How to Take Bigger Business Risks with Chase Jarvis

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0:32I can't wait to see you there. Welcome back to the Jasmine Star Show. I could not be more excited. Can you hear it in my throat? Like I kind of feel like there's this like nervous, excited edge because the person sitting across from me is not just a brilliant entrepreneur. He is not just a successful author. He is not just a kind, brilliant, creative human being. He is here today, here to guide us to talk about more than anything our inability and lack thereof of playing it safe. He believes that we should never play it safe. Ladies and gentlemen, welcome to the show. I could not be happier to be here.

1:12Chase, okay. Sorry, I just blew the audio guys. I know. But that's real. You can't hide that. So what people really know about my recent entrepreneurial journey looks a certain way, but you and I go back. And so what I want to do is I want to frame this podcast in three sections because I do believe that sometimes it's easy for speakers, for authors, for thought leaders to come in and present an idea and people are like, okay, cool. But what I want to do, because I have a very unique vantage point is I've seen it all, man. Like I've seen it all from the backseat. And likewise, I've seen you. I've seen your journey.

1:50And so I want this conversation to be super real. I want it to get ugly. I want it to be beautiful. I want it to be messy because that's what building our businesses has been. And so breaking this podcast into three sections, it's like when we first met, when I started learning your philosophy of not playing it safe in life, then I want to move into business iteration. You and I started building different businesses around the same time and like strengthening the muscle of not playing it safe. And then we're going to get into a conversation about what that looks like for you right now. Like, why are you so passionate about sharing this message at this point in time?

2:22I love it. Okay. So let's go back. Everybody loves a good framework. You know, I mean, you know your girl. I only think of frameworks rather. Like this is how it just, it is. And it's like, you're super creative. And our little artsy brains, they go all over the place. But if we can have a couple of like nice little sandboxes to play in. Thank you. Yeah. I love it. A little structure. A little structure. A little structure. So let's go back. And the year is 2010. Okay. 2000. Okay. And so I get a phone call. I'm younger then. I'm better looking. Aren't we all? No, no. You age like fine wine, brother.

2:53You age like fine wine. Four hours of sleep, people. Hey, I know. We're recording in Austin. He flew in from Seattle. His flight was delayed. Didn't get to his hotel. It's like 2, 2.30 in the morning. And at the time of this recording, it's about 8 in the morning. So he is looking just fresh and clean. Let's go. Let's go. See, we're not playing it safe. That's what we're not doing today. We are not playing it safe. I love your framework. I think it's a great, yeah, great setup. And that's what I want to do. I want to just have a real conversation. I want people to get a front row seat to like the ick and the climb of a good journey.

3:25Great. So it's 2010. 2010. More or less. And I get an email from somebody and they said, Chase Jarvis would like to set up a phone call with you. And a quick Google search reveals like who you are. And I'm like, whoa, this guy is legit, legit. What is he doing calling me? and can we explain the story on both sides around that conversation? So my phone rings. Okay. Okay. Me first. No, actually, you know what? I'm going first. Okay, good. Please. I'm going first. It was 2010 and we had just started what was essentially an experiment in online learning. It's very difficult to go back this far 15 years ago now, 14 and a half years ago, and think that literally online learning was not a thing.

4:07Yes. I had a podcast at the time. I just started it in 2009, which was the first, essentially one of the first 10 interview podcasts on the internet, which was very strange to even be saying that now because now there's, you know, a hundred million or something like that. Back in my day, kids. Totally. It sounds hilarious. This is the story for today. But the year was 2010 and we had just started essentially an experiment that I had been building a large community in the photography space. And myself and a partner had this idea that the future was going to be about being able to learn from people that you admire and respect from anywhere in the world.

4:45And the internet was going to do that. Really pause though, like for the gravity of this, because like you said, it's really hard for people to understand like 14 years ago, when we just pick up our phone today, we forget that Like that didn't exist. Like online education. Did not exist. Did not exist. Specifically, it did not exist in a video or a streaming capacity. And so it's like, you guys, 14 years is nothing. And it's so everything. It's a thousand years. And so when you say it's an experiment, I want to take people back to that. It didn't exist. We had to create our own payment system, our own video system, our own audio recording, our own streaming files.

5:20Like we literally had to do everything. We essentially, there was one system out there that was built for military to talk to their spouses overseas. So we basically hijacked that and morphed it into something that we could, the way we tested this thing was I had a photo shoot and we just put cameras up and broadcast to my community. Hey, I'm doing an album cover photo shoot. If anyone wants to watch, you can just see how I operate. 25 ,000 people watch that photo shoot live. And we were like, oh, this is actually a thing. So what if we could build a platform where this was the norm? Okay, let's pause because I just don't think that, okay, the storyteller in me, I look at this and the podcast host in me has done you a disservice because what you said is, so I did a shoot for a band.

6:09And so let's pause for a second. Chase was and is one of the highest regarded photographers and cover of Newsweek, builder of apps, writer of books, photographer amongst stars and athletes and major campaigns. And so I didn't say that thing. And so we talk about building community. There was like, and this is what I want people to know and believe is like, there's part of our story. And when you bring people into that, you build people who are like, I care about the thing you care about. and what you were really good at and very early to see is anytime that you could share information with people, they in turn became devoted, not to you, but devoted to this bigger idea, that community that we can learn together.

6:46And so at the time, like you guys, like let's go back. At the time, there were photographers, there were creators, there were authors, there's all these big name people who lived in silos behind these magic Willy Wonka castles. And what you did is you said, I'm going to turn the castle inside out and I'm going to share all of this information to all of y 'all. And so what you did as an experiment it costs you money. It costs you team. Sounds like I'm crying. I'm so moved. I'm so moved by the spirit of creativity. Okay. And so that's right. So you already said amen. That's right. And so then when you say, let's have this experiment, I'm going to broadcast me shooting and it's just, we're going to try this.

7:22We're going to do something that's never been done. And 25 ,000 people watch. And then you're like, ding, something's here. And so I really just wanted to parse it out before we like really put the gas in the story. It's very hard to articulate. And again, I don't want to, I think we don't want to reference back to that too much, but that was everything that you said was true that didn't exist. Right. There was no such thing. I mean, hat tip to Gary V, but I had a full-time video person following me around starting in 2005 with the goal of telling stories about my journey of becoming a photographer.

7:51Because when I went to learn, there were no resources. Right. there's a bit in the book where I actually went to the library and flipped through card catalogs and checked out books about photography because there was nowhere else. And when I would try and introduce myself to other working photographers, that was very secretive. So it sounds like a foreign language when we're saying it now, but that was the norm. And to me, there was an opportunity to help other people learn. And to me, that's actually, I think I can say my photography is world-class. I've done, you know, literally hundreds of campaigns for Apple, Nike, Samsung, just massive global campaigns, hundreds of them.

8:30And yet I feel like what set me apart as one of the early people in photography and a pioneer was specifically sharing, yeah, sharing my journey, not just the good stuff either, sharing my journey on the internet. And so with that as the backdrop, yes, thank you. Yeah. With that as the backdrop, that's what we sort of leaned into with this experiment. The year before I had launched a photo app. It was the app of the year on the Apple iTunes platform. This was late 2009. And it was the first app that used photographs as the basis for a social network. And that went to number one. And it was essentially Instagram is a lift and stamp copy of what was called best camera.

9:13And there's great footage somewhere on the internet and the way back machine. You can find find the Instagram CEO at the time talking about that. And I learned a lot about creating a business in that moment, because when you go from nothing to, you know, the number one in the app store, there's all kinds of challenges. And that's also well chronicled on the internet, but I felt like I could leverage the experiences from that into this new experiment. And my mantra was to move fast, was to experiment and, and bring the community along for the ride. Move fast, experiment, bring the community. So on the back of your success career, on the back of knowing that sharing information, on the back of broadcasting something as an idea, on the back of building an app, on the back of growth and on the back of the peaks and valleys, you're then like, hey, I have this idea.

10:05And when it came to finding who you wanted to bring in initially, how did I come in the mix? Well, our first class was a commercial photography class and it had 50 ,000 people. And it was, I mean, that absolutely blew our expectations out of the water. And a certain percentage of those people, the business model was very simple at the time. It has since morphed. And this is a long, long journey. The company was actually acquired by a big public company, etc. but essentially anyone in the world could watch for free. And if you wanted to be able to watch it again, then you had to pay for it. And it was roughly like 150 bucks or 200 bucks or something, which was totally transformational because you used to have to fly across the country, spend$5 ,000 for a long weekend with your hero mentor, et cetera.

10:45Our first class had 50 ,000. Our second class had a hundred thousand. And both those were oriented around more of the commercial photography that I was doing at the time. And I knew that wedding photography was massive and that there were people in that area of the industry who were shining stars. And one in particular, whose name is Jasmine Star, was really interesting to me and my partner at the time because you were doing it differently and you were bold, fearless. And I think you and I both know that while both of us were bold and fearless out on camera, we were terrified and Yeah, and stupid.

11:23And stupid and curious and terrified and worried and all those things. But it occurred to us that the wedding universe was a big universe. And what could make this interesting? And we had this basic framework of if we could take someone that we truly felt was dynamic and at the leading edge of their craft and put them in an actual wedding, that that would entertain and inspire the internet. the photographers around the world who wanted to learn a little bit more about that. So the market was big. The talent was raw and real and the opportunity had nothing like this had ever been done in the history of the world.

12:03So we essentially put those in a blender and, you know, we had a very short list of people and I actually, I knew numbers two, three, and four on our list and didn't know you. And so I had, I don't remember how I actually reached out to you, but. I do. Can I take us back? Yeah, please do. Okay. So I get the email and it's from somebody on the team and they explain who you are. They asked if we would be able to have a conversation. And I said, yes. And they said, we would like to have a conversation as soon as possible. And it was a weekend. And I said, yeah, we'll have this conversation. And so you call and I hear a lot of ambient noise in the background.

12:40And it sounds like you're outside and you're like, please forgive me. I'm at a barbecue. You're at a barbecue or are you at a party or something like that? I remember. And we have this conversation, it's maybe 10 or 15 minutes and you don't even go into the size of the production of stuff that you've done. You don't go into the background story. You just say, okay, I have this crazy idea and I want you to be a part of a crazy idea. What if we had a live wedding and you shot it on the internet? And like my whole frame of reality just right there broke. I remember sitting, we had this con, it was like our first condo ever.

13:16I'm sitting, we have like very little furniture in our house. And I'm just like, I couldn't even my mind. I was like, and then on the internet, I had no frame of reference whatsoever. And then I was like, let's do it. I think I gave it like maybe 30 seconds. And I was just like, I don't know who this guy is. He's freaking crazy. And he's my kind of crazy and all in. Like, I didn't think about anything else other than like, let's do it. And you're like, great. I'm not the team. We're going to draft up some contracts. We'll explain more things. And they're like, great, cool, blah, blah, blah. And that was it, dude.

13:46Yeah. We went all in. Like we literally went on. It was like this arranged marriage. And so what was I class number three? Yes. I was class number three. Yeah. So. And I will say that 150 ,000 people watched that live wedding. 150 ,000 people. And the crazy thing is it's hard when we like, let's go back to 2010. Like this is like, even before Facebook was available to people that were not in college. So the main social platform at the time was Twitter. And when we shot this live wedding and 150 ,000 people were watching, we were trending on Twitter. I have great screen caps. I mean, Jasmine star wedding, Barack Obama is right behind you.

14:26And Lindsay Lohan, you know, it's like, you know, you're in good company. It's like me, Barack and Lindsay back in 2010. And so like that whole thing was so, so, so transformative. And we're not going to get into the details of that. Sure. But what I do want to highlight the format. It was a five day course. Yeah. That was a lot. That was a lot. I mean, here we are. We're still like learning the process. And so what happens is on day one and two, I spend time educating what my process is, how I market, how I build in business. Day three, we shot a live wedding. It's a Wednesday. We're shooting a wedding on a Wednesday.

14:59There's 150 people. It's in Seattle. Of course it's raining. Of course there was like this refurbished chocolate factory. And then like the creative live team came in and like redid the whole thing. And so it was a real bride, a real groom, everything. And this was such a rare thing to be broadcast on the internet. So I shoot the wedding. It is a probably a 14 hour day. I'm talking to the camera as I'm shooting. We go back to these little tiny, like we called it, like, it was supposed to be like a studio, but it was really just a pipe and drape. It was probably like four feet by four feet. Jane and I are sitting there and we're like trying to eat, trying to edit, trying to teach.

15:29And then the next day, what I did stupidly is I showed every, all hundred thousands of people who are watching this, every camera, every photo that I took on that day. So thousands of photos unedited and I'm going through and I'm selecting my photos and the pain, the vitriol, the comments of this is, you're terrible. Like what in the world? Like, how did they hire you? Like you've overshot, underexposed, you're out of focus. And as I'm sitting there and I'm teaching this, that night we go back to the hotel and JD had to take me off that bathroom floor. I remember. Because I told you, I was like, I don't think I can go back.

16:12I can't go back. Like, I think I ruined my career by showing the behind the scenes of my business. And then people were like, how can you, how can you have this name? How can you charge what you're charging? This is so ridiculous. and I didn't want to go back on the last day. And I was terrified. I remember. And you told me that I have to go out and I have to show them what makes me me. Oh, I get a little, oh, I get a little, get a little choked up. Thinking about that conversation because you said, go back and show them what makes you you. And on day five, what I showed was, everybody saw all of the ugly, but what the client sees is a very small percentage of that.

16:50And then what we did was we curated all of the marketing assets and then people were completely blown away. blown away. Right. And this is the process. Thank you. Let's talk about the process. This is the dirt. Like this is what, and it's not, you know, I orient around the creative process, right? This is the process. The first draft is ugly and brutal. And, and yet it's the most important draft because it goes from zero to one, from nothing to something. And then we refine it. And whether you're writing a screenplay or, you know, taking a set of photos, directing a video, any of it, it all follows this format essentially you put something out in the world then you find it and it gets better the same is true for a life right we first start out in a relationship and we ask someone we're crazy about on a date and it's awkward and you know and then it gets better that is the way the world works right we iterate and refine and and the creative process just happens to turn that inside out and it's very easy to look at it on a life scale it's kind of difficult and what we saw with your photographs was exactly what we wanted the world to see and you know to me there's all sorts of metaphors in here because you thought that your career was trashed yeah and then 24 hours later you were a hero where your name was trending above Barack Obama and Lindsay Lohan and it was the largest class in the history of the world and so what's embedded in that message is that all of the best stuff in our lives is on the other side of that moment where you're lying on the floor of the bathroom that's where the title of the book comes from never play it safe and again can we say that can we pause there because that like that hit deep all of the best things in our life are on the other side of laying on the bathroom floor they are on the other side of our comfort zone other side of fear right it was my bathroom floor please don't need to go to jasmine's house in order to get i was like i'm gonna start charging people lay on my bathroom floor it's freaking magical it's where you want to be but i I think it's important to establish that this is, you know, all of my personal experiences of, you know, winning and losing.

18:54This is the process that you have to go through. I have had a, you know, one of the longest running interview shows on the Internet and talked to thousands of the world's best entrepreneurs, creators. And this is the pattern. This is not, you know, all the research that I put into the book. There aren't examples of that not happening. Yeah. So give us an equation. Like, so somebody is listening right now. Two parts horse pucky, three parts effort, one part smiles and rainbows equals success. Well, one part eat horse pucky. Yes, exactly. It's not just horse pucky. It's you have to invest. Really, people are listening and I'm like, I wanted, so people know on the show that I do not, I do not bring people on the show that I do not know personally or have not read the book.

19:38And I'm fortunate enough to have done both of those things with you. but I want to hone in the main thing. Sure. And the main thing is it sucks. Yeah. And you feel exposed and you eat horse pucky, but it's on the other side of that. And so, so many people stop at the hard based on your research, based on everything you've seen, based on like you've iterated many times in your career and you facilitated a lot of people. What is it? It's, it truly is that all the best stuff in our lives are, is on the other side of fear. And the ability to go there is a muscle that's trainable. And the irony is that gets trained out of us.

20:21It's very easy to see how creativity gets trained out of our kids. And I personally experienced that. Go back to second grade, Miss Kelly. I made a film the summer between first and second grade. I came into second grade on a high. I was rolling. I had a profitable film. We screened it in David Sholson's basement. Made more money than we spent. eight millimeter film edited all in camera sold out the basement sold candy sold all the so profitable film rolled into second grade had a comic book i had a stand-up comedy routine i have magic had a magic routine and at some point early in the first half of the year miss kelly shut it all down and she said well first of all this isn't appropriate for school this is a business you can't sell your comic strip which i would i would my mom would i would write it up my My mom would make copies of it and I would distribute it for the exact price of a milk, six cents.

21:14So you could choose to have my comic strip instead of your milk. Fast forward, Ms. Kelly said, you know, who do you think you are to be doing all this stuff? I think you should stick to sports. You're a better athlete than you are an artist. And none of this is appropriate for school. So just essentially shut me down. And this is what we do to our kids, right? In the most common environment. And we start being trained just like the creativity is trained out of us. So is our ability or our willingness to push beyond the fear. We start being told what normal is and how we should fit in. And in that moment, I snapped into it.

21:51Fast forward, I mean, I became that person. I was the homecoming royalty, the captain of the football team. I dated a cheerleader. Like I just gravitated toward the most benign, typical script that anyone could. And it worked. and on the last day of my senior year, I got the typical senior award, which is terrifying to me. Like that is like, you're literally, that is the equivalent of saying you are a cliche. And I knew it wasn't good. And I realized in that moment that I had to make some changes. But in the same way that all of those things are trained out of us, so is our innate desire and willingness to go beyond the fear part that shows up in us.

22:38And it's true, like biologically, we are wired. We're social animals. So we're designed to try and fit in because early on we were part of tribes. And if you, you know, you can't stand out and fit in at the same time. So the goal is to fit in. And the message on the other side of all that is that in order to have the remarkable human experience that we seek, we have to go beyond that. and to me this is a muscle you know this is the book that I wrote talks about there's seven innate tools inside of us that we can leverage to get beyond there these are things just like creativity as an example but my punch line is that the world will have you be one way and it's your responsibility to be unapologetically authentically you and that is a difficult job I feel like I have through my own experiences and the experiences of my close friends and you know more than a thousand podcast interviews around this topic I feel like I have cracked the code in a way that I can lay it out and help give people essentially a roadmap for how to do this on their own how to be authentically them and as a result of that how not to play it safe yes and so two things I want to move to the second section the middle section of the framework that you so loving the job that which I freaking love love a framework but two things a lot of people don't necessarily identify as being a creative and so for the context of this section I want us to identify how you classify creativity and it's not just with a camera or paint or penning a poem and then secondly I want to talk about how you applied your version of creativity as you've built multiple businesses and that's really where I want to spend a lot of this conversation is great let's go into the business building let's go into the creative aspect and then intertwine if possible, because I'm very needy podcast host.

24:25I'll take it all. Bring it on. How, how were you authentically you in each iteration? All of the businesses looked so different. Yep. Okay. I do want to put a bow on the creative life chapter because my hope is that what you experienced when you went from, you know, again, showing the process being authentically you, these are the pictures that I took, the world sort of jumped on your back, not dissimilar to the second grade meme, Miss Kelly jumped on my back. And the internet is full of Miss Kelly's. Totally. Miss Kelly. And yet it was the process of playing through that when you showed your final images that the world was completely blown away and you broke the internet because everyone had also, the people who stayed around to watch the next day were like, wait a minute, I saw all these photographs that were trash.

25:21And then you showed up essentially with the butterfly. And to me, that is a very important moment, the playing through of that. And is it reasonable to say that that was bad, neutral, or good for your career? You tell me. It was freaking fantastic. It was one of the best things that happened in my career. You know, you've gone on to have an amazing career in all sorts of different, you know, venues since then. And yet I remember just distinctly saying, cool, this, this is working. And that was an early proof point about exactly the topic that we're talking about. So to me, that we put a bow on there that it was, that was the transformation and the world watched that.

25:59And they were like, oh, this is, we're watching in real time, a person, you know, go beyond their fears. And, you know, fast forward to, you know, my experience with, with that I just shared with with Miss Kelly and now this next chapter of, you know, building businesses and whatever it is that you want to talk about. So it's important we put a bow on there. Thank you. Tell me of the three or four. Are you frameworking my framework? I'm here for it, bro. I'm here for it. Okay. We didn't have no play. Okay. Okay. Let's use it as a linchpin though, because what we did was you created a platform for thought leaders and creators and a wide variety of people to come in, use this creative live platform to show the ugly and then show the transformation.

26:42And so many people became so invested in that community, in that learning process. Now that is so often how a business looks on the outside, like the business I'm building, the multiple businesses you have built. Somebody's watching and listening right now, and they're building that beautiful version of the outside. But let's go back on the inside, building this thing that completely exploded on internet. What was the build like? Crazy town. I mean, again, this just take, for example, your class is the largest class in the history of the world. The New York times came out and said, Oh, Stanford put a class online or something.

27:19And it was 130 ,000 people. And this is the largest and they were actually corrected. But no, no creative live is actually, you know, three years before you had done something much larger and it was Jasmine stars class. So there was a correction of the record and that's like when you're when you are blazing sort of that trail that's both fun but the the what goes into creating that on the other side that most people don't see was a lot of confusion a lot of fear a lot of experimentation a lot of things not working we had a list the first time we went live we had a list on the whiteboard the night before at maybe midnight or 1 a.m before you know at an 8 a.m you know go live and it was all of this that will break tomorrow.

27:59And it was a very long list on this whiteboard. And that is the thing that I think I'm most proud of is the team who assembled. And we just, honestly, it was a couple of employees, some volunteers, like everybody we knew who believed in this idea of making education free and accessible, learning from the world's best entrepreneurs, you know, what it was like for an affordable price. So it was each individual course. And we went from doing one every other month or one a month, essentially, to at our peak, we were doing 70 classes in a month at the same time of that same like multi-day. And so we would have Richard Branson in the studio down the hall from Tim Ferriss and Brene Brown over here and Jasmine Starr over here.