The Chase Jarvis LIVE Show


Lesson Info

Using Constraints to Fuel Your Best Work Ever /w Scott Belsky

Hey everyone how's it going? I'm Chase Jarvis, it's my job to welcome you to an episode of the Chase Jarvis live show here on Creative Live. This show is where I sit down with the world's top creators, entrepreneurs, and thought leaders and do my very best to unpack actionable and valuable insights with the goal of helping you live your dreams in career, in hobby and in life. My guest today is a hyphen, like all of us, he's an entrepreneur where he founded Behance. Way back in like 2006 I think sold that to Adobe. He's got a new startup we're gonna talk about called Prefer. He's an investor, a venture partner with Benchmark which is an amazing firm here in San Francisco and he's the best selling author of the book Making Ideas Happen, my guest is the Scott Belsky. Thanks Chase. (exciting music) (people applauding) They love you. How'd I do? Hey. Is that it? It works. Does that sum you up? I like the hyphens. Hyphens, we're all a bunch of hyphens. Welcome to the show i...

t's been a long time in the making. Thanks for having me. I'm super happy that you're here. What are you working on right now? I mean, ya know, that's, we'll unpack that little intro, but like, Sure. You got a new thing? Yeah, so a few different projects right now. One is uh, one is a new business that I am co-founder of. And my co-founder in the business is the CEO. Got it. And it's a company that is really challenging the norms these days around, around how labor is partaking in on demand market places and online market places and bidding market places and you know, we're kind of looking at all of these skilled relationship driven service professionals. You know, people that would ideally find a client through a referral, rather than online somewhere. Oh, I take so much pride in referring friends to like, I've got the best, like if you're a creator and you want a bookkeeper or an accountant, like I'm freakish about this person. Listen I think that most people say that they would prefer to find a professional they need in their lives through a referral and also the service professionals. Also, ya know, whether their a massage therapist, a babysitter, an accountant, a chef, whatever, they also prefer referrals over anyone else. (chuckles) Right. And so it's like well, if both sides of this market prefer to find each other through this kind of trusted, relationship driven way, why are they or all these like multi-billion dollar companies that are there to basically commoditize labor? You know to match based on proximity or price or 3.5 stars from strangers rather than connecting based on relationships and so what this company is doing, aptly named Prefer, There ya go., it's simple, is to try to help us see the professionals our friends use. And then helping service professionals build their business on their own terms using their own brand to find clients through their clients' friends. It's so smart and so, like I take a huge amount of pride in who I recommend and who I run around with such that most of the people it's like wow, if you can get in to see my hair stylist, well, don't judge, but if you can get in to, like he's an amazing guy, X Y Z. I think there's an element of cultural capital in being able to recommend. Absolutely and context matters by the way. Because you would wanna use the hair stylist of some friends and not others. For sure. And also I mean if you're looking for a photographer or for someone else and it's one thing to just say I need the closest photographer, but really I mean you want to figure out if you're hiring someone for a fashion shoot, you would trust the judgment of someone who's in that industry over someone who just hired them for a wedding or something. So it's, it's exciting. I mean listen it's an early, early stage business. There's a lot to figure out. I do believe though that eventually there will be a company that makes commerce like global commerce with people, professionals, a little bit more akin to like what it was like in a small town back in the day. Where you'd work with who your friends and neighbors tell you. Oh you gotta go see Freddy. Exactly. Yeah. And that's been a trend I think for me in my own career is looking at ways that technology hurts rather than helps people and trying to invert it. I mean if you think back to Behance. Behance was founded at a time when there were all these design spec contests, they were trying to get creatives to do work for free. And creatives would also never get attribution for the work that they did. You never really know who actually did a campaign or ya know, shot a photo or retouched it or did the typography or whatever. And so the idea of like fostering attribution in the creative world was really about Behance, or what was our mission back then. And now, similarly with Prefer, it's kind of helping empower these relationship driven professionals to retain their pricing power, or you know, work on their own terms rather than subjugating themselves to some on demand platform. Great, well, that's one of the reasons I wanted to open with Prefer. I know it's new, and it also requires that in order for it to be successful, it requires people be on the platform, right? It does, yes. But that's a big, that's a big ask. But that's one of the reason I want, if you're at home, it is an incredible service. It's something that I would find that would provide or I would find that would provide an insane amount of value so we're planting the seeds there. But you already did the hard work. 'Cause I was just about to tie that back to a thread. I jumped in real quickly. No but you're good at this! You're professional. Like that, the thread in your work about, you used the word attribution for creators. This is connecting people and I think if, my understanding of Behance is it's the place for folks to showcase and discover talent. Is that still, Yeah. Is that the way you think about it? And you can see and smell the similarities to Prefer, but this is just focused specifically on creators, so take us back to 2006. Back to 2006. Actually maybe before. So I think that's actually, this is worth noting. Speaking of in your intro I talked about all us being hyphens, you started at Goldman. Yeah. (laughs) But you laugh, so why's that funny to you? You know I, so undergrad in college, I was a business major and basically minored in design. I took all the of the design classes in the Human Ecology College at Cornell. And so I was always kind of in between the two. Ya know, and at Golden my only finance job that I took there was a year and a half, then I rotated to another job in the organization focused on kind of organizational improvement and succession planning and stuff like that. Where I actually was using Adobe Illustrator to express ideas and to help, help the firm do a lot of this planning and visualization. Got it. And I remember trying to request a version of Adobe Illustrator for my computer and Goldman Sachs people were like what? Why? So design was always kinda core to how I approach my work. And Behance was really born out of frustration. With just a lot of my friends who were in the creative community, who were always struggling to get their career to be productive. And they were always saying, gosh you know, I'm always kind of struggling to make it, yet I'm so talented. And I kinda got frustrated with this. It was like well, stop working for agencies that work for agencies that work for head hunters that work for agencies, ya know, start working for yourself. Take your career. Take the reins on your own career. So Behance was founded with this mission of to organize the creative world. I remember telling people that and people would be like, oh good luck with that. (Chase laughing) But it was, we had a focus group early 2006, the first and only focus group we ever had at a company, at the company where we pitched all the different things we were doing. We made these paper products at the time. We had an online task management and project management application called Action Method. We had Conference, and we still have a Conference called the 99U Conference. 99U, incredible. Which is ninth year, it's ninth year this year. And we also were developing this idea for portfolio display online and we asked people what they thought of these ideas. And I was looking actually, I moved recently and I was looking at all like this old paper work and I came across these surveys, it's funny, just a few weeks ago. And unanimously people were like well don't do the community. They're like we have MySpace, we have Facebook, we have all these different places. Like the last thing we need is yet another place to like connect or whatever. But when we asked people what they were struggling with, they were saying, well, my portfolio is always outdated, no one can find me in the world of Google, ya know, in terms of like photographer in New York, you're not gonna find one particular person's website necessarily. They always felt like they were at the mercy of these middlemen. They hated spec contests. They never got attribution for their work. These are the things that we were hearing. And so we were like wow, so you're telling us that the last thing you want is another creative community. Yet, everything you're telling us suggests to us that there is a new type of creative community that should be created. And so that was actually the birth of Behance. Oh wow. And it was also a major lesson to me, which was understanding the differences between what your customers say that they want and what they really need. And asking the right questions and not relying on focus groups, but that's another story. The one and only focus group. Yeah, so that was, and then it was five years of bootstrapping this business. It was painful. We had multiple near death experiences. And then a couple, a little less than two years of being a venture backed company and then when Adobe was shifting to their Creative Cloud model, away from this old stodgy packaged software business into more of a relationship driven business with their customers they realized that they needed a community and they needed a way to understand what the customer's creating on a daily basis and staying connected with them. And so that's why we became a part of Adobe at the end of 2012. And I have to tell you like, everyone talks about these unicorns in the tech industry. I think a true unicorn is an acquisition that actually works, Yeah. Because that seldom happens. Usually like the company, the team just disbands and the mission's gone and whatever. You know, but four years later, the team is largely still together and it's pretty remarkable to see the continued evolution of Behance. Well, the back story, fascinating. You mentioned in there, again you're very good at your job. You dropped a bunch of nuggets in there, I'm gonna go back and visit so. Sure sure. Multiple near death experiences. And so this is for the folks at home who are like whether you're starting a company like Scott, or as an independent artist, you're going to have all kinds of near death experiences where you almost miss your rent payments and you've realized that student debts got you down and you have to change careers because X Y Z. In this startup world, when you've got other employees and you've got payroll on a much grander scale than just yourself, looking after yourself, what are some of those near death experiences. Recap some of those things for us. Yeah, I remember we had a officer manager, Brittany who was sitting in my office, ya know, in this little space we had on Broadway in New York. And she was basically saying you know, we're two and a half months away from basically not being able to make salaries. And I was like well, let's review expenses again. Like what are we doing? What can we push off? And ya know, let's rethink like the hiring plan. Like do we really wanna bring anyone else on right now? And I'll tell you though that conversations like that developed this sense of resourcefulness that I believe was more valuable to us than resources. This ability to say all right, let's really really hear, like what do our customers need now that they're willing to pay for it? Let's stop investing in things that we're not even sure they're willing to pay for. Let's also think about, ya know how can we be more resourceful in how we're working and how we're measuring ourselves and anything superfluous that we're doing, let's stop. Just it gave us this feeling of the granularity of our business, of what we were creating and what our customers wanted that I think you lose when you have too many resources and you don't have to do it. Yeah. And so I think it made us a stronger business. It was a near death experience because any little whim, you know in the economy or in our team or whatever could have killed us, right? And it's always tricky because when entrepreneurs ask me now wow, you bootstrapped for five years and you were always kind of teetering at the brink of not being break even, would you recommend that to me? 'Cause it sounds in retrospect, like oh we actually retained a majority ownership of our business, we didn't have to dilute ourselves too much, with too much venture capital. But I don't think I'd recommend it to anyone. Because it's almost like one of those things like what doesn't kill you makes you stronger, but I don't know. Like how many things should you do that almost kill you? It's not necessarily wise. So there, I think those are some of the things that come to mind. The other thing I would say is the benefits of loyalty, ya know in a team. And I was always very transparent with the team. Like here's where we're at. Because I knew all these people would get better, more lucrative offers elsewhere and I knew that the long term vision of what we were hoping to achieve wasn't enough to motivate us every day to work under these conditions. And I kinda had to say, this is the truth, this is where we're at, let's like persevere. Let's roll up our sleeves and for one moment in our lives let's just kind of stick with it and believe. And there were a lot of those conversations in those years that I think made us stronger, but again, ya know was always, always teetering at the point. Well I love, access is a core value of Creative Live. I love access to, not just for the creators to have access world class experts, but the way we talk about it internally is radical transparency. Anyone in the company can put a meeting on my calendar. I'm happy to take it. How important do you think that is for not just building culture in a company, but for an individual? 'Cause so many people who are listening are solopreneurs, are creators trying to get off the ground or the way we talk about here is go from zero to one to get off the ground or one to 10. And how important is transparency with a creator and with audience, how do you think about that? And also with ourselves. I've always believed that the greatest competitive vantage in business is self awareness. When you're at the peaks and everything's going really well you tend to feel infallible. You tend to feel impenetrable, you don't wanna listen to anything like, you think you're right more than you should be thinking you're right. And so in that instance, that's where kind of a lack of self awareness helps the, helps your competitors just leap frog you and that's really where incumbents die, right, is because they stop being self aware of what's going on around them. And then when you're in the valleys as opposed to the peaks, you know this is where you, this is where like your darknesses rear their head. And this is where the team, you know the worst comes out in everybody, the self doubts that we have and the struggles. And it's where we start to have to realize that you know like Carl Jung says, everything that irritates us about others is a window into our soul. You know we have to start to ask ourselves like why is everything bothering me? What's really going on? Why is so and so working out? Like how do I make sense of this behavior? So I think that the investment in self awareness which I think in part is transparency is having an environment where people can just speak up, challenge each other. I mean one of the things I do remember from the early days that a company's transparency I believe is fighting. If everyone kinda knows what's going on and everyone has a strong opinion and everyone's empowered to speak, you're gonna get disagreement. And we have the very big kinda all outs, ya know? Knock down, drag out, yeah. Yeah, and we never, but we never ended a day without sharing conviction. But we were also never held back in expressing and defending and advocating for our views. And so I believe that that was helpful in keeping everyone engaged, keeping everyone honest. No one would ever, the one thing I would always fight as a leader was apathy, ya know? Yeah, to me apathy, like a cynicism. Apathy and cynicism are the things that I, I mean I feel like I'm pretty tolerant as a leader, those two things are like absolute poison. I got no time for that. 100%. And I agree with you. 'Cause skepticism is good, but cynicism is dangerous. And so I think that these are the, these are the, these are the nuances I believe of leading one of those journeys and you know it's very burdensome and all encompassing because you always feel like you're managing the immune system of your team. And you're always trying to sniff out any sort of infection and you're trying to address it and you're trying to bring everyone kinda voice up front. But it feels good when you have a startup or an early stage venture or project or anything and if you really know and you're tuned into why you're reacting, why you're feeling the way you are, it's really, it's power. So this, as long as we're going backwards, we're pulling on some threads throughout your career. Now we connected the role and the service that Behance provided for its community relative to one that you aspire to with Prefer. The thread that is also really prominent in your career as far as, ya know, I've known you for a few years now, and you can look back and connect some dots, is around the doing. And I'm pretty unashamed of saying 90% doing, 10% planning. And I think a lot of folks, ya know, lists and all the planning gets in the way of the doing. So as it relates to your book, as it relates to a lot of the talks that you've given online and your philosophy, you've made a career out of helping others get shit done. So was that intentional, is that a personal aspiration of yours, was it just an opportunity that you saw to help add value? What's the framework for how we should think about your role in helping people make ideas happen? Well, I think that it, specific to the creative community I was always very frustrated by how many ideas there are and how much thirst there is for more creativity when in fact, what a lot of us need, a lot of people watching us, I believe in the creative world need is just is fewer ideas and more organization around the ones they've already got. And I think that actually execution and organization are some of those forces that just propel us forward way more so than more planning. I love the Herb Kelleher quote from Southwest Airlines that "I have a strategic plan, it's called doing things." There's something beautiful about that. It's just kind of the more, the more you do as long as you're honest with yourself, the more you're learning what's working, what's not working, the more you're optimizing, doing more of what works and less of what doesn't. And you're just, also I think that action begets action. When you feel like you're making progress and your team feels like they're making progess you make more progress. Which is also one reason why as a leader of a creative team you need to merchandise the progress that you're making to your people. Ooo, break that down. They actually have to, everyone has to see that you're making progress as a team. And it just doesn't, it's not as logical as it may seem, because day to day, oftentimes it doesn't feel like we're moving the ball forward. Ya know there's just a lot church and back and forth and some cost in trying things whatever. And the traditional metrics of progress, like more revenue, more customers, more clients or whatever it is for you, those measures are not always available to us and they're actually not always even there, especially when you're starting out at a bold project that doesn't even have, hasn't even launched yet, doesn't have any customers. And so you kinda have to manufacture your own metrics in between and then when you do that, what could this actually mean? It could mean printing out all of the tasks that are being completed for yourself or your team and putting them up on the wall. Just to see that like you're actually making progress. Done. Yeah, like I mean the idea of a to do list where when you check something off it disappears seems masochistic to me. Right, you wanna see the line through that. Of course you do! And it's, but it's our psychology. We have to feel like we're making progress in order to continue making progress. It's one of those things that came across amongst a lot of other things when I was writing Making Ideas Happen. I was going to all these especially productive creative teams that consistently defy the odds again and again in making things happen whereas most of us just have ideas and then more ideas, then more ideas, then more ideas and just try to stay afloat. And what a lot of those times, one of those things that a lot of those teams did is they would, first of all they had a bias towards action. So everything was always like capturing things that start with a verb. You know, they would, if they left meetings that had nothing actionable coming out of them, they would just cancel the meetings going forward. They would measure the value of their meetings in actionable steps. They would have a culture of their team where if they were talking and someone said something, oh I'll do this, but they didn't write it down, that they could say, did you capture that? It was little things like that that just kinda kept the ball moving forward, and then, and kept people feeling like they were making progress. So that is super easy to see from the lens of an organization like action items, take-aways from the meeting, whatnot. How do you, maybe even prescribe is the right word, maybe we can get tactical for a second 'cause there's so many good, I mean the book is awesome. Especially if they're, like most folks who are in the space that we're talking about. That's the where they struggle, there's plenty of creativity but the constraints and you put a few things in there and it can often paralyze people. So it's easy for me to extrapolate and I think maybe some of the folks who are listening or watching, but let's get tactical for a second. Like what is, what, how should a creator measure their day to day? Is it literally having a list and being able to, ya know keep one mega-list so you can feel good about what's crossed off? Like you've studied groups, but you also have individuals. Well I think it starts with, first of all it starts with this bias towards action everything you do. So I don't care what tools you use or what paper products or whatever, what pens or whatever neurotic system everyone uses just to feel that they're engaged with their work and that they love the way of tracking and imaging which is important. But whatever it is, having this bias towards capturing things that start with verbs, making sure that they're done is the first step. The second thing is around prioritization. If you take all of the projects that are going on in your life right now, and you place them along this kind of imaginary energy line I would call it. Starting at idle then low, medium, high, all the way to extreme. And you were to place your projects along that energy line in terms of where, how much energy you should be allocating to each project and the tasks associated with each one. When you do this sort of exercise the first thing you'll typically realize is that there are too many projects on the medium, high, and extreme side. It's very hard to determine like which ones deserve low or idle, like no energy at all. It's sort of the equivalent of going to a computer, opening up every single application at once, and then wondering why it's so damn slow. Right it's just because the RAM just can't keep up with the demand. So forcing yourself to put some of those things on the medium, low and idle side of the spectrum, by doing so empowers you in the morning when you have the most energy to over index on the things that are on the high end in exchange for missing deadlines or falling behind on the things that are on the medium, low and idle side of the equation. So it's important to do that, kind of either a physical thing like you make an energy line for yourself, so you just visually always know like where should I be pushing energy right now? And then with your team, if you do this, what you'll realize is that people have the projects you're collectively working on at different places along the energy line. There's a misalignment among the folks you work with as to where the energy should be spent. And I actually believe that that's why deadlines are missed in the world. It's not because people don't care. Wow interesting, yeah. It's because people aren't aligned to where the energy should be spent at any given point. And that you as a leader, if you tell your team hey, these are the things you can miss a deadline on, in exchange for making sure that you meet or beat a deadline on these other things, on like the high and extreme side of the line. So that's like another trick maybe, or tactic to making sure that your energy is being spent wisely. So smart. And I think the alignment part, I'm just looking backwards at some recent meetings here at Creative Live and I think the meetings, or the meetings, the big boulders, the rocks that we wanna move, the ones where we are all very clearly aligned, they move so much more smoothly than, yeah, that's really, Than all the little things. Yeah. 100%. I think being clear about what is important to you is, ya know, step two in your world is the prioritization. And the leader is organizer. It's important to point out that oftentimes in the creative world especially, you know agencies or small design firms or small practices are founded by a creative. And then oftentimes, ya know the creative's litmus test for hiring other people is ya know, would I wanna have a beer with this person? Are they fun? Are they creative like me? Are they, can they riff, can they brainstorm and whatever? And when you hire this like team of creatives and it becomes this like intoxicated orgy of idea generation, nothing ever gets done. (Chase laughing) And so it's so important. You gotta have like these sober monitors you can call them or whatever, but you know these people that can keep you on point and can call you on a lot of this stuff. Do you see, what of those roles do you see yourself in? Because you clearly are creator, you've built so many businesses and we can talk about your investing and all of that a little bit later, but do you put yourself in one camp or another? I think I have another problem which is, ya know there are those dreamers like the creatives, they're are the doers who are sort of like always like what's getting done? What's getting done? And then there are these like third type of people that I call the incrementalists who rotate from dreamer mode to doer mode. Dreamer to doer mode again, again and again. The problem with those people, like me, I believe, is that they never, they risk not scaling any particular thing. Ya know, if they don't have other people around them that are holding them accountable and making sure that there is sort of enough discovery and then enough execution before moving on to something else that you're liable to just have a lot of things that are created but never really see their full potential. Which is why I've always believed I need a team around me. You know I really benefit from having other people I work with for that reason. Is that so you've over indexed on the scaled startup side? Because there is the bandwidth, the resources to have folks that are around you, is that? Yeah, and I think that if I were always kinda doing everything solo in isolation, ya know, I don't think I would, I would achieve something that's sustainable. Like Behance was a 10 year venture basically. And I hope that it's just like always a way for the creative community to showcase their work and connect. But I don't think it would have, it certainly would not have become what it was without, obviously without the team holding us to it and rounding out my tendencies. So, I'm obsessed with doing. And maybe that's the bias for action you talk about that is an important characteristic especially for creators. It's not an accident that I married a producer. My wife is, my wife is a producer and she basically she deserves all the credit for producing my career in photography. But what about tactically for those folks that are creators yet especially solopreneurs or they're freelancers or indie folk and you don't have that, you talked about having a team. Ya know my wife Kate put together the team in my back story and then here at Creative Live. I basically surround myself with operators who are talented and can make the train run on time, get shit done. But having studied this for so long and written books on the topic, what about, like what's the medicine, what's the asprin for the individual creator? I think that the, it's somewhat controversial. Because, I love it, bring it. You know I think that there is a, the theme I've seen across the individual creative practitioners that are especially productive is that they have accepted what I like to call the creative's compromise. Which is essentially compromising some aspect of your natural creative tendencies. To always come up with something new, to always be dreaming, to always be pushing that frontier of imagination in exchange for a discipline of organization that is not natural to them. You know, something that feels synthetic and not completely native. And it's, so it's like a discipline, a discipline that people take on, recognizing that they are in fact compromising. You know some aspect of their natural tendencies in order to produce, in order to make. And it's hard to do alone which is why I think people either marry a producer or someone organizer or whatever. Or that underscores the importance of community. Totally. Who you surround yourself with, whether it's Behance or here at Creative Live. I just don't think that, you know the myth of the lone creative genius is just that, it's a myth. Because so many great ideas will be conceived and die in the minds of creatives who just never got their shit together. And I think we need to, we need to challenge ourselves to adopt that discipline, again at the expense of like some of our creative whims, as well as surround ourselves with people that hold us accountable, ya know, what does that mean? It means sharing ideas liberally before they're ready to be shared. Which is sort of like a shocking thing to a creative professional that cares so much about the polish and sending the message exactly when it's ready and not a moment too soon. But on the contrary, what I hear from a lot of great entrepreneurs and artists is that when they share their work prematurely, they benefit from the accountability and the feedback and the dots being connected by people around them and that those benefits outweigh the cost of someone potentially stealing the idea or of just them feeling like ya know they kinda violated their creative ethos of not sharing it until it's ready. Right, well along that sort of, the paradigm that you were just discussing where you've got, what are some of the violations that you see or the, again having studied this, having lived it yourself, what are a lot of the myths and the lies that we tell ourselves that perpetuate our biggest challenges? You talked about sharing ideas before it's too soon and about structure. But what are some other, like the, I'm trying to help folks at home be self aware, like give them the Scott Belsky filter. So like you know you have a problem if, ya know give us a handful of things that you saw consistently through your time at Behance and now as a leader in other organizations. Like what are the ways that people get tripped up? I think that organization is not a badge of honor. Or sorry disorganization is not a badge of honor in the creative world, even though as soon as we tell ourselves that this is part of my gift, you know that's bullshit. I'm all over the place! Yeah, that's bullshit. You gotta, you gotta, it is really, it is overcoming that and realizing that we all have to give something up in order to make any particular idea see the light of day. I used to think that the schedules were there, like that was part of The Man's constraint to keep me down. Right. And then you start applying some rigor to a schedule, and it's like a catapult. It's like it's so, it focuses you, it limits your, it provides some creative constraints, time is one of the most easily, easily created, a deadline is something you can create for yourself to motivate work. And if you're not being given these constraints like a deadline or even a budget, seek them. I mean honestly one of the most, when I asked creative teams like what are the worst projects you've ever had? Or where did things go completely awry? I have often hears it was when a client came and said, no budget, you know, like no, like do whatever, like think big, I don't want you to be constrained. You know that ended up poorly, turning out badly. It's just kinda like we need constraints and we're not being given them we need to seek them. Which is somewhat counter intuitive to the natural creative tendency to be like oh no, I wanna have a client who just says whatever and let me just be creative. That's not, that's a myth in itself. I think they, the belief that we can do it alone, or that we don't need the help around us as much as we actually do. I think there's a myth or a stigma around self marketing in the creative world where we tell ourselves we shouldn't be marketing ourselves when in fact you must. The tragedy of talent is when no one knows what you're capable of because you're not telling them. And there are shameless ways and non-shameless ways to do it. I think one of the best non-shameless ways to do it is to be a curator of what's interesting to you. So that you're always sharing and pushing out things that you find interesting that folks in your industry, potential clients or whoever are engaging with or sharing. So they're tuned in, so whenever you have something new you want to do they're already listening. Another myth is that there are no competitors in the creative world, that we're all just kinda like peers and competition is a dirty word. I've seen so many examples. I mean one of my favorite ones was Noah Kalina, ya know Brooklyn based photographer for whatever 15, 20 years. He has now been shooting a photograph of himself every single day, and many many years ago, ya know he was doing this maybe for only five years at that point, this was the early days of YouTube Yeah I heard. For context right? And he, ya know, he's sort of a struggling photographer I believe at the time, kind of shooting to put like bread on the table type of stuff. And he about five years into this shooting a photograph of himself every single day, you know and comes across like a story of another photographer, a woman who had been taking a photograph of herself every day for two years. And she's talking about how she's about to like debut this in some sort of gallery or do something with it, and he's like there's no way she's gonna beat me to the punch! Ya know, and so in a matter of a week or so, he puts together this beautiful montage. Every single photograph in rapid succession. He has his girlfriend at the time, this pianist Carly Comando like do this incredible, beautiful piece of music and then he puts it up on YouTube. It becomes one of those YouTube videos of all time. And he gets on the cover of these magazines and like morning shows and whatever else. It was the perfect time, right to just get this thing done. This had been going on for five years with no one knowing about it really. And then the impetus to act, and actually debut it to the world and build his career on it was competition. Was tuning in to what another photographer was doing, right? And so we have to pace ourselves with people around us. We have to recognize that none of us are above the need for an impetus to act on something. And that's another one of those myths that we need to overcome. And that did, just my understanding of Noah's work, that did catapult him into a much more successful career than he was having before. It's one of those five or 10 year overnight success stories. I think he shot Zuckerberg's wedding right after that. There was a bunch of campaigns that he actually got aligned with. So, but isn't competition a dirty word? I mean, aren't we all just friends here to make cool shit? Right, I mean, that's the myth, ya know? I think that, I mean listen, competition is less about wanting others to do poorly, it's more about wanting yourself to do your best work ever. Yeah, it's not a zero sum game, that's the thing that I feel like if someone, I encourage people to stop like, you need to know, I equate it to flying. Like you need to know where the airport is, you know where the other planes are, but you're flying your own ship. 100% And so often people either obsess over something, like this other photographer or completely ignore them. Neither of which are effective. Correct, right. Neither of which are healthy. It's probably something in between. You don't wanna obsess over them, because then you're gonna end up looking like a poorer version of them, and you don't want to ignore them because you need them to motivate you. And you need, especially in the middle of the journey. We were talking about the lack of metrics and proof that you're making progress. It is helpful to have other forces, other people around you, the forces of competition, to just keep you doing as you were saying. It's super important. Yeah, so I think you covered most of the, like the ones that I've heard you talk about publicly before. One of the ones I haven't heard you talk about is the psychology of the creator, self talk, and presumably leading creative teams, analyzing them, writing books about 'em, what's, ya know, I like to believe that the psychology is one of the key differentiators. It's like with sports for example. The differentiator between the fastest race car driver and the second fastest race car driver from a technical aspect is almost zero, it's hundredths of a second. But the psychology is dramatically different from the person who's on the podium every week to the person who's not. Right. With respect to creatives, how, A, what have you seen? B, what are some remedies or things that you had some advice from Scott Belsky? Well, I think it kinda comes back a little bit to the competitive vantage of self awareness. What I also think though, and I always, I always try to advise any teams or individuals that I know who are kind of embarking on very long journeys filled with ambiguity, uncertainty, doubt, self doubt, doubt from others and, is to, is to first accept the fact that the motivation for your long term vision, how you see yourself, which is very important. It also is a great way to hire people and to decide yourself to kinda quit a job and like do something you've always loved, right? But that long term vision is not enough to motivate you on a daily basis. It is a great north star, it's a great hiring tactic. It's a great impetus to do something bold, but it is not enough to keep you engaged on a daily basis. And what you need to do on a daily basis is have a set of short term rewards that we've basically, frankly all been addicted to since birth. You know and it's, it started with parents' love, and gratification for something that we've done, it then became like the check on the tests or the grade on the course and then the salary every two weeks and then the bonus at the end of the year. And I remember at one of our 99U conferences, a venture capitalist from New York, Fred Wilson, made this comment that the two greatest addictions in life are heroine and a weekly salary. And how to unplug yourself from that salary is to really unplug yourself from all of these short term rewards that we kind of use to govern our behavior and keep us motivated. Even when the thing we're trying to achieve is years and years away. So we have to realize that we're not above needing them. And we have to create them for ourselves. And so a big part of the psychology of any sort of long term project is hacking your own reward system. It is creating some synthetic short term rewards for yourself personally like, ya know it could be as silly as I'm going to, I have so many stories. Like I remember one designer, she told me that she wrote a letter to her high school guidance counselor that basically said that she had ultimately become a failure and she had never done this, and this and that. And she put it with his address and a stamp on it. And she said that if I don't achieve X, by next month, I'm going to mail this letter. And it was just so mortifying to her like what would actually happen if she mailed this letter. And what she then would have to talk about with him, and like all this weird stuff that would be ramifications of that action. But it was her own little hack to get herself to like accomplish something over the course of the next month. With Behance, the story I like to tell is how whenever we typed in Behance into Google it always said, do you mean enhance? Do you mean enhance? Do you mean enhance? It was like early on, the plea to the team was we will simply no longer be a mistake. Like if we get enough portfolios out there, enough blog posts published, enough link back love from Google, you know we will no longer be an SEO mishap. And then low and behold, like eventually we typed in Behance into Google and this is now a more like sub one year project, like more like months rather than years and Google knew who we were, ya know? And then actually, I kid you not, Beyonce became popular like a year later and we were back to where we started again. (laughs) No! So these these little short term hacks are like so important as a way to keep your team engaged and keep yourself engaged. And so you have to become a designer of those, of those hacks just to keep yourself engaged. I think that's one of the reasons that I have become a little more prescriptive, that one of the reasons that I'm friends with folks like Tim Ferriss and people who are productivity or hacker experts. And I think why those communities have overlapped, we're both friends with Tim. One of Tim's great hacks is if you wanna, ya know for Tim it's probably like get down to 10% body fat or some, one of his hacks, that if you don't do it, you've written a check say to the political opposition for some amount that would be extremely painful. You do the same thing, you put that in an envelope and if by x date you haven't reached this then that check goes into the mail to the political opponent. Huge part of success is this stuff. Why don't we ever talk about it? 'Cause it's weird? That's kinda why I'm here. It's weird, it's not like directly logically correlated with the project you're working on, but we are just as you said, psychological beings and we are at the mercy of what our minds tell us. And we know that we are, I love Seth Godin, his framework around like the lizard brain. How there's this ancestral part of our brain that's always making us recoil from anything that is not familiar. And we will always find a reason to not engage with something that is risky, that is really more of a long term bold project. We will always kind of recoil to what's familiar and safe and completely unextraordinary. And so it's just so important that we press ourselves, and trick ourselves. Yeah, what are some of Seth's hacks for that, do you remember? We've had him on the show. If you haven't watched that show you should go back. He's so, he's so smart about that stuff. Yeah he really is. And he has such a good simple way of making the case that we just have to kinda push ourselves and manage, ya know, he likes to call the dip. And I've always, ya know he's been a mentor of mine over the years and I find it a always helpful reminder to myself. So talented. So we've been, A, thank you. Yeah this is awesome. Your vision for being able to help, I'll say us, we in the creative community navigate these challenges, it's like you've come along and you've provided an operating system for so many of us. But let's talk about you personally for a second. That's another thing I didn't find a lot of on the internet. You're very good at talking about a lot of things that are out there and analyzing and providing structure and framework and it's the goal of this show for people to hear or learn something about you they can't find anywhere else. So rather than me being prescriptive and trying to pry that one thing open, like what are, ya know, if folks looked under the hood, or into Scott Belsky's life, what are some of the things that they would find that they would be surprised to find? Hm! Let's see. Let's dissect my own brain for a moment. I think that, I think that I, hm. I think I do engage in too many things. I'm always trying to, my struggles are things like saying no, a lot of people probably say this, but I am a optimist. And you know, I think that it's great to always see the potential of a person or a product or an opportunity, but that also has a lot of negative repercussions as well. I mean first of all as an investor. Or a poker player, you are always supposed to be folding. You're always supposed to be seeing what is wrong or what is not gonna work. And so that's not natural to me. Like I push myself to be better at the hallways. I'm a terrible poker player. Right, 'cause I'm always like, I can make these cards work! Same! I'm gonna get this card and then this is gonna happen, and this is gonna happen, and I think there's a gift for being able to think that way. But I also think it's a just tremendous liability. And so what we're all trying to do as human beings, right? Is embrace the things that we're good at but compliment the things that we're bad at with some other discipline that is not native right? Not natural to us. That creatives compromise is something that I deal with myself. So you know that's something I'm always trying to be better at. Also when it comes to fiercely defending your time. It's just like time is just so, so like redundant and cliche at this point, but gosh like it's never It's not enough. It's never ending struggle to be able to focus on the things that you believe will make the greatest impact and are most important to you. And for me also now that's family too. Yeah, congratulations. Thank you, ya know I have two little kids now. And they're uh, ya know, it's the things you took for granted obviously before. I also believe that they make you more productive too. Because the time you have for your work is even more precious. You put them down for a nap and you have the x, you have an hour. You have a window. So it's, but it's also a new realm of excuses that you could bring into your life as to why you're not making progress on things. So I think it's important to just be honest with yourself and to compartmentalize the time you wanna spend on your work and then also truly be present with your family. I think also around the role of like struggle in childhood and how that impacts kind of your work later on, I have a younger sister, I have two younger sisters, one who, the middle one who's a few years younger than I am, when she was born, and I was probably ya know, four or five years old, she lost oxygen when she was born. And for some period of time, we didn't know at the time, but soon learned is that it would really became like a real impairment, you know her development. And she was not able to talk for many years and she was always like a constant concern for my family, reasonably so. And as a result, I was kind of, you know my, I had this like very independent zone of being on my own to some extent, from some age young. And my parents were always there for me and ya know, when I needed them, but there was this kind of on your own type of feel. Which I think developed me in great ways to some extent but also is always like that sort of left a lot of weird stuff that I will always reconcile with, including my relationship with her. But also the angst and what is motivating me and why and all these other things. It's one of those things that I'm trying to, you asked me like personally like things I think about but I don't talk about. I'm always thinking like what is the role of struggle in a creative's life. I think it's common that you hear ya know from people that have embarked on kind of creative careers that they're driven by some struggle. A friend of mine from high school, Rachel Platten, who's a pop star now, she wrote that song Fight Song and like all these other, Oh wow, you went to high school with her? Radio common, yeah. So Rachel and I were friends in high school and we were in an acapella group traveling together. I don't know how I made the cut for this acapella group but, I'm gonna ask you to sing here in a second. But she, I remember I watched her career over the time that she was, really like 10 years of just struggling and making it. Trying to take any kind of gigs she could get. And these were all, ya know I always felt like a lot of the songs were just poppy and light and whatever. And she wasn't really cutting through. And it was only at this really bad point, 10 years in where she was about to give up and like throw in the towel where she wrote this song, Fight Song which was just like a guttural, ya know honest call to, rallying cry, ya know? And it became her major hit. That hit the top of the charts. And it was, it came from like a bad place. That's common. And so in some ways we have to, over the course of our lives figure out and reconcile those bad places that we've been at or are still at and pull great stuff from them. And ya know, and learn to live with them. And somewhat reconcile them. That's part of the show is helping people understand that these huge colossal boulders in each of our lives, they're both incredibly, they're so weighty and they can bring us down, but also something that we can stand on and that the juxtaposition of those two things. And mutual friend of ours Ryan Holiday, he's also been on the show, book called The Obstacle is the Way. Stoic philosophy. A, the book is awesome. B, but conceptually the thing that is, that in the struggle, that's often the thing that can be our differentiator so, Yeah, here's what I'm always wondering though. It's like should we want to actually overcome the struggles, like really truly conquer them? Like where will we be if we do that? Where's the energy? What happens if you win? Does the energy, Right and I guess maybe life always offers a struggle. Maybe it's just about finding it and capitalizing on it. Maybe it's like whether there's a lot of it or a little of it, the potency that is so great, that it's like harnessed like kryptonite. You can like get all the power you need out of it. So I'm gonna shift gears 'cause I wanna know, and I think the world wants to know a little bit about again, came from Goldman, founded a company, worked as a creator with creators, built something up that is now like a piece of cultural literacy. To have a portfolio and to talk about the creator in all of us. It was ya know I would say five years basically ahead of Creative Live. And it's in the community aspect, but now very very aligned with what you guys are working on or have worked on. You founded a couple of other things, you went to work at Adobe which I found interesting as a part of your transition through the acquisition. A, what was it like going from being your own boss to inside a machine if you will, a big publicly, ya know 50 billion whatever market cap company. Was it empowering 'cause you had resources? Was it stifling? And help us understand what that journey is like for you and maybe we can extrapolate and see what it was like for the rest of us. Sure. The experience of coming in and I actually stayed for over three years at Adobe, really exceeded my expectations. I was worried that this big company and you know, the bureaucracy and assumption that there was this politics and whatever that comes along with it, would really, would really kinda dampen my spirit. On the contrary I got kind of riled up by the opportunity. The thing I loved about the people that work at Adobe is that, yes it's a big company. There might be some complacency, as being a big company, but the truth is they're all there because they want to make creative tools. Ya know it's, a lot of them could go other places if they wanted to, but there's this kind of, there's this gravity around, we're creating like the tools that people use to create in the world. And there are a lot of designers and product managers and other leaders that take that super seriously. And so it was fun to really get alignment across them and a lot of the other executives to push a few things forward. I mean one of the things that I was asked to lead there aside from Behance and those efforts was mobile creativity. At the time that I got there, there were like a dozen different apps that all butcher the names of the desktop tools like Photoshop that had no compatibility with each other or with the desktop tools. Or like these $1.99 kinda crappy apps on the App Store. Because they were experiments, right? And it's fine like that. But that wasn't really where the world was going. Now the company was a cloud business. You know all the products had some cloud connectivity. And there was this opportunity to actually bridge mobile creativity and desktop creativity that no one had really tackled yet. And so I was given that sort of challenge. And it was actually a team of nothing. There was, you know it was sort of like build a new team. To build this kind of mobile creativity vision. And so starting from zero and then I engaged a seasoned vice president of engineering, this guy named Govin and then Eric Snowden who was a designer at Behance from Atlantic Records who joined and became kind of our lead designer. And then the team kinda grew from there. And it became an org of hundreds of people that were building all of these products on top of what we called the Creative SDK which was a technology that enabled the desktop tools and the mobile tools to work together in unison. And you could kinda capture patterns and colors and shapes as vector objects and pull them in on Illustrator. I mean there were all these kind of really cool things that we found in the lab and brought to see the light of day. And you can't do that at a small company. You can't just easily get a double digit million dollar budget to build something like this that actually impacts how the creative world works. Yeah and impacts millions and millions of people. That's the, Right. You get to scale so quickly. You get scale. And but you have to be willing to roll up your sleeves and tackle the day to day debates. And I found that I was, strangely enjoyed the process of taking on sort of the ancestral thinking in the company and working with a lot of my colleagues there who just wanted to make this happen. So it's really come along quite well. And ya know one of those moments was when Apple launched their iPad Pro. And I was tasked also with rebuilding the Apple relationship, 'cause I had a few relationships there and as you know from like the Flash wars, the Apple Adobe relationship was not in the greatest spot. And so it was so great to rekindle that relationship and ultimately have our team represented in the keynote for the iPad Pro launch where we were showing the power of these new, these new apps on this device. And so we were in the demos, where we were practicing it with the whole Apple executive team and stuff. And it was one of those moments where it was like wow, like we built this from the ground up. There was zero mobile strategy, now we've kind of brought Apple and Adobe back together and are debuting this vision on stage. And so it was a great experience and I left from that thinking I could imagine coming in and leading a big company as well as a startup again. Like I'm not sure what I wanna do, but I could, I have an affinity for both. Well it, I don't know, I'd launched Photoshop Touch for Adobe at Mac's on stage with the then CEO Kevin Lynch. Yeah yeah sure. And I don't, you were, were you a part of the company at that point? It was right, I think that was before that was before I joined, so that was probably like early 2012 or 2011 or something. Yeah, it was probably right in that window. Yeah it seems like the opportunities to do stuff at scale as a creator, I think this is another thing if I can send a message to the folks at home. Every chapter of your career and it's been, it's really obvious with yours, just how Goldman led to building a business, building a business with being a creator working with and for other creators. When that chapter closed this other one opened. And I think that's a hard thing for folks to see. It was even hard in my own career. Like with Creative Live for example, you go from managing your little team of hustler photo creator folks to having an opportunity to tap something at scale. Is that just true at the upper end of the scale? When you're a company builder? Or what does that look like for individual creators? What are you seeing? Yeah. It's funny like one of the principles I really ascribe to, and I really also say this from my own experience but also with a lot of my friends who are individual creative professionals or freelancers or whatever is that a labor of love always pays off. Maybe not as you would expect, but it just does. If you stick with it long enough and you are authentically doing what you love to do, it just has a way. Because perhaps you have this gravity around you to pull in people that respect the fact that you're pursuing something that you love so much. And then some other opportunity comes up and people are like wow, he's so passionate and he's truly an authentic individual pursuing what he or she loves. And so I wanna bet on that person, or I wanna hire that person or whatever. All these stories end differently than people would have thought they would, but a labor of love just has a way of paying off. It's infectious. It is, it is. You know it's, which is why I always encourage people to incrementally in a career take opportunities that bring them closer to that overlap of your skills, what genuinely interests you and whatever opportunities are presenting themselves, like that, the overlap of those three things is really where you wanna be. And if you can get, just get incrementally closer to that, What you don't wanna do, what a lot of people do do, is they take a step away from that for a bigger pay check. So it's like oh, well, I'm getting this opportunity here or I'm picking between two jobs. One of them is a little bit more what I wanna do, the other one is like better pay. I'm just gonna do that for a while and rationalize to myself why that's a good decision. Just doesn't end up working. That's gold right there, that's gold. So it's critical that we touch on you as an investor. Because I think that's a, it's from what I understand, it's an amazing gift that you've either had or developed. Or luck. Yeah, but I think there's a little, there is a message in there that timing is everything. And it is very much about who you surround yourself with. If you're the average the five people you spend the most time with, who you're spending time with, and does that create, in part, opportunities. Just to recap then early in Uber, in Pinterest, in name five others and tell us about it. Sure. You know, I think, I try to make sense of it myself because I became a accident or relatively by accident. You know it was 2010. I was still an entrepreneur of a bootstrap business having no business investing in other people's businesses. (Chase laughing) And but I was introduced to Ben Silbermann who's the cofounder and CEO of Pinterest. And he was working on a product that was also a grid like Behance and had a real affinity towards designers and he really wanted to over index on the role of design in Pinterest. And I just have an obsession with product. I mean for those who've worked with me before, they just know I'm like a, I'm a product thinker more than anything else. I love thinking about the onboarding experiences of a product, and what the defaults are and you know, and how to make a product for example, put people's work before the brand of the product and how to, you know, what are the structures. I mean I love thinking through product problems and so when I met him, it was just kinda like jumping in and getting my hands dirty with what he was building. He asked if I wanted to be an adviser. And he was also raising a seed round and so I was like okay, I'll do some sort of adviser role. Pinterest as a seed round. Yeah, and I got in. Conceptually it's, And so when you do that, Uber was, I was working, I was working again bootstrapping Behance. We had a partnership with Stumbleupon which was a company that had recently been bought back from Ebay by Garret Camp and when we were one day in my office, which was also my home at the time in New York, he was showing me a sketch that he had actually done on one of our notebooks that we were selling to creative professionals to bootstrap ourselves. And it was like a sketch of like this livery service thing. This mobile app. And said do you wanna like help out? I was like dude, you're a CEO, you just bought back your company and you're trying to make it. I'm an entrepreneur struggling to make it, bootstrapping my business, what the hell are we talking about? This other third love here. Stay focused, that was my wisdom that I tried to impart with him. Fortunately he didn't listen. So the option to be an advisor you know and then an investor in his company. And so over the years it's been other teams of people that I really love that I feel like are solving something the world needs, creating something the world needs that have a product that I have an affinity towards, a problem that I wanna partake in. Another example is Periscope. I really jumped in deep with these guys, with Joe and Kayvon and you know and became almost like a defacto part of that team which was so much fun. Because I really believed in what they were trying to do. And with the opportunity to come into Twitter, I actually remain an advisor and signed on an advisory deal with Twitter just to stay involved with that team and that product 'cause I cared so much about it. So I have not, I'm not a thematic investor. I'm by no means a financial investor. I'm not like scrutinizing their cash flow analyses or their projects and all that stuff. You know I am a product investor. I'm a people investor. And I also really believe that technology can help build communities and empower people. And I just love partaking in those journeys. So those are, you know and all my investments haven't worked out well. You know, when you invest in super passionate teams trying to do crazy things, a lot of them end up you know as struggling and trying to find their way and stuck in the middle forever. But it's been fun and it's been rewarding and you know even for a short period of time said I should just be a full time investor. Yes. What I realized doing that was I just missed being able to jump into the product team for however a period of time I want to, ya know? I just wanted to have a little bit more autonomy in being able to focus on a new team like I am with Prefer right now. And then maybe do some investments and then jump into something else. So I just, I realized that as an investor I just needed that flexibility in order to be happy. So two points there. One, is it fair to say that, I'm trying to make the connection that most of the experiences that you've had as a successful investor to me, and for this, the audience it's less about the actual investing and more about the people, communities that you keep and are you pursuing your interests and co-mingling with like minded people who are doing cool shit? In this case building products. Is it fair to say that you were over indexing on people and products? Yeah, over indexing on people and products and then letting my weakness for extreme optimism help me forecast like where could this potentially be? How can I get excited about it? And again like it's, the negative is there, is there is that there's a lot of like stark realities that hit the business really quickly that most investors would run away from. I just get masochistically interested. And wanna say like screw that, like let's take this on. Let's figure out how to turn this around. You know, let's, they're saying that that's like a bad business model, let's prove them wrong. They're saying that's not a good go to market, let's see if, maybe they're completely wrong. Like I just, I love that, that's why I also love the early stage. Early stage of a company is when there's more of a, ya know it's more of a clean slate. You can question some massive assumptions. And it's less of like the later stage, iteration optimization of a business model. Yeah it's sort of builder versus an optimizer mentality. Yep. Okay so that was thing one, thing two is you talked very briefly about you had a stint as an actual investor which was your job, it was with Benchmark you were hired. It's a huge deal to get hired on at Benchmark. It's one of the only firms I know of where you're in, you're a partner, you share equally with all the other partners, usually there's a big structure and a hierarchy and then you left seven months later to become, or just like slightly extracted yourself to become a venture partner which for the parlance is basically you're connected to the firm, you can bring deals in, but you're not like management. On the gun, on the hook to do all the investments. Yeah, and so was this, the question is was this that same paradigm you described earlier where you decided paycheck over passion? And did it come back to bite you in the ass or how do you look at it? It was a good lesson and learning point for me. Because I, and I love the team there. I think that they're, you know as an investor in a capital fund, like there's no other fund I'd rather be invested in. And there was a part of me that was saying well, since you've been a good investor, you should be doing this full time. And I almost submitted myself to like society's expectations of what you should do given the opportunity, rather than what you would want to do despite the opportunity. And it was one of those really like big learning points for me. I knew very quickly in that full time traditional venture capital role that this just like not a perfect fit. And then, but there was a big side of me that was just saying make it work. Yeah, but so few people get the chance to do this, for me it was pro sports, (crosstalk) professional soccer. So, everyone's like oh my god of course, it's just so obvious, if you can you're just gonna go do this. Right. And you had to deal with that. You had to figure it out. It was tough. You know and I think that it, it took months of sort of triangulation of like why am I not feeling this fit? And what's going on? And also like I really have so much respect for the team you know and I actually, and I get the benefits of being a part of a firm like that. And ya know, fortunately for me, the team was like well, what role do you wanna play? And they said go to Quip Doc, like write up what would the role look like. And so I took a stab at it. And they said great. There was like no negotiation or, But if that's not a lesson right there, that you literally can write your own script Yeah I think you can. Despite the societal pressure. If you build the right relationships, if you are honest and transparent and I think my case to my team there was I think I will add more value in this role and I think they agreed. And I also knew that then I would get the flexibility and the autonomy and the other things that kind of always been part of my creative essence. So I, ya know it was a great outcome from a difficult process and it's, but it shows you that at any stage in life you can succumb to like the pressures of what people think you should do and the spotlight of seduction, I like to call it. From like a great opportunity that may not actually be 100% aligned with what you love doing every day. And it's easier said than done. You know, when you're in the thick of it it's super hard to do that. I remember how hard it was to extract myself out of that Goldman job I had out of college. You know here I just landed on Wall Street, 'cause back in like the late 90s, early 2000s when you wanted to go into business of any kind, what did you do? You went to Wall Street and cut yourself, cut your teeth as an East-coaster that's all you did. And I remember realizing like this is not where I should be, but I still struggled to extract myself because it's comfortable. People are like oh this is like a great job, wow. It was hard to extract yourself from that. But I think it's what you have to do as a builder is be willing to, you know I love how Jeff Bezos always says you have to be willing to be misunderstood for long periods of time. And that starts with just initially making a step that no one understands. And learning to gain confidence from the doubt that you're getting. So smart, that little nugget of wisdom. That will stand alone for a long time. So I wanna be mindful of our time. I wanna go into a little bit of a speed round. Yeah sure. Okay so how important is design thinking, growth mindset for not just individuals but huge teams and how do you think about it? Yeah well I think the design term, the design thinking term is thrown around a lot, right? But I think that we both agree it is really about thinking about your business and your communications and how you merchandise strategy to your team and progress to your team in a design minded way. You know it's, no one read documents. No one has time to read business plans. They're static from the moment they're written. Sometimes I quick diagram or a nice pithy way of merchandising to your team or to your customers what it is you're doing and why can go way further than anything else. And that's the design problem. Is tackling that and boiling it all down. So I love thinking about problems that way. And which is also why I believe that designers make great co-founders or founders. Also having a design leader have a seat at the table is almost like a given at this point. And I also question companies that outsource design at this point. I get pictures all the time from businesses founded by business people or technologists that sort of outsource all their design to third parties. And it's like if that's what you're gonna compete with, like how could you do that? Yeah, look at all the most successful companies of certainly the past 25 years, could argue longer, they had design as, you know Apple is a really, is a really really easy thing to point out. But it's core, core functionality that they've had in the organization. Speaking of core, some of your, let's go to tools. Some of the tools that you use, you mentioned Quip Doc, you've already dropped a couple things, little nuggets throughout, but is there just a list of like if you think through your day what are some of the tools that you use? Yeah, through the day you know I am, I'm using Slack with different teams that I'm involved with. I love Wonder List as a task management tool which will eventually I guess migrate to Microsoft's task manager and application, we'll see. I don't know how I feel about that. EverNote, I still use as a way to like store content you know and just, and I'm a big proponent of just getting shit out of your mind and storing it away. So you can just have the aperture open for other things or whatever you're focused on at a given point in time. So I am always trying to capture everything and file it away and, and I also think that a lot of these thoughts are like fine wine. You know, you just kinda store it away, it accrues value over time, it becomes more interesting. You keep coming back to it and touching it again and touching it again, and then it becomes your next big project. How important to you are habits? And do you have some daily habits that you, it's like brushing your teeth, you don't leave the house without it? Yeah, ya know I don't have, well I do brush my teeth every day. (laughs) You have a couple habits, uh yeah. I'm not, I don't, I don't have too many of those habits. I guess I'm anchored by the actionable stuff. I'm certainly anchored by a calendar and I schedule my time wisely, and I also leave these windows of non-stimulation to focus on stuff rather than just always be reacting to whatever's coming in to me, or whatever I'm supposed to be doing. And but I don't, I have not indoctrinated like many habitual, time driven things I have to do. But even managing your time as in perhaps the world's best known, yeah it's the best known tool or habit is habitually protecting time for the things that you find value in. If like you get, what's it Elle Luna you get what you must have, not what you should have. Yeah, totally. And when you're going into something and you're like why am I doing this? And you're starting to feel that bout of frustration like why is my time being spent doing this? Using that to like correct decisions, decisions going forward, I mean sometimes I'll email my assistant and just be like why, I should not have done this. Like don't let me do this again. You know, just 'cause this is not gonna push anything forward for me. And I was just trying to be nice, and trying to say yes and like just hold me accountable. The role of diversity and inclusion in building products and companies and I guess just the basis for human empathy? Tell ya I think all the time about this now. And I mean there are the logical reasons why diversity's super important, like making sure that the team you're making decisions with reflects the customer base and having people from different experiences around the table who pull from different places and I think all of those things are very important. But the thing that I think is most important about diversity that is talked about a little less is the how you think at the edge of reason. How you get to the point where you're almost being unreasonable in how something might be accomplished or what should be done or, it's the stuff that is explored and discussed and argued at the edge of reason that I think makes the greatest impact in a product, in a company, in an industry. And so if you surround yourself with people that are perfectly reasonable and group think makes people reasonable. Group think kinds brings us down to the lowest common denominator. When everyone around the table is trying to decide and get to something that everyone agrees with, that's when we land on something completely unremarkable. And so how do you keep thinking at the edge of reason and prevent yourself from just acquiescing to the mean. Regressing to the mean. I think is having people around you that are just different than you like and really will think of things completely out of left field and at the edge of reason. As to what was reasonable to me, right? And the only way of fostering an environment that achieves that outcome is just to actually try to get people that on paper would likely think differently. I mean, yes, their gender and background and ethnicity and socioeconomic experience, all these things are, are actually these cultural differences are maybe shortcuts to trying to build a team that is likely to have that happen. But I get frustrated when people just see it as like biological check boxes. Because it's really a strategy. I mean this is fricking strategy. It's important. And that's what you have to realize when there are a lot of teams that have been able to do that time and time again. Keep pulling shit out of like, out of the ether that makes these products more interesting. It's because they are surrounded by people that are not regressing to the mean and are willing to be independent thinkers and see things completely differently. So powerful. We've talked about you as an author, writing books like Making Ideas Happen, we talked about your journey from Wall Street to Silicon Valley. We've talked about some personal stuff. To me that's all, that's a beautiful story looking backwards. That's one of the ways, one of the few ways you can connect the dots, right? But why don't you, before we leave here, tell us about what's next, where are you going? Where should we be looking for you? Besides your name in lights again and again. We know your coordinates, we can put that in, you don't need to burn time on that. But what are you, I mean is it Prefer? What else is-- Well I'm spending my time with a number of different smaller companies as an investor, an advisor. Prefer is one of the biggest commitments I have now 'cause I'm actually a co-founder of this business. And I really care about the team. It's an exceptional team, and it's a big problem. It's just like the future of the economy and not having too many independent professionals, which is the largest sector of the economy commoditized, right? So, I'm really fascinated about that problem. And Prefer is an expression of like how to solve it potentially, right? So I'm focused a lot on that. I'm focused on also a new project chronicling what I like to call the journey in between or like the messy middle of entrepreneurs' journeys. I feel like we spend too much time focused on the starts and finishes of everything. And glamorizing the starts and finishes. And whether the finish is a IPO, an acquisition or a bankruptcy, it gets all the fanfare and the headlines, but how about everything in between? The endurance and the optimization. Yeah that's that 90% doing part thing. About the 10% dreaming and planning and that's the beginning and at the end how am I gonna dunk the ball when you're two inches away from the basket. That's not really all that complicated. It's this, the messy middle is your term I've read before. So you're focused on, I wanna really understand that better and I wanna help glamorize some of the middle tactics that would otherwise just be overlooked. I think that anonymity, that mining this mundane middle no one knows and gives a shit about what you're doing is both a blessing and a bitch, right? You can do all sorts of great things, because no one's paying attention, but only because no one cares. And I think it's a lonely place. I would love to, as entrepreneurs say like what was it like to work with Scott? Like I would aspire to have them say that he was more helpful in the middle. Not just the product stuff which I've been doing for some time, but also just managing that middle. And so I'm actually inscribing a lot of what I'm learning in that area, I'm doing interviews and that's another side project I'm focused on right now. Yeah, that's cool. So we'll see but, it's, ya know I feel like I'm in my zone now in terms of what I wanna be doing and how I should be spending my time and have a lot to learn which is a good place to be. Thank you so much for being here. Thanks for having me. I really appreciate it bud. Folks at home, I hope you took notes 'cause a lot of information in there. We'll see ya again probably tomorrow. (motivational music)

Each week here on The Chase Jarvis Live Show, CreativeLive Founder + CEO Chase Jarvis sits down with the world’s top creative entrepreneurs and thought leaders and unpack actionable, valuable insights to help you live your dreams in career, hobby, and in life..

Subscribe to The Chase Jarvis Live Show on Apple Podcasts, Stitcher, Google Play, and Spotify.

First aired in 2010, the show has featured guests including:

Richard BransonArianna HuffingtonMark Cuban
Jared LetoMacklemoreAdrian Grenier
Tim FerrissGary VaynerchukSir Mix-A-Lot
Cory BookerBrené BrowniJustine
Daymond JohnLewis HowesMarie Forleo
LeVar BurtonGabrielle BernsteinRyan Holiday
Amanda CrewJames Mercer (The Shins)James Altucher
Ramit SethiDebbie MillmanKevin Rose
Marc EckoTina Roth EisenbergSophia Amoruso
Chris GuillebeauW. Kamau BellStefan Sagmeister
Neil StraussYves BeharVanessa Van Edwards
Caterina FakeRoman MarsKevin Kelly
Brian SolisScott HarrisonPiera Gelardi
Steven KotlerLeila JanahKelly Starrett
Elle LunaAdam BraunJoe McNally
Brandon StantonGretchen RubinAustin Kleon
Scott Dadich


Celebrating Your Weirdness with Thomas Middleditch
Persevering Through Failure with Melissa Arnot Reid
Go Against the Grain with David Heinemeier Hansson
Stamina, Tenacity and Craft with Eugene Mirman
Make Fear Your Friend
Create Work That Lasts with Todd Henry
Tame Your Distracted Mind with Adam Gazzaley
Why Grit, Persistence, and Hard Work Matter with Daymond John
How to Launch Your Next Project with Product Hunts with Ryan Hoover
Lessons in Business and Life with Richard Branson
Embracing Your Messy Beautiful Life with Glennon Doyle
How to Create Work That Lasts with Ryan Holiday
5 Seconds to Change Your Life with Mel Robbins
Break Through Anxiety and Stress Through Play with Charlie Hoehn
The Quest For True Belonging with Brene Brown
Habits for Ultra-Productivity with Jessica Hische
How Design Drives The World's Best Companies with Robert Brunner
How To Change The Lives Of Millions with Scott Harrison
How To Build A Media Juggernaut with Piera Gelardi
Transform Your Consciousness with Jason Silva
The Formula For Peak Performance with Steven Kotler
How What You Buy Can Change The World w/ Leila Janah
W. Kamau Bell: Overcoming Fear & Self-Doubt
The Unfiltered Truth About Entrepreneurship with Adam Braun
Build + Sustain A Career Doing What You Love w/ James Mercer of The Shins
How Design Can Supercharge Your Business with Yves Béhar
Conquer Fear & Self-Doubt with Amanda Crew
Become A Master Communicator with Vanessa Van Edwards
How iJustine Built Her Digital Empire
How To Be A World-Class Creative Pro w/ Joe McNally
How To Stop Waiting And Start Doing w/ Roman Mars
Gut, Head + Heart Alignment - Scott Dadich
Debbie Millman: If not now, when?
Why Creativity Is The Key To Leadership w/ Sen. Cory Booker
Using Constraints to Fuel Your Best Work Ever /w Scott Belsky
AirBnB's Joe Gebbia: The Intersection of Art and Business
Reid Hoffman: Build a World-Changing Business


  • By far the best classes on Creative Live!! Thanks Chase Jarvis for bringing so much greatness to the table for discussion! Just LOVE it!
  • Excellent interview with thoughtful questions. Thanks!!
  • So very excellent. Thank you for this!