My First Million: #32 - Product Genius: Scott Belsky

All right.

Quick break to tell you about another podcast that we're interested in right now, HubSpot

just launched a Shark Tank rewatch podcast called Another Bite.

Every week, the hosts relive the latest and greatest pitches from Shark Tank, from Squatty

Potty to the Mench on a Bench to Ring Doorbell, and they break down why these pitches were

winners or losers.

And each company's go-to-market strategy, branding, pricing, valuation, everything.

Basically all the things you want to know about how to survive the tank and scale your

company on your own.

If you want to give it a listen, you can find another bite on whatever podcast app you listen

to, like Apple or Spotify or whatever you're using right now.

All right.

Back to the show.

But here's the amazing thing is that when you ship a number of features and then you

start killing a few of them, what you find is that the core stuff gets used more.

A lot of social consumer products ultimately engage someone based on something they're

insecure about.

Hey guys, Sean here.

I got a different kind of episode for you that I think you'll like and just to set the

scene for you.

So I'm recording this right now.

It's Christmas Eve.

Got about an hour to go till Santa hits the chimneys.

And this episode is going to be with Scott Belsky, probably one of the coolest people

I met this year doing the podcast.

And as I'm recording this, you know, I'm just supposed to do the intro and tell you what

this is about, but I'm feeling a little reflective because it is the end of the year.

I started this podcast about six months ago on a whim.

I was bored.

We were selling our company and we were in the due diligence period and I was just getting

itchy waiting for lawyers to finish doing what lawyers do.

And I was like, I want to start something new.

And so I knew I couldn't start a company.

So I started a podcast and I didn't know if anyone would listen.

And amazingly, you know, I really thought nobody would listen to this thing.

And now here we are six months later, I'm looking at the dashboard right now and there's

526,000 listeners, over half a million listeners already just last few months.

And so I never thought that that would happen.

If you're listening to this right now, thank you.

This has been a kind of an amazing new addition to my life.

I started the podcast because I thought it would be a great excuse to hang out with interesting

people.

I don't drink coffee.

No caffeine from me.

I never had the taste for it.

So I didn't like inviting people out to coffee or trying to make up excuses to meet.

And I thought the best excuse would be, hey, come on my show, come on my podcast.

And for whatever reason, that kind of flattery works.

So I wanted to invite people like Scott onto the podcast and somebody like Scott's interesting

because I start the show with this, which is he's done basically every job I've ever

thought about doing.

So he bootstrapped his own startup.

He raised venture capital and ready to grow that way.

He sold his company and then he became a tech executive.

He's currently the chief product officer at Adobe, which is, you know, obviously Adobe

is a massive company.

So he's a, you know, he's been a founder, he's been a tech executive.

He's been an author.

He wrote a book called The Messy Middle, which is an awesome book about the process of creating

stuff.

So, you know, he created a guy who wrote a book.

He's been an angel investor in companies like Uber or Pinterest, aka, you know, two of the

best angel investments of the decade.

And then he was a VC with Benchmark, one of the top funds that exists.

So the guy basically has done everything.

And what I was blown away with and what you'll get out of this conversation is he's just

a good dude.

He's a very down to earth, smart person who, I think he says this somewhere in it, which

is his goal wasn't to become any of those things.

I didn't say I want to be a tech executive.

I want to be a founder.

I want to be an investor.

He was just curious and followed his curiosity and it kind of led him down those paths and

I found that kind of inspiring.

So, you know, as the new year hits, I'm thinking about all these different episodes we've done.

I don't know about 25 episodes meeting all these great people and then even getting a

chance to meet some of, you know, if we got half a million listeners, that's a cool number.

But I've gotten to meet, you know, hundreds of you in person at one of the live shows

or people who email me and we're going to try to squeeze in a Q&A episode this week.

So if you are listening to this and you're, you have a question that you wanted to ask,

you know, it could be about business, could be investing, it could be about a podcast,

whatever.

I'll answer.

Just shoot me an email.

My email is just puri, P-U-R-I, dot Sean, S-H-A-A-N, so puri dot Sean at gmail.com.

So just shoot me an email.

I'm going to do a Q&A episode.

I already have like 20 questions or so, but send them in and I'll try to get through as

many as I can.

I hope you enjoyed this episode.

We're not going to do a super fancy intro.

We're just going to go right in and it's a little bit different.

We recorded this thing at night and I just didn't have the energy to do the whole, okay,

let's start with your story from beginning to end.

I just hopped around on whatever was interesting to me and it made for a fun convo.

Me and Scott, I consider us friends now after this because the conversation was that fun

to be a part of.

So it kind of hops around.

It's a little bit of a different flavor.

I hope you guys like it.

And again, thanks so much for supporting the show.

The podcast is already bigger than I ever dreamed it would be and all that made me want

to do was make, grow it even 10 times bigger.

So that's what we'll be doing next year.

All right, guys, enjoy the show.

Scott, welcome.

Thank you.

Thanks for having me.

So Scott Belsky.

So I don't like doing intros because usually I butcher it when I do it, but what I thought

was interesting about having you was like, you've done the career path that's like everything

I've thought of doing, you've actually already done.

So it's like, you know, you've written a book, you bootstrapped a company, you've raised

venture capital, you sold the company, you've invested, you've been a tech executive at

Adobe.

So I'm like, all the potential career paths you've actually explored.

And so I was like, okay.

So you're a career identity crisis at all times.

Yeah.

So is that exactly what you're doing or you have no clue what you're doing?

Right.

Fine line between the two maybe.

And currently, which one of those paths are you in at the moment?

Yeah.

I mean, listen, sometimes I think, what is my happiest state professionally?

Actually just generally.

And I think it's the feeling of feeling fully utilized.

And I think that personally, you know, I'm a dad, I'm a husband, I'm a friend, you know,

you feel utilized in all those ways.

And then professionally, I feel fully utilized in a day like today actually, where I had meetings

with product teams, I had meetings kind of bleeding change in the big organization, those

types of meetings.

I also had pitches, a couple pitches from companies that I might invest in.

I also helped make a couple introductions to companies that I'm already investor in.

And I also even had a quick talk related to the book.

And so I feel like every muscle was stretched in some way shape or form.

That's a day.

Yeah, it's a day.

And so I think that I've always just tried to, you know, pull, pull threads on curiosities.

And I do, you know, I, you know, for better or for worse, I kind of am enjoying, you know,

both ends of the spectrum these days.

Yeah.

To give people a sense.

It's like 9pm on a, what is it, Tuesday, Monday night, I don't know, Tuesday night,

some day.

You squeeze it in.

And I was telling you, I was like, I give you credit because I know it's easy when

you're like two weeks out and you're like, sure, yeah, we'll make it work.

And then the day of you're like, and you're like ninth Uber of the day, and you're like,

what am I, who, who's this podcast?

What am I going to do?

Feeling good.

Feeling good.

But yeah, yeah, give you props.

In fact, on the last episode, I sort of put out one of my life theories, which is 80%

is just showing up.

And most of the things that you don't want to show up for it.

If you just build that discipline to just show up, good things happen.

I agree with that.

You just have to, you just have to do it.

Okay.

So you've done a bunch of things.

If I'm listening to this, I'm like, okay, why am I interested?

So you've created Behance, which if you're a creative person, you know exactly what Behance

is.

But if you're not somebody who's maybe a designer or somebody in the creative world, what, what

was Behance?

Yeah.

So Behance was inspired by a bit of a sense of frustration with the creative world and

just how disorganized it was.

A lot of my friends in the creative community, architects, designers, finding from college,

their careers were at the mercy of circumstance.

And I felt like, you know, they felt like they never got attribution for their work.

And I felt like they were not doing their, the greatest they could be doing in their

career as a result of that.

And so Behance was an effort to organize the creative world.

And people would always say, yeah, good luck with that.

But the, the idea back in the day was why are people having their portfolio sites sitting

on some websites out in the ether, only visited by people who know them.

Their work should also be broken out and searchable and sortable based on the client, the search

term or whatever, and then through someone's work, you discover who that person is.

Then you see their portfolio and then you see who they are.

And so it was inverting the model to some extent.

And it was a long slog.

I mean, Behance was five years of bootstrapping, two years as a venture-backed business, acquired

by Adobe, three years of integration.

It was an incredible journey.

Partridge and a pear tree.

Right, right.

We kind of saw it all.

But it's, it's great.

I mean, I love building products for creative people.

I find that ultimately across all industries, creative people are the ones that really move

things forward.

And they compel us to take action.

They prompt emotion through media and movies, whatever it is.

So it's just kind of an honor to build things for creative people.

It's always been something that gets me going.

Yeah.

Somebody asked me, they're like, why do you like to do that?

Why that?

In traditional terms, I don't seem that creative.

I'm not a designer.

I'm not an artist of some kind, not making music.

Anytime you're trying to make something new happen, you're being creative.

Fundamentally, you're problem solving something new.

And I'm like, it's really simple.

I like the new shit in the world.

I get excited about new shit.

And if you want new shit, you need people to be creative, and you need creative people

to have all the tools at their disposal to do what they do best.

Well, I think creativity is genuine interest combined with initiative.

You have deep interest into something.

It doesn't matter what it is to your point, but you also have the initiative to do something

with it.

And those are the folks that get fascinated by those edges that will someday become the

centers.

And that's what makes these work.

And so normally on the bottom, like, OK, be Hans, great.

That's the mission.

How did you think of the idea?

How did you get your first 100 customers?

Those are the normal ones.

And so if you're here to listen to that, sorry, I'm not going to do it this time.

There's people who have asked you those questions.

I've seen those interviews.

So actually, I don't know if it's because it's 9 p.m.

I'm in the mood to just talk about other things.

One of the things I want to talk about is you wrote this book, Messy Middle, which is

cool.

I'll tell you the premises I understand.

Yeah, sure.

The premises I understand it is 95% of the conversation is around the beginning and end

of companies.

I'm guilty of it myself, but, you know, press and media is much more, you know, that's their

bread and butter.

It's like somebody's starting something, somebody's ending something either from failure

or success.

So 95% of the talk or 99% of the talk is about 1% of the time that actually goes into

any venture.

And everybody just sort of fast forwards the middle, the actual sort of doing and navigating

of the unknown.

And so that's what the Messy Middle is about.

It's about that middle section.

I think Eric Rees has this good phrase where he's like, Act 1, we go into depth about the

hero and how they came up with their idea.

Act 3, you know, the resolution.

And Act 2 is the montage, which is all the hard work and it's just like all the training.

You just quickly fast forward through all of it so you can get to the good end.

It's not sexy, but it's kind of all the matters.

And so why write the book?

Well, I was fascinated by that big period of volatility that just seemed like an endless

succession of lows and highs.

I was interested in the idea that we're not our best selves at the lows or the highs.

We're not our best selves at the lows because we make decisions out of fear.

You know, at Behance, we saw new companies, new competitors emerge and we made a lot of

mistakes at times where we would suddenly try to emulate and then realize, wait, we just

lost touch with what we really are and what we're good at.

And then you're also not your best self at the highs because you falsely attribute the

things that you did to the things that work.

And so there's something to be learned at those moments, there's a practice to be developed

and how you endure the lows and how you optimize like hell, anything that works.

And that was what was interesting to me and I wanted to interview and chronicle a lot

of stories and insights from people that I've worked with, boards that I was on, entrepreneurs

that I partnered with and also things that I learned in my own experience.

And originally I kind of started this as a project for myself and then I realized I

had this Evernote notebook of like 680 or so insights.

And I said, okay, like I'm going to pare this down and ship it.

So that was the origin of the book because I was thinking, I was like, why not a blog

post?

Right?

Like I read a bunch of blog posts.

Part of the reason why I wanted to have you on is your blog is actually really good

and you can shop.

What's the domain?

It's just like Belski.com, right?

Thanks.

Yeah.

I guess, yeah, it's like on medium, but I don't know.

You can get there through many different ways.

Okay.

So I read a bunch of your things and you have these like, almost like watercolor art diagrams

of stuff.

Yeah.

So I've been reading these for a long time and I have a couple of friends, Sam from

the Hustle, who you invested in and Greg, Greg Eisenberg, he says amazing things about

your site.

That's why I wanted to have you on like your philosophies that I have read and then friends

who vouch for you.

And why not just like do a blog post?

Why did it have to be a book?

Yeah.

I mean, it's a good question because a book is kind of stagnant, you can't really update

it as easily.

Right.

I think though that a book is a forcing function to just still it all down and also try to

find the threads and then to package as a piece of art.

One thing I did with this book is every insight has like a statement that is also like presented

in sort of a design section to give it some gravity.

Gotcha.

Like what's an example of one of those?

Like an example is the science of businesses scaling, the art of business is the things

that don't scale.

And then it's like, okay.

What is that?

Right.

Unpack that.

Yeah, unpack that.

And so that will be like a two or three page section about how we sort of perseverate

over all the science nuances and actually our instinct is to not want to do anything

in our businesses that doesn't scale because we feel like that's a waste of time when in

fact a lot of the greatest examples of distinguishing a brand or a service are the things that don't

scale.

Like Airbnb sending out photographers for every apartment or I mean every company has

their example of the things that they did that don't scale that ended up being the art.

And how do you also preserve that as you grow and how do you decide what your art is?

And so that's like an example of one of maybe 200 or so insights in the book.

Gotcha.

You write this book and I like it because there's some books where you can kind of tell the

person who's writing this like they're either nowadays not trying to make money off this

but they're trying to parlay this into speaking gigs or things like that but like you already

had your sort of success and wins so this it feels like it comes from a different place.

It comes from a place of like I want to share wisdom or like first tap into the wisdom,

the scattered wisdom you had in your Evernote files.

Yeah.

Like put it together for yourself and then like generously give.

Is that like a...

Yeah, it was weird.

It was actually I remember the moment when I was kind of entering another one of those

things I had observed over you know a board meeting or something and then I realized gosh

like there are so many in here and I think it was on a plane and I remember being like

gosh this thing goes down like no one's ever going to see any of this stuff it's only going

to be for me.

Right.

And so that was one of those moments.

I also you know I think there's a part of me that aspires to do more coaching and helping

people build products and one of the things that I love doing and done it with Sam and

also with Bragg and others is help them develop their products and then build their product

teams and hire the right designers and build a design culture and I wanted to I did see

this a book as an opportunity to kind of help share some of the things I've learned some

of the things I'm thinking about and do more of that stuff so in some ways like a corner

stone of that of that intention I have for you know the next part of my life.

What's something that you commonly so when you advise people to say on building products

and making better products obviously as an entrepreneur you'd always be better you will

never turn down the opportunity to make your product better.

Sure.

It is your rock.

What's some like common things you find yourself constantly advising people to do or to you

know questions you keep asking or advice you keep giving is there anything that's sort

of a pattern you're noticing as you do this for different companies.

I mean there are a lot of them I would say like two that come to mind you know one is

obsessing over the first mile of the user's experience of the product which ironically

typically is the last mile that the team spends actually thinking about and yet it's the only

part of the product experience that every customer will in fact experience right after

that is just drop off.

And first mile just so people know that's just like literally the onboarding the splash

page onboarding step by step that the questions you're asked before you get into the product

how quickly you actually realize any form of value in the product right the defaults

of the product you know does it show you everything at once or only a few things the progressive

disclosure functionality like all of these factors are things you must consider as you're

nailing that first mile experience which is in fact probably what determines the fate

of most products frankly.

Yes.

You know you get 60 seconds or 90 seconds with the bulk of your cost of your potential

customer.

And I like to remind folks that every customer as great as they may be and as wonderful as

your product may be every customer is lazy vain and selfish in their first 15 to 30 seconds

of using your product.

How are you going to cater to them at that in that world before and I think the mistake

we make is we have to we expect our customers to have too much faith in us as builders they

don't care in fact they shouldn't because their life is too busy right and they shouldn't

spend any amount of time energy or effort you know until they actually know that they're

going to get value out of it right and so that's the conundrum so that's like one example

of something that you know I love working on with product teams another example is kind

of unpacking the psychology of their customer a lot of social consumer products you know

ultimately engage someone based on something they're insecure right something they want

to have validated something they want to learn or they're worried about or I mean there's

a lot of like under underlying nuances of a product that are really driven on psychology

um you know I was talking to the the team at visco the other day and you know they decided

not to aggregate the number of followers that you have visible to you nor do they let you

see how many likes something has that's very counterintuitive to what we know about ego

analytics and the things that drive social consumer product usage but they had an insight

right which was the type of customer and how they wanted to use the product that sort of

thing is very important thing to kind of distill and then make as a as a core principle and

so when you're investing in companies I'm guessing you're looking for in that first couple

you know first conversation with the entrepreneur you're trying to figure out what insights do

they have about the psychology of their customer and also when you demo the product how's this

first mile experience those are probably two of the you know first tests of your yeah they

are and of course you know for consumer products and for enterprise products there are different

types of tests or different types of lenses you look at them through but I think that those

actually apply to both you know in enterprise you realize that everyone wants to look better

in front of their boss everyone is you know sometimes even more lazy in terms of what

they're willing to do and so you have to build products and first mile experiences that

take those things into account so these are important things to to think about as you're

considering as an investor if you're a product-oriented investor like right and what what are some

of the investments you made that you're proud of yeah I mean I think that you know my first

ever investment was Pinterest so I met Ben Silverman back in 2010 and I had no business

being an angel investor I was just leading my own company but I had met you met him how

you just I met him through of all people I think it was our intern and he you know but

Ben was coming through New York to raise money because he had hard time filling his round

out here and and we both were building products that we were orienting towards designers to

some degree and a lot of the pins on Pinterest were driving to Behance pages and I was seeing

that although slow but rapidly growing you know source of traffic right back then it

was a forest Google but then stumble upon and tumblr made a couple others and and then

I just started working with him first as a product advisor and then when he was raising

the seed round he was like do you want to participate I was like okay so that was you

know that was the first foray it was amazing because it was just cool to see a product

at that stage and to share some of what I learned but also just engaged in a lot of

healthy debate right and so I think there you know there been a bunch of every product

experience that I've had with the team has been remarkably different I sat on the board

of sweet green for a few years you know a totally different world right but then again

sweet greens thinking about efficiency behind the counter and how to you know reduce operations

time or preparing salads they form factor of the actual bowls and how that increases

efficiency and is better for the environment the design of the space and then the mobile

experience they had this ambition of having over 50 percent of all orders you know started

on mobile you know and so I just I love getting a bit geeky with product problems and you

know and helping solve them right that's amazing okay so so you when you made that first angel

of estimate in Pinterest yeah you don't have a budget for this you're not like okay I'm

I've made it because you're still doing the hands at the time you had not exit correct

and so you said I'm in no position to do angel investing but you did it anyways what risk

did you take there so like when you put in whatever you put in like what percent of your

like net worth were you putting on the line at that time yeah it was it was probably a

good chunk of my salary and you know but the one other thing I did though to rationalize

it for myself I remember is Ben had worked at Google he had a network on the west coast

I was just like you know new entrepreneur in New York that didn't have any of that network

I actually felt like I would learn a lot from this and so in some ways I was like you know

I'm sort of paying for an education yeah if nothing more and it was again like I just knew

so little about everything I do now back in 2000 and what is it 2010 so it was nine years

ago it was if you have a real deep curiosity about something and then you find someone

you really respect and give a lot to learn from them find a way to get closer to them

find a way to work with them just always leads to something and you may not expect what it

is yeah this is timely so I just yesterday invested in the self-driving car company and

my last sort of like as I was going through the last checklist of like okay should I do

this you know this is meaningful money to me I'm not at the point where you know when

I invest dollars in I actually really want those dollars to come back I'm not this is

not like the philanthropy angel investing that some people do and so my last thing was like

look I'm gonna learn so much about robotics machine learning and self-driving cars and

I that's the future whether it's this company or the next one these guys are the future

yeah and this might just be my education and worst case scenario this is my education and

I started helping these guys you know a couple days try to get you know get their business

off the ground and already I feel like I'm get to live in the future yeah a couple hours

a week just by working with them it's like a you know it's a long-term view on the value

of learning and relationships but also for those that aren't ready to write a check to

people and there's so many ways of getting closer to people that you admire and want

to learn from and and keeping those relationships I mean I think platforms also like Twitter

are amazing in that regard there's some people that I somehow got connected to on Twitter

that I've never even met in my real life who just reached out to me and just started to

share like enough information and witty observations and feedback on something that I wrote that

I just start to follow them and then I follow them for a year and two years and then you

know these are folks that feel like you know them yeah and and anything that they were

probably doing next I would probably be first in line to help support or at least learn

more about and so just enlightening that anyone can kind of do their own insights and just

hard work and and knowledge sharing like you know sort of generosity in that sense build

relationships these days I learned this the hard way in the sense I host these like mastermind

groups do you do anything like this like a dinner series or anything like that with it

with the same with sort of the same set of people where you get together every two months

or so where it's like your peers do you do yeah only like informally there's probably

groups that I do that with but tell me about a so the regret was I moved to San Francisco

and I got invited to one of these and I was like this is great this is an awesome way

to learn and meet people because the good thing is you're at a table with founders and they're

not selling because it's like you're not their employee you're not their investor you're

not their customer so they're actually telling you what's up with their company and you're

sharing likewise and so the first couple groups I was in if I had just written checks to all

of them blindly I said you know like with no judgment I'm just writing the same $10,000

check in all of you guys you know calm was in that in that crew yeah exactly they would

have paid it off clear bit was in that crew product hunt Zola Electric which is the biggest

solar company in Africa like so that portfolio would have done amazing and so I look back

and I was like man I did the first part right which is what you're saying you know I just

spent time with interesting people and added value to them through sharing ideas and sites

whatever hope it being being helpful but then the lesson I learned was why wasn't I investing

and I to me I kind of asked myself this and I thought because I wasn't thinking of myself

like an investor yeah and so then it happened again and I saw this company called Lambda

School that was really big it was really early on and I started you know talking to Austin

and I was like this time I'm not gonna fuck this up and so I convinced my friend I was

like I found a company that's amazing if you invest this is I'm your scout here right

if I if you invest you know give me 15% of your your action and and let's let's do it

and so then that was like my first like deal deal where that's great you know I was able

to put it in and since then now you know once we sold I got a little more money so I could

do it myself but the lesson I learned and what I would tell anybody's listening to this

is don't count yourself out as as a player in the game either as a founder or investor

there is a way if you're willing to be creative and helpful enough I think yeah I think that's

one of the greatest cultural attributes of the system of kind of early-stage founders

is that we all know how much those circumstantial relationships matter and how much we learn

from one another and how we actually can't do it alone and you know that manifests itself

in ways like what you're describing yeah did you invest in Uber is that right yeah I did

so that was also kind of early on right and the funny story there so we were bootstrapping

our business the hands early days with paper products of all things we were making paper

products for creatives to be organized there was actually a payback and they're called

action books they're actually still out there okay yeah and so so and and one of our core

partners for Behance from a traffic perspective and partnership was with stumble pun Garrett

had recently purchased stumble pun back from eBay so he had sold it and he bought it back

and so he was in my apartment which was also my office back in the day in New York and

we were kind of jamming on some product stuff and he whipped out one of our action books

that I'd given him previously and was like hey you know check this out I'm like working

on this side project and then he shows me these sketches of this product where it's

about summoning a black car as opposed to having a dial for it and and I'm like dude

you should be focused on your business you just bought it back right now I'm a founder

CEO struggling your founder CEO now struggling like you're thinking of making it it's a distraction

yeah it's basically like that's a textbook distraction right and so fortunately he didn't

take my advice and he said you know do you want to do you want to be involved I think

it kind of was like I don't know but but then I also became a product advisor for him and

this is actually even before Travis was in the picture Ryan was involved and then of

course you know that team got up and running and so I had he asked me if I wanted to invest

in again like sure but I very small check which is all I could do at the time right and I

was a journey and so your stuff you do this sort of start as product advisor and because

of that you're at the table and so when the time came you were you were I try to I try

to fall in love with the product in the sense where it's still on my mind you know and I'm

like thinking through the problems and you know maybe you know what's wrong with the

interface or how could that worry me better so what's something at uber that the product

a product change early on like probably before any of us touched it that you remember was

or anything like that where I remember I remember a debate with Garrett around the brand and

this notion of should it be a it was ubercap at the time right it was ubercap at the time

should it be an expensive feeling brand where it looks like it's aspirational but something

you couldn't afford or should it be a an accessible brand where it feels like this is something

that everyone should be doing right and it was actually a really healthy argument because

you intuitively think it should be accessible to everyone I mean if you want to make a big

company but Garrett's view is that it should be something that feels like a superpower

like everyone's private driver to feel expensive even though it was intended to be accessible

and so that was part of the part of the thought behind the black kind of logo and and the

brand identity that like sort of suggested that that feeling luxury elite feel exactly

so I remember that debate and I think that was also the right choice that's amazing okay

and what are you excited about nowadays like going either a space a company a problem that

you think made solving what's got Scott interested well I think I think there's I think there's

there's a lot of different things that are interesting me at any point in time I mean

in my day job it's building products for creative people and kind of thinking about the future

of not only the creative tools we know but also things like augmented reality and and

how we're going to actually infiltrate and build content in that new medium that would

otherwise die if it wasn't enriched with like interactive animated hyper intelligent content

so it's thinking about that working with a lot of our partners like Apple and others

to help think through like how does that even happen it's been like a really fun thing for

me by day and you know by night I mean there's been a lot of really interesting enterprise

companies that are thinking about the future of work if you're in a big company you know

how hard it is for them to even think about a remote workforce and how to make a transition

even though a lot of us all know it's coming what are the steps to get there what kind of

technologies need to come about I also think that you know social has been out of favor

right which makes it interesting which means it's that yeah you know when everyone says

interesting is dead it means that something's being born right and now's the time so I'm

thinking a lot about consumer products that help people connect with one another in in

new and you know privacy driven premium ways that's what's a day in the life is there a

wake up time morning routine that you like that kind of works for you I mean every day

is it right but I am trying to think of anything that would be useful and helpful but I ultimately

normal is also useful you know because people are like oh there's no secret he just wakes

up and you know eats his breakfast ties his shoes a little bit groggy and gets out the

door like that's okay too yeah I know I mean I think that I think that I I so I do try

to switch it up you know I'm actually not one of those people that has like every day

has to be the same and whatever else but I do I mean there are a couple things I do like

I do try to audit my calendar in retrospect a lot of people only look forward not many

people with that so you do a time on it you like you look back at the last week or what

do you do I do I typically look back at the last week and I typically ask myself you know

how do I spend my time it's actually a really interesting thing because you're typically

at least ashamed of one day if not more than one day yeah how you did it and you look at

these blocks like what I do during that period but why did I meet with that person for that

long or whatever it is is this advancing you know what's most interesting and most important

to me right and that could be personal things and work things right but it's just this audit

and it's um you know it's prompted some difficult realizations like wow like that was more important

than you know seeing my family time yeah it's important I saw a version of this that I really

like so there's a guy you probably know his name is Matt something he's like the like coach

CEO coach to a bunch of CEOs in Silicon Valley he just wrote a book called the great CEO within

I think it's called it just came out and so Emmett who's the CEO at Twitch he I think he

works with him I might be getting all these details wrong name wrong book title wrong direction

ladies yeah something like this let's just wave our hands a little bit so this guy works

with bunch of CEOs and so he he wrote this book and I saw his like like you had your

680 evernote notes so he had a bunch of Google Docs that were just like quick you know like

principle after he worked with so many CEOs he was noticing some things he would just start

writing them down and he called this one the energy audit and so it's the same thing you're

talking about where you go back in your calendar but he said get two markers right red and green

or whatever red means this took this this activity takes energy away from you you feel

less energetic after you do it green means that activity gives you more energy right

like the gym is this weird thing where you would think you go to the gym you put all

this energy in and you exercise and that should deplete you but actually you walk out and

you fit more energy for the rest of the day right so like there's these activities so

we said just start highlighting and just look at the cup step back and just look at the

colors and then be like okay that's where you're at today let's try to move towards

more green and different things give you energy like the sort of doing things that are in

your zone of genius right things that you're good at things you know that are important

and you're you can just get in flow and do them and I really like that because it was

a it's one of those things you know when the first time you do it you're gonna like it's

gonna look bloody it's gonna be like oh this is not a not a good use of time I think that

would be interesting I wonder I feel for me as I have like a natural introvert tendency

and they say that introverts get their energy from being alone right I wonder if I'd be

skewed a little bit all the non-meeting times are green like that was the best time but

um but I like that I like that idea because I mean listen there are meetings where you're

like right you know and there are meetings where you leave with a lot that you're thinking

about maybe that's another measure also is after you spend time with something or someone

right are you leaving thinking about things I mean that is a one of the things I have

used over the years to determine founders I want to work with as an investor is if I

feel like every conversation with him or her was a step function more interesting than

the one before it or was it a repeat right a lot of conversations we have with people

are readies yes that's like I talked about the same thing last time right every now and

then you meet someone where you just pick up where you left off and it just gets like

actually even right you know better and better and richer and more dynamic and whatever else

I mean that was like the story with Periscope and I met Kevon and Joe and they were doing

this thing called bounty op at the time but every conversation with them about what they

were trying to build and whatever was was like infinitely more interesting right and

it was like okay we got to work together and what you're saying is it's not just that their

results were getting better every time because nobody does know right it was the ideas right

it was the ideas and the and the you know the maybe also chemistry like building upon

an idea like to make another idea right it's like oh my gosh sort of like seeing the world

through someone else's eyes oh it's like teleportation yeah oh teleportation right what would I want

to do you know maybe I'm bed at night going to bed I just want to drop into Tokyo and

like walk around it's like oh yeah like maybe you could do this oh you could go and see a

tennis match that's at Wimbledon when you're in New York and and then you suddenly like

oh wow like what are the media rights implications of that and maybe there's a business model

there and she's like thing the thing the thing the thing the thing and it's like okay this

feels good right yeah I like I have a similar thing where I call people Pokemon because

it's like your Pokemon just sort of evolve it's like the next time you see him oh my

god this this whole person has evolved into a better person yeah and those are the most

like fulfilling people to like I like that Pokemon yeah here we go new book one thing

I wanted to ask you because the way I look at it is this is a guy who's achieved a lot

of things that I'd like to achieve in my life right so just sold our company but you know

I'd love to write a book I'd love to you know achieve success in the next thing or invest

in great companies so you're still setting goals for yourself what's a goal you have

set for yourself now like what can you share that's that's something you're like all right

here's a goal I have for myself nowadays yeah well I think that there I think there's some

ideas and I'm like brewing that I want to give some time to right so I am trying to kind

of sporadically schedule time to just think through these things I actually love flights

for that reason because I can give myself a chunk of hours that you ordinarily never

get on that round right I think we'll just take a shower yeah right you know just uninterrupted

time I mean I do believe in this constantly connected world the disconnection is a competitive

advantage yes because you can actually think deeply about something as opposed to just

constantly react and heck away at the collective inboxes around you right I yeah I think that

I also certainly have some goals for like the changes I'm trying to bring upon the teams

you know that I'm that I'm leading now you know as this chief product officer role at

Adobe I mean this is just a company that bought my company a lot of my DNA is in this business

I care about where these products land and what you know and so I've set some like KPI

driven even yep you know goals around and it's just it forces you to start making big

swings and and think about like how you're going to lead those changes and get people

to to go along with it and you know and then it's about narrative and merchandising and

all these other things that it's it's fun you kind of have to build a internal marketing

campaign at times just to get people to change their minds totally so so those are just a

few examples okay and if you were 21 again today so I'll let you keep all the knowledge

you have but you give me back sort of all your all your assets your reputation nobody

knows you you're 21 years old again what do you think you do how do you think you would

go about spending you know the next few years of your life well I would I would definitely

start something again if I had really a deep interest I think I would probably aspire for

more empathy for the customer suffering the problem as opposed to my passion for the solution

I think a lot of the mistakes that I made early on was that were that I was always like

super passionate about what I know needed to happen and then we would realize eight

months later we were like 30 degrees off cherry pick evidence that might fit yeah the need

for that solution exactly because you're you know you get excited by a prototype and a vision

and you want alignment so you force alignment and then you realize wait had I just spent

more hours next to a customer seeing what their actual life was like what they actually

thought of my product I would have known better right so I think those were some of those there

were I think a few lost years as I like to call them in Behance in that five-year bootstrapping

period where we had to rebuild a lot of stuff and I can't say I would do that all over again

you know if I had the choice although I would say that it definitely built us as a team like

a culture and we went through a lot to get adversity we'll do that to you it did like

what doesn't kill you makes you stronger like definitely true right and it seems struggling

I think I would also try to do fewer things I you know and I go back and forth on this

I've heard two contradictory theses about yeah about like what makes a great entrepreneur

either you are really really great and willing to take risk or you're really good at hedging

risk it's like wait those are like which one is it right I and I was always a hedger you know I

always was thinking about the contingency plan and that caused me to do a number of weird things

number one it caused me to go to business school simultaneously as I was starting a business and

not drop out I see little did I know that dropping out would be way better PR value than finishing

no one gives a shit about an MBA right right the second and so the other the other way you had

taken let's say taken the risks yeah that would be what okay so so dropping out to one what were

some other ways that you were doing contingency plans does that mean oh yeah sorry I was gonna say

like also like another example was the number of products we were building you know because I was

like if this one doesn't work then this one will work right you know and and even like features

yeah it's like the insecurity of shipping many features in a product is basically I don't know

what's gonna work right but here's the amazing thing is that when you ship a number of features

and then you start killing a few of them what you find is that the core stuff it's used more

and gets more attention from the team too and it was one of those really strange realizations

I would say four years three or four years into the answers again probably two years too late or

too much later than it should have been where we killed a few major features we had this tip exchange

thing where creatives could leave like tips for another and build upon each other and vote them

up and down it was like a mini dig at the time but within the hands there was a group's functionality

where people could share and then we killed both like one after the other and then suddenly people

created more projects and they use and they use the core fee functionality more and I just again

wish I could have gone back and just really drove it down to like what do we actually have to ship

and how do we make sure it's amazing and what space would be interesting to you for 21 would you be

like building tools for creatives or would you go into bio hacking or you know like whatever like

is that that point you have a long time where you can ramp up or go into any space you're not

sort of committed sure and I guess the question is if I was 21 today or I was 21 back then because

back then I think 21 today yeah 21 today I would definitely be doing something different first of

all I mean we're still living in an app driven world which is crazy I mean apps were born in the

world where there was no GPS there were no notifications there was no AI and and so you had to download

apps and then use them for things now within a modern OS that should know where you are and what

you're most likely to want to do based on where you are and when you're there and with whom you are

with the whole operating system the whole notion should be completely different there shouldn't

even be apps frankly there should be superpowers that are suddenly there and then they're suddenly

gone and and if you think about and I think that we're going towards that and I think that we

will see operating systems evolve I think that the notification systems we know them today will be

totally antiquated to do this more you know actionable interface that just is always like the

sixth sense the appendage that we never know we need it and I think about like what are the

applications that are going to thrive in such a world I also think about marketplaces that are

more sustainable you know the the modern notion that every freelancer marketplace essentially

taxes the transaction is silly right and that's actually the on-demand model for on-demand

marketplaces and it's all the same formula right there's a totally different model that should

exist maybe it's blockchain driven maybe there's you know some other mechanic at play for value

distribution so there's a lot of these things that I think a bit about some of them overlap into my

day job some of them I'm looking for companies and entrepreneurs that are tackling and want to

help them what I like about your approach is that you didn't start with some idea how I want to

build this or a generic space but it was more like why are things the way they are wait shouldn't

they be different like you basically were like why are apps and notifications the way we use this

phone now that we have XYZ or why do all marketplaces do this you know rent seeker model where they

just you know sit in the middle and grab from every transaction so it's funny like one of the

things I learned most working with the benchmark team for a little while was I really went in

there thinking the greatest investors are really good in the future and what I left there believing

is that the greatest investors have a really deep and concrete understanding of us and and how the

present is like about to change and you can kind of but not you know distant distant long shots are

fun bets but they're bets right but if you really have a tune into the current dynamics and just

how they're slightly shifting and start getting ahead at really interesting I see and so you

where do you like to learn from so like what do you listen what podcast do you listen what book do

you read who do you think is really smart where if there's talking you're listening what what do

you like to feed your brain yeah no it's something that so I'll tell you like my first answer is I

have I am a huge fan of Twitter but I think that is an incredible it sounds such a cliche answer

but I have carefully curated a group of people they're they are astrophysicists they are biologists

they're economists they're political scientists there are other entrepreneurs and designers

and illustrators these are the people who curate for me every day what's interesting to them I just

think that's freaking amazing right you get to surf on top of that it is it is and so some people

say oh my gosh it's been so much time on social media actually it's just literally going through

and reading yes if you think about it but but curated by the people and I just learned about

the books that I want to read right and that's so I mean I love reading books related to psychology

and I love reading I'm starting to listen to a lot of history podcasts so like some of those like

Kings of Kings type podcasts I think are super interesting because you're just learning about

this notion of history rhyming like it's so true I mean you're learning about what happened in like

Rome you know and you're like oh my gosh it's happening all over again now in America right

there's just a lot of that so I but I try not to you know I actually don't have like one feel

that I'm just like I love reading just this genre or whatever you know I don't read too many business

books I well I find that most of them are a big book about a little idea you know so I feel about

most books it is but you know I think that and I have an argument with my publisher about the messy

middle because I came in with this like this this big book of like you know between 100 200

insights that were completely disconnected from one another although there was some sort of read

but you know and they were like this is not what you're supposed to do just write a chapter book

and I was like let's reach out right yeah at least my audience they're too busy you know they're

starting companies they're changing companies they just want actual insights they'll make them think

about something differently right and like where to go to learn more right turn the page and then

like you know turn on your brain yeah that's at least what I want yeah great all right I know you

got to help on a flight so I clock look at this perfectly on time that's my podcaster instincts

great 10 p.m flat yeah this was fun I hope you guys like this conversation if you want to follow

Scott where should they follow you reach out to you hey just Scott Belsky at Scott Belsky

wherever whenever great awesome

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Machine-generated transcript that may contain inaccuracies.