Focused - 46: Being Comfortable Is Not an Option, with Jaimee Newberry

Episode Date: May 1, 2018

Longtime web developer, tech executive, startup co-founder, inspirational speaker, and coach Jaimee Newberry joins David and Jason to discuss her own journey, when to go out on your own, when to walk way from projects, and how to deal with unexpected success.

David Sparks and Jason Snell spent their careers working for the establishment. Then one day, they'd had enough. Now, they are independent workers learning what it takes to succeed in the 21st century. They are free agents. Welcome back to Free Agents, a podcast about being an independent worker in a digital age. I am Jason Snell, and I'm joined as always by my fellow host, Mr. David Sparks. Hi, David. Hi, Jason. We're back after a fortnight, and it is time for an interview.

Yes, I'm very excited about today's interview. Welcome to the show, Jamie Newberry. Hello there. I'm so excited to hear that you're excited because I, too, am excited. Lots of excitement all around. Well, for those that don't know Jamie, she is a geek and a free agent from birth, as she explained to me a few days ago, and always hustling. Jamie's been busy with Martian Craft. I know you're on the board over

there. Are you still working with them at all? Probably not, I would guess. Just the board, I mean, which is some work, but yeah, that's pretty much the extent of it right now. But Jamie extended her free agency to a business called Picture This Clothing. She started her own company and it went, I guess I'd say viral. I mean, you were on television. I mean, I don't remember. Was it the Ellen show? I mean, when it first started, it was crazy.

It was Harry, Harry Connick Jr. show and a couple other like Fox television and Michaela on HLN network. Yeah, there were a few TV shows, but it mostly went viral through Facebook. Interestingly, that was the big the big thing. Yeah. Well, so but Jamie, after doing kind of her own thing for most of your life, you came up with this business and it just it really just took off. And that's an interesting thing we want to talk about how do you deal with crazy success with a new venture um but so you're doing that and uh you know welcome to the show thank you so much for having me it's it's really an honor to be here i love both you guys you know our paths have crossed at conferences and tech things past it's an honor to be here with you both so what did you mean when you told me the other day on the phone that you've been a free agent since the beginning?

You know, I think, boy, you know, I got my first job when I was 12, washing dishes, cash under the table sort of situation in the one restaurant in our town. I grew up in very rural Nevada. I was born in Vegas, but moved to rural Nevada with my family in fifth grade and when I was in fifth grade and got my first job at age 12. And I think that like kind of was the start of it. Like I had some money to spend and things that I wanted and I liked that feeling. But my parents were really big advocates of, you know, working hard and loving what you do. And I actually really loved my dishwashing job until I was 15. And I was able to graduate into waitressing at that one restaurant while also, you know, being a high school student.

And so doing that on the side when I was 16, I got to do some other extra work. So I had that job. And then I also, my dad owned his own sand and gravel company. So he was kind of an entrepreneur. I remember many, many family receipt sorting activities throughout the weekends and stuff. But I got to work for my dad's company too. Everything from operating a loader, a big heavy equipment loader, to washing heavy equipment, to driving a pilot car, to whatever he needed me to do, basically. I just had to stop for a minute and think about Jamie driving a tractor. It was like a big loader, like a big old scooper that scoops giant dirt rocks and things into a, yeah, into a crushing machine.

So yeah, I do think that plays a role though, for, for a lot of people that kind of go down this road that they grow up around. I know entrepreneur is such a loaded word, but I still like it. You know, they,

they, they grow up around family members that have their own businesses. And, and I think that helps you from a very early age to think that that's an option in your life. For me, nobody around me had their own business. And it was it was something that was so foreign to me, it took me a long time to come around to the idea. Yeah, you know, and it's interesting, too, because I think you're right, it definitely, it shapes one aspect of your thinking. And I had like, you know, my dad, who was kind of

like, Oh, I like this job, I'll do that for a while and I'll start my own company. And then if it doesn't work out, he would go back to work for somebody else. And, you know, he kind of oscillated through those lifestyles, I guess, on and off. And my mom was sort of like the stable and she was an accountant by trade and she did the accounting and she was the stable. She's like, you need to be bringing in money, you know, like, we can't survive like this, or whatever. But she had that sort of fear and stability. And like, so, I kind of go back and forth between their two personalities. I feel like sometimes that, you know, you need the security and safety of a job. So, I've definitely, you know, had jobs. But I also have that sort of free spirit mindset that my dad had, where I want to love

what I do, no matter what it is. Maybe it gives you a good balance, really, you know, the idea that you can do things, but also you got to figure out how to pay the bills. Yeah. And, you know, and I think a lot of that is, you know, a decision in a lot of ways on what kind of life, you know, what does success mean to you? And what does, you know, I don't know, what does paying the bills look like for you does, you know, I don't know, what does paying the bills look like for you? How many bills do you have that you have to pay? What's required? Because I think you design that. You decide what, you know, do I need a, you know, a bigger house? Do I need the dog in the car? What kind of car? And, you know, all that kind of thing.

Or do you live very simply? You know, we've seen like this big tiny house movement not to like completely derail the topic but you know i mean like people want to do more they want to travel more they want to see more and there's like this big shift in what do i really need has happened in the last you know five to ten years and it's really cool to see jason did you i don't think we ever talked about that on your kind of origin story show were there a lot of entrepreneurs in your family growing up? I think we talked about it a little bit, and I was actually struck by something Jamie said about how, you know, you absorbed that from your dad. My dad was an orthodontist, and I was thinking about how that is an industry, medical, dentists and doctors and all that, where the idea of a private practice is like a common, maybe a little less now, but it's a pretty common thing.

of a private practice is like a common maybe a little less now but it's a pretty common thing i think that most often their industry was people out on their own running their own business putting up their own shingle and what's funny is that it didn't sink in for me like i think it maybe it did for jamie to the point where i i just had this for me it was like i'm gonna get a job in the media and that's gonna mean it's a big company because Because back in those days, that was, you couldn't hang out a shingle on your own. You had to be part of a large organization. And I do remember my parents, especially my dad, being a little, asking me lots of questions once I got a job and was working full time and had a boss and all these things. And I had that moment where I thought, oh yeah, he doesn't do this.

Like he did in his past, but in the last 20 years or 30 years or whatever, how long he'd been working at that point on his own, you know, he wasn't he didn't have a boss and he was he was doing his own thing. him. And I only in the last few years have I come around to the other side of it. But I did not internalize that so much, perhaps because of what industry I was planning on going into. And so I totally didn't pick up from my dad who was who was running his own business, any of that stuff. It was like I wasn't I was already looking past it. And so it's ironically, now I am the one who is doing the same thing. This episode of the free agents is brought to you by timing the automatic time tracking app for Mac OS, head over to timing app.com slash free agents and save 10% when you purchase and get a 14 day free trial. As a free agent, I cannot understate the value of knowing where you're spending your time.

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And then you get to save 10% off when you purchase. So stop worrying about time and focus on doing your best work instead. when you purchase. So stop worrying about time and focus on doing your best work instead. Once again, that's timingapp.com slash free agents for the free 14 day trial and 10% off. So Jamie, you were kind of a free agent for a long time and you've been kind of jumping around. As I understand you, I don't know all of your career, but the public facing stuff that I've seen you do is you do move around a little bit, and you have tried different things. Did you ever feel any resistance to that? I mean, once you get in one thing, is it hard to move to the next?

You know, I think that's really interesting. You know, for the bulk, well, you know, now I'm on the other side of that, but like as a younger person, I graduated with a metal sculpture degree, which was like when I graduated, I was like, well, that's useless. Now I have to figure out how to make an income. And I was it was 1998 when I graduated from college. And and so like, I and I was married at the time. And my husband at the time was into like video production work. So I'd done like a bunch of freelance stuff with him. And he, we were moving to the Bay Area, the San Francisco Bay Area. So, I was going to do grad school there and all of that. But like, I ended up like falling in love with the web, right? In 1998, I was just enamored with animated GIFs and all of those things. And I was like, I want to make the web. I didn't know how to use Photoshop. I didn't know how to,

you know, do any coding, but I ended up with this job in a video production company, just, you know, doing like production assistant work. Basically, I would help coordinate events and do whatever the office manager, the owner of the company basically needed me to do, which was a lot. And she was awesome. And I learned a ton. But what happened over time is I had a lot of downtime, and I would be the only one at this office. And so in my downtime, I taught myself how to use Photoshop and to use BBEdit and like kind of reverse engineer websites. Basically, I would look at the, you know, use view source, and then I would copy and paste it into BBEdit. And then I would plug things in on my own to try, you know, make my own graphics and then start dropping in graphics and see what would copy and paste it into bbedit and then I would plug things in on my own to try you know make my own graphics and then start dropping in graphics and see what would happen

and and that was really like the beginning of it all and I became in love with it like I absolutely I was like this is what I want to do this is who I want to be I want to be a web designer and and so I went down that path and you know eventually I left the film and video company and I got a a job as a production artist at a web startup, like a doc in the.com era, the whole, that first startup boom, um, out in, you know, the Silicon Valley area, um, at a, at a company that, yeah. And basically I started as a, so this was like my real first, my first real, real job. Um, they, you know, paid me a salary. I think I had gone from making like 10 bucks an hour and doing a bunch of temp work to, um you know, paid me a salary. I think I had gone from making like 10 bucks an hour

and doing a bunch of temp work to they paid me like $40,000 and they offered me benefits and stock options, which never vested, but that's okay. It was still exciting. And, you know, so that was like my first legit job, like real, real job out of college. And it was about a year after moving to the San Francisco Bay Area. And I got this job by just applying and teaching myself Photoshop and stuff on the side using Classroom and a book, if you remember those. It came with a DVD ROM. Oh, yeah. Right in the back, probably. Yeah, yeah. Right in the back in the little plastic sleeve. And I taught myself how to

use Photoshop. I got this job and then I was learning on the job with people who were really good. And I learned how to use Illustrator on the job. And I did that until the economy shifted and the whole dot-com thing collapsed around 2000, 2001. I could see the signs, the writing on the wall. We actually, our next-door neighbor at that startup was a company called Webvan, which was like grocery delivery in 1999, you know, which now is super awesome and stuff. And we thought it was awesome at the time, but it just didn't go. And when they closed their doors, I was like, okay, I got to start finding another job because if Webvan's not making it it there's no way our company is making it so i ended up moving back to vegas getting a job as a web designer um for unlv where i had

actually gotten my undergrad degree and is this where the burnout story comes in because i've seen you give your talk about about burnout and getting through it and you know as somebody who real i mean i was thinking about that a lot because i saw i saw you give that uh talk while i was self-diagnosing as as burning as burning out um man and that was that was when you're a web designer that you that you burned out right um kind of so like you know my career so that was around 2001 i moved back to las vegas from san francisco i moved back to Las Vegas from San Francisco. I moved back to Las Vegas in 2001, got this web design job, loved it, did it, worked at the university. And I was like coming off, I got to tell you a side note, coming off of the pace of the,

you know, dot com era in San Francisco to an education environment. It was like running a thousand miles an hour into a brick wall. And I couldn't get, so I did tons of side work. I was doing freelance websites for anybody who needed a website. I was like, I'll design your website. And I did like my very first, my very first, it was a PowerBook, I think back in the day, right? Not MacBook. I got my very first PowerBook in exchange for my very first Flash website. So, I built this website in Flash and they paid me with a case of Dr. Pepper and a laptop. And that was like everything to me. So, that was back in like 2002. And then, so I was

working at UNLV, I was doing side work, which UNLV awesomely encouraged because they felt like it benefited them because you were learning, you know, to better yourself, your trade, and you, and then in turn be better. But I also ended up teaching at the university, also in parallel. So I was doing like three jobs, kind of. I was teaching management information systems, interestingly, and, and then I was doing websites on the side, and I was doing my full-time job. I didn't have kids at the time, needless to say. I got to interrupt for one second. I'm still thinking about this. So you said, I'm going to make you a website. Now, did you, was the first demand the case of Dr. Pepper or the Mac? So this company, it was actually the company that I did this for was the company that I had worked for in the San Francisco Bay Area

as a production assistant. And, you know, when I started dabbling with stuff, I'd built their first website. And then when I left, they had hired somebody else to build their website, like a new version, and they weren't very happy with it. So they asked, I had already moved back to Vegas and they said, Hey, would you be willing to do this? Like, you know, in your, in your free time or whatever, would you be willing to build us a new website? And here's what we're looking for. And I did it. And, and I just, they asked what it would cost. And I was like, well, I need a I need a computer to do this. So they actually they fronted the computer. And then, you know, so I did the work on this new computer.

And they said, here's some cash if you want to go get your case of Dr. Pepper. So we don't have to pay for shipping. So that was kind of how that went down. But they pay for it up front. And I did the work. I worked hard for it. And they loved the website. And I think it still exists on the, uh, like the way back machine or whatever.

If you look for old, I'm going to totally start doing that. I'm like, I'm going to need a, uh, a tickets to star Wars and something really expensive. Yeah. And you know, it didn't occur to me at the time to just ask for the cash to buy it. You know what I mean? I was just like, I need a computer to do this on. Because my husband at the time, we shared a computer and he used it most of the time. He was a video editor and, you know, he was using his computer all the time.

So I needed one. And that was and I was, you know, young and poor and, you know, working my butt off to make it work and doing what I loved. You were definitely working your butt off. So, I think it was teaching, coding for school, coding for third parties. Yeah. When were you sleeping? You know, this is a funny thing, but I didn't require a lot of sleep in my younger days. That has changed significantly now as I've aged and I have kids. But around age 38, that all changed for me.

But I seriously was pretty good with a couple hours, three, four hours of sleep a night. And I marvel at that now. I don't think I could do it to save my life today to only get two or three hours of sleep for multiple days in a row. So, I guess kind of going back to answer that question about like, when did the burnout happen? I actually built this really kind of awesome career as a designer. You know, I would say it started in around 1998. And it carried me all the way through in many iterations. You know, I was doing the teaching and I was doing the web design thing.

And then I ended up leaving the web design job at UNLV to take a job with a company that was doing awesome, awesome stuff. And they were called Eat Drink. And I became a partner after a year of joining. I joined as a project manager slash interface designer. So I was kind of wearing a couple hats there. But it was these just awesome dudes, basically, that ran a company. They had an office in Vegas and an office in Chicago, did mostly work for large agencies like Saatchi & Saatchi, Leo Burnett, like big clients like Disney and, I don't know, Procter & Gamble and all kinds of, you know, hearty McDonald's, big name clients. They were doing cool stuff because they were really awesome at like Flash

and animation and stuff like that. And so I jumped on board over there, left the stability of the university to go this wild little tiny shop. And I fell in love, became a partner and rode that out until 2008. And the economy shifted yet again, as it does. And we closed our doors to Eat Drink in 2009. Zappos was a client. Zappos offered me a full-time position about a month or two after. And it's interesting in that sort of transition period, it was 2009. I had my second child in February, closed the company in March,

started at Zappos in April. And what a crazy year that was. Oh, and then also went through a divorce that same year. So that was a big year for me. Not burnout year, though. Burnout didn't come until about 2012, 2013. My dad passed away. It was April 9th of 2012. And I actually at that, by that time, so I had left Zappos, um, by that time I had joined a company called Black Pixel and I was, I loved that job. I loved that role. I joined Black Pixel in 2011 as their director of user experience. So like my job as a web designer had grown and changed. I'd become a partner in my own shop and a lot of different iterations. And while I was at Zappos,

I was a manager of product manager and manager of user experience or whatever. But my first project there was overhauling the web, the look and feel of the website. My second project there was the very first mobile apps for Zappos to run that team and lead that project and so and we did ipad iphone and then android and those were really successful at the time in my first foray into the mobile realm so then my job kind of shifted into mobile focused stuff rather than

web which was great hit me right exactly the time i needed to kind of shift gears out of the web and right into mobile so that carried me a couple more years until I lost my dad. And then when I lost my dad, it was one of those jarring, you know, I'd had loss before I'd lost my brother when I was 11. I lost my mom when I was 28. And I thought that I had the whole loss thing. Like I got this, I know how to work through it. I've done it before. But when I lost my dad, it really hit me differently than I expected. And I just went into this downward spiral. And so even though I had this job that I really enjoyed the people I worked with, I enjoyed the work that we were doing, I enjoyed the clients that we were working with, but I emotionally just disconnected. And as a, you know, a design

person, you can't disconnect. You just can't. It's an emotional job, design as it should be. disconnect. You just can't. It's an emotional job design as it should be. And I felt like I wasn't doing my work justice or their, you know, company justice to keep doing it if I couldn't connect emotionally. And so, I just quit. I didn't have a plan. People were like, what's next? And I didn't have a what's next. I just knew I needed to focus on what was important. You know, that's something we've never talked about on the show, but just in my day job, I deal with a lot of clients, and a lot of them are free agents. I haven't had this problem at this point. I've only been a free agent really a few years now, but a lot of people aren't ready for that when there is a loss in the family. You know, you lose somebody important to you. And if you have a job where you're getting a salary and you show up and you

have, you know, a disconnect for six months, sometimes, sometimes it takes that long to get over something like that. You can almost get by, you know, when you're working for somebody, you can, you know what I mean? But when, when you're on your own that can be devastating to you and that i don't really have the answer for it but that's something to be wary of i think it definitely is aware of yeah and that's where man you know it is interesting because i i literally felt like i couldn't design anymore i couldn't do it and i still i honestly haven't really gone back to design in the same way that, you know, that I used to do it. And honestly, like, you know, people would ask me after that, like for advice, like, can you take a look at my app? Cause that's what I did. You know,

I was with black pixel and I, I was helping people with, you know, I was doing talks about how to make your design connect with people. And, and, you know, like I was doing some really awesome talks and, and I was really passionate about, I had built a career doing something I loved. I loved my work as a designer. And then to just feel this disconnect from it was scary. Um, I, at the time was a single mother of two girls. I I'm, I'm still an independent mom, but I'm not single. So I try to make that distinguish my, um, this, yeah, to distinguish that. But, um, but you know, like, so it was scary to feel that, but at the same time, you know, I, I have a good skillset. I have a broad skillset. Um, you know, I can manage

projects. I can write business plans. I can, I can design if I have to. I can, you know, help people solve business problems. I can help people think about things from an empathetic perspective. I have a lot of skills to offer. And, you know, it was really just, I had to take time to really think about what was important to me and prioritize that and not just do work for the money. You know, I was making good money. But at that time, I guess I was in a lucky position. I built a good position for myself to say, you know what, I need to take time. I have a good safety net. I'm a good saver. And you know, and we talked about this a little bit, David, when we connected before this call, is that that sort of financial independence, like building a financial stability so that you have some freedom. And so if something like this happens, you have a little

time to recover or you have, you know, to do what you need to change things. And honestly, like I ended up coaching, I ended up doing coaching. And I did that talk about burnout. And then you might be surprised how many, you know, I was still talking in the tech environment, Mac developers and app developers, and how many developers came to me afterward or emailed me afterward and said, help me, I'm going through this, I need your help. How did you do it? How did you get through it? And I ended up, you know, making a career out of that, basically. So, I ended up shifting what I was doing. And even though I still consider there's very much a design component threaded through everything I do, that's my way of thinking. You can design your life the same

way you design a product, the same steps, you know, and I feel like I've proven it. And, you know, I've gone on to do this company. That was something that I also designed because I know how to design damn good products, I'll say confidently. But if you can shift that lens and design it toward yourself or, you know, aim it at yourself and design your life the way that you would design a product or make a product if you're a developer, the same tools apply, interestingly. This episode of Free Agents is also brought to you by FreshBooks. All of you freelancers out there, you know how important it is to make smart decisions about your business.

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agents and enter free agents in the how did you hear about a section? Thank you to FreshBooks for supporting free agents everywhere. So how did you deal? So as you came out of the burnout, you started doing consulting, but eventually you started some new projects as well. What led to that? What led to that was making this decision. Okay, first, I'm going to leave this full time, comfy, awesome job that I have. And I'm just gonna see what happens. I've got, you know, about a six month safety net that I had built up in savings. And, and I was like, okay, I have a little bit of time, I figured I'd give myself three months, because it probably takes a, you know, another three months to actually find another job. I figured it could take longer. I don't know,

but that was where I was at at the time. So I had six months living expenses in the bank. And I was like, okay, I'm just going to do this. Here I go. And I started writing. The very next day I started writing and just like a public blog post or whatever. Here's what I'm doing. Here's what I'm going through. And then I started getting some offers to write for money, which was awesome. So I was like, sweet. And then I got this other, you know, like people reached out to me. They were like, Hey, heard you left. Would you be interested in this? And lots of offers. I was very, very lucky that a lot of people just like reached out and said, Hey, would you be interested in this? And I found one that aligned with what was important to me at that time. I didn't want to design thing, but I found

somebody was looking for help writing a business plan. And it was it ended up being a year long engagement at a very reasonable volume of hours per month, it was like 60 hours a month. And it was enough to pay pay the bills and not like, you know, eat away at my savings and just keep moving. But also I had time. So it was interesting how that happened. But I feel like I designed that, you know, like it's not like I just happened and stumbled into this stuff. But then like I just kind of kept working through this stuff, right? And so I started the coaching thing. I started writing about what I was working through and the progress and how I was doing it and what would happen when I did this and what would happen when I did that. I ended up

starting this little thing called Tiny Challenges. There's a tinychallenges.com where Daniel Steinberg and I did, like, we did a few episodes of a podcast. And then, yeah, we kind of moved on from it. But it was cool. And people were, we had a Slack channel and kind of shut it down. But one of the side things, I had designed time into my life. I wanted to own my time. That was my biggest objective. I want to own my time. I want to control when I do what. I don't want to sit at a desk or have to be there for a phone call I don't want to take or whatever. I just wanted to own my time. And that was the goal that I'd set for myself. And by coaching, I was able to do that. I was able to schedule phone calls when I wanted to have them and people pay me for my time. And I ended up doing that on a corporate level as

well. I would do corporate coaching. So companies were hiring me. I had like a telecom company from Australia hire me to help them with emotional writing and with their team, their team's emotional happiness and well-being. And then I ended up helping Martian Craft in a similar capacity with their design team and just coaching. And, you know, at that capacity, and I set the hours, I set the terms, I set, and then that Martian Craft job rolled into a full-time position as a COO over time, but it was still remote, so I was still working at home and still able to kind of own my time. But in the sort of like in parallel, you know, I'm never doing just one thing. I was writing. I was doing public speaking.

Most of those things pay a little bit on the side. But then I was also doing stuff like I was spending time with my kids and in one of the things that I did was make a dress that my daughter drew this picture of a dress and I was like hey we could make that I have just enough sewing skills to be dangerous and so I took her to the fabric store we spent like a hundred dollars in fabric and I spent the next three days um 12 hours across the next three days like constructing this dress based on her drawing and and that wasn't like how picture this came to be instantly it was over time that wasn't the aha moment but I built this dress for her and

I say built it because I patterned it sewed it together it's very different than what picture this clothing does right now but she put it on and the words out of her mouth were, I'm wearing my imagination. And that moment was magical. Like if any, if every parent could have that experience with their kid, it's seriously one of the most amazing experiences. So she wore this dress like endlessly for about three months. I had to like peel it off her body to wash it. So it wasn't gross, But she wore it everywhere.

And everywhere she would go, this brightly colored rainbow dress, everywhere she would go, people were like, that dress is amazing. Where did you get that? And she's like, I created it with my mind. And my mom made it. And she's like, I made it. It came from me, my design. So it was just this amazing thing.

And my boyfriend, Ken, was like, man, you've got something here. This is amazing. Everywhere we go, she gets compliments on it and people want one and kids want one and, you know, they want to be fancy like Zia. And so he came up with the idea to simplify. He's like, well, what if, you know, because at first my response was like, no way, I'm not going to become a seamstress. Like that project was hard. It was labor intense. It was expensive. And there's no way that I can, you know, we ran numbers and kind of looked at stuff and I was like, there's just no way I can make a business sense of this financially. Like it just doesn't add up. Um, and he, after, you know, pondering for a couple more months, he was like, I got it.

What if they just wear the drawing? Like, what if we can use this technology, sublimation printing and come up with our own sort of process. And he designed a like a one printable coloring sheet, which is what you get from our website, picture this clothing.com, you print out a coloring sheet. It's very simple. People color it, take a smartphone photo, upload it back on the site, and we send it back ready to wear. And it's as simple as that. But I really credit Ken with that, that sort of simplification of the concept. But you know, it took a couple months for that to kind of percolate. And then it was the aha moment. What if they wore the drawing? That was really the amazing moment.

And that's how I ended up doing this. So I mean, so you went through I mean, you are you're always, something I admire about you is your willingness to take the leap. Because I think everybody who's a free agent does that at some point. I mean, just getting started or for me, it was giving up the most lucrative part of my business because it just didn't make sense anymore. But everybody has these things where you literally take the leap of faith. But you make a habit of it, Jamie. I think I learned it from my dad. Yeah, well, and I really admire that about you.

And so you did that. You decided, you know, I'm going to get into the clothing business because I had this great idea and we figured out a process where people can, for kids and adults, can wear their drawings, which is kind of amazing anyway. And the interesting thing about this for you was it was an immediate success. I mean, you were on TV. It was crazy on Facebook. Everybody, I remember when it happened, it was just like showing up everywhere in my life. There are people like, oh, have you seen this new company? I'm like, yeah.

And I know that lady, you know? And so, so it was, um, it really was great. And not many people have that immediate success. How do you deal with that? You know,

it's, it's interesting because we really didn't expect that. I think, um, my, my boyfriend, I'm going to quote my boyfriend here. Um,

Ken Finney always says the secret to happiness is low expectations. The optimist outlook on everything. But, um, so, you know, we had low expectations. Basically what we built was a proof of concept. Um, we, we had the idea, we did some prototypes. We called our friend Iggy, who's a web designer to, to make it in exchange for equity, to make this website real. We worked with them on,

you know, branding and stuff. He's an excellent designer. But we worked with him on the experience, the flow, the interaction and stuff, because that's Ken and I are both pretty sharp at that stuff. And he so combined, we created this and we used WordPress templates, you know, something low cost. I mean, it cost us, you know, less than $1,500 to launch that idea as a proof of concept and, you know, a lot of time. So, you know, I'm not billing for hours here or anything. I'm just saying like the actual money we put in, the three of us each chipped in like 500 bucks to cover like, you know, our hosting and our domain name reservations and all that stuff. And so, you know, and to build prototypes, to get prototypes made. We ended up finding a manufacturer here in Las Vegas, 15 minutes from my house,

who could do the kind of print we needed and who did the cut and sew, which was very important for what we do. We don't print on pre-made products that are made overseas. We make everything right here in Las Vegas, which is, it was just hugely important part of the process for us because of the detail. But, you know, and I don't mean to derail from your specific question of like, how do you handle the success? But just to kind of lay the groundwork, we launched it as a proof of concept. And on the morning, you know, like we reached, we reached this point in July where we're like, okay, well, the site's done. Let's test it with

a couple friends who have kids, get some feedback, feedback make the product see how it would actually go if we released it we did it we got a little feedback on some stuff our sizes were a little off and so we made some adjustments and then we were like okay this is it we just let's put it out in the world and the worst thing that happens is nothing happens right like we don't lose anything but that you know $1,500 and a bunch of time. But whatever. We all had other things going. Iggy owned his own design shop. Ken is the other half of the Narwhal app for Reddit. He's, you know, 50% of that. And I was doing COO stuff for Martian Craft. We all had day jobs, basically. And so, we were like, let's just put it out there so the morning of august 17th 2016 i posted a tweet around 6 a.m and by the end of the day oh the tweet just said like hey check out this thing

that some friends and i made with a link to picture this clothing so it pops up with a little picture and everything and we thought about it you know like it we wanted it to be good we didn't want to release just a you know cobbled together piece of crap. We put time and effort into it and make sure we could take orders if someone placed one. What we didn't expect was a write-up by 6 p.m. in TechCrunch. So TechCrunch reached out via email around 4 p.m. and just asked questions. They didn't say anything about it. It was a writer from TechCrunch who just shot an email. I answered it very thoughtfully. I thought maybe they'll want to do a piece on us you know so i'll answer these you

know very carefully and very thoughtfully and i sent it back and then we were like our site's down what's going on and then we discovered there was a tech crunch write-up just a couple hours after i'd responded to that email and he didn't say he was sending you know writing a post he didn't you know really we were just like holy crap a post was just made and and our site's down and so he you know got the site back up and then and then it was just one for the next i don't know like three months um it was just one thing after another and i i feel absolutely honored but it caught us by surprise and i have to say like you know you don't expect that. We had low expectations and we thought, oh, it'd be so awesome if we sold like one, you

know, or 10. And we were just like, well, that'd be so cool. And we could handle like if 10 orders a month came in, that'd be great. We could just keep doing what we're doing and we could handle these orders too and make a little money because we set it up. We didn't, you know, carry inventory. We set it up so it was profitable immediately. make a little money because we set it up. We didn't, you know, carry inventory. We set it up so it was profitable immediately. And, and then, um, you know, so like, you know, so day one tech

crunch write up and then day two product hunt posts us, um, day three, Disney's babble.com, a parenting blog reaches out for an interview. And then day four, um, some other news conglomerate called now this who does Facebook videos reached out and did an interview and they launched their video so all these things kept happening babble.com posted their um their post one week after our launch date so like seven days later and when they posted theirs um huffington post kicked it picked it up and did a post on it business insider did a thing on it um scary mommy which is a big mommy blog, picked it up. Bored Panda picked it up. My Modern Met picked it up.

And then this company. And so, like, all this buzz is happening. And then that video, that company, the NowThis video, they launched theirs the day, it's probably two weeks later after we launched. They posted their video the day before Labor Day. I just remember it was like a three-day weekend, but they posted their video and it got 3,000, sorry, 3 million views in less than 24 hours. And then that next day on Labor Day, the holiday, we did $10,000 in sales. And we were just like, oh my God, it's real now. We had not yet shipped a single order. And that like, we were like, oh my God, it's really real now like we just

proved the concept now we got to get our butts in gear so we we just put our nose to the grind and busted a move and we made it happen yeah i'd call that proof of concept yeah yeah but oh man and then emails started pouring in i had to get help to answer because i was still you know we were all still doing our day jobs but i started getting like 200 emails a day. And I'm not joking, that is not an exaggeration, like 200 emails a day. And most of them I had, you know, I developed some copy paste that I could just answer most of the questions we were getting our FAQs updated on the site and trying to post, you know, do as much as we could, just to preemptively stop people, but you know, from from emailing, and then I had to hire help. and that group went from

10 hours to 20 hours to 30 hours to 40 hours of of help just with customer service um and then um i ended up leaving my full-time post at martian craft in november because it just became it i couldn't do both i couldn't do both and be a mom and do my speaking engagements and all this stuff so um we managed but but man, was it bonkers. Jamie, you talk a lot about all these things that you started and you've had these successes with some of these things. One of the things that we talk about on this show a lot is being able to say no and being able to get out of things that you don't want to do anymore.

And that's another thing. The flip side of what you've been able to do is that if you've got a project, you have shown, I admire this. I'm not saying this negatively. I really admire your ability to say, I'm done with that project. I'm going to move along. Could you talk a little bit about that? Because like you mentioned tiny challenges and you did that for a little bit and then you said, now we're done with this. And like you couldn't do the new projects like Picture This Clothing if you kept all of your existing projects going at some point, you have to say, I'm

done with that. How do you approach that? Okay. That's a great question, by the way. So you remember when I was talking about going through burnout and then it was like, it's not about what's next. It's what's important. And I made this list and, you know, as a designer, every project I do, I do design principles.

And when you outline your design principles, as you move through a project, you, every, everything that you, every decision that you have to make about that project, right? If it's a mobile app, you say, oh, we want to add this feature. Well, does it align with the design principles? Yes or no? If it's no, you get it the hell out of there. And I operate my life in exactly the same way. My what's important list is sort of like my guiding compass, right? It's like, I have this list of eight things that I created and it's like my core values, my compass. And it's, this is what's important to me in my life. And every decision I make, does it align

with one or more of these? And if not, it has to go. And sometimes it may still align. I just don't have, it's not the highest priority, right? Tiny challenges. I still practice and I still do because it has helped me. It's helped me chip away at some of the bigger challenges that I've encountered in life and not being able to do stuff. You know, feeling like I couldn't do it because, you know, excuses are a whole nother thing. I have a talk called No Excuses, if you haven't checked that out, not to totally self-promote, but it really is exactly how I moved through, you know, I can't do this because I can't afford it. I can't do this because I don't have time. I do have time and I can make, you know, it's about chipping away at the big

obstacles. So Tiny Challenges was born out of that. I still practice it. I can make, you know, it's about chipping away at the big obstacles. So Tiny Challenges was born out of that. I still practice it. I just couldn't manage a community around it anymore. I can't prioritize that because Picture This came in and became such a large presence. And I love it. Like, I love what we do at Picture This. I love what we make.

I love that every single day I wake up to new pictures that customers have sent me of their happy kids wearing their clothes or them wearing clothes that their kids made. You know, I wake up to every day there are rainbows and unicorns in my inbox every single day. And I like that I couldn't have designed it better. Like, holy cow. So I love what I'm doing. And so yes, I do have to say no to stuff. I love tiny challenges too, but I can't do them every month right now because my higher priority is picture this. That is what I've decided to make a higher priority. And you know, my kids, of course, like I still drive them to school every

day and I still pick them up from school every day. And that means I have to sacrifice maybe moving as fast as I'd like. I picture this. But, you know, like I do make sacrifices. Like you do have to make sacrifices and you do have to say no. But if you have that compass, I guess it's going back to that list for me of what's important, my design principles or my core values, whatever you want to call them. I have this list and I have it in a place where I can look at it at any given moment, you know, my little notes in my phone. That's where I keep mine. And, you know, everybody's are different.

Everybody's priorities are different. And you have different focus at different times of life, depending on what you're going through, what your life circumstances are. But if you have this sort of guiding light, I guess, this is the source of saying, okay, I really need to look at this and just make sure here's a decision that I need to make. Does it align with my list? And that's how I make those decisions. And when I stick to my list, when I actually stick to it, and there have been times when I'm like, oh, but I need the money or whatever. So, I'll accept this job that doesn't seem like it really makes sense. And then, you know, sure enough, I end up regretting it. And the money is just not worth it and you have to let go. And,

you know, it's, that's one of those things. And, you know, also, it kind of goes back to what I was saying really early on in the call is like, how much are you willing to sacrifice for what you want for designing your life? You know, like, I honestly made a decision when I hit rock bottom burnout. I was like, do I need this house that I live in? I've been in my house now for, it'll be 16 years this year. but could I let go of it if I had to? And, you know, I made the decision like, yes, I could. I could let go of this if I had to. And, you know, maybe live in a camper or whatever. I don't know, whatever I needed to do to make ends meet. I haven't reached a point where I've had to let go of things. In fact, things have just perpetually gotten better. And I have to say, picture this as that. It's, you know, after the viral bliss, you know, you, you got to settle with reality. And it's definitely not viral. But our holiday sales are still amazing. And we've still, you know, we broke a million in sales earlier this year, and we're not even two years old yet. And that's pretty awesome. And good things are happening still. And so, you know,

I mean, it's like, we've been able to pay ourselves a little, but I've definitely had to cut back on a lot of the lifestyle I'm used to. But I think you have to decide, you have, I mean, it's like we've been able to pay ourselves a little, but I've definitely had to cut back on a lot of the lifestyle I'm used to. But I think you have to decide. You have to make a decision. Like, what are you willing to compromise in exchange for taking the chance? And for me, not taking a chance is too great a risk. Like, just being comfortable is not an option for me because it's boring. And you know what?

And that's exactly why you're so successful. Thank you. Because you're always climbing the hill. Well, Jamie, thank you so much for coming on the show. Everyone, you can learn more about Jamie. She's on Twitter at Jamie Jamie with a J-A-I-M-E-E twice. And you're on the web at Jamie, Jamie.com. And you can also go check out picture this clothing.com.

Congratulations on your amazing success. I can't wait to hear what happens next with all of this, with your story. You guys, thank you so, so much for having me. Yeah, we are free agents. You can find us on Twitter. We are free agents FM on Twitter. You can also find us on relay twitter we are free agents fm on twitter uh you can also find us on relay.fm free agents there's a feedback form there you can send us feedback let us know what

you're thinking i miss anything jason nope that's about it i guess you can go to facebook.com slash groups slash free agents group if you want to get together with other free agents and we will be back in a fortnight with more of your feedback that you send in. Like we just said, and, we'll talk about our, our, our own little free agent lives as well.

But until then, David, it's been a pleasure as always. We'll see you in two weeks.