But here's the amazing thing is that when you ship a number of features and then you start killing a few of them, what you find is that the core stuff gets used more.
A lot of social consumer products, you know, ultimately engage someone based on something they're insecure about.
Hey guys, Sean here. I got a different kind of episode for you that I think you'll like. And just to set the scene for you, so I'm recording this right now. It's Christmas Eve. Got about an hour to go till Santa hits the chimneys. And this episode is going to be with Scott Belsky, probably one of the coolest people I met this year doing the podcast. And as I'm recording this, you know, I'm just supposed to do the intro and tell you what this is about, but I'm feeling a little reflective because it is the end of the year. I started this podcast about six months ago on a whim. I was bored. We were selling our company and we were in the due diligence period and I was just getting itchy waiting for lawyers to finish doing what lawyers do and I was like I want to start something new. And so I knew I couldn't start a company so I started a podcast and I didn't know if anyone would listen.
And amazingly, you know, I really thought nobody would listen to this thing and now here we are six months later. I'm looking at the dashboard right now and there's 526,000 listeners, over half a million listeners already in just the last few months. And so, I never thought that that would happen. If you're listening to this right now, thank you. This has been a kind of an amazing new addition to my life. I started the podcast because I thought it would be a great excuse to hang out with interesting people. I don't drink coffee. No caffeine for me. Never had the taste for it. So, I didn't like inviting people out to coffee or trying to make up excuses to meet. And I thought the best excuse would be, 'Hey, come on my show. Come on my podcast.' And for whatever reason, that kind of flattery works.
So, I wanted to invite people like Scott onto the podcast. And somebody like Scott's interesting because, start the show with this, which is he's done basically every job I've ever thought about doing. So, he bootstrapped his own startup. He raised venture capital and tried to grow that way. He sold his company and then he became a tech executive. He's currently the chief product officer at Adobe, which is, you know, obviously Adobe is a massive company. So he's been a founder, he's been a tech executive, he's been an author, he wrote a book called The Messy Middle which is an awesome book about the process of creating stuff. So, you know, creative guy who wrote a book. He's been an angel investor in companies like Uber or Pinterest, aka, you know, two of the best angel investments of the decade. Then he was a VC with Benchmark, one of the top funds that exists. So the guy basically has done everything.
And what I was blown away with and what you'll get out of this conversation is he's just a good dude. He's a very down-to-earth, smart person who I think he says this somewhere in it, which is his goal wasn't to become any of those things. He didn't say, 'I want to be a tech executive. I want to be a founder. I want to be an investor.' He was just curious and followed his curiosity and it kind of led him down those paths and I found that kind of inspiring.
So, you know, as the new year hits, I'm thinking about all these different episodes we've done. I don't know, about 25 episodes, meeting all these great people and then even getting a chance to meet some of, you know, if we got half a million listeners, that's a cool number. But I've gotten to meet, you know, hundreds of you in person at one of the live shows or people who email me. We're going to try to squeeze in a Q&A episode this week. So, if you are listening to this and you have a question that you wanted to ask, you know, it could be about business, could be about investing, it could be about a podcast, whatever, I'll answer. Just shoot me an email. My email is
[email protected]. So just shoot me an email. I'm going to do a Q&A episode. I already have like 20 questions or so, but send them in and I'll try to get through as many as I can. I hope you enjoy this episode. We're not going to do a super fancy intro. We're just going to go right in. And it's a little bit different. We recorded this thing at night and I just didn't have the energy to do the whole, okay, let's start with your story from beginning to end. I just hopped around on whatever was interesting to me and it made for a fun convo. Me and Scott, I consider us friends now after this because the conversation was that fun to be a part of. So, it kind of hops around. It's a little bit of a different flavor. I hope you guys like it and again, thanks so much for supporting the show. The podcast is already bigger than I ever dreamed it would be and all that made me want to do was make it grow even 10 times bigger. So, that's what we'll be doing next year. All right guys, enjoy the show.
Scott, welcome. Thank you. So, Scott Belsky, I don't like doing intros because usually I butcher it when I do it, but what I thought was interesting about having you was like you've done the career path that's like everything I've thought of doing, you've actually already done. So, you know, you've written a book, you bootstrapped a company, you raised venture capital, you've sold the company, you've invested, you've been a tech executive at Adobe. So, I'm like all the potential career paths you've actually explored. And so, I was like, okay,
A career identity crisis at all times.
Yeah. Either you know exactly what you're doing or you have no clue what you're doing,
Right? Fine line between the two maybe,
Right? And currently, which one of those paths are you in at the moment?
Yeah. I mean, listen, sometimes I think what is my happiest state professionally? Actually, just generally. And I think it's the feeling of feeling fully utilized. And I think that personally, you know, I'm a dad, I'm a husband, I'm a friend. You know, you feel utilized in all those ways. And then professionally I feel fully utilized in a day like today actually where I had meetings with product teams. I had meetings kind of leading change in the big organization, those types of meetings. I also had pitches, a couple pitches from companies that I might invest in. I also helped make a couple introductions to companies that I'm already investor in. And I also even had a quick talk related to the book. And so I feel like every muscle was stretched in some way or another. It's a day. And so I think that I've always just tried to, you know, pull threads on curiosities. And I do, you know, for better or for worse, I kind of am enjoying, you know, both ends of the spectrum these days.
Yeah. To give people a sense, it's like 9:00 p.m. on a, what is it, Tuesday, Monday night? I don't know. Tuesday night, somehow we squeeze it in. And I was telling you, I was like, I give you credit because I know it's easy when you're like two weeks out and you're like, 'Sure, yeah, we'll make it work.' And then the day of, you're like in your like ninth Uber of the day and you're like, 'What am I, who is this podcast? What am I going to go do?'
Yeah. Feeling good. Feeling good.
But yeah, give you props. In fact, on the last episode, I sort of put out one of my life theories, which is 80% is just showing up. And most of the things that you don't want to show up for, if you just build that discipline to just show up, good things happen. You just have to do it. Okay, so you've done a bunch of things. If I'm listening to this, I'm like, okay, why am I interested? So, you created Behance, which if you're a creative person, you know exactly what Behance is. But if you're not, somebody who's maybe a designer or somebody in the creative world, what was Behance?
Yeah. So Behance was inspired by a bit of a sense of frustration with the creative world and just how disorganized it was. A lot of my friends in the creative community, architects, designers, people I knew from college, their careers were at the mercy of circumstance and I felt like they felt like they never got attribution for their work and I felt like they were not doing the greatest they could be doing in their career as a result of that. And so Behance was an effort to organize the creative world and people would always say, 'Yeah, good luck with that.' Why are people having their portfolio sites sitting on some websites and searchable and sortable based on the client, the search term or whatever, and then through someone's work you discover who that person is, then you see their portfolio, and then you see who they are. And so it was inverting the model to some extent. And it was a long slog. I mean, Behance was five years of bootstrapping, two years as a venture-backed business, acquired by Adobe, three years of integration. It was an incredible
Partridge and a pear tree.
Right. Right. We kind of sell it all. But it's great. I mean, I love building products for creative people. I find that ultimately across all industries, creative people are the ones that really move things forward and they compel us to take action. They, you know, prompt emotion through media, movies, whatever it is. So, it's just kind of an honor to build things for creative people has always been something that gets me going.
Yeah. Somebody asked me, they're like, 'Why do you like to do that? Why that?' In traditional terms, I don't seem that creative. I'm not a designer. I'm not an artist of some kind. Not making music. You know, anytime you're trying to make something new happen, you're being creative. You know, fundamentally, you're problem solving something new.
And I'm like, you know, it's really simple. Like, I like the new in the world. I get excited about new. And if you want new, you need people to be creative and you need creative people to have all the tools at their disposal to do what they do best.
Well, I think it's, you know, creativity is genuine interest combined with initiative. You have like deep interest into something. It doesn't matter what it is to your point, but you also have the initiative to do something with it. And those are the folks that get fascinated by those edges that will someday become the centers and, you know, that's what makes things work.
And so normally on the pod I'm like, okay, Behance, great, that's the mission. How did you think of the idea? How did you get your first 100 customers? Those are the normal ones. And so if you're here to listen to that, sorry, I'm not going to do it this time. There's people who have asked you those questions. I've seen those interviews. So actually I don't know if it's because it's 9:00 p.m., I'm in the mood to just talk about other things. One of the things I want to talk about is you wrote this book, Messy Middle.
Which is cool. I'll tell you the premise as I understand it. The premise as I understand it is 95% of the conversation is around the beginning and end of companies. I'm guilty of it myself, but, you know, press and, you know, the media is much more, you know, that's their bread and butter is like somebody's starting something, somebody's ending something either for failure or success. And so 95% of the talk or 99% of the talk is about 1% of the time that actually goes into any venture. And everybody just sort of fast forwards the middle, the actual like sort of doing and navigating of the unknown. And so that's what The Messy Middle is about. It's about that middle section. I think Eric Ries has this good phrase where he's like, 'Act one, we go into depth about the hero and how they came up with their idea. Act three, you know, the resolution. And act two is the montage, right, where it's all the hard work, and it's just like all the training. You just quickly fast forward through all of it so you can get to the good.' It's not sexy, but it's kind of all that matters. And so, why write the book?
Well, I was fascinated by that big period of volatility that just seemed like an endless succession of lows and highs. I was interested in the idea that we're not our best selves at the lows or the highs. We're not our best selves at the lows because we make decisions out of fear. You know, at Behance, we saw new companies, new competitors emerge, and we made a lot of mistakes at times where we would suddenly try to emulate and then realize, wait, we just lost touch with what we really are and what we're good at. And then you're also not your best self at the highs because you falsely attribute the things that you did to the things that work. And so, there's something to be learned at those moments. There's a practice to be developed in how you endure the lows and how you optimize like hell anything that works. And I just, that was what was interesting to me. And I wanted to interview and chronicle a lot of stories and insights from people that I've worked with, boards that I was on, entrepreneurs that I partnered with, and also things that I learned, you know, my own experience. And originally I kind of started this as a project for myself and then I realized I...
I had this Evernote notebook of like 680 or so insights and I said, "Okay, I'm going to pair this down and ship it." So that was the origin of the book, because I was thinking, why not a blog post, right?
I read a bunch of your blog posts. Part of the reason why I wanted to have you on is your blog is actually really good. What's the domain? It's just like belsky.com, right?
Yeah, I guess. Yeah, it's like on Medium, but I don't know. You can get there through many different ways.
I've read a bunch of your things and you have these almost like watercolor art diagrams of stuff. So I've been reading these for a long time. I have a couple friends—Sam from The Hustle who you invested in, and Greg Eisenberg—who say amazing things about you. So that's why I wanted to have you on: your philosophies that I've read, and then friends who vouch for you. Why not just do a blog post? Why did it have to be a book?
Yeah, I mean it's a good question because a book is kind of stagnant. You can't really update it as easily. I think though that a book is a forcing function to distill it all down and also try to find the threads and then to package as a piece of art. One thing I did with this book is every insight has a statement that is also presented in a designed section to give it some gravity.
What's an example of one of those?
An example is: the science of business is scaling. The art of business is the things that don't scale. And then it's like, okay, what is that? So that will be a two or three page section about how we procrastinate over all the science nuances. Actually our instinct is to not want to do anything in our businesses that doesn't scale because we feel like that's a waste of time, when in fact a lot of the greatest examples of distinguishing a brand or a service are the things that don't scale—like Airbnb sending out photographers for every apartment. Every company has their example of the things that they did that don't scale that ended up being the art. How do you preserve that as you grow and how do you decide what your art is? So that's an example of one of maybe 200 or so insights in the book.
Gotcha. You write this book and I like it because there's some books where you can kind of tell the person who's writing this—they're either nowadays not trying to make money off this, but they're trying to parlay this into speaking gigs or things like that. But you already had your sort of success and win. So it feels like it comes from a different place. It comes from a place of I want to share wisdom or first tap into the scattered wisdom you had in your Evernote files, put it together for yourself, and then generously give. Is that right?
Yeah, it was weird. It was actually—I remember the moment when I was entering another one of those things I had observed over a board meeting or something, and then I realized, gosh, there's so many in here. I think it was on a plane. I remember being like, gosh, if this man goes down, like no one's ever going to see any of this stuff. It's only going to be for me. And so that was one of those moments. I also think there's a part of me that aspires to do more coaching and helping people build products. One of the things that I love doing—and I've done it with Sam and also with Greg and others—is help them develop their products and then build their product teams and hire the right designers and build a design culture. I did see this book as an opportunity to share some of the things I've learned and some of the things I'm thinking about and do more of that stuff. So it was in some ways a cornerstone of that intention I have for the next part of my life.
What's something that you commonly—so when you advise people on building products, making better products. Obviously as an entrepreneur you'd always be better, you will never turn down the opportunity to make your product better. It is your rock. What's some common things you find yourself constantly advising people to do, or questions you keep asking, or advice you keep giving? Is there anything that's sort of a pattern you're noticing as you do this for different companies?
I mean there are a lot of them. I would say like two that come to mind. One is obsessing over the first mile of the user's experience of the product, which ironically typically is the last mile that the team spends actually thinking about. And yet it's the only part of the product experience that every customer will in fact experience. After that, it's just drop off, right?
First mile—just so people—sorry. So it's like literally the onboarding, the splash page onboarding, step by step, the questions you're asked before you get into the product, how quickly you actually realize any form of value in the product, the defaults of the product—does it show you everything at once or only a few things? The progressive disclosure of functionality?
Like all of these factors are things you must consider as you're nailing that first mile experience, which is in fact probably what determines the fate of most products, frankly.
Yes. You get 60 seconds or 90 seconds with the bulk of your potential customers.
And I like to remind folks that every customer, as great as they may be, and as wonderful as your product may be, every customer is lazy, vain, and selfish in their first 15 to 30 seconds of using your product. How are you going to cater to them in that world? I think the mistake we make is we expect our customers to have too much faith in us as product builders. They don't care. In fact, they shouldn't, because their life is too busy and they shouldn't spend any amount of time, energy, or effort until they actually know that they're going to get value out of it. And so that's the conundrum. That's one example of something that I love working on with product teams. Another example is kind of unpacking the psychology of their customer. A lot of social consumer products ultimately engage someone based on something they're insecure about, something they want to have validated, something they want to learn or they're worried about. There's a lot of underlying nuances of a product that are really driven on psychology. I was talking to the team at VSCO the other day and they decided not to aggregate the number of followers that you have visible to you, nor do they let you see how many likes something has. That's very counterintuitive to what we know about ego analytics and the things that drive social consumer product usage. But they had an insight, which was the type of customer and how they wanted to use the product. That sort of thing is a very important thing to distill and then make as a core principle.
And so when you're investing in companies, I'm guessing you're looking for—in that first couple, first conversation with the entrepreneur, you're trying to figure out what insights do they have about the psychology of their customer. And also when you demo the product, how's this first mile experience? Those are probably two of the first tests of your evaluation.
Yeah, they are. And of course, for consumer products and for enterprise products, there are different types of tests or different types of lenses you look at them through, but I think that those actually apply to both. In the enterprise, you realize that everyone wants to look better in front of their boss. Everyone is sometimes even more lazy in terms of what they're willing to do. And so you have to build products and first mile experiences that take those things into account. So these are important things to think about as you're considering—as an investor, if you're a product-oriented investor like me.
Right. And what are some of the investments you made that you're proud of?
Yeah, I mean, my first ever investment was Pinterest. So I met Ben Silbermann back in 2010 and I had no business being an angel investor. I was just leading my own company, but I had met him through—I think it was our intern. Ben was coming through New York to raise money because he had a hard time filling his round out here. We both were building products that we were orienting towards designers to some degree and a lot of the pins on Pinterest were driving to Behance pages. I was seeing the although slow but rapidly growing source of traffic. Back then it was of course Google, but then StumbleUpon and Tumblr and maybe a couple others. And then I just started working with him first as a product advisor. And then when he was raising the seed round, he was like, "Do you want to participate?" And I was like, "Okay." So that was the first foray. It was amazing because it was just cool to see a product at that stage and to share some of what I learned, but also just engage in a lot of healthy debate. Every product experience that I've had with the team has been remarkably different. I sat on the board of Sweetgreen for a few years. A totally different world, right? But then again, Sweetgreen's thinking about efficiency behind the counter and how to reduce operations time of preparing salads, the form factor of the actual bowls and how that increases efficiency and is better for the environment, the design of the space, and then the mobile experience—they had this ambition of having over 50% of all orders started on mobile. I just love getting a bit geeky with product problems and helping solve them.
That's amazing. Okay. So when you made that first angel investment in Pinterest, you don't have a budget for this. You're not like, "Okay, I've made it," because you're still doing Behance at the time. You had not exited, correct?
And so you said, "I'm in no position to do angel investing," but you did it anyways. What risk did you take there? So when you put in whatever you put in, what percent of your net worth were you putting on the line at that time?
Yeah, it was probably a good chunk of my salary. One of the other things I did though to rationalize it for myself—I remember—is Ben had worked at Google. He had a network on the West Coast. I was this new entrepreneur in New York that didn't have any of that network. I actually felt like I would learn a lot from this and so in some ways I was like, I'm sort of paying for an education if nothing more. I just knew so little about everything I do now back in 2010. So it was nine years ago. If you have a real deep curiosity about something and then you find someone you really respect and you have a lot to learn from them, find a way to get closer to them. Find a way to work with them. It just always leads to something and you may not expect what it is.
Yeah, this is timely. So I just yesterday invested in a self-driving car company and my last sort of—as I was going through the last checklist of okay, should I do this? This is meaningful money to me. I'm not at the point where when I invest dollars in, I actually really want those dollars to come back. This is not like the philanthropy angel investing that some people do. And so my last thing was like, look, I'm going to learn so much about robotics, machine learning, and self-driving cars. That's the future. Whether it's this company or the next one, these guys are the future. And this might just be my education. Worst case scenario, this is my education. I started helping these guys the last couple days try to get their business off the ground. And already, I feel like I get to live in the future a couple hours a week just by working with them. It's a long-term view on the value of learning and relationships, but also for those that aren't ready to write a check to people, there's so many ways of getting closer to people that you admire and want to learn from and keeping those relationships. I think platforms like Twitter are amazing in that regard. There's some people that I somehow got connected to on Twitter that I've never even met in my real life who just reached out to me and just started to share enough information and witty observations and feedback on something that I wrote that I just start to follow them and then I follow them for a year and two years and then these are folks that feel like you know them. Anything that they were probably doing next, I would probably be first in line to help support or at least learn more about. It's just enlightening that anyone can through their own insights and just hard work and knowledge sharing—sort of generosity in that sense—build relationships these days.
I learned this the hard way. I host these mastermind groups. Do you do anything like this, like a dinner series or anything like that with the same set of people where you get together every two months or so where it's like your peers?
Like informally? There's probably groups that I do that with.
So the regret was I moved to San Francisco and I got invited to one of these and I was like, this is great. This is an awesome way to learn and meet people because the good thing is you're at a table with founders and they're not selling. You're not their employee, you're not their investor, you're not their customer. So they're actually telling you what's up with their company and you're sharing likewise. The first couple groups I was in, if I had just written checks to all of them blindly — just writing the same $10,000 check in all of you guys — Calm was in that crew. They would have paid it off.
Yeah, exactly. They would have paid it off. Clearbit was in that crew. Product Hunt. Zola Electric, which is the biggest solar company in Africa. That portfolio would have done amazing. I look back and I was like, man, I did the first part right, which is what you're saying — I just spent time with interesting people and added value to them through sharing ideas, insights, whatever, being helpful. But the lesson I learned was why wasn't I investing? I kind of asked myself this and I thought because I wasn't thinking of myself as an investor.
Then it happened again. I saw this company called Lambda School that I thought was going to be really big. It was really early on. I started talking to Austin and I was like, "This time I'm not going to mess this up." I convinced my friend. I was like, "I found a company that's amazing. If you invest, I'm your scout here. If you invest, give me 15% of your action and let's do it." That was like my first real deal where I was able to just put it in. Since then, once we sold, I got a little more money so I could do it myself. The lesson I learned and what I would tell anybody who's listening to this is: don't count yourself out as a player in the game, either as a founder or investor. There is a way if you're willing to be creative and helpful enough. I think that's — so, rant.
I think that's one of the greatest cultural attributes of the ecosystem of early-stage founders, is that we all know how much those circumstantial relationships matter and how much we learn from one another and how we actually can't do it alone. That manifests itself in ways like what you're describing.
Did you invest in Uber? Is that right?
Yeah, I did. That was also kind of early on. The funny story there — we were bootstrapping our business, Behance, early days with paper products of all things. We were making paper products for creatives to be organized. They're serious and they're called Action Books. They're actually still out there.
One of our core partners for Behance from a traffic perspective and partnership was StumbleUpon. Garrett had recently purchased StumbleUpon back from eBay. He had sold it and then he brought it back. He was in my apartment, which was also my office back in the day in New York, and we were kind of jamming on some product stuff. He whipped out one of our Action Books that I had given him previously and was like, "Hey, check this out. I'm working on this side project." And then he literally invested in the sketch. He sketched me these sketches of this product where it's about summoning a black car as opposed to having to dial for it.
I'm like, "Dude, you should be focused on your business. You just bought it back. I'm a founder CEO struggling. You're a founder CEO now struggling. You're thinking of making it — it's a distraction. That's a textbook distraction, right?" Fortunately, he didn't take my advice.
He said, "Do you want to be involved?" I kind of was like, I don't know. But I also became a product adviser for him. This is actually even before Travis was in the picture. Ryan was involved. The team got up and running and he asked me if I wanted to invest. I again was like sure, but a very small check, which was all I could do at the time. That was a journey as well.
So you do this sort of starter product advisor, and because of that you're at the table, and so when the time came you were in.
