Ep. 150: Design Milk Founder Jaime Derringer
Founder of Design Milk and Clever co-creator Jaime Derringer grew up in New Jersey. An only child until 8, she was fiercely independent with an artistic streak, drawing inspiration from her quirky Nana. During college, she fell in love with Japanese and Asian culture, which still influences the artwork she does today, ranging from digital art to painting to tufted art. After college, she worked in project management, having a natural skill for coordinating and love for new challenges. In 2006, she founded Design Milk, a website featuring all things art and design that she loved. Now, 15 years later, Design Milk has expanded into a Shop, wide-reaching social media presence, and a growing team. In 2019, Jaime sold Design Milk to AHALife, remaining involved as CCO. She is a vibrant leader, brilliant artist, and a wonderful mom, friend, and wife. Her years of following her own artistic streak have certainly paid off.
Read the episode transcript here.
Jaime Derringer: I started a blog, I called it Design Milk. It was a ridiculous name, it was super silly. And I just started writing about things that I liked that I was finding on the internet and that just happened to be a lot of art and design.
Amy Devers: Hi everyone, I’m Amy Devers and this is Clever. Today I’m talking to Clever co-founder Jaime Derringer. Seperately from Clever, you probably also know Jaime as the founder of Design Milk, her other venture. Design Milk is the modern design platform that Jaime founded in 2006 which quickly became the go-to site for unique modern interiors, home furnishings, art, and architecture. Design Milk not only highlights emerging talent but is also dedicated to making modern living effortless and accessible. In 2019, Jaime sold Design Milk and became Chief Creative Officer of the new organization which includes Design Milk Magazine and Shop, AHALife and Kaufmann Mercantile. Now celebrating their 15th year anniversary, it’s no surprise Design Milk remains one of the most popular design magazines given Jaime’s keen eye, love for design, and expertise on design trends. It is my pleasure to share this conversation with Jaime who in addition to being a media badass is also a talented artist, great mom, and dear friend. Here’s Jaime.
JD: I’m Jaime Derringer and I live and work in San Diego, California and I am Founder and Chief Creative Officer of Design Milk, Co-Founder and Producer of Clever podcast and I’m an artist. And I do all of those things because I love them all and I love to be creative and I love working with really cool people.
AD: Yes, really cool people, like me -
JD: Present company included! (Laughter)
AD: Okay, well, it’s no secret that I know you well, but I know there’s also still a lot more to find out. So let’s go all the way back to the beginning. Tell me about where you grew up, your family dynamic and what kinds of things fascinated that little brain in Jaime, well, it was probably a big brain in Jaime Derringer’s little skull.
JD: (Laughs) I grew up in Southern New Jersey and I spent a lot of my weekends and summers at the shore, super-stereotypical. I was really independent. I was an only child until I was eight and my brother was born, he had some disability issues and so I was on my own a lot. And so there was a lot of daydreaming and creativity and exploration. And I was super independent. I think that’s kind of where all of that started. But I also had a really goofy and kind of quirky grandma who used to take me to the art store and all kinds of other crazy places when I was younger.
AD: God bless kookie grandmas!
JD: Totally. I was exposed to a lot of, art and crafts and stuff like that. And I also had an artistic aunt, so she always had cool stuff around too, so I think those were some of the early exposures to creative people and different types of thinking.
AD: Did that also help you with your expression? Did you different ways for it to manifest in the world?
JD: It did, but I would say, I always struggled with my own identity and so even before teen angst, I was just kind of adopting things from different people and I think that’s what you kind of do, right, as a kid, you look at that and you’re like, oh, that’s cool, I’m gonna take a little bit from here, a little bit from there and kind of put it into your personality.
AD: Yeah.
JD: And so I did a lot of that and then when I was a teenager, obviously there were a lot of angsty phases. But I feel like the creativity was always there, but I kind of wasn’t sure who I was, so I had a hard time expressing my own personal creativity and I didn’t really do much of that until I was an adult.
AD: Ah, I see, so it was sort of just brewing in there.
JD: I didn’t know how to get it out and I knew, at least from my exposure, that being an artist wasn’t really a viable career. There was always just this starving artist persona and then I didn’t know that design really existed.
AD: Yes!
JD: So my whole exposure to anything creative was, that’s a hobby, but you have to get a J-O-B, right?
AD: Right, which is something that you and I continually fight the good fight against. That parental dissuasion against the creative arts (laughs).
JD: Totally!
AD: Okay, so you mentioned some angsty chapters in your adolescence, what kind of angst, how that did that play out and how were you forming the adult version of yourself?
JD: Oh gosh, this is the long psychological self-awareness stuff I’m going through now that I’m in my 40s (laughter), so I’m trying to unpack what happened? Why was I like that as a teenager? What does that mean? I’m going through a lot of that right now. So it’s all of that shaped me as an adult, but what I think I’m trying to figure out now is what parts of those things do I want to have in my life and how does that shape how I am today. And who am I really is the big question, always.
AD: Yeah and which wires do you need to uncross -
JD: Yeah.
AD: That’s the business of adulthood, right, is finishing the unfinished business of childhood. But like what did it look like when you were an actual teenager?
JD: I was a hot mess (laughs) because I didn’t know who I was and I went to a Catholic school until 8th grade, so I got into high school, this big public high school, there were so many kids and they had all come from public middle school and I was like -
AD: But wait, you’re not Catholic?
JD: My mom went to Catholic school too and my mom’s family has like a Catholic background, but we weren’t religion people. But I think it was something about she went to Catholic school, so I went to Catholic school. I don’t know if she thought it was like a better education or she didn’t like the public schools, I actually never asked her this question, so maybe one day I will. Yeah, she stuck me in Catholic school until 8th grade. So you know, pubescent Jaime, hits high school and it’s like what is this?
AD: Whoa!
JD: You know, this public high school and my brain explodes, you know? And it was around that time when I started listening to Nirvana and Hole and I was into The Cure and I started to just try to find myself, as you do as an angsty teen. And I went through tons of phases, I mean I was everything, Goth, raver, whatever, all of it. And I kind of feel like they are all me, which is something that I’m learning as I’m an adult that I can be all of the things and that’s okay.
AD: Yes, you don’t need to pick a specialty; you just need to be the complex cocktail that you are. With all the notes and flavors. Okay (laughs), so what did all of this hot messery lead you to in terms of going to college and thinking about your future? I know at some point in there you met Jordan, who turned out to be your lifelong partner -
JD: I guess for college I was into writing. I was trying to figure out how do I write for a living because I wanted to be a creative writer, but I knew that that probably wasn’t the first job you get out of the gate. I was editor of the literary magazine and then I was editor of my literary magazine in college and I majored in English and communications at Loyola and for fun, I like to challenge myself, I took a class in Japanese, just to learn the Japanese language because I thought it was interesting and it was completely different from all my other classes.
And I fell so much in love with it that I ended up transferring to Temple to be an Asian studies major with a focus on Japanese culture and language and a minor in East Asian arts, art history. So completely, like a total left turn. But that was after a couple of years of English and communication. So I kind of felt like I had gotten enough of that and I wanted to move onto something more interesting.
AD: Was this propelled by just your curiosity and your love for Japanese culture or was this propelled by a thought of what you might do with it and how you might change the world with your Asian studies education?
JD: I think part of it was, I don’t know what I want to do with my life. And the other part was, I am interested in this, I don’t know why I wanted to follow a passion. I did have a passion for writing, but I was not very confident in my writing. I still thought I wasn’t great and I also found myself to be better at coordinating things that are related to writing.
AD: You do have a magical gift for coordination (laughter).
JD: Yes, so I was like, okay, you know, let me just follow this thing and see what happens. And my parents were super cool; they pretty much always told me to do whatever I wanted to do. I was like, okay, I’m going to go and be this Asian studies/Japanese major and see where that takes me. I had absolutely no plan. And looking back I’m really proud of myself for being so bold in my choice, but also it was terrifying because I didn’t know what kind of job I was going to get.
AD: You were flying blind, but you were also just, I’m sure, really engaged because you were so fascinated and interested in what you were learning. You graduate from Temple and then what happens, and where is Jordan in all of this?
JD: Jordan had finished up his degree and when I graduated, so he was in law school. And I end up getting this job at a small publishing company in Southern New Jersey doing project management. And I was like, I don’t know what project management is, but there’s editing and writing involved and they have a publication that’s in Spanish and they have a publication that’s in Japanese and those were two of the other languages that I had studies.
So I was like cool, I might get to travel to these places, I might be able to brush up on my language skills while I’m there and it’s also publishing, which is related to English and communication. So I was like, this is the perfect job for me. Fast forward (laughs) maybe about a year, I’m like no, I can’t do this anymore.
AD: Why? What was that about?
JD: Well, first of all, I feel like the project management was perfect for me, but I just, Amy, I really struggle with working with other people and I’m super independent. And I think I was young and immature too and didn’t really understand how to work with other people. And I grew up feeling like an only child, I never really had to compromise with people or get along with people, even if I didn’t want to these are all also like 40 year old self-awareness, tons of work on myself kind of realisations.
AD: That’s what makes is so interesting.
JD: So at some point I’m like, I can’t work with people and I job hopped for a while. I just couldn’t find a job and then finally… That I liked. And finally I found a job where I felt like I had enough independence and I felt like people trusted my judgement and my decision making and all of that and it was so great. And I really loved it and then it kind of got a little stale and I don’t do well with that. I got to keep moving, I got to keep changing. So I was like messing around on the internet and discovered blogs and that’s kind of where my brain exploded again.
AD: Okay, foreshadowing, what year is this -
JD: 2006.
AD: Okay.
JD: So early internet, but not so early, but early enough. It’s still MySpace time and there’s websites like Delicious which was like a book marking website -
AD: Yes, I remember.
JD: So fun, yeah, and Live Journals kind of teetering off. Everybody is on My Space, everybody is launching blogs on Blogspot, which turned into Blogger. I was like, oh, this is really cool, I think I have something to say, but I’m not really sure what. But I’m just going to start a blog. So I started a blog, I called it Design Milk, it was a ridiculous name. It was super silly and I just started writing about things that I liked, that I was finding on the internet. And that just happened to be a lot of art and design.
AD: Okay, so (laughs) that’s how it all got started everyone (laughter).
JD: I wish it was a more glamorous story, but I was bored at work and I was like, I’m just going to launch this website.
AD: And so these are the things that you were just sort of interested in on the side anyway. You didn’t really get started thinking this was a side hustle, you just wanted a different area to express yourself, to keep your mind activated and your creativity going because you were feeling bored at work?
JD: Yeah, I think that was it, but not too long after starting it, I started to see the potential. And I was like, oh, maybe I could do more of this, this could potentially become something like a side hustle that makes a little bit of money here and there with Google ads or something like that. But Amy, you know me, I have a really hard time not turning anything into a hustle. It’s great but it’s also problematic but in this case it was great because I really worked super hard on Design Milk. I designed the whole site in the beginning. I learned about advertising online, I taught myself HTML and CSS and I did so much in the beginning because I was so excited about it. And that was such an exciting time online too. Because the community was really small as well, so everybody was commenting on each other’s websites and Google Reader was just starting to become a thing. Yeah, it was a fun time.
AD: So Design Milk is now 15 years in, so we need to walk through the major milestones. But there in the beginning, did you find, when you started noticing the potential, was that because your strategy brain kicked in or was that because you got some traction or was it a combination of both and how much do you think timing was played a role?
JD: Oh, timing was huge. I wasn’t launching something into a sea of blogs. This was a very early time, so I feel like being an early adopter was super important. So if I had launched this today, I don’t know where it would even exist, it probably wouldn’t even be a blog, it would just be like a social profile or a TikTok or something like that. (Laughter) But there’s already so many of those too, so it’s like I would have had to launch the TikTok two years ago.
I feel like timing was huge. There were less fish in the sea and I also feel like I have to credit myself for my hustle because I did work incredibly hard on it. But I also feel like at some point there was a shift in which I was like, this is fun and then someone emailed me about putting their banner ad on my website. And I was like, oh, cool, like I can make money from this, like it could really be a business. And then I started looking into blogs that were businesses.
AD: Ah!
JD: I started thinking about it like a magazine. That’s kind of where things shifted.
AD: And at what point was it just growing to be too much for Jaime Derringer alone and did you quit your day job first and before you actually had any team members or did you hire a team before you quit your day job?
JD: I did quit my day job before I hired a team. It was 2009 and I was just done and I credit my husband for being super supportive because I was like, hey dude (laughs) I’m gonna quit my job today, I’m gonna just try this Design Milk thing fulltime and see where it goes. And at that point it was making pretty decent money, so I feel like it wasn’t as much of a risk. But yeah, he was super supportive, he was like, “Go for it.” That’s when I quit my day job and about two years later I got pregnant and I was like, oh, I can’t do this by myself anymore (laughter).
So that’s when I hired a couple of people and that was the beginning. One of the first people I hired was Caroline Williamson who is our editorial director. She has been with the site for 10 years now and I know that because I hired her right before I had my daughter and my daughter is turning 10. Which is crazy to me too, that it’s been 15 years, it’s really mindblowing, but I’ve actually had a steady thing -
AD: Yeah, for somebody who went from trying all different things on, you stuck with this for a long time.
JD: Yeah, but the coolest thing about it is it’s always changed. Like everything is different. Every day is different, every week is different and that’s what keeps it fun. It’s never monotonous.
AD: The other thing is, like you’re working in, your content area is creativity and I mean creativity itself is like this never ending fountain of fascination and interest. So you’re in a good spot for it not to get boring. So you quit your day job, you started hiring people, what are the major milestones of Design Milk’s growth?
JD: The first one for me was quitting my job, but that’s a personal one. But I would say expanding the team, so hiring our first people. So when Caroline came on and that was 2011 - I don’t want to get too much into the weeds of being a new mom and being responsible for a human and running a website, but it was a lot in the very beginning, even having people help out or hiring people. Design Milk feels kind of like my other child in a weird way. And I never really stopped moving with it. I just kept on and the great thing about hiring people is I could step back and start thinking about the growth of the website versus the day-to-day management of it and that continued on as we hired more people. Tech editor, Gregory, we have Vy who was working on social media, she’s our lifestyle editor now. So having more and more people come on and help with the different parts of the business and help it grow has been super critical. And now it’s like 20 some people, which is blowing my mind!
AD: So at this point you’re a pretty blog, is Instagram around yet and -
JD: Yeah, I can’t remember when we started with most of the social media, but we were early adopters on most of the platforms. I wouldn’t say we were the first people, but we tried to sign up for everything as early as possible to get in. Yeah, so Instagram comes around, so we expanded our Instagram with Design Milk Everyday, which is about products that you can buy and then we’ve got Design Milk Travels. I mean there’s like six or seven Instagram accounts at this point, which is crazy. Kudos to our social media manager for juggling all of those things. (Laughter)
AD: And revenue is all coming in through ads and sponsored content, right?
JD: Yeah, so at that point it’s all advertising. In the beginning it was all banner ads and then it shifted to content, so now it’s mostly sponsored content and partnerships. So other things we do, whether it’s events or other things.
AD: That was where you sort of strategised taking Design Milk to, was out into the IRL with the Milk Stand and such like that?
JD: Yeah, so that’s having the team now was great because I could take on a couple of bigger projects every year and those would be sponsored events and then Milk Stand was actually one of the biggest milestones for us. I think it was 2015 or 2016, but what happened with Milk Stand was ICFF had an opening for a popup shop and this was like three weeks before the show. And somehow I told the PR team that we would do it (laughter).
AD: Oh my god, it’s ridiculous.
JD: This is what it’s like to work with me. I’m like, hey, we’re gonna do this thing, it’s three weeks, we’ve got to find 12 people to come and sell their stuff. We’ve got this big space, it’s gonna be awesome and somehow we pulled it off. And I think having this team help out with everything was really critical. I can come up with ideas, but I certainly need the team to help execute everything. Milk Stand continued to grow, so we’ve had our first few international shows.
We did Interior Design Show, Toronto, and we did London Design Fair, so we’ve been all over the world with Milk Stand, and only in a few short years.
AD: So as you’re diversifying the offerings and sort of adapting to the world around you, as it’s changing and growing and adding team members, the media landscape is also changing. What’s happening, because magazines are starting to tank around this time and you had originally conceived Design Milk as a magazine, a digital magazine albeit, but how are you responding to all the warnings and stuff that is happening in the media landscape?
JD: Yeah, so I would say like 2011/2012 magazines really started to hurt and a lot of those ad dollars got shifted to digital, so we actually benefited quite a bit from that and that was really awesome for us. It was disappointing to see some of my favorite magazines go under, or be off the radar, but I feel like it really helped us and being digital first, it was great during the pandemic because we had always been online, where other businesses were struggling to figure out how to bring their content online, we were already there.
So that was also beneficial for us. But the other thing that I think was an interesting time was, 2015/2016 when I started to think about ecommerce and that’s one of the reasons why we launched Design Milk Everyday, because we wanted to test and see people’s appetite for more accessible, affordable, modern design. On Design Milk it’s a lot of very expensive pieces or concept pieces. So Design Milk Everyday was a place where could put things that people could actually go online and click and buy.
And Milk Stand was part of that too, it was kind of testing popup shop, where are things going. I already had one foot in there thinking about what’s the future for Design Milk and I always have felt that diversifying what you do is going to keep you going because if you have all of your eggs in one basket, what happens when there’s a hole in the basket?
AD: (Laughs) Right.
JD: You know? So I needed to diversify too, so I was always thinking… And that’s why we also did more events because we wanted to have IRL experiences with people. And that always helps with networking too, being face-to-face with people is always great.
AD: So here you are with a bouquet of baskets, with eggs in all of them and then something major happens and I want you to tell this story.
JD: (Laughs) Yes, I’ve got all these baskets, all these eggs and I’m tired, I can’t carry all these baskets. And also I was thinking, what am I going to do? I’m by myself, I’m a single member LLC, I’ve got all these independent contractors and I at some point need to expand my business and I don’t know what that looks like. So I need to either hire more people or hire someone to help me run the company or get investors or sell the company and those were really my only options. At that point I was tired and I needed help. And I think the universe just answered me because I kind of gave myself a five year plan. In five years I want to get one of these things figured out.
But before I could even actively pursue anything, I get a phone call from AHAlife, which is an online ecommerce store that Design Milk had a long history of working with and the CEO had turned over and there was a new CEO in place, Robert Mancini and he called me and he’s like, “Hey, I’ve heard all these great things about Design Milk, I know you’ve worked with AHAlife, what are you doing now? Could we work together? I’d love to hear more about our previous partnership.”
So as we got talking it was really exploratory and very early, but he xwas really in interested in the Dog Milk website that we had, which we ended up folding into Design Milk under the ‘pets’ category. But it was all about dogs and design. And so we started talking about that -
AD: Two of my favorite things! (Laughter)
JD: So we started talking about that and then I was at a trade show and I get another phone call. He was like, “Hey, what if we just bought all of it?” I was like, oh, okay? I don’t think I want to sell Design Milk. I really was at the point where I was like, yes, I want to get rid of it, but also, no, I don’t want to get rid of it -
AD: It’s my baby! (Laughs)
JD: Yeah, I wanted to alleviate some of the pain points for myself, really, is what I wanted. So when he said that, I was… My immediate answer was no, but deep down inside, and he got this out of me (laughter), is I wanted to get rid of some pain points, but I still really loved Design Milk and wanted to be involved. So that’s kind of what happened. And it took a while and it was a big process, even though we don’t have any physical inventory or stores or anything, everything is digital, it still took a lot of time. But we got to the point where AHAlife acquired Design Milk and that happened in March of 2019.
AD: Well, okay, so March of 2019, I mean I’m not pretending like I wasn’t there with you when this happened, but at the same time it’s still a big deal. You’ve negotiated the acquisition and then you had to fold Design Milk into a bigger corporation and sort of integrate the ecommerce more, you’d already sort of started it, but it needed to be more fully integrated in with Design Milk without losing any of the quality or variety of the content. And your work family went from a few trusted confidants to a whole slew of people that you had to get to know and become a leader of immediately. So what did all that look like?
JD: So the first thing I said to Rob on the phone was, I don’t want Design Milk to just become this farm of links for products. The products really need to be something we would write about anyway and we need to continue to write about the things we’ve always written about. Because we wanted a media site and we wanted an ecommerce site and we wanted both of those things to co-exist and work together and you can’t really do that when one side is 90%, you’re only focused 90% on one side and 10% on the other, right? So the important thing was to kind of get the right balance and the right mix. So that was the first part of the struggle to try to figure out how to do that.
The second part was merging our teams together. We went from like four or five people who were all over the place, working from home, to having an office in Columbus, Ohio, with a team of people that none of us had ever met or worked with together and we were trying to bring these two very different types of companies together to work together. So the first year was like, I anticipated it would be difficult, but it was really, really hard.
And I also had just turned 40, so 40 was a big year for me, it was just like, oh my god, it’s a milestone. And then on top of that I did the acquisition deal. And then we had this really difficult year. So that first year was just personally and professionally overwhelming and exhausting and probably the hardest year of my life. But looking back, it was also kind of the best year - the most needed year.
AD: Because it catapulted you from one level to the next?
JD: It totally did! I had like an existential crisis. Like who am I without Design Milk because selling the company, you’re selling the company -
AD: Yeah.
JD: You’re not like, merging, it’s really like they’re taking it. So I had to come to terms with that, like what is that? What does that mean? Luckily I named it Design Milk and not Jaime Derringer (laughs) for a reason, I didn’t want to be the star of the show, it’s okay with me, but I needed to figure out how to detach myself from it. And I’m still working on that, but it’s still like this phantom limb. You still feel it, you still know it’s kind of there, even though it’s not. So there’s a lot of person work -
AD: Yeah, in early childhood development they call that ‘individuation,’ I think, right?
JD: Yeah.
AD: Design Milk had to form its own autonomous identity separate from you.
JD: Yeah, it’s like your kids going away to college and you also have to accept that your kid is a whole person in and of itself, living and breathing by itself and it’s not you. And you can try to influence it, but you can’t force it to do things. I had this whole moment where I was like wrecked emotionally and then I had to go through all of this professional, these meetings with these people I never knew and all these ideas throwing at me. I think that year was just really hard for me, but was so rewarding because now I’m like, I’m not a different person, but I feel like I’ve been through something that has changed me and changed me for the better.
AD: Well, those growth spurts are like that, and it sounds like that’s what it was, was a really intense growth spurt.
JD: Yeah and the other part of it that I am, I can come full circle from the beginning of when I was miserable at my first job because I just couldn’t work people, I’m not like that anymore. Because I learned how to work with people and that’s super rewarding for me because now I don’t feel like I have to do my own thing and only be the person who makes the decisions and runs the whole thing.
It’s kind of chipping away at the control freak part of my personality. It’s still there, I mean I’m still a huge pain in the ass, ask anybody that I work with (laughter) but it’s obviously coming from a good place. But yeah, I can feel like I can see myself changing in the way I react, so it’s positive.
AD: Well, not to insert myself into your story, but if I’m correct, you and I formed our partnership before the acquisition, which I know for sure. So maybe I helped break the ice in terms of you learning to work with people and share control.
JD: That is probably true because what I think is great about our partnership is you have strengths that I don’t have and I think both of us recognising what we’re good at and what we’re not good at, that we kind of fill each other’s, boxes or I don’t know, I don’t know what kind of metaphor you want to use -
AD: You complete me Jaime Derringer.
JD: Yeah, that’s exactly right (laughter). It works really well and I have people at Design Milk that are like that too. And so it’s kind of me learning to delegate or trust other people to do XY or Z and also just yeah, navigating different types of personalities. It’s a beautiful thing because I appreciate that everybody is different and not like me. And so I think once you also start to respect that about other people and take in their ideas and listen to them, that you could learn something new. They may have a better idea than you (laughter). I mean you and I have been there -
AD: Yes.
JD: You know how to deal with me.
AD: (Laughs) Yes, well, we do have to mention the origin of Clever at least a little bit. I don’t want to get too meta here on this podcast, but before we started Clever, I definitely had my antennae up for like-minded souls that I could collaborate with and they also had, like I think your hustle spoke to my antennae directly. Because I think we kind of fell in business love at first sight, didn’t we?
JD: Yeah, it was business first and then the friendship after - you know what it’s like - this is totally not related, but have you ever watched Married At First Sight?
AD: Yes, I have, based on your recommendation.
JD: Yeah, okay, so we need to know if anybody out there is watching it, but Married at First Sight pairs two people together, matchmakers match them together and then they get married like literally without ever having met. And then they follow them along to see if they stay together. And so I think that was kind of like what we did, we were like, let’s just -
AD: It was, now that you mention it (laughter).
JD: Let’s just do this thing and we really hadn’t even known each other that long and we just immediately trusted one another and we were like, okay, let’s do this and then afterwards we were like, yeah, we want to stay together, we don’t want to get a divorce (laughter).
AD: But we did have some herky-jerky moments where we were just figuring out, like your style and my style and our strengths and playing to our strengths. But that’s what I think is so lovely and organic about this particular partnership, which is a separate baby of yours than Design Milk, and mine, we’re co-parents of this baby. But we’re both so invested in it that it’s sort of, like we had to become self-aware in order to make the partnership work.
JD: Yeah, and I think that your friendship has helped me tremendously in that area, both professionally and personally, so thank you Amy.
AD: I love you Jaime. Okay, now let’s get into your creative process. But before we get there, I want to talk about your creative process in media and you’ve already said you’re really good at coordinating things and project managing. But how do you approach/dream up the ideas and the strategy? How does that ferment in your soul and manifest?
JD: Everything I come up with creatively is either something that I think would be fun to do, or something that I think I would enjoy as a consumer, whether it’s a consumer of media, whether it’s a buyer of goods on an ecommerce website, or just interacting on social media. I just try to figure out what people want to engage with and then go from there. That applies to media and ecommerce because ultimately it’s all about marketing right?
Just figuring out what are the marketing moves that are going to compel people to either read something or be interested in something or subscribe or buy, whatever it is that they are gonna do, it’s like how do you make that experience fun and interesting or informative? And how do you make it so that they want to share it with other people? And that has always been my thought process behind all the creative stuff.
AD: And just to get more granular with that, what is the thought process? Are you decoding psychology? Are you just paying attention to the ebb and flow of attention spans?
JD: I think it’s because I’m a consumer of the internet myself. So I really think it’s germinating inside of me as a consumer of visuals or goods or whatever it is. So I’m just thinking what would I want.
AD: Yeah.
JD: And then there’s times when I’m on the phone and I’m like, you know what would be a cool idea, if we did this? And it just comes out of brainstorming and riffing off of what other people are saying. Sometimes it just happens during a phone call when we’re all just trying to figure out what we should do next.
AD: I love those, those are such fun surprises (laughs) when you don’t have to muscle through trying to work up a brilliant idea, but they just drop in your lap.
JD: Yeah, it happens a lot and sometimes I have to rein myself in because I’m like, we can’t do this. (Laughter) Like I can only do so many things in 24 hours, I’m only human. And we have a team, we can’t do everything all at once with the team that we have.
AD: You can do anything you want to do, but you can’t do it all at the same time.
JD: Right.
AD: You’re an artist as well, can you tell me about what media you work in, what holes it fills in your life and what your process looks like in that sphere of your world?
JD: I started drawing in 2006, the same year that Design Milk was born. It was one of my most creative years I had a little bit of a creative renaissance recently too because I’ve moved from drawing and painting into more physical objects. I’ve been tufting, which is like you get this punch needle gun, it’s like a machine and drive the yarn into fabric and make it into different shapes and stuff. I think I’m just scratching the surface of what’s possible with it but it’s super fun and I like it because it’s physical.
Drawing is great because I can sit in front of my TV and watch Netflix and draw, or painting is also really fun, but the tufting, it’s super physical and my arm is sore at the end of the day (laughs). I can see my work and I can -
AD: It’s tangible results of your creativity -
JD: Yeah, it’s like buzzy -
AD: Welcome to making baby! I could have told you this years ago!
JD: I do love it, I do love it. So yeah, so I’m mostly drawing and I’m doing a little bit of painting and then quite a bit of tufting. But painting has been a struggle for me, so I’m still kind of trying to navigate that. The other thing I was doing too this year was digital art. I’ve been learning some programs and writing some code, which is really cool. Yeah, so I’m learning all kinds of cool new things and it’s just, I don’t know, I’m having a creative brain explosion this year, which is really great and exciting.
AD: Oh god, don’t get near, you’re gonna get brain shrapnel on you. (Laughter) Okay, so you had mentioned the birth of your daughter 10 years ago, obviously that’s a big milestone in your life and you’ve been a mother for 10 years now. I know it’s a challenge, I’m not a parent myself, but I’m not stupid, I mean I see the challenges that my parents went through and that my friends that are parents go through. But I also see how it enhances people and I guess that’s what I’m interested in from you. I never knew you before you were a mother. So what would you say, how has your character or your personality or your being been enhanced by motherhood?
JD: Ooh, that’s a really good question. The first thing I noticed a shift, the first shift I noticed was I came face-to-face with my own mortality. And that is huge. It’s kind of like having a near death experience. As you watch this person grow, you realise that they’re gonna go to your funeral. And you realise that they’re gonna lose someone they love and that’s really hard. And that you’re going to die one day and it just becomes more, I don’t know, life just becomes more vibrant and more interesting and more exciting, but also time becomes so much more precious. The only thing we really have in this world is time. Who cares about money? Who cares about success?
AD: Time and relationships.
JD: Yeah.
AD: Yeah.
JD: Time with people you love.
AD: Well, it’s a good thing your daughter turned out so fucking cute! (Laughter)
JD: She’s awesome; she’s very creative too, which is good.
AD: Oh, I know, so, just to get deeper into this existential line of questioning, you mentioned you’ve been doing a lot of self-reflection and self-growth lately, which I think is, you’re right on time and that’s the important thing to do because you’re not stagnating or remaining stuck. But what for you is the growth edge, like where are you growing right now?
JD: Well like I said before, my self-awareness is increasing on a daily basis, so that’s a really interesting new thing. I think before I felt very, not robotic, but just kind of going through the motions and never really stepping back to look at myself and look at myself in the grand scheme of things and then look at my relationships with others. So I think that that is part maturity and just part spiritual work.
AD: Do you think the hustle was in any way a distraction or an avoidance of that, looking at that?
JD: I do and I talk a lot about this with my therapist (laughter). Yeah, it was, but like I also feel like it was a survival mechanism for me, that I needed at the time and I feel really grateful for it -
AD: Yeah.
JD: Because it set me up nicely to feel secure in a job. I mean 15 years doing the same thing, it’s like a beautiful, wonderful, amazing thing and I’m really grateful for that.
AD: Just even becoming aware of our survival mechanisms and getting to the point where you can have appreciation for them but also a kind of perspective that helps you know whether they’re serving you in all instances or not and when to employ them or not employ them is, I think, a really powerful place to get to. You had mentioned something about spiritual growth too, but you were never really a religious person. So what kind of spirituality are you growing into?
JD: I’m doing a lot of meditation and that really helps me connect with who I am. I talked earlier about struggling with my own identity I think the acquisition and when I turned 40, it forced me to confront myself and say, who am I? Think about who am I without Design Milk and who am I as a person. So that work has been ongoing for two years, just trying to figure out who I am without all of the things that are physical attachments or personal belongings or whatever (laughs). Who am I when I’m alone in a dark room, figuring that out is really eye-opening.
AD: Do you see any similarities to the young Jaime Derringer, hot mess who was alone in a dark room writing poetry and listening to Nirvana?
JD: I’m reconnecting with that person (laughter).
AD: She’s probably pretty awesome!
JD: Yeah, she’s really cool, but she doesn’t have confidence, but now I have the confidence, so I’m connecting, like I’m the adult Jaime with more confidence, connecting with that angsty teen writing poetry and it’s really, it’s becoming this beautiful thing that I’m watching happen. It’s not overnight - but it’s something I’m working toward and I feel really good about it.
AD: Well, I feel good about it too and that leads me to my next question which is sort of, where are you projecting yourself in the future? I mean after a year like 2020 we know that plans can sometimes just be pointless or ridiculous, like they all go out the window as soon as the world changes rapidly. But also you had a great amount of success before when you were without a plan, in terms of finding your way to Japanese studies and just starting Design Milk without a plan. So clearly you’re good at adaptation and that will always be a super power. So with that in mind, what does a super-adaptive, bionic wonder woman, future Jaime Derringer look like and what kind of world does she want to build and foster?
JD: My least favorite question is: Where do you see yourself in five years? Because I don’t look too far into the future. Being a project manager, you’re always planning, but the greatest part of what I’ve learned about planning is your plans always get fucked up. You need to plan for fucked up plans. So that’s what I do. I think about where I want to go and what I want to do, but I focus more on the journey and then I course correct as things change.
And I think that’s a good project manager, but it’s also a good life lesson because you’re never going to have a perfect week where everything goes your way. There’s always going to be a random thing that happens. Your kid falls off their scooter and breaks their wrist and then you end up at the ER for three or four hours. That kind of stuff really happens, you know, in life.
AD: Did she get her cast off yet?
JD: (Laughter) She did, yeah, she’s doing good, but yeah, I mean these things just happen. It was the perfectionist in me that expected everything to go as planned and it always did when I was in charge. (Laughs) But now what I’m learning is that when other people are in charge, I defer to their leadership and their expertise. I do what I can on my side, but I can course correct really easily when things don’t go as expected. And that’s the beauty of being able to work with a team.
AD: Well, that sounds wonderful if you could have some influence over how our world changes towards something, what direction would that be?
JD: Ooh, well, having a child is a huge responsibility, so clearly anything I’m learning I want to impart that knowledge on my daughter because she’s the future generation. So the decisions she makes will carry on through the future -
AD: Yes.
JD: So that’s a huge part of it. I don’t think we put enough emphasis on the responsibility of parents and parenting, it’s like a giant role in shaping the future -
AD: It is.
JD: You know -
AD: Yes.
JD: I can do what I can do now, but I’m gonna be dead in how many years and she’s gonna carry on whatever I teach her -
AD: Quit talking about dying.
JD: Okay, sorry, sorry, it’s a real thing (laughter). No, but I also feel like you know, in my tiny circle, I can do what I can do right? I can make small changes in my life, or small suggestions to our business on things we can do to change how we do things in order to allow for more opportunities, to be more inclusive. That’s been huge for us, something that we really care a lot about at Design Milk. I don’t know. I just want, I don’t know, I’m such a hippy Amy (laughter). Deep down inside I just want everyone to love one another. It’s really weird, but that’s where I’ve gotten to in my life, like where I’m… I see so much struggle and so much division and I’m really at the point where I just… It’s heart-breaking to watch. And also it’s hard to not want to save everyone and help everyone and fix all the problems of the world.
AD: Part of what it all is, is recognizing the corrosiveness of the lack of love and then just trying to move everything toward love. I mean not to sound corny, but I think it’s really that simple.
JD: It is that simple. It is that simple, I think. It’s a lot of love.
AD: All right, well we’ve got a lot of love here between you and me, what’s next for Design Milk?
JD: Well, Design Milk has, let’s see, it’s 15 years this year, so we’re celebrating our anniversary, so we’ve got a lot of great content coming up on the site where we’re looking back at some of the highlights and our favorite moments. Some of our most popular posts. We’re also doing some collaborative products on the Shop, so that’s coming up soon. You know, for the future, it’s still the same way I feel about my personal future where we’re an internet based company and the internet changes all the time.
So we’re small enough and flexible and agile to be able to adapt to any kind of thing that’s thrown at us. We just went through a pandemic and I feel like we did a good job navigating that. I would just see us continuing to change and adapt with what’s new and next online.
AD: Stretchy! Flexible! (Laughter) Squishy.
JD: You have to be, right? You don’t want to be left behind. Yeah, and you know I’m, I’m looking forward to seeing what Design Milk becomes. It’s been two years since the acquisition, Rob is our CEO, I have a great partnership with him and I feel like he understands the vision that I originally had for Design Milk and that he’s adding all of this extra awesome stuff on top. And I think he’ll steer us in the right direction.
AD: Well that also gives you confidence doesn’t it, to know that partnerships are solid and it’s because you’re building these really foundational relationships.
JD: Yeah, it’s super important to me too because Design Milk isn’t called Jaime Derringer, right? So now that it’s all these other people and that we have a CEO, that’s not me, it’ll be great to see how it continues to expand and grow.
AD: Just like when your baby grows up, oh my god, Design Milk is gonna get a boyfriend, then what are you gonna do?
JD: Oh no! (Laughter) I don’t know! (Laughter)
AD: Well, so much of our day-to-day operations are pretty much about getting our business done, but whenever we get a chance to stop and I get to gaze upon your beauty and (laughs) learn more about you, it always makes me just so happy that we’re doing this together.
JD: Yeah, this is great. I’m so glad that we got to talk some more. I feel like Design Milk being 15 years old, it’s a huge milestone and it’s a milestone for me personally too, because other than being married to my husband, I’ve never done anything consistently for 15 years, so I feel like I need to give myself a small round of applause for sticking it out for so long. (Laughter)
AD: Yes, and your daughter is at 10 years, so you better keep her to 15 at least.
JD: Yeah, yeah, I think she’s good, she’s pretty independent now; she can survive on her own without me. So I’ve done my job! (Laughter)
AD: Thank you Jaime Derringer.
JD: Thank you.
AD: Thank you for listening! To see images of Jaime’s work and read the show notes, click the link in the details of this episode on your podcast app, or go to Cleverpodcast.com where you can also sign up for our newsletter. Subscribe to Clever on Apple Podcasts, Spotify, Stitcher, or wherever you get your podcasts. And do us a favor and rate and review, it really does help us out. We also love chatting with you on Twitter, Instagram, and Facebook, you can find us at Clever Podcast and you can find me at Amy Devers. Clever is produced by 2VDE Media with editing by Rich Stroffolino, production assistance from Ilana Nevins and Anouchka Stephan and music by El Ten Eleven. Clever is part of the Airwave media podcast network, visit airwavemedia.com to discover more great shows. They curate the best of them, so you don’t have to. Clever is proudly distributed by Design Milk.
Many thanks to this episode’s sponsor:
Dunn-Edwards
The Dunn-Edwards Emerging Professionals Design Competition is calling all emerging professionals, currently enrolled students of architecture and interior design! This is the time to practice your developing skills in commercial and residential design categories and get rewarded. Two grand prize winners will each receive $3,000 cash. Beginner and advanced levels are encouraged to apply. Submit now through August 6 at emergingprofessionalsprogram.com to earn your bragging rights!
Jaime Derringer, photographed by Jenny Siegwart.
What is your earliest memory?
Standing up in a crib at our first house. We moved when I was 3 or 4, so it’s a very early memory!
How do you feel about democratic design?
It’s incredibly important and I think more companies should be creating well-designed products that are accessible, affordable and available for all.
Little Jaime.
Jaime in Japan in 2001.
Jaime dressed as Boy George.
What’s the best advice that you’ve ever gotten?
“Start now.”
How do you record your ideas?
I am old fashioned and I use notebooks and pens.
For my artwork, I have been keeping a sketchbook since 2007!
What’s your current favorite tool or material to work with?
Right now: yarn!
90s Jaime
Jaime and Nana.
Jaime’s headshot evolution
What’s the best book you’ve read this past year?
Bunny by Mona Awad
Be Water, My Friend by Shannon Lee
Why is authenticity in design important?
As a media partner and strong supporter of Be Original Americas, Design Milk has always tried to support original and authentic design. It’s important to support designers who spend time on the research and development of an idea because it takes a long time and a lot of work to design and create a product or project. Supporting this process means supporting and rewarding all the folks involved.
Jaime and Design Milk editor Kelly Beall.
2015 Milk Stand
Favorite restaurant in your city?
It’s hard to choose, but at the moment, it’s Mimmo’s or Barbusa in Little Italy (San Diego).
What might we find on your desk right now?
A mess of pens, papers, hair ties, sticky notes, notebooks, face masks and various cups of water and coffee. Also, Apple/Mac adapters, extra mice, earbuds…
On the other side of my desk, I have a few synths & drum machines and another computer for composing music. I clean it every few weeks once it gets too crowded! 😬
Design Milk logo evolution
Who do you look up to and why?
I’m inspired by the teachings of Baba Ram Dass.
Design Milk 2013
Design Milk website 2021
What’s your favorite project that you’ve done and why?
This is impossible to answer as there have been so many! Launching the Design Milk Shop has been one of the most exciting, ongoing projects! Also, our Milk Stand popup shops have been super fun to work on, as are our DMTV Milkshake episodes.
Jaime and Amy Devers.
What are the last five songs you listened to?
“Can’t Find my Mind” - The Cramps
“Primitive” - The Cramps
“The Depth” - Posthuman
“Run Da Ting” - Denham Audio
“Allure” - Amy Dabbs
DM Editorial Director Caroline Willamson, Jaime, DM writer Leo Lei and former Account Manager Melissa Green at Design Milk’s 10th Anniversary party at Blu Dot in New York, 2016
Design Milk shop
Clever is produced by 2VDE Media. Thanks to Rich Stroffolino for editing this episode.
Production assistance from Ilana Nevins and music by El Ten Eleven—hear more on Bandcamp.
Shoutout to Jenny Rask for designing the Clever logo.
Clever is a proud member of the Airwave Media podcast network. Visit airwavemedia.com to discover more great shows.
Keep Listening
Ep. 151: Architect Chandra Robinson
Ep. 149: Creative Leader Brian Rice
