Gary Vaynerchuk is the chairman of VaynerX, a modern-day media and communications holding company, and the active CEO of VaynerMedia, a full-service advertising agency servicing Fortune 100 clients across the company’s 5 locations.

In the late 90s, after identifying “the internet” as a land-grab opportunity, Gary transitioned his father’s local liquor store into one of the first wine e-commerce platforms resulting in growing the family business from $3-60MM in sales during a 5-year period.

Gary is considered one of the leading global minds on what’s next in culture, relevance and the internet. Known as “GaryVee,” he is described as one of the most forward thinkers in business – he acutely recognizes trends and patterns early to help others understand how these shifts impact markets and consumer behavior. Whether its emerging artists, esports, NFT investing or digital communications, Gary understands how to bring brand relevance to the forefront. He is a prolific angel investor with early investments in companies such as Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase and Uber.

Gary is an entrepreneur at heart — he builds businesses. Today, he helps Fortune 1000 brands leverage consumer attention through his full service advertising agency, VaynerMedia which has offices in NY, LA, London, Mexico City, LATAM and Singapore.

In addition to running multiple businesses, Gary documents his life daily as a CEO through his social media channels which has more than 30 million followers across all platforms. His podcast ‘The GaryVee Audio Experience” ranks among the top podcasts globally. He is a five-time New York Times Best-Selling Author and one of the most highly sought-after public speakers.

Ian spent a day with GaryVee and his team in Vayner’s Los Angeles alongside David Moeller, the founder of Keep Technologies. In this two-part episode, we talk about how that experience came about and what it was like meeting GaryVee.

Watch the episode here

Listen to the podcast here

Meeting With GaryVee – Part 1

A Behind-The-Scenes Look Into Our Day With VaynerMedia

No matter what your ambition is, whether we’re starting tomorrow, whether we’re an employee, whether we have a huge company or haven’t even started and are starting next year, the one requirement for all of us is to have somebody’s attention. Before you can sell anything you need somebody’s attention. What you say in the written word, in audio or video becomes the variable if you are successful.

The reason I follow attention is if there was nobody in here right now and I was giving this talk, I would have no potential to achieve what I want. By the same token, with all of you in this room, what I talk about for the next hour and a half is the variable of my success. There are many of you here that don’t know who I am. You’ll leave with an opinion. There are many people who do know who I am. Whether going to like me more or like me less is completely predicated on the content that I put out.

I spend my life in a very basic mind frame. If you look at the politics of your country or my country and if you look at the businesses, it’s all one very simple game. Do you understand where the people are and what they are consuming? Do you understand how to do the written words, the audio or the video to put on those platforms? This is how it has always been. It’s television, radio, print and outdoor billboards. It’s always been the same game. Where is the attention, the eyes and the ears? What is our capability to put content in it?

As Ian gets ready to market his product for the tech startup Keep, we are looking for ideas in any way we can to get attention, and how we can be a little bit more persuasive. Everything is going to be digital, and this is not exactly my expertise or the expertise of anyone on our team at Keep. What we did is we went out to Los Angeles, to the VaynerMedia West Coast office. We met with Gary Vee who is a serial entrepreneur and tech investor. Most importantly, he is an incredible marketer.

He has a large marketing agency. They focus on social media, where to spend money, how to get the best returns, how to grow brands, how to build a presence, and all the things that we’re trying to do. We spent three days out in Los Angeles, one full day with Gary Vee and his team. This episode is all about how that came to be, how we set it up, and what that first day looked like. If you are new to this channel, please subscribe. If you are one of our long-time readers, and you’ve not given us a five-star review, shame on you.


Ian, you son of a bitch. How are you?

I’m doing great. It’s a beautiful day here in Virginia. I’m a little sore. We’re talking about my trip. Before we even start off, I can tell you, I don’t do as well on five and a half hour flights as I used to. Especially when I have to do two of them in three days. I got to get up and stretch my hamstring. My back was hurting me. I had to stretch for ten minutes when I got off the plane to walk through the airport. Everything hurt, my knees, my muscles and my back. I’m old.

Flying first-class is a real bitch.

It still sucks. It’s a lot of sitting.

Invest in experiences and invest in yourself. Click To Tweet

Direct flights are awful. Years ago, that trip would have taken the whole month.

There’s a reason why I only fill my gas tank up once a month and I don’t go anywhere anymore. I do not like traveling. I have no idea how I used to be able to get on four airplanes a week for months at a time. That was my life. What was I doing? That’s stupid.

Ellie texted Jenny. He goes, “Do you want to come down? Let’s get together and we’ll do something fun.” She’s like, “No. We don’t leave for a get-together.”

We don’t leave the bubble. Someone told me that the gas prices were high and I’m like, “Really? I don’t fill my tank up so I wouldn’t know.”

My doctor is going from an 8-minute drive to a 22-minute drive on the other side of town. The first thing I thought of is, “Should I find a new doctor?” He is 22 minutes away.

My office is eleven blocks from my house. I could easily walk it, but I drive it because I’m lazy.

I work in my office, which is in my house, which is seventeen steps from where I sit.

You didn’t even move. You did it right from your office.

My office is a bit too far from me. It’s about eight minutes from the office and I’m moving to a new office, which is one turn on my driveway. We’re going to talk about trips, business travel, cool experiences, and investing in yourself. I wore this t-shirt for two specific reasons. Do you know why?

It’s because you look handsome in it.

LMSM 61 | VaynerMedia

VaynerMedia: We are looking for ideas on how to get attention and be a little bit more persuasive.


That’s the third reason.

You’re being humble.

I was watching the old Seinfeld and he goes, “This is the golden boy and the golden boy lost out.” It was his favorite t-shirt and it’s starting to fray so he had to pitch it. I bought this t-shirt shit face drunk for $140 in Vegas. We were at the pool all day. I refused to throw the shirt out. It is a constant reminder of overspending because I’ve overspent. I still have this t-shirt years later and now I’m in all kinds of stuff. We’re not going to Vegas. We’re not taking those kinds of trips. I’m not investing at the moment in experiences. It’s hard to do them after COVID anyways. To me, this was a homage to having that experience.

Can we stay on that for one second? You said you overspent, but you love that shirt or you would have thrown it out years ago. You don’t wear that just for sentimental reasons. You love that shirt. You had it for years. I would say that you got an incredible value out of that. How many shirts do you spend $40 on? You wear it once. You wash it and you’re like, “This thing looks like shit. It doesn’t fit me. It got tight and you give it away to charity.

I would say that it didn’t feel anything at the time because you were blacked out when you bought it. At the time, it might have felt like a big expense but it most certainly wasn’t. This whole episode is about that. When you bought that, you didn’t know you would have it for years. You knew you were buying a quality item. You didn’t know how much you would like it. Everything that I did is a little bit in that vein. I don’t know what it’s going to do for me over years or days, but it felt like the right thing to do at the time.

That’s the thing about both experiences and investing in yourself, which this t-shirt was neither but it turned into one. I was ass-backward stumbling, but the point is we’re going to talk about investing in yourself and your experiences. Let’s start at the top. Ian, how was your flight? Where did you go?

I flew to Los Angeles. I flew out there early in the morning. We were out there to meet with Gary Vaynerchuk and his VaynerMedia team. They do a digital deep dive for companies like our startup companies, smaller companies, small businesses and medium businesses that are looking to put a marketing strategy together.

For those of you who are not podcasters, you might be surprised by this little nugget. We usually record 2 to 4 weeks before we release, and that’s because of production, uploading and getting everything right so we don’t miss dates. This happened at the very end of October of 2021. This will probably come out three weeks from now. The point is October is also the best time of the year for what?


Ian and I bonded for the first time over baseball. It turned out we had very similar lives. We have granddads who loved to talk about baseball. Ian decided to go to the Dodgers game. Why don’t you talk a little bit about that, when you’re flying out there?

When you realize something could be historic, you may as well stand up. Click To Tweet

We’re going out there. It was a short trip. There are a lot of these deep dives that companies put on. Wednesday was the full day. It was eight hours of meetings that day, including a couple of hours with Gary Vaynerchuk himself. We got in the day before and we landed at 1:00. There was a dinner the night before with all of Gary’s executives.

There were only five companies there and no one else brought two people because we had to pay for two seats to this. In DC, as I’m boarding the plane, I see this dude with a Braves jersey and hat. I’m like, “The NLCS or the National League Championship Series is going on.” That dude is going there to watch the Dodgers and I’m going to LA. I pull up my phone and I’m like, “That sucks. The game is at 5:00 and our dinner is at 7:00.”

You then realized you have a time change too.

I’m like, “No. That’s a three-hour difference. That’s a 2:00 start.” I start texting Dave. David is not a huge baseball fan but he lives in Atlanta. If he has a team, it’s the Braves. I’m like, “The Braves and the Dodgers are playing. This is a ridiculously good series. We should look into it.He’s like, “Check.” I’m on the plane on wifi looking for tickets and WhatsApping Dave who is also on wifi on a plane. We’re both in the air on the way to LA, WhatsApping each other. I’m like, “I can get us bleachers for $100 or I can get us $500. That’s a club level in the outfield or it’s going to be about $1,300 if you want to be right over the dugout.”

He’s like, “I’m not the last one. I’m not a baseball fan. I know what you’re doing. You probably wanted the middle one so go ahead.” I bought it on StubHub. We landed, dropped our shit off at the hotel, and had an Uber waiting to take us there. We didn’t get to the game until the second inning. If you don’t follow baseball, the Dodger Stadium is the largest capacity stadium. It’s a gorgeous cathedral of a park.

It’s 72 degrees in Southern California, not a cloud in the sky. The sun is bright and it’s 2:00. Everyone there is in a t-shirt and jeans. You’re not hot in jeans and you’re not cold in a t-shirt. California’s weather is out of control. Our seats came with free food. Maybe I overpaid for the seat for $500 a seat but I got a free helmet nachos and a couple of hot dogs out of it. I feel like that’s pretty good value.

It’s pretty cool because I have a very cool experience with baseball stadiums. I’m a Red Sox fan. I’ve been to Fenway probably six times. My best example is the first time I ever went and the time I brought my granddad. It stuck in my brain. I went to Wrigley for the first time, which is a cool experience. At the time, I went with you for the first time, which was awesome. It was a day of partying. It was a freaking blast. I don’t even think we went to the game, we just partied but it was a blast. The other thing that stands out for me baseball-wise is there’s a picture that I’m in that’s probably in the hall of fame. It was the first picture of the first pitch of the Nationals. I was standing there and I was with Lee. The next day, the back of my head is on the front page of the Washington Post.

That wasn’t even their new stadium.

It was the old stadium. I was also at the first-ever game for the Marlins. Case in point, I’ve been in the cool things but those don’t come up.

LMSM 61 | VaynerMedia

VaynerMedia: Dodgers stadium is a gorgeous place to watch a game.


That’s a small side note in the history of baseball, the first-ever Marlins game. It’s a very small footnote. They are not in the Hall of Fame.

The other thing I remember is the time I was in LA and I went to Dodgers Stadium. It’s incredible. It’s a beautiful place. It’s a gorgeous place to watch a game. It’s neat but what I’m getting at is I was there for something important years ago, and what I remember is the Dodgers game.

My feelings are a little hurt that you didn’t bring up Comerica in Detroit where I’ve dragged you to multiple baseball games. My friends are a little hurt that you didn’t bring up seeing the mighty Detroit Tigers play multiple games for Fantasy Football drafts. What I’ll also say about Dodger Stadium with all of those things is you mentioned Wrigley and Fenway. Fenway has a 37,000 attendance capacity. Dodger Stadium is 56,000. It’s like a football stadium for baseball. It’s normally half empty because people can’t get to it. In a regular-season game, it’s hard to fill that but seeing it fall for a playoff game was neat, but we saw the best part of the game.

We were debating whether to blow off the VaynerMedia team the night before and not go to the dinner and stay at the game because it was fun. We stayed until the eighth inning. We watched Albert Pujols strikeout and I’m like, “We saw Albert. Let’s get out of here.” We leave while the Braves are winning 5 to 2. As we’re leaving the stadium, we’re hearing the crowd making noise. They got a walk and they got a single, and then Cody Bellinger hit a three-run home run.

There was nothing the crowd had to cheer for the whole game. As soon as we’re getting into the cab, the crowd goes crazy. We’re like, “Turn the radio on,” and they are like, “Bellinger with the majestic blast.” We’re disappointed. We missed the best play. We missed the Dodgers comeback which was hilarious. The next day on the MLB social media, they posted the clip and the announcers are going like, “A lot of people who left are trying to get back in the stadium, I’m sure.” The other one goes, “You can’t leave a playoff baseball game early.” I’m like, “That’s shit. Yes, you can.”

The way we’re going to wrap this whole session is by talking about the difference in business travel when you own a business versus when you’re doing it on somebody else’s time. I don’t want to get to that yet. What I would want to get to is this. It’s 2004, 2005 or something like that. The Nationals are having their first game. They have had a team for years. They moved away from Washington DC. Washington DC is a big baseball town. I had a commitment. I was supposed to go to a recruiting dinner. I was supposed to host new recruits who are coming to this dinner. Back then, this is what you did. It’s similar to what you deal with. The night before, there’s a warm-up dinner. The next day, there’s a bunch of interviews.

The way we used to do it back then is with one manager, me. I would be at the dinner and bring a handful of people with me. I had my chosen guys that I would bring. It was all men at this point. It’s all project managers and construction staff. There will be a group of college graduates that were there. I got a phone call from my friend. He goes, “I got tickets for the game tomorrow night. Do you want to go?” I already had a commitment. I remember thinking to myself, “I probably shouldn’t do this.” I’m weighing it back and forth.

One of the guys, his named Jeff Ratliff, is with me. He comes to these dinners all the time. I was like, “I got a chance to go to this game right behind home plate. It’s going to be epic. I want to skip the dinner. Can you run it?” He goes, “Sure.” I’m like, “What do you want?” He’s like, “I want a program.” First of all, I had dinner and decided to skip it. We get to the game. I’m sitting with the guy who bought the tickets. He invited me. I’m like, “Do you want to stand up for the first pitch?” He’s like, “No.” I stand up.

Two things happened. I skip dinner. I don’t know if we hired anybody from that group or not. It doesn’t matter. I’ve ultimately quit the company so as Jeff Ratliff. It didn’t matter, but history was in front of us. I decided to go to a historical event versus a ho-hum another interview dinner. That’s step one. Part two is I stood up and I was in the paper. Fifteen people call me the next day going, “You’re in the paper.” My buddy, you could see the temple of his head. All you could see was his hairline because he didn’t stand up. He would have been in the paper too.

Sometimes you have to realize that there’s something cool. It could be historic and I’m here. I may as well stand up. If those things happen, cool things can happen. My guess is you are probably going to get some cool nuggets from this meeting, but you and Dave we’re also going to talk about, “Remember that time when we went to that World Series or that NLCS game?” You go to a lot of those.

If you want to get into real estate, buy some real estate, do a deal first, then go to a seminar. Click To Tweet

You and I often talk. It‘s more specific to real estate or investing in general like a stock, a company or anything. What’s the downside? What’s the floor? We talked about our meeting with Shaq. We talked about some of the other investments that we’ve made. The floor here was if nothing comes out of this, we flew out to LA and had a fun ass time for two days, and had a great experience. Maybe that was an expensive experience but to me, that’s a pretty good floor.

If nothing else comes out of an event like this other than you’ve made some great memories, I’m not going to forget going to that Dodgers game 100%. I FaceTime my son from my seat at the Dodger Stadium the second I knew he was getting off of his football practice because it was three hours earlier. It blew his mind seeing me at Dodger Stadium because he’s a huge baseball fan. I can see it in his face because I didn’t tell him. I didn’t know I was going to do that. To me, it’s like, “If that’s all that came out of that, it’s worth it.

Before we get off of California, I want to do one more thing and then we’re moving into the meat of this. When I was a little kid, I didn’t grow up with significant means. Ian and I have both talked about going to California, which when we were kids was exotic. We couldn’t afford Hawaii or Europe as a family, but we could afford California and we did it.

My mom always wanted to go when but she never did. Ian talked about this similarly. They drove there and it was a miss. It was a very exciting drive and driving home was tiring. The point is I’ve always had a soft spot in my heart for California because of my mom’s love. She brought us there when I was impressionable. I was thirteen years old. It was cool.

Now, as an older person, I have incredible opportunities. Before COVID I used to go to California 2 to 3 times a year and it was like a fantasy camp for me. I’m always in a good mood there. I love it. I’m a guy who sweats. It’s October in Virginia and I’m sweating. I don’t sweat in California. It’s glorious and there’s all this beautiful stuff outside.

For me, one of the things that happened with COVID is I was in California when Trump spoke in the White House on March 11th, 2020 and March 13th, 2020 is when the borders closed out. The NCA Tournament and the NBA season got canceled. All of these things happened while I was sitting in California, one of my favorite places. Months later, I haven’t been back.

What I miss is that experience and I took it for granted because I was going there 2 or 3 times a year. My reason for bringing this up in this little soliloquy is to find things that you love that make you happy or make you passionate. When you’re there, don’t miss them. See them wide open. This was a completely different thing. You signed up for this experience with Gary Vee. Let’s talk about that. When and how much did you spend and why did you do it back then?

We’ve talked about this before on this. I’ll give you a quick background on it. David who I brought up before is a guy that I’ve worked with for twenty years. I worked with him at GE. He’s a serial entrepreneur and I’m a serial investor in his entrepreneurship. I’ve invested in multiple businesses with him. I have invested alongside him in this tech startup called Keep Technologies. We have a connected car alarm that has multiple sensors. We’re trying to do for the car space what Ring has done for homes. It’s security, safety and those things.

A few years ago, we were starting to talk about that we felt like our product would be ready in 2021. We were starting to think about how do we brainstorm, how to get as much attention as we can for this business when our product is ready, and how do we market. I’m a fan of Gary Vaynerchuk so I’d follow him on social media. I’m not the biggest fanboy of many people on social media, but he’s one that I enjoy following mainly because of other things that I’m involved in. I’m a writer and you have to post a lot of things on social media when you’re a writer. I have leadership programs. I sell direct-to-consumer businesses, which he’s very good at getting social media attention. He has a group within his company.

Gary started as a big personality. That’s what he was for a long time, but he ended up capitalizing on that. He became a speaker in the advertising world and the digital marketing world. He’s also created a business VaynerMedia, where they do a business-to-business advertising campaign. In essence, there’s the business of Gary, which makes its own money on social media of the business being popular like think Kardashians.

LMSM 61 | VaynerMedia

VaynerMedia: VaynerMedia helps you target differently using social media channels.


He makes money from advertising on that stuff. The bigger picture is he has an entire advertising agency that works with Procter & Gambles of the world and with big brands like General Motors. They have old-school thinking when it comes to marketing. They are still buying ads in newspapers and TV. He helps them modernize their spending and how to target differently by using social media channels.

That’s what VaynerMedia does and within VaynerMedia. Those are big clients. Those are million-dollar campaigns. They have the money to run massive campaigns advertising and he’ll do that. He also has a smaller group called The Sasha Group. His dad’s name is Sasha Vaynerchuk and his dad ran a wine store for a long time. Gary knew that people couldn’t afford VaynerMedia, which was smaller businesses.

He created the Sasha group for small guys like our companies, smaller companies. He would work with the Cava Companies. The Sasha group do marketing campaigns for smaller businesses. They will act as an ad agency, and they also do training in leadership. They host different seminars. This specific marketing workshop is called the 4Ds. You’d have to look it up. I’m going to slaughter it but its meaning is four words from Ds.

We found this a couple of years ago. David didn’t follow Gary but I said, “We need to get some thoughts.” David and I have sales experience but not a lot of social media marketing. We think that this product is going to do very well on Instagram, Facebook, Pinterest, and all those kinds of places because it’s a cool-looking image. We signed up for it.

At the time, it was going to be in New York years ago. It’s $12,000. It’s one day, fully immersive, small group, and there’s a good chunk of time you get with Gary Vaynerchuk. We were going to do it in New York. It was supposed to take place the second week of March 2020, and COVID hit. They called us and they were like, “We have to cancel it. We could give you a refund and do this digitally. We’re going to host a couple of digital 4Ds events.” We’re like, “We’re not that interested in that.” They were like, “Would you want to do it the next time we host one in person?” We said, “Keep our money. We’ll do it the next time you’d have one in person.” A year and a half later, this was their first live event and it was out in LA.

A few things. The 4Ds stands for Digital, Discovery, plus Deep Dive. According to the website, that’s what 4Ds are. Frankly, if you want to watch Gary Vee on your phone, the TV and on any mobile device, you can get him. Getting him in person is a different experience, so you decided to wait. Why don’t you tell us where you were in March of 2020 and where you were in October of 2021? That’s a big gap in a startup.

When we initially did this, we expected a product to be available in 2021. As it turns out, hardware is hard and we started going down a route where we didn’t like our product. We were racing to a ship date because of the date instead of building the right product. We put that on hold when a whole different route hired our own engineers. We were outsourcing some of the design in the production, but we are having to make too many compromises to get our product out fast.

At the time David had bootstrapped everything and I had put some f my own money in. The only money that was funding the business was seed money from us. In January of 2021, we closed on a $4 million round. We are now fully capitalized. At the time when we were going to go the first time to see Gary, we hadn’t raised the money yet. Our thinking was that this guy has got a big megaphone. We could get a lot of attention. We could show this a little bit from a self-marketing perspective. We could show some of the things that we’re working on.

When we talk to investors to raise a round, we’ll have done something like this. We’ll have some fresh ideas before we do that. I don’t know that we were close enough. We were early on discovery at the point. We didn’t have a prototype we could have brought to that New York meeting. It almost was helpful that COVID happened because we needed another year to get farther down the line.

Where we are at now, we had a full prototype. We brought our unit. We were able to show Gary the device. He was able to look at it. We’ve raised that capital. We have an engineering team of eight people in our Atlanta office. We didn’t have any of that if we have had done it before. Our production units are going to be ready by early summer 2022. Our first devices are going to be shipping. We’re in a perfect place where we are months from delivering units. It was a perfect time to go talk with VaynerMedia about different ideas that we could be doing right now to get our product out.

Most humans are good if they believe you are honest, and humans are not helpful if they believe you’re trying to be something you’re not. Click To Tweet

What is interesting about what you said is the creative process isn’t linear. When you signed up for this, you thought that it’s the right time to do it. The world went on hold and it turned out this might be a happy accident. You’ve put your name in the hat and this is the first live event back. My guess is if you signed up for it now, you would miss it. The product would have launched. Why don’t you talk a little bit about the adaptability and thinking, what you wanted to get out of it then, and what you talked about? You guys reset your funnel. You thought you had a need and want, and it changed drastically. I think that’s critical to success.

I think we’re farther along in marketing. If we had gone to New York in 2020, we either just say, “Got any ideas?” When you raise $4 million, $100,000 at a time, and you were one of those people I asked for money from. You were one of the easiest to ask for money because I talked to you all the time and you know my track record. A lot of people are like, “What’s your marketing plan? What’s your strategy? How are you going to go to market? Is it retail? Are you going to go direct to consumer?”

We’ve had to answer those questions so many times. We’re pitching at TechCrunch Disrupt on a stage. You have to talk about your marketing strategy as you go through it. I feel like our marketing strategy have been put through the wringer and questioned so much about it. It has forced us to study exactly how we’re going to go to market and capture as much attention as we can. This time, we came in with a plan and a strategy. We’ve already been spending money. We’ve had campaigns going on Facebook and Google Ads. We’ve purchased several different words.

We’re growing our waitlist every day by20, 30, 40 people signing up to get updates when our new product comes out. We’re trying to tap into various cohorts that are searching for car alarms, looking for car security, and that kind of stuff. I would say we were like, “Teach us about marketing,” a few years ago. This time we came in a little more confident of, “We’ve already raised the money and we already are marketing. What are we doing wrong? What could we do better? How do we optimize?” I would say that this is more iteration. If we had gone two years ago, it was 100% discovery.

What I heard in all that is you guys work every day and plugging away every day at this. David is a little bit more than you, but you’re very involved and invested. Because of that, it happens very fast in a startup. What happened was your quality of questions evolved. You had an evolution of what you needed from the meeting. Because you’re working hard, time wasn’t wasted. It is a happy accident that you got there when you did because of the fact that you could be more streamlined and specific with your questions, and the impact was going to be higher.

Something you said is important. For anyone who’s thinking about going to training for anything. Let’s say you’re saying, “I want to be in real estate. I’m going to go to a real estate seminar. Let’s say you want to learn about sales and you want to go get better at selling, or you want to be a writer and you want to go take a class. One thing that I always did at GE and at NVR, both big companies that I worked for, is I always taught a one-day sales class. What I found out is when people came too early, my class wasn’t the greatest. It was a lot of people taking notes and listening.

I would always set the timing up where you didn’t get training, you got on the phone with customers first. We would send you out there with no training so you could get your face beat in a little bit, so people could say no to you, so you could be ineffective enough to have burning questions when you showed up in my class. I found out that when we did that, my classes were awesome because everyone was raising their hands. I get people that say this to me all the time, “I’m going to get back to you,” and they never call me back. It happens to me all the time. What am I doing wrong? Whereas if they hadn’t sold before, they didn’t know to ask that question.

I would say the same thing. If you want to get into real estate, buy some real estate. Do a deal first, then go to a seminar and be like, “I screwed that up,” or “It’s not going exactly what I want,” or I’m overwhelmed. I’m spending too much time on things. Let me go listen to an operator who’s not overwhelmed.” In general, any training or investment you want to make in yourself or any investment you want to make in your team, don’t send someone to something like a blank canvas like a college student. Make them do it for a while and screw up. They will be so much more passionate about how they take notes and the questions they ask. That’s where we were at this deep dive.

There’s something else that comes up with what you said. I’ve talked about it here multiple times. I’m a big fan of the real estate community and the masterminds, especially the one that I’m a part of. I’ve been going to it for years now. What I did is I found one where most of the people were ahead of me. They were either in the same shoes as me or they were ahead of me. There’s a certain rung you must check. I barely checked the rung to get in, and then I was able to grow, meet people and do a launch.

LMSM 61 | VaynerMedia

VaynerMedia: The creative process isn’t linear.


Something else that happened at that first event that’s critical was this. I told you this at some point, but I considered inviting you because you’re smarter than anybody who worked for me. I was like, “If Ian will come with me, I’ll look better.” What I did when I got there is I brought the person who worked with me at the time. We didn’t seem as smart as we would have if I dragged Ian with me, but I immediately got help because we weren’t trying to be something we weren’t. We weren’t lying. We were being very honest. Someone was like, “I’ve dealt with that problem. I understand that problem.” If you have the experience and you can be truthful, and you put yourself in a room that’s appropriate, and if you curate your questions the way we’re talking about which happened by accident here, the impact can change.

I talk about this a lot with people. There’s something so powerful about being vulnerable and admitting that you need help. Humans are good by nature. I think most humans are good if they believe that you are honest. Humans are not helpful if they believe that you’re putting on an aura of something you’re not. The fact that you went to that and you were vulnerable, I was the same at this. I’m sitting at a table with a bunch of other startup folks that probably are not as well capitalized as I am in their bank accounts, but I was as vulnerable.

I would be like, “I’m bad at Facebook. Can someone help me? What am I doing wrong?” I would stick my hand up and say all this shit I was screwing up. We get to it later, but we were seven hours into this before anyone knew I had a podcast or that I wrote for Forbes or I had a pretty big following on LinkedIn. I didn’t share any of that because I didn’t want anyone to think I was bragging early and that I was showing up with the answers. I wouldn’t have paid all that money to go to this seminar if I had all the answers. I didn’t.

That’s a big thing that you see in a lot of instances in the Mastermind community that I’m a part of. People who show up humble. Jason, the Owner of CG always talks about checking your ego at the door. The goal of that is there are a lot of people in that room that are super successful and good investors. If you come in and you pound your chest on that, you’re not going to get help with the things that you need. You’re going to turn other people off. Gary Vee has a bigger footprint than either of us combined on every social media platform. You went in there the right way, humble and asking questions. In a one-day event, you have to make sure you get your spots filled. At the same time, you do it in a way that’s respectful and encouraging others. It’s almost a proof source, not the opposite, which is a brag.

It’s very important if you’re going to invest in yourself, if you’re going to spend money on training, or if you’re going to invest in your team. I have management training. It’s a twelve-week course. Frank’s team has been through it. You saw how I did this. I do this with every group. On the first call, I say, “You spent money to have me help you and you wouldn’t have spent money if you were all perfect. Let’s leave that at the door that I’m not perfect and you’re not perfect. The more vulnerable you are in these classes, and the more you’re willing to admit stuff that you’re screwing up or not doing well, the more you’re going to learn.

The best weekly calls I have with management teams are the ones where they are saying, “We’re not getting this right.” It’s not the ones where they’re like, “We’re good at this.” What the hell did you bring me in for? Let’s end the call. You’re great. Good job. Thanks for the check. Send me more money next week and you can tell me how great you are again. It’s better when you come there saying, “We’re okay here. We could be a lot better here.” That’s how I approached going out to LA. It’s like, “I’m not the greatest marketer in the world. I’m okay at it. I could be a lot better. I’m going to tell you all the areas where I’m not so good and I still want to be here to learn.

Let’s get into the specifics. What were the 2 or 5 things you and David wanted to get out of this meeting? Not the one you were supposed to have but the one you had.

We have a product that we’ll be shipping. We want to know how to invest our money in the smartest way to get the best outcomes. Our business challenge right now is how much attention can we get with the least amount of money spent prior to our launch. You say 2 to 5 and I’m sure there are a lot of other things, but that is my challenge specifically as the Chief Revenue Officer. If you take any funnel, there’s attention, interest and decisions. We don’t have enough attention. We need to widen our funnel and there are lots of ways to do it.

Let’s have some fun with this. Before you got on the airplane, what did you think the path was? What changed?

Our current path is we’re investing in Facebook and Instagram. We’re investing some money on Google Adwords. We’re running ads and all these. Our ad right now is a little cartoon explainer of our business. That’s been performing relatively well. We’re going to have an old-school approach of going right to retail. That’s a direct sale, B2B, get in the door with buyers like Home Depot, Target, Walmart and Best Buy. All the big retailers are a major part of our strategy, and selling through telecommunications.

You can't use a TikTok strategy or Facebook strategy on YouTube. Click To Tweet

All of those are major components of our strategy. We are as one-on-one as you can get on the social media ad spend. We are invested in some ads, trying to figure it out, and working the algorithm. We’ve not invested enough time in branding our company, what we want to stand for, and what messaging we want to do. We’ve not invested a lot of money in specific advertisements in what we could do. That’s our base floor now.

While you were there, what changed?

Going through the 4Ds agenda, they start off by going through each platform like Instagram, YouTube, TikTok, the big ones and a lot of that different stuff.

Let’s stop there. You said Instagram. Give me the top four they went over.

YouTube, Facebook, Instagram, TikTok and LinkedIn. Those are probably the five that they’ve spent a lot of time on.

Can we do this? Let’s talk a little bit about how they work. My guess is you work with people who understand this better than anybody.

The one thing I loved is they had a social media continuum that they were talking about. The search versus browse for social media, and knowing why you’re there. YouTube and Amazon are for people that are like, I know what I want. When you go to YouTube, you don’t just go through a home feed and look at anything they show you.

LMSM 61 | VaynerMedia

VaynerMedia: A major part of our strategy is selling through telecommunications.


It’s unlike Instagram where you’re blindly going, “Whatever is getting shown to me, I’m flipping through. When you go to YouTube and Amazon, take my business for example. You’re typing, “Car alarm” or “What’s the best car alarm?” You’re comparing a Viper car alarm versus the Club or whatever it is. You’re typing those kinds of things in. Those are searched social media.

YouTube is the second biggest search engine in the world aside from Google. They are both owned by Google, versus browsing which is more, “I’m browsing. I’m here because I enjoy being on the platform.” Those are Facebook, TikTok and Instagram. Those are very different reasons why people go there. It’s silly I’m going to say that’s an a-ha moment. When you hear it, you’re like, “That makes sense,” but I hadn’t been thinking about it that way. I hadn’t thought of it as a continuum

Somewhere in the middle is Twitter and LinkedIn. In LinkedIn, you might be searching a little bit but you’re also scrolling. LinkedIn is probably the place where I’m most active so I know that. That might be why that was a-ha for me because I spend the most time on a platform that’s in the middle. Whereas the other two are very different. They were talking about how if you’re not thinking of your strategy differently in those, you’re going to fail on one or the other. You can’t use a TikTok strategy or Facebook strategy on YouTube or Amazon. YouTube has got to be very built for answering questions because that’s what people go there for.

That wraps up part one of the meeting with Gary Vee and his VaynerMedia team. In part two, we dive into all of these social media platforms, and the advice we got from VaynerMedia on how Keep could do a better job of building our brand marketing. In part two, we get into the big entrance of Gary Vee with multiple cameras, and what it’s like to be in a VaynerMedia office when Gary Vee walks in, and the circus that follows that incredible guy around. Hopefully, you tune in to part two where we get into the meat of our conversation with Gary.

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