Interview

Scott Belsky

By  | 

Scott Belsky, Co-Founder/Head of Behance; VP Products, Mobile & Community at Adobe; Author & Investor

The fourth episode of the Collective Wisdom podcast is focused on the care and tending of creative communities. You’ll learn why apathy, not anger, will kill your team; why product teams should strive to kill, rather than add features; and why it’s important to celebrate the “middle” of a startup’s journey.

Like what you hear? Subscribe!

iTunes | Soundcloud | Stitcher | Newsletter | Twitter

Don’t have time for a podcast? You’re in luck! We have also prepared a transcript with links, highlights, and other audiovisual elements for easy skimming & sharing.

Micah Rosenbloom is the host of Collective Wisdom and a Managing Partner at Founder Collective, an early-stage VC firm that has invested in companies like Uber, Buzzfeed, and Hotel Tonight.

 

Micah Rosenbloom: Scott, you’re a well-known entrepreneur, executive, super successful angel investor. I really appreciate you as a philosopher. I follow you on Twitter and it seems like everyday you have a nugget of wisdom that forces me to think. You’re bit of a modern-day Confucius. My question is: where do you come up with this stuff? Is Twitter a place for you to brainstorm and get your ideas out? Did someone write this stuff for you? How do you come up with such good stuff?

Scott Belsky either leading his team at Adobe, running a major publishing organization, or working on a new investment.

 

Scott Belsky: First of all, I think I aspire to be all the things you just rattled out there. I think I’m a student. I think that when I’m in meetings throughout the day, when I am just trying to solve a problem, some little insight will pop into my head. These days, Twitter is my way of not only capturing it so I can remember it but also sharing it and seeing how other people build upon it. Oftentimes, I’ll also see some interesting points or disagreements that I’ll retweet to share that on top of it.

I’ve always enjoyed the academic side of what we do: building things, investing in people and ideas, learning from mistakes, and understanding why something is not working. There’s one part of me wants to be reactive and fix it. That’s the kind of doer side of me. Then there’s also the thinker side of me that likes to say, “Gosh, like, why did this happen?” It’s fun. It’s fun to share. I also think I benefit from a lot of other people who do the same thing, share some of their thoughts on the open web.

MR: Do you get some give and take from the community that makes you think?

SB: Totally. The theme for me is what I’d like to call the journey in between. I feel like we love celebrating the starts. The starts of things are these glamorous moments where people just start something in the garage. A classic story, right? We also love to celebrate the finishes, the acquisitions. Whether it’s a bad finish or a good finish, the media loves it. Then momentary finishes like raising money is sometimes seen as a new start or a new finish, depending on how you look at it. Everything in between gets no coverage. It’s not sexy. It’s not clear. It’s actually very messy. That’s the stuff that I love.

Photo: RosieTulips

 

MR: I think, to that point, I started my first business in ‘98, second business in 2002. There really was no Twitter and startups can be very lonely especially in between. In the very beginning, there’s a lot of excitement. If you exit, there’s a lot. In the middle, it’s lonely and I think Twitter, in some ways, is a place for other folks to, it’s sort of the town square. It’s an opportunity to vent and see that other people are going through similar stuff, get suggestions and ideas.

SB: I mean that’s social media at its best and, obviously, there’s many things as it is at its worst. At its best, I think it makes us feel less alone. I think it makes us feel some partnership through various parts of our lives. You saw Sheryl Sandberg’s loss of her husband and the way that she used social media to connect with others and share her thoughts real time and grieve with others. When you’re an entrepreneur starting something or when you’re an author starting something, social media now is our source of accountability, partnership, inspiration, grounding. It’s certainly humbling to be able to see what other people are accomplishing and being like, “Wow, I aspire to be as productive as that person.” Social media serves all these purposes, I think. I think that being in this community, it’s something you should contribute back to it if you benefit from it.

MR: In that spirit, I twitted out to my followers. I don’t have nearly as many followers as you. By the way, Scott is @scottbelsky on Twitter. I said that I was interviewing you on the podcast today. Micah Baldwin, who gets credit for having the same first name as I do, emailed a question or tweeted a question, rather, that says, “If you could be any Photoshop brush, Scott, which one would it be and why? You’re welcome to swap out brush for gradient.”

SB: Thank you for that allowance, Micah. What I would say is that I would definitely be a natural brush. There are these new essentially homemade brushes that people are making now with this new app called Adobe Brush we came out with, where you basically capture anything around you and immediately turn it into a Photoshop Brush. I would definitely be an environmental type of brush. Actually, my first major at Cornell was in environmental sciences in science and rote systems. I always feel like a lot of things come back to nature. I love going around and capturing little things that I can see as brushes and if I were a brush myself hopefully I’d be the organic kind.

Scott kicking off 99u. Photo Credit: Digital Results

 

MR: By the way, how do you toggle between Adobe and the products you’re building there, your angel portfolio, the stuff you do at 99U? How do you even separate that in your brain? Given just how many different things you’ve got going on and different product and skills that you have to tap into?

SB: It’s an interesting thing I always am thinking about. I feel like part of my training for this was starting Behance well at Goldman Sachs was building Behance well at business school. I was always managing in some ways, two lives at once I felt, and trying to find the overlaps in between where those would be like sweet spots of productivity for me. For example, today, working with the team like Periscope that is building a modern technology, a social experience using Adobe tools, and then also working at Adobe running mobile products. Obviously, I just close to both sides what I’m doing. I try to avoid anything competitive but it’s really helpful. It helps on both sides.

Of course, then, Adobe was one of the first adopters of Periscope to spread a lot of how their tools work and became an example for Periscope of how companies can use it. I like to find those sweet spots and invest my time and energy in those. I think that it just forces me to be more productive and economize and also really to say “no” to the things I don’t think I’ll add value in.

MR: Someone was describing to me earlier today that you use, I think it’s call the Kanban System, which is a series of less, basically, of projects and you start to move them along. I think it’s from the Toyota Production System that we learn about in business school. I’m curious if you use tools or lists or software to just track everything going on. I use Evernote and I have certain notebooks for different projects but they’re not all that. It’s probably not the best system in the world. I’m curious if you have any tips or tricks on tools to keep everything organized and moving along.

SB: At the top level, I have an extreme bias towards action. Everything that I think of I write down as something that starts with a verb. Whether it’s to expand on it later or to follow up with someone or whatever, I use tools like Wunderlist. I really like Wunderlist for task management. I use Evernote for longform writing and tracking things and stuff like that. Then I also use Slack for all the various teams that I work with so I can just hop in for even a few minutes, just be completely immersed by how a team is working and who’s talking about what and what’s going on. I find that these tools enable a new level of productivity and cross-pollination that was never possible before.

Photo: Jude Bird

 

MR: Are you at inbox zero guy? Do you clear out your inbox every night?

SB: I don’t clear it out everyday but I do make sure that I reduce it down. I’m not one of those inbox infinity guys.

MR: I can attest that you’re pretty responsive most of the time.

SB: I try to be. It’s always going to get there. I’m always going to get there.

MR: I want to talk about some of this wisdom that you share on Twitter. We put together a few of the tweets that resonated with a few of us here at Founder Collective. I’ll read to you a couple of them and then maybe we can dissect the meaning.

SB: Uh oh, I wasn’t prepared for this.

MR: One of them said diplomacy is fine so long as it doesn’t compromise authenticity. Being truthful requires some necessary ruckus every now and again.

SB: That sounds like it was inspired being a big company, doesn’t it?   MR: Perhaps. Reminds me of some of my time at 3M. You have another one that goes on the process of getting agreement is developed/improved by managing disagreement. Find the value in discord.

You got another one where you talk about engaging with tension.

It feels like you got a little feistiness in your management style. It’s a little different than the way you carry yourself. You seem like a reasonably, easy guy to get along with. Are you a little more aggressive when it comes to your style for getting things done in the company?

 

 

This is Behance, easily the best portfolio site for creative professionals.

 

SB: I’ve always said from the very beginning of Behance that I love hiring people who feel comfortable with fighting. I also have always said that one of the greatest leadership skills I look for in managers, and also I try to do myself, is to fight apathy ruthlessly. If there are people on the teams that aren’t willing to fight it out. Fight that because, ultimately, when you are fighting something through, you are covering all of the design space of opinion. It’s almost like this multidimensional tug of war going all which ways. As soon as someone lets go and says, “You know what? I don’t care whatever you guys think,” that is when you screw over the customer because at that point, and going forward, no one is exploring that person’s design space of opinion.

I find conflict to be a very good thing. I also have a hard time with the patience and the process required for diplomacy. I actually recognize that politics are a reality in any team probably larger than 2 but at the same time, when you feel like progress is not being made because of an individual’s process to get there, it’s very frustrating to me. One of my challenges, especially working with larger teams, is to try to learn how to be diplomatic to the point of acceptable but also to ask the difficult questions, to call out the elephants from the room when they’re there, and be the person who just fast-tracks a lot of that ambiguity and lack of productivity.

 

 

 

MR: Were there any sources of conflict in the early days, sort of pre-Adobe, with Behance where either you saw a particular vision that wasn’t consistent with someone else on team?

 

SB: All of the time. It’s funny actually because I think about this. We were 5 or 6 years bootstrapped before raising money, and then really 7 years before the acquisition. I think the first 3 to 4 years of that, there was tons of tension because of the environment we were working within. We had very little money. Everyone was stretching themselves-hours, time, financially, in every which way. We had a lot of anonymity. No one really cared what we were doing. We were at those beginning stages where every decision had implications for the next few years of our lives. There were vehement disagreements and tempers and whatever.

 

The thing that we always did, though, is two things: One is we all weighed shared conviction at the end of every conflict. There was never a time where we would end a conflict or disagreement and anyone of us would resent each other or be like, “We should’ve be doing this.” It was always shared conviction, which is really important especially as a team grew.

 

The second thing is we had this belief that sometimes the company would answer our question, like sometimes we’re really debating things out and we just weren’t sure where to land. We almost felt like Behance as a brand or entity made it clear for us within 24 hours. I think that was because we had a very clear mission to connect and empower the creative world. We also had a very clear brand. We knew what we were about and what we weren’t about. I think having some of those things helps conflict resolve itself a little bit as well.

 

MR: It’s interesting as you’re talking I’m thinking about what’s going on at Reddit at the moment. Building a company is one thing where you build a product and you’ve got potentially some conflict between managers or functions, but then you throw in a community that’s got its own point of view and thinks of your product beyond probably even what the founders think of their product. I’m curious if the community of Behance users also played a role in this mix of what to do. I’m sure in a positive way because they told you the features they wanted but also it was yet another voice at the table that you had to be mindful of.

 

SB: When you’re in the business of communities, I always like to remind entrepreneurs as well as my own team that we are not owners of community, we are stewards of community. Because at the end of the day everyone can be deactivate their account and remove their content and we’ve got nothing. You are in the stewardship business. What does that mean? That means that you have to really listen. That means you have to proactively communicate. That means you have to manage expectations.

 

 

 

“I always like to remind entrepreneurs as well as my own team that we are not owners of community, we are stewards of community. Because at the end of the day everyone can be deactivate their account and remove their content and we’ve got nothing.” — Scott Belsky

 

 

 

 

 

 

 

It has a lot of implications for how you manage your business. We’ve always errored on this side of transparency and whenever we have screwed up. There was a time, like 1 or 2 years into the network being live, where we lost like 3 or 4 hours of data, I remember. It was early days. This was like 2007, 2008. We just couldn’t believe it. It’s the worst thing ever.

 

MR: Literally, contributors lost whatever they had put up?

 

SB: Yeah. Everyone who created a project to their portfolio in a 3 or 4-hour period was lost. We totally freaked out. This was so early days. We just didn’t have the systems backup and everything else ready yet.

 

MR: It was your fail-whale.

 

SB: It was our fail-whale. What we found is that when we emailed every single person who was effected, it was like 130 people or something, I personally emailed each one, explained in detail what happened, that we were really sorry. Not only did people come back, being like, “We understand and thank you for letting us know,” but they actually were encouraging to us, like, “We’re here. We’re like dedicated to, you know, helping you build this product. We love what you’re doing.”

 

It was like, “Whoa, we just built relationships with people as a result of being honest, you know, and basically screwing up and owning up to it.” Being a steward is what it is all about. As a team, when we’re really trying to figure out whether to go X or Y, oftentimes the community is the last decider.

 

MR: I’m curious how you compare or contrast your leadership style, given that you said there’s some inherent conflict in the early days of any startup, be it at Behance, and any early stage company, but with what it’s like managing at Adobe. You mentioned the difference between the big team but yet not wanting to be political, not wanting to play politics, that that gets in the way, and yet the teams have grown probably by orders of magnitude. How have you noticed your style has changed being in a big company from being in a startup?

 

SB: I’ve certainly learned that I like to just use this customer-first mentality, which seems obvious and is such a cliché. Of course, customer is first, but when you’re in business model conversations, oftentimes you can say, “Wait. What would the customer want.” It’s a really uncomfortable moment when you’re deciding whether to release something before it’s ready or not. “Wait, well what’s best for the customer?” It actually prompts some different conversations. I like to try to lead with that.

 

I try to say what I see. I’m a very hands-off manager for those people that I think are just specially productive and thriving. I get really in the weeds when I feel like there’s a disconnect between what someone’s doing and what I would expect of them or what the real vision is and how that maybe mismatches with their actions. I think some people would say I’m a very hands-off, like divide-and-conquer type of partner or a manager to work with. Others would say the opposite.

 

Teams large and small, you have to know how to get in the weeds with the right people to execute the right aspects of a product. That’s one of the other problems with big companies is you start to abstract yourself from the things that matter. What we know is that the future of business is great products. The future of great products is designed-center products. Designed-center products involved great designers who are actually crafting pixels.

 

If you’re not getting connected with the people that are making some of those little decisions that make a big difference, and that’s what design is, then you’re not doing your job. I actually try to structure my own teams at Adobe, which is a larger company, keeping some of the senior design leadership directly connected to me rather than having them further down some chain. I think that’s one of the things I’ve done a little differently and enjoy testing in the large company.

 

 

 

“I actually try to structure my own teams at Adobe, which is a larger company, keeping some of the senior design leadership directly connected to me rather than having them further down some chain. I think that’s one of the things I’ve done a little differently and enjoy testing in the large company.” — Scott Belsky

 

 

 

 

 

 

 

My friends who are entrepreneurs say to me, “Gosh, you’re still at Adobe. You’re an entrepreneur. I expect you to have been doing something new by now.” My attitude is actually I’m having a lot of fun trying to figure out how to build and change product within a large company. I do think that it’s entrepreneurial in its own way.

 

MR: The Behance team is still here in New York, correct?

 

SB: Correct.

 

MR: Adobe is based in San Jose.

 

SB: In San Francisco.

 

MR: In San Francisco, sorry. So, 3,000 miles away. Do you have an office at Adobe, like a physical place with your name on it in San Francisco?

 

SB: Yes. I have a desk in San Francisco and I have a space in New York. I try to split myself up every few weeks and also I’m soon going to do an extended stay in San Francisco and then come back for an extended stay in New York, so be bi-coastal for a little while.

 

I find I force myself to be more productive. I have less tolerance for meetings that go nowhere because I feel like every minute matters. When I allocate time on my schedule for a particular person or meeting or a project, I prepare. It forces me to be more efficient which I think goes back to your question about doing projects. Different teams at Adobe and even working with some teams outside, and I think it just prompts that level of seriousness and pro-active preparation.

 

MR: On the theme of management style, are there books or blogs or podcasts perhaps that you find are inspiring on leadership or good tools when you’re managing a team?

 

SB: Certain people like Seth Godin has always been a mentor of mine. In fact, he’s the guy who once wrote me a little note that said, “Keep making a ruckus.” That really stuck in my mind because I was trying to figure out, “What does that mean?” I think it means don’t get comfortable. Don’t get too comfortable. Don’t accept anything that is too comfortably either. Keep disrupting, in some ways. Oftentimes, when I sit back and see something happening that could just happen peacefully but isn’t optimal for the customer or just isn’t what I know should happen, that’s when Seth’s voice is in my head: “Keep making a ruckus, Scott.”

 

In Medium, I love some of the thought leadership that happens there where people take some time out of their day managing and being a practitioner to share some lesson they’ve learned and the story that goes along with it. As you mentioned, just following certain people like Aaron Levie and others on Twitter, always make me think about…Dave Morin in the product side. There’s certain people, like Dave once told me, the devil’s in the defaults. That’s something I always repeat with my teams on a product level because it’s so freaking true.

 

MR: It’s funny that you say that Seth Godin advice because it’s actually the advice I got when I was becoming a parent, which was teach your kids to be comfortable being uncomfortable. Then if your kids are able to be in uncomfortable situations and make do, they’re going to be fine. I think it’s great advice and I think it’s true in the business world as much as it is in life generally.

 

SB: Truthfully, if you’re managing a team and everything’s too comfortable, you’re probably not doing your job because a team always has to be competing with itself. The last product is your worst enemy essentially. You have to beat your last product because everyone else is copying your last product. You have to always be pushing, yourself and your team, that’s part of outperformance. If you’re just too comfortable, you’re doing something wrong.

 

MR: Another one of my favorite tweets that you wrote is, making simple is fucking complicated. You went on to say, “The more you have, the more you have to worry about. Another case for minimalism: minimalism is minimizing mental debt.” It sounds really good but what does it mean exactly?

SB: It means simple is fucking complicated because you always want to appease more customers with more features. Obviously, reducing things is really hard because you have a lot of great reasons for why things need to exist. Options, we are constructed to optimize for optionality, like that’s the nature of being human. You always want to have a backup plan, you always want to accommodate not only the first thing everyone wants to do but the thing that 30% of people want to do also. Maybe that’s the thing that’ll make my business succeed. Maybe this feature will win, maybe this feature will lose, like let’s just throw it in and see.

 

As you’re doing this, you’re causing your customers to have one more choice to choose from and basically 50% of the action will be on that secondary thing. If you have a third thing then it’s 33, 33, 33. Before you know it, four tabs and you only have 25% of your users actually trying to think that you think will move the needle the most. It’s like, “Gosh, you didn’t simplify it enough.” I see that all the time with new entrepreneurs and new products.

 

It’s really complicated. I like to say, killing your darlings. In writing, they always talk about how you have to kill those beautiful sentences that are just a little bit off the plot point where another analogy is like bonsai cultivation. You have to constantly trim back the most beautiful, newest branches in order to strengthen the base and that could actually make this a bonsai tree. When you do it, it’s hard because you’re like, “Oh, but that’s like the newest branch and it’s like, you know, it looks so cool and it’s a nice part of the tree.” No. Kill it. That’s fucking complicated.

 

MR: Does that come back to having a great designer? I know you think a lot about design. You talk a lot about design on Twitter and in Medium. You think about Jony Ive’s effect on Apple and having built this beautiful design that’s very simple that’s taking a lot of functionality and put one button on the phone. Is that where it comes from? Does it come from great design? Because all the product managers and all the engineers are going to want to keep adding features and functionality but somebody’s got to package it simply.

 

SB: An idea I always like to remind teams of is that user’s flock to a simple product. Then the simple product takes users for granted and then adds more features and then users flock to simple product. That’s the natural process that any product goes through. I think that no one designer is going to solve this problem because designers have a bias as well. We’re all drunk on our own Kool-Aid. It’s a process, like this is where it comes down to the concepting process. The role of design-minded people, the role of engineers with the more pragmatic set of realities and thinking, the folks who are driving and being stewards of the vision and the customer coming together, having a really great process that ultimately yields killing more things than they’re creating.

 

 

 

It’s amazing when I think about Behance in 2015, it’s actually a much simpler product than it was in 2010. We’ve killed groups, we’ve killed the tip exchange, we’ve killed all sorts of different ways of communicating and connecting because we just wanted to double down on one thing that really worked. We’re actually killing another thing pretty soon. It’s like this product is actually getting simpler over the years because our process is getting better. I think that can narrowed down to one person.

 

MR: I want to talk about a Medium post you wrote called The Interface Layer, which I think is really interesting. As venture capitalists, we probably see dozens of mobile apps pitched to us every week. You posit a different view or maybe a complementary view but basically that we’re moving to a place were the apps themselves don’t really matter and it’s more experiential. The apps are going to be connected on the backend via API and it’s more going to be about what you want to accomplish.

 

One kind of current example is in Google Maps if you want to go from point A to B. The subway routes will come up as an example. You can book an Uber right from the mapping app. Where does this go? Apple just announced that they are coming out with the Apple News which some people said Flipboard is now doomed. You’re an investor in Pinterest which has figured this out. You are also investor in Circa and they couldn’t find the right business model. I think wading through this is a bit complicated but maybe speak to where you see this going.

The Interface Layer: Where Design Commoditizes Tech

SB: I’m certainly thinking about this all the time. Learning a lot over the last few years of some of the companies you’ve mentioned, hard lessons learned or good lessons. Some of the facts are the full stack is being commoditized. Payments layer, messaging, all of the technology for the mobile experience on the database side, hosting, everything is being commoditized. Essentially, the distinguishing part of a product experience is now really the interface itself, that top layer. What makes that top layer extraordinarily effective? The simpler it is, the more integrated it is into your routines.

You want this to eventually, the interface that you use in your life should basically adjust based on where you are, what you’re doing, and what you’re thinking. You shouldn’t have to go into anything to do things that should all be there. That’s why I actually think we’re going to use fewer apps 5 years from now or 3 years from now than we do today. I think it’s going in the opposite direction now and you’re seeing that with some of the messaging products that are coming out where inline messaging, gives you all these things for commerce and whatever else. Although that has it’s own set of problems.

When you think about Uber and you think about what could potentially disintermediate Uber? Uber has APIs that are now available in Google Maps and you think, “Well, wait a second. If I have a map interface that manages all of my location activity and just click I need to get from here to there, whether it’s Uber’s API or another API delivering that service to you. “Oh, my goodness. Doesthat commoditized Uber? I hope not.”

When you start thinking about the power of interface, you really start to abstract a lot of choice and that customers see and a lot of the friction and everything else, and it gives rise to a new breed of businesses. What do we know about The Interface Layer? We know the designer’s rule there is because ultimately it’s a design problem that you’re solving. I think that you have to start thinking about what’s defensible in terms of the place where that Interface Layer exists, like Managed by Q, another one of our investments. They put in iPad in everyone’s office for people to request cleaning and office supplies and stuff.

What I see them doing is putting an interface that is locked on your wall so whether you thought you could use your phone for another app or go online or whatever, it’s actually always in front of you physically. It’s the ultimate interface is just like whatever you’re looking at any given point in time. I think there are a lot of businesses that are starting to figure this out. As an investor, I think it’s really interesting.

MR: It almost suggests the investor should not invest so much in these full stack, as you said, startups that are trying to do everything from deliver a service to take payment and all that, and actually abstract themselves one layer higher, and yet, as I listen to you, I think, Apple and Google and Facebook, they sure have the advantage. They are the types of products that people are using everyday, that know where they are, what they’re doing, what they’re thinking. I don’t know if I should be pessimistic for startups or optimistic.

SB: What the Interface Layer is doing is making it so startups can operate with much less overhead. Some companies are going to achieve all of that overhead, or they’re going to do all of the overhead. They’re going to figure out the logistics of matching cars with drivers, riders with drivers and all this other stuff. The question is, “Are other startups going to build on top of those stacks that don’t have to pay anything and just can take a dime off the top and basically just match and create a market for commoditized services underneath?”

It’s something that, I think, investors need to look for and think about and also the companies that have those stacks need to make themselves more defensive. Maybe they’re going to kill their APIs. I don’t know. Maybe they’re going to start to think a little bit differently about integrating with third party apps and stuff like that. It’s a good question. I think that the jury is out.

MR: One of the areas where were seeing The Interface Layer and I think you eluded to this, is chat and texting and this ability to use texting to call an Uber or to populate a CRM database or to do something in a much more natural language way than actually going into some software and filling in a form and submitting it that I could just text, “Bring me this kind of food,” or, “The meeting went like this.”

One can imagine doing quite a bit with a simple interface. You and I are both wearing Apple watches but I think the Interface Layer is going to be a key determinant as to how successful these devices are.

SB: Absolutely. The Apple watch is essentially a real estate play. It’s a screen that’s now physically on us and has our attention. It’s precious real estate. Apps and products and services that know how to effectively use all these new areas of real estate are going to succeed. As investors, it’s really exciting but you also have to keep in mind that the interface is easily disintermediated by a better interface and so it’s actually becoming a race to the absolute best interface which has a number of different implications in terms of what the actual technology is, what the design is, design standards, and also like augmented reality. What are the roles of all these new mediums are going to play, AI, in helping us get the product and service we want wherever we want it in the easiest way?

Stay In Your Overlaps

MR: I want to talk about my favorite Medium post that you’ve written which is entitled Stay In Your Overlaps, which got me thinking actually a lot about a thesis for investing. Your thesis is, I think, more of a framework than even a very specific thesis in how you select your angel investments. In the post, you talk about the intersection of themes and people. I think you mentioned that it’s this interface layer concept that you like meshed with careers of the future, sort of modern jobs.

SB: Promoting meritocracy.

MR: Then coupled with teams, founders that are designed-centric and have initiative over experience. In the Medium post, which I encourage people to actually read, you draw it out as if it were on a napkin. I’m just curious how you got there and how you operationalize that sort of framework.

SB: This actually became a framework for me as an investor but it really was the framework for me in terms of what I want to do with my career. It wasn’t as clear in the beginning so it’s gotten more clear over time for sure. The idea was, I feel like when people operate in the overlap of what genuinely interests them, what skills they have, and can easily possess and the opportunities that present themselves to them, that’s their zone of optimum impact.

If you’re working in two of the three, you’re not going to make the greatest impact that you could possibly make. Each of us in our own career, needs to make sure we’re working in that overlap. I remember all the stories about some of the companies that started like dry cleaning on demand because they thought it was a good idea and economics seemed to right. Then 6 months and they’re like, “Shit, we’re doing laundry,” and they realized it was never an interest of theirs and they didn’t want to be doing this for 5 or 6 years. Some of these companies folded and maybe some of them are going to succeed when people are actually really getting that industry and are into it.

We have to commit ourselves to be the things that we’re generally interested in. I have to be able to look at myself to companies I work at or companies that I invest in and make sure that I’m genuinely interested in them. Obviously, the role of design and interface innovation is really important to me.

I love the role of meritocracy as a force to a lot of new online products and services. I think that’s a healthy thing for ecosystems and can really make viable, succinct little businesses especially if they’re community-based. When it comes to teams, experience for obvious reasons is important, but the initiative over experience thing is really important because I actually find a lot of very experienced founders and teams that have all the right names on resumes and stuff but they just don’t have that level of drive and initiative that you know is necessary. I would trade experience for initiative any day. I would give up on people being as experienced.

That was the story of Behance. None of us knew what we were doing. We taught each other and learned the hard way and that made us into a really sticky team of great chemistry that actually, despite all odds for years, even for years after the acquisition, stuck together.

MR: Given this and given your very successful track record angel investing, what should a perspective company bring to you to convince you to invest?

SB: I love it when I get pitched around my areas of interest because also that means these are areas I can add value. When I come across a concept like Periscope, for example, Micah you remember because we all do this together, but they were a team that was thinking about something that I found really interesting. A lot of what they were doing and how they were approaching really matched that thesis. To me, that got really interesting. When I see a pitch or an idea that someone shares with me and it just creates 10 different more questions that I have, I know I need a follow-up conversation.

When I have a conversation and then the next conversation is exponentially more interesting than the previous one, that is like a really good indicator to me that there’s chemistry between me and the team because I’m like, “Oh, we’re building upon each other.” That means every conversation we ever have together, going forward, will actually build upon the previous one and which means this will actually become a valuable contribution I make. That’s what I like to see and feel. I’m sure you feel similarly with your investing.

Join our creative community by subscribing to the Founder Collective Newsletter!

MR: One question that gets asked a bit is what to wear in a pitch meeting. Nick Taranto, who we both know, who’s one of the founders of Plated, said the more he dressed like a hobo, the more likely the VCs were to invest. I don’t know if you’ve had that experience but you raised money from Union Square Ventures, one of the top VCs in the country admittedly you’d been working on Behance for a number of years. What should founders dress like?

SB: I think that founders need to feel very comfortable and confident in a meeting. The answer is really whatever makes you feel comfortable and confident. I think that when we put on stuff that isn’t us, when we act or dress or speak a certain way that we just don’t feel as native to us, it comes across that this person is not being who they are. As an investor, I think you’re like, “Is this not the a person, is this not the real person?” Because you get this vibe of discomfort. They say you don’t have to be in a club that doesn’t want you as a member type of thing. You don’t want an investor that doesn’t want to invest in who you are.

Whether you’ve got tattoos, this or that or however you want to dress, however you think, like that is you. I love WYSIWYG people. Those are the people that what you see is what you get, you know what you’re signing up for. I love it when people’s quirks come through in the initial meeting because I’m like, “Great,” like I know they’re first of all real and second of all I can manage that, like that’s going to be okay. Whatever clothing falls into this for you, I guess the answer to your question is if you’re meeting is on Wednesday, you should wear whatever you wore Tuesday.

MR: We talked a little bit about full-stack startups. There’s a trend towards companies disrupting very traditional categories like eyeglasses with Warby Parker; razors with Harry’s; mattresses, Casper. Their valuations, frankly, they’re exponential. It’s been amazing to watch. I’m curious what your take on that and whether long-term, these are good investments, whether you think there’s a fundamental shift going on in these categories or is it simply there’s just a lot of enthusiasm in these categories but it’s not real disruption. I know there are shades of gray.

SB: That’s why I have a problem with the term like that Warby Parker of this, Warby Parker of that because I think Warby and Harry’s, to some extent, are very different than pretty much every other company that’s making a product and having the “vertical integration” and the customer experience that they’re trying to build. The reason is because Warby and Harry’s, there weren’t many companies and factories in the world that made those products. They had to make deals and partnerships or acquisitions to actually have that beginning part of the supply chain locked.

Whereas, you see these Warby for houseware and Warby for sheets and bedding, and Warby for this and that. It’s like for all those, it doesn’t really click as much for me because I feel like there aren’t analogous like supply chain situations going on with those companies. I’m a little bit more wary on those than I am with the companies that I’ve actually started with something that was overpriced and tightened at the supply side of the market because it was just so hard to produce those items.

MR: Scott, do you have advice for makers and entrepreneurs?

SB: Yeah. I think that when I meet with aspiring entrepreneurs or people who make for a living and ask me for some advice half of the end of the meeting or something, there are a few things I always start with. First of all when people are starting something, you know that they really should make something that needs to exist and to value necessity over novelty. There are so many things in businesses that we see, some of which I made I mistake of investing in where someone just love the idea of a great product experience and they may have been a great product person but the world didn’t need another X. Just make sure you’re making something that needs to exist.

When I see teams who feel, as I said, too comfortable, it’s like if we’re not nervous, you’re doing something wrong. Striving for some level of discomfort I think is really important.

From a product perspective, I always like to remind my teams that the last mile of your experience building a product is the first mile of your customers’ experience of your product. It’s so important to remember that. We oftentimes, towards the end of something, rush to fit, get something out and oftentimes we’re forgetting the onboarding copy and the tour pages like some of these things that are actually the first mile of our customers’ experience. We need to make sure that we allow the time and energy to perfect that.

When it comes to taking a step back and thinking about careers and making big, important decisions, and stuff like that, a few things that I think are important to remember is that decisions made out of fear, lead to the status quo. When you are really trying to avoid something and you’re trying to stay clear of something, that’s when you regress to the mean. It’s also important, especially in early stages of a founder and the founding team to make sure you’re not making decisions out of fear because you’ve got nothing to lose at that point. You’ve gotta to swing for the fences.

I guess the last piece is beware the path of least resistance because the easy path will always take you to a crowded place. I see that a lot with other companies that start to be the X of Y or starting to do what someone else is already doing. Try to make sure that you’re doing something that is, in fact, difficult to do.

MR: I think it’s great advice because we’re in a moment now where a lot of people say to me and probably to you, “You know, it’s so much cheaper today to start a company. It’s so much easier to acquire customers.” At the back of my head, having been a founder several times like you, I think it’s still really damn hard. The journey, it’s not as glorified as Silicon Valley on HBO may make it seem. I think we’re in a moment where our industry is en vogue and it seems the hot place to be in yet. Entrepreneurship is still a really hard place. I think it’s a really satisfying place. I think people need to go in understanding just what it takes and not everybody does.

SB: Well said. The journey in between is a bitch. It’s all about optimization and it’s all about endurance. Those are two things that are not sexy but are pretty much all that matters because, ultimately, an idea is an idea, and a finish is crapshoot.

MR: Scott, thanks so much for coming. This is awesome.

SB: Thanks for having me.

Micah is a Managing Partner at Founder Collective.