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A
I 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.
B
Right.
A
Stop being full of shit is what I'm basically saying. I'm really trying to get there. Don't say that. This is your. This lady. She's like, mama. This is mama's money making thing. And she's like a friend of mine. Three weeks later, I checked, I could see. I was like, what happened to Mama? She's like, oh, it's hard. I'm like, no, shit, it's hard. What do you. I just think that people are wildly entitled. Like, 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.
C
Oh, yeah.
A
Like, I don't understand how people understand it's hard. Like this concept of easy.
C
And it's beautiful. It's hard and it's beautiful.
A
It's beyond. 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.
C
I'm very glad I don't need to change those anymore, let me tell you.
A
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.
C
It's the most important one, though.
A
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.
C
I want to take you back to probably somewhere around, I don't know, 2009.
A
Yeah.
B
And.
C
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. You already built this thing. Wine library. Right. To a big, you know, to what it is. But. And I think it went from what, 30 million to 60 million or 3 million to 60 million, right?
A
Yep.
C
So. But now you have this decision. You're seeing. Seeing something that maybe more companies will need this.
A
Yes.
C
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.
A
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. I 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 than me that was graduating college who looked to me as someone who he wanted to do something with. So I. I had a lot of life events going on, and I had skills and I had vision. I did see that social media was gonna eat up the world and become a major part of society, let alone marketing. You did 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. 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 Lazzaro.
C
Ah, we're gonna see them in two hours. Amazing.
A
So they were just here.
C
You could see shoveling shit.
A
This 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. So I couldn't afford rent for my company, nor could I afford paying anyone. So our first three employees were interns, all friends of my brother. But because it was spring of 09, the economy had just collapsed in 08, 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 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 lead to your customers. That'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.
C
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.
A
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.
C
And that's pretty incredible because they're not in a big spot by then. They have a small office, and at that point, they're giving you their.
A
It was half the size of this, for context.
C
Okay, so that's your office when you get started. Now, you decide, if I'm not mistaken, not to raise capital.
A
Correct?
C
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.
A
I believe that most companies and most people are unhappy and lose because they don't think in terms of saving money.
C
Tell me more.
A
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 traveling 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 De Brosa street by the Holland Tunnel called Sunshine Suites. They 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.
B
Got it.
C
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 problem just are more expensive.
A
Yeah. Little children, little problems. Big children, big problems. Like. No, no, the problems are bigger.
B
Right.
C
And more scary because there's a lot more to lose also.
A
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.
B
Oof.
C
That scares me right now.
A
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.
C
And you can build something great again. I think that's what you're saying.
A
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 to where you're willing to lose. And if you lose, you must take 100% of the blame.
B
Yeah.
A
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.
C
But it also really, really painful. So take me to the first time. And I said assume there is a first time where you're like, oh my God, can I make this? Like, can I, can I pay the rent or do you. I 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, this is hard.
A
Not on the P and 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, oh.
C
God, we have this now. We're like, I want to kill someone right now.
A
You could see how you reacted. You could see everybody how she reacted. 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.
C
But if you're actually trying to change the world and do good things, that sucks.
A
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. The sad part about America is the way lawsuits work in this country. 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? 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.
C
Oh, so we need to fix that.
A
But you know what's funny? Me at an 8 or 9 feels like a 0. That's how much I love what I do. But I can feel I'm at an 8 or 9 today. And I fully believe it's the weather, by the way. Like, truly, actually, which is really weird to me. I'm 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 1:23pm right 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, you know, 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 seven o'clock tonight. Cause then I'm gonna 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 workday 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. Is me getting through today. 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.
B
Right.
A
I can feel it, my ability to contain it. Notice the numbers I'm using. I'm using them very specifically. My 8 or 9 out of 10 is what people would consider a 1 or 0. 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.
B
Right.
A
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.
C
Right. So how do you wake up in the morning and how do you know?
A
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. You're still a mom and dad forever. The same way that somebody much less fortunate than me, how do I do it? By perspective. You know, 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 cause I wanna 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. We 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.
B
Right.
A
How do I deal with it? By knowing I have no choice.
C
So let's go there for a second because entrepreneurship, yes, is very, very hard. And there are 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.
A
I've never had that. I don't want to bullshit you, okay. 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.
C
Okay, what about layoffs? Because they can hurt.
A
That crushes me.
C
See, I talk to your.
A
But that doesn't feel like a near. You know what I mean? I want to be.
C
I get it.
A
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. Now I feel like we're doing enough of the right, right thing by people that were 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, right? Like I'm getting constant. Like I almost told. I told. We call it pet people experiences team instead of hr. Cause I didn't realize HR had a bad brand. So I don't want to call it HR. At Vayner, I 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 and Sally Magoo had a miscarriage. It's like, fuck, you know, like the human part has weight. Especially when you're an empath.
B
Right?
A
So, yeah, that's been challenging.
C
So. But talk to me for 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 there's.
A
A real balance to it. That line for Jack in that movie you can't handle the truth is the number one truth to employees. Employees talk about wanting transparency. It's not true. It's not true.
C
It took me some time to find that out.
A
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.
C
That's true.
A
This is not real. In the same way that companies can't take political stances.
B
Right?
A
I mean, that was so humorous the last five to seven years. 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. So what on earth. And by the way, my company is not a human being.
B
Right?
A
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 judgement. What do we talking about?
B
Right.
A
So, you know, interesting. Transparency is very laughable. People are completely full of shit on this issue. We want transparency that's convenient or feels good to us or allows when everything is good.
C
They want transparency.
A
We want transparency to cast judgment on others.
C
Ooh, ouch.
A
Thankful. 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. I notice that people that call for transparency are really also very big on privacy and don't want their shit out there.
B
Yeah.
C
Speaking of conflicts.
A
So, yeah, I think I try to find a balance and I do think that 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. In 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.
C
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? So, yeah, I learned my way. But talk to me a little bit about when, when, you know, as you were growing vaynermedia, do you go back to your why to regret? To 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, like, how can they motivate themselves?
A
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. Like I go so basic on the health and wellness. Notice my analogies. I can't be upset. Cause look what happened in the last four hours. People lost me.
C
Wait, wait, wait. I saw that.
A
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.
C
How does it not hurt you? How do you create a thicker skin?
A
By realizing that anyone who, let's say it all crashes and burns, let's use you.
C
Oh, darn it.
A
Let's use you in my crashing and burn.
C
Oh, okay, no, I can crash and burn through with you. Okay with you.
A
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 to be to go to Twitter and be like, ha ha ha. Garyvee. I knew it.
C
No. I'm like, let's partner, dude. I have some ways to make money. Let's go.
A
You understand?
C
Yeah.
A
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 grave. Their lives are in such a bad place.
C
That is true.
A
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.
B
Right.
A
And the only goal should be peace of mind.
B
True.
A
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.
C
The wrong stress. Because you have a lot of stress.
A
Correct. But my stress is really.
C
But it also makes you happy.
A
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, you know, anxious out there, and it is completely framed up by a lack of accountability and a lack of perspective. People can change. And I spend time thinking about that.
C
But let's talk for a second, because I think it is important, because there is. There are people that are building companies, and the mental stress or the mental anxiety is taking them down because their.
A
Identity is wrapped up in the success of that business.
B
2.
A
I 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?
C
Yes. And you still decided to be the nice human being that doesn't sit on the beach all day.
A
Correct. Drinking margaritas because I love the game. This is my joy.
C
Right.
A
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.
Podcast Summary: Ilana Golan x GaryVee: Building a $300M Business the Hard Way
Episode Title: Ilana Golan x GaryVee: Building a $300M Business the Hard Way
Release Date: July 22, 2025
Host: Gary Vaynerchuk
Guest: Ilana Golan
The episode kicks off with Gary Vaynerchuk (hereafter referred to as Gary) emphasizing the critical role of grit in achieving entrepreneurial success. He observes a common trend where many individuals meticulously plan their ventures but lack the perseverance to execute them effectively.
Gary [00:00]: "I 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."
Gary underscores the importance of honesty and commitment, critiquing those who make grandiose plans without the dedication to follow through.
Gary [00:10]: "Stop being full of shit is what I'm basically saying. I'm really trying to get there. Don't say that."
Ilana Golan shares her personal journey of building a $300 million business, highlighting the challenges and adversities she faced along the way. She reflects on her early years, dedicating extensive hours to grow her family's wine business, only to find herself at a crossroads emotionally and financially.
Ilana [02:34]: "I think adversity is the foundation of success. I had accomplished my first goal in life, which was to build a big business for my family. What I had not anticipated was the bind I found myself in..."
Ilana discusses the decision to start her own agency during the economic downturn of 2009, showcasing her scrappiness and resourcefulness in leveraging limited resources to kickstart her venture, VaynerMedia.
Ilana [04:44]: "I started vaynermedia in the conference room of their company, Buddy Media, in 2009. So I couldn't afford rent for my company, nor could I afford paying anyone. So our first three employees were interns, all friends of my brother."
A significant portion of the conversation delves into the importance of financial prudence. Ilana reveals how she meticulously managed the company's finances, prioritizing essential expenses and avoiding unnecessary costs to ensure longevity.
Ilana [07:48]: "Every time we got money, including that first $30,000, we spent only 15,000 of it. I wasn't hiring ahead of our capacity. I didn't care how long it would take me to build this company."
Her approach allowed VaynerMedia to sustain operations without immediate reliance on external capital, showcasing the power of disciplined spending and strategic resource management.
Gary and Ilana explore the psychological aspects of entrepreneurship, particularly the relationship with fear. Ilana candidly shares her perspective on fear, emphasizing resilience and accountability.
Ilana [09:31]: "I believe the definition of a purebred entrepreneur is having a much better relationship with that fear than most humans."
Ilana articulates her willingness to accept the potential of failure, taking full responsibility for any downturns, and maintaining a focus on peace of mind over financial success.
Ilana [10:26]: "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."
The discussion shifts to leadership dynamics, particularly the balance between transparency with employees and maintaining organizational stability. Ilana reflects on her journey towards effective communication, recognizing the pitfalls of over-transparency and the challenges of delivering tough feedback.
Ilana [19:39]: "Employees talk about wanting transparency. It's not true. It's not true."
She emphasizes the importance of selective transparency, advocating for open communication that fosters trust without causing unnecessary panic or confusion among team members.
Ilana [22:46]: "I get 100% of my motivation from gratitude. I just do."
A poignant part of the conversation focuses on mental health and resilience. Ilana discusses the emotional toll of leadership, especially when dealing with personal hardships of team members, and the importance of maintaining a strong mental framework.
Ilana [25:16]: "Health over everything. None of this matters."
She advocates for a balanced approach to stress, distinguishing between detrimental anxiety and productive stress that fuels performance.
Ilana [25:34]: "All my stress, to your point, is good stress. There are people really, really, you know, anxious out there, and it is completely framed up by a lack of accountability and a lack of perspective."
The episode concludes with Ilana reinforcing her fundamental values, prioritizing personal integrity and peace of mind over mere financial gains. She challenges the conventional notions of success, advocating for a life where stress does not impede one's well-being.
Ilana [26:13]: "I do not view myself as Gary Vee, the entrepreneur. I view myself as Gary Vaynerchuk, the nice human being in my soul."
Her closing remarks serve as a powerful reminder that true entrepreneurship is not just about building a profitable business but also about fostering personal growth, resilience, and a positive impact on others.
This episode offers deep insights into the complexities of building a successful business, emphasizing the indispensable qualities of grit, resilience, and integrity. Ilana Golan's candid reflections provide valuable lessons for aspiring entrepreneurs navigating the tumultuous journey of business creation.