3 months you know two months right before I was going to retire I bed I started feeling like I was going to let people down I didn't want to let my you know I started reading every comment it started for 3 years com ments 20 40 comments per episode saying don't ever stop people knew that it was like you know that I was grinding and all of a sudden when I knew I was going to stop every time I saw that in the comment section it hurt and it like started building and so I kind of panicked and I decided to start something called daily grape for the people that here that most follow me remember and I decided okay if I'm going to stop let me do something new shorter form because I was into this whole micro content thing that bner media has evolved into um mobile so it's mobile driven subscription to BU so I tried to

make it work for me it just the decision was done at that point so I did do 89 episodes of that as well um you know I decided it was time you know I just woke up one morning in early 2011 I was like that's it you know I I did it uh I'm at this point now where I Feel Complete about this part of my career and journey and there's other things that were starting to pull in my heartstrings and other things that I was thinking about and you know I've always knew that it was going to be a chapter I think for a lot of people you can go read blog posts in 20098 when I started talking about business and not just wine people in America and really the world love to keep you in your lane you know there was a lot of people that said to me why are you talking about business Wine Guy stick to penio [ __ ] you know things like that and it was funny to me to think about it because to me I was always a businessman before I was the wine guy I built a very large e-commerce and retail business long before I ever started that first episode of Wine Library TV so it was fascinating to me that I was happy that I made that decision because I was getting ridiculous offers to do a television show The Bravos and the food networks of the world and they were very attractive they would have allowed me to become really famous I would have made it but I always bed at the 11th Hour on these deals mainly because I knew that I would become America's wine guy if I made that play and I just knew there was other things I wanted to talk about and I didn't want pigeon hole myself and Heck if a fairly successful internet video show made people feel like they wanted to keep me in that lane what would have a hit TV show done right and so it's kind of what we do right like it happens to actors like Tony Soprano can't do [ __ ] because we just can't get him out of our mind as Tony Soprano and I just I I'm an entrepreneur first right and I just needed to be able to talk about those things needed to be involved in those things and it just felt like the time was right oh I mean that makes total sense and I personally very much Miss Wine Library TV mostly because back uh when we were just starting Indie Hall in the 215 you actually came down and brought all the wine and I made a couple really great friends there and had a very uh late drunk evening um but I appreciate that and I'm glad that you're doing other things now as well but one thing is and it was 2009 you started vayer media correct and so you did that with somebody who you've known for 26 years now of your life yes uh and Family Matters to your lot it's your and I'm I am more curious about how that relationship works now that you're working together every day than how you sort of got to there like how has that changed the way that you two interact before I answer that tremendous question just want to say that I love frank Esposito I'm reading it baby but I'm not reading the board anymore I'm not going to ruin the interview anymore by reading the board that was the last guy is a VOR media employee uh it's interesting listen family business how many people here by show of hands uh work in a family business so you know for the five or six of you know there's Dynamics in a family business that are very different uh than any other business that you could be in with different partners you know AJ is 11 years younger than me I would tell you that you know in some weird way AJ is my first love right because I was you know he's just my man and I was like you know 17 when he was six and my dad is very different than I am and very much a different character and he's the best but he's not kind of the guy you go to talk about anything right it's just you know just a truth he's old schooled he's not he does amazing things in many places but emotionally he's not you know bringing that to the table and AJ and I because of our age difference have almost a brother father kind of thing going on that's very kind of unique and special and we've been we've met so many people that are 11 or 12 or 9 or 10 years apart and don't have what we have you know it's tough I mean I was out of the house when he was seven right and so it's just a very unique thing we have a very very special bond I've been very successful in family businesses because at the end of the day I love my family more than I love money I there's just really nothing else and I [ __ ] mean it like a lot it's easy to say it people say it um but we also have to know the players I've been lucky that both my dad and my brother don't mind me being the face or you know I want the Limelight I want the engagement I want the interaction it's the kind of creature I am both of them are a little bit more introverted differently wired so I spend a lot of time understanding what makes them tick and what they care about so I bring that to the table and then you know and it's been nice that they've been able to allow me to do what I need to do um it's changed in the fact that you know AJ and I are running a big

company Vayner media has gone from 25 to 250 employees in the last 18 months since I've gotten fully involved and so you we're running a big company and we're moving very fast and there's a lot of Vayner employees in here and they know that like we're running a very fast entrepreneurial ship and we have our ups and downs and lefts and rights and the unfortunate thing that a lot of you know is you have to take time to step out of your business mind because the AJ and I only talk about [ __ ] bad stuff bad stuff that's what happens when you're a leader running the show you're talking about the problems because you're trying to address them and we actively try to figure out ways to celebrate the wins but it's not in our DNA we're climbers so we're worried about the Rocks ahead of us the Rocks we're dealing with right now we tend to never celebrate enough and so what's changed is where all our conversations used to be predicated of lightweight you know we stress about the Jets but you know for the most part it was pretty lightweight stuff now we're talking about very intense stuff very like we're very ingrained into it and it's been a an interesting Journey with him um because I'm mentoring him before I was kind of the son of a father and so I'm in a different place um I think it's working extremely well the thing that AJ and I have that I don't think my dad and I even had is I wouldn't call it respect but I got it I came into my family business as a 21-year-old kid and exploded it I walked in and in 4 years took a business from 3 to 25 million so I don't disrespect 21 22 23 24 year olds I understand what you don't have but I sure know since I just did it five minutes ago I know what you might have as well and so I respect AJ in a way that none of my contemporaries thought I would not in a way that a lot of my contemporaries thought I should and uh and I think it's helped us that AJ knows how to cuddle my ego and my wants and my insanity and you know I'm willing to do whatever but when I make a decision that I want to do something if I walked into the office right now and AJ could taste that I was dead serious and I said I wanted to Pivot to sell chickens on 7th Avenue he'd be like [ __ ] it let's go and I need that and he gives me that and I just think we're tremendous Partners I'll definitely buy them um you know you it's clear that you are passionate and you care about uh a lot of things your family included um and you family first and uh and you said in the past that caring about others is both a gift and a curse for you and I'm really curious about how has it been a curse like what have been the things that have really worked against you or have been negative because of it the number one asset in the world is time and I've given time to so many things that on paper are difficult to understand why and in retrospect that's why you know like I you know I really you know it's my listen I know my success is predicated on it so I can never hate on it and I don't talk about I mean a lot of people here know who I am I don't talk a lot about negatives everybody's got problems I'm uncomfortable sharing mine um but it's you know as you start getting more known you know what am I going to talk about crushing it every 40 seconds so you try to evolve you know your conversation and you know after talking you know I'm a minority I'm an edge case so after talking about things that I think other people aren't seeing and have built up to be fortunate enough in a place where this many people want to come and see me speak um then I started saying you know what maybe I should start talking to one or 2% or 3% that actually do look like me that you know and that's been where some of those things have come out and I actually appreciate you're doing your homework that's a very good question you know listen I have a very tough time saying no not trying to overd deliver even if it's for a perfect stranger let alone an entrylevel employeeemployee on his first day or somebody that's in my world you know I have I over index on the things that like empathy are why I'm successful but they're also very difficult to manage and it's exhausting like you know I'm just I'm consuming and I'm taking on pressure from every direction from my two businesses from my personal brand from the people that are cynical and have hate out there for it for the concerns I have for everybody in my organization let it not be confused and there's plenty of vainer people in here and they know it's true I'm the head of HR you know we have great HR people but I'm like I'm micromanaging everybody's emotions to the best of my ability I forgot that I've gotten older and I've had a little success in my career so I think some of the entry level employees don't believe it and

they're scared to engage with me but once they do they're surprised and so you know I consume emotion at scale and uh and that's can be daunting at times I mean you've clearly worked on many things and one that sort of we've seen over the last few years is you you've become quite the active investor in a number of very interesting companies including tumbller who was recently acquired uh and also Grand Street one of my personal favorites right now uh got some great products but I'm really curious about where do you see the next kind of for you and Investments if it's in Tech or not over the next like 3 to 5 years maybe even 5 to 10 where do you see sort of your focus in that changing what what's exciting you the most I'm starting to really consider some sort of funded vehicle you know I don't want to be the cliche guy and start a fund but man it's some you know listen I'm going to be very honest with all of you guys like I always am I suck at so much it's not even funny but boy do I have intuition and when you have intuition when it comes to business it can be very profitable and very successful and you know when I look at the exits that I've achieved with you know early Facebook at you know buying Facebook stock from zuck's parents buying the Twitter's first CTO when he was exiting his stock in' 08 buying Tumblr and 09 you know buddy media wildfire and you know I mean when I think about that I don't have a lot of liquid to invest it always been my personal money and when I think about my God if I had a vehicle behind this and I had 2030 whatever perc behind this you know I feel very confident in my ability to decode an entrepreneur and a business model very quickly and so two things run through my mind one should I ever consider getting a little deeper in that space um you know I've you know a lot of people know me for what I am out here and I and then there's people that know me a little deeper a lot of the people that I've been lucky enough to invest or invise in one thing that I don't think a lot of people know is I'm a very deep product kind of guy right growing up in retail I my retail store was my product I thought about endcaps and what to put at the register so conversion and color schemes and copy so it was interesting for carp wanted me in Tumblr because he wanted me for my product thoughts I mean that's nuts like nobody would believe that here and so I have a very good reputation with some of the best companies in the world for that product stuff which they want the promotion and the marketing and some of the biz de but I'm able to get into deals that maybe it wouldn't look like it would be able to get into and so I may want to take advantage of that as far as what to invest in you know I'm a big believer and you bet on the jockey I'm very big on who the entrepreneur is if you know some entrepreneurs will pivot seven times and win if they've got that stomach I mean there's a couple of gals recently that I've invested in um it's really interesting lately I've been investing in more female driven business Grand Street um couple of other things um that I just know that they're not going to allow like there's just no shot of losing right and there's entrepreneurs like got out there that they don't back to me selling chickens I would only do that if I thought that was the best use of my time and the money and the opportunity and so um yeah I like to bet on jockey so I don't really it's not like oh I want mobile or I want e-commerce you know I want people that I think can kill it and if they can explain it to me what they're doing and I understand that there's a market need or opportunity I'll bet