Ilana Golan x GaryVee: Building a $300M Business the Hard Way

0:00I see a lot of people making great plans, being pretty intentional. where I see so much breaking down is people do not have the grit to execute against their ambitions. Stop being full of shit is what I'm basically saying. Like I'm really trying to get there. Like don't say that this is your, you know like this lady, she's like, this is mama's money making thing. And she's like a friend of mine. And like three weeks later I checked, I like could see like, I was like, what happened to mama? She's like, oh it's hard. I'm like, no shit it's hard. Like what do you, Like, I just think that people are wildly entitled.

0:38Like, if we're going to be really focused on it. Like, when I hear your energy, I'm like, be thoughtful. Like, right? You must know that you are signing up for hard. Oh, yeah. Like, I don't understand how people understand. It's hard. Like, this concept of easy. And it's beautiful. It's hard and it's beautiful. It's beyond beautiful. Nothing feels better than when you accomplish something that was hard for you. There's nothing that feels better than when you prove something to yourself. Nothing. It's like everyone's ultimate, whatever that is, run a marathon, change a diaper.

1:21I'm very glad I don't need to change those anymore, let me tell you. But I mean, I really think that, I think we need to start talking more about tenacity and perseverance and grit. It is really a lost conversation. It's the most important one, though. It's really important. Like, people are unhappy because of that being eliminated from the equation. I'm telling you, that's what's happening. I want to take you back to probably somewhere around, I don't know, 2009. Yeah. And create a little bit of a blueprint. like a map for people. Because at that point, you already built the wine business. You already understood the internet is a big thing.

2:04You already built this thing, Wine Library, right? So a big, you know, to what it is. And I think it went from what? 30 million to 60 million? Or 3 million to 60 million, right? So, but now you have this decision. You're seeing something that maybe more companies will need this. Yes. But a lot of people see things, but they don't jump. Can you take me to what made that decision? Take me to that time in your life. You know, I think adversity is the foundation of success. And I had accomplished my first goal in life, which was to build a big business for my family. What I had not anticipated is, if I'm being transparent, the bind I found myself in, which was I had just spent the ages of 18 and really 22 to 34 spending 70, 80, 90, 100, 110 hours a week, every week for a decade to build a very large business for my father who was a young man.

3:12I was 34. He was 56. And I didn't have any money. and I was starting to resent my father and I had just gotten married and I needed to start a family. And I was challenged and I had a brother who was 11 years younger to me that was graduating college who looked to me as someone who he wanted to do something with. So I had a lot of life events going on and I had skills and I had vision. I did see that social media was going to eat up the world and become a major part of society let alone marketing that I did but I had no money and so what I saw was an opportunity to build this agency and what had happened was I was just willing to be scrappy and I was willing to be scrappy at 34 which is why I struggle with so many people not willing to be scrappy at 22.

4:21Yeah. And what I mean by scrappy was my life was not fucking fancy. Like I don't know what else to say. Like I paid my rent. I didn't take lavish vacations. I didn't have stuff. And I literally hustled my way into opportunities like the following. Ironically, just a couple hours ago, I did a podcast for my friends Cass and Mike Lazaro. Ah, we're gonna see them in two hours. Amazing. Yeah, yeah, yeah. So they were just here. Shoveling shit. is their new book and that's what we were talking about. I started VaynerMedia in the conference room of their company Buddy Media in 2009. I know. So I couldn't afford rent for my company nor could I afford paying anyone.

5:01So our first three employees were interns all friends of my brother but because it was spring of 2009 the economy had just collapsed in 2008 so all his friends that had jobs lined up lost them. So they were also scrapping. And then I had a customer from Wine Library who I'd known for a long time who was in marketing. He had his own kind of like sampling company and they had a project and he was he needed some he was like the social media thing can I use that? I was like yeah. So they paid us a couple bucks to help and in those couple bucks I'm talking$30 ,000 I used that money to kind of get us going and I'm talking get us going like the the money we paid for gas to go down to Campbell's for a meeting or and what I did have though was I had a little bit of reputation I was known a little bit because the Twitter thing was coming and I started making content about marketing and that content led to opportunities now for everyone who's listening the way that social media works now is if you have no reputation and you have no followers you can make one smart video right now about how AI tools work for marketing and that video can and lead to your customers.

6:14That's what happened to me. And so that's who we were. We were a company that knew something was about to happen and was using that medium to actually attract opportunity. So take me there. So you're basically asking Mike and Cass for their office, which is very bold and very, very scary. And very honestly, because I want to tell the story in truth, Mike and I met because an employee of his was fascinated by my content. And we hit it off in our meeting. He offered. Wow. Because he's such a mensch. But, you know. And that's pretty incredible because they're not in a big spot by then. They have a small office.

7:01And at that point, they're giving you their mayor. It was half the size of this for context. Okay, so that's your office when you get started. Now you decide, if I'm not mistaken, not to raise capital. Correct. Right? So take me there because at that point, and we're in Leap Academy, decided not to raise capital. But at that point, it becomes, there's some money fears, right? Like whatever you bring in, that is the salary. So take me to those moments. Like, did you have moments of, oh my God, I don't have salary this month. Or like, take me there a little bit to the beginning. I believe that most companies and most people are unhappy and lose because they don't think in terms of saving money.

7:48Tell me more. I will. The reason we worked was every time we got money, including that first$30 ,000, we spent only$15 ,000 of it. Like I wasn't hiring ahead of our capacity. I didn't care how long it would take me to build this company. I wasn't in a rush. so how did it go i think that first year we did well i mean we did like three or four hundred thousand dollars and that was enough to cover my 180 000 in overhead and whatever t and e travel and expenses and like you know computers or like just like stuff but like we did not pay rent for the first 18 months of the company we stayed there for six months and then there was a co-working space down in Debrosa Street by the Holland Tunnel called Sunshine Suites.

8:37They had this weird little non-office office and they wanted marketing and we bartered us marketing the space for room in this fake office. And so by keeping my expenses down, the reason I never feared it is pretty quickly we had months worth of runway plus I still had some savings personally and I was willing to dip into it. Got it. But talk to me in the beginning. There's still some, and again, it's interesting because I'm sure you see it like as you grow, the problems just change. It's not less problems. The problems just are more expensive. Yeah, little children, little problems, big children, big problems.

9:26No, the problems are bigger. Right, and more scary because there's a lot more to lose also. Yeah, I think for some people. I would tell you that I believe the definition of a purebred entrepreneur is having a much better relationship with that fear than most humans. Yeah. I'm really okay with losing it all. That scares me right now. Look, I prefer it not to happen. I don't want it to happen. I don't do behaviors that would make it happen. but if it happened it would feel as though it was because I deserved it and you can build something great again I think that's what you're saying but not even that yes I am saying that but let me say something more important I do not believe you're allowed to love entrepreneurship for just the good stuff if you really love this game you have to be in a position where you're willing to lose and if you lose you must take 100 % of the blame if I was to lose everything or get really hurt financially that would be my fault and I'm willing to die on that sword I'm willing to have the humility and the shame and the pain because I chose this course but it also really really painful so take me to the first time and I assume there is a first time where you're like oh my god can I make this It's like, can I pay the rent?

10:58I mean, there's things that pile up, right? Like there's lawsuits and people and complaints and whatever. Like, I don't know, like when you grow, like is there a moment where you're like, oh shit, this is hard? Not on the P &L part. Again, I'm too immigrant and it's too, like I do not do things that could put me out of business. I think the things that probably have hurt in growing a corporation is frivolous lawsuits have hurt. You know, like being a good person and having good intent and just watching people use California or New York law. Oh God, we have this now. We were like, I want to kill someone right now.

11:37You could see how you reacted. You could see everybody how she reacted. Like when you're really not trying to do the wrong thing and people are basically scamming you by using law. And you know, I don't mind to be scammed. When you're being scammed by the concept of you're not a good person. Like the company, you know, like, You should be scammed. But if you're actually trying to change the world and do good things, that sucks. Again, I don't mind if someone scammed me. I, much, much more painful when someone scams you by saying you did something wrong. That they are just using a legal loophole.

12:12Like, the sad part about America is like, the way lawsuits work in this country. Like, the amount of times my lawyer's like, I'd like to just settle this. I'm like, absolutely not. I don't care about the money. I am not letting someone create false claims and we will lose money on this because that's not nice. I don't care about the money. So that hurts when people are doing those kind of things. You know, look, it's lonely being at the top. There are definitely times where, you know, like, you know what's weird? Even today, like there's something about this gloomy weather. You notice how I mentioned it when I walked in?

12:49And even today, like a couple times during the day, I'm like, huh, I'm not an 11 out of 10 passionate for the way this day's going today. Oh, so we need to fix that. No, it's good. But you know what's funny? Like me at an eight or nine feels like a zero. That's how much I love what I do. But I can feel I'm at an eight or nine today. And I fully believe it's the weather, by the way. Like truly, actually. Which is like really weird to me. I'm like starting to realize why people move to Florida. I'm like, oh, I get it. But it was really interesting. I've been thinking about it all morning. It's 1.23 p.m.

13:27right now. And there's days like this where I'm like, man, what would I be doing if I didn't have all these responsibilities? I thought about this literally today. So I think when you're building something, every day has the potential to be hard even when there's nothing crazy going on. There's nothing out of the ordinary going on today. there's 13 fires that are going on but they're all micro fires I would say like twos and threes which is small out of to 10 and yet I find myself like can't wait to it being 7 o 'clock tonight because then I'm going to go to the Knicks game with my son and my brother and my two buddies and I know myself it's not the game that I'm yearning for usually having something like that actually makes the work day much more enjoyable but I think this is important talk to everybody in the audience which is what I think the game's about is me getting through today.

14:24Like having the tenacity, the grit and most importantly, the ability to stomach uncomfortable days. I know what I'm feeling today is the thing that spirals people into negative places. Right. I can feel it. My ability to contain it, notice the numbers I'm using. I'm using them very specifically. My eight or nine out of 10 is what people would consider a one or zero. Like I'm depressed today. I'm anxious today. I'm unhappy today. I'm trying to think through every day as a human and a public figure who communicates things with the hope that it brings value to people of how to get people into a place of getting comfortable with not being comfortable.

15:09Right. I really think about, like what we're talking about, like your question, the answer is potentially every day. The answer to your question of, tell me a time, maybe every day, if I do not do certain things, we will run out of money and it will go out of business. Right. So how do you wake up in the morning and how do you, you know? The same way that a parent wakes up every day knowing that they're a mom and dad forever. Have you ever seen an 80-year-old parent and a 60-year-old like in public? It's fascinating. Like you're still a mom and dad forever. The same way that somebody much less fortunate than me, like how do I do it?

15:48By perspective. You know when people woke up this morning and lost a loved one last night? Right. Many. Do you know how crazy that is? Like I say these things because I want to really get people to think, like thousands of people in the last four hours since this tough weather day for me, thousands of people have had the most catastrophic thing that could happen to them in the world happen. The death of someone in their inner circle. So I really struggle with like, yeah, I'm having a challenging day, but this is what I think has led to a very big issue in our society. We have over coddled inconvenience.

16:33We have weaponized things like you know a tough day into things that like we're just we're just we just need to be stronger right how do i deal with it by knowing i have no choice so let's go there for a second because entrepreneurship yes um is very very hard and they're going to be moments if you will that are not bad weather but they feel like near-death experience they might not be but they feel very real take us to one I've never had that I don't want to bullshit you because I don't care enough I don't care about my businesses enough I want to be very very transparent with you I'd like I only believe that truth brings the most value to an audience I have never felt anywhere close to that when it's come to business what about layoffs because they can hurt that crushes me.

17:34See? But that doesn't feel like a near you know what I mean? I want to be I get it. I get what you're saying. Like the hardest thing for me definitely has been the interpersonal things and my lack of candor has in my early part of my career and the dominant part of my career has actually led it to be way more challenging. I actually am struggling way it's amazing. For 20 years of my career by not being able to tell employees that they're not doing a good job along the way led to the firing being very hard. Now, because the company is doing a much better job with critical feedback, it is shocking to me how much more comfortable I am with people getting fired because I feel like we've done the right, I didn't realize this, I couldn't see it.

18:19Now I feel like we're doing enough of the right thing by people that we're not surprising them. Before I thought I was doing the right thing by not scaring them day to day, but in essence the ultimate thing was happening which is I was surprising people. That's been a huge wake up call for me. So yeah, I mean I think the interpersonal stuff is, I'll be honest with you, what's even harder than that is I get from HR every day notes if somebody has lost a family member or is dealing with something traumatic. A miscarriage, a house burning down. That's tough. Like I'm getting constant, like I almost told, I told, we call it pet people, Experiences team instead of HR because I didn't realize HR had a bad brand so I don't want to call it HR at Vaynervon.

19:06I told the pet team the other day, I'm like, I might stop getting these because it's just fucking depressing. It's like, Johnny Thompson's aunt died. Ricky Thompson had a car accident. Sally Magoo had a miscarriage. It's like, fuck. You know, like the human part has weight, especially when you're an empath. Right. So yeah, that's been challenging. So, but talk to me first. a second about the balance between being transparent with your company or with the people around you and actually freaking them out if there is a fear of money. There's a real balance to it. That line from Jack in that movie, you can't handle the truth, is the number one truth to employees.

19:47Employees talk about wanting transparency. It's not true. That's, yeah. It's not true. It took me some time to find that out, by the way. Most of my friends that are overly transparent, I was saying that to them 20 years ago. There was that whole movement of transparency, especially coming out of Silicon Valley. I'm like, this is not real. That's true. This is not, in the same way that companies can't take political stances. Right. I mean, that was so humorous the last five to seven years. Like, there's not a single issue in the country right now that 50 % of my employees don't see it one way and 50 % see the other way.

20:21So what on earth, and by the way, my company is not a human being. I'm a human being. I have political views. But my company is not required to put out a statement on every rally or Supreme Court judgment. What are we talking about? Right. So, you know, transparency is very laughable. People are completely full of shit on this issue. We want transparency that's convenient or feels good to us. That's true. Or allows... When everything is good, they want transparency. We want transparency to cast judgment on others. Ouch. Yes. That is, if we want to get to the part that nobody wants to actually say out loud, you want transparency because you want to cast judgment on others.

21:11I notice that people that call for transparency are really also very big on privacy and don't want their shit out there. Yeah. Speaking of conflicts. So, yeah, I think I try to find a balance. And I do think there's balance. I also don't think holding everything and not telling your company what's going on is a problem. But I think about it all the time. And I think my leadership team has learned a lot from me on this issue because I do think a lot of them over the last five to seven years when corporations got socially more liberal, they wanted me over coddling and over transparency in places where I think ultimately they've learned that it was great that we didn't.

21:56In a place where we're very good at over coddling and we're very good at being overly transparent, there's lines in the sand that if you cross, you actually create much more damage. Amazing. That makes sense. And that's interesting because I did come from the Silicon Valley. Be transparent, be transparent. But then everybody freaks out. I'm like, where did you go? I'm like, so yeah, I learned my way. But talk to me a little bit about when, you know, as you were growing VaynerMedia, do you go back to your why to regret? Like, how do you motivate yourself? Or what are some of the ways that our listeners, if they're going through hard moments, looking for jobs, getting rejections, debating what's next?

22:43Like, how can they motivate themselves? I get 100 % of my motivation from gratitude. I just do. You know, when you were asking that question, I was going through my brain of like, what do I do? Like, I really want to give good answers here. What do I do? In times of trouble, in times of pushing through, I always just go to gratitude. It's why I was able to answer to you why I don't fear on the business stuff. Like, I go so basic on the health and wellness. Notice my analogies. I can't be upset because look what happened in the last four hours people lost love I go there that's all I've got health over everything none of this matters if I lost all my money and had unlimited ridicule as a public figure for not being as good at business as I thought I was I wouldn't care how does it not hurt you?

23:36how do you create a thicker skin? by realizing that anyone who let's say it all crashes and burns Let's use you. Oh, darn it. Let's use you in my crashing and burn. Oh, okay. No, I can crash and burn with you. Let's use it. You wake up in 16 weeks and you read headlines. Gary Vee has gone bankrupt. All the companies went to zero. He over leveraged himself. All this stuff. My intuition in the limited way that I know you is that your first move of action would not be to go to Twitter and be like, ha, ha, ha, Gary Vee. I knew it. No, I'm like, let's partner, dude. I have some ways to make money. Let's go.

24:20You understand? Yeah. How do I deal with it? I have so much empathy and compassion and sympathy for humans that would go on the internet to cheer on my grieve. Their lives are in such a bad place. That is true. That I can't conjure up the feelings to be upset for myself in a world where I know even if I went to zero, I would never do that to someone else. I'm too grateful that my mom built me this way. I'm too grateful that I don't have that poison, that envy, that jealousy as a currency through my life. Because I do not value the opinions of losing players. Right. And the only goal should be peace of mind.

25:15True. The only goal that everyone here who's watching should get to is living a life where you do not have stress on your chest. And that is achievable. Here's why. The wrong stress because you have a lot of stress. Correct. But my stress is really. But it also makes you happy. Yeah. Correct. That's like playing sports and there's three seconds left and you're losing by one and you're nervous but you're also excited. to take the last shot. All my stress, to your point, is good stress. There are people really, really anxious out there, and it is completely framed up by a lack of accountability and a lack of perspective.

25:55People can change, and I spend time thinking about that. But let's talk for a second, because I think it is important, because there are people that are building companies, and the mental stress or the mental anxiety is taking them down. Because their identity is wrapped up in the success of that business. Sure.

26:17I do not view myself as Gary Vee, the entrepreneur. I view myself as Gary Vaynerchuk, the nice human being. In my soul, my validation to myself, the way I judge myself, because we all judge ourselves, is do the people that know me think I'm a good human being? Yes, and you still decided to be the nice human being that doesn't sit on the beach all day. Correct. And drinking margaritas. Because I love the game. This is my joy. Right. I could not imagine working for someone. I could not imagine not doing anything. People that try to make money to go on a beach and drink margaritas are always the people that do not make money.