Good Life Project - Lisa Sugar: The Making of POPSUGAR (and a very good life)

Episode Date: September 26, 2016

A child of the 80s, Lisa Sugar grew up obsessed with pop-culture. Little did she know, her childhood fascination would become her career.Graduating college, Sugar headed into the world of media, and then advertising. She was working her way up the ranks on the media planning side. But a little voice kept calling her to write. So, she started a little website, POPSUGAR, on the side.At first, she was writing in the evening and weekends, then pretty much any break she could get. What happened next took her breath away. Turns out, her obsession wasn't just her own. And, her voice was landing in a way that had people reading, sharing and coming back for more.Within a year, more than a million readers were coming to her website, so she quit her job and made POPSUGAR her full-time pursuit. Six months later, with the company now exploding, her husband left his tech-job and joined her. POPSUGAR is now the leading lifestyle brand in the world, with more than 85-million visitors a month and 1.5 billion media impressions/month.Lisa's journey is detailed in her book, Power Your Happy: Work Hard, Play Nice, & Build Your Dream Life. In today's episode of Good Life Project, we dive into her story, how she made the shifts in career, when she knew it was time to ditch the full-time gig and go all-in on POPSUGAR, why she believes in work-life blend, not balance, and so much more.Mentioned in This Episode:Connect with Lisa: Power Your Happy | POPSUGAR | InstagramDarren StarShopStyle Hosted on Acast. See acast.com/privacy for more information.

Mayday, mayday, we've been compromised. The pilot's a hitman. I knew you were gonna be fun. On January 24th. Tell me how to fly this thing. Mark Wahlberg. You know what the difference between me and you is? You're gonna die.

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And it's the fastest-charging Apple Watch, getting you eight hours of charge in just 15 minutes. The Apple Watch Series X, available for the first time in glossy jet black aluminum. Compared to previous generations, iPhone XS or later required, charge time and actual results will vary. Hey, did you hear? I've got a new book out. It's called How to Live a Good Life, Soulful Stories, Surprising Science, and Practical Wisdom. I've been working on this baby for a number of years now. It's the distillation of about 50 years, 50 plus years now on the planet. The opportunity to sit down with hundreds of astonishing teachers and find patterns, you know, things that really, really moved the needle and also sharing a single idea, a single model, a lens on life that you'll hear once, you'll remember forever. And it may guide the way that you

move into the world from this moment forward and hopefully make a really big difference. We have a really cool pre-order initiative going on where we're working with a foundation to plant trees as well. So when you pre-order your book, you'll get some pretty hardcore, amazing extra bonuses and gifts. And at the same time, you will help us plant what we hope to become a good life for us. We are on a mission to plant 10,000 trees as part of bringing this book to life. And I would love your help.

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go ahead and click on the link in the show notes now. Thanks so much. I'm Jonathan Fields on to our show. If something fails, like we learn from that really quickly and we just adapt. So there hasn't been some huge disastrous thing because every day we're trying something new. Today's guest, Lisa Sugar, launched a website called PopSugar back in 2005 and based largely on her kind of obsession with pop culture. She started it on the side, but what she quickly found was that thing that she was doing on the side blew up. She had just crazy interest in what she was doing, quickly had a million readers,

and decided to actually jump ship from her mainstream advertising gig and double down, focus all of her energy on growing this thing. 11 years later, sitting here today, I had a chance to sit down with her and talk about her journey. Pop Sugar is now the top lifestyle media brand for women, having verticals with everything from entertainment, fashion, beauty, fitness. And according to her, something like 1.5 billion global monthly content views across all of their different media. And she's built a really powerful company with 500

people as well. I got really fascinated about her as an individual, about the journey, about taking something which was just this sort of fascination and thing that was deeply fun for her and transforming that into her career and then building a really sizable company and media empire around it and how that happened and also how it changed her along the way. And that's the conversation that we have. She's also the author of a new book called Power, You're Happy, which takes you into that journey to a certain extent as well. And we talk about that and also why, as she sits on top of a very sort of progressive digital media empire, she chose to go and release a book. I think it's an interesting question.

So really excited to share Lisa and her story. I'm Jonathan Fields, and this is Good Life Project. So we're hanging out in Good Life Project HQ, also known as my apartment on the Upper West Side. It's nice just to be hanging and having a conversation with you. You have a really interesting story. So right now, you and your husband actually are kind of sitting on top of this empire, sort of popular culture empire. And I want to get into that and the journey that got you there. I want to take a big step back though. You grew up in the Northeast. Yes. Washington area? Yes. Right outside DC. Yeah. So in the 80s-ish then.

Yes. All right. So. Best time ever. Right. Take. And I'm a little bit older than you. That time, like where you were in the 80s, tell me a little bit about your youth.

I mean, what was it like? I loved the 80s. And, you know, outside, I got to walk to school from when I was a kindergartner. Everything was, you know, safe, I got to walk to school from when I was a kindergartner, everything was, you know, safe and suburban, but I was close enough to a city and, you know, all of sort of politics in DC, which is one of the reasons why I left. But I did, I loved it. I mean, you know, my brother and I played soccer and we went to summer camp and, you know, I would stay outside and play capture the flag with all the boys in the neighborhood until sunset. I haven't heard capture the flag for like, that was that was the summer thing it was like until

you had to come in yeah no that i mean we were outside all day until you know like mom came outside and said you know or it was sunset either you know mom was like dinner time or it was sunset you come running back into the house and all the kids in the neighborhood played and it was so innocent and amazing. I mean, I don't know if that time still exists, you know, there was definitely no computers and iPads and iPods. Yeah. Well, but so that's so interesting though, because you're, I mean, you're the mom of three girls, I guess. Do you try and recreate that at all in sort of the way, or do you think it's just like, it's a, it's a bygone era? I try to create it to a certain extent. Like I live in

San Francisco now, it's beautiful out. I feel compelled to get outside every day as much as we can you know get to a park ride a bike we have a dog that we need to walk yeah but my husband and i are also very you know into technology and we grew up especially him uh because he's a coder and he loves you know tinkering and he wants our girls to be very tech savvy so So we actually are having sort of that constant debate of our 10-year-old, is she old enough to have a phone or not yet? Because some of her friends have them. And his whole thing, and I did this with my brother a lot too, was we did play a lot of video games.

So even though we were outside a lot, once sort of Nintendo 64 and those, even Commodore. Everything changed. Yeah, we did play a lot of video games. And as long as it wasn't abused, we were allowed to do it. And, you know, I think there was that great balance of being outside so much and still being able to play video games. Now, I think it's a little bit more of right, because they follow you outside. Also, it's sort of like, you know, wherever you go, it's on you. I think that's the really big challenge. Yeah. And now, you know, they've

gone to the park and literally just asked for my phone for Pokemon Go. And I'm like, but there's like four of you. You can go kick a ball or something. And instead, they're just like, give me the phone. We want to go play Pokemon. So I'm fine with them experimenting and figuring out what they want to do as long as they come back to the books at some point or the crafts and the other things. And right now, there's still a nice balance and it's innocent and all that. So we'll see in the next couple of years what happens. Yeah, it's really interesting because it's the father of a 15-year-old girl now.

It's what surprised me and where I don't have an answer right now is that it happens really quickly is that it becomes a source of social connection too. And if you're not on your phone, if you're not sort of dialed into the conversation on Snapchat or whatever it is, you're sort of socially outcast.

Right. And I don't – that's the thing that I don't know how – I mean, it's easy to say, oh, put it down, go run around, go do arts and crafts. And I'm a total believer in all of that, like get dirty, work with your hands. But there's that social aspect of it, especially for kids that reach their teen years where you're literally – you're telling them, know, like, step out of your social circle when you actually tell them to put down technology. And that's a brutally hard thing to do. Yeah. I think the harder thing, too, is me just saying, like, put the iPad down. And then she's like, but I'm actually reading a book. Yeah, right.

Oh, now I feel bad. I just yelled at you. And you're reading, which is lovely. Yeah, right now for us snapchat is just playing with filters on my phone they're not quite like they don't have their own accounts on that yet um but there are you know and just texting so it's still it's still innocent i don't quite have to worry about uh the social but i know it's coming in the next couple years and yeah and i think you know in the way we were brought up it's just we don't know what the rules are now yeah we'll just make them as we go along yeah exactly it exactly. It's kind of like, you know what, we'll do our best.

And hope they end up okay. Then they will, they'll all end up fine. So you're growing up close to DC. And like you said, it's a town defined by politics. But clearly from your earlier comment, that was not your thing. No, definitely not. I mean, I think, you know, it's amazing what people are doing. And I'm extremely happy that we live in a country that, you know, we have the freedom and we're fortunate to be able to have wonderful people protecting us and all that. But when it came to what DC was about, I mean, I grew up, it was like lawyers, doctors and politicians. And I just knew that that wasn't where I wanted to stay. Yeah. I eventually came to New York. and that was the next city for me. And I got a lot more alive here. Yeah. What was the thing that made you come to New York? What was it about? Brian, my boyfriend in college, now husband, came here to start building J.Crew's

website back in the days before anyone even knew what websites were. So he was up here for a year, almost two years when I was still in college. And would come up here on the weekends i came up for the summer and i interned and then eventually just immediately so i graduated after i graduated i came up and moved in yeah yeah was there something in new york particularly that also drew you i mean i guess if you're because one of the things that you've you've sort of shared is that you've had this lifelong session with um pop culture yeah Take me back to like when, do you remember where that came out of, like when they first started?

Well, I think, well, I can tell some early stories was my dad actually had a case. He's a lawyer, he's still a lawyer, in LA for like 15 years. We used to joke that he had another family in Hollywood. Oh my God, 15 years? 15 years, he would go back and forth to LA for this case. And he took me in eighth grade once

with him. I was like old enough to kind of go. And when he worked, I could, and I just loved it so much. And, you know, we had traveled a lot as kids, but every time I'd go to Hollywood, I just, I loved it. So that was like an early sign. I was like, oh, maybe I'll come here for college. This is amazing. But then when it came time for college, I was like, that's actually really far away. I don't want to go that far. So I didn't really get a good taste of it until I did come to New York. So even though I loved pop culture and entertainment and reading and writing, I didn't think I could actually do that for a living. Like to me, I didn't actually know that there were jobs behind it. Obviously there were, but I didn't think that that was something I could do because I was so surrounded by, you know,

lawyers and doctors and politicians. So once I actually got to New York, I had an internship at Fox, actually. That was my sort of first foray into this world. And it was a live morning show with Tom Bergeron. It was so lovely. Right. And that was another, you know, big sign where I was just like, that's it. I need to somehow make it into this world. And the other one, which I talk about in the book, was Brian brought home a pilot for Dawson's Creek

right and J. Crew was dressing them and he said you got to watch this show it's the next 90210 and I was like totally let me see and I just having access to a show that no one had seen yet that the writing was so clever and the cast was adorable and the clothes were great I was just like I'm in I somehow have to be involved in this I don't know what this is but I need to figure out how to get in it. Yeah. It's amazing to sort of stumble upon something like that where you're just like, huh, I don't know what it is about it, but I'm fascinated. I'm drawn to it. Like I want to know more.

Yeah. And I think, you know, going back to Dawson's Creek, you know, you have James Van Der Beek character who in high school was obsessed with Spielberg, right? And he knew early on he wanted to create content. To me that that, that didn't clicked earlier. It's so funny that Brian also said it's the next 90210, which was for a lot of people. Our audience, probably everybody knows that. But for a young generation, they're like, 90 what? Yeah. Well, and the other funny thing about 90210 is Darren Starr actually grew up in my hometown.

And it was supposed to be called Potomac 20854, but no one knows what Potomac is. Right. So they changed it to Beverly Hills. That's the rumor. Oh, that's funny. Yeah. Yeah, it's amazing the way that we stumble into stuff like that. Yeah, I mean, it's almost like, you know, there's this thing that comes.

And also, this was like such a great time to sort of be involved. I mean, the 80s is when so much broke, you know, it's like, you know, big hair, crazy outfits. And it was, I kind of feel like that was when so much of pop culture just kind of really exploded onto the scene. And TV changed in a really big way. Darren Star, I think, was probably a big part of that. Yes. Yeah.

It became more fun. Yeah. Yeah. No, I definitely think it's true. So from there, you're kind of hanging out and trying to figure out your next move. But you weren't ready to really dive into this full time. No. And at the same time, you're kind of hanging out and trying to figure out your next move. But you weren't ready to really dive into this full time. No. And at the same time, you're married.

Married at like 22. I mean, I was really young. Right. You tell a story in the book. You met Brian. Was it your first week in college? My roommate went to high school with him. So we went to go meet this guy she went to high school with.

Just because, you know, that's what you do, right? When you start a new school and you're meeting new people it's like who you know already so emily introduced me to brian and love it for a side yeah uh you know i had a boyfriend he had a girlfriend but i played him in fifa soccer and beat him so you know my my video game skills helped me out because i had that older brother and i completely hushed him like on the first no i think that's how i got noticed you know it's, this girl can play. She's got skills. That's too funny.

So you hang out in the industry. And you're living in New York for a chunk of years at that point. Yeah, for me, it was just a couple years. Brian was up here for like five. And so for us, for me, it was just a couple. Yeah. But you followed this path into the media world. Yeah.

So from the morning show, you didn't stay there for that long. No, I was just an intern there. So that was just for the summer. And then when I graduated, I was really eager to get into entertainment. And everyone was just shooting me down. They're like, forget it. You need to be somebody's little sister or daughter to get in. And I went through a bunch of interviews.

And I was making my way into some great places, but then I decided, you know what? I'm going to look at advertising. This seems like an interesting way to get into New York at the time. Also sort of like, yeah. Yeah.

So I, I took a job at young and Rubicon, which to me was like quintessential Madison Avenue agency. And my accounts were Showtime and Sony. So I was like, I'm close enough to entertainment with these types of accounts. And it was a great, great first experience. What were you actually doing there?

I was doing media planning. So I basically would be given a budget and we would figure out where to spend the money to reach the target that they wanted to reach to tell you, you know, so Showtime did a lot of original movies at the time. And, you know, every time we would figure out that movie, you know, who the target was and we'd buy pages and people magazine and entertainment weekly and this again was all before digital we'd buy outdoor advertising radio so what do you i mean is this fun for you because it's really interesting to me because there's i've had a number of conversations with people where it's like you kind of have a sense for this thing that you like and then but you like you're not at a point where you can kind of step directly into

like that like the center of that thing so you you start to work on the fringes or as part of the culture yeah and sometimes it really satisfies that jones but sometimes it completely doesn't sometimes it actually even makes it worse i i really enjoyed it. I was on a team with four women who were like really encouraging and really fun. And I had an amazing client at Showtime who I loved, who was just such a pleasure to work with. I mean, it was really too good to be true.

I mean, sure, there was parts that sucked, working really late, you know, lots of tight turnarounds. But it taught me a lot about what a first job is all about. And like, you have to work late. And, you know, being a client-based business, you're on the beck and call of somebody else.

So if they call it six at night and they need something turned around by the next day, like you're there. So it actually taught me a lot. And, you know, at the end of the day, I liked, I liked the people. It was a fun culture. There were a lot of people starting out at the same time. So you felt comfortable asking questions. Like it wasn't like you were the only newbie there. There were new people starting all the time.

Right. Do you think that that, that that has changed in terms of, um, there's sort of like an, an expectation of not having to work that fiercely or deliver that level of service and sort of much faster progression along the path. When I started,.com had just started also. So people were leaving the jobs after like six months and going and getting a promotion and $5,000 more like overnight. And I think it was scary for the agencies because they were like, wait, we just found these people. We just trained them.

So I see a sense of that today because there is a lot of, you know, folks that when they do learn something and they're quick and they're good at it, they know that they could try to take that somewhere else. But I do think that if ultimately you find the right place or you're happy, then they will stay and want to continue to grow up and progress where they are. I mean, that's definitely what we want at PopSugar because, you know, we have a lot of really great young people. We work fast. We work around the clock. And if they're into it, and, you know, hopefully by the time we're obviously interviewing, we know that they're going to be into it. It's a nice fit and it's a good marriage. And these folks are with us for a long time, which is awesome.

Yeah. How much of that do you think comes from the top down, sort of like the culture that's created and the expectations, you like about what goes in a lot yeah i mean i i think brian and i work really hard to make sure that we've created a fun company i mean people are spending more time with us than they are with their families we want them to love where they come every day um so we definitely want to make it a place where you know we had just as much fun building this company starting 10 years ago with you know just a really small group of us. And a lot of them were friends when we started. So now we're 500 people.

And my biggest problem is that I don't know everyone. I really wish I knew everyone. It makes me upset that I don't. Does that freak you out ever? I mean, it doesn't freak me out. It just makes me sad because I really want to know everyone. These folks are just as dedicated, hopefully, to PopSugar as I am. And I want to be able to know everyone's name. And I just, I don't yet. But it's such an amazing experience to be able to build a company and then have all these people on your team with

you, you know, cheering for the same goals. So that's awesome. It is amazing. It's funny. Years ago, I owned a yoga center in New York City, and we were growing really nicely. And it's so weird to this day. I remember the day that I walked in the front door and I sort of like, you know, like past the front desk and the person behind the desk said, Oh, are you here for class? And I'm like, Oh my God. You know? And on the one hand, I'm freaked out because I'm like, they don't know who the founder is. But on the other hand, I'm like, but you know, we're growing, you know, and where there's a certain ethos and, you know, somebody actually said something. Hey, which is great.

They were, you know, like well-trained and they wanted to be service minded. But yeah, it is really interesting when you hit that just tipping point. You're like, huh, there's, it's bigger than me. And it's both amazing and a little bit scary. Yeah. The Apple Watch Series 10 is here. It has the biggest display ever. amazing and a little bit scary. Yeah. you eight hours of charge in just 15 minutes. The Apple Watch Series 10. Available for the first time in glossy jet black aluminum. Compared to previous generations, iPhone XS or later required. Charge time and

actual results will vary. Mayday, mayday. We've been compromised. The pilot's a hitman. I knew you were gonna be fun. January 24th. Tell me how to fly this thing. Mark Wahlberg. You know what the difference between me and you is? You're going to die.

Don't shoot him. We need him. Y'all need a pilot. Flight risk. Yeah. So let's kind of fill in the gaps a little bit here because we kind of jumped right into PopSugar and I want to come back there. So you spent a chunk of time in New York, right?

Working in YNR. Yeah. So I worked at YNR and I was actually only there for a year. And then my wonderful client at Showtime actually hired me over to Showtime. So I was like, sweet, this is amazing. I now get to go to the client side, which is another part of the experience, a new way to learn. Right. And I'm now on the other side, getting to see, you know, from the Showtime perspective, what we need from the agency and, you know, how to work on the other angle. And I really loved my boss and he was super encouraging. He's still there,

George, he's amazing. And, you know, he would set me up to present to EVPs when I was, you know, 23. So he really wanted to give me an opportunity to to grow and then he also knew deep down he knew that i did want to get into more of the entertainment side and i was still doing the same job technically i was still media planning but now on the client side so he knew he's like look you know let's do this for a little while and then you're in the family now like we'll find right yeah and i loved that i loved that being in my mind like be here for a little bit in this position you're doing great at it grow here learn here and then we'll see where it goes what an amazing also moment because he was playing the role not just of your boss but of your mentor like he was actually looking out for your personal growth

and not just sort of like how do i feel in need of company that doesn't happen a lot i mean maybe i'm wrong but it doesn't feel like that happens the way it sort of used to a generation ago almost. Yeah, no, he was extremely encouraging. And that was another great thing for me to take away as we start a company and have our company culture. So, you know, who lifted me up along the way? Like George absolutely believed in me, knew that this wasn't what I wanted to do forever, but said, take this opportunity now and know that we'll figure something out when the time comes. And just knowing that in my head was already encouraging. So. Yeah. I mean, what an amazing thing for you to see also. I mean, when you were in, I mean,

reflecting on it, you can be like, oh, wow, that was really cool. When you were in the moment, were you aware of sort of like the unusual nature of sort of like his, his mentoring lens? I definitely knew he was special. You know, I definitely knew that, you know, this was, there are a lot of people who had horrible bosses. And at this point, yes, a lot of my friends were all starting out there. I've got friends quitting jobs left and right because they've been like verbally abused or, you know, hit on or other horrible things where I'm just like, oh my God, I'm in this really great place that I've not had to deal with any of that kind of stuff.

Yeah. Well, especially also, I mean, in, in media and in advertising, it's in New York city when you're in that sort of startup and it's not known as a friendly industry. Yeah, no, it is. It definitely, when I first started, I would say there was that sort of corporate, because wine are so big, um, that corporate culture where people were climbing ladders and such, but I didn't, I just, maybe I was lucky because my team didn't feel that way. And then when I got to Showtime, it didn't, it just didn't feel corporate besides being

in that huge building. So what, what, what made you leave? We moved to San Francisco. Yeah. So it really was just that Brian got an amazing job opportunity. We'd just gotten married. We're like, let's go anywhere and just start over. Like just the two of us were so in love and uh we moved across the country to san

francisco it was 99.com crazy people were throwing money in every which way and brian got an amazing opportunity to uh launch kmart which was kmart martha stewart yahoo and they did this thing called bluelight.com like the Kmart special. Right. Yeah, of course. So, so we went out there and then I was totally crushed because I was like, I'm getting so close to, you know. Right.

It's like, you're starting to work your way. Yeah. I was like, oh, I'm at Showtime. Like I'm so close to MTV. Right. That's like, that was like, how do I get next door? Because that was the bastion, especially at that time. Right.

Yeah. I'm like, how do I just get down the street to MTV? But I moved to San Francisco and then I was like, forget it. What am I going to do there? I don't want to do anything local because I'm only going to be here for like three to five years. And I don't want to do technology. And it's not LA or New York. So there's...

No. Yeah. So I did try to interview at some magazines. Like there were some home design stuff and, you know, nobody would hire me. I had no experience um and yet every agency was throwing ridiculous like offers out to me because i had new york yeah i had great experience both client and agency side new york trained like so i did find an amazing place in san francisco like again so i did this sort of quintessential madison avenue agency when i went to san franc, I did this sort of quintessential creative shop, which was

Goodby Silver Sina Partners. And I was there for over five years. And another really amazing, great place where you have, you know, Jeff and Rich in the office every day and creating a company culture where they're very transparent and they address, you know, the ups and downs of what's happening. And they were in a really great growth time as well. So there were new people starting all the time. And there were a lot of similarities that I had from YNR days.

And I figured, you know what? I still had a lot to learn in advertising. So I had to work. I wasn't going to just be like, I had to work. So I knew I wasn't going to be creating content quite yet. The timing was not there. And yeah, there was no opportunities for me. Was the seed planted in your head, though, by then that you wanted to be creating content because i'm like especially in that time even the word

content was kind of really not not even on the radar i know it's funny a lot of people say to me why do you even say that that's like not a you know word that people use but it really i mean that's how we talk about it every day well there was definitely no blogs or anything at that point like online yeah started like mid 2000 like four or five ish right yeah so it wasn't i i was looking at jobs like magazines local tv even agents i was like oh you know there's a lot of agents there's a lot of ad agencies maybe i could go be an agent or something and help like cast for. Like it just something that was related to creating video if it was or print. Um,

but it was really limited in San Francisco and the opportunities were not there for me. So, so you end up at Goodby, um, which also is, you know, has,

has this longstanding reputation for being different. Yeah. It's great still. Yeah. And for about five years? Yes. And you start to get the bug. Yeah, I just, you know, even after a couple years, as much as I loved the people I was starting to meet, I just wasn't being able to be creative in a way that I felt like I

was enjoying myself, because here I was still looking at spreadsheets and Excel charts and dealing with budgets. I mean, a lot of budgets and numbers. And at this point, I did have some really great clients, really great clients. But Sony and Showtime really were, especially Showtime, like I really felt like I was at least still attached to entertainment in some way, shape, or form. And I wasn't on those types of accounts. So it just wasn't as exciting for me. So what's the, what's the thing that makes you say, huh, it's time. Yeah. So I, um, this sounds like everything's actually pretty good. Yeah. I mean, I definitely had some not great clients or bosses like over the years where I was just like, why am I doing this? I don't even

enjoy at the end of the day, what I'm doing on a day-to-day basis. So I, there were definitely times where I'm like, how much longer am I going to do this? And, and this is now, you know, you know, 25, 26, 27. And I'm sitting here like I should, every year I'm reevaluating, why am I still doing this? And eventually I'm like, I, I know I don't want to do this in my thirties. So like, when am I going to stop? And I just kind of didn't. So I actually had Brian, blogs were starting and Brian was helping some friends out, whether it's from a design perspective or setting up a site, building sites,

because he loves building. He's an engineer. Those video games paid off. And a good friend, Oum Malik, who was a tech writer it's like i'm gonna start this you know this site gig ohm and um and he was just over the house and he would listen to me talk about you know just stuff that i thought was useless information you know about this celebrity that celebrity this show you know all this stuff and he's like you gotta just start writing because he knew he knew that i wanted to write and i was so excited about what he was doing. And he's like, you know, just start.

And he really, he kind of just put it in my head, like, you're right, I need to just do it. So Brian built PopSugar for me and taught me some code and I set really small goals. I was still working at Goodby, so it was a matter of like writing something in the morning, you know, writing something at lunch, writing something when I came home.

And I was bored with, when I was at at Goodby on all my breaks that I could. I would go to all the sites that did exist at the time or the magazines, and none of them really spoke to me or they didn't update enough. I felt like I could add something to what was missing out there. So you just started really doing this in the margins. It's sort of like a little bit like any moment you could get. Any moment I could, and I became so addicted to doing it because the beauty of online is I could see immediately

what people were reacting to and how many people were coming to the site and people were commenting and this community was building so fast. This was well before social media. So, I mean, all of a sudden people were becoming friends in the comment section and they would talk about what they were doing this weekend. And, you know, it's just so cool to see.

Did it take you by surprise? Definitely. Cause I, well, when I first, first started, I didn't even tell anyone besides Brian and, and like, nobody knew I was doing this. Cause I was like, The secret project. Yeah. I was like, I don't know what my voice is yet. Let me get myself, you know, even in the pattern of doing this. And my friends, I was like, I don't know what my voice is yet. Let me get myself, you know, even in the pattern of doing this. And my friends, I was like, they're not even going to understand it because, you know, blogs like just weren't a thing. So I kind of kept it to myself.

And then I, it started growing and I started telling some friends and they were like, it's, you know, it's really good. And they were encouraging me, which is great. So along with this audience of people I didn't know in real life who were starting to leave comments, my friends and, you know, I actually had a handful that were in PR and they immediately were just like telling everyone and because that's by nature what they do. Right. And they were so great at spreading the word about pop sugar pretty early on. So then like a lot of movie studios and networks did see it and get access to it. And then I would start getting invited to, to movies before they were out so i could review them and so i i got to do that a lot and you know i had some actually really fun experiences early on where i did get to

like inner i did um brokeback mountain was one of the first movie reviews i did and king kong and i got to go see king kong in um george lucas's presidio theater nice i mean it was just like magical right it's like taking that early service c CD of Dawson's Creek and just amplifying it. Yeah, exactly. 10,000 times. It's like, wow, now I'm in George's private theater. I mean, most people did not like that movie. You read my review.

I loved it. It had nothing to do with the whole experience. I mean, it was all, it was the whole experience. I mean, it was, it really was. So you got, you were like in. Yeah. And then I was like, how many movies can I review? How many? He like, you know, it really was like, so you got, you were like in, yeah. And then it was like, how many movies can I review? How many, like, you know, and then one thing just kept leading to another. And at what point do you say to yourself,

cause this is a fascination of mine. You know, when you have somebody who's a grownup, she got a family and you've got the job. Um, but you know that this thing is growing on the side and you know that this is the thing that's really lighting you up. I'm always curious, like, at what point do you make the decision to say, okay, it's time, like, I see where this is going. There's a trajectory forming, but I got to give it everything and step away from that main thing. Yeah. So I started writing in March of 05. And by November, I actually left Goodby because it was starting to get really fast and really big. And Brian, um, you know, he really had the foresight to say like, this is, this is awesome. Go all in

and let's build this audience as fast as you can. I mean, it was a hockey stick. Like it was just exploding. And, um, he saw how happy I was from it. And at the same time, we did just find out that I was pregnant. So that was fun. So I really just, you know, he was like, let's just do it. Like, you know, go all in. So even though I was, you know, literally like a month pregnant, I left Goodby at the time. And I went all in for PopSugar. And then six months later, he left his job and came and joined me. And we had an idea, you know, we knew knew let's go beyond celebrity and pop culture i was writing about a bag here and a couple beauty products here that i love like i wanted other things i always envisioned i would write other stuff but um it didn't work in that blog format all in one stream because people were like so excited about all the celebrity content and then there was like a purse that i wanted and they were like was distracting. So we knew we wanted to roll out. And I immediately knew that

because I wanted to talk to women in their 20s, that advice was the next. Because I know that all day long, I'm on the phone with my girlfriends, giving each other advice. So we knew we wanted to have, it was at one point, Dear Sugar, Ask Sugar, but a QA just of anything.

And so, you know, one of my girlfriends from college came on board, didn't have any money to pay her. She's like, I'm going to do this with you. And you know, and that's how it started. It's like, you believe in the mission and you, and then you, yeah. And she had a blast with it and ended up staying on board with us, you know, once we got funded and, you know, for over five years and yeah. Well well how do you figure out what the voice is because that's when you're starting something like that it's that's not i mean that was actually that was actually the easiest part really it was so natural i mean it really was just what my thoughts were and and i think what was really important to me was that it

was different that was out there so everything that was out there at the time was very matter of fact, either like magazine, who, what, where, when, why, done. Or mean and like super snarky or really nasty. So to me, it was a no brainer. Like I love celebrities. They're traveling the world and they're entertaining me nonstop. Like what's, I want to thank them for that. And like, I was just so happy to be able to know more about where everybody was at any given time, because I was starting to, you know, find access to where people were before, again, before social media, you know, I knew where they were eating dinner on a Friday and Saturday night and, you know, but even just seeing, you know, all the news coming in about stuff. And I used to describe it as a puzzle where you'd see the news every day. And then you'd see all these

at the time it was paparazzi pictures, which now are not nearly as important as they were 10 years ago but i would put the story to the picture because i didn't want to just put pictures up because you know that was obviously just really intrusive but sometimes that works um and that's what the audience wanted but most of the time i would try to pair it with a story so whether it was like somebody signing on for a new movie or like ratings from a show that just premiered the night before or somebody announcing a pregnancy or something so at least there was like context to it but the whole voice was very conversational very much your friend who's like in the know but not a know-it-all like i'm just super excited to share this with you because that's that's what i wanted to do i

wanted to share whatever it was that i learned and very fan friendly i always always wanted it to be very friendly for talent and celebrities because i knew as this was going to grow i wanted to be able to have access to interview them i envisioned that if we kept this a great place that was friendly we would work just the same way a people magazine works with talent like that that's what i was kind of envisioning us with a little more personality yeah i mean it's so interesting that the voice side came so easily. And I wonder if sometimes, I mean, obviously it's just an expression of the voice and like in the fun and the energy and the, I don't want to say it's not, well, it's respect, but also just kind of like almost like awe of what sort of like a lot of it is happening

around. Yeah. It's interesting to me because so many times when people, you know, say we're going to start a media company, there's all this process around what should our voice be? And like, there's, you know, analysis and data and market research. And which is great if you're maybe doing print and it costs a lot of money to publish something and then put on a new stamp. But I mean, online, you just test and see what the focus group comes back with. And that's the beauty of online and our company to everybody's always like what's your biggest failure and i'm like you know

we test new shit every day and if something fails like we learn from that really quickly and we just adapt so there hasn't been some huge disastrous thing because every day we're trying something new yeah i think it's it's so interesting because it's a it's a mindset that if you come out of traditional media or even traditional entrepreneurship, people don't get because like, you know, first you build it in a vacuum. Don't tell anyone what you're doing. And then like you put it out there land because you've got data from that. Rather than putting massive amounts of energy and money into something and then being crushed when it doesn't work. And it is kind of fun to see that shift in mindset both in the world of entrepreneurship and in media now. Although I think entrepreneurship has adopted that a lot more. Media, I still think there's a real struggle. I think it's because it depends on which media and what their revenue stream is.

If you're still based on subscriptions and newsstand sales, it's very different. Yeah, and it's harder. And there are bigger risks that you're taking because it costs real money to publish one big episode and hundreds of thousands of copies of it. Yeah, it's an interesting time to be in this space for sure. The Apple Watch Series 10 is here. It has the biggest display ever. It's also the thinnest Apple Watch ever, making it even more comfortable on your wrist,

whether you're running, swimming, or sleeping. And it's the fastest-charging Apple Watch, getting you eight hours of charge in just 15 minutes. The Apple Watch Series series 10 available for the first time in glossy jet black aluminum compared to previous generations iphone 10s are later required charge time and actual results will vary mayday mayday we've been compromised the pilot's a hitman i knew you were gonna be fun on january 24th tell me how to fly this thing mark walberg you know what the difference

between me and you is you're gonna die don't shoot if we need them y'all need a pilot flight risk you at some point you take funding what was tell me about that the decision making process there like yeah so we had about um i don't know there were like eight of us. And well, the funny story is, so my girlfriend I was telling you about that came on board without being paid. I also worked so fast that the first thing I wanted to do was hire a copywriter because I'm like, not a grammar geek. And I spell stuff wrong constantly. And I was like, I need somebody to look at my spelling. So copywriter was one of our first hires. And then, you know, we had, we had engineers and we hired one of our other, you know, best friends who's one of our founders and she was in finance and she came in

to be our managing editor, but we didn't know what the job was going to be. And she literally ended up doing, you know, everything from operations to hiring and training and everything. So anyways, we're having our first day and And this best friend, founder, who I mentioned, and the other best friend from college who's now writing, and I go to the Madonna concert. And I'm two weeks from giving birth to our first daughter. And we go to this concert and everybody comes to the house the next day for like first official day of training. And there's like six of us, seven of us.

And I end up going into labor. So we have to already like start, know taking a step back but i go and i have katie and um everybody's still at the house doing stuff while brian and i are at the hospital and we realized okay you know we should start getting some office space and at that point we had met a really amazing young woman who was going to help me start writing pop sugar because i I knew I was about to have this baby. I need somebody else to help me write. And we found some office space mid July. And at that point we were like, okay, like we know we want to roll out these other site ideas. What is this going to look like? And how many people are we going to want to hire? And we very quickly recorded by three amazing VCs in the area. And, um, and at first Brian didn't

want to take money. Brian was like, let's just kind of try to use some of our own from a company he had sold and keep the team really small and just go all in and work. Especially if you're growing explosively yourself. Right. It's not an easy decision. But we found these amazing, amazing investors who have been with us. So they ended up investing in September. And we took in 5 million

and we started to just hire and train for each vertical that we knew we wanted. And the goal was to get six up by the end of the year, six more. Which is massively aggressive. Aggressive. And was awesome. And we did, we got a handful of sites up and running by the end of the year. And, and you know into the end everything was just i mean it was moving so fast and it was so much fun and we were just concentrating on building the audience we weren't even thinking about you know building a sales team yet or any of that stuff it was just like keep the product awesome keep the site fast easy to read beautiful to look at and let's get the content up and let's hire this team. And so we did,

we hired, you know, a bunch of people. I think we were probably like maybe 30, 35 by the end of the year. And we were just off to the races. I mean, really, we were just having so much fun. And, you know, over the years we've taken in additional investment from, from, uh, mostly the same folks, but, you know, we haven't taken in money in over five years, uh, unlike our competitors who are just constantly taking in money. And we've been a profitable company for, you know, I think going on five years, which is like really awesome for 500 employees and being a global company. And, uh, you know, but we will have, we have an amazing team bringing in and we bought, um, I haven't mentioned this yet, but we bought a company called shop style. So shops that we bought in, uh, 2007 bought, um, I haven't mentioned this yet, but we bought a company called shop style.

Right. So shops that we bought in, uh, 2007 and, um, it was, it's basically kind of like a Google for fashion. So if you're looking for a black button down blouse, you type that in and it gives me,

you know, shirts from J crew, Nordstrom's, Neiman's, Saks, Net-A-Porter, forever 21. And,

uh, that became great for us because Brian has a commerce background. And his vision was, I don't want to just be an ad-based business. And because he saw that early on. Yeah, I was curious what the decision-making was behind that. Yeah, he knew, like, you know, publishing and media, you know, if you're only. You never know. Right.

And if you are dependent on just the ad industry dollars, that's scary for a media business. A lot of businesses learned that in 2008, 2009. Yes. And actually, because we had ShopSound, it now has over 1,400 retailers. We work with all these retailers, and we send them so much traffic every day that we have amazing partnerships with them. And we work really closely with them. And, you know, we work really closely with them too, because they love our business. So it's, it's this mutual relationship. That's amazing. That has, has helped the overall company at certain times. So sometimes

the media business is doing better. Sometimes the shop sell business is doing better and it's great for us because, you know, we're able to invest in different parts of the company at different times. And yeah, it's been really, it's been awesome. I love that because you're really, it's like you're taking this super rapid growth tech-based company, but you're also, you're diversifying the way that it generates money in a way where it's almost like you're creating verticals that are sort of like

revenue hedges based on assuming that things are going to shift. Yeah. And you don't want the rug to get pulled out from under you. Yeah. And I really think that's like the smartest thing we ever did as a company. And, you know, Brian saw it and, and we knew, you know, commerce and content, we always say there's like, there is

a marriage between that. I mean, even when you're reading a magazine, the whole point of it is to like be inspired to buy a product, but there's such barriers to actually find that product when you're looking at it in paper. Right. But online, it's so easy. You just click, you just click and go and buy, you know? So he actually, you know, loved that our editors were using ShopSell as a tool. And then we created tools to make it really easy for us to put that on the pages of articles that had shopping and product. Right. Was that the thing that really convinced you is that your own people were actually using this as a resource for themselves? Yes. Yeah. Which is always, I think, really important. It's like we use the product ourselves.

Right. Yeah. No, it's great. It's an amazing product. Yeah. So you're building this company and you're doing it with your husband too. And I'm always interested in this because I work with my wife. We run our company.

Was there a moment where you both said, okay, we're working together, we're doing this? Or did it just kind of happen? Because sometimes there are these negotiations when I've talked to people, and sometimes it's like, I have this skill set, you have that skill set, and you just kind of start helping each other do stuff. It's really the latter. I mean, we definitely are interested in a lot of the same things and different things. You know, I got asked yesterday what my favorite font is, and I'm just like, I could tell you the names of three fonts that that is not my expertise. Brian is an amazing eye and designer and he can talk fonts all day. And I love that about him. You know, I want to think about the stories and what's going to

resonate with our audience. And, you know, he's not as into necessarily that. And so, you know, we definitely balance each other out. But I mean, it brings up another question of mine, which is when you have two people who are partners, both in business and life, that it's been my experience. I'm curious whether you have this struggle at all. And with partners who I've talked to also that, especially when it's a business that you're both passionate about, you're both really, really dig, that it can sometimes be hard to find the off switch for that. And sort of like, okay, can we not talk about business anymore? I talk a lot about work-life blending. You know, we drop our girls off at school together. We walk into the office. Some days we don't talk. Some days we're talking business. Some days we're

talking family. Like some days we're brainstorming new things that we want to build. It really, every day is different. And, uh, you know know there's definitely times where if i had something super stressful and i come home and he wants to talk about i'll be like i'm done i'm off like we're gonna go watch change your things you know like um just awesome show by the way um but there's definitely times where we'll be like i can't i can't do this right now and then there are other times where it's like all right let's figure this out and really get through it but for the most part you know people have asked me that do you shut off when you're at home and it's no our kids see it all they see because you

i mean when you're an entrepreneur it's i think it's about you can't shut yeah and that's why it's funny when i read that using the word blend also because it's something i heard for the first time a couple years back from a friend of mine mitch joel who runs this digital agency and i was like it makes so much sense because to me people use the phrase work-life balance all the time. I'm like, there's an underlying assumption there, which is that life is good, work is bad. So you have to balance them against each other. And it's like, I just don't agree with that underlying assumption. Yeah.

I also, I basically say forget balance. Yeah, I totally agree with that. I mean, it's, you also just, it's, I don't know, life would be boring if it was so balanced. And I can understand people wanting, you know, things to not be so out of whack all the time. But I think that that's how you grow and learn how to push yourself. I totally agree. I mean, to me, it's like there's this, because I've heard this, you know, people like you aspire to this. There's like a point or there's sort of like a state of being called balance. I'm like, well, that sounds mythical. That's when you take the yoga class.

Right. It's like your life is a pendulum and your goal is just to get it to just be straight in the middle and never move. It's like, that's just not reality. Reality is it's swinging all day long in every direction. Your job is probably to have enough mechanisms to figure out when it's swinging out to the extreme and it needs to come back. But it's in motion. It just is. I've said from a work-life balance, I've learned to say no, or I know when I need to ask for help. But to me, to your point, it's almost like finding those times during the day or the week when you do just need that time where you need to get balanced. And for me, that's like, I'm more of like a soul cycle person. I know people love yoga. I have friends who meditate and it's sometimes it's just finding that five minutes

in the day to balance yourself versus like trying to have an overall work life balance. I think that's just like, not realistic. Yeah. I'm a big believer in daily practices, you know, and just sort of like having a daily practice that even if it's just a couple of minutes in the morning or in the evening or whatever it is, that kind of is a place where you can keep going back and just touching stone for a moment. So as we're hanging out here, the thing that brought you to New York is you got a book out. Yes.

So, which makes me really curious because you're going from big, like cutting edge media, completely digital to old form media to like published, printed, like hold it in your hands book. What was behind this decision? So I was really excited to write the book because we kept getting asked, I keep getting asked the same question. And it's basically like, how did you do this? And how do I get a job like yours? And, you know, in my 20s, I was trying to figure out how to get jobs in entertainment or creating content of some sort. And at the same time, a lot of people don't know the story of PopSugar. So I wanted to, you know, give that personal, you know, story and show bits and pieces

of how we built what we did, which we're really proud of, and I'm really excited about as well as a lot of practical advice. And I think that, you know, anybody who's trying to figure out what it is, whether you're, I say 16, 26, 46, you know, there's people who are, I have friends who are still trying to figure it out. And that's fine. You know, I think it's trying to help you find clues along the way that would make you happy. It's not just career. It's more of, you know, even just maybe finding that time to balance every day or a hobby that you want to fit more of in your life. So it's not all about making like some drastic career change. And I think, you know, I just was really excited.

I feel wiser now that we've been doing this and we've been able to build something, you know, that I'm just really proud and is successful. Did you, I'm curious what the experience was like for you because I'm an author also. So I'm always curious how people experience. And I've written what would be considered long form online, but like short form compared to a book for years and years. How did you find the difference between sort of like writing regularly or editing now because you're not doing as much of the writing versus saying, okay, I need to actually create a full length thing?

Yeah, no, this was definitely a way different process. For the book, I did a huge outline, which is really how we pitched to the publishers and just to give them a really good sense. And it was that combination of knowing some personal stories that I could share of how I would let them envision what was going to come to life, as well as things that we know. I mean, we just know our audience wants this career advice. So things that we've known along the way that we think would translate well in a book versus online, because there are, I mean, a lot of people are like, why is this different than anything I'd read on the site? And, you know, we'd create, you know, some checklists and questions to ask yourself in each chapter and, you know, really things that will help guide you. And I think that, you know, that's different than how we would have done that online. And when we think about writing a story online, it's so much more about, you know, having it be direct and short and, you know, as well as a really amazing headline and how am I going to catch you on social when you're taking a break in your day? And this is long term.

So the book really is setting you up and building on each chapter versus just, you know, a quick snippet of like a bit or a piece of something that could be online and live online forever and be found tomorrow. Did you feel that the book, because I'm guessing, tell me if I'm totally wrong with this, because you, I mean, you had the capacity to produce long form like video and stuff like that. Yeah. I mean, it would have been really interesting either like series of doc style videos or something like that. Did you dance with that at all also? Or was it just immediate like this, this has to actually be a book like that's the form. To me, it was a book. Yeah.

Definitely a book. I mean, I think now that the book's out, it's like, oh could do this in video let's bring in like build stuff around other people's stories and yeah and other workshop stuff where i think we could easily come up with some amazing you know power your happy video series but to me the original was was written form yeah that's totally awesome so we've been jamming for a little while now and and i have a little bit of inside intel oh which is that your social wiring is actually similar to mine, that you're really good in a room with a small number of people who you're really good with, but also sort of more towards the introverted side of the spectrum. As you now have to be hanging out and shopping around and public and interviewed, how are you with that? Yeah. So, I mean, I don't consider myself an introvert, but I'm married to an extreme extrovert. So by default, I've become more introverted.

Comparatively. Yes. But I do. I hate public speaking. I hate getting up in front of people. I love parties and I love being around people, but I don't like being the center of attention. I mean, for me, PopSugar was always about the audience and being able to create great content for them. It was never about me. And I didn't even care about having my own byline. Like I wanted it to be written by PopSugar. I didn't want it to actually be associated to me. But I love that I'm pushing myself out.

You know, I'm definitely making the scales unbalanced by forcing myself to do something new and just like with writing the site people are encouraging me to continue to do it and apparently i'm doing a good job so i'm trying to continue to keep it up and go at it and maybe i'll have a new skill set at the end of this but i do i i like being in the office and working with the team on a day-to-day basis so while this is great for me now and i'm gonna push myself and get out there and do this stuff i'm just just as excited to, you know, get back to the routine of, you know, the awesome brainstorming meetings I'm going to be having, you know, when I get back and thinking about award season around the corner and, you know, holiday and our live gift guide show that we do every year, which gets me really excited. So, but it's been an amazing experience and I'm

really thankful that I'm pushing myself to try new things and get in front of people, even if it's not something that I liked doing for the past 10 years. Yeah, I mean, I'm always curious how people sort of like navigate that. What are you really interested in right now? What's fascinating? What's like seriously calling you that nobody's asked you about? That's a good question. I'm very interested in how media, the landscape in general is changing. I mean, when I do think of like, I threw out the show Stranger Things,

and I think of, you know, how a Netflix or other companies are coming out there and creating content, and is that business model going to work well for them? You know, and what does that mean for us as we create video and have, you know want to create and where would they get distributed and all the partners and ways that we could work with people, whether it ends up maybe being on Snapchat one day versus a typical network or I don't know. I think that there's so many different ways that the world is constantly changing. But at the end of the day, I think it all still comes back to really great content. So as long as you have something really awesome that people are going to be into, it doesn't matter where they're consuming it. But I'm just really interested in seeing where and how the landscape is going to change. Yeah. So you're a bit of a futurist, it sounds like. Yeah. I mean,

I like thinking about the million places we can be consumed in the next 10 years, because it will be different. Oh, yeah. I mean, in the next, you know, 10 years. Because it will be different. Oh, yeah. I mean, in the next year, it's amazing how it feels like the rate of acceleration of change is just increasing every day. Let's come full circle. So the name of this is Good Life Project. So if I offer that term out to you, to live a good life, what does that mean to you? I think it is to, you know, be really passionate about what you're doing, to surround yourself

with people that lift you up and make you feel great. So, you know, in my case, that's obviously my family and the company that we've created and friends and trying new things. I mean, whether, you know, that means new companies or, you know, new projects or exploring and traveling and, you know, creating new traditions. That would be the good life. Thank you. Yeah. Thank you.

Hey, thanks so much for listening. We love sharing real unscripted conversations and ideas that matter. And if you enjoy that too, and if you enjoy what we're up to, I'd be so grateful if you take just a few seconds and rate and review the podcast. It really helps us get the word out. You can actually do that now right from the podcast app on your phone. If you have an iPhone, you just click on the reviews tab and take a few seconds and jam over there. And if you haven't yet subscribed while you're there, then make sure you hit the subscribe button while you're at it. And then you'll be sure to never miss out on any of our incredible guests or conversations or riffs. And for those of you, our awesome community who are

on other platforms, any love that you might be able to offer sharing our message would just be so appreciated. Until next time, this is Jonathan Fields signing off for Good Life Project. The Apple Watch Series 10 is here. It has the biggest display ever. It's also the thinnest Apple Watch ever, making it even more comfortable on your wrist, whether you're running, swimming, or sleeping. And it's the fastest-charging Apple Watch, getting you 8 hours of charge in just 15 minutes.

The Apple Watch Series X. Available for the first time in glossy jet black aluminum. Compared to previous generations, iPhone Xs are later required. Charge time and actual results will vary. Mayday, mayday. We've been compromised. The pilot's a hitman. I knew you were gonna be fun. On January 24th. Tell me how compromised. The pilot's a hitman. I knew you were gonna be fun. January 24th.

Tell me how to fly this thing. Mark Wahlberg. You know what the difference between me and you is? You're gonna die. Don't shoot him, we need him! Y'all need a pilot?