Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: Scooter Braun on Being Enough, Insecurity, Wealth, Investing, Fame, Marriage and so much more... About this episode From college party promoter to managing global stars to CEO and investor. Scott “Scooter” Braun is one of the most powerful people in media and one of the most multi-faceted entrepreneurs we have ever met. As the founder of media company SB Projects and the co-founder of TQ Ventures, he has backed prominent companies such as Pinterest, Spotify and Uber and managed some of the world’s biggest names in music including Justin Bieber, Ariana Grande, and Demi Lovato. Braun’s other accolades include founding Ithaca Ventures (acquired by HYBE for $1BN+) in 2021, and philanthropic efforts such as being a Make-A-Wish board member, raising $55M+ for Hurricane Harvey and Irma relief and continuing to instill the value of social good wherever possible. In Today’s Episode with Scooter Braun We Discuss: 1. From College Party Promoter to Managing The World's Biggest Superstars: What was the single most catalytic moment of Scooter’s career? What was Scooter's most painful professional mistake, and what did he learn from it? What was the decision-making behind Scooter's HYBE deal? What is the biggest challenge in scaling the trajectories of the people Scooter works with? If Scooter could change one thing about the music industry, what would it be? 2. College Party Promoter Turned Venture Investor: How did Scooter originally get into investing? How did Scooter’s party promoting business almost lead to an early investment in Facebook? Do people approach Scooter differently as an investor because of his success in the music industry? Why is vulnerability helpful for investing? 3. Scooter's Lessons on Success (And How to Deal With It): Why does Scooter believe happiness and success are not aligned? How does Scooter approach deal-making? Is work-life balance bullshit? Does Scooter think you have to break your back to become as successful as Jeff Bezos? Is Scooter scared of mediocrity? Why does Scooter think all entrepreneurs are bad at having faith? 4. The Secrets to Being a Better Parent, Child, and Partner: How does Scooter approach trust? How did having kids impact Scooter's mindset? Why was divorce the biggest catalyst in Scooter's entire life? Does Scooter worry that money will negatively influence how his children are brought up? What is the most important thing a child can hear from a parent? 5. Finding the "Scott" Buried Inside "Scooter": It's easy to become the brand you create. How does Scooter prevent losing himself when that happens? What does Scooter need to unlearn in the future? What has Scooter changed his mind on in the past 12 months? How does Scooter approach his relationship to regret? What single lesson you most would Scooter most want a young person listening to this conversation to take away?
Transcript 21,742 words · 2 speakers
Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Speaker 00 It's a piece of advice that my grandmother gave me a long time ago. And I've said it so many times, but I think this moment right now is the first time I truly understood it. She said, being mature is loving your 12 year old self. She goes, we get to about 12, we hit that teenage years. We're like, think we're not cool. We go through all these different things. We start to create that shell. And when you become mature, you actually realize you were always good enough at 12, before you started going through that teenage insecurity stuff.
0:26 Harry Stebbings? Today's episode is really a show unlike any other. I have to be honest, I was very, very nervous releasing this show. The truth is, I've always felt that I had to exude this image of of being strong, knowing all the answers. And in this episode, I'm just me, Harry. And it's thanks to my friend and guest Scooter Braun for making this show so special and creating that space where we could have this discussion. Scott or Scooter Braun is an investing and music industry mogul, has the founder of media company SB Projects and the co-founder of TQ Ventures. He's backed prominent companies such as Pinterest, Spotify and Uber. Scooter is also best known as the manager for some of the biggest names in music, including Justin Bieber, Ariana Grande and Demi Lovato.
1:07 Harry Stebbings? Braun's other accolades include founding Ithaca Ventures, which was acquired by Hybe for $1 billion plus in 2021. And I want to say a huge thank you to Dave Clark for making the intro to Scooter's stay, without which this episode would not have happened. But before we dive into the show today, are you building enough conviction to outpace other investors in this changing ecosystem? Tegus helps VCs get under the hood of their investments quicker, map evolving markets with deeper research, monitor the financial health of portfolio companies and even source new deals. Tegus is trusted by top firms like Redpoint and Spark Capital for everything from expert calls and transcripts to quickly surfacing insights across filings, comps and benchmarking.
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3:17 Harry Stebbings? You have now arrived at your destination. Scooter, I am so excited for this. So I sent out a tweet saying how desperate I was to have you on the show, and I believe quite a few people messaged you after it. So thank you so much.
3:30 Speaker 00 Look, thank you. You're very popular on Twitter. My favorite was, obviously I got calls from people that I do know, but my favorite was reading underneath your tweet all of these people saying, "Oh, I know them so well. I'll reach out to them." And I had no idea who some of these people were.
3:42 Harry Stebbings? They try and reach out to you.
3:44 Speaker 00 I have no idea. I've got a couple of calls coming in, and then I responded. And I'm really glad that I did, because we'll get into it. But the first time we spoke, you were just, "Hey, we can do this whenever. I'm excited." And then we ended up having a conversation on the phone where I pushed you on what you wanted to talk about and where I am in life. And I had a very vulnerable conversation with you about your life, mine, where you are, things you want to achieve, things you're thinking of. And I found you to be an incredibly thoughtful guy. Who is thinking about the right things at an age far before I ever did. And I told you before we started that part of the reason I'm here is one, because I was so impressed by you. But two, I can tell you're just going to be incredibly successful, but I think you're asking the right questions to be happy and successful.
4:27 Harry Stebbings? You say about being happy and successful, the biggest thing that I'm struggling with right now, honestly, is I always thought happiness and success were aligned and they're not at all. I'm sorry, it sounds arrogant, but I'm becoming more and more successful, but I'm not becoming happier. And that's a really hard dislocation because everything I ever believed is, they're not true.
4:46 Speaker 00 Look, I, it's funny because even as I got older, I thought that I solved this. And then you find out that you're always doing the work and you're always, the universe is always revealing to you what you need. I had a number that I wanted to make, I was like, I want to be a billionaire and then I found I'm making five grand is hard. I was nineteen years old and I started building the business that I have today. And I had a number, I met a guy who owned a Cadillac dealership in Atlanta, Georgia. And he told me a number that I could have his life if I made this much. And my goal was to make that much by the time I was fifty. And I was twenty seven years old and Justin's career had started to explode. And my accountant called me and another commission had come in. And I said, wait a second, how much money do I have? And I was twenty seven and I had surpassed my lifetime number.
5:28 Speaker 00 And I remember suddenly becoming thrilled and then within thirty seconds incredibly depressed. And it was because I realized that I thought if I got this much, I would feel at peace. And now I could just go through life and be happy and I, nothing had changed. So I found myself incredibly depressed and I ended up calling my dad. And I'm telling my dad now, I'm the most successful person in the family at twenty seven. And he's all excited and then I said, but I'm depressed. And he actually gave me beautiful advice. He goes, look, pull over, think about the times you're truly happy.
6:02 Speaker 00 And then call me back. So I pull over, I think about it, I call him back, I say, when I'm playing basketball with my friends, when I'm out for a great dinner with friends, when, you know, I'm seeing someone write me and I randomly help them out, or I'm at a grocery store and I pay for the person in front of me. And he goes, it sounds like being successful only allows you more time to implement those things. That's where your happiness lies. Success is not about happiness. And later on, someone said to me that financial success can either be a jail or freedom. And it's how you treat it. So I think the more successful you are, if you're willing to do the self-work with the liberty of not having to worry about a mortgage, with the liberty of having the time to put yourself first at times.
6:43 Speaker 00 You'll be far happier at an earlier age than I was, because even though I had that perspective, I then continued to build my life based on a narrative that I'd given myself of what it had to look like for me to love myself. And that's how I built, I don't want to be long-winded here, but I built Scooter. And it wasn't until thirty-nine years old that my personal life went into turmoil. And this narrative that I had built for myself of the success, the perfect marriage, the perfect life, this example to the world, suddenly it came crashing down and I was forced to do the self-work that made me understand that real happiness is being okay with, we talked about earlier, with your mess, being okay that your fact you're not okay.
7:26 Speaker 00 And I think that you're asking those questions and I think we're all on a process to figure that out.
7:31 Harry Stebbings? First question, when you called your dad and told him at that moment, what were you looking for? We were speaking before about my relationship with my father and I always seek his pride and satisfaction and approval. What did you want him to say when you called him to tell him about your number?
7:45 Speaker 00 Look, I think it's a lot easier at this perspective in my life to know what I was looking for. I've always wanted to be an example to other people. Right? And that seemed like a good thing because then I would give to charity and I would build a big business and I would have this perfect life and I would say to my dad, look how successful your son had become, even though he was a college dropout and you were so worried about him. And even though I did things differently, I had an idea of what I wanted to build, but it was always projecting outward. It was always, if I do this, and I see you smiling at me because I have a feeling you relate to this. If Harry Stebbings builds this VC firm, if Harry Stebbings builds this media company, if these help people, if he can be an example to other people of
8:28 Speaker 00 success, then he doesn't have to tell everyone the fear that he has, or the frustration he has, or the childhood that he had to step up to always be an example, because if he just sat there and didn't do anything, he never knew if that was okay.
8:42 Harry Stebbings? Do you know what I actually feel? I actually feel if I build them, then I'll be worthy.
8:46 Speaker 00 And that's the whole thing. It's you're projecting, look, it's the shame lie that I had and you have. It's what I see in you. I see a lot of me. We both have this thing that we're not enough. Who would ever love us if we just showed up as ourselves without the achievements? And that comes from childhood. It's why, you know, you asked me about the place Hoffman that I went to, and that was the first time since I was six years old that I liked my name Scott. And I realized I'd been building this mask scooter for all these years. And that place helped me realize that I'm okay being me and I'm still doing that work every single day. And I'm okay being a mess. And I told you the hardest part of getting to the other side of that work and then continuing it is so many people who knew that version that was filled
9:30 Speaker 00 with so much fear that built this beautiful thing. And I was proud. What I built as the mask of scooter was a beautiful thing. And we'll talk about a lot of that, I know. And I'm very proud of that. But you deserve to have both. You deserve to have the version of you that's tough out there, that's achieving and everything else. But you also deserve to have that inner child. You know, what were you called as a kid?
9:49 Harry Stebbings? What? Name? At school, Augustus. I was incredibly fat. And then at home, I was Haz. Haz.
9:55 Speaker 00 So my point is, does anyone call you Haz anymore? No, and it's an interesting thing because.
10:01 Harry Stebbings? But people, but this is what I also don't like with Soren. It sounds so awful and it's also very different. You're so much more successful than me, but it's just.
10:08 Speaker 00 A lot older than you.
10:09 Harry Stebbings? But like money and power changes your relationships. People are nervous of me like. My father and a lot of my friends, they're much more nervous because there's this hierarchy for them, not for me. I just wanna have a coffee with my mate Scott. They're like, I'm gonna come and ask for advice or ask for money. And it changes all the relationship dynamics you have.
10:27 Speaker 00 I told you this earlier, a therapist I work with really changed my life when she said, boundaries are there for you to teach other people how to treat you. And I was always really bad with boundaries because I thought that they showed weakness. I was like, I can handle anything. I don't have a boundary with anything. I can be completely open and no boundaries. And I realized that it is okay for me to have boundaries. And say to people, if you're gonna be in my life, you have to treat me a certain way. And that is seeing me for who I am. And there are certain people, it's been frustrating for me that because of rightfully so, the way I was before, they think that's who I am. But they're also not giving me the grace of that growth. And maybe they have boundaries in me because they don't know, when that's all fair. But I can tell you with what you're describing, you're giving that power.
11:11 Speaker 00 You know, that's, it's like Stoic philosophy. It's like you could, it's only your reaction is what matters. When you decide to be comfortable enough in yourself, truly comfortable enough in yourself and do that work, that you feel comfortable as has or hairy. Then you won't be affected by how they're coming in. You'll be able to look at them and say, hey, I need you to treat me this way. Or I'm sensing that I need to remove myself from this situation or completely unaffected and you're not giving it any power. It makes you uncomfortable because you're still trying to navigate. And I don't wanna tell you how you feel, okay? But I know for me in the past, I would try to navigate how to make them even feel comfortable so I could feel comfortable. I, I just think that I'm sound preaching to you, but it's only because I'm on that path right now.
11:56 Speaker 00 I'm just as much of a mess as you when you're talking about what you're going through. I'm still navigating. I'm still having that dark side rise up in me when I have certain insecurities and I wanna defend myself and say, well, actually, no, I'm this person or. And I think I'm working on getting to a place where I'm comfortable enough with myself that. I can just say, okay, if you're choosing to meet me and see me and love me, you get to stay here. And if not, I don't have any ill will, but I don't have to give my energy to that anymore.
12:24 Harry Stebbings? Can I say, who's there for you? We spoke earlier about, I'm there for a lot of people, a lot of people in the family in particular. And then booze was there for me, alcohol was there for me. And that was a crush and great, it worked. Who's there for you at the end of the day? Cause you're there for so many.
12:39 Speaker 00 My grandmother died a little over six years ago and she was there for me. I realized my grandmother died, eight days later, my second son was born and I was really depressed losing her. But I didn't tell anyone because I had to be there for my father. My mom was being there for my dad. I would, I'd always be the fixer, right? And then I had to jump in and have a child and I realized no one asked if I was okay. And I got very depressed again because no one asked. And my wife at the time, Yale, said something really beautiful to me. She goes, that's your fault. You don't share with people who you are. You're not vulnerable with people and telling them, so they don't know what to ask. What you're doing now, doing this podcast and being this vulnerable, there are a lot of people who want to be there for you.
13:20 Speaker 00 Strangers who I've checked your Twitter and I've seen the comments, like people really are falling in love with the vulnerability of what you share. I did. That's why I came because you spoke to me in a way that I was like, this is a really good guy searching for answers just like me. So when you ask who's there for me, since I've done this work, not only are there a lot of people there for me, but I also came to the realization that there were always a lot of people there for me. And I just wasn't letting them in because I thought that it was weak to do.
13:47 Harry Stebbings? How do you approach trust? This is the other thing that I find now, which is there's a lot of people who will be there for you, who will want to be there for you, your scooter. And you can't trust everyone.
13:57 Speaker 00 One, I have three beautiful kids that I get unconditional love from. I'm like Green Lantern with the lantern, getting powered up by my children every time around them. There's just something so beautiful about children. I coached two of my kids' basketball teams. I bring my daughter to dance class on Mondays and I love being around them. I'm obsessed with them. I don't want to become the dad that's overbearing, but I really.
14:17 Harry Stebbings? But let me tell you about my kids.
14:19 Speaker 00 No, but I just, I'm obsessed with them. Like it's, and it's because they love me. It's like, it's such unconditional love that it's hard to describe. So number one, I have that. Number two, I have a bunch of friends. I'm actually in town with my buddy David Appleton, who's been an amazing friend to me. I have. Two of my close friends since I was 11 years old, Mike and Vuk, who I was friends with my whole life since I was 11 and we'd hang. But when I went through this kind of transformation of pain to joy over the last three years, I have more Fati, I have tattooed on my arm, it's the Marcus Aurelius Meditations. I had the suffering and the joy and I learned to love them the same. And when I was vulnerable, me and these two guys who'd been in my life my whole life, took it to a different place.
15:01 Speaker 00 And they say, we've known you your whole life, but we didn't know you until now. And they check on me and I check on them and they are there for me in such a beautiful way. And I started to realize how many other people were. I just always thought that I had to show this strength to these people. And I was also playing into my trauma of trying to satisfy the people who were abusive to me. It's like negative comments on your Instagram. I'm paying so much attention to certain people in my life, who I'm trying to win over to make sure that they love me, that I'm not paying attention to the people standing right next to me, who truly love me and aren't asking me for anything.
15:36 Harry Stebbings? They hurt me. Do they hurt you?
15:38 Speaker 00 Yeah.
15:39 Harry Stebbings? I don't know if I'm allowed to ask this, and so the joys of what we do is we can edit. So when everything happened with the Taylor stuff, and it was such hate, did that hurt?
15:47 Speaker 00 Yes, yes. I always said, oh, I took the high road and everything else. I was going through stuff in my personal life. I really didn't have the bandwidth to deal with it. And it did hurt because the day before it happened, I had never had any negative news about me in our entire industry. I'd never had an issue with anybody. And then suddenly overnight, because someone said something, I was a bully. And what I realized though is I started to go out in public and say, I'm not going to be a hermit to this. And not one person has ever said anything negative to me in public. So I will tell you, the internet is not a real place. Dave Chappelle says that all the time. Twitter is not a real place. So if someone is taking time out of their day to write you something negative, and they don't even know you online, it's usually because they're hurting. It's not real.
16:29 Speaker 00 And the other thing I can tell you is if someone has over 100 million followers and 10,000 are yelling you at the same time, it seems extraordinarily loud, but it's less than 1%. It's not real. And I knew that from handling my own clients. I think the thing I took pride in that moment was that no one else said it. A lot of times when... Someone comes out and says, oh, this whole time this person's been this way. There's an onslaught of everyone coming out and being like, I agree. And no one did that. No one actually came out and said those things. And I have no ill will. I don't know if, you know, what was told on the other side. But I don't have any ill will. And I'm actually at a place now, to be honest, out of respect, I answered it for you. But I've moved on from it. And I don't even feel the need to talk about it anymore because it no longer needs to affect me. But the answer at the time, it hurt.
17:14 Speaker 00 But I also hadn't done the work that I ended up doing over those next three years. So I was so hurt because my narrative I had built was being the good guy. So then suddenly being labeled without any real facts, it was messing with me. And I look back now and I think that it had to happen. I think that had to happen. My divorce had to happen. I had to be knocked in the gut for me to go do the work. Cause there were all these signs for probably four or five years leading up to that, for me to go and do this self-work. And I kept telling myself, but I'm fine. I don't have any issues. God, universe, whatever you want to call it, gave me what I needed to humble me to a place to go do the work. Because you play a role in every conflict.
17:55 Speaker 00 So I can say, oh, I didn't do anything else, but everything, you had to play a role in something, or it was for you. Something was given to you. There's a great book, Many Lives, Many Masters. It's by Brian Weiss. It's, he's the head of psychology at University of Miami. And he wrote this book about a patient that came in who he was helping. And he had to do hypnotic regression to get to her early childhood. And he found some stuff. He goes, oh, that should solve it. She came in, nothing was solved. He did it again. She went to past lives. And he said, this can't be real. And then he realized with her educational background, she couldn't know certain things. And he wrote a book about how this experience and what happened to change this entire practice. And when I read the book, I found it really interesting because it's obviously about reincarnation. And I said, well, that's just a beautiful way to look at life.
18:38 Speaker 00 We're here, we're given lessons to learn to be better. We can learn them and progress, or we don't learn them and come back and try again. And you don't have to be afraid of death if you realize you're just in a cycle of learning. And then my dad was like, our religion doesn't believe in that. And then I realized Kabbalah was only taught to 40-year-old Jewish scholars of the Torah. So it wasn't shared until recently and all these mathematical formulas are now found that have been around for all these years. But the other thing it teaches is reincarnation, which means Christianity, the Muslim religion, we already know Buddhism, all the major religions to actually believe in reincarnation, we just didn't realize it.
19:13 Harry Stebbings? Do you run towards conflict? You said the word conflict. I run away from it. And we spoke about relationship with family. I'll pay for conflict to not be there.
19:20 Speaker 00 I think there's a difference between what I run towards now. I would not say I run towards conflict now. I think I run towards resistance. I think I used to run towards conflict because I had that feeling, like we talked about, I'm not enough. So if someone had an issue, I just ran towards it. I want to address it right away because I needed it to be okay. So I could continue feeling good about myself. And I think now I realize that don't need to do that. So what I run towards is the resistance I find within myself. If I find resistance in myself towards something, then I have something unresolved and I need to look inside myself on what is unresolved and get to that work. If I do that, someone can have a conflict, but if I feel indifferent, I'm not giving it any power so I can move on to what my work is.
20:04 Harry Stebbings? I do want to take a different tact here, but we've mentioned a couple of different aspects. You mentioned Justin earlier. And often the question is, oh, how did you get into the industry? I don't want to ask that at all. I find there's catalytic moments in careers where the spark ignites. And it may not be what people think it is, but when you think about a catalytic moment that really you felt, oh shit, it's working. And this is my break. And so like for me, it could be a specific episode or the fundraiser. Is there a moment where you're like, yeah, that was the moment?
20:32 Speaker 00 Look, I could tell you there are certain moments because I knew what they were. The weird part is when certain things happen to me, I get almost a blueprint gets downloaded in my head. And I can see everything like a chessboard, like I know exactly what's going to happen. So when I saw Justin, while everyone told me no, and everyone thought I was crazy, I knew exactly what to do and I saw the plan. I just knew. I was like, this kid's going to be the biggest artist in the world. I know exactly what to do to help him become that. Then there were moments, I don't know what it's going to be, but there was a moment where we had a mall that got overran. And I knew that, okay, the press is going to pick this up and I got arrested for it. And yeah, and because they, we wouldn't put up a tweet like, and they arrested us and for causing a riot, but we didn't. And caused the riot and then my record got expunged later.
21:15 Harry Stebbings? I'd love to see that on there.
21:17 Speaker 00 Oh, yeah, it's it was there was a whole free scooter.
21:19 Harry Stebbings? Facilitation of Justin Bieber concert.
21:21 Speaker 00 I know it was at a mall. He was just making an appearance in Long Island, but the next day on the national news, this crazy incident at the mall happened and suddenly he was a household name. Or we were putting up all these videos on YouTube and he sang With You by Chris Brown. And every that was the one that went to a million the first time and everyone binge watched like Netflix, all the others and everything started going to a million and he became one of the biggest things on YouTube. I've had those kind of moments with so many different careers. Many times like that riot where I got arrested, majority of the times those moments are the moments of tragedy. It's the moments that other people would say, oh, this is going to be a very bad thing. And how you choose to react can change everything. You can choose to walk into it and just put your head down and say, that's it.
22:06 Speaker 00 Or you can choose to react in a very different way that can lift and they say make lemonade out of lemons. And I've seen that so many different times that almost every single time something bad happens or you would assume it's a bad situation. I always say, okay, there's a there's something in this for us. There's a message in this, something that something special can happen here.
22:24 Harry Stebbings? Is that one that you think too with that?
22:26 Speaker 00 The most special thing I've ever been a part of was the Manchester concert. I have the Manchester Bee tattooed on my arm. Ariana, who I had dinner with last night, she knows this. I always tell her and she gets emotional, but she'll always be a hero to me. Cause she could have stayed home after that. She met those kids. She was there. She was traumatized. I asked her to do a concert two weeks later in response to terrorism. That's a very unfair ask. But I was angry and it was an unfair ask. And she said no at first and then two days later called me and says, I'm not who I say I am unless I do this, we need to do this. And all those artists showed up. But I always say that the hero was the city of Manchester. Because people forget the London terror attack was the night before that concert.
23:10 Speaker 00 And the British government put a full alert on saying you can go to the concert, but there is likely an attack. That is what the Greater Manchester Police put out as a bulletin. And I thought no one's going to show up. It's on BBC. It's being broadcast over Radio One. It's on Twitter. It's on YouTube and it's on Facebook. You can sit at home and watch this magnificent concert and be safe. And when Marcus Mumford took the stage to open it up for us, it was filled with sixty six thousand people. He and I talked beforehand and he called for a moment of silence. And it was just completely still and I just couldn't stop crying. And it was the most powerful thing I've ever been a part of that in March for our lives, which was in response to gun violence, which we're dealing with again, unfortunately,
23:55 Speaker 00 in the United States. But those kind of things, being a part of those, producing those with people that I love, I'll never forget those moments. It makes it all worth it. And it's why this country that I'm in and why Manchester always has a special place in my heart, because I've never seen bravery like that, ever.
24:11 Harry Stebbings? I think people get podcasts wrong and I think people get discussions wrong because they often focus on the theory too much and not the story. I think we both have a love of storytelling, but it's not tied to lessons. One of my biggest lessons was when I lost millions of dollars in Pakistan on investment. Many reasons why it was a mistake.
24:28 Speaker 00 That sounds like a hangover movie, like when you describe it. I lost millions of dollars in Pakistan.
24:33 Harry Stebbings? Literally millions.
24:34 Speaker 00 It just feels like Zach Galifianakis was there.
24:36 Harry Stebbings? We could have made the hangover movie of how much I lost in Pakistan. But I learned a lot. That was a really painful mistake for me professionally and I learned a lot. When you think about your most painful professional mistake, what would you say it was and what did you learn?
24:51 Speaker 00 My most painful professional mistake? I have lots of them, honestly, but I don't see them as mistakes. I see them as the greatest moments of perspective because I needed them. The way you just said was such a big mistake and I learned from it. If you didn't lose millions of dollars in Pakistan, I don't think you'd be exactly where you are today. You would have less learnings, you wouldn't have the perspective to go and do the great things you're going to do. I think those moments, like I said, it's for you because you need the perspective of those losses to actually understand how to win. And I have so many. When I sold the company to Hype, my entertainment company, that is, because we have obviously an investment firm that's separate. When we sold to Hype, it's hard doing these things sometimes because you have to talk about yourself.
25:32 Harry Stebbings? To my, I'm asking.
25:33 Speaker 00 So I gave $50 million of my own stock away to my employees and my artists when I received my payment. And the reason I did that is because I had learned from past deals that I took everyone who ever had equity, they got their stuff and we just kept moving. And what I realized is I wanted everyone to feel a part of it. And what I and everyone was, oh, it's so generous. But the learning wasn't the generosity. Because there's a hundred different ways to be generous. I could have given the money to charity. It was because I also realized there's a freedom in generosity. There's a way that we talked about earlier, money can trap you. You can make a lot of money and then you're bound to the responsibilities of what you've built, or you're bound to the expectations of what you've built, or you're bound to the frustrations of others of what you've built.
26:17 Speaker 00 And by doing that, I felt like, one, I took care of everyone. And two, if I choose to go in a different direction ever, I have the freedom of being able to look everyone in the eye and say, I did right by you. And that was important to me. And I learned that from not doing it fully in the past and thinking, well, as long as I'm just giving to charity, that's enough. And I look at other people I admire and I took it from them. And I think there's just a hundred different points. I don't want to go into them because they become headlines and I don't want this to necessarily go in that direction. But I can tell you that you can do everything right by the book. And people can say they're frustrated and you can say, I did everything right. But ambition can also hurt you. And what I mean by that is there are plenty of times in my career where I can look back and if someone's frustrated, I say, I didn't do anything wrong. I did everything by the book.
27:02 Speaker 00 This is business and I did everything right. But I knew in my heart I could have done it a different way. And I was too afraid to do it a different way sometimes because I didn't trust people. I didn't trust if I was completely transparent with them, would I get it done? And I look back now and I trust the universe a little bit more that it wanted me to be here, that it would have happened and I could have been more transparent. And the only bad thing that would have happened of being transparent is those who didn't help me get it done, I would have recognized who those people are and I would have removed them from my life. And maybe I wouldn't have gotten every single deal, but I would have got other deals. And I think that the lesson it taught me now is that I want to get to a place that when I win, everyone involved wins. If there are 10 people involved, all 10 win.
27:44 Speaker 00 I don't want to leave anyone out because I want a quality of life in my wins now.
27:49 Harry Stebbings? What was the decision making on the Hype deal? It was a big deal. It was a very momentous moment in your life and your employee's life. What was the thinking behind, yeah, we're gonna do this?
27:59 Speaker 00 Look, I think I was going through a very interesting time in my personal life. I was going through divorce. I was doing a tremendous amount of self-work. I had stepped away from my business somewhat for the first time in twenty years.
28:09 Harry Stebbings? I listened to your conversation with Jay and you had to burn a phone for a year.
28:13 Speaker 00 For about two and a half months, two and a half months. And then, but that was a big deal for a guy who literally always had his phone.
28:20 Harry Stebbings? Huge deal for anyone.
28:20 Speaker 00 And but I was like deep in the self-work and even when I got my phone back, I delegated in a different way and I wasn't hands-on. I lost a client in Kid Leroy for a while because he was like, I signed up for you and you weren't there. And then obviously I came back at a later point when I was on the other side of certain self-work and he's back with us now. I decided to do Hype because I wanted partners. My children were getting to an age that I wanted to take a different path. I wanted to do less management and more play of an executive role. I got approached by Chairman Bang, who's my partner now, and he became like a dear friend. We started doing Zooms every week privately. No one knew we were talking. And the day I was sold that I decided I want to do it, obviously he was offering us a really great deal. But the day I decided, he was talking to me and he said, in the West, you guys always talk about transaction.
29:05 Speaker 00 And in the East, we actually talk about what we're gonna do after the transaction. We don't talk about the transaction. We get that out of the way right away. And we just talk about how we're gonna build together. And that's why I don't necessarily like doing as much business with the West. He goes, but on these four phone calls we've had, these Zooms, you've never talked to me about the transaction. You've only talked to me about life, about business, about culture, about music, about family. And he said, I know that whatever happens, we will figure it out together on the other side. So I'm going to do this deal. And when he described it that way, I knew that was someone I wanted to be in business with. I had a great amount of admiration for him after that. And I felt like I can, not only do I have a partner that I can grow with, but I have a partner I can learn from.
29:46 Harry Stebbings? You said that about the transaction and how they don't focus on the transaction itself. It's ironic because so many people said you are one of the best deal makers when I did my research. And it's the antithesis of the transaction, actually. So what do you think about successful deal making?
30:00 Speaker 00 So my mom's dad died when she was eleven. When she was about eighteen, nineteen, my grandmother remarried. That was my grandma on the other side, not the one who died when my kid was six. And I had a grandfather who raised me as his own named Irving. And he started a department store in the Catskill Mountains called Sullivan's. And he was one of the most successful businessmen in that entire area of this like mountain towns. Right. And he was just this incredible entrepreneur of that community. And he realized I had a business mind very early on and I was the one in the family that did. And he told me before he passed my freshman year of college. And he said to me, the best deals are the ones where everybody wins. He goes, the greatest negotiations are the ones where everyone feels good about it.
30:41 Speaker 00 So when I've negotiated, I've been tough, but I've always tried to get it to a place where it's fair. I never wanted anyone looking and saying, I got a raw deal out of that. And I also learned that if I got the raw deal, I had to stand by it. If I made the deal, I stand by it. So if I said to someone, hey, we're going to do this and then we start working and they're not pulling their weight. But I gave my word, I'll stand by my word because keeping that is more important than actually proving, okay, this needs to change.
31:09 Harry Stebbings? How do you think about your relationship to regret? Often in deals you'll have regret and obviously among many different facets of life. How do you approach your own relationship to regret?
31:18 Speaker 00 I don't have as much regret anymore. I think I would, I'll find myself doing that, like I'll litigate the past sometimes. And then I'll catch myself and realize if everything hadn't happened, not only happened, but happened in the exact time it happened. Giving me the grace to get through it.
31:32 Harry Stebbings? Do you know what I worry about? There was an underlying question to that, to be totally honest with you.
31:36 Speaker 00 Okay.
31:36 Harry Stebbings? I'm fair of future regret, which is a weird one. Like I, I have the funds and the media company, Monday to Friday funds, media company, Saturday, Sunday. Done it since I was seventeen, now I'm twenty five and I will be doing it for the next ten years and I love it. And I fricking love doing everything about it. But when I'm forty five, A, I'm worried about being rich Uncle Harry to my brother's kids and being on my own in a big house. And I'm worried that I'll go, really? You're whole twenties, every single weekend you're in a dark room. Listening to yourself and I love it. Do you see what I mean?
32:08 Speaker 00 Yes, because I've lived it. So two things I'd say to you. Bezos started Amazon and you've seen this interview, I'm sure, where he says regret minimization format.
32:16 Harry Stebbings? Is one of the best.
32:17 Speaker 00 One of the best ever. And a couple of things about Jeff that I find interesting because I had the privilege of getting to know the person. Number one, I think you should watch that again because you have to weigh that. You have to look at that formula and you have to decide for you. Is it worth it me giving up my twenty twenties to have that freedom in my thirties and my forties and my fifties? And by the way, I decided it was. But then you're talking about a guy who also decided, okay, I need to do this because I'll regret not going this direction. And now he's also the guy who says entrepreneurs are incredibly misunderstood. Great entrepreneurs. And I think he's one of the most misunderstood people because here's someone, Jeff Bezos created more jobs in COVID than any human being on the planet. Jeff Bezos,
33:01 Speaker 00 when corporate companies wouldn't raise their minimum wage and it cost him a lot of money, raised minimum wage at Amazon to fifteen dollars when the US government was still at seven and a quarter, I think. And other corporate companies, because he did that, were forced to do the same. So people talk about charity. They talk about giving. He just donated ten billion dollars to the environment. What they don't talk about, it's easy for us to talk about nonprofit and foundations. But what we don't pay attention to is are we giving back within our for-profit businesses that actually pay the bills for these people? And I don't think that man gets enough credit for being someone who not only creates jobs, but makes sure people make a living, that they can survive and prosper when the actual government isn't willing to do that.
33:44 Speaker 00 And he deserves more credit. And I just don't think we like to glorify those things enough. But we used to glorify building a business to make it huge. And somewhere along the way, we got fined with small businesses, maybe some mid-sized businesses, but God forbid you become a behemoth.
33:59 Harry Stebbings? And it's gonna get worse.
34:00 Speaker 00 And it will get worse, but at the end of the day, people should pay attention to the fact that Amazon didn't need to do that. And that man did it because he thought it was the right thing to do while he was creating jobs. And I just think that deserves more credit and we should be celebrating entrepreneurs who do things like that because it makes a massive difference in the everyday man's life.
34:19 Harry Stebbings? I did just have to ask, I have this problem, we mentioned the regret minimization there. I have this problem with the work-life balance. I just think it's total bullshit. You speak to someone like Jeff in the early days of Amazon, most of the days of Amazon, I'm sure even now, you speak to your elons, they absolutely kill themselves to make what they are building as big and as successful as they've become. I don't buy the you can do it all, you can have the balance.
34:41 Speaker 00 So I'm actually gonna tell you, I asked the same question of Jeff. I actually asked him, how do you handle work-life balance? And he gave me the best answer I've ever heard.
34:50 Harry Stebbings? If you were actually a true venture investor, by the way, you would caveat that and just say, this was my answer.
34:55 Speaker 00 No, but I, it's, it came from him and he deserves the credit for it. I asked him, how do you handle work-life balance? And he said to me, I hate the word balance. He goes, why? And this is a man who has an amazing relationship with his children while building one of the biggest companies in the world. And he said to me, why should you have to balance two things that you love? You should harmonize them. And I said, really? And he goes, you should communicate to your friends and your children how much you love Amazon. He goes, my kids knew everything that was going on there, so they didn't feel left out. If my kid was going through something and I had to be there for my kid, everyone at work knew what was going on so that they understood that my kids come first. And you put them together, and I think that I, for so long, thought work-life balance was finding a way to balance them. So I didn't tell people on one side what was going on on the other because I thought I had to keep them separate.
35:40 Speaker 00 But I was passionate about both. That's like being married to two different people. And that's not fair, that's not gonna work. So I think that advice he gave me is something I now use in my life, that this next chapter for me, I wanna make sure that I harmonize it. If I'm passionate about something, I wanna make sure that everything in my life I'm passionate about is knowing about each other. The other thing is, the things I used to be passionate about, I'm not as passionate about anymore. So I have to also make sure that I don't stay in the same place and stay stagnant and become resentful of what I've created.
36:07 Harry Stebbings? You said about the next chapter there, I do want to discuss the investing. First, what was the first deal? And how did you get into venture investing before we touch on Tiki?
36:15 Speaker 00 I was a big college party promoter. And I used to pay a hacker to, every time I got kicked out of the EDU databases at the colleges, I'd pay this kid four or 500 bucks to log back in and hack back in and get me all the addresses so I could blast the kids. And then something called the Facebook.com launched and Emory was one of the first AIR12 schools. And I was like, wait a second, I can use this, the Facebook.com to get to all the kids. And I contacted Mark Zuckerberg. And then he put me in touch with the, at the time, it said, I think it was like Master of Coin Eduardo Savarin was like on the contact page. And he put me in touch with Eduardo and we started negotiating and I was trying to invest 100 grand for 10% of Facebook. And we had emails going back and forth.
36:58 Speaker 00 And then Eduardo wrote me at my SOSEDEF email address, because I was working at SOSEDEF at the time, hey, Mark wants to launch 32 more schools in two weeks. He's decided he doesn't want to take any capital. I found out years later, because I saw Eduardo in Singapore, that I had no chance of getting in because Eduardo was pushed out at that point. And then anyone negotiating with Eduardo, Mark wasn't going to let in. But also, he wasn't going to take any money because he was launching more schools. So I had broken up with my high school sweetheart. She was at BC. He was like, if you ever want to come up to Boston and still talk to us, come by. And I look back now and I know myself, if I would have gone up there, I might have have gotten in. But I didn't want to go up there because I was too afraid to see my ex-girlfriend. And I also didn't understand what it was going to be.
37:38 Harry Stebbings? That was a very expensive relationship.
37:39 Speaker 00 Yeah, but you know what? I didn't understand investing at that point. No one, these things didn't exist. I just thought it was a way to get my parties out there. So a year later, Peter Thiel invested, I think, a million dollars for 10%. And I thought, oh, my God, I could have made a million dollars. That's how much I didn't understand what it could be. So it's not like I understood, but in the years to come, Facebook kept rising and I recognized that. And I thought, oh, I did miss out on something here. I should continue to look in this space. And that loss opened me up to the idea of investing. And it led me to a slew of other companies that I've been fortunate enough to be an investor in. And I started investing very early. I think I started investing when I was twenty six, twenty seven.
38:18 Harry Stebbings? Do you remember your first deal? I remember getting sent the wire instructions, you know, fifty K to random bank, you know, wow, shit.
38:24 Speaker 00 It was, I remember one of my first deals, everyone thought I was crazy on my team. Cause I had a new business manager, I was starting to make some money. And it was a company that was valued at four hundred million dollars in San Francisco. And it was only in San Francisco and it was a cab company called Uber. And that was Uber Car. And the only reason I knew about it is I'd gone up there to see another tech founder. My team was like, this is crazy, you shouldn't do this. And I'm very grateful that I did. Travis is one of the best founders I've ever met my entire life.
38:50 Harry Stebbings? Was it immediately obvious?
38:51 Speaker 00 Once you met him, yeah. We all like to say it's so obvious what it's gonna become.
38:54 Harry Stebbings? No, but his talent and.
38:56 Speaker 00 Yeah, but at that time, like you were thinking, oh, it could be a two or three X, like, maybe. I don't wanna lie. I think we all say, oh, I saw it all the way. I saw my business all the way. The stuff I was investing in, I was betting on people that reminded me of another entrepreneurial spirit. So I always bet on entrepreneurs. Even now, Zee, who runs Row, Row, you know, Roman.
39:14 Harry Stebbings? I'm not, yeah, we're pen pals. We've never met in person, but we.
39:17 Speaker 00 Let me tell you something. You meet this guy and you believe in that company instantly. There are certain founders that you meet that you go, they're gonna figure it out one way or another. And I've been fortunate to be around certain guys. We're both friends with Daniel Ek. Daniel and I became friends. I invested in Spotify a long time ago. I've never sold a share. I'm a full believer. Obviously, I know that industry much better because it's my own. But I've been fortunate enough to be part of so many different rides. Now, building a fund with some friends. Howard Marks, someone I look up to. He wrote a really great memo where he talks about luck. And I agree with it wholeheartedly. I was born in nineteen eighty one in New York City. And I look the way I look. I won the lottery the day I was born with privilege. So for anyone to say they're not lucky in doing this, completely absurd.
39:56 Harry Stebbings? Yeah, I was such a nerd at school. I went to boarding school and I used to have those camping torches on at night because you had lights out. And then I'd have his memos printed out with a camping torch on my head. And I'd read them at night. No wonder I didn't have many friends. I was like fourteen.
40:11 Speaker 00 You're my friend. I think you're a very interesting guy. I think you're asking all the right questions. Ones I wish I asked at your age.
40:17 Harry Stebbings? That's very kind. Incredible kind of first exposure there. Talk to me about TQ, status, where that's at. Tell me about that.
40:25 Speaker 00 Yeah, I feel extremely fortunate to be a partner in this fund. My partners Andrew and Schuster, Andrew and I were friends. He introduced me to Schuster. We decided, hey, let's do this as a small consumer fund. We did incredibly well. And then we decided, wait, we're getting all these opportunities to be something beyond consumer. We got into all these other spaces, primarily tech and SaaS companies and just gaming companies and just really interesting stuff. We started about five, six years ago. We have over a billion in man, under management. We just closed our third fund. And we were very fortunate because we have, our third fund is a $500 million fund and we've only deployed, I think, 12%. So we're in a really good position in today's climate. And the thing I love about those guys is they run that fund full time.
41:06 Speaker 00 They're brilliant guys. And the thing I like about them is when they get in there with founders, they're not just guys who like, okay, we're going to back you some money. They actually understand how to be there with founders and help them pivot in those tough times. And I think that's what you look for. And I take a lot of pride that when founders meet me, who I haven't met, who are in our fund, they always tell me what a pleasure it is to work with those guys and how hands on they are and how much they back them. And we've been very stealthed about how we've moved, but I'm very honored to be in business with those guys and it's been a lot of fun.
41:35 Harry Stebbings? Can I ask a bit of a weird one? I had Ashton Kutcher on the show about a year ago or so. And he said, the hard thing about actually being an investor for me is people feel they know me coming into the meeting. And they're actually more nervous than they would be with other VCs. And so they don't show their best self. They don't present in the best way. They try and impress. And it distorts the actual investment decision-making process where for other people, it's like you have a raw, much more neutralized view. And for me, it's very difficult because they bring that predisposed knowledge of me.
42:04 Speaker 00 Here's what I'll say to that. Love him. Ashton and my son Levi and Ashton's son Bear are best friends. They were born in the hospital six hours apart. We actually ran into each other in the hall. We have a picture of our kids in a basket together when they were just 12 hours old and they go to school together and they're best friends to this day. He is incredible. incredibly charismatic and he is kind and he is genuine and he is smart. So while they might come in nervous because they're in front of the superstar Ashton Kutcher. I argue that he is so down to earth and good at what he does. That he can fix that very quickly and bring the best out of people because he brings the best out of his friends. I'm sure he can bring the best out of founders. That being said, yes, I walk into certain rooms where my career might be known.
42:46 Speaker 00 It might not. I find the same thing. It's whether sometimes I'll be in front of a musician who's very nervous or. Your guy who did the cameras before we started, he told me about his friend and we FaceTimed his friend and I noticed when he was dialing his friend, his hands were shaking. And I've been doing this long enough that I can tell someone, I take a shit on the toilet, just like you. Let me give you a hug. You know how to diffuse the situation. Because sometimes people are nervous, sometimes they're not. Sometimes they have a preconceived notion of who you are. Sometimes it's good, sometimes it's bad. I think it's your job to show up in the moment, be present and present who you are and help someone do the same.
43:17 Harry Stebbings? That's also why I think it is helpful to be vulnerable and vulnerability can be used in a positive, which is I'll often start. I always say being an interviewer and being an investor are very similar in the way that you have three to five minutes at the beginning. Where you can actually create an environment of safety and say, you know what, Scooter, I'm really struggling with my eating disorder right now and it just doesn't feel great actually about myself. Oh, I'm sorry to hear that. And suddenly the conversation is very different from, hey, how's the business going?
43:41 Speaker 00 I like you a lot because I'm hearing certain things you say. And certain questions you've asked me both on camera and off camera, and I'm thinking of my own journey. I think you are very. Intuitive about other people and I think that you can use vulnerability as a strength to what you just said, get other people to open up. I'm gonna ask a question of you. Are you really vulnerable? Are you vulnerable in a safe way for you? That you're using it as a strength, you're choosing the things you're comfortable sharing. That come across vulnerable to make people feel comfortable to open up themselves. But I'm gonna ask you an honest question of yourself. Are you really vulnerable with the things that really scare you? Or do you only share them once you've come to terms with them?
44:19 Harry Stebbings? The honest truth is it's hard when you have a boss. You can use vulnerability as a positive tool efficiently, and I think I've learned it very well. If I'm just being very honest. The hard thing is I have a boss and my bosses are my LPs, the investors in my fund. My bosses are their bosses and you very much feel that. I feel that for sure. And why most often the best interviews are people with no bosses because you're completely uninhibited. Am I totally vulnerable? Probably there's 10% that's not. And what is one of my biggest fears? I have fears of Macaulay Culkin.
44:49 Speaker 00 Do you remember Macaulay Culkin?
44:50 Harry Stebbings? Yeah.
44:51 Speaker 00 Home Alone.
44:52 Harry Stebbings? With respect to him, I'm sure he's doing something, but people go, oh, where is he now? And that's my biggest fear though, which is.
44:59 Speaker 00 You know, I saw some interviews with him recently. My argument is he seems to be very happy.
45:03 Harry Stebbings? I didn't want to pick on him, but do you know what?
45:04 Speaker 00 No, but I'm actually glad you did bring it up because from what I've seen, he seems to be a happy person and a self-aware person. And I don't know him, I can't speak to that, but I can tell you there's a lot of people who are known, who I can't say that about. And my other argument to you is, do you really have a boss? Or are you putting that expectation on yourself that they wouldn't support you if you told them the truth of your fears?
45:27 Harry Stebbings? I think I also don't feel financially safe enough. I think the honest truth is.
45:30 Speaker 00 But that's what I'm saying. It's not, let me rephrase that.
45:32 Harry Stebbings? Hmm.
45:33 Speaker 00 Because you don't feel financially safe enough, you don't trust them to support you if you were completely honest with your fears.
45:40 Harry Stebbings? Yeah.
45:41 Speaker 00 And that's what I'm trying to say to you, that I get that completely and I still work through that. I'm not a pro at that yet. My fears and insecurities come if I, if I share this or I don't know the answer. And if I'm not defensive in this moment, I completely get that.
45:53 Harry Stebbings? Do you not worry with your talents, say, and that may be awful phrasing with the people that you work with?
45:58 Speaker 00 Correct.
45:58 Harry Stebbings? That if you are too vulnerable, they'll be like, God, jeez, I'm listening, I'm listening.
46:01 Speaker 00 By the way, I have LPs and TQ.
46:03 Harry Stebbings? You have LPs and TQ?
46:04 Speaker 00 I have LPs and TQ, I have clients who work for me. I'm on the board of Hive, I'm one of the largest shareholders, but I have, we're a publicly traded company with a market cap that was at 14 billion. Between eight billion and 14 billion, depending on where the market is. And I'm the CEO of this company and I have bosses.
46:19 Harry Stebbings? And you don't worry?
46:21 Speaker 00 No, not anymore. What, it's funny, the things I worry about aren't them. It's when the worry comes in, it's my own shame. I'm now realizing the worry isn't their expectation because at the end of the day, I'm on my journey there, on their journey. I start to put this fear that if I present myself a certain way, if I'm not defensive, if I'm not doing the right thing at the right time. You know, who's going to support me? And I think what we're all working towards is getting to a place where we choose ourselves enough. I think there's a big lie. I want to say this because I don't want to come across selfish. When I say choose ourselves, this was the lie that was told to me. And it wasn't like on purpose. I think all our parents and people in our lives do the best thing you can. Every kid interprets life a different way. But the lie that came to me was, one, that I wasn't enough, and two, that if I chose myself, that I was being selfish.
47:05 Speaker 00 And now I realize that when I'm actually choosing myself, that's when my friends love me the most. Because I'm not a selfish person. I'm fun and generous, and so are you. I could already see it. Like, most people are. That when they're actually truly themselves and truly happy, everyone around them wants to be near them even more. And your LPs would want to be here more because they'd want to figure out, how did you get to that place? Because you're obviously a smart guy. You're going to get to the deals. Your vulnerability is what's getting you to so many people, and that's why they're investing in you. It's not that they are scaring you. It's that you don't trust them to see you fully. Because I don't know, and I'm only saying this because I deal with this myself. It's because maybe we don't trust them to see us fully because we haven't accepted ourselves fully.
47:47 Harry Stebbings? Sure.
47:47 Speaker 00 And we use an excuse by saying, oh, it's them, but it's truly us not truly loving ourselves or trusting ourselves enough.
47:53 Harry Stebbings? It took me years to get up drinking because I said, I look at my biggest deals is because I went drinking with them and I went drinking with them. And I used it as this crutch to keep on going for myself. And actually, it wasn't that at all. Do you know what I mean?
48:03 Speaker 00 Well, can I ask you a question?
48:04 Harry Stebbings? Yeah.
48:05 Speaker 00 We're going to flip the podcast a little bit. Five years from now.
48:08 Harry Stebbings? Yeah.
48:09 Speaker 00 Your LPs can't be mad about what you say. There, I know some of your LPs, some of your biggest ones. These are good people, really good people. They're not betting on it with 23, 24.
48:19 Harry Stebbings? When I started.
48:20 Speaker 00 How old are you now?
48:20 Harry Stebbings? 25.
48:21 Speaker 00 Okay, 25. They're not betting on a 25-year-old guy just because he's smart. They're betting on you because they want to see you win, because there's a lot of smart people much older than you that they get a return on capital. They're betting on you because they like you and they want to see you win. That's the truth. That's the part you're missing. They're betting on you because of who you are, not necessarily what you've achieved. Because there's a lot of other people who are much more seasoned that can give the same amount of money to. Five years from now, if you didn't have that burden that you actually are putting on yourself of thinking that you're not enough, or if I told the truth, what do you want your life to look like? If you didn't have to answer to anyone.
48:53 Harry Stebbings? Personal or professional?
48:55 Speaker 00 Both. Harmonize.
48:56 Harry Stebbings? I love what I do. I love this. This is what gives me huge, huge joy. And kind of speaking of the harmonization, I believe that one of the next great firms will be built with media at the very center of it and leverage media to find, to pick, to help the best companies in the world. And I want to build that. I don't view them as one or the other. The biggest question that everyone asks me is how do you split your time between venture and media? It's the same thing. It is the same thing. And I love that. And I want to keep doing that. And I want to keep having conversations like this where I am uninhibited and we've got this schedule which I'm really, I'll still stay into it all.
49:32 Speaker 00 We'll go to it all and then you decide what you want to keep.
49:34 Harry Stebbings? Sure, but I love that. And then I think there's the recognition at the same time that I really love kids. And I'm desperately alone, bluntly, and you turn off the lights at night and you're suddenly, the silence is very loud. Do you know what I mean?
49:48 Speaker 00 Are you nervous that if you sought that out or took time to have kids, that you're gonna, that right now is your time to build this?
49:55 Harry Stebbings? Yeah, yeah. I definitely feel the momentum is transient. I don't know if you see this, but it's like.
50:00 Speaker 00 No, I think, I look, we all feel that in all the great entrepreneurs.
50:03 Harry Stebbings? Hitting.
50:03 Speaker 00 I think what I always find funny, I do not want to preach to you in this moment. Because I think when I was coming up, all these great entrepreneurs would see me and they'd say all these things that they wish they did differently. And I'd say, you have the freedom to tell me this now because you were a fucking animal coming up, making the same sacrifices I'm making. So I understand your sacrifice right now and I appreciate it. And I think you're in an age where you can make that sacrifice and really dedicate yourself to building something. Because I think that's what it takes. So I do appreciate that. What I will tell you is you never know what's going to show up for you. And the one mistake I have seen people make is that they turned away really good things for their personal life. Because one, like me, I I always thought it would be there, or they thought I don't deserve this right now because I haven't achieved enough to have it.
50:46 Speaker 00 And if you find someone who really loves you, they're not going to care about what you achieve. They're going to love you for your essence. They're going to be happy to take that ride with you. And I think if it shows up, just pay attention to that. I think that I, for far too long, even when I found love and had children, it wasn't until recently that I became present. I think that I was so afraid of tomorrow being taken away. You talked about the fear of the future. I was so desperately afraid, and I think it had a lot to do with Holocaust trauma, being told the stories of our life was okay. And then one day they came and took it all away. And I grew up with those stories. And I think that trauma was in me, and I just thought, well, I'm building this and it's significant. And people are saying, good job, it's going to get taken away. I gotta keep building it bigger and bigger and bigger.
51:27 Speaker 00 And I was so afraid of it being broken tomorrow that I wasn't paying attention to what I had right now.
51:33 Harry Stebbings? And it's this hard balancing between the ambition and ferocity required to build with the appreciation of what you have today.
51:40 Speaker 00 I agree, but you know what? I had all the warning signs to make me pay attention. I didn't. And then one day, sometimes you gotta step on the rake and get in the face for you to pay attention. That's what happened to me. And I know that my life is going to be wonderful moving forward, and I had to go through transitional years of pain. But the other thing I realized as I read books and talked to really impressive people, everyone's had these transitional years of pain.
52:00 Harry Stebbings? Are you not fearful of mediocrity? I'm almost like, I don't want to go into a relationship. I don't want to have kids because I'm like, without, I'll be mediocre like everyone else. These losers who go to the park on Saturday and have lunch with family on Sunday.
52:12 Speaker 00 Can I ask you a question? When you were growing up, did you have a family member that you really looked up to? Did you have anyone you looked up to?
52:18 Harry Stebbings? Yeah, I'm British. Richard Branson was like the entrepreneur that I looked up to massively. I remember like Virgin Cola.
52:26 Speaker 00 Pretty, pretty a great dad, Richard Branson.
52:28 Harry Stebbings? Yeah.
52:29 Speaker 00 Yeah, kids love him a lot.
52:31 Harry Stebbings? Yeah.
52:31 Speaker 00 Spends a lot of time with them and his grandchildren.
52:33 Harry Stebbings? He does.
52:34 Speaker 00 Doesn't seem mediocre to me. Not a mediocre guy. Here's what I'd also tell you. You were paying attention to Richard Branson because of all the achievements. I would argue that you walk down the street and you talk to people about who their heroes are. They're not going to be naming Richard Branson every single time. A lot of them are going to say my grandma. This person, that person. My grandmother was one of my heroes. She worked in a sweatshop in New York City, the majority of my dad's life. And that was someone that most people would just walk by and not pay attention to. But she was a hero for me. I know exactly what you're saying because I did the same exact thing. I got to meet some of my heroes and some of them are great and some of them weren't. And I still want to achieve a lot of things in my life because I feel like I'm capable. But at the same time, I would argue with you, there's nothing mediocre about being someone that's loved. There's nothing mediocre about that.
53:16 Speaker 00 We see Fortune 100 CEOs jump off of buildings all the time. We say, what a tragedy, but we're not surprised. Have you ever heard of someone who worked at a soup kitchen killing themselves? And if you did, you'd be the most shocked person in the world because it just doesn't make sense. And we glorify these things because I've been there. It's like you grow up and you think if I achieve. You almost like the pain though. It's like while they're having fun, I'm grinding. Yeah, you're also grinding and you're feeling it. And it's like being in the gym or like playing in a great basketball game for me. It's like there's a grind and there's an achievement, there's a sense of achievement. That's beautiful. But don't lose sight of the fact that when we started this conversation was the first advice I was given, which is name those things that make you happiest. And you're going to realize most of those things, you don't need billions of dollars. Most of those things you could do right now. Go for a walk in the park with mum. You love that. Yeah, and a white chocolate cookie.
54:01 Speaker 00 Okay, that doesn't seem like you need to achieve a lot, but I think the achievements, they need to be for you at one point. I know what it's like, at least in my younger years, and still at times now, I'll admit the insecurities still come up and you find yourself doing it again. But you find yourself wanting to win because you think if you win this time, then everyone will see you. And then everyone will appreciate you and then you'll be there. There's a great Jim Carrey moment at the Golden Globes. Where they call him up and they said, two-time Golden Globe winner Jim Carrey. And he goes, I go to sleep, two-time Golden Globe winner Jim Carrey. And he goes, and when I go to sleep, I dream that sweet dream of being three-time Golden Globe winner. Because then it will be enough. And look, I don't think achieving things should ever be belittled. I think that's beautiful. It's why we love movies like Rudy and all these great.
54:45 Speaker 00 Sports movies, it's a football movie. You probably didn't watch that one because you're British. But we love movies with an arc. There needs to be some pain. There needs to be some triumph. Because that's a beautiful story. It's a hero's journey. It took me thirty nine years to put something into practice that I wish I started when I was twenty. And if there's anything I could say on this podcast, if someone's listening right now, that I could say, do one thing. It is what I'm going to say next. Once a year, take a week off, no phone, no emails, and do a week of self-work. Once a year, one week.
55:13 Harry Stebbings? What does self-work look like? Do I take a book and just?
55:16 Speaker 00 Listen.
55:17 Harry Stebbings? Sorry, I'm just doubling down. That's terrible interview technique. I haven't done a holiday in seven years and people are like, oh, hustle culture. It's not hustle culture. It's just because I started when I was seventeen, Scooter. And when you go away with no phone and no distractions, you have nothing but yourself. And I'm deeply uncomfortable because you suddenly then stare in the abyss and you're like, fuck.
55:39 Speaker 00 So you're right. You're talking to someone who lived your life. I started when I was eighteen. And I ended up having a tremendous amount of success and I thought I was someone named Scooter. And I forgot that my name was Scott. And I left that kid behind a long time ago because I was uncomfortable being Scott. And I didn't want to look into the abyss and deal with myself. So building and continuing and getting the praise of achievements allowed me to avoid having to do something which was as simple as doing self-work. And it wasn't until my life got to a place where I was miserable that I was forced to do the self-work and the transition started. And that's why I say if there's anything to listen to, I just don't want anyone to get to the place of pain I had to go to start.
56:23 Speaker 00 I'm offering it so you don't have to deal with what I dealt with because I wouldn't wish the pain that I felt in that moment on anyone. But I had to get to that low moment for me to start going in that direction. And when I say my self-work, for me, the first time I did it was Hoffman. It was the Hoffman process, no phone, no email, a week of intense self-work.
56:42 Harry Stebbings? When that moment hit, did you know that was the catalytic moment?
56:45 Speaker 00 There was no option. When you hit that level of bottom in a depression, you realize there's do something and the other option is not an option. That's not who I am. That's I realize like that isn't me. That thought that came to my head, way too dark, that isn't me. I'm not going to go in that direction. I have to do something. It was funny because my friend was like, I was like, what do I do? It's the same thing you asked. And he was like, start with this place Hoffman. You should go there. I did it. Changed my life. And he put me on the phone with this woman, Liza, and she started talking. She goes, I can get you in three weeks. And it was October 24th, 2020. And October 24th, 2020 was the release date of Ariana Grande's album.
57:22 Harry Stebbings? Oh, no.
57:23 Speaker 00 And I thought, this is the biggest album release I have of the year. And I remember being in a parking lot of her music video, hearing that over the phone, hanging up, looking up at the sky, and started hysterically laughing because I realized I was being given a choice. Choose the path that I've been on of success that had me hitting that rock bottom moment, or do something new and different. And I went into Ariana's trailer. I said, I need to do something. I will help set everything up. Everything will be lined up for your release week, but I'm going to be gone and I won't have phone or email and I'm your manager. And she talked me about why, and she's, you were there for me during Manchester. It's time for me to be there for you. I left and it was the first time I turned my phone off in 20 years.
58:04 Harry Stebbings? Were you scared to tell her that? Sorry, I didn't mean to interrupt.
58:07 Speaker 00 I was at a place where I was just like, it's time. I made that choice. I chose me for the first time. I need to do this.
58:13 Harry Stebbings? And you weren't fearful that she'd go, what?
58:14 Speaker 00 I was, but I didn't have a choice. It was choose that path or not. And I went and I thought my phone would be off for a week. And as my phone stayed off for two and a half months. And it put me on a very different path. And I'm incredibly grateful, like I really am. And I think when you say, what do you do? There are many people around you doing it. You just don't know because you've never asked. So I did this thing at Hoffman. Then I did a thing at Sedona where I studied breathwork. Then I did other meditation retreat the following year. That one week, I remember when I went in, I was like, what could a week do? But I had never slowed down for a week before. I didn't know what a week could do because I'd never stood in the abyss for a week. And when I did, I was shocked with what one week of choosing yourself can do for your wellbeing.
58:57 Speaker 00 And now I make sure every year I take that week.
59:00 Harry Stebbings? What are you doing that week now?
59:01 Speaker 00 I'm working on something. So if it doesn't happen, I'm going to choose something else. I'm thinking of this year of doing a silent retreat. Or I'm really intrigued by Wim Hof. I might want to do Wim Hof for a week.
59:12 Harry Stebbings? I I love Wim Hof, so I totally get you. I do want to ask before we move on to a quick fight, children are so important. Being a father is such a crucial part of your life. How did having kids impact your mindset?
59:24 Speaker 00 I always thought having kids would slow me down. I was like, oh, I can kick guys asses who have kids, they gotta go home, everything.
59:30 Harry Stebbings? That's how I think now.
59:31 Speaker 00 What you realize when you have kids is how incredibly efficient you become. Without kids, your brain just finds ways to get busy and things that you were like, oh, I have to deal with this. When you have kids, you're like, no, I have to get home. You sift through bullshit so much faster. And those kids are the best thing that ever happened to me.
59:48 Harry Stebbings? Did it change your work mode?
59:50 Speaker 00 Yes, completely. And even more so in divorce. Because I was a really good dad when I was married. I came home every night to put them to sleep. I adored them, but I wasn't fully present because I took it for granted. Because I would come home and I'd think, okay, they're still gonna be here tomorrow. So if I gotta take this phone call, I gotta take this phone call. If I gotta do this email, I do this email. If I gotta go do this, I'm here. So that's what matters. They see me. And when I got divorced, and it was fifty fifty, then it went to, you know what, they're gonna be with me on Monday and Tuesday, and then Wednesday and Thursday, they're five minutes down the road, and they're not with me. When that happened, I didn't take it for granted anymore. And I actually can tell you, they get a hundred percent of me in that fifty percent. And I think that's actually better than it was before. And no one tells you that, because I didn't have any divorce in my family, so I didn't know what to expect. I felt like such a failure.
1:00:34 Speaker 00 But the relationship that I have with my children now, on the other side of it, I'm so much more grateful. Because if I would have come to this awareness when they were eighteen, I would have deeply regretted it. And being able to have that happen when they're young, when my daughter's four, my my son's eight now, my other son's six, I'm really, while it's incredibly tough, and anyone who goes through divorce will tell you, you wouldn't wish it on your worst enemy, I'm very grateful for the relationship I have with my children.
1:00:58 Harry Stebbings? How did divorce change your mindset? If that's with kids, how did divorce change?
1:01:01 Speaker 00 You asked me earlier, what was the biggest catalyst in my life, business-wise, but you didn't ask what was the biggest catalyst in my life. It was divorce. It was the destruction of the narrative. It was, I'd built a life. That I thought everyone could be proud of. And a relationship is a one-on-one project, not a community project. And I was projecting out all the time of this. If you watch even podcasts that I did when I was married, I was always put it on a pedestal of everything else. And I had a good marriage. Like, we loved each other and we didn't fight and there's nothing like that. It was just, I wasn't present. I wasn't present enough. And our trauma met up perfectly. And I think we were, we are in each other's lives to be partners for those kids forever. We have three beautiful kids. She's a wonderful person. I'm grateful that it's her.
1:01:46 Speaker 00 But when that happened and we couldn't get back, the pain of that caused me to do something I'd never done before, which was do this work. That pain caused me to hit rock bottom. Did you feel like you were letting your parents down? I thought I was letting everyone down. I thought I was letting down the kid who I said on a podcast that I want to show that you can be a good executive and a good husband and a good father and all this stuff that I did. And I realized, you put your relationship on a pedestal, you're not paying attention to your relationship. The next time around, it's for me and for them. And I'm not interested in projecting or anything like that. I learned a lot. And I can tell you, that moment in my life was the moment where this story that I had built of Scooter wasn't working. If I didn't have Scooter, then what's underneath? But I hadn't had a foundation of Scott. And that's why I started to crumble.
1:02:31 Speaker 00 It's so similar, all like ex-girlfriends minded like, am I getting Harry? Or like, brand Harry? It's interesting you say that because I've done that my whole life as I was dating. You'd start off great and then they'd get to a point and they'd see how you operate and they wonder if you're doing it. And the truth is, I'm always giving them brand Harry. I think you're always giving them brand. I used to hear that. You're so much more self-aware than I was at this age. I just got to say again how incredibly impressed I am by you. Thanks, man. No, I'm really just blown away, even by what you just said. It moved me because at 25, at 30, I didn't know to say that. Because I thought being Scooter was authentic. Because I didn't remember who Scott was. And I didn't love who Scott was and I had left it so far behind. You still know who that other dude is. You're aware enough that he's right there in front of you and you can grab him and
1:03:16 Speaker 00 you could do the work far before I did. You don't have to hit that rock bottom.
1:03:20 Harry Stebbings? The hard thing I find is actually separating the two. And actually, you can become, I don't know if you found this, but you become the brand that you create. And then you can lose yourself.
1:03:29 Speaker 00 I think the most important thing is starting to realize that this brand you created was created by you. That the strong one was you, not the brand. I think that's the lie we tell ourselves as we build this through our childhood. We build this mask, this armor, because we don't think we're enough. And then you get to a place, that I'm working on now, realizing, wait a second, that little kid built this. I didn't need to leave him behind. He's actually the strong one the whole time. And that's what I'd offer to you. The brand is something that, that person that you thought didn't have friends because you were studying. That person that you thought, I've heard you make a lot of kind of degrading jokes about yourself early on. That person that you're degrading built this person that everyone seems to be so impressed by. And I think that you should give yourself a lot more credit.
1:04:12 Speaker 00 We come through all this trauma, I think we spend the first half of our life learning, and then we spend the second half unlearning. That's why I'm so impressed by you, because you're asking all these questions so early. And I was asking questions about family so early, and how to build a family and everything else. But I wasn't asking questions about myself. I'm still living in this narrative. I didn't like my name Scott and all these different things. And I think you're asking these really beautiful questions that make me see that you're just so much more aware than I was. And I think that's probably why people like listening to you.
1:04:38 Harry Stebbings? What do you think is the thing that you need to unlearn, but you're yet to unlearn? Like, the future unlearning?
1:04:44 Speaker 00 I've been thinking about this a lot, and I actually figured out a way to describe it. Let's say you had a friend, and throughout your life, this friend had shown up for you time and time. Every time you get in trouble, this friend bails you out. And every single time you're worried, this friend shows up. And
1:04:59 Harry Stebbings? Jack.
1:05:00 Speaker 00 No, no, listen, no, hear me out, hear me out. And this friend has literally shown up every single time. To the point where, would you say right now at 25, you're living a pretty extraordinary life?
1:05:11 Harry Stebbings? Yeah, 100%.
1:05:12 Speaker 00 100%, right? When you take away your fears and everything else, you just look at the bare bones minimum of like where I am in life. It's pretty extraordinary what you're doing. What we're doing right now, the position that you're in, it's really extraordinary 25 years old. Agreed?
1:05:25 Harry Stebbings? Sure.
1:05:25 Speaker 00 Okay. If that friend helped you more than anyone get to this place. And you question that friend every single day. Every single time the friend showed up again, you questioned it. How do you think that friend would feel?
1:05:37 Harry Stebbings? Surprised.
1:05:38 Speaker 00 And also probably a little what the fuck? And you're looking at me because you're thinking, I would never do that to that friend, correct?
1:05:44 Harry Stebbings? Yeah.
1:05:44 Speaker 00 Okay. What if I told you the universe has shown up for you every single time? And look where you are. Every single time that you've been in a tough position, the winds have gone in your direction. Enough. You've had trials and tribulations, but enough that you are standing here right now in the position that you are in. Yet you go home still questioning if you're enough or if you can trust the world and is it going to go in your direction? But for 25 years, it's given you extraordinary results. Yet you go home and question it every single day. Why do we do that? I don't know. I'm working on that. I think that's called faith. And I'm horrible at faith. That's a thing I can admit. I'm getting much better at it, but I still at the last minute want to just go like this. Just want to push it a little bit. I want to get involved.
1:06:24 Harry Stebbings? Why are you bad with faith? Is it the lack of control? Because you are delegating all control when you enter faith.
1:06:30 Speaker 00 I think all entrepreneurs are bad at faith. Because you don't think you're bad at faith?
1:06:35 Harry Stebbings? I think I'm excellent at faith. And I think I'm terrible at faith.
1:06:38 Speaker 00 Yeah, and I think it's because we believe we're manifesting. But we're coming into this, it's because we're so afraid of failing. We're so afraid of not being enough. We want to get it there. We're doing everything else.
1:06:47 Harry Stebbings? Mine's the control mechanism. With faith, others said, it's okay. If I control this.
1:06:51 Speaker 00 It's going to be okay. And you don't really trust anyone else to get in there? Okay, so there's a great book, Guy wrote, and Tethered Soul, Michael Singer wrote a book called The Surrender Experiment. You should read it next. And he talks about this concept of the universe has been moving just fine without us for billions of years. Yet we come in our 60 to 80 and act like we manifest and we're controlling things. It's an illusion. Now, I believe like a basketball game. LeBron James, at the height of his career, Michael Jordan, height of his career, these guys could control games? No. They could influence games. I think we participate. And some of us are better at participating than others. But no one controls it. No one. We're all participating and then the universe shows up and we should put a little
1:07:33 Speaker 00 more trust in it. And what I'm working on is having a little bit more faith that things are gonna be okay. In fact, I have tattoos. My newest tattoo, this week, I woke up, went to a tattoo parlor in New York and got faith tattooed on my ribs. And it was, my friend was like, why on the ribs? And just the word faith. And I thought to myself, I don't know where this came to me, but it was the story of Adam and Eve. God took a rib and he took a rib because he wanted to make Adam's equal, that he wasn't gonna be alone in the world. And I put right where that rib is, the word faith, to remind myself that it's all gonna be okay. I'm not gonna be alone in the world. I gotta have faith, it's going to be okay. And I think especially entrepreneurs, we struggle with this because we know the thing no one else knows, which is when everyone else was quitting, we went that extra mile
1:08:15 Speaker 00 because we were afraid. And that little extra mile, we think maybe that moment when I was about to go to sleep and quit, but I decided to stay up and go a little bit harder, that was the moment that made the difference, that turned the winds. And we believe that. And by the way, that's influence, but that's not control. Our control's an illusion. I say that logically, but ask me if I'm acting on that yet? I'm still working on it.
1:08:37 Harry Stebbings? What achievement are you most proud of?
1:08:38 Speaker 00 My kids. Like, it's not even, it's, any parent understands that question. It's, I get emotional. Like, it's, I have really great kids and I know that one day they're gonna go and do self-work and yell about me one day. And I'm actually hoping they do. I hope I give them enough freedom and enough unconditional love to know that they're allowed to do that, that they can get to the patterns that I didn't get to.
1:08:59 Harry Stebbings? I have to ask, you said this with Jay. You said you gave them transactional love.
1:09:03 Speaker 00 In the beginning.
1:09:04 Harry Stebbings? Yeah.
1:09:04 Speaker 00 Because that's what, I feel like all parents, like so many of us, we're not trying to, but our trauma has us doing things that come across transactional. I think that I love my kids unconditionally and I'm working on making sure that's clear all the time. I sure heard this speech someone gave and I gave it to my kids the other day in the car. I said, I want you guys to know that I love you, that I think you're amazing. I think you're amazing just the way you are. I don't just love you, I like you. I like you when you make mistakes. Like, I did this whole thing and I just saw their little faces start to light up when I said, I don't just love you, I like you. And I want them to hear these things because they're gonna do some stupid shit one day. And they're gonna do stuff that pisses me off. They're gonna do stuff that scares the shit out of me and I'm gonna make so many mistakes as a parent. I'm sure I have already. I know I have. But I just, I want them to know that they're allowed to be their own person. And I think
1:09:49 Speaker 00 getting to participate in their life as their father is the greatest achievement I'll ever have.
1:09:55 Harry Stebbings? Final one, do you worry about the influence that money has? My money is a great luxury in many ways, but it's also challenging and bringing children up with the same hunger and ambition is tough. Do you worry that's?
1:10:07 Speaker 00 Yeah, I do worry about that. So I spoke to a lot of kids who I thought were amazing human beings who came up with a lot of wealth. And two common denominators I found after interviewing so many kids and their parents of the great ones. One, accountability is the number one common denominator I find. Their family raised them with this accountability. Took time one on one to really speak to them about accountability. So even it wasn't like they weren't aware of what they were they had or they could get. They felt accountable to the world and I think that's important. They understood equality. They understood their place in it. They understood their responsibility humanity. They understood that their actions matter. I think accountability is really important. And the other one was identity. Without saying names, someone I know had a family member who was really struggling and then he was not.
1:10:50 Speaker 00 And I asked why and he said in his other family member situation, he didn't know where he fit in because with his parents, no matter what he achieved. He felt like his dad could do everything, so he didn't know how to compete with this person. His dad was really good at one thing and he got to choose something else. And I think having a sense of your own identity is really important and I want my kids to know that they're allowed to have their own identity. They don't have to follow in anyone's footsteps that I encourage them to be whoever they're going to be. Cause I think having a sense of self is one of the most important things because whether you have wealth or don't have wealth, you're still having a human experience. Your normal is your normal. So I think, like I said, doing that self work and having the freedom and the encouragement to do it is really important.
1:11:30 Harry Stebbings? I always think the most important thing you can ever say to children is just I'm proud of you. And maybe it's me, but it's just like the only thing that matters is their approval.
1:11:37 Speaker 00 I disagree.
1:11:38 Harry Stebbings? But you're the parent, so I'm the naive.
1:11:40 Speaker 00 I I disagree because I used to believe that and it's really interesting that you.
1:11:43 Harry Stebbings? Just constantly seek the approval. I would be so happy to hear, Scooter, I'm proud of you.
1:11:48 Speaker 00 Yeah, I want you to hear what you just said because I used to say the exact same thing. You didn't feel like you were enough until you heard I'm proud of you. You thought you would get I proud of you by doing things, by achieving things.
1:12:02 Harry Stebbings? Being in the soccer team, being in the.
1:12:04 Speaker 00 So I'm gonna tell you what I think the most important thing is my kids can hear. I love you exactly the way you are and I support you in whatever you do. Because I want my kids to know, and I think you deserve to know and I deserve to know, that you don't need to do anything to have love this way. Because that's why it's confusing for us. Because when we come into the world, I get it. My kids love me unconditionally. I've heard you talk about your dad and your brother before we started. Your dad could do anything and you're still showing up for him. He loves you, you know that, but you're showing up for him unconditionally. I think the most important thing a kid can hear is that the parent feels the exact same way. That I'm proud of you because of who you are, exactly the way you are. I'm here to support you in everything that you do in life. But you don't need to do anything to get my approval.
1:12:47 Speaker 00 I want my kids to know that because I think that you would have a different answer. You would, it's the pride is a result based feeling. I get that because as a parent, you also want your kid to go for things. Sure. And you want to teach them that. Do you think your kids get that? I don't know. I know that I'm gonna try. I know that we are gonna try. We're great parents together. Yeah. And I think that we're both gonna do the best job we can to tell them to break those patterns. Because here's the thing, I once told this to my dad. My dad and mom love me. And when I did this work, I went on a walk with my dad and I said, Dad, I now know that you love me so much that I see through your lies. Because my dad did that. I'm proud of you. Because that's what happened to him. That's what he knew and that's a beautiful thing. It's what he knew. So everything was result based.
1:13:32 Speaker 00 I had to win the basketball game, I had to do this. I knew my dad loved me, but he made it result based feeling for a child. And I now know, my dad would never leave me. But as a child, you don't really know that. You're deciphering things in a weird way because you don't, you're learning the world. And as adult, I now realize that all those things he said of I'm proud of you if you do this, or I'm proud of you because you did that, were all bullshit. He was always proud of me. He just didn't know to tell me because he grew up a certain way. I will tell you this, if it helps. I have no idea, I haven't even looked up your fund. You told me you have the fund. I have no idea what your investments are. I didn't, I actually chose not to look. I'm here because of a conversation we had where you were vulnerable and showed me who you were.
1:14:14 Speaker 00 So I'm proud to know you. I look forward to being friends with you for a long time. I look forward to these kind of conversations. If you become uber successful commercially, which I'm sure you will, because I can just tell you're destined for that, I'll be happy for you. But if you don't and you choose a completely different path, I'm going to be just as proud to know you.
1:14:30 Harry Stebbings? I really appreciate that, man. You get nervous when you open up. Do you know what I mean? You're like, oh, God, you feel very naked.
1:14:37 Speaker 00 Yeah, I was with a founder yesterday I met with, a new company. And we had this really great thing and I was giving him this kind of advice because he was pushing on me to give it to him. He was younger than me. And I don't want to feel preachy. I don't want to feel like the old man. And then at the end, he said, he goes, just so you know, when I was doing my research, there are some people who say you're a shark. That like you are, you're like an amazing deal maker, but you're a shark. You gotta watch out for you. And I felt this need in the moment to get defensive, right? To be like, who are those people and do they really know me? And I caught myself and I went, look, I don't know what to tell you. If they said that, they have a reason that they said that. I'm going to present myself the way I'm going to present myself to you and I know who I am. And I wouldn't have done that five years ago. Five years ago, I would have found myself for 20 minutes defending myself and saying, I want to know who that person is.
1:15:21 Speaker 00 And all this different stuff and you know, who said that? And it doesn't matter because the truth is we're all living our own experience and misinterpreting each other. And sometimes we're telling the truth and sometimes people see truth in you that you don't want to admit is there because you did fuck up. Or you were a little bit manipulative in that moment because you were scared yourself and you were dealing with your own stuff. And that's why I don't like cancel culture. I think we all have to give ourselves the grace to grow. If I could change drastically in a week, why can't we give someone an opportunity to change over years? And we do it with jail. Someone gets out of jail and like they tell us the story of their life before they went to jail and they get out. We're like so gracious. We're like, oh my God, this is such a beautiful story. Do you know this person was once in jail as a criminal and now look at them?
1:16:02 Speaker 00 But then we find something someone said on the internet 20 years ago and we act as if they aren't a new person today.
1:16:08 Harry Stebbings? Can I ask one and then we'll do a quick fire. You do many interviews. You've had many questions asked of you. Are there ever questions or is there anything that I haven't asked that you think I should ask? Is there ever a question that you wish someone asked of you that they don't ever ask you? I find often no one ever actually asked that because I'm always asked the same thing.
1:16:27 Speaker 00 Yeah, I guess.
1:16:27 Harry Stebbings? How do you get into the industry?
1:16:29 Speaker 00 I find that like different interviews go into different places. Like this one went to a very deep philosophical, personal place. I think people were expecting and even my partners were expecting for you to go deep into my investment strategy, how I invest. By the way, I'm good. I'm happy that we did this because I think this will actually make a bigger influence. Yeah, I actually think so. What do people have never asked me? No one's ever asked me if I find myself successful.
1:16:52 Harry Stebbings? Scooter, do you find yourself successful?
1:16:55 Speaker 00 I think for the first time in my life, I'm getting there.
1:16:58 Harry Stebbings? What's helping you get there?
1:16:59 Speaker 00 That when you just said scooter, do you find yourself successful? I'd actually prefer if you say Scott.
1:17:05 Harry Stebbings? Huh. How long ago, like how recent is this?
1:17:08 Speaker 00 It's only over the last two, three years. And I think I'm perfectly fine being called Scooter. I'm very proud of the achievements of, but when you asked me that question, even though I posed it to you, I felt this visceral reaction inside of me of then he's asking the wrong person. I think now that I'm getting back to that version, that I'm accepting that kid created all this, becoming prouder of myself. So yes, I think I'm getting there as I embrace a piece. It's actually funny. It's a piece of advice that my grandmother gave me a long time ago. And I've said it so many times, but I think this moment right now is the first time I truly understood it. She said, being mature is loving your 12 year old self. She goes, we get to about 12, we hit that teenage years. We're like, think we're not cool. We go through all these different things. We start to create that shell.
1:17:51 Speaker 00 And when you become mature, you actually realize you were always good enough at 12 before you started going through that teenage insecurity stuff. This moment is when I realized like I was Scott. And I think the more I accept that version of me, the more I accept the version that I'm proud of me exactly the way I am. Then I start to feel more successful. And it's funny because all the things that I thought I had to build to be successful had nothing to do with that.
1:18:15 Harry Stebbings? That's a big one. I'm really happy for you. That's a big thing. Do you wish people would not call you Scooter then?
1:18:20 Speaker 00 No, like I said, I'm very proud of my life and what I've done and the things that I've been able to achieve and the things that I want to achieve. But I like the fact that for the first time in a very long time, I like calling myself Scott. It's not about what other people call me. I'm cool with either one. It's been a part of my journey, but I haven't been comfortable with that name probably since I was six years old. Three years ago, I would tell you I don't even like that name. And I shouldn't have been named that name. It's why I like Scooter, because I never felt like I was a Scot. And I absolutely love my name now.
1:18:50 Harry Stebbings? We're gonna do a quick fire round, otherwise I'm gonna be completely unable to afford your brilliant therapy session, please. And so I say a statement or a quick question and you give me your 60 second thoughts. David Geffen is your mentor. What's the best advice he's given you?
1:19:03 Speaker 00 He's given me so many pieces of great advice. David Geffen told me that in a hundred years, no one's gonna remember him, so they sure as hell won't remember me, so don't have an ego. And I think he's right. In a hundred years, they'll feel my impact, but they won't remember me. So don't treat myself like I'm something special. The other thing he said to me, which was very powerful, was if you have people calling you saying, oh, you need to know this person's talking shit about you, you should probably remove those people from your life, too. Because half the time, they're talking about someone who you don't even see anymore, or they're barely in your life, and all they're doing is stirring up drama.
1:19:35 Harry Stebbings? Yeah, one question I ask loads of people, especially in this industry, I say, do you ever hear anything bad about me? Do you ever hear anything bad about me? It's almost like I'm seeking. Do you see what I mean? And they go, yes, actually. And I'm like, oh, I knew it.
1:19:46 Speaker 00 I think we seek the things we're trying to justify.
1:19:48 Harry Stebbings? Yeah.
1:19:49 Speaker 00 And if we feel bad about ourselves, deep down, we're trying to find someone to say it's true and then go fight it so we can beat ourselves.
1:19:56 Harry Stebbings? Yeah, I think financial safety is this big thing. I think about quite often.
1:20:00 Speaker 00 I think you're right. And the reason I say you're right is I don't think you need, like that Bezo story I told you, I didn't tell you that. He said to me, I said, what do you want out of life? Jeff said to me, I want to evolve. I want to be a better father. I want to be a better friend. I want to be more intimate. And I realized you don't need $200 billion to start that, right? It was like a cheat code he gave me. But I will say this, because I've seen these comments when I've talked about this online before, where people will be like, oh, it's easy for you to say that because of your financial safety. And I want to actually say I acknowledge that. I think that there's something to be said. When I told you earlier that money is an avenue to freedom if you let it be, I have the financial freedom to take time off to go work on myself. I acknowledge that my grandfather, when he came to this country, wasn't fully in that position. His family needed him to go to work every single day.
1:20:43 Speaker 00 But I think that's actually what the American dream was about, putting your family in a better position so they have a better opportunity. My grandfather came to this country, my father. And put me in a position so that I could go and do this and break generational patterns. I don't think he put me in this position so I could go be rich. I think he put me in a position so we could have a better life. For me not to acknowledge that would be ludicrous. I think it's better to acknowledge it, but then people need to look at their own situation and really ask themselves, do they have enough freedom to go take a week off once a year? Most people will be able to say yes. Tell me, Dave Clark once told me, is it true you were once a backup dancer? I got hired when I was younger to dance at bar mitzvahs and weddings. I was at a teen club and some guy offered us and I could, I could dance. Yeah, that was my first
1:21:28 Speaker 00 job in entertainment technically. And then I danced in a couple of music videos for friends. But yes, I could, I could pop and lock and stuff like that. What have you changed your mind on in the last 12 months? Actually, can I tell you something funny about the dancing thing? So people can have a laugh. Have you ever seen the show Dave? That's an amazing show that we produce on FX with Little Dicky, his character Dave. It's biggest comedy in FX history. And Benny Blanco is on the show. Benny Blanco is a very huge music producer. He's one of my best friends. We've known each other since we were young. Benny saw a video that's on my Instagram of me dancing, like joking around. And he called me up and he goes, I was thinking about it. This is how many talks. He goes, I was thinking about it. I saw that video again and it blows my mind. And I was like, what blows your mind? He's, you spent so
1:22:10 Speaker 00 much of your life training in basketball just to become a mediocre basketball player. If you would have just trained half of that at dancing, you'd be amazing.
1:22:22 Speaker 00 You're like, I'm available anytime. Tell me, what's the most painful lesson you've learned that you're also pleased to have learned? I think learning how to be present has been the most rewarding lesson of my life, which I'm still working on every single day. How I learned that lesson was the most painful thing I've ever gone through. What was the favorite memory from working with Justin? My favorite moment of working with Justin? Is not like the stage or the accolades. It was backstage moments. It was laughing together. It was watching him do Make-A-Wish grants when no one knew he was doing it. It was when all the noise is gone and all the people talking in both of our ears, all the stuff that has come into our lives, when it's just us, like those moments. Those are the ones I cherish the most and that's why we'll always have a special relationship.
1:23:06 Speaker 00 Because we created something very special together. And he is one of the most talented people I've ever met in my life, but also one of the bravest people ever in my life. To be able to do that through his adolescence and then to transition into adulthood and become the man he's become, and I think I'm always proud of him.
1:23:21 Harry Stebbings? What's the biggest challenge that you see in the incredible scaling trajectory of the people that you work with? When you look at Justin when you started and then many others when you start and then where they are today?
1:23:32 Speaker 00 I'll think of Ariana because I just saw her yesterday for dinner. I'm only just using her as an example. This is someone who lost someone she loved. This is someone who had a very public breakup multiple times. This is someone who then had to live through a terrorist attack at her own show. And this is someone who had to grow up in the public eye as a child and came from a home with two parents who weren't together. And is one of the most talented people ever. And she and I talked about it yesterday. One of the reasons why she feels so much is because I think when people are that talented, she can impersonate anybody. She feels everything. She's a true empath. And I think the world can become very scary for someone who feels everything. Especially when there's so much of a spotlight on the world back on you.
1:24:17 Speaker 00 And I think we live in this world where everyone gets 140 characters and truth doesn't really matter. Someone gets a little momentum with the story and it just starts to go. And I think having to work with people in that situation and have them at a very young age have to learn that bravery is one inspiring, but also it's hard to navigate at times. And I was a kid. You have to understand, I was your age when I discovered Justin. I was 25. I was in my twenties when I discovered Ariana.
1:24:42 Harry Stebbings? How did you discover Ariana?
1:24:43 Speaker 00 She sang a cover of Justin's called Die in Your Arms. I saw it on YouTube and I was like, why is Nickelodeon not signing this girl? And then she was at Universal, was doing, had done the deal and I was like, I need to work with this girl. And I found out she was actually trying to reach me, but no one told me. So when I reached out, they were like, we've been trying to reach you. And she actually sang Die in Your Arms, hoping to get my attention. I think people don't realize that these are human beings, having a human experience, and these are extraordinary times where social media is putting such a highlight on them. And mental health is a real thing. I think Surgeon General of the United States said the number one killer in the US right now is depression, and it's mostly with young people. So I think I was a kid when I was going through this. You talk about mistakes. I wish I understood more about mental health at that young age. I wish I would have got the people I worked with more help. But I didn't know, and I didn't come from a family who had therapy.
1:25:27 Speaker 00 When you ask me the struggles and the things that I've witnessed, it's the same thing we're discussing. The biggest struggles in life aren't getting on that stage, or how do I make another hit song? Or how do I build a VC? Or how do I build a company? It's how do I get through the suffering of the human experience?
1:25:43 Harry Stebbings? What would you most like to change about the music industry?
1:25:45 Speaker 00 Oh, when I came in, everyone was like, oh, you're crushing it, but this is a dead industry. And all the valuations were way, way down. And everyone's, oh, you should have seen the years when we were selling cassette tapes and how many, everyone was platinum every week. And then Daniel Ek came along and transformed everything. And now it's the richest it's ever been, thanks to his vision. And people don't give him enough credit. And that's why, if you look at those early interviews, Daniel will tell you, like, I was the manager who was like, just send them my way. I was like, I'm gonna... Everyone was crapping on them and I would...
1:26:11 Harry Stebbings? What did you see that others didn't?
1:26:12 Speaker 00 When I was in college during Napster, so I knew it was coming. I knew they couldn't stop it again, because I used it.
1:26:17 Harry Stebbings? I remember Napster.
1:26:18 Speaker 00 Yeah, I used Napster a lot. I was a big Dispatch fan, thanks to Napster. But I knew it was coming. I understood it was coming. I understood it couldn't be stopped. Number two, I met Daniel, because we were on a billboard list for 30 Under 30. And I called everyone on the list to introduce myself, because I wanted to know my peers. And there was a guy in Sweden, and I called him. He was coming to LA two weeks later. And I said, let's meet up, and we became friends. And him and Shaq didn't let me invest in damn Spotify for another year. I was like begging Shaq and him, like, constantly. I love those guys. And I'm very grateful I got in. But what's the biggest change in the music industry is that it's become a global industry that now can be monetized. And I think it's only going to get bigger and bigger. I think a company like Spotify is going to grow 10% to 12% year over year for the next 10 years. You look at the numbers and the populations that they're going into, I just only see growth from here.
1:27:01 Harry Stebbings? What would you... Most want an entrepreneur listening to this or a young person listening to this. Young person's probably better, given what we've discussed. What would you most want them to take away from this channel?
1:27:12 Speaker 00 I already said it, but I'll say it again. No matter what journey you're on as an entrepreneur, working, volunteer, founder. We've all talked about this. We all talk amongst our friends of all different jobs. We're all pretty much going through the same thing in different ways. It's almost like all the major religions talk about the same thing. If I could give anyone any takeaway from today, I hope that they don't take like me thirty nine years to get to a place where they take one week a year, no phone, no email and do a week of self-work. If you start that now, you'll be so far ahead of me.
1:27:44 Harry Stebbings? Final one, you you put this one on me, I'm gonna turn it on you. Next five years for you, why do we want that?
1:27:50 Speaker 00 Phew, I think for the first time in my life, I don't know and I'm excited about that. I know that I'm going to be heavily involved in my children's lives. I know that I'm going to keep working on myself and I think for the very first time, I have no idea what it looks like. And I guess I'm going to have a little bit of faith.
1:28:05 Harry Stebbings? Thank you so much for doing this. I've never quite been so open. I'm slightly terrified about having been so open, but honestly, this has been. Shows like this are why I love what I do. You know, you ask what gets you open. This is why I love this so much. So thank you so much and this has been so special.
1:28:21 Speaker 00 I am incredibly grateful we did this and I'm glad that we had that conversation on the phone that day and I got to meet you. And I'm looking forward to watching not only your success, but your real success as you continue to grow. And you got a friend in me, so we can bitch to each other when we're scared.
1:28:35 Harry Stebbings? Do you know what's so funny, man? It's um, it's that normally there's like, great, and then you switch. And what I mean by the switch is the brand Harry to the Harry. Do you see what I mean? And literally normally I do a clap and it's like, great. Oof, it's just kind of honestly, this feels weird.
1:28:51 Speaker 00 Cause this, cause you can't go to the brand?
1:28:53 Harry Stebbings? Yeah, there's no switch. It's not like I'm moving between characters.
1:28:56 Speaker 00 But.
1:28:56 Harry Stebbings? Does that make sense?
1:28:57 Speaker 00 Yeah, cause you don't have to.
1:28:59 Harry Stebbings? Yeah.
1:28:59 Speaker 00 And I think, one, you don't have to, I don't have to, but I also think I said something to you. I don't want to assume anything, but I think I said something to you that's different than what you said. You said, I just want someone to say I'm proud of me. And I told you, you didn't have to do anything for me to be proud to be your friend and that you don't need to switch. And I'm really happy that you're asking those questions and wanting to figure that out now instead of fourteen years from now.
1:29:22 Harry Stebbings? Yeah, I should do the Hoffman.
1:29:25 Harry Stebbings? I listed before and I told you I was just like, I'm too busy.
1:29:28 Speaker 00 Oh, in four or five years, I backed out. People were telling me I should do it. My friends who loved me, remember you said to people who was there for you? I look back now at how many friends saw me and told me to do that. And here I was thinking, no one's here for me. I just ignored them because I didn't want to see them. And now, when I finally did it, I look back and realized how many beautiful people were trying to tell me they were there for me and I didn't want to listen.
1:29:51 Harry Stebbings? And you didn't want to because you were scared to do it or?
1:29:53 Speaker 00 Yeah, I thought I was in the matrix. I was narrative was running.
1:29:56 Harry Stebbings? And strength.
1:29:57 Speaker 00 And I was just like, I'm good, I got my plan, I'm doing this, I'm good, I'm happy this. Because I told myself like this is as long as I'm doing this, I'm okay. The universe was like, eh eh, and it kicked my ass, thank God it did.
1:30:09 Harry Stebbings? I think you'll agree with me in saying that was one of the most special shows we've done. I want to say a huge thank you to Scooter. He's become a friend in the process. I want to thank him for making the space to have this conversation. It was, as I said, a nerve wracking one for me to be as open as I was in this. So huge thanks to Scooter for making it so special. If you'd like to see more from us, of course you can on twenty vc dot com. You can see the whole video on YouTube by searching for twenty vc. But before we leave you today, are you building enough conviction to outpace other investors in this changing ecosystem? Tegus helps VCs get under the hood of their investments quicker, map evolving markets with deeper research, monitor the financial health of portfolio companies and even source new deals. Tegus is trusted by top firms like Redpoint and Spark Capital
1:30:52 Harry Stebbings? for everything from expert calls and transcripts to quickly surfacing insights across filings, comps and benchmarking. Find out why a majority of the top venture funds are using Tegus on a daily basis to differentiate, consolidate and accelerate their research. Head to tegus dot com forward slash growth for your free trial. And speaking of tools we cannot live without there, Secureframe is the leading all in one platform for automated security and privacy compliance. Secureframe simplifies and streamlines the process of getting and staying compliant to the most rigorous global privacy and security standards like SOC two and others. And Secureframe's industry leading compliance automation platform, paired with their in-house compliance. Experts and former auditors helps you get audit ready in weeks, not months.
1:31:36 Harry Stebbings? So you can close more deals faster, automate your security and privacy compliance with Secure Frame. Schedule a demo today at Secureframe.com. That really is a must. And finally, are you tired of using the same old tools and platforms in an attempt to manage your global team? Well, us too. Why use 16 different tools when you could just use Deal? Deal is the only global first HR tool with unmatched automation, customizations and integration, making it the only platform for built-in contracts, visas, background checks, payroll, equipment, benefits and beyond. Are you ready to see how Deal can scale with your global and local teams? Visit Deal.com/20VC and book your demo today. That's Deal.com/20VC
1:32:21 Harry Stebbings? to book your demo. As always, I so appreciate all your support and stay tuned for our episode on Wednesday with Mark Goldberg, Head of Enterprise Sales at Ramp.
Previous 20VC: Biggest Challenge Facing Crypto Today & The Winners and Losers of the Next 10 Years | Why AI Will Lead to More Wealth Equality Than Inequality | Why The Current State of the US Feels Like the End of an Empire with David Marcus, CEO @ Lightspark Next 20Sales: Why You Should Never Hire a VP Sales First, How To Create Urgency in a Sales Process, How to Do Traditional Outbound 10x Better, Why Revenue Doesn't Matter with Your First Customers | Mark Goldberger, Head of Enterprise Sales @ Ramp Page updated October 25, 2026 · transcript and summary are machine-generated
