#30 Book Summary: The Messy Middle - Lessons Learned as a Founder, Investor, and Bestselling Author | Scott Belsky, Author & Venture Capitalist

Scott Belsky is a modern polymath. He founded Behance, which he later sold to Adobe. He’s a Venture Partner at Benchmark and has invested in companies like Uber, Pinterest, and sweetgreen, and he’s currently the Chief Product Office at Adobe. We discuss the lessons he’s learned along the way, his investment methodology, and surviving the messy middle in any ambitious endeavor.
Last updated
August 14, 2023
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Scott has been named to Fast Company's list of the "100 Most Creative People in Business."
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#30 Book Summary: The Messy Middle - Lessons Learned as a Founder, Investor, and Bestselling Author | Scott Belsky, Author & Venture Capitalist

“Great opportunities never have ‘great opportunity’ in the subject line.” – Scott Belsky

In this episode of Outliers, I’m talking with Scott Belsky (@scottbelsky). After starting his career at Goldman Sachs, he left to found Behance which he later sold to Adobe. He’s now the Chief Product Officer at Adobe as well as a Venture Partner at the world-renowned venture capital firm Benchmark. Scott was an early investor in Uber, Pinterest, Carta, Flexport, Airtable, and sweetgreen. And finally, he’s the best-selling author of Making Ideas Happen: Overcoming the Obstacles Between Vision and Reality and The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture.

Scott is a modern polymath. We explore his journey from entrepreneur to investor, how he approaches investing in early-stage technology companies, as well as the lessons he’s learned at Benchmark, Adobe, and Behance. 

Chapters in this interview:

  • 00:00:05 – Scott’s learnings from his start at Goldman Sachs
  • 00:05:35 – On co-founding Behance, and attempting to manage the “most disorganized community on the planet”
  • 00:09:15 – Tactics for entrepreneurs and their teams
  • 00:13:26 – The transition from startup (Behance) to large company (Adobe)
  • 00:16:29 – How the desire to buy an education led to Scott’s interest in investing
  • 00:18:59 – Seeing an investment grow from Seed to IPO
  • 00:22:47 – How design can move the needle for a business
  • 00:28:21 – Scott’s foray into venture capital and finding his ideal role melding investing with company-building at Benchmark
  • 00:34:04 – On writing Making Ideas Happen and The Messy Middle
  • 00:39:11 – Startups avoiding the fate of the “one-hit wonder”
  • 00:43:32 – Investment trends that Scott is focusing on
  • 00:47:31 – Scott’s favorite failures

For more explore the transcript of this episode.

Links from the Episode

Scott Belsky's Books

Key Takeaway

There were so many great quotes and ideas in this interview, but we really Scott’s advice for entrepreneurs, including:

“I've always viewed feedback as a form of compensation. And when I don't get it, I ask for it. It's gold to me—and even if I disagree with it, it's still a reality, because it's how someone sees me as an entrepreneur or a product leader in a big company.”
“Great opportunities never have 'great opportunity' in the subject line.”
“Oftentimes, the cost of getting attention is that you're no longer paying attention.”


Daniel Scrivner (00:00):

Scott, it is a huge honor to have you on Outliers. So thank you so much for joining me today.

Scott Belsky (00:04):

Well, thanks for having me.

Daniel Scrivner (00:05):

So I want to have a little bit of a different conversation with you. And as I have watched your work and I've watched her trajectory evolve over the last 10 plus years, to me, you're a great example of a modern polymath whose am sure is like an awkward title, Put on you because you're an investor and entrepreneur, you're an author. So I want to explore that. But what I thought would be great to start with is if you can just share for people listening that aren't aware of your kind of work and what you've done, if you could just share a quick high-level sketch of your trajectory for Goldman Sachs on.

Scott Belsky (00:37):

I find that I am happiest when I feel full utilized. And part of that for me is personal with my family. And part of that is advising and helping other founders in their journeys because I find that I'm deeply curious, interested in some of the problems they're trying to solve and also how they build their teams. I also by day love operating and building products and teams myself. And I learned the hard way that when I unplug from that responsibility, I feel a little depressed.

Scott Belsky (01:03):

So some combination of these things, I guess, that has brought me to where I am. But after having an undergraduate experience with an interest in environments economics and design and business, et cetera, I cut my teeth at a Goldman Sachs and realized very quickly I wasn't cut out for finance, and then ended up in another job there that I loved. And it was basically around organizational design. It was a small team and executive office that focused on advising leaders in the firm that were having struggles with their businesses, going into clients and helping them deal with growth challenges. And I ended up realizing in that role that I love building organizations or watching how organizations could be built. And I also realized that I love using design to do it. I was actually one of the, probably only people at Goldman Sachs with Adobe Illustrator installed on his computer because I just found it a very effective way of communicating as opposed to Excel spreadsheets and Word docs.

Daniel Scrivner (01:59):

Yeah, I can't imagine an organizational structure in Excel. It's terrible. I'm curious. Talk a little bit about, it sounds like you, in that role of organizational design, that you probably worked with a handful of different clients. Can you share a little bit about the types of clients you worked with? And I'm also just curious, it seems to me when I look at your trajectory and look at it starting at Goldman Sachs that that seems very formative. So I'm curious also just broadly what you took away if anything from the culture and team and environment at Goldman Sachs.

Scott Belsky (02:27):

Sure. And we're going way back because I left Goldman back in 2005 or 2006. But what did I learn? Well, it was at the time a culture that really values leadership development. And was so intentional that the firm would actually give stretch assignments to high potential VPs and managing directors where they would be given a project somewhere else in the world, some role that was actually more so for their own development than for the firm's benefit.

Scott Belsky (02:56):

And yeah, it was a nice way of having some innovation potential that may or may not pan out to be a new business. But the conviction was that our development as leaders, 70% of it happens through experiential education, 20% of it happens through coaching, and 10% happens in the classroom through formal instruction. And so it was a really great course into that 70% and how to be intentional about it both for others, as well as for my own career.

Scott Belsky (03:23):

And in terms of the types of problems that I was staffed on, it was all kinds of crazy stuff because I was the most junior guy in the team. So I was asked to develop the leadership decision-making compass that Hank Paulson the CEO at the time ran everyone in the firm through, to being the writer of the script for the Annual Holiday Partner Video, to coping into some hedge funds that were wondering why their cultures were so bad and didn't want to engage any third-party consultant because of the confidentiality issues, but would come to Goldman as their prime broker, and then would open up the organization to us and I was like, "Wow, no wonder this place is a nice show." There's no great leadership or thoughtfulness around a development here. So I just learned a ton.

Daniel Scrivner (04:05):

I love that framework that you shared of 70% experiential, 20% being coaching, 10% being learning because it harks on something I think is deeply tragic, which is this idea that a lot of people have that you go to school for four years or six years or eight years, and then you're set for life and you no longer need to learn and you no longer need to engage, you don't really need to improve. And I'm guessing you've taken that lens and you've likely worked with a handful of coaches along your career. Can you talk about the kind of experiential side of your development in any coaching that's been just crucial for you?

Scott Belsky (04:33):

I've always viewed feedback as a form of compensation. And when I don't get it, I asked for it. Probably not enough, but whenever I get it, it's gold to me. And even if I disagree with it, it's still a reality because it's how someone sees me as an entrepreneur or a product leader in a big company. You're always trying to develop and share a narrative and generate alignment with your teams. You can plant a vision or an idea.

Scott Belsky (04:59):

But to get everyone aligned and to get everyone to feel like they're owners of it, and you really have to tune into everyone's frequencies. And the only way to do that is by getting data from others as to how you're coming across. So in fact, I would say that the biggest insecurity I have as a leader in a big company is The Emperor's New Clothes, "Fear." Is there something that I am doing or not doing that no one is telling me because of my position in the organization? How do we overcome that? I think it's a very active measure of asking for feedback repeatedly in developing a culture where people exchange that more liberally.

Daniel Scrivner (05:35):

Moving on to Behance, and I want to spend a little bit of time on this part of your story. But I'm curious, so you have this four years and change experience at Goldman Sachs, and then you go on to found Behance. Was there an insight? Was there a trend that you saw? Was it just meeting the right people? What was the impetus to founding Behance?

Scott Belsky (05:54):

There are a couple of quick things that I would note. Number one was, a lot of the people that I found most interesting in my life and my close friends were creatives. And they always seemed like their careers were at the mercy of circumstance. Many of them were hired by head hunters to work for agencies, to work for brands. Many of them had outdated portfolio sites. Many of them never got attribution for the work that they actually did in the world. And you would have to know that they did that billboard to know that they had a role in it. And it just felt like, "Wow, some of the people were the most potential and most talent in the world." The people literally make our lives interesting and compel us to take action on anything around us and understand the world as it's happening are also the most disorganized community on the planet.

Scott Belsky (06:37):

At an existential level, Behance's mission was so organized the creative world. And of course, when I told people that and they were like, "Oh good luck with that." But in a practical level, an insight that really made the Behance work was that up to that point, portfolio sites were websites on people's domain names out in the Ether. And the only people that would discover them were the people who knew those people were got their business cards at the time. And how about like discovery of talent you didn't know existed, which is obviously the bigger opportunity?

Scott Belsky (07:05):

And so what Behance did is, it deconstructed the nature of a portfolio into a series of projects. Each project with an incredible presentation of the content in itself so it could live on its own with metadata and ability to find and if you found an incredible piece of work because you were searching for people who did work for Nike or whatever, and then you clicked on the person's name and landed in the portfolio, it was inverting the funnel of how creative talent was discovered. And that ended up being a 10x better way for creatives to build their careers. And whenever in technology you crack away of 10x-ing something that is indispensable in an industry, to me, that's where you can build a real company.

Daniel Scrivner (07:42):

I wholeheartedly agree. And later on, I'm going to share a little bit of my connection with Behance and share thanks to you because Behance in a lot of ways helped kicked off my career. But I'm curious, so you start off on this trajectory. I agree, the problem sounds really big, but it's not necessarily linear. And I know that you went through your own valley of despair, messy middle building it. Talk a little bit about that part of the process you set off on this exciting journey and you find yourself in the middle period of it. Any lessons learned, any advice you would give to other entrepreneurs struggling with that?

Scott Belsky (08:14):

Sure. Well, the beginning of a journey is always extraordinarily exciting. You can get people to quit their jobs. You can quit your job yourself with this notion of what the world might look like in the future and how you're going to make it so. And then of course, reality kicks in and you realize that it's just endless ups and downs. It's just tremendous amounts of volatility. Sometimes you feel like you're onto something. And then you're humbled by the fact that the guy selling fruit at the corner, it has more revenue than you do. And who do you think you are being a business? It's very disconcerting at times. You're working amidst anonymity, ambiguity, uncertainty.

Scott Belsky (08:48):

And so there were some loss years of Behance. As you may know, we were bootstrapped for five years. Venture backed for two years. There were at least a couple of years in there where we were just going sideways. I call them the last years of Behance and there were reasons for that that were largely my fault, but keeping the team together long enough to figure it out, building a culture, merchandising the progress of the team, even when there wasn't much to celebrate yet. And these are all crucial ways of just sticking together.

Daniel Scrivner (09:15):

That last year period, that strikes a nerve with me because I've invested a lot of companies. I've observed a lot of entrepreneurs. And it seems to me like there's these tick and tock cycles of building a company where an entrepreneur is able to contribute at a level. Then the business may be grows beyond their ability to contribute and have an influence and the entrepreneur has to catch up and work on themselves and up-level their skills. And it seems like in a lot of ways that kind of entrepreneur or that leadership team can be a gating factor on progress. And I'm curious, in those last years, part of that is obviously keeping the team motivated, but a bigger piece of that is just keeping yourself motivated and balancing out your emotions and keeping a positive outlook. What was your tactics? What was your approach to being able to do that?

Scott Belsky (09:57):

I've always gone between whether a startup should be more of a sport's team mentality or a family mentality. At sport's team, everyone has to be at their best or you can. You have to pass the ball, everyone has to be a participant. Whereas family, you put up with that drunk uncle every year, even though he's part of your family. So everyone has a little level of tolerance for each other. And in our instance, the family aspects of Behance kept us together because there were certainly periods where none of us were qualified to do the work we were doing. And in some way we made this commitment in one another to build each other into the roles we needed to be. And in some cases, step aside and hire people more talented than us in certain functions. So I think that was a key part of it.

Scott Belsky (10:41):

But practically speaking, there were a lot of tactics we had. And I think one of the most important things as I look back was the ability to short circuit our own reward system as a team to keep ourselves engaged when there wasn't a stream of traditional rewards like salary or members or big press releases, et cetera. And we had all kinds of fun things. We would make bets with each other of things that when they would happen and the winner would have to do something bad or get something good. We had all kinds of fun games that we would employ at the time.

Scott Belsky (11:10):

And I also, as I look back, I think there were a lot of moments where I retold the story of what we're doing and the progress we're making and where we're going. And the analogy I've come to use is, it's like driving your team on a cross country trip with the windows blacked out and everyone at the backseat not knowing where they are or whether they're making any progress unless you merchandise it to them. And that was another critical thing I did often.

Daniel Scrivner (11:34):

I'm curious when you put on your investor hat and you're working with one of the companies you've invested in or maybe it's just an entrepreneur you're advising or coaching and they're in that messy middle period themselves because I think this is something that a lot of people... I think is just frankly, not covered, not talked about, but this happens in almost every startup company continually for multiple times in its trajectory where there is this messy middle period where they've had a big breakout. Now they're trying to figure out where to go from there. So when you have an entrepreneur you're working with that's in a period like that, what's your advice to them? What do you think is helpful in that role?

Scott Belsky (12:07):

The questions I get at range sometimes it's the question of, should I quit this or should I stick with it? Because it gets hard and you're always asking yourself whether you admit it or not, like is this going to work and should I quit? And I think that this old adage of winners never quit. It's not necessarily true. As we know from pivots and from stories of other entrepreneurs that the best thing they ever did was quit something.

Scott Belsky (12:28):

What I oftentimes ask them is to remember the level of conviction they had in the beginning. When you started and you saw the world in a certain way, you had a lot of conviction, even though you didn't really know much yet. You hadn't talked to customers, you hadn't developed product, you hadn't done betas and whatever else. And then now, after all you have learned, things that have worked and not work, but more importantly, what you've observed, do you have more or less conviction in that end state?

Scott Belsky (12:56):

And a lot of entrepreneurs who are still in their messy middle will say, "Oh my gosh, this has to exist. This is a problem. I'm sure of it." And to those entrepreneurs, I tell them this is par for the course. You're in the messy middle, stick with it. This is what it's about. Gain confidence from the doubt you're getting from others and consider yourself lucky that it's so hard to get this right because it will be a moat when you're in market. But sometimes entrepreneur says, "Honestly, I have less conviction." And I say, "Well, then quit. Do something different for sure."

Daniel Scrivner (13:26):

Do something where you've got more conviction and you're ready to go. But I love that advice. I've actually never heard it framed that way. But yeah, traveling back in time, remembering that conviction you started with and updating that in real time. So then you end up selling Behance to Adobe and adjoining Adobe for a period of time. I'd love to talk a little bit about what that kind of experience and transition was like for you? Obviously you're going from being an entrepreneur of a smaller business to joining a behemoth in a lot of ways, and your role changed a lot. And I'm going to know was partly involved around the creative suite. So what was that transition like? And what'd you take away from that experience?

Scott Belsky (14:01):

Well, it was certainly a moment where I wasn't sure how I would adjust. I'd always been completely in control of my own destiny. Part of the success of a startup is like cultivating a well, oiled immune system where you can tell if anything is off. And there's a lot of control associated with something new like that as opposed to a big company where you have thousands of people around you, and there's no way everyone can be aligned at all times. In fact, some percentage of the companies' always misaligned. That's just the way it is. It's just not possible to get everyone on the same page in the same moment. That took adjustment.

Scott Belsky (14:34):

But what I was excited about was first of all, the reach, this idea as a startup, you wish people were in the top of your funnel knew who you were. And as a big company, it's like you've got everyone there and they know who you are and it's yours to win or lose. I also really enjoyed fighting the bureaucracy to some extent, the things that were inefficient. I felt like I could be an entrepreneur in an entirely new way by innovating around something in the organization. And I think that those folks are very precious in a big company because they're the future. They're the future of the better norms, the better practices, the better way of doing things. And if you don't have those people, you all regressed to the mean and ultimately end up simply resting on your legacy.

Scott Belsky (15:13):

And Adobe when we transitioned to a subscription offering, but still had the same old desktop products, we were at risk of doing that unless we innovated with things like Cloud documents and mobile creativity tools that were connected to the desktop ones and integrated funds and services, et cetera, et cetera. We had to level up, otherwise our transition was not legitimate. And I think it took us years to get that done. But as an experience of being a leader, I learned so much more than I anticipated.

Daniel Scrivner (15:42):

I know now you're the Chief Product Officer. So obviously you're spending a lot of time on the product side. Was that true in your first entered in Adobe?

Scott Belsky (15:48):

No. So I entered initially only overseeing Behance, which was the asset that Adobe purchased in late 2012. And then about a year or so later, the leader I reported to at the time said, "Listen, we have this nascent thing called Mobile and we haven't figured it out yet. Do you want to take it on?" I was like big point where I choose to just move beyond the thing that I had made. And I was really excited about it because it also opened up a Pandora's Box of questions around, well, if you have a mobile product, how does it connect to the desktop product? And then you need services, and what are those services? And they ended up realizing there was a lot more to it. It was a great experience. And I think also helps retain my team and I because we started to have steep learning curves again, which was really important.

Daniel Scrivner (16:29):

It's the importance of steep learning curves, especially if you've been working on a problem for a long period of time. I'd love to switch tacks and talk a little bit about investing. And as you've made, you've been prolific as an investor, both as an angel, as well as by being a part of Benchmark. And your portfolio, you've got some incredible companies, whether it's Uber or Sweetgreen or Flexport. And one of the things that I was curious about that is, obviously for anyone that's an entrepreneur, I think part of that naturally becomes you want to pay people supported you in your journey. You want to pay that back for other entrepreneurs. And maybe that played a role in why you started making investments. Was there anything else to that story? What was it that just fascinated you and drew you in?

Scott Belsky (17:08):

It first happened a little less altruistically and a little bit more around wanting to buy an education frankly. It was 2010, I was five years or four years into Behance. I probably had no business really investing at the time. And I was introduced to this guy who had just left his job at Google to start a company that was also focusing on the creative world to some extent and had like a very grid-like pattern to its product experience, which was similar to Behance at the time. And he had another name for his company at the time, but it became Pinterest and this has been Silbermann.

Scott Belsky (17:42):

And so I had this meeting with him before he was raising his first seed round and really resonated with him and his vision. At the time, there were products like Delicious and others that were bookmarking products. And he really had this vision for a visual interest in showcase and discovery site. And I actually felt like I could learn a lot from him. He was from the West Coast. I was from New York. And of course, I had this insecurity being outside of Silicon Valley and not having a network out there. And so in some weird way, I said, well, listen, I'm going to be an advisor for his business. And I'm also going to invest in in some ways by an education and a network at West. It was maybe my rationalization at the time.

Scott Belsky (18:19):

And I ended up having a great experience learning from him in the early days and trying to help however I could. And then of course, when you have an investment that yields a very large team of people who ended up going out and starting their own companies, they go back to the same angels that were helpful in their previous company. And so what I've learned in the investing space is really to stick to my lanes. It's like I'm a product and design obsessive. I love jumping in and helping teams with their product experience, their onboarding, their first mile experience, the engagement patterns, and building and scaling a design and product team. And I feel like companies that I really love and founders I resonate with, I would love to serve that role.

Daniel Scrivner (18:59):

So obviously with Pinterest, it sounded like you ended up investing very early in the stage of that company. And that company has obviously gone to grow immensely. It's now a public company. It's done really well as a public company. And it's not the only example in your portfolio. I know Uber is another example you invested super early. So for someone listening that maybe hasn't had your purview of being able to invest early and truly seeing just how much time it takes to build a sizeable business and bring this vision to life, can you share a little bit about what that's like to get early glimpse at something where you're just as excited as the founder of what this could become, and then see the ups and downs all along the way to that getting realized?

Scott Belsky (19:34):

Well, a couple things. First, great opportunities never have great opportunity in the subject line. None of these were obvious. And in fact, after these investments, I and other investors in these companies, I can factually tell you, thought they would be zeros in both Pinterest and Uber at certain points. It's just because of the ups and downs of the economy and also the spaces that they were in and their lack of ability to monetize and periods of low growth and competition, et cetera, et cetera, regulatory issues with Uber, for example. There were many moments where it was a very unclear. You can't become lazy and look for obvious signals. And that's when an investor is telling me, "Oh, I saw really a great signal." I'm like, "I don't resonate with that because it's never clear for me." What I do zero into, though, is really a product that I think is 10x better experience in something that I do and identify with or can get empathy with some other set of customers doing.

Scott Belsky (20:32):

You talk to a founder and every conversation is a step function more interesting than the one before it, it's a signal to you of the type of person that they are. I also love investing in optimistic pragmatists, people who are very optimistic about the future, like anything's possible, but also somewhat practical and pragmatic about the present. "Oh no, we're not moving fast enough," or, "This data set, I'm not sure we're able to going to sufficiently build that. And I don't think our AI effort will be as effective as we may have thought." That's a very rewarding type of partner to work with. And so as a board member, as an employee, those are the people you want to work for.

Daniel Scrivner (21:08):

I love that quote, "investing in people that are optimistic pragmatist" because I think that that's the sweet spot to get into where obviously someone can see something that's not yet here and be able to build it out, but it's also extremely practical along the way. And I'm curious from those experiences, have you drawn any parallels? What helps somebody, because I know a lot of people who are very optimistic, I know a lot of people who are very practical and I don't know of many people that are able to knit those two together, what is the superpower there? What is the ability there to knit those two things together?

Scott Belsky (21:39):

There's a talent to see how an end state will be and to have inherent optimism about what could go right is a special skill. And in fact, I think it's one of those that makes you a great founder and maybe not a good investor. The best full-time investors, traditional investors that I know are really good at picking apart what will go wrong always. As a founder, you're never going to get past go if that's your mentality.

Scott Belsky (22:02):

But at the same time with the optimism and the desire to market it and spin a narrative and get people excited, et cetera, you have to have this bias towards action. Nothing's ever getting done fast enough. The world is always moving faster than you. Competition is always at your back if you're doing something important. And so facing those realities and also never putting lipstick on a pig type of thing, when something goes wrong, you always have an option. Either make this look better than it is to your team and your board and blunt the blow of the bad news, or be very forthright and say, "This is exactly what we're up against and I need help." And everyone is in that instance at some point, but it depends whether they're honest about it or not. And so I just think that that's the killer combo.

Daniel Scrivner (22:47):

So you talked about the lens, you're staying in your lane in the lenses that you use of being product-focused and design-focused. And one thing I wanted to explore with you is the kind of lens you apply when you're looking at a company that you think has incredible design, and that could be you think they have an incredible design culture, maybe that resemble something like Airbnb. That could mean that just the product in and of itself you think is incredibly well-designed?

Daniel Scrivner (23:08):

And what I'm curious to understand a little bit is, I think a lot of designers don't actually know what's valuable and what's not valuable in terms of bringing design and building design is a competitive advantage at a company. And I think a lot of people get confused with that rebranding is adding a tremendous amount of value, when it's not. So I'm curious, when you're looking at a company specifically through that lens of design, what to you is kind of design that's not moving the needle and what to you is design that's truly moving the needle for a business?

Scott Belsky (23:36):

I'll talk about it from a product perspective and also from a operating strategy perspective. From a product perspective, I very much look at a product and I think its object model and the level of thoughtfulness that someone put into helping any user of that product know exactly where they are, what they're supposed to do, and what they're supposed to do next at all times. And underneath that, there are a lot of implications, whether it's the breadcrumbs of understanding how you got to where you are in the product, always knowing where home is, getting that safety, not getting lost, some redundancies in the product to catch people where they might look based on familiar patterns they have with other products. There's so many things under the hood that are required to achieve a great object model. And I think that in order to do that, you have to have a great design and product sensibility as a team. And I also believe that that's a really big competitive advantage in many industries, especially those that you're trying to disrupt that have inefficient poor product experiences.

Scott Belsky (24:35):

So I really try to tune into that. And that's why when a deck doesn't have a product to walk through, I just can't resonate with it. And similarly, when I meet with my teams at Adobe, I always push for product first because we need to ground ourselves and where we are and what the user's experiences. Another thing I've been trying to push for at Adobe is recognizing that our customers are not just living in a product like Photoshop. They have an end-to-end experience across our products. And so how do we really take that into account as opposed to just think about a customer from a product by product perspective?

Scott Belsky (25:07):

From an organization level, though, real quickly, in real short, a prototype is worth 100 meetings. You can have a meeting and has not and talk about what something should be. But when you walk people through an end-to-end experience for an objective that you have to change something at the business, it's like a pot knife through the butter of bureaucracy. Everyone suddenly gets aligned and it's a beautiful thing.

Daniel Scrivner (25:29):

There are a lot less different interpretations when you're all going through the product together as opposed to just some sort of a narrative or some sort of a nice deck. And I love your model of object or orientation as you think about product. And one thing I was curious is, just looking at some of your investments, clearly you can bring that lens to something like Airtable or Uber, but you also have investments like Sweetgreen in your portfolio. And I'm curious, when you have something that's maybe more in the real-world slightly out of the realm of digital and out of product, do you still approach it very similarly? Do you use that object model, or is there another model or another kind of screen all together?

Scott Belsky (26:03):

Yeah, well, Sweetgreen's a great example. It's a company that I sat on the board on as well and helped with their digital experience. But what I loved about that team is that, they really think about the end-to-end experience of their customer. And the challenge to me was that they think about it both in the physical end of the digital world as one seamless experience. So I felt like I had a lot to learn from them. They also think about an experience, including the quality of the product itself, which has implications behind the counter, as well as in front of the counter.

Scott Belsky (26:34):

I remember spending a whole day with those guys and an incredible industrial designer I knew going through new salad bowl concepts. How could a salad bowl be both recyclable, eliminate the need for washing metal bowls in between salads and improve operations and efficiency and cleanliness? It felt like it would be entirely different, but actually it's the same thing. Digital... I think that we as humans really discern too much between atoms and bits. At the end of the day, it's all something that's happening in our brains through light projected into our eyes. And whether it's coming from natural light or artificial light, it's all an experience that we're encountering.

Daniel Scrivner (27:11):

It's a very meta perspective. I love that example of spending a whole day looking at salad bowls because all of the design-focused companies that I've worked at that have moved the needle, including Apple and Square did things like that. I remember when I was at Apple, we took a tour of the industrial design lab there and they had this whole... It was an insane amount of real estate that was dedicated to all these different prototypes of the lighting mechanism that would be behind the Apple logo on stores. And they were trying to find the right hue of, is this too yellow? Is this too white? Is this not bright enough? Is this bright enough?

Daniel Scrivner (27:42):

And then I remember at Square at that same level of attention to detail, we would look at 10, 15 different industrial prototypes of different square readers with different affordances, different sizes, different form factors. I think anytime you're with a team that spends that level of detail on something like that, I think you just really care. That resonates.

Scott Belsky (28:00):

I think it's a great point. And I've always turned over what the actual definition of design is, which just seems like a very cliche question. But my latest view is that it's the small things that make a big difference. You have to have a group of people that care about those little things that ultimately makes people feel something they can't even describe. And it's these little things that make a big difference.

Daniel Scrivner (28:21):

I love that too because it also seems very uniting between, I think a lot of people are like, "Oh well, here's product and here's design." And it's like, "No, it's all the same thing." And if you care about those little details that move the needle, you're going to apply. I think that same ones to the product, which is super interesting. I want to spend a little bit of time talking about Benchmark because I think obviously as an investor, as someone who's interested in the investing space, Benchmark is an incredibly iconic firm, I think for a lot of people. And so I'm curious what brought you to Benchmark and if you could just talk a little bit about the culture and values and what it's like to actually be on that team?

Scott Belsky (28:55):

I've been at Adobe for three years. I've been at Behance for seven years before that. So I was 10 years into my role building products in the creative industry had circumstantially been involved with a number of companies and as an investor. And it made a mistake, which was to think that everyone telling me I should do something means I should do it. I was being told by my friends that, oh, you should be an investor. That should be your next thing. And of course, grass is always greener. At the time, operating, leading teams, products, product launches, big meetings, the idea of doing something different was as appealing. And so I took the leap out a tremendous amount of respect for brand at Benchmark and the partners and their track record, et cetera. And I figured what better place to jump in and commit the rest or the next part of my career at least to being a full-time investor in venture capital.

Scott Belsky (29:45):

And so I hung up my spurs and I quickly learned that the things that I love doing most, like thinking about the potential of a product, the potential of a team, before it's obvious that there's traction and really also spending a ton of time that may not be an economical use of time in the world where you have to see a lot of volume of teams and really travel the world constantly. I missed that. And so I saw it, my partners saw it. I tried to make it work that the notion of you can't quit, you got to make it work certainly crept in, but it just became so clear to me this was not going to be a great outcome for me in my career. I didn't want to look back 10 years from now and feel like I could operate so quickly.

Scott Belsky (30:25):

And so the firm was extraordinarily gracious and saying to me, "Well then, what well would you want?" And I remember building a little clip document of the role that I had in mind and my partners were super supportive and remain connected to the firm, remain in LP, et cetera. And now I'm really happy that I have to have a hybrid of both building and investing. I feel like to the point of feeling fully utilized and thus happy, that's what works for me.

Daniel Scrivner (30:48):

Hey, I'm curious. I want to ask two closing questions to close out this investing part of the conversation. And one of those is, you talked about obviously what got you into investing in the first place was wanting to get an education. So now we're fast forwarding to today, how has that played out? And in my end, the reason I want to ask this question is, there are a lot of people who are investors who have been an operator. There are a lot of operators who have also been invested at some point in time. I think it's becoming more common in smaller angels, but there are too many people that are able to knit those together really well. And I see those as very reciprocal where you learn a lot as an investor, referred to it as being a scientist. And you have all these experiments running in parallel and you're able to observe differences in what's happening in each of those and learn and apply those. What's your view? And how has that kind of education impacted how you operate?

Scott Belsky (31:33):

I find it extremely valuable for me to see how the next generation of teams are making their products. What design tools are they using? What collaboration tools are they using? What are their work practices? What are their work from home philosophies and how were they dealing with the pandemic? I observe all of this in little pockets of time during the week or oftentimes a weekend. And then in my day job as a big company, we're tackling on many of the same issues. And this actually gave me the Cardinal Rule that oftentimes when you're trying to solve a company, rather, oftentimes you're trying to solve a problem in a big company, the answer is like, what would a small company do? So I asked that all the time and I get a front row seat in this investor advisory role.

Scott Belsky (32:13):

So it really works for me. Of course, I'm ruthless about my time and my priorities, et cetera. It's kept me on my toes. It's taught me more than I can explain. And it's extraordinarily rewarding. At this point, it also is giving back. There are many investments that I do where it's like, "Listen, I am doing this because I love the entrepreneur. I love the problem. And I don't even have much financial exposure to it, but I just think it's such a great journey to be a part of."

Daniel Scrivner (32:37):

I want to ask one more question. The answer may be very similar. But one thing that I was really curious to ask you is, I think when a lot of people think of an investor, they think obviously the main motivation is financial. And sure, obviously you hope when you make investments that these turn out to be valuable enduring companies in a lot of ways. And I think a lot of investors care more about the outcome for the company overall than their own personal outcome, but clearly there's that element.

Daniel Scrivner (32:57):

But I imagine that for you, it's much deeper and much more emotionally resonant of why investing is so interesting. So I think part of that's backing entrepreneurs, but if we put the money part aside, put the learning part aside, what's at the heart? What warms your heart when you're looking at a pitch or when you're backing an entrepreneur that makes it a deeply rewarding emotional experience for you?

Scott Belsky (33:16):

It's so exciting to feel like you have a chance to be some part of the future. Something very material and impactful. I don't know if the driver is ego or the novelty of being alongside that journey and seeing the inner workings of a problem being solved. It's probably a combination of all these things, as well as the friendships that you make along the way. And yes, the ability to look back at your life and say, "Wow, like I had a small little microscopic role." Maybe I introduced to the key person who'd built the design for them or whatever the case may be. But that is extraordinarily rewarding. I've learned it's actually part of what motivates me in my career. And when one of those investments works, to me, it's like, how do I put that capital back into the system and really be very long-term oriented about it?

Daniel Scrivner (34:04):

So I'd love to transition and switch the conversation to talk a little bit about your books and how you approach writing. And for people that haven't read them, you've got two incredible books. I've read both of them. They're near and dear to my heart in different ways. And funny enough, I read them at different points in time where they were super resonant for me. The Messy Middle I read cover maybe a year and a half ago when I was in my own messy middle. And that was literal I could not find really anything that I felt could help me get through that experience emotionally because it can be very challenging. And that book was it. I'm curious if you could start by just sharing a little bit of the backstory and the core idea in each of those books?

Scott Belsky (34:40):

Absolutely. And I'll start by just saying that the reason I write is because it's also my way of remembering the things that I'm learning from others and synthesizing it. I've always felt like writing is, for me, at least the most effective form of self discovery. And it also helps connect the dots with your community because whenever you share something, people then have more to talk to you about.

Scott Belsky (34:56):

With Making Ideas Happen, this was back in writing started in 2007, it was the early days of Behance. And as we were trying to organize the creative world, I focused on, who are the most productive creative individuals and teams out there? And why are they especially productive? Also, I was frustrated with the fact that everyone talks about inspiration and creativity in this creative world. It's the last thing everyone needs. They've got enough creativity and ideas. In fact, that's the problem. You have too many ideas and people jump from idea to idea to idea and never get anything done.

Scott Belsky (35:27):

So I felt a real call to action to focus on productivity and the creative world and what we could learn from the most productive creatives teams individuals in the world. And so that's what Making Ideas Happen is all about. And really the book is brought down into insights around organization, insights around the leveraging community forces to hold yourself accountable and refine, et cetera. And then also leading creative teams, which is a whole different ball game as those who have.

Scott Belsky (35:53):

Then after that, I said, "I'm never writing another book again." That was a pain in the ass. And it was just a very like arduous and emotional process to get that thing done. And so years passed, but I was oftentimes in a board meeting or after a 2:00 AM phone call with an entrepreneur struggling with something or in my experience integrating the instant Adobe and building products at Adobe later on. I kept writing things down. I kept writing. I had an insights file. I called them Essential insights. And they were things that I wanted to remember. And at the time I was using Evernote, now Notion, but I was writing all these down. And I had at one point, like 860 something insights. And I figured I should probably organize these so I can have some way of referencing them.

Scott Belsky (36:33):

And so I organized them largely into three camps. One was around enduring the tough parts. How do you endure? And what are the tactics and stories around endurance in the lows? The second was around optimizing and it was a cheat because it was optimizing how you work, optimizing how your team works, and optimizing how your product works, which is of course, are entirely different of thought, but I figured I'd lump them all together.

Scott Belsky (36:59):

And then the third was around the final mile. How do people not get tripped up over their own legacy? How does someone not become a one-hit wonder? How do you not sabotage yourself in the final mile of launching a product or a project or starting your next chapter of your career? There was a lot around that as well. And so after all that, I challenged myself to synthesize this into a book and I felt the best way of summing it up is, it's really the volatility. It's how to manage the volatility in the middle.

Daniel Scrivner (37:25):

Do you have another book coming, or are you for sure no more books now?

Scott Belsky (37:29):

Of course, the answer right now is hell no. So none at the moment.

Daniel Scrivner (37:32):

I'm curious those books have meant a lot to me. I know that it's very rarely happened that I've mentioned them to someone that I haven't already heard about it, or they don't have it, or they haven't already read it. What, as an author, obviously there's this selfish or at least scratching your own itch piece to, like you said, just organizing things and then being able to share it with others. What's some of the most rewarding feedback that you've gotten from each of those books and people that have read them in stories come out of those?

Scott Belsky (37:56):

Well, this is the best part. You've been publishing as well and getting your thoughts out there. And so I'm sure you know what it feels like. You get an email from someone who's either listened or you read something you've done. And then they track it back to like a moment where they were struggling. There was no ask in these emails. It's just like, "I just wanted to thank you." And those mean the world to me. And whenever those come in, obviously it never gets old. It truly feels like you're doing something that matters in the world. I don't know what else to say. It's a great feeling.

Daniel Scrivner (38:22):

I guess coming into this, my thought was, you potentially have some sort of a writing practice, but maybe that's not the case. And it sounds like maybe that writing practices jotting down observations. And then at some point doing this mass coalition and distillation of that, is that an accurate way to represent it? Or can you talk about for you, how you go from having this constellation of insights into boiling that down into a body of work?

Scott Belsky (38:44):

I think you articulated it really well. And it's only at the final six months of a project where I start to apply incredible rigidity and discipline around writing time and whatever else. Before that, it's always a natural tending of ideas and we'll add more and more too. And then six months passes and I'll add a little bit more, and then two years passes. So with The Messy Middle, I was bringing up stuff that I've written over the seven years prior. It was very much a long drawn out process in that regard.

Daniel Scrivner (39:11):

I would love to spend a little bit of time on the piece of that that stood out to me, which is, you talked about you have this collection of insights on the final mile and part of that is not getting hung up on your legacy and part of that is not being a one-hit wonder. That's a fascinating series of questions and points there that I think a lot of people struggle with. And I think maybe one way to sum that up is, I've often wondered, and I'm sure you've wondered this as well too, and it will actually often happen for me with music where just yesterday, there was a song on at this restaurant I was at and it just reminded me that that's probably the only song from that artist I've ever heard. Yet it's literally one of the most popular songs through all of time and then nothing else ever gets released or makes its way out into the world after that. So I'm curious what are some of those insights that resonated with you or were all ha moments around the final mile?

Scott Belsky (39:58):

I talked to a lot of folks about this in different disciplines, including people in the arts and music, et cetera. And a couple of thoughts came out of those conversations. Number one is, oftentimes the cost of getting attention is that you're no longer paying attention. And so sometimes if you imagine anyone can identify with this when you post a new piece of content on Instagram or Twitter, and then suddenly you find yourself really tuned into detraction that's getting and what people are saying about it and commenting against what you said and whatever. And so your attention gets consumed suddenly as a result of your creation. And so you're unlikely to create in that zone because all you're doing is, you're tuning into what people are saying about your creation.

Scott Belsky (40:38):

Imagine that at a thousand million times where all people want to do is hear that song again and talk about that song. And you could go for 10 years and never get through your own fan mail. And so if you're a really seduced by your attention that you're getting, you will not create anymore. And so you wonder how these incredibly, brilliant creative people only did one thing and never again maybe it's because they felt in some ways victim to that. And maybe that's also why some of the great creatives are introverts and why they actually don't enjoy that fanfare and they tune it out.

Scott Belsky (41:11):

I think so a few tactics here. Number one is to always revert to your curiosity. The power and gravity of your curiosity must outweigh the gravity of the attention you're getting for your work. I think number two is, the idea of killing your creations once they're done. That era of my work is now dead to me. And now I'm focused on this. And that's an important thing to do. I remember there was a presentation at one of our 99U Conference, the Behance Conference we used to hold every year where a speaker talked about the idea of, for a creative person, are they their work or not? Are you your work? Am I my work?

Scott Belsky (41:47):

And some part of me says, yes because I'm passionate about my work. I care about my work. I'm not just shoveling snow or that might be someone's passion, but it's not mine, but I have found I'm fortunate, I get to do something I feel really passionate about. But that's also dangerous because once you are your work, your identity is tied up in what you're making. Then what does that mean once what you're making is done out there over uninteresting? And does that mean that your identity is over? There's something to be said about keeping them separate.

Daniel Scrivner (42:15):

It reminds me of a quote I heard recently, which was talking about what allows people to endure at a certain level over a period of time. And one of the observations, which for me, I was like, wow, it's an incredible insight I'd never thought about was, that at a certain point of time, once you've been successful enough, it's as much about forgetting things that you've "learned" so you can learn new things and so you can shed some of that old skin, so you can truly, I think be present, be curious again, and have new discoveries. And that for me was one of those like, oh that's just such a great insight in just a few words.

Scott Belsky (42:44):

Yeah, Daniel, just to elaborate on that, You just reminded me. There's a mentor of mine in Boston who was a really successful businessman, who I always looked up to growing up. I'm older than [inaudible 00:42:53]. I remember talking to him when I was in business school and him telling me that he doesn't save anything. He doesn't save a mentor. And it was such the opposite of me. I always saved... In the acceptance letter to college and everything was significant to me and I would meticulously save this stuff. And I couldn't believe that this person with such a great history, didn't save anything as almost like a pride point. And only later have I realized that those things that we've saved from our past in some ways are also anchors to our past in some weird way. Maybe they are us celebrating the wins from before as opposed to focusing forward.

Daniel Scrivner (43:32):

I would love to close it out to talk a little bit about the future. Because part of that obviously I think if you're an investor, if you're building on that frontier, there's a part of your brain that's just naturally wired to think and be curious about where things are heading. And you have what I imagined to be just a pretty incredible seat to that through from the investments that you're in, from the deals you're looking at, from your position at Adobe. So I'm curious, what sorts of books and ideas recently have been on your mind and have been shaping how you think about the future or how you think about what's happening now maybe a little bit more clearly?

Scott Belsky (44:02):

I'll share a few things that I've... So it's trends, I guess, that I've become really interested in. One, I wrote about right in the new year that I call Eduployment. And it's the idea of the vertical integration of education and employment. The idea that a company can train up tons of people to do appliance repair and then get certificates in every type of appliance. And then once they're certified, deploy them towards people in their region that need of an appliance repaired and have a vertically integrated marketplace in almost secondary education. And you're seeing this, that's a company called Nana, there's a company called Main Street that's doing this for house painting. And there are a number of other examples. And I just think that for the future of income inequality and marketplaces that allow individuals to be their own business, is this a part of that solution is something that's going to be very big in the coming years.

Scott Belsky (44:49):

I also obviously think a lot about the Creator Economy and how creators are owning their own audience and what that means in terms of traditional media. So that's obviously a trend that a lot of folks talk about. And I guess the last one maybe that's really top of mind right now is the Consensus Economy. The idea that, whether it's Bitcoin or Baseball Cards or anything else, the hyper network nature of all of us right now means that if some small long tail group of people, if they agree mutually on the value of something random and you can fractionalize that and trade it, et cetera, you can in theory have a long tail of currencies in micro-communities, and I think that's very profound for the future.

Daniel Scrivner (45:30):

Just on that last point, one of the conversations that just had, I think the last week or the week before was with someone who's building out a business and the collectible space, and they're literally finding insane stuff, whether it's a meteorite or a triceratops skull, this physical object creating shares of it and then allowing people to buy shares of that and have a portfolio. And they're also doing other and they're part of the trend in my mind that we're seeing whether it's NBA Top Shot, NFTs, this is going to be a shot in the dark because I'm not sure how much you've thought about this.

Daniel Scrivner (45:59):

But it's been on my mind a lot. To my mind, all of these things fit together, whether it's real-world collectibles, digital collectibles NFT. And part of that I think is, I'm less interested in the value question of why are people paying so much? And I'm more interested in, what is it culturally or generationally that we're going through that just means that the latest generations are much more anchored in digital and that's more real to them than physical? And that's of course, why all this makes sense. It's super shot in the dark. Do you have any thoughts, observations there?

Scott Belsky (46:29):

I truly agree with the way you see it. Obviously we're all digitally native. I think in some ways we were all waiting for something to collect digitally because collecting is a human nature. It's things that are profound to you. Why are things important to us? Because they're either scarce, because they have history, they've provenance until the advent of blockchain and some of the tools around transparency and provenance, it was really not possible to have that sensation in the digital world. But also a lot of us and especially the next generation they're living their lives in these digital worlds. Literally, they're living in virtual worlds where they want to look a certain way. Look at Fortnite and billions of revenue, all associated with people's skins and weapons and shoes and whatever they looked like in the game. So digital identity is a huge business and it's a big opportunity.

Daniel Scrivner (47:15):

And I'm guessing you would agree too, this isn't a fad. This isn't a temporal thing. It is a shift that has a tremendous amount of momentum, is digital things acquire more value.

Scott Belsky (47:23):

Absolutely. Now, of course, will there be ebbs and flows? Of course, right? There will be volatility. There's the messy middle for trends like these as well.

Daniel Scrivner (47:31):

I'm going to ask a different closing question that I typically ask. And you can answer this as an investor. Talk about one of the companies that you back that didn't work out, but you thought was an incredible team, was an incredible company to be a part of, or it could also be a personal thing. But the question I wanted to ask you is if you have a favorite failure, and that could be an investment, that could be something personal. Ideally, obviously something that you took something away from, but obviously where the value of that thing didn't really materialize, but you ended up being a very rewarding experience regardless.

Scott Belsky (47:59):

Well, there are many.

Daniel Scrivner (48:00):

I'm not surprised.

Scott Belsky (48:02):

There are products that I had to kill at the hands that probably wasted months, if not, years of my team's efforts that taught me how to be a better product leader. And there were also career mistakes. Certainly thinking idea, a traditional VC led me down the path that was wrong for me. And it was really very tough to extricate myself from that to some degree. I think I would probably go back to early lessons learned building a team at Behance. I think that one of the things I've always struggled with was always the desire to hedge the risks that I was taking.

Daniel Scrivner (48:30):

Like getting too diversified or bolting on other products and features of, yeah?

Scott Belsky (48:34):

In some ways, all the above. And I think that there is a debate about whether really good entrepreneurs are either major risk takers like the Elon Musk's of the world and the stories we hear about all in on everything versus folks that are very hedged always. I think I was probably too far though on that spectrum where when we were building a network for the creative professional world, we were also building a task management tool and we also had a paper product line and we also had a conference. And if you asked me why back then the reason was is that we weren't venture backed. We had to pay the bills.

Scott Belsky (49:00):

And also I felt responsible to make sure this business worked. And I wasn't willing to go all in on something. And actually it took my team really pushing me to say, "Hey, listen, we're splitting our efforts here. And if we really want to make a dent in eight world somewhere, you got to pick our thing." And as soon as I made those difficult decisions, we really unleash our potential. That was the beginning of the best days of Behance. It took some lifts to really get that right.

Daniel Scrivner (49:26):

Not to push back on that, but I will say the Action Method stuff I still use it, I still order it. I think it's awesome. So I'm glad you ended up doing that.

Scott Belsky (49:33):

Me too. I have right here.

Daniel Scrivner (49:34):

There we go. And I wanted to end this by just saying thank you. And when I reached out to you initially, I shared the story, but I want to share it with the audience as well. You talked about the impetus for founding Behance was creating a network and that companies couldn't find people's work and they would have to find you through some weird methods. And that ultimately meant that obviously it wasn't very democratic. It wasn't an equal playing field for all talent.

Daniel Scrivner (49:55):

And I started out my career, surprisingly enough, dropping out of high school to pursue design full-time. And I was one of those people who had a website with all of my workup on it. And when Behance launched, I neatly joined. I put my work up on it. And one of my projects ended up getting featured. And that literally was the impetus for me to get a call from Apple, to then move to San Francisco, to then go to Square. And literally, I'm sure I hopefully would have been just fine in an alternate universe, but Behance had a remarkable impact on my career. And I just want to say thank you so much.

Scott Belsky (50:24):

Thanks for sharing that. It's like this is the stuff that makes it so rewarding for our team. And obviously it's the work itself that ultimately yields the opportunity. But it's been really fun to build this platform and get inspired and humbled by the community every day. That's for sure. And thanks for having me on this. And I just love the podcast series you've created. So it's an honor.

Daniel Scrivner (50:41):

Thank you so much, Scott. I think I've made more notes of just writing down your quotes during this interview than any other interview. So I think a lot of people are going to really enjoy the show. So thank you so much for the time, Scott. I appreciate it.

Scott Belsky (50:50):


On Outliers, Daniel Scrivner explores the tactics, routines, and habits of world-class performers working at the edge—in business, investing, entertainment, and more. In each episode, he decodes what they've mastered and what they've learned along the way. Start learning from the world’s best today. 

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