[00:00:00] Karlee: Welcome to Leave Room for the Magic, a podcast that invites you to embrace the wonder, beauty, and messiness woven into the fabric of everyday life. In this show, we'll bridge the gap between the practical and the spiritual, providing inspiration, tips, and tools from our featured guests. So without further ado, let's go make some magic.

Welcome, my loves, to the season one finale of Leave Room for the Magic podcast. This episode is THE definition of leaving room for the magic and the universe surprising me beyond my wildest dreams.

I have a very special guest for you on this episode, plus a bonus episode to follow that you won't want to miss.

On this episode, my guest is the one and only, and I can't believe I'm saying this, Gary Vaynerchuk.

Gary is a serial entrepreneur and serves as the chairman of VaynerX, the CEO of VaynerMedia, and the creator and CEO of VeeFriends. 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 consumer behavior. He is a prolific angel investor with early investments in companies such as Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase, and Uber. Just a few companies you may have heard of.

In addition to running multiple businesses, Gary documents his life daily as CEO through his social media channels, which have more than 44 million followers and garner more than 300 Million monthly views and impressions across all platforms. His podcast, the GaryVee audio experience ranks among the top podcasts globally.

He is a five times New York times bestselling author and one of the most highly sought after public speakers. He has another book coming out in 2024, and I will put a link for that in the show notes.

Social media is where I first learned about GaryVee, and I have been following his journey for about 8 years now. You've heard me reference many times throughout this season that I have dreamed of having a podcast for over 7 years, and I have had a list of dream guests for just as long - and Gary has had a firm place at the top of that list for all of those years. And now that dream has become a reality!

After you've listened to this episode, be sure to check out my bonus episode with my dear friend and previous colleague, Marissa Hofland, where we recount the magical story of synchronicity and practical steps of courage and audacity that led to Gary Vaynerchuk being a finale guest for my very first season of this podcast.

Now, without further ado,

Gary, welcome to leave room for the magic podcast. It is very surreal and fantastic to have you here today

[00:02:55] Gary: I'm thrilled to be doing it.

[00:02:57] Karlee: Likewise. Well, I cannot say thank you enough for saying yes to my audacious ask when I met you at the Shangri La in Toronto. You're a true hero of mine I've been following you for a long time and it's a pleasure to have you here.

[00:03:09] Gary: Happy to be here. Thank you so much. And this goes back to, you always have to ask. Like, us bumping into each other when I was having a business meeting in Toronto, you being in the hall working, running up to me.

I'm in an incredible place in my career where this is happening often, right? I'm so flattered, I'm humbled. And because I'm so flattered and humbled, I still want to leave room to do this in a world where, and I know that I'm five minutes late, so this will be 15 minutes, in a world where I'm still behind on like three of the biggest meetings I could have for 15 minutes, my admins always ask me, "Why are we doing this?"

And they're coming from a good place. And this is, I'm starting with this because I want everybody to hear this for five different reasons. It's because I loved the game of entrepreneurship and people building you're in a place now that I've been in and I know me being on here changes the course of this podcast.

I know in my mind, consciously, that you'll now be able to say that I've been on the show and you will book better guests and your journey is now different. That's humbling to me and I need to keep and everybody listening. If you're lucky enough to be further along in your journey, you need to keep having capacity to leave people deposits of good. This is a deposit of good.

And listen, for everybody who's listening, and there's been thousands of you that ran up to me and I said, "No." I'm sorry, I just don't want to promise or under deliver. Or even worse, I've said yes, but got lost in my inbox or when I changed admins they got lost. There's plenty of times I've said yes to something as audacious as your request and it didn't happen, and that sucks and I'm trying to get better at that.

But more often than not, I've learned how to be humbly real and say, "Hey, I just can't Karlee. I apologize, but good luck."

But I'm pumped that when I said yes to you that we're here now and I'm excited to do this and I hope people learn two things from that little mini story that we started with...

One always ask.

Many of you have seen me and you've been so sweet. You know how busy I am, so you haven't even asked. Let me decide if I can or can't.

You know, it's okay. If you ask nicely like you did . You asked nicely. And one out of every hundred times I say yes, and one out of every ten times that I say yes, it gets fully done because it doesn't get lost.

And then for everybody else who's lucky enough to be a little further along, keep giving back. I just put out a video of me buying a lemonade for twenty bucks, because I grew up doing lemonade, and somebody in 1985 stopped and gave me ten bucks, and I'll never forget it. Here I am as a 47 year old man, forty years later, telling you the story of a biker, I can literally see him driving down Tingley Lane, stopping and giving us ten bucks to fill up his lemonade, his bike bottle, and it changed my life, maybe. Maybe it got me even more happy or addicted to believing in my entrepreneurial journey. So, I know I'm talking a lot, but I want to tell that story because in the story of how we even got here, there's two massive layers and levers to pull.

One... Always ask nicely, and two... always give back to the game that got you there.

[00:06:03] Karlee: Wonderful. Well, thank you. My colleague who was sitting there with me that day, we've actually recorded the story of the synchronicity of running into you and stuff like that. It is going to be a bonus episode. So, I hope people tune in and listen to that, because it's a fun, magical one for me, and it's magical to have you today.

And actually, I'd love to start with that question, because one of the things that really struck me is that as somebody who's flying around, doing all these business meetings, running multiple companies - you are very present with everybody that you come across. I witnessed you interacting with a colleague of mine as we were leaving a conference. How do you develop, you know, how do you get prepared at the beginning of the day to develop that kind of presence that you can have that level of attention with people?

[00:06:46] Gary: I don't know if it's a beginning of the day thing. I think it's an every second of the day thing. Which is, you know, I'm aware that my communication style doesn't necessarily represent humility. I speak with heavy conviction, I'm competitive, I'm ambitious. These are all things that may allude if you're not paying close attention. And I don't expect anyone to pay close attention to me. Everyone's busy. They don't need to be worried about me.

But the hardest thing to see for everybody who consumes me on the internet is the humility.

Look, Julian and I, Julian is filming me right now, we were at the airport in Utah this weekend, actually, Saturday. We had a few minutes to talk in the airport. We were kind of talking about, he brought up a time when we had something wild happen, actually, and the way I handled it, I'm proud of.

It was a very weird situation, and I would say it was acceptable, if not expected, for me to handle it differently, and I handled it with grace, calmness, empathy for the person that made the massive mistake. And we have this nice moment, we're walking and Julian talked about some of his friends in his world who aren't into entrepreneurship and they don't really know me outside of, you know, I'm pretty omnipresent at this point, if you're into social media, you have seen me and, you know, they're surprised and intrigued by the things he says. He and others on my team, they know me because they see me behind the scenes.

You got to see a little bit of that by just happening to be out in the wild where I was like, in the wild, you know what I mean?

[00:08:16] Karlee: Yeah, absolutely.

[00:08:17] Gary: That was a micro moment, we were five seconds. You could have gotten a good version of someone. These people really know me, and I think the answer to your question is humility.

How/why am I present? Because I don't think I'm better than you when you and I interact.

[00:08:30] Karlee: Hmmm, I like that.

[00:08:32] Gary: You know, I understand why people want to interact with me. But that that even humbles me more. You know, and so I think humility is imperative. I think genuine curiosity. I'm curious. So I like meeting people. I know I like to know their story. And look, I think I have a genuine love for people, so it's easier for me to be present because I like the human on the other side.

I default into optimism. I don't approach people with cynicism. I don't think that they need to earn my trust. I give it to them on day one. I'm open hearted. I'm pure of heart. I'm full of love for my fellow humans until proven otherwise, and even when proven otherwise, I deploy compassion and sympathy for them trying to hurt or do wrong.

And so that emotional framework leads to being attentive and really locked in with people.

[00:09:25] Karlee: Well, I know you've talked a lot online about those are skill sets that your parents, and especially your mom, have given you over the time. Is that a muscle you've built over your lifetime, like between 18 and 47?

[00:09:36] Gary: Yeah, and I would say even earlier. I think a lot about high school. It's kind of crazy how I navigated high school. I was 4'11" my freshman year of high school, which {makes exasperated noise}. And I looked 11. So, now I'm 14, going into high school. I look 11-12 on a good day. I'm 4' 11". If you don't think senior guys picked out their easy target, and I think back to the first months of freshman year of high school recently and I was like man. And maybe this is happening because my daughter's gone into high school now and I'm seeing the same in her, I was just able to navigate it emotionally.

Like, no teasing, no making fun of, no bullying, no pushing, no physical or emotional or verbal conflict penetrated my self esteem. So, I was locked in fairly early, and then because of that, because I was good, now I had the capacity to bring good. So not only was I dealing with it, I was the one who was the hand around the shoulder for my fellow classmates who weren't able to deal with it.

So not only did I probably get picked on and razzed and beat up a little bit more than the rest of the gang because I was of the size and I'm also loud and who I am to begin with, so I was an easy target. I was able to first convert any of that negative energy to positive energy pretty quickly because even at 14 I had enough charisma to flip even the toughest bully that was a junior. But second, I was there for my homies, right? I was there for classmates I just met. Freshman year high school in 1990 in New Jersey was, put it this way, politically incorrect.

So, I think it's always been there, but it is a muscle that I've worked on day and day out, day in and day out. And I continue to work on it daily. I think I think being the bigger person is something I practice every day.

[00:11:33] Karlee: That's wonderful.

I'm going to shift gears here a little bit, Gary. One of the questions I had for you coming into this, you've talked online about your intuition being like the brain in your stomach, and I think a lot of business people talk about the tactical stuff, and people touch on the intuitive pieces of it. But if I think about, one of my questions for you is how do you navigate your gut intuition? Do you have practical tools and checks against that gut intuition?

[00:12:01] Gary: Of course, the results. But i'm not scared of losing. Why am I so good at intuition?Because I don't fear being wrong

See what's happening there? I love how you reacted. Got it?

There's two things going on. It's not that i'm more intuitive than everyone. It's that I'm willing to risk it on my intuition because if I'm wrong, two things happened, I lost and I learned and I get ridiculed or judged, but I don't care.

[00:12:33] Karlee: Right.

[00:12:35] Gary: And I don't care because I'm audacious. I don't care because I'm empathetic that one's judgment on my business decision if I failed is no different than me being frustrated with the New York Jets. They're allowed. They're allowed.

[00:12:48] Karlee: Yeah.

Is there a gap between you acting on your intuition? Or do you, do you typically at this stage just kind of flow with it? I guess, conversely, have you ever had a time where you went against your intuition and learned from that as well?

[00:13:02] Gary: Of course. You know, it's not very clear to me, you know, my brain moves pretty fast and I'm just trying to think of a quick, good example for you. But yeah, of course.

Normally when I'm being overly hopeful. I'm uncomfortably optimistic and I think I've had to become more and more practically optimistic through the years.

I'm very good at taking the stray dog home only to then get bit and have a disease. I always used to tell my girlfriends, girls that were my friends, that weren't my girlfriends, I used to always in college and high school and post college tell them, "Oh, thank God I'm not a girl. I would have only dated bad boys," because I love a good fixing. I would have found the most completely broken dude and try to fix him, you know what I mean? That cliché.

I've definitely done a poor job hiring through the years because I'm doing a form of charity more than I'm doing a form of business. These are things I've had to get better at.

[00:13:57] Karlee: Yeah. I've heard you talk about your superpower being empathy before. And I think a lot of empathetic people fall into that pattern of fixing and thinking they can do more with somebody, especially in a relationship sense than they can.

[00:14:09] Gary: A hundred percent. And that's okay too. Like I don't mind all those losses. I'd do it again. You gave somebody a try. You went for optimism. You went for love. You went for hope.

But, you know, there's consequences to making bad decisions. And I think I'm better at recognizing whom to make those jumps with. I think there's a level of humility that wasn't in that. I felt so over the top emotionally strong that there was probably a part of me that thought I could fix anyone and I think I'm learning like at what cost?

And now I look at it as to the cost of whom? One thing that's happening in my career is I'm now worried about the top 20% of my organization not getting the financial emotional and all the other value they can get from me and my companies because I'm spending too much time enabling and entitling the bottom 20%. And that's been a new reconciling that I have to do in my own body.

[00:15:06] Karlee: Yeah. Along similar lines to that, I know you've got this big life goal of owning the NY Jets. I mean, it's in your bio. I think there's a lot of talk about manifesting online, but this podcast tries to bridge the spiritual and the practical.

So, when you're trying to make decisions, if that's a big life goal of yours, how do you make short term decisions, to ensure you're staying on track towards that big goal?

[00:15:32] Gary: I mean, the big goal's complicated. I think a lot of times, if somebody doesn't know me, especially if they have let's say, maybe even a cynical view of like, "Ugh, another guy trying to be a billionaire and buy the Jets!"

But if you go to my Instagram, the first post I have pinned, goes very deep into why this has been with me since I was 7-8 years old.

[00:15:50] Karlee: And it's a good one.

[00:15:51] Gary: Yeah. And I think, honestly, even when you ask this question, probably the reason I just answered that is, I don't really focus on that.

I don't really focus if today was another stepping stone to buying the Jets. I focus on today is another day I'd like to be happy and deliver on my responsibilities. And I'm aware that I have this big goal in the background. I try to aim big and I try to do big things and I try to build, but I'm not crippled by the literal interpretation.

I think a lot of the theme of this talk is, I focus on the grey more than the black and white. And I think you've referenced it multiple times. It makes me feel, in different ways, tactics of this and that, so it makes me feel like you see me. I'm playing in the grey. You know, I'm playing in the grey.

And I think the grey is where the magic is.

The black and white is obvious. Like you said, I can literally go Google or YouTube how to blank, blank, blank and know how to do everything on Earth. Literally, for free. How to is nothing. I know how to get more muscles. Get in the gym, tear up my muscles, put fucking protein in it as much as possible, quickly after. But even though I want some more muscles and I'm starting to get a little bit of a chest because I'm doing more and more push ups, I don't do it, thus I don't have it. Right?

People know how to do things. I mean, almost everything people ask me in business they know how to do because they can Google it. They don't know how to get themselves to do it.

And that's why I'm so passionate about mindset and gratitude and empathy and patience. It's why I created VeeFriends to create these characters that embody - I want the world to fall in love with Patient Panda because then patience will be cooler. I want the world to fall in love with Resilient Red Devil because I think resilience is not being champion enough right now.

I think we're over coddling too much in certain situations, which is actually creating entitlement and insecurity. If you over coddle your children in the world, it will lead to entitlement and insecurity. And so you got to find the balance. Meanwhile, comforting and being there for people is amazing. So how do we find a balance?

[00:18:03] Karlee: Well, it's neat. It's been very cool to see your messaging and I'll direct people if they're not familiar with your messaging and everything, but thank you for championing self awareness and this great emotional spectrum that we all have and navigate.

And thank you so much for your time and being here today I really appreciate it. The magic is in the gray, you heard it from Gary Vaynerchuk.

[00:18:22] Gary: You're being very sweet because you're being dead on time and I'm going to be sweet and return and say something else.

Which is I hope for everybody that's listening - let me throw out a couple themes we didn't get to touch on but our kissing cousins of everything we just talked about.

Until you love yourself and really have self acceptance along with self awareness. Until that happens, you will not have nice days. You will have anxiety. You will have down days. You will struggle. Here's what's so fucked up and amazing about this - You get to decide. .

Life is gray. Life is... Beauty is in the eye of the beholder. Literally for everyone who's listening, and I can feel like somebody who's never heard of me right now, listening, crying. I can feel it. Karlee that's how intense, this is why I want to stay. Based on this momentum.

Until you love yourself. Nothing will happen. Good news, you're allowed to love yourself because you're the judge and the jury.

And you have to get out of blame to love yourself. You blaming your parents for shit is allowing you to have a package, a container, to continue to not love yourself. We must become more emotionally accountable. We are capable. We are capable to get free meditation. You are capable to get free exercise a.k.a. pushups in your room, walking on a hill. You are free to recognize that you're hanging around people that are negative, and you can start limiting that time, and you can go to the person that's most positive in your office and be like, "Hey Karlee, I want to be your friend. Can I take you out for lunch?" You are in control. Not everybody can afford therapy, but it's great for those that can.

Karlee, do you know that, most people would rather buy a Chanel bag or a Porsche to cover up their hurt instead of spend those dollars on therapy?

[00:20:23] Karlee: Yeah, but then it's so tied with self awareness because potentially they don't have the self awareness to realize that's what they're trying to numb, right?

[00:20:31] Gary: Well, what do you think? Correct. But what do you think I'm doing here? Ready? Very simple. This is a simple game. You don't have to be an emotional intelligence genius.

Are you happy more times when you wake up than you are not? The end.

You don't need to be. How often are you happy? I wake up happy 90% of the time, 8% indifferent and 2% anxious. That is off the charts numbers.

[00:20:56] Karlee: That is.

[00:20:58] Gary: I'm not even asking for people to do that. I got the luck of the draw. I did a lot of work. There's a lot that went into me being here at 47. My question is, where are you? Julian, what's your answer? Happy, indifferent, anxious not good. Go real talk. No bullshit.

[00:21:14] Julian: 75% happy, 20% indifferent, whatever the rest is.

[00:21:19] Gary: 5%. That's incredible. That makes me look at Julian and I know him enough to be like, "Fits in the pocket." How about you, Karlee? Real talk. No bullshit, vulnerable. Go with me.

[00:21:27] Karlee: Real talk, right now I'm 50/50. I'm on a bit of a rollercoaster and feeling in transition in a weird stage in my life.

[00:21:34] Gary: What you just did for everyone is everything. You have an audience that looks up to you. Likes you. Many of the people listening, whether you have 9 listeners or 900, look up to you, and for them to hear that 50% of the time that you wake up, you're meh.

For me, this is where, if we were best friends, you would be 80-90%, I'll tell you why. I would have convinced you, through the years of being together, or over one important dinner, not knowing where you were going is not bad. It's actually cool. Like, what? Nobody really knows where they're going. A tree may fall on my head today. I didn't know that would happen. Nobody knows.

Being comfortable with not knowing where the next turn of the rollercoaster is, that's...

I have nothing but headaches. I have a lot of bad things happen to me already. It's 3:24 PM. I mean real things. Gotta fire a partner in one business. Somebody sick, like personal stuff. I've had a rough day, by everyone's standards besides the 5% of people that are like me. It's okay.

[00:22:46] Karlee: Well, and I seen the reps you put in. I go back often. I'm 33 right now. And it's a very stark difference from my twenties where I feel like I knew the next step. If I was transitioning, I kind of knew what was coming next. And this has been an interesting one where I feel the transition, but I don't know what's next, and that's the leave room for the magic part.

[00:23:04] Gary: Were you a good student?

[00:23:06] Karlee: Yes.

[00:23:07] Gary: Makes all the sense in the world. Everything I just heard is, you knew the system, you knew how to get the A. There's a reason I got Fs. I don't give a fuck about the system, the system is the problem. You not knowing what's next is the best thing that happened to you.

It's time for you to let go and know that you're not in control at all.

[00:23:26] Karlee: Right. And it led me here today.

[00:23:31] Gary: You're literally not in control. Maybe this podcast is the changing moment of your career.

[00:23:38] Karlee: Yeah, maybe.

[00:23:39] Gary: You didn't, you didn't strategically decide to sit in that fucking restaurant hotel in Toronto? Promise it wasn't, I'm gonna sit here because GaryVee's in town and he's gonna walk through here.

[00:23:48] Karlee: No, I had no idea.

[00:23:50] Gary: Correct. That's life. That's real life. Cool. Love you. See you.

[00:23:55] Karlee: Thank you so much, Gary. Take care.

And that my loves, concludes our very first season of Leave Room for the Magic podcast. As you know, I love to end each episode with a story of synchronicity, so don't forget to tune into my bonus episode with Marissa Hofland, where we recount the ultimate story of synchronicity. Definitely of my year, if not my life, of how Gary Vaynerchuk came to be a guest on this episode.

Thank you so much for listening to this whole season. It has been such a pleasure to create this podcast and get the feedback from my audience and hear your stories of synchronicity. I absolutely love hearing stories of synchronicity and feel like the more that we share them, the more we see them in our lives.

So please continue to share on any of the social channels with me, or email us at info@themagicpodcast.ca. I would love to hear your stories of synchronicity and the happenstances that have come to be in your life. And until next time, and until next season, I hope you leave room for the magic, I hope you remember your magic and I hope you create some wild, incredible magical stories in your life.

Thank you so much for tuning in. We'll see you next time.