628: How to Stay Challenged and Grow Your Career with Daniel Scrivner

By December 21, 2020Podcasts



Daniel Scriver shares insights on how to develop your career from his experience as a college dropout turned designer turned CEO.

You’ll Learn:

  1. How to develop new skills through self-teaching 
  2. Why Daniel left a dream job at Apple
  3. Why you should always seek discomfort 

About Daniel

Daniel Scrivner is the CEO of Flow. Previously he was the Head of Design at Digit and Square. He’s worked for some of the most respected brands in the world including Apple, Nike, Disney, and Target. 

Daniel advises world-class teams at companies like LendingHome, Empower, TrustToken, Designer Fund, and Notation Capital. He’s an early-stage investor in businesses like Superhuman, MixMax, Notion, Good Eggs, Burrow, Madison Reed, Stance, Almanac Brewing, and many more. And he’s been invited to speak at some of the world’s most prestigious organizations including Andreessen Horowitz (A16Z), General Assembly, Techstars, Designer Fund, and 500 Startups. 

Resources mentioned in the show:

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Daniel Scrivner Interview Transcript

Pete Mockaitis
Daniel, thanks for joining us here on the How to be Awesome at Your Job podcast.

Daniel Scrivner
Thank you so much for having me on, Pete.

Pete Mockaitis
Well, I’m excited to dig into this conversation not the least reason of which because you have the fanciest microphone a guest has ever brought onto the show. Can you tell us the backstory of why you have such a piece of equipment?

Daniel Scrivner
Yeah, sure. So, I actually started recording my own podcast a few months ago and was debating in my mind kind of, as everybody does that cares about audio, what sort of a setup to get. The microphone that I use is the Neumann U 87. And I don’t have a great reason for that. I mean, just the only thing that I would say is, in my life, if there’s something that I enjoy, I never feel bad about buying, going for quality if I know that I’m going to use it for a really long period of time, and this seems fit to that vein.

Pete Mockaitis
I hear you. Okay. Well, I love it. So, I also love your story, so it’s pretty wild in terms of so you went from a dropout experience all the way to becoming a CEO with some exciting adventures in the middle. Can you please tell us the story of your climb and maybe the most compelling lessons along the way? And we’ll have a little back and forth as we do so.

Daniel Scrivner
Oh, sure. And I’ll try to keep it brief and feel free to jump in any time. But, yeah, as you alluded to, I definitely have an unconventional background. But what’s funny is it makes a ton of sense to me, obviously looking in hindsight, but when you said the words “the climb” I don’t know why but I don’t feel like it was really that. I guess that for just a little bit of context, a few things that maybe will help kind of makes sense of my journey is, one, I’ve always been a huge believer that if there’s anything in life you’re excited about, if you care enough about it, if you’re curious enough, you can teach yourself how to get good at almost anything.

So, what that’s I’ve done, and I sorted out my career, I focused on design. Specifically kind of web, digital design. This was back in the early 2000s, I’m a child of the 80s and 90s so I grew up with the internet being a really exciting, cool, new part of my life. And the quick backstory is, growing up, I was never attracted to anything design related. In fact, I hated art classes growing up. I never considered myself a very artistic person. So, how I kind of stumbled into design, as I think about it, is I was getting ready to graduate early from high school, this is going way, way back, I ended up taking a course one summer to get some extra credits, I just thought it would be a nice easy fun course about how to create HTML websites. And back in that point in time, creating websites now is a lot more complicated, back then all you needed to know was HTML.

So, I learned that class and I just got hooked on that I suddenly had the skill where I could take an idea in my mind, be able to use HTML to build it, and then I could tell my friends, “Hey, go and visit this URL,” or, “Hi, go and check this out,” and they could pull it up. And that just seemed like this magical thing to me.

And so, the way I stumbled into design was I started making these websites and thought I was going to be excited to share them with friends, but then nothing ended up looking like something I was proud of. So, it’s that moment where I was like, “I can make something but I want it to be cooler. Like, I care about this thing, I want it to be nice.” And so, that led me to this question of, “Well, what is that?” And, for me, it still is how I think about design as I think a lot shaped by that early experience. But my career now, I’ve been doing design at some level for 15 plus years, I’ve worked at companies like Apple and Square and with a bunch of other interesting cool brands.

But, for me, design is just the intersection of solving really hard technical or business problems and trying to pull it off in a way that you can create something that’s singular. So, ideally, it’s remarkable and that it’s unique and interesting and you’re contributing a new note to the melody but, at the same time, is beautiful and you’re kind of pulling off an artful twist.

Pete Mockaitis
Okay. Well, yeah, why don’t we get the broader view first and then we’ll dig into the details with one exception. Okay, so design, I’m not great at design and it always sort of kind of struck me as something – it’s funny, this show is about how to be awesome at your job and skills learning and growth and development, so I almost feel contradictory saying this. But it almost strikes me as something you’re born with, like you’ve got the designer’s eye, like you’ve got the touch, and I was like, “I don’t think I have it.” So, I always outsource my design and I think I know enough to say, “I don’t like that,” and “I love that.”

Daniel Scrivner
You’re a great client.

Pete Mockaitis
Well, it’s so funny, I love designers, I love working with them because I’ll tell them exactly, sometimes I feel crazy about my feedback, like, “As I behold that image, that part of it makes me feel like a little kid and you’re patronizing me,” and they say, “Oh, thank you. That’s great feedback.” I was like, “Really? Because I feel silly saying that out loud and like you’re going to bite my head off,” but the designer is like, “Oh, perfect. I know just where to go based on what you’ve said.” It’s like, “Great.”

Daniel Scrivner
No, I think that’s really all designers, I think, are looking for a lot of the times is just specific actionable feedback. As an example, one, probably the vaguest piece of feedback that I’ve ever received, and it was while I was at Square, and it was from the CEO Jack Dorsey who was looking at a design I did, and said something along the lines of, like, “It’s not whimsical enough.” And that definitely sent me down a like, “Oh, my God, what does that even mean? Like, what is that? Is it the color? Is it the structure? Is it the…?” I don’t even know. I didn’t even know where to go with that.

Pete Mockaitis
It’s not whimsical. Well, because, oh, man, I think for like corporate design, it’s really easy to be too whimsical real fast, and it’s like, “I don’t trust this, what I’m looking, at all. This spinning helicopter hat.”

Daniel Scrivner
He wanted that dial cranked up and I was scratching my head for a long time.

Pete Mockaitis
So, let’s start there. So, learning design, that seems like a skill that’s hard for people to pick up if they don’t have some kind of aptitude for it but it sounds like you disagree. Lay it on me.

Daniel Scrivner
Yeah, I definitely disagree. So, I think, well, just to take a step back. I have definitely worked with a lot of engineers that have led me to believe that there are certainly some people that probably don’t get design, like don’t understand colors, just kind of don’t understand just aesthetics in general. So, I think you have to have some inclination or curiosity or a desire to do a lot of research to just develop a point of view about like what looks good and what doesn’t and what is that. And that’s something that’s very difficult to build up.

If someone were to ask me, “How do I figure that out?” I would say, “I don’t know. You need to watch a lot of movies, read a lot of books, look at magazines about architecture and car magazines,” because I think that’s one thing that’s always fascinated me about it is great design can work in any industry whether it’s an interior designer using color and shapes and symmetry and patterns and textures to create a beautiful inside of a house, whether it’s an architect using some of those same tools to create a beautiful structure.

What’s interesting about design is kind of, if you boil it down, it is extremely primitive in that it’s largely shapes, colors, tones, moods, so, I definitely believe that anybody can learn it. And I think that, for a little bit of the backstory there, so I’ve mentioned I’ve been doing design at some level for 15 plus years, and every single year I continue to get probably a handful of emails from somebody that saw my work or listened to an interview that I did, who writes in and says something along the lines of like, “I’m inspired by your story. This is something that I want to do. How do I figure this out? How do I start working as a designer?”

And the reply I always write back is probably not the reply they were expecting. In fact, rarely do I ever receive a reply back. But it’s just along the lines of, “Like, the way I was able to do that,” so if someone kind of understands my story and knows that I dropped out of college so I don’t have a college degree, I did that because I found in this thing that I loved and I didn’t want to put that off anymore.

But the way that I learned it was extremely basic and probably it’s just like hustle applied to trying to learn. But, for me, it was very much like, “I want to do this thing,” so my approach was just, “Okay. Well, I’m going to do free work to start,” so I literally got paid nothing when I first started, and I was going to, honestly, anybody I knew or anybody that knew somebody that I knew that wanted something designed, and typically that would be a business card or a logo or a website, and I would just do it for free because I knew that I wanted to be doing it, I needed to have a portfolio so I can get better work, land better clients, eventually start paying. And so, I really just worked my way up that way from literally the lowest level on the totem pole of doing free design work for people that I just knew, all the way to working for some of the largest companies and most respected brands in the world. But it very much was a, “I’m just going to take it one step at a time.”

And, for me, one thing that ties back to, which we can certainly explore, is something that’s played a big role in my life is what I refer to, what I call the growth curve. And, for me, it’s just the sense that I think the way I’ve been able to get to where I am today is by constantly trying to challenge myself. And I’ve done that multiple times in my career where I’ve left really comfortable jobs, not because I wasn’t excited about that work anymore, I was still very excited about the work I was doing at those companies, but because I felt like I needed a new challenge.

And I don’t really know, I sort of know where that comes from, but there’s something in me that once I’ve kind of figured something out, I get a little bit uncomfortable and restless. And so, I’m always trying to challenge myself and kind of climb this growth curve.

Pete Mockaitis
All right. Well, so there’s a lot in there right there in terms of going out and doing it and getting a lot of reps. It sounds like whether that’s doing your own work or observing other work. And I found, I think, it is interesting with design in that I think it’s taken me a while to get here and not that I’m a pro by any means but it really is, for me, it’s kind of uncomfortable for a while, it’s like, “I just need to kind of…” I feel it first and then I had to articulate it in terms of, “Being in this room feels awesome. I love it here.” It’s like, “Why?”

Pete Mockaitis
But then you start to get a few things. In, like, realtors, like they’re taking photographs of places, it’s like, “The top thing is it’s free of cluttered garbage.”

Daniel Scrivner
“It’s bright. It’s airy. It’s typically lots of light, lots of very clean white and stainless steel.”

Pete Mockaitis
“And there’s just not a lot of clutter.” And I think that’s huge right there in terms of…and that can apply to a space or to a layout or a website or whatever. Like, I think Oli Gardner, I heard on an Unbounce event, had a slide wherein someone was like begging like Oliver Twist, “Please, sir, one more link shoved into this website.” It is like, “No, you got to keep it focused.”

Okay, so by doing a large volume of work, and by pushing and challenging yourself, and by observing and reflecting, you got really good at this skill. So, the here we are in your story.

Daniel Scrivner
Over a long period of time.

Pete Mockaitis
So, now you’re great at design and you have made some stuff that looks good, and where does this story go next?

Daniel Scrivner
Yeah, so maybe that was the kind of first formative part of my career, and I think for me there was a moment in time that I still remember very vividly but at the time didn’t feel…honestly felt scary and I don’t know if I was optimistic but I was excited about it but, basically, to share a little bit of the story. So, I’m in high school, I take this class, I start doing work for free, literally, when I’m in high school, end up graduating six months early. A big reason why I did that was I just wanted to do more time doing design work and I felt like, “Why spend all my day in school if I can kind do more of this work that I really enjoy?”

So, I graduated six months early. Fast forward a couple of years, and I’m suddenly at the point in my early 20s at this point in time, probably 21, something like that, say, and I suddenly have this kind of fork-in-the-road experience where I’m in college at the time, I’m about to finish my undergraduate degree, getting ready to kind of pick and transfer to the university that I want to go to which, in my mind, is kind of my parents’ voices. They were always very much, “You have to kind of go through this order,” and one of those things that was non-negotiable was going to college, so I was like, “Okay.” And I know that’s what I should do or that’s what felt like what I should do.

But the other thing I had in the other hand was, at this point, I had done enough design work that I actually was getting paid to do it, and was really enjoying it, and had enough work that I actually had to turn down projects. And so, the fork-in-the-road moment was, “Do I continue with college, kind of go to a university, really focus on that experience for the next two years or do I decide to take a bet on myself?” And at that point in time, the way I was framing it, which was probably a little bit nice, is kind of pause school for six months. I ended up quitting the job that I had at the time so I kind of severed all of those things so I could go all in. And my only goal was, “Let me see if I can survive basically doing everything by myself.”

So, I would pitch clients, I would quote clients, I would give them estimates, I would do the design work obviously, hand off the designs, do all the kind of the clerical stuff and accounting stuff. I just did everything. In those six months, I ended up doing that. Initially, my goal was just to make it six months. I ended up making it six months and it wasn’t pretty. A lot of that was extremely challenging, it was extremely difficult, it wasn’t all stuff I was super excited about. Balancing books or collecting invoices or following up on payments is not the most exciting thing in the world compared to design, but I ended up doing that.

And what that ultimately led to was, fast forward another year past that, I ended up getting offered a job to go and work for an advertising agency in L.A. called DDB. That led, about a year and a half after that, to getting offered a job at Apple to join their marketing communications team which was when I moved to San Francisco, and I ended up being at Apple for three and a half years. And I credit that a lot with being my…if there was any real-world bootcamp-like education experience in my career, it was absolutely being a designer at Apple.

Pete Mockaitis
Okay. Well, so let’s zero in on these particular bridges, leaps, transitions to DDB and to Apple. How did they find you and interview you, etc.? Was it just like, “Your stuff looks good, come on down”?

Daniel Scrivner
It’s effectively that’s the gist but the DDB, to be super honest, I have no clue. I cannot remember if they found me, if I found them, I’d never really heard of the firm before so it’s made me think.

Pete Mockaitis
Oh, they’re huge.

Daniel Scrivner
They’re a big advertising agency but they’re not Ogilvy. They don’t have that kind of brand name recognition necessarily so that one I’m not sure.

The Apple one is, I think, a little bit more interesting. So, the Apple one was, at this point, I was, I don’t know, mid-20s, probably 25, something like that, 26, and I, for sure, obviously, Apple was an incredibly exciting company, and I think for a lot of designers, it’s the place you hope you can get to at some point in your career. And so, the way that kind of transpired for me is I have this job at DDB at the time in L.A. so I’m commuting to L.A. and I’m doing all that and I’m enjoying my work. It’s not the most exciting. I’m not doing the most challenging interesting modern stuff but I’m doing it. I’m an actual designer getting paid to do design work which is crazy.

And I end up getting an email from a recruiter at Apple. And for those that don’t know, Apple is definitely one of the companies that they have a large recruiting team, and their recruiting team, they really are looking for the best of the best or people that they feel like can succeed as designers in some department at Apple. And for people that don’t know as well, Apple is massive. Even in the marketing communications team, I joined as a marketing designer, I worked on a lot of Apple.com projects, I ended up getting to do a lot more interesting stuff kind of in my time there.

But Apple also has motion graphics designers which just do things like animations and transitions and videos. They have graphic designers which do the packaging and the identities for some of their products. If you look at like AirPods Pro, like that name on the box, that’s something that a graphic designer put together letter by letter, playing with the kerning, playing with the weight, trying to get that just right, so it’s a huge department.

So, to kind of get back to the story, my first thought, honestly, was this is spam. Like, “Let me see where this email is from. Let’s me see if it’s actually from Apple.com.” So, I end up looking at it a little bit, kind of looked up the name of the person who sent it, and it all checks out. And the way that worked initially was I was offered an opportunity to come to Apple and cover for a woman who was going on maternity leave for six months, so it wasn’t like, “Here you go, here’s a full-time offer.” It was, “We really like your work. We would like to have you on the team to start,” and this is also very common at Apple about, I would say, probably 50% of the creative team is all contractors so it’s not full-time employees, so that’s not uncommon.

But I came in on contract and kind of my approach was, “I’m going to soak up everything I can, learn everything I can in these six months, and I’m also going to try to prove that I have a place on this team, that I can contribute and I can be a good designer and a good kind of member on the team,” that’s a little bit of that story.

Pete Mockaitis
Okay. And so, recruiter. I’m curious, in both of these instances, did they just not care, like it doesn’t matter in the design world, or for you in particular, “Oh, you don’t have a degree? No problem”?

Daniel Scrivner
So, it’s really interesting. I would say, for both designers and engineers, number one, I think there are a lot of technology companies, it’s definitely not a deal-breaker. Like, I think Google, they’ve relaxed this policy, but Google is definitely out of the norm in their requirement, which I’m not sure if they have anymore, but they have had for a very long time, is a requirement that you can’t get hired unless you have some sort of a college degree. But, typically, at technology companies and at startups, it doesn’t matter.

And the way that I’ve always thought about it is the majority of designers I’ve worked with do not have a design degree, and I think that’s part of the problem is if you were to try to go get a design degree, you can get one but it’s what is typically called a Masters in Fine Arts. You’re going to be doing it for six years, you’re going to learn all these kinds of fundamental skills, which I would argue you could learn just as well on your own by teaching yourself because it’s just literally going in kind of design history, looking up work of famous designers, doing these mock projects.

And part of that was, the way that I thought about it was, because if we go back to the part of my story where I was deciding whether to go to college or whether to take this kind of six-month bet on myself, definitely in the back of my mind was, like, “I can go and study design,” but the sense that I had was I was going to be learning fake design. So, part of what you do if you go to a Masters of Fine Arts program is kind of like going to business school, and you do a bunch of case studies, which are perfectly fine. They definitely help exercise some of your mental muscles of like, “Here’s a problem. How do you figure it out?” But does it map to the real-world job of being a designer? Absolutely not.

The most difficult things involved in kind of being a designer at any level is stuff like, “How do you gracefully take feedback that you agree with or don’t agree with? How do you ask really great questions of another person’s work where you don’t want to offend them, you want to know and respect that they put a lot of work and energy and love into what they’re creating?” But you want to try to ask great questions to kind of spur and make sure that it’s as good as it can be. And so, there are all these skills in design that are largely very powerful but very soft skills. And the only way you can really learn them is by doing it.

And so, that was kind of my perspective at the time. And what’s been interesting is I’ve had the opportunity to work with quite a few people that have a Masters in Fine Arts degree, and I don’t say this out of disrespect for any of those people, it takes, obviously, a huge amount of hard work to go and get a Masters in Fine Arts degree. But did I think they were necessarily better day in, day out designers? No. And I think, typically, they would have kind of a chip on their shoulder a little bit of, “Well, this project is too good for me.” And I think part of what helped me was there was no project that was too good or not good enough for me. Like, I was excited to work on it and take it on if it was a design challenge. And I also just loved it and I think that there’s this kind of sense of enthusiasm and love that, I don’t know, maybe I didn’t get it beat out of me in college but I was lucky that way.

Pete Mockaitis
And that’s a great perspective when you’re at Apple, it’s like, “I’m going to learn as much as possible in this place,” and in so doing your skills are sharpened. And so, what happens next?

Daniel Scrivner
So, I ended up at the end of those six months, I got offered a full-time position and I joined the Apple marketing they called it. I don’t know what’s called anymore but they called it MarCom internally which was short for marketing communications. But, basically, at the end of the day it’s like everything that’s not an ad on TV, that team did it.

So, I ended up getting offered a full-time position. Fast forward a little bit, about three years later, I found myself in a position I found myself in a few times now where when I first got offered the opportunity to join Apple, I thought, “Oh, my God, this is it. This is the place I’ve wanted to be. I can’t wait to be on this team.” And three and a half years later, again, really, like for me, I think a word that sums up a lot of how I approach the things that I love, which is both good and bad, but I think largely good is obsessive. And so, for me, with design, I just obsess over it. I would think about it all the time, I would constantly be working on little projects to try to improve my skills.

So, one of the things that I would always do when I was at Apple, and I think this is great advice for anybody that has a job, where it’s like you’re going to get better the more you do it. And if you challenge yourself with things that are slightly out of your comfort zone, you’re going to show up to work just a better all-around employee. But I would do things like, when I first joined…I knew how to put together a layout. In a layout, you can sometimes describe that as like if you go to, I don’t know, Apple.com, a layout is “What generally does this page look like? How do you chunk it out? What’s the typography there? Where are kind of the images?” It’s very similar to doing product design if you’re doing a layout for a screen.

So, I could do that but I suck at doing icons, and icons are this thing that they are like if you go and you open up your iPhone, if you have one, or Android phone, if you don’t, you look at kind of the app icons or the little graphics or symbols that you click on to get around an app, that’s icon design, and it’s both a very ancient form of communication. It’s based on hieroglyphs and cave paintings, and there’s a lot of those things that map almost literally one-to-one for kind of icons that we have today. So, it’s a very old form of kind of communications but I was really bad at it.

And so, one of the things I would do is just challenge myself, like, “I’m going to make an icon set of 30 icons I’m excited about.” And the way these projects always go is they’re absolutely brutal in that for 80% of the time I’m just like, “Oh, God, I’m not getting any better. What’s going on here?” And I just keep chugging through and trying to put one foot in front of the other again and again and again. And, inevitably, what happens is if I can just persist long enough, I’ll finally get to a place where it all snaps into place. So, I would do stuff like that.

But about three and a half years in, I just had this moment where I felt like I knew how to be successful at Apple. And what I mean by that, and hopefully it doesn’t sound egotistical, but in my mind, if you kind of take a step back and think of a place like Apple, they have a very recognizable aesthetic. Well, what does that mean? That means that there are rules that inform it and that there’s kind of like a construct and a framework for how they think about it. And so, if you can understand those things and get good at those, you can take on almost any project and figure out end time how to execute it in an Apple way.

And so, I’ve kind of gotten to that point and I had this moment where, again, I did this kind of flash forward, saw myself at Apple 10 years in the future, and thought that that would’ve been perfectly fine. And there are still times when I think back and wished that maybe I’d stayed a little bit longer just because there were such incredible people there and I learned so much and just enjoyed working with them, but I felt like that probably wasn’t the best thing for me. And part of what inspired me in that was, what I alluded to earlier, Apple has a lot of contract designers, and typically those contract designers, they don’t work at one company for longer than six months.

And one thing I observed that I thought was really interesting and different about the best of these contract designers were that when they were teed up a problem, they could look at it from ten different angles. And so, they could say, “Okay, I know,” as an example, say, something like take an example that came out today. So, Apple announced these AirPod Max, like headsets that you put on your head that literally are like headphones. And so, you would get teed up a project, like, “Hey, here’s this thing we’re going to launch soon. Figure out how to tell this story on a marketing website.” And you need to think that through.

But what I found fascinating about the people who had kind of a broad body of experience was they could look at it from a bunch of different angles. They could do a dark version of that layout, a light version of that layout. They could do something that felt super pop culture-y. They could do something that felt really minimal and restrained, and I thought that there was something really special there. And so, the kind of story I put together in my mind was, “Okay. Well, I think part of that is they just get to flex different muscles. They’re constantly taking on different challenges.”

And so, what that led me to think about was rather than stay at Apple, which would’ve been perfectly fine and would’ve been a great outcome, but rather than doing that, I think it’s time for me to challenge myself. And so, what I ended up doing, which was not at all common at the time, was leaving Apple, which when I was there no one left Apple. You didn’t leave Apple to go work somewhere else especially as a designer, and you definitely didn’t go to a startup, but I decided that I wanted to go and join Square. And Square, at that time, was about 50 people in size, it was in San Francisco, it was right in the city, I didn’t have commute, so that’s why I made that leap.

Pete Mockaitis
Very cool. Well, I want to push fast forward a little bit. So, you went to Square, you did some great things, and now you’re the CEO of Flow. How did that come to be? And what is Flow?

Daniel Scrivner
Great question. So, yeah, I guess I’m trying to figure out how to back it into this question. So, if we go back a little bit in my story when I was really young, one of the things I talk about was just this belief that if you are interested in something that you could figure out how to do that. And I give a tremendous amount of credit to my parents. So, growing up, we would do things like it was very common, probably happened once a month where we would all get in the car, drive down to the biggest library nearby, spend hours and hours in a library.

And so, one of the things that I got, I have two younger brothers, we would all, literally all five of us, we’re a five-person family, we would split out, all go to different levels, find the books that we were interested in, and we would spend hours there. And at that point in time, we were kind of young, say, 10, 11, 12 kind of age. And so, one thing I got fascinated, just hooked on, that I can’t really still put my finger on it, and say, “Why?” was business and investing.

And so, in high school, I was reading books like The Millionaire Next Door, or, Rich Dad, Poor Dad, or, I can’t think of other ones, but like largely business and investing books that typically people aren’t interested in let alone in high school. I’ve just always been fascinated by that, and that’s something that still, today, I’m always…it’s another obsession I have, is I just love learning from investors. Why? Because I think they’re experts at kind of thinking through industries and companies and which company has the best odds to success and why. And I’m also really fascinated with entrepreneurs, and this is the idea of creating something of value that you end up charging more for than it takes to create, which still, to me, feels like kind of pulling off a magic trick that someone is willing to pay for that even though it costs less to make it. It generates profit and you can invest that in other things, so I have these interests.

So, fast forward, I end up leaving Square after five and a half years. At that point, the company had IPO’s, we were 1,500, probably 2,000 plus people at that time, had an incredible experience. But for anyone that doesn’t know, being at a company that goes from 50 people to 1,500 or 2,000, and from having a little bit of venture capital money all the way to IPO in five years, it is a brutal experience. It’s wonderful in so many ways but it is also an incredibly trying and difficult experience.

So, I got to the end of that, was super proud of what I had done when I was at Square, and the team that I was able to work with and helped build, but I knew, again, that I wanted to flex some different muscles. And so, what I did leaving Square was I started kind of exploring things that was entrepreneurial-like and investor-like, so I did. I started doing some venture capital investing, some seed investing in companies. I now have a portfolio of over a hundred that I’ve built up and I’ve learned a lot from that. I also started advising companies. One thing in San Francisco that, this is maybe changing today, you know, San Francisco is changing quite a bit at the moment with the coronavirus and just all the effects that that city is feeling.

But at the time I was there, it’s just packed with people that are really good at what they do, they have really interesting ideas. And so, what that means is there are a lot of startups that don’t get design but need design to be successful. And so, I started working with some of those to help them think about how to think about design on their side.

Fast forward a few more years, and I ended up…so Flow is owned by a company in Canada called Tiny. And Tiny is like a mini conglomerate. You can kind of think of it like a mini-Berkshire Hathaway. And I knew one of those founders, Andrew Wilkinson, for about 10 years, and this was going back, it’s like very serendipitous, but going back to being a designer early on. It’s a really small community. So, we kept in touch and kind of he was a designer, I was a designer, we would both kind of check out each other’s work and loosely stay in touch. Long story short, fast forward a bunch of years in the future, and he now has this company that has many sub-companies, Flow is one of them.

And so, for a little context about what Flow is. Flow, at this point in time, it’s a 10-year-old company. We focus on task and project management, software, largely for teams. And the way we excel, the way we kind of compete is by offering people a beautifully made product that is powerful but it doesn’t feel bloated and it feels like something you’re excited to work in. And the metaphor I use there a lot of the times is like WeWork office versus a cubicle. And if you think about productivity software, a lot of productivity software is the cubicle land, and we try to create this beautifully crafted piece of software that teams need.

So, we went to grab coffee. Flow, at that point in time, was not doing super well and they felt like they wanted somebody to come in and take over and someone ideally with design background that could kind of invest a ton in the product, create a vision for the product of where it was going to go from there. And so, I joined Flow two years ago, and over the last two years, I’ve been working on turning around the company.

Pete Mockaitis
All right. Well, what a beautiful tale from making websites to you are heading up a company and are investing in businesses that are really cool. By the way, I use Superhuman for my email and I love it.

Daniel Scrivner
I love that.

Pete Mockaitis
So, wow, so what a journey. I’m drawing my own little lessons about really digging deep and then challenging yourself and learning from the people around you and keeping those relationships alive. But since we’re actually towards our final minutes here, why don’t you boil it down for us in terms of what do you think are the top do’s and don’ts for professionals looking to grow a career and advance in, hey, more fun wins, meaning in money, as we say here? If you want more of that over the long arc of your career from age 20 to age 60, 70, top do’s and don’ts, lay it on us.

Daniel Scrivner
I could probably talk about this for an hour so I’ll try to be as concise as possible just because I think there’s so many…like, one thing I think you’ll learn over time by working in a lot of different companies, by being at different stages of your life at different companies, it’s a very nuanced thing. So, I will share, I think, what’s helped me and people can decide whether that’s useful. But I think the big things for me is, ideally, you’re doing something that meets that bar of obsession. Like, in my mind, I’ve got a two-year old now, we’ve got another one coming on the way this right around Christmas, and with my kids, I think, the focus there is very much I just want them to find something that is energy-giving and life-sustaining. And I think if you can do that, then you have this…it’s almost like a nuclear fusion reactor where you have something that is just never going to run out of juice.

The goal, in my mind, initially was I wanted to find a couple of things, and at this point in time, that’s design, business, and investing, that I can think about, obsess about, read about, and try to get better at over the long course of my life. And so, find those things and then pour yourself into them. And what I mean by that is I highly encourage people, and again life is a single-player game, you have to decide if this is applicable for you. But, for me, something that’s always been really helpful is you find that thing that you love, then pour yourself into it. And what that means is not only giving 100% at work but, ideally, also doing stuff outside of work that challenges yourself and develops muscles that are probably related to what you at work but might help you prepare you for your next job, might help you prepare for the job you want five years or ten years, or what you want to be doing.

And I think back to my time at Apple, and I would work a full 10-, 12-hour day, get on the bus, do this fun little icon project. I didn’t do it every day. There were definitely days I was burnout or I just needed to shut off my brain but I’ve always had stuff like that going on the side. And I think people have different opinions about that. In my mind, I do the things that I love, and so what that means is there’s very little distinction between work and play, or work and real life. And so, I think that blurriness is really helpful.

And then I think another thing that I would suggest is to challenge yourself. Like, something that I have distinctly found is that the majority of people I’ve worked with are kind of limit their own trajectory by the belief they’re willing to have in themselves, the confidence they’re willing to have that they can overcome any hurdle, and just this deep sense that if they’re interested enough in something, if they want something bad enough, they can figure it out and they can do it.

And this isn’t a anything-in-the-world-you-can-have-go-for-it type kind of pep rally or speech. It’s just I think the way to kind of think about it is this very soft, just in the background confidence of if there’s a challenge that you see in front of you, believe in yourself, bet on yourself, and know that if you just keep putting one foot in front of the other, and you can find a way to push through discomfort, that there are really good things on the other side of that.

And then the other thing I would say is really throw yourself into that growth curve. I almost try to visualize it in my mind of I always want to be in a place where I’m pretty uncomfortable. Ideally, if I’m in a job or doing something and I’m committed to it, I’m really excited about it, I want it to be slightly out of my comfort zone. And I think this role that I’ve taken on with Flow is certainly that. The role I took on early on at Square was certainly that. When I was at Apple, it was certainly that. And I think if you string together kind of subsequent experiences that step, by step, by step, challenge you a little bit more, get you a little bit out of your comfort zone, make you do things that you don’t feel like you’re qualified for or you don’t think you can really do yet, I think the trick there is like a lot of people have this idea that, “I’ll do that once I can do it.”

And if that’s the way you think about it, you’re never going to do it. You just have to start doing, be willing to be bad at it, be willing to be uncomfortable, be willing to kind of cringe even at the quality of your work initially because that’s the price you have to pay in order to get better.

Pete Mockaitis
Well-said. Thank you. Well, now, could you share with us a favorite book, something that you really dig?

Daniel Scrivner
Yeah. The book I was thinking about kind of before this interview that I think might be really applicable, maybe people haven’t heard of, that I really enjoy is a book called Principles by Ray Dalio.

And for a little bit of background there, Ray is the founder of a hedge fund called Bridgewater, it’s the largest in the world, they have a very different culture where they really try to go all in on this idea of meritocracy which is that there’s not really any hierarchy; it’s just kind of a group of peers, and anybody is as good as anybody else and it’s all about kind of the arguments you can make and the work that you’re able to do.

And so, that book is the output of the last 30 plus years of trying to build this company, and it really is what’s in the title. It’s a handful of principles that apply to working in groups and working as an individual. And I’ll stop there, I won’t spoil it, but it’s a thick book. I highly recommend you get the hardcover just so you can open it up and flip through it. You do not need to read it from cover to cover but it is an incredible work.

Pete Mockaitis
And a favorite habit?

Daniel Scrivner
So, something I’ve been thinking a lot about, and this falls into the vein of like, “I’m not good at this yet, but I see the value in it and I want to double down on it,” is taking time to reflect each week. And this is something that I think, if I were to go back in time, this idea of reflection and what does that even mean, where you’re kind of pausing, you’re not doing any work, you’re going to stop sprinting, you’re going to stop focusing on your to-do list, you’re going to stop caring about your email, you’re just going to stop. Ideally, go somewhere where you can kind of think by yourself and sit down, and just really reflect on how things are going at the moment.

And, for me, I try to do that once a week for at least an hour. I have somewhat of a structure, I’ve a few questions I ask myself every single time. Some of those are really simply things but these are, at the end of the day, really profound questions, like, “Are there opportunities that are around me, or I have access to, or I see that maybe I just haven’t recognized?” And, especially in my role now, that’s true all the time.

Another one is, “Are there risks I haven’t recognized? How are things going? What’s going well and what’s not?” But I think taking time to reflect, the kind of metaphor I would have with that is, I think, reflection is something that almost none of us do often enough. The reason it’s important is because anytime in your life that you have a goal, you need to be able to know how you’re tracking and course-correct. And what I found in my own life is I would reflect once a year, maybe by doing New Year’s resolutions, or once a month, or once every six months, and that’s okay. But I think if you can get that down to where you’re spending a little bit of time, it can even be 20 minutes or 15 minutes once a week, what it allows you to do is it just tighten up and kind of keep you on track with where you’re headed. So, I would say reflection is big.

Pete Mockaitis
And if folks want to learn more or get in touch with you, where would you point them?

Daniel Scrivner
They can visit my website to see the podcast episodes I record, to see the stuff that I write at DanielScrivner.com. You can also follow me on Twitter @DanielScrivner and they can learn a little bit more about my podcast if they’re interested at Outliers.fm, and about Flow at Getflow.com.

Pete Mockaitis
And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Daniel Scrivner
I call it kind of the alpha challenge but one thing that I have written on a Post-It that’s a little bit trite but I find it really helpful is just, “If you weren’t afraid of the consequences, what’s something that you would try that you likely wouldn’t try otherwise?” And so, I think asking yourself that question, really thinking about that and being open with what that answer is, bring that whatever answer you write down, you have to give yourself permission, you have to believe in yourself that you can go and figure that out, and you can go and do it.

And so, I would challenge people to ask themselves that question, “What’s something that you would want to do that if you didn’t care about the consequences and weren’t looking at feeling or any of that stuff?” and take that answer and bet on yourself and figure out where to take that.

Pete Mockaitis
Daniel, this has been such a treat. I wish you lots of luck with Flow and your challenges and all you’re up to.

Daniel Scrivner
Thank you so much, Pete. It’s been awesome.

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