I think a good interview is like a game of pool. You not only want to have a good question and a great answer, but know where that answer might end up, so that you can prepare where to shoot next, so to speak.
— Debbie Millman
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Tara: Welcome to Profit. Power. Pursuit. I’m your host, Tara Gentile, and together with my friends at CreativeLive, we talk to powerhouse small business owners about the nitty gritty details of running their businesses, making money, and pursuing what’s most important to them. Each week, I deep dive with a thriving entrepreneur on topics like time management, team building, marketing, business models, and mindset. Our goal each week is to expose you to something new that you can immediately apply to growing your own business.
My guest this week is Debbie Millman, host of the first and longest running podcast about design, Design Matters. Debbie is also an author, educator, and brand strategist. She’s the chair of the School of Visual Arts Masters of Branding program, the Chief Marketing Officer at Sterling Brands, and President Emeritus at AIGA. She’s interviewed superstars, and some of my personal heroes, like Malcolm Gladwell, Dan Pink, and Seth Godin. Last year, iTunes named Design Matters one of the top 15 podcasts. I wanted to find out how hosting Design Matters has impacted Debbie’s life and career. We talk about the 10 to 12 hours she puts into interview prep, how she started with just a phone line back in 2005, and the opportunities that have come her way thanks to the podcast.
Debbie Millman, welcome to Profit. Power. Pursuit. Thank you so much for joining me today.
Debbie: My pleasure, Tara, thank you for having me.
Tara: Absolutely. So you’ve been running the internet radio show and podcast Design Matters for over 10 years, which is a long time in any internet pursuit at all. Can you tell me how the show got started and why you decided to incorporate this, you know, at the time, fairly new media into your design and branding career?
Debbie: Absolutely. Well, I should clarify in some ways that the show didn’t start out as a podcast, because there were no podcasts back then. The show actually started out on an internet radio network called Voice America, and it was a little operation that ran out of Arizona, and I believe they’re still in business, but at the time, it was a really fledgling enterprise, and working with them was a little bit like working with Garth and Wayne on Wayne’s World, but they were really wonderful people. I actually got cold called from them about doing a show on design and branding, and at the time, I was really honored and thought that they were offering me a job, and what I later came to find out was that actually, they were cold calling me to be a host, which would require my paying them to pay for the production and the air time, but at the time, this was 2004, I had just begun to start doing personal work again after essentially abandoning all my personal work in an effort to build my branding career for the previous 10 years.
And the call came at a time when I really felt like my creative soul was perishing and had just begun to start writing again. I hadn’t begun to start doing any of my personal illustration yet, and I felt like I needed something to buoy my creative spirit, something that didn’t have anything to do with marketing and positioning and market share and research, and something that required … I didn’t want to have to be selling anybody anything in doing this, and here was an opportunity that I had never, ever gotten before, and thought why not invest a little bit of money in myself and my desire to try something new, and Design Matters was born, and I often say now that it was born with a wish and a telephone line, because that’s how I did the show. I would use a telephone handset to do my show, and my guest would be on the phone with me. Often, my guest was in front of me, and so we were both on handsets, and so I don’t know if you’ve ever picked up a landline while somebody else was on the same landline in your vicinity, but you often get an echo, and so that’s how I did the show. There was always an echo going on. My listeners didn’t hear the echo part, but it was really distracting.
I had really, really goofy ads that ran at different times during the show, but it gave me an opportunity to approach the people that I admired most in the design business and interview them, and essentially, I was given carte blanche via the use of an interview, or the excuse of an interview, to ask all of the questions that I was curious about, and I had a million questions, and so I did the first 100 episodes on Voice America, and then in 2009, the late, great Bill Drenttel, the founder of Design Observer, invited me to bring the show over to Design Observer, with the proviso that I improve the sound quality. And he introduced me to Curtis Fox, who is a producer, and at the time, he was working at the New Yorker and the Poetry Foundation doing their podcasts, and so we started working together. The School of Visual Arts was very supportive. That’s where I have my branding program, and we were first building the studio, and so they incorporated a podcast studio into my space, and so since 2009, I have been recording the show live at my studio at the School of Visual Arts in front of my students, live student audience, sort of like Inside the Actors’ Studio, and then my guests, when they’re finished with the interview, they come out, and they’re asked questions by my students, which is really, really fun for them, and for the guests, and I’ve done I think about 260 or 70 episodes at this point. So the show won the Cooper Hewitt National Design Award in 2011, which Bill was really, really involved in helping me win, and then last year, iTunes named it one of the top 15 podcasts on iTunes, which was a dream and a miracle.
Tara: That is so awesome, and I totally missed that you recorded live in front of your students in my research, and I find that fascinating. Can you talk just a little bit about how that works, and like what your students get out of it, why you decided to do that?
Debbie: Absolutely. One of the gifts that I could provide to the students was access to these incredible minds, and what better way for somebody to learn through listening to somebody talk about their life, and to be inspired by their trajectory. And the show has changed a little bit over the years. The show really began, initially, as a show very much about design and branding. The show now is really, it’s still … it’s still very much about design and branding, but the centerpiece of the show is really for me to talk to my guests about how they design a life filled with creativity and purpose. And so for students, and these are my graduate students, although my undergrads can also sit in if they like, they are given access to the journey that the artist, the writer, the designer, the creative soul has created their path. What decisions did they make? What obstacles did they face? How did they design the arc of their life to date? And I think that it’s become a really meaningful component to the program that I have at SVA, the Master’s program in branding, because it teaches people how essentially my guests have branded themselves, and how they have created a life that stands for something, and that’s really, in my mind, what branding is. Deliberate differentiation, and how do you stand for something that you believe in.
And so I think the students get a tremendous amount out of it. They’ve gotten jobs from some of my guests and have learned an incredible amount and have read incredible books in preparation for their own questioning, and so I think it’s a really signature part of the program now.
Tara: That is so cool. I will be filling out my application after this interview. No. Seriously, though, Michael and I, my producer and I were just talking about this yesterday, how hosting a podcast is very much like having sort of a private but public mastermind where you just get to pick other people’s brains and find out how things work, and I just … I love that you’re involving your grad students in that as well, and I think that’s such a powerful tool for them, and I just can’t even imagine how powerful that experience might be.
I do want to rewind a little bit as well back to your first answer, and ask you a little bit more about, you know, you said you were just … when the podcast started, you were just starting to write again and you hadn’t yet starting doing illustration again, and you know, you needed to flex your own creative muscles some outside of the business world. Can you talk about how your personal creative pursuits have informed the way you’ve, you know, molded the podcast, or even just molded your career in general?
Debbie: Sure. When I graduated college, I had a degree in English Literature and a minor in Russian Literature. And I went to SUNY-Albany, which was an extraordinary experience for me. My on-the-job training really was as editor of the arts and features section of the school newspaper, and so when I graduated, and I often joke I have a degree in reading, I … my only marketable skill, in order to get a job that had some aspect of creativity to it was doing very traditional old school layout and paste-up, and so … and that’s how I got a job. I was absolutely determined to live in Manhattan. I wanted to live in Manhattan. That was the only thing I can look back on the journey of my life and say that’s the one thing I knew for sure. Everything else was very much how could I do this? Am I good enough? Am I smart enough? Am I capable enough?
But moving to New York required just the deep, deep desire to do it, and I had to figure out how to pay my rent, and so I really … I felt really bad about myself, and I didn’t have any confidence to pursue what I really felt in my heart I wanted to do, which was a combination of art and writing and music and a really creative life. More fine art than commercial art. But I only had my commercial art skills, and for the first 10 years of my life, I really floundered. I had very little confidence. I had very little experience, and just kept sort of going from rejection to rejection, and sort of failure to failure. I quite by accident ended up in the field of branding, and because my background growing up included working in my father’s pharmacy, I had had a relationship with brands almost as early as I could talk and walk, and had spent a tremendous amount of time in his pharmacy, spent a lot of time at the cash register helping him out, and really had this innate understanding of brands and how people shop and why they buy the things that they do.
His pharmacy was more of a general store than just a pharmacy. It was a general store with a pharmacy in the back, and so I found quite by accident … and probably serendipitously, that I was very good at branding. Almost as if it were a natural talent. So the second ten years of my career were building this career. Building this ability, and finding that I was really successful at it, and that began to help me build some confidence, and I talk quite a lot about how I’ve come to believe that confidence is really overrated. Dani Shapiro said this once to my students after her podcast when somebody asked her about being confident in life, and she felt that confidence was overrated and felt that most really confident, overly confident people, or very visibly confident people can often be kind of obnoxious, and felt that what was way more important was courage. The courage to take that step before you have any success. And I think all confidence really is, is repeated success at doing something over and over. You’ve done it before. You know it’s come out well. You expect that when you’re going to do it again, you’re going to do it well again. So what is really more important is courage. To take that first step before you know if you are going to be successful at doing something, and then confidence is built from there. But I think that because I started to feel somewhat more successful, and definitely more secure financially for the first time in my life. I then had a little bit more freedom to begin to do all the things that I had given up in pursuit of my branding career, which included writing and painting and drawing and creating things with my hands.
Tara: I love that. I love the transformation, and I love the reframe around confidence and courage. I know that’s going to be a big takeaway for people.
So shifting gears a little bit. I listened to the Creative Mornings presentation that you did on their podcast, and you said that if you’re not making enough mistakes, you’re not taking enough risks. So what are some of the risks and mistakes that you’ve made with the Design Matters podcast?
Debbie: Well, I think the biggest mistake that I made was underestimating how long I would do it, and I mean, I hope to be able to do Design Matters for the rest of my life. It’s one of the things that I feel most important to me, and really helps … has helped give me a sense of purpose for being alive. But when I started the show, I started it with this little fledgling phone line, and the sound quality was really terrible, so I had done these 100 episodes, and the sound is sometimes so bad, you can’t even listen to the show. So those, so I wish that I had taken it more seriously from the start, but it’s very, very … it’s … this is something that I tend to do in my life.
I don’t take things as seriously as maybe I could or should, just because I’m the one doing it, and so I wish that I had taken it a little bit more seriously or taken the effort more seriously, because those hundred episodes don’t really sound as good as I would like them to sound. That’s the biggest regret. Other than that, I didn’t have a logo for the show for the first … which is kind of ironic. I finally asked Armin Vitt to help me do that. I’ve never … I don’t think I’ve given the show my own sort of personal respect in the way that I probably should. It took me a really long time to get my own website. It took me a really long time to get my own logo. Armin Vitt has been really helpful in helping me do that. I … Maria Popova has helped me, my partner, Maria, has helped me really understand how to better talk about the show online and take the social media aspect of it a lot more seriously, because it’s a labor of love, and not something that I ever did to, for business purposes or to raise money or to make money. I probably have not been as diligent about building the brand, so to speak, as I have in my other work.
Tara: That’s fascinating, and very relatable.
Tara: So, you know, you just said that you haven’t ever done this for business purposes, but at the same time, I’m sure the podcast has had a big influence on your career, maybe on opportunities that have come your way. Can you talk about how the podcast itself has really influenced your branding and design career?
Debbie: Well, I don’t have any empirical today to say that because I did this, this occurred, but I think that it was my entree into the design discourse of our culture, and that has, because this show tends to travel far and wide via iTunes and Soundcloud and Stitcher and so forth. There are people that listen to the show that I never would have imagined would receive and be interested in it, and so I think that most of the invitations that I get to speak in different countries, most of the invitations I get to judge competitions come via people being exposed to me through the podcast, and so I think either that or my books, and both of those sort of happened consecutively, and so, or concurrently, rather, and so I think that … that it has helped introduce my thinking to the broader design community globally.
Tara: I might be a professional educator and expert, but that doesn’t mean I’ve stopped learning. When I’m ready to learn a new skill, the first place I go is CreativeLive. Check out this great class.
Alex: Anyone can benefit from learning to tell better audio stories. Whether you’re a reporter on the radio, or you’re an entrepreneur trying to tell an effective story about your business. In this workshop, what I’m doing is sort of unpacking what exactly is a story, how can you be effective in telling stories, and how can you lay them out in a way that they get maximum impact with your audience. You’re also going to learn a lot about the art of the interview. If you’re interviewing somebody, how do you make sure that the interview is engaging, is informative, has moments of emotional resonance? I also have a formula that is actually, you know, it’s actually a mathematical formula that tells you how am I on the right track when I’m thinking about telling a story. I’m Alex Bloomberg, and this is Power Your Podcast with Storytelling.
Tara: So we really like to get into the nitty gritty here. So I want to know how you personally prepare for interviews, because I know how I prepare for interviews, but I’d love to hear, you know, what’s your process? When you’ve got a great guest, and you have had some amazing guests, what is your process for thinking about how you’re going to approach that interview, what you … what kind of background you want to know, what maybe you don’t want to know before you sit down with that person?
Debbie: I believe that my podcast, a podcast, any podcast that I do is successful when the guest looks at me and says, “How do you know that? How did you find that out? Did you talk to my mother?” I do a tremendous amount of research. I probably spend upwards of 10-12 hours preparing for the one hour interview. I … if they’re somebody that has published books, I like to read everything that they’ve written. If they have created work, I try to see everything I can possibly see. I am vigilant, and I love researching. I mean, how many times do we go internet surfing and feel guilty that we might be, so to speak, wasting time going into these little wormholes of research just for the fun of it? Well, I get to do it as part of my job. So I’ll start with a link, and that’ll take me to something else, and that’ll take me to something else, and before you know it, I’m, you know, at their birth certificate. So I just do a tremendous amount of investigation, essentially, trying to understand the entire arc of a person’s life. Where were they born? What were they like when they were kids? Where did they go to school? What did they major in? Did they get a graduate degree? Where did they work? Where did they … where is every place they’ve ever worked? What is everything they’ve ever made? And go from there.
Tara: Ah, okay. Do you think design thinking has influenced your, you know, the approach that you use to that research or to that preparation for your podcast?
Debbie: Probably. I use a lot of post-its.
Debbie: Yeah, I do think so. I mean, part of what I do for every show is essentially create a script, and I have probably somewheres between 40 and 50 questions prepared. And I think a good interview is like a game of pool. You not only want to have a good question and a great answer, but know where that answer might end up so that you can prepare where to shoot next, so to speak. And that’s what you want to do in a game of pool. You want to not only shoot a ball into a hole, but you want to be able to shoot the next ball into the next hole, so it’s very strategic, and so for me, I feel most secure when I am doing an interview that any answer that my guest would provide, in many ways, I already know the answer and know where I want to take the conversation next, or if they surprise me, I want to be able to at least know enough about the topic to be able to ask an interesting question. I never want to ask questions that my listeners would already know the answers to. I want to be able to constantly surprise my listeners with information about my guests that they might not be able to get otherwise all in one place.
Tara: Wow. That is a game-changing answer for me. I will be incorporating that for sure in my own process from now on. Do you have a team helping you out with the podcast?
Debbie: No. I do everything myself, except for the production. And the production is done by Curtis Fox. He’s been my producer since 2009, and he has really helped me evolve the show to where it is now. So he … his voice at the beginning and end of each episode, and he essentially takes what usually is about an hour to an hour and fifteen minutes worth of tape and edits it into usually about half of what I’ve taped for. So if it’s an hour and fifteen, it’s half that. If it’s an hour, then he ends up with about 30-35 minutes, and essentially, he edits based on what he thinks is interesting. Am I getting bored while I’m listening to this? Or do I feel like it’s keeping my attention throughout? So he keeps it really snappy, really breezy, takes out all of my mistakes. I often make mistakes, and takes out the ums and the uhs and the likes and the kind of sorta things like that.
Tara: Fascinating. And do you guys collaborate on that at all? Or is that just, that’s his role?
Debbie: That’s his role.
Debbie: I do not … I do not listen to the edited podcast. I trust him entirely.
Tara: Wow. That’s amazing and awesome. Thanks for sharing that. All right, so one more question about the podcast, and then I want to ask you about the class that you have coming up for CreativeLive. How do you balance the needs of the podcast, and I know there are many, I mean, you said you prepare 10 to 12 hours for each guest, against the demands of the rest of your career, because you’ve got a lot going on as well with that, and you know, our listeners are always interested in, you know, how people balance things, how they manage their time, how they fit it all in. So can you talk about that a little bit?
Debbie: Absolutely. I don’t really believe in work/life balance. I feel that my, almost all of my work is a labor of love, and I love doing it, and I feel privileged to be able to do it, so I don’t feel resentful of the time that I dedicate to doing, I would say, most if not all of my work. I love doing it, and because it’s such a privilege, I … what I … I often say that I don’t find the time to do things, I make the time to do things. And one of my favorite slogans is that busy is a decision. You prioritize what you want to do in the order you want to do them, and if you don’t make the time to do something and say that you’re too busy to do it, what it really means is you don’t want to do it, and so I often urge my students to be really clear about what they say they can and can’t do because of busyness, because if they can’t do something because they’re too busy, maybe they should reconsider how much Game of Thrones they want to watch, or what they do while they’re watching Game of Thrones. And so I spend a lot of time doing the things that I love and have been really trying hard over the last three years or so to only do things that I love. I’m approaching my 55th birthday, and want to be really clear the older I get to only be doing the things that I truly, truly love, and then it’s just about joy and doing things with my whole heart.
Tara: Nice. Nice. And yes, busy is a choice. I love that. So you’re teaching a class here on CreativeLive. Can you tell us what we can look forward to with that?
Debbie: Yes. Part of what I discovered having that first 10 years of what I call experiment and rejection and failure, and then the next ten years really trying to make a career is how much how you feel about yourself influences your success, and so much of what we can and can’t do in our lives comes from how we edit, how we censor, and how we tell ourselves what we can and can’t do because of how we feel about what we can and can’t do. So this is a class called A Brand Called You, and it’s very much how to position yourself to create a career that you love, to create a life that you love, based on what it is that you love as opposed to what it is that you fear, and so it’s very much about how to create a point of view, how to develop a resume and a portfolio, and your own personal marketing campaign to go after what you want and get it.
Tara: Beautiful. So important. Absolutely love it. Well, Debbie Millman, thank you so much for talking with me today. This has been really great.
Debbie: My pleasure. Thank you so much for having me.
Tara: Find out more about Debbie Millman at DebbieMillman.com, or find her podcast, Design Matters, on iTunes.
Next week, I talk with Cory Whitaker and Parker Stevenson from Evolved Finance. I turn the tables on them, and find out how they use financial reports and tracking in their own business to project cash flow, make hiring decisions, and set goals.
CreativeLive is highly-curated classes from the world’s top experts. Watch free, live video classes every day from acclaimed instructors in photography, design, audio, craft, business, and personal development. Stream it now at CreativeLive.com.
This has been Tara Gentile. Discover how to accelerate your earning as a small business owner with my free class, Revenue Catalyst, at QuietPowerStrategy.com/PPP.
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Our theme song was written by Daniel Peterson, who also edited this episode. Our audio engineer was Kellen Shimizu. This episode was produced by Michael Karsh. We add a new episode of Profit. Power. Pursuit. every week. Subscribe on iTunes, Stitcher, or wherever you love to listen to podcasts so you never miss an episode.