Leap Academy with Ilana Golan - Kickstarter Co-Founder: How Yancey Strickler Built a $7B Platform That Transformed Crowdfunding | E157

Episode Date: May 5, 2026

When Yancey Strickler moved to New York, he was broke, freelancing for $50, and chasing a writing career. Little did he know, his gift for building on the internet would soon change the world of crowdfunding. A chance encounter with a friend and a half-baked idea about crowd-funded concert tickets led to the founding of Kickstarter, a platform that has raised over $7 billion for creative projects worldwide. In this episode, Yancey joins Ilana to discuss his journey from freelancing on a shoestring budget to building a billion-dollar platform and what it took to survive the hardest moments. He also explains his bold plan to help artists participate in capitalism. Yancey Strickler is the co-founder and former CEO of Kickstarter, the platform that raised over $7 billion for more than 200,000 creative projects. He now runs Metalabel, a studio building tools for creative cooperation. In this episode, Ilana and Yancey will discuss: (00:00) Introduction  (03:11) From Music Households to Manhattan Bylines (06:28) The Side Project That Changed Everything (13:34) The Ladder Vouch System That Launched Kickstarter (18:57) Why Showing Up as an Open Box Wins Every Room (26:31) The Day Two Projects Hit a Million Dollars at Once (33:40) The New Definition of Work in the Age of AI (36:28) Building the Legal Blueprint for the Artist Economy (43:09) Why the Private Internet Is Where the Real World Lives (49:38) Q&A: How to Open Doors to New Connections Yancey Strickler is a writer, serial entrepreneur, and the co-founder of Kickstarter, the global crowdfunding platform that has raised billions for creative projects.  He's the author of This Could Be Our Future and The Dark Forest Anthology of the Internet and the co-host of the New Creative Era podcast. Before Kickstarter, Yancey was a music critic for outlets like Pitchfork and Spin. Today, he leads two bold projects: A Corp, a legislative effort to provide artists with real economic infrastructure, and DFOs, a platform reimagining the private internet.  Connect with Yancey Yancey’s Website: https://www.ystrickler.com Yancey’s LinkedIn: https://www.linkedin.com/in/yancey-strickler-486b4557/  Yancey’s Instagram: https://www.instagram.com/ystrickler/  Yancey’s X: https://x.com/ystrickler  Resources Mentioned: Yancey’s Books, This Could Be Our Future: A Manifesto for a More Generous World: https://www.amazon.com/This-Could-Our-Future-Manifesto/dp/0525560823  The Dark Forest Anthology of the Internet: https://www.amazon.com/Dark-Forest-Anthology-Internet/dp/B0D14NN1DN  On the Creative Life: Conversations Toward a New Creative Era: https://squad.metalabel.com/onthecreativelife?ref=ystrickler.com&variantId=1  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

I grew up lower middle class, assumed I would always be broke. The first four months that Kickstarter was live, I still had my day job because I was worried about losing the income and I was doing Kickstarter customer service at night. Yancey Strickler is the co-founder and former CEO of Kickstarter, the platform that redefined the world of crowdfunding and helped raise over $7 billion for more than $200,000 creative project. My partner Perry wanted to throw a concert and was needing to front 30 grand for it to happen. You thought this is stupid.

Why can't I just propose the idea for the concert online? People put up their credit cards to buy tickets, but they only get charged if the show sells out. That was the energy that we could feel Kickstarter was about. AI is making everything worse, right? Because now you suddenly have all these ghost songs that suddenly less and less people want to pay the artist. This feels like a real breaking point. of a way of the world is ending, has ended. A new way of the world is beginning.

I think more and more people will be entrepreneurs, portfolio careers. That means a lot more people need to cope with being on their own. I think the way you balance that, one is through a personal practice of caring for yourself, which I got much later. Most of the time as a leader, the right thing is to like just...

Welcome to the Leap Academy with Ilan Show. I'm so glad you're here. in the Leap Academy podcast, I get to speak to the biggest leaders of our time about their career, how they got where they are today, the challenges, the failures, and countless lessons. So lean in, this episode is going to be amazing. I'm in a mission to help millions reinvent their career and leap into their full potential, land their dream roles, fast-track to leadership, jump to entrepreneurship, or build portfolio careers. This is what we do in our Leap Academy programs for individuals and teams.

And with this podcast, we can give this career blueprint for free to tens of millions. So please help my mission by sharing this with every single person you know because this show has the power to change countess of lives. Deal? Okay, so let's dive in. Yancey Strickler is the co-founder and former CEO of Kickstarter, the platform that redefined the world of crowdfunding that I'm sure you know and helped raise over. for $7 billion for more than 200,000 creative projects. Now, after stepping down as CEO, Yancey shifted his focus to deeper missions. And we'll talk a lot more about his different things.

But I can't wait to hear more about you, Yancey, because your journey, speaking of Leaps and Leap Academy, you did some really interesting leaps here. So I want to take you back in time. And first of all, to just welcome you here. Thank you. Thank you. I appreciate that. It would be great to be here. So take us back in time. I think you're a son of a musician and you actually started in music, right? So like I think for people who are in tech and assumed that you've been in tech all your life, like I think that might surprise them a little bit.

So take us back in time. I grew up the son of a musician, as he said, and so was always in a creative household. My father didn't make it in like a big record deal kind of way, but played for love and was always in bands. And the creative life was just always a part of how I saw the world and experienced the world. But I was a better writer than a musician. I did play music, still do, but a better writer than a musician. And my dream was to be a journalist. I did that as like an internship in high school for a local newspaper.

ended up moving to New York, and my first job was as a journalist for a radio station. It was writing about music and entertainment news every day, making something that had a pun in the headline, and would be funny for a DJ to read out on air as well as informative. And that to me felt like a path that matched just a natural curiosity I had for learning about things and for loving to just absorb as much information as possible, as well. as a gift of story I always liked. Did you know what you wanted to do at that moment? Or was it just kind of like,

let me just see where life takes me? I just said I wanted to be a writer and I had freelance writing gigs where I made 50 bucks a pop. I don't know that I had a real image of what that led to. I just wanted to keep doing it because I could feel every piece I got published,

I got better, and it just felt natural. There was no clear destination I really had in mind. And I was just working extremely low-paying jobs, but living in New York, which was my dream, and having a good time. And music was still part of this, or are you just kind of playing from time to time for fun?

I wasn't making music during that time, but that was what I wrote about. I wrote about music for the Village Voice, and I would discover new bands. And I even started my own record label and started putting out music by people, I found and I liked. And so I just got deeper into it. And I also got editorial day jobs in companies that also had tech functions, you know, like a marketplace that also had a magazine. And I got

hired to run the magazine. And then it ended up discovering that actually I understood the tech things well. I did take computer science a little bit in college and I've always been an avid computer user, and it turned out that I offered value in those things. And so I ended up doing even better within an organization than as a writer, and I just discovered that was something that came natural to me, although I didn't want it to. I felt conflicted about it, to be honest. And those things just kept coming together about an appreciation of culture and then a growing set of skills around making products on the internet. And then something sparked the idea of Kickstarter.

I believe it was like in New Orleans and it came from some frustration. What exactly happened there? That's my partner Perry, Perry Chen. He was living in New Orleans in 2000 and wanted to throw a concert and was needing to front like 30 grand for it to happen. He thought this is stupid. Why can't I just propose the idea for the conference? concert online. People put up their credit cards to buy tickets, but they only get charged if the show sells out.

So it was like a conditional purchase mechanism, which later came to be called crowdfunding. And he and I met four or five years later, and he had kept sitting on the idea and been trying to make it happen, but bit a lot of roadblocks. And I had a day job with a company that had dot com and its name, and I became, you know, his close confidant and then partner on it. And for me, everything about it resonated with my own experience of how hard it was for musicians to make music that wasn't trying to be mainstream. The way that someone could be, you're going to some board to get approval, but you don't make sense to them, but the ability for you to take your own agency and do things on your

own, with your own audience, and not needing approval, creating your own approval. That was the energy that we could feel Kickstarter. was about. And before Kickstarter, you were in startups or what was it? It was like some kind of random tech startup? Yeah, they were just like a e-music, which was like a first digital music store and flavor pill, which is an email company, but sort of random things. Yeah, but Kickstarter is my first real tech experience.

So you have this idea, or I think you guys are talking about it, if I'm not mistaken, and for maybe a few years before you actually decide to jump on it. So take me to that time. Like, and what made you? Because I think our listeners, a lot of them are basically in this, maybe I want to jump and to leap into something, but I don't know. And maybe it's scary.

And I have a safe job. And should I do it? And is it in my passion? So take us there for a second. Yansi, I think it's going to be very interesting for everybody. I very much still had a day job and I depended on it. I grew up lower, middle class, kind of always been broke, assumed I would always be broke. And so the day job was

very important, very, very important. But I always had side projects that were fun. The record label was a side project. It made no money, but it was just a fun thing to do. And Kickstarter was just a fun thing to do with a new friend I'd made. And like, let's meet up on nights and weekends and let's plan this thing. And we have no idea what we're doing. We don't even know that we don't know what we're doing. And it's just sort of like a fun playing around. It's like playing house almost. But Perry was extremely real and determined about it. And Charles Adler, also co-founder, very much the same. And it got there. But the first four months that Kickstarter was live, I still had my day job. Because I was worried about losing the income and I was doing Kickstarter customer service at night.

I kind of envision it as like I had to let go of one trapeze rung to grab the next one. And I was really anxious to because we didn't have funding. I wasn't going to be getting paid, but also we could feel that something was happening. And my partners had already gone, you know, they didn't have jobs. They were only doing this. And so it was like a significant moment that I really had to edge up to for a long time and then instantly felt right, you know, once you do it. Wow. That's incredible. So the year, if I'm not mistaken, is 2009. And you're starting this, tell us a little bit about the initial journey because I think there's this, you know, a lot of these things look like an overnight success, but it takes time to raise

the money. And so take us a little bit to the early days. From 05 to 09, Perry Charles and I were working on it quite earnestly, talking to many artists, getting investors, trying to get people excited. It was a hard thing to explain. Crowdfunding was hard to explain. It was complicated. It was new. It was new. And the idea of your only charge, if a goal is hit, what will people do with the money, you know, all these, there's like a lot of things that were hard to explain that you'd just learn to get better at by, you would begin to tell when people were bored of you. And then you're like, okay, don't talk about it that way anymore. Never say that again. And so we were talking to lots of artists and getting people excited,

although I'd also don't know how much they believed it would happen. But finally, maybe five months before we launched, we had a real stable, build of the site for the first time, and we could look at it, and it felt like what we imagined. And then we began to get some of those people who've been talking to try it, just in a fake little world. But, you know, the day we launched, the first project was by Perry. The second project was by Perry and I together, quite humble. But, you know, I had hoped there would be one project funded in the first month. And instead, there was one on the third day. And it was someone that said, drawing for dollars, if you give me $5, I'll draw a picture and send it to you.

And he raised $35 from three people. But the money transacted, they were all strangers to us. And it was like, wow, this thing actually works. And ended up being in that first month, there were something like 50 projects that were funded. And you could see it entirely spread through networks. That summer, there was the first Indian classical dance project. and everyone had to ride in to request the ability to create a release, to create a project. And they would write into me.

So I wrote with everybody. We had no rules to start except no bummers. We didn't want it to feel about guilt. No guilt. Fundraising at that point was purely about guilt. There was no guilt, no charity. It's just about be excited about what you want to do and tell people. And so people would ride in.

But there was a first Indian classical dance project, raised a couple thousand dollars to go to some event. And the next week, there were like six in the same community. And you could just see, oh, this is people tell their friends, their friends say, oh, my God, this is a new path. And you could just see it work out in waves through grassroots, creative communities. And so Kickstarter's overnight success moment happened maybe three years after it was live. In 2012 was like really when it became front page news kind of thing. but it always worked. Maybe it didn't work at big scales,

but there was something about it that we could always look at and just say, oh, this is meant to be alive. There's a natural energy in this. And okay, well, let's go with it. And it built that conviction, I guess, that I'm on the right path, even if it takes a little longer.

And I think Union Square Ventures were the first investors to say yes, but take us through that investment money because I think there's also a lot of fear around raising capital and different times also, you know, create different. But again, your first time founder, you don't have the classic story, but you guys all work together. So there's a little bit of that.

So take us how that work. Yeah, I mean, we had no pedigree, no connects, really. You know, the initial funds were sort of friends and family investment, which is what funded 05 through 09. That money came from people. We knew most of those people had creative backgrounds, and they just understood the problem and were like, hey, can I help you? Some of them they offered to give us money versus we asked them for money.

So the first couple hundred thousand dollars came from people like that, and that was used to make the first version of the site and scraping by on ramen money for a couple of years through that. We knew we needed to raise more money, and everything we really knew about venture capital came from reading Fred Wilson's blog. Fred was a VC, the most prominent phase from Union Square Ventures, and he'd always been a blogger, a daily blogger,

extremely transparent, great writer, very direct, plain spoken. And we learned about startups through reading him. We had a parasycial relationship with Fred, where he was very important to us, but he had no idea who the hell we were. But I happened to know that one of Fred's favorite bands

was a band on my label. A band called Rural Alberta Advantage, still playing great band. They've gone on to do far better things than back when they were stuck with me. Great band. And Fred loved them. And I arranged it

so that one of the very first Kickstarter projects was from that band, Rural Alberta Advantage, to release a seven-inch. And I had them offer one of the rewards be a private concert in your home, you know, for like $2,500.

And then I, emailed Fred just as a reader and just said, hey, I've seen you mention this band before. They just launched this thing. So smart. They could do a private concert. And Fred ended up getting it. He backed it for that. And we had had earlier conversations with USB before that moment.

But that was how we put the product in Fred's hands. And, you know, USB ended up and Fred led with us a few months later. And Perry really built that relationship. What was interesting is that for years, people, had just turned us down and thought what we were doing didn't make sense, and artists are starving for a reason, something a VC once said to me, and we really had to fight uphill to make the case. You know, it wasn't obvious at all. And when we sat down with Union Square Ventures, they listened to us for five minutes, and they were like, okay, we believe your thesis, why you? And like, no one

had even believed the thesis before. But when USV agreed to invest, we said to them that we wanted to make an independent company and that we weren't trying to IPO, we weren't trying to sell, and we wanted to make something that was independent long term, and for them to be comfortable with that. And Fred agreed, understood, saw the vision. And Fred's still on the board of Kickstarter. We worked together today on the board of Kickstarter. He's been an amazing steward and advocate for 16 years at this point, great human. And a lot of what allowed those doors to open, honestly, we're having other people vouch for us. When you're not connected to anything, it's like a ladder vouch system that happens.

For example, when we were trying to hire developers, we kept hiring poorly because we didn't really know what we needed because we didn't know what we were doing. And then we met someone, someone named Andy Bayo, who was experienced and had made companies before, and we had a mutual friend. And Andy talked to us and heard, oh, these are like good people. they're little out of their depth, but it's a great idea. Let me connect them with somebody good. And so he introduced us to someone named Lance Ivy, an amazing developer,

who instantly all of our struggles were better, and Lance was our principal architect forever. But for Lance, we could have randomly emailed him, and he might not have responded, but he needed Andy to say, hey, what they're doing is interesting. You should talk to him. And similarly with investors, there's a woman here in New York, Sunny Bates,

who's connected to everybody. And we met Sunny through a friend of a friend, and soon you're getting the Sunny vouch everywhere. And we all really depend on those sorts of referrals. And it's a real leap of faith, right, for someone to say, hey, you are a, I like your energy, I like what you're trying. I don't know if you're going to succeed,

but I'll help you out. And without those sorts of people, we would have faced a much tougher road. And all of that, it really allowed us to always be working with people who we were morally aligned with. I don't think we've ever felt misaligned with a core partner to us at Kickstarter. And part of it is you could say it's a good fortune to work with good people, but I also think it's because it's all operated through a network of, I don't know,

that was kind of earned. And I want to say something to people or the listening. I think what you shared right now, and you call it Ladder of Vow Systems, which I didn't hear before, which I don't. love. And I think there's two sides to this, right? One side is the person is asking for help, right? Whether it's intro to a job or intro to a startup or intro to investors or intros or whatever. And first of all, just understand that whoever is vouching for you actually is taking a stand for you and their reputation is on the line. So really just be really mindful

for that. But also make sure to follow up and think them and all the things, right? Like make sure to do this right. I think there's sometimes we miss that, Yanty, and I think the reason why you guys probably got a lot of these introductions is because you probably navigated this in a good way that actually makes people say, okay, I want to vouch for these people. Because I think this sometimes we take it for granted or we make it hard on people to help us, right? Like we do some of these common mistakes that I see. And I think today, because everything is in the hidden market, or most opportunities are in the hidden market, and who's going to help you, who thinks about you, you know? And anyway, I just wanted to make sure this is so clear because this is so important.

Yeah, I think the mistake it's easy to make is to, you want to project that you should be taken seriously, so you try to show you have all the answers and you've thought of everything. and I often have that desire. What that ends up often doing is it presents sort of an enclosed box where it doesn't offer ways in. It's like you're trying to answer every question before it's asked of you, but then it just, there is no conversation. And instead, I find that when you show up in a place that's very genuine, and genuine means good and bad, Genuine means confused.

Genuine means open, curious. I find that you can have very different types of conversations. And I used to be consumed with the idea, and I mean, I still struggle with it, of viewing a conversation as a venue in which to prove I am right, rather than viewing it as an exchange. And the more real and honest, I'm able to be in that exchange, the more will come from it.

And when I try to answer every fear or every anxiety I anticipate ahead of time, you just block the entire exchange from happening. Because what the other person receives is like, whoa, this person's kind of spazzy and a bit closed off. And I don't even want to ask because that was a lot to listen to their first answer. So like, nice to meet you. I'm going to keep going on the cocktail party. It happens every time.

All the time. Right? But if you're just softer, and more open and not trying to, you know, just whatever, let what's inside reflect out. It's very different. We need to pause for a super brief break. And while we do, take a moment and share this episode with every single person

who may be inspired by this because this information can truly change your life and theirs. Now, I want to check in with you. Yes, you. Are you driven, but maybe feeling stuck in your career or a fraction of who you know you could be? Do you secretly feel you should have been? and further along in your income, influence, or impact. Do you ever wonder how to create not just a paycheck, but the life you want with the paycheck, the thought leadership, the legacy, the freedom?

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get 20% off with a code leap at working genius.com. That's working genius.com. You'll be glad you did. So I wonder, let me ask you before we move a little forward, how do you navigate? Because on one hand, you need to sort of fake it till you make it. There's a little bit of that, right? You need to be confident. You need to at least show up like you know what you're talking about or at least somewhat, right?

But then, and you can't show all the fears. You can't be completely authentic. Like I think there's a little bit of a myth of how authentic you can actually be, especially when you're running a startup. There's going to be a lot of ups and downs. You can't show all these emotions. But on the other hand, I love that idea. The more like you're close off and you show up as if nobody can help you,

nobody's going to help you. So how do you navigate these two? Well, I think sometimes the way to be helped is to struggle and to not know what to do. And that sometimes you're going to ask for help and people are going to say no, and that is helping you. Because you can't learn this.

You can't get someone to help you with whatever's happening. So in some ways, you show up and you're too closed off and you blow the situation. There's a way I should think, oh, that was meant to happen because maybe you were going to do that

in even bigger stakes later on and you just saved yourself because you did it in a place where it stings and you feel embarrassed, but guess what? Like, it's not fatal. And there are days, definitely if you're in a lot,

entrepreneur, there are going to be days where it feels brutal. And you can try to smile through it and it's hard and just know your thing probably is it going to resonate the way it will on another day. It's like a bad hair day. But maybe there's weirdly an opportunity on those days to somehow be more real. And maybe there is, maybe there is something to be learned. But in general, the way I would think about it is you just try to express what's genuinely exciting to you. What's exciting? What's interesting to you right now, don't tell the whole story. Share the nugget. Share the 30-second version. You know, lately, I'm just thinking about this. I think this is really interesting. Stop there. And let someone else talk and just see where it goes. And if someone makes a suggestion,

and even if it's something you've thought about before, don't be like, oh, I thought about that. And let me tell you all the things we're doing. You could just say, that's really interesting. That's super interesting. Just listen. Just engage. And it's a great way to bring people in. I mean, anytime I'm meeting with someone and wanting to talk to them about my project, I normally spend, I would say I make sure the first 60 to 70% of the meeting time, like if it's an hour meeting, then like up until minute 35, we're exclusively talking about them. Really? That's incredible. I'm just being curious. I'm just being curious. How are you seeing the world right now? what are you thinking about?

And what you hear in that is you will hear ways for you to connect with them. You're going to hear, oh, I'm really concerned about this, I'm thinking about that, and you're just being generous. You're just being generous. It allows you to be less centered.

And then they're going to feel a debt. Like, oh, shit, we were supposed to do my thing. We just did all this on me, oh, my God, I feel so bad. That's great for you. That's great for you. A debt is great. And then you just talk about what you're doing

and you don't hard pitch it. you just soft intro it into the conversation. It's contextual, it's natural. And if it feels like, oh, we were rushed here, there was more to talk about. We should talk more later. Phenomenal. Great. That was your only goal. Going into the call, your only goal was to have another call. You just got it. You could say it's a strategy. To me, that's just genuinely what I find compelling. I know what I think. I'm interested in what someone else thinks. But like, there's a way that, you know, when someone vomits their pitch at you or comes at you in a way that it's like you can feel the intent, it's such a turnoff. And it's like someone is really beating the

odds to get any sort of connection through that. This is powerful. I loved what you just said. Anyway, stealing that one because I think the whole idea is how do you understand what's on the other person's side. Like, how are they seeing the world, right? And they have their own lens on what their frustrations, what their goals are, right? And the more you know, the more you can navigate whatever it is that you're going to talk to them about anyways. Yeah, you can very contextually mention, like earlier when you said this, this is like that. It shows you listened, it shows you cared about them, and it also makes what you're doing relevant to them. Amazing. So, first of all, we got some incredible nuggets here.

And take me for a second to 2012. Something makes Kickstarter BASI blow up. And a little bit of what happened and how does that change you or build you? Tell me a little more. At 2012, the site was three years old. We were probably 30 employees here in New York. And it would have been steadily building. They were beginning to be the first, like, tech gadgets on the site.

and the first video games on the site. So like the level of complexity and the scale of budget of what's happening is changing. And there was a single day, February 9, 2012, when the first two projects both crossed a million dollars

on the same day within minutes of each other. One had just launched the night before and the entire internet was like refreshing, watching it together and ended up being like international news. And there were many, many, many things happening around us that very same day. I remember that day, Chinese state TV was at the office. Bloomberg talked about us at City Hall for something happening with New York. It was just

like a, whoa, what is going on kind of moment? And once the story was out there that there was a website that could be like a million dollar lottery ticket if you have an idea, we began to get flooded with projects. And we'd always reviewed everything that came through. And now our review systems were getting overwhelmed with so many things, and a lot of them low quality, and really kind of changed the relationship of the company to its community a bit, where up until then, it's very cozy.

There's a sense that we knew each other. It was a relatively small, contained community of people, and then suddenly it was like anyone who wants to make anything views Kickstarter as an important outlet to think about. And so what had been a site that really was driven by small groups of people instead became driven by product marketing and Instagram ads and something that felt more like traditional consumerism. And we ended up very controversially trying to get in the way of it. And there was a point during that year when it just kept building and building. And we made this out of an hour post called Kickstarter is not a store announcing a bunch of rules.

to make it harder to release projects that were more like products. No 3D renderings. He must show a demo. Like, you must answer risks and challenges. And just trying to temper the enthusiasm. And it was a very unpopular post and decision. Had 500-some comments that first night. Most of them were kind of angry.

And that did not, by any stretch, solve those issues on their own. But I always felt proud of that as a moment of really trying to navigate from what was important to the reputation long term, being willing to make a sacrifice. Yeah, and I think often with companies or public projects, I mean, personally too, but acts of sacrifice,

I think are really important. You have to give up something to get something. You don't get to just keep getting. And for us to be able to say, okay, we're not going to pursue unlimited growth in this, and like, that's not what this is. But what you get is you get more trust and integrity, a sense of integrity. It's an ongoing battle.

Like integrity is a bank account where you earn or you spend trust is sort of like that as a brand. It was a key moment in our values and our soul to make a hard choice that wasn't financially driven at a moment like that. How do you prepare yourself to combat these kind of things or to be a mindset that takes you through? challenges, like how did you grow to be able to navigate some of this? Or how did that impact you? I mean, it was a struggle. There's a friend that's constantly with you of anxiety and doubt and comparison. You know, it's not a very nice friend, but it's always there. And you can't kill it. Pretty cool usually, actually. Yeah, but it's just there. Like, I don't know how much you can do with it, but I think you have to learn to contextualize it and see that it's not real, that it is your fears,

but that it is not real. But that's a hard thing. I mean, it's taken, it's much later now that I have a better sense of it. And I know I only have a better sense of it up until a certain boiling point. But beyond, at a certain level of scale,

yeah, I'm sure I'll revert to being a crying baby in the fetal position again. But yeah, I mean, I think there's a lot of doubt, a lot of looking around and feeling like you have to do what other people are doing. If you're not doing what they're doing, you worry you're broken, a constant reversion to being mediocre is like always there as a temptation, always feels like the right decision is just to become mediocre like everybody else. I think the way

you bounce that, one is through a personal practice of caring for yourself, which I got much later, but the other is to have, you know, partners so you can talk about it with, both professional partners, life partners, whatever. It's like these are hard things to hold on your own. And it's very helpful to have someone who's a sounding board, someone who can tell you, hey, I know it's not easy, but you're not crazy. And, you know, there's other days you felt the opposite. And those days were real, too. And like, you know, you just got to get through this one. And most of the time as a leader, the right thing is to, like, just not do anything. Don't react to your emotions. Your emotions are temporary states that solely exist within you. Reacting based on your emotions is always going to be a

bad idea. And the right answer most of the time is just to sit with it and don't be rash. And you have to act at some point. But our emotions are a guidance system, but they should not be a directive that we immediately respond to. And as a leader, that's very hard because, again, you have anxiety of competition, worrying about losing market share or place. And so this is where you get companies that have product roadmaps that never stop changing. You never stop chasing in the shiny object. It all comes from these fears that as a leader,

you don't know how to manage and it just creates a thrashing around that's kind of embarrassing, but it's really hard to manage on your own. Oh, this is so powerful. And it's interesting. I just had a conversation, actually yesterday on the podcast

with somebody that said, don't make run decision on the uphill. And there's something there, right? Like when we're down in the leadership route, right? And something is really, really hard. This is not the time to make some rash decisions about how the company is doing, right? You're going to have to be in a better spot for yourself. But I think sometimes you talked

a lot about that mental penalty, I guess, that we all need to pay a little bit. And I think it is important right now to talk about it. And it's going to go also well into what you're working on or some of the things that you're working on today, because I think more and more people will be kind of their own entrepreneurs, side hustles, the portfolio careers. There's going to be a lot of more creators. There's going to be a lot more independent people. So we totally believe in Leap Academy that there is going to be an entire fluctuation of people

doing their own things and portfolio career. And that means a lot more people need to cope with being on their own. And that's hard, right? And again, you can have coaching and you can have the mentorship and you can have the people by your side. But at the end of the day, you're stuck on those mental stress, I guess. Yeah, that doesn't sound fun. I agree with you that the trad life of I have a company and I have a consistent team I work with

and I have a great boss and, you know, I'm going to be here at this company forever. Yeah, that is dying. even what work is is really, really changing. People needing to demonstrate and find their own agency and skills and how they can be useful to other people is important. I still believe it's critical to do that with others. I think doing something with other people, I mean, there's some practices.

The practice of an artist is a solo practice, but doing things, operating in structures in which you have mutual support, in which you are dependent on each other, are really healthy things. They would make things fun. My company project now is called MetaLabel. We make projects that help creative people cooperate rather than compete. And we are a small studio team, and we make sort of distinct projects that we put out one after the other.

And we are now four people. In the past, we've been 11 people. But now in the AI age, we are a partnership of four people who are each able to act with extreme agency running out in each of our directions as we wish. And we are here for each other. We are deeply emotionally tied to each other. We are philosophically, strategically aligned with each other.

Our work builds on each other. The things that we do together are way bigger than anything we could do individually on our own. And yet we're held together in sort of a looser, slightly less formal configuration than maybe we're used to. And it's shocking that four people are doing the work that in the past might have been a 100-person company. There definitely is a different world that we're in. And I think it's crucial that we navigate that with others. And so everything I've been making the past five years has been about that.

So let's talk about it because you left the CEO role in Kickstarter. 2017 and you're involved with multiple things now, I think. And I do believe, just before you go into some of the details, I think is really important because it is community. I think there's a reason why Leap Academy, I think I thought it's going to be more about the coaching and the engineered process. What it actually became is more around the community and kind of the movement that we created of like-minded people that are helping each other.

with the coaching and the union process and support and all this, but it's actually the community that holds, you know, the tide lifts, whole boat. So right now, talk to me a little bit about some of these, you know, you talked about eight corp and you talked about some of the duck forest. Talk to me a little bit about why is that your passion? Let's start with there. And how are you trying to resolve it? Because it's all very aligned.

There are going to be more creators. There's going to be more people that are exactly where you are helping out. So talk to us about it. I mean, I don't even, in a way, don't even know where to begin, but I'll just say this feels like a real breaking point of a way of the world is ending, has ended, a new way of the world is beginning. You see that online.

Online, what we thought social media would be, place to connect in like these great human networks and the globe all coming together, largely destroyed. Now it's advertising, it's bots, it's places to gain power. There are tools of power. Social media is a tool of power.

our expressing ourselves creatively, super important, growing. 48% of Americans have an active creative practice. Yet all creativity is dependent ultimately on some tech platforms that determine everything about how people are paid. And yes, people have more agency in some ways, but actually they have not a lot of agency in even more important ways. Like as a musician, you're very limited in how

and where you can, say, sell your music by just what the market is. And so it's just a larger, fracture, larger things happening, reshaping, reshaking. And there's two projects that my team, metal label that we are focused on this year, both extremely ambitious, both trying to address this in different ways. First is a project called Artist Corporations. And while I was the CEO of Kickstarter, we became one of the first public benefit corporations, a PBC or a B-Corp. And these are corporations that are pledging to do more social good. And so with Kickstarter, we were one of the first and made pledges about how we'd use

our profits and the way we'd support artists. And the company still operates according to that. And it's awesome. I was seeing ways that artists and creative people are not currently served in the economic system. As one example, artists don't really participate in capitalism. Like platforms have equity and shares and capital markets and ways that they can build exponential value and growth.

all an artist can do is just sell their product as a commodity that other people then speculate on in markets. And the artist doesn't even participate. And so all these ways that artists were disadvantaged and were like rounding errors in a system that wasn't meant for them. So for the last year and a half, we've been working on a project to draft legislation and to create a new law and a new corporate structure called an artist corporation, an ACorp, which is a legal entity, reserve design for artists and creative people, that explicitly protects artist rights and creative rights are explicitly protect as a part of this, that allows you to create stock

and equity with the check of a box and say, okay, we're now partners, we all have shares in this thing we've made that has way more sophisticated IP ownership rules than we've had today, and will allow A-Corps to pull together to get healthcare access. So as an artist, this can be a path towards healthcare. And so we're working on this law.

The first place that's being proposed is Colorado, It'll be getting proposed there any day now, and we hope to have a law passed in at least one U.S. state this year. This is a very long-term project. If this work succeeds, this is like a centuries-long type of project. And right now it's about drafting the first statute, changing the way people look at artists and creative work as real work. And then we have to bring investors in who are excited to put money into it. We have to create operational and financial tools that help artists learn better how to manage their work. money. A lot of that I think could be achieved through, you know, dashboards, things that we can build

for people. You know, the artists of the future are going to need COOs and like a different way of operating. It's a whole new way of thinking about what a creative practice can be. We've created the Artists Corporation's Foundation, a nonprofit to lead this. It's exciting. Artistscorporations.com if you want to learn more. And maybe Yancey, let me talk about that one for a second, just because I vaguely heard, I think, like a mini TED talk that you did or whatever it was. And I thought some of the stats there were fascinating. If that's okay, if I quote you on it, it basically said, if I'm not mistaken, 85% of the visual artists make $25 a year. Less than 25k, yeah. Yeah. I was just like, did I hear it correctly? So first of all, it was fascinating. And then you talk about the future,

basically like how AI is making everything worse, right? Because now you suddenly have all these, like, ghost songs, right, that suddenly, you know, don't need any royalty. So now less and less people want to buy, you know, and pay the artists. So now we're literally starving this whole mechanism. So when I listen to that, I was like, oh my God, like, I don't even know if I realized that. So I just want to make sure the listeners are hearing it because I think you say it a lot better than I did right now, but it was like, it was alarming. Yeah, there's a TED Talk you can watch where this was introduced. Yeah, it's really trying to think about creativity is growing and spiking. The time spent on creator's output is growing. The amount of money going to them is growing, but yet they're

operating without any real infrastructure. And if we take this work seriously and think maybe this is the future, our economic future, then actually it needs a much stronger foundation than it does Now, it needs things like equity. It needs more templates and forms that allow it to get access to money, right? Because it's very hard to do that today. And the way you address a change like that is at a deeper structural level. And so it's a long-term project, but very much believe in. And then the other focus of metal label is called the Dark Forest to Operating System, or DFOS.

D-F-O-S.com. And DFOS are shared private internets. So it's a space where you and a group of people, it could be a community, it could be a group of friends. You have a private desktop operating system that only you all can see. And inside has apps. It has a chat app with a group chat with different rooms. It has a post feed, a private post feed where anyone in the space can post like a substack, Instagram, tweet into the same feed together.

Posts in the post feed can leak out of your closed space if they get enough. upvotes. It has a built-in treasury inside so that people can pay for access and that money can be used together by the group to do things. And it also has an app store where you can install your own apps within your dark forest space for you and your community to use, or you can make your own and make something that's custom for just you and your group. You can even vibe code it, prompt it, and it will make the app for you. And so defauses are these shared private internet's where every space you go in looks different, has a different desktop, different field, different purpose. And, you know, our feeling is that the public internet is pretty cooked.

The public internet is ruined. The private internet is where people are their real selves. And this is the infrastructure, the OS, for the private internet. Just this week, we had our very first space sort of leak out. It's still private, but 160 people or something have found it in the last two days and are chatting away. And this would be gradually expanding and then doing a wide release in the spring. So dfos.com. And so this, this is imagining, yeah,

the internet has made us alone, like social media has isolated us. We use group chats to be connected. Like time on phone and group chat is healthy. Time on phone, scrolling is unhealthy. And so we're just trying to make the space where you can have fun and take the parts of the internet

and social media that are interested. but yet do it in a safer way with just people you know. I love that. And by the way, I do think that the pendulum of, you know, it's been only friends and now it's like everybody, the social media,

like you said, is completely like interest-based. There's no friends. It's like only influencers. And now it's going back into what we are feeling is like also like it's all back to community and how people actually get to know each other, help each other,

because at the end of the day, we lost it. So I absolutely love what you're doing. I'm definitely checking it out for Leap Academy as well. But what would be one thing that if you met yourself earlier, like if you needed to summarize, what would be one thing that you wish you knew earlier in your career? Well, I think I've always known what I needed to know. And I believe in learning through pain.

You know, there's still like an email exchange with someone from a year ago that I keep. thinking about because I messed it up. It keeps stinging. And the mistake I made in that email, I will not make again, but it's like, I hate that that happened. I needed it. I believe that the universe is always working towards you to fulfill your destiny, but your destiny involves pain and struggle. Like that is the way through. So I do not wish to skip that. But I think at my most regrettable moments, I was just really concerned with people thinking I was smart. You know, I was concerned with wanting to win a conversation, and I was more of the closed box

than just an open heart. And I know that came from a place of fear and wanting to be protective, and I look at that person with compassion. I absolutely understand. And one of the things I'm just so grateful for is to, both through accomplishment, but also just maturing, no longer having such a needy ego that's looking at things in that kind of way. And I encounter people all the time who I can see have that same affliction. And all I wish for them is, you know, oh, I just wish you could just let go of that feeling because it gets in your way. You actually don't need it. The fact that you think you need it is what makes you need it, but you don't need it. I would want to give myself that grace, but other than that, all the mistakes were necessary. And there's many more to come.

Which is depressing, but also beautiful. Tell me about it. Yancey, so summarize for us, where do we find you? So Acorp, Defos, where are the best ways that all listeners can reach out to you or to the beautiful things that you're involved with? What is the best way? Yeah, three websites, defos.com, D-FOS.com. You could sign up for the waitlist.

We'll be letting people in, not too far from now. artist corporations.com. There you can learn more about the bill. We'll also be opening at Defos for A-Corp, so a place where the artist community can get together. We'll begin planning and talking through what's going to happen with legislation through there. And I personally am at Y-Strickler.com,

first initial last name, Y. Strickler. And you'll find a whole lot of black and white and text on a page with no images anywhere. So if you can accept just the bruce brutality of I read about how no one reads anymore. Well, my website's a real failure. So go, go enjoy. Can see, thank you so much for the time for the beautiful conversation. I took so many notes. And thank you for everything that you're doing. I absolutely love it. Thank you for the invitation. I appreciate it. What an incredible conversation.

Like, honestly, I had no clue. We're going to get so many nuggets. We learned about thank you. and making every conversation as much as possible about them, not about you, so that you can find ways to connect. We also learned about closed box versus open box. And I love that. It's like how this may be taking away from people being actually able to help you. This is so powerful to really understand it and really honor the ladder the latter of vouch systems, which I love that, you know, that verb. So now we get to choose like a question. first of all, if you liked it, please share it, like, subscribe, download, all the things. Seriously, I don't ask from you a lot, but this actually really, really helps us continue the

show and bring amazing guests. So share it with as many people. Plus, when you do share it, if this can actually help them open more doors, be more successful, get the courage to chase their dreams, let's do that together. This is how we make the world a better place. Okay. So now to our question, to our weekly question, So we're looking at our YouTube channel. We're looking for your comments. We're looking for your questions. And Skylie is asked about what are some of the best ways to open doors.

Such a beautiful question. And we chose it because it's so relevant to this conversation. The very first thing that we kind of talked about is, first of all, really, really understand their why. So basically, there's going to be five steps. So the very first thing is really understand the person's why. like what's important for them, right? Why are they doing what they're doing? And try to not only think of like the 30,000 foot view.

Oh, they're running a group or they're running a company or they're a hire manager. Like don't think of just the title, but why is this important for them? If they posted something, why was this important for them? If they won some kind of an award, why was this important for them? Like what drives them? What motivates them? what would be some of the ways to eventually, like add value, right? So you want in that case to research as much it possible.

If needed, ask around or ask them. Again, if you're in the conversation, stay curious, like as much as possible. Get that information. Then what I want you to do, number two, is how do you rise above the noise? So if this is a hiring manager, if this is a CEO, if this is an investor, if this is whatever it is, right, that you're trying to reach, influencer, whatever, most people don't even think of them as humans, they just try to get something from them, right? If you can find a way to rise above the noise and do something a little different, right? So first of all, you're going to

use, we talked about in one other podcast episodes, we talked about the hook story offer, right? Make sure to create very short hook to grab their attention, but also how do you create, number three, a win-win? How do you really find a way for you? you to give value to them, not just ask for something, right? It really honor their time and their reputation. If somebody's giving you, if you're asking for somebody's time, you better know why it's worth it for them. People can't give the entire world 15 minutes or an hour every time.

Like it's just impossible, even if it's like 10 minutes each. They just can't, right? So the more people pile there is, the harder it is to give so much time. So really figure it out how do you honor their time? But also, if they're going to put their reputation on the line for you to make an introduction, you need to understand there's a cost at stake. Like, there's a lot at stake. Like, if you don't behave, if you don't deliver, they're putting their reputation on the line.

So really understand that if they don't feel like they can vouch for you, that's okay, right? So also understand that. Like, there's a lot at stake. Now, number five, just make it really, really easy to say yes. super easy for them to say yes. If you want an introduction, create like a little paragraph, extremely relevant that they can just copy paste. If you're trying to like, you know, reach out to someone, like make it simple. Like, you know, just really make it easy. If you are reaching out to someone, the ask should be so simple for them to say yes that it's like slam dunk, right?

So make it easy to say yes. And that's how we win big time. Again, share it with everybody that you can. And if you want to do one more thing for me, if you're on Spotify or an Apple, whatever it is, if you can put a five-star review on the podcast, on the show, it will literally mean the world. And it makes it so much easier to bring so many amazing guests. So thank you, everybody. Have an incredible week. And let's go chase some dreams. I'll see you soon. Remember this episode. It's not just for you and me. You never know whose life you are meant to change by sharing this episode with them. And if you love today's episode, please click the subscribe or download button for the show and give it a five-star

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