Eat My Words

Johanna Almstead:
Hi, everyone. The inspiration behind this podcast is the amazing dinners I've shared with spectacular women in my life and the fact that some of the most transformative conversations I've ever had have happened over food and wine with my friends. As I prepare for each interview, I like to think about what I would feed them if they were coming to my dinner table. For my guest today, I'm going to do something hearty and warm. She loves a big, bold red wine and is a carnivore. Let's start with a gorgeous bottle of a Bordeaux red wine, maybe from Saint-Jul, which is one of my favorite places and wines in the world. I think I'll do a little charcuterie with some prosciutto and salami and maybe a couple of good stinky cheeses with some olives and marinated peppadews. She's an adventurous eater and likes rich flavors, so I think I'm going to make some grilled lamb chops with garlic and rosemary. I'd serve them with some roasted lemon potatoes and some grilled asparagus and maybe just a simple arugula salad on the side. And for music, I think I'm going to do a mixed playlist with some Arlo Parks, maybe some Japanese Breakfast and some Leon Bridges. I'd light all the candles and make sure the vibes are good. I've been lucky enough to share many dinners with my next guest, and I learn something from her every single time. Let's dig in.
Hello, everyone, and welcome to Eat My Words, the podcast. I'm so excited for today's episode. And yes, I do sound like a frog. I'm sorry. But we are going to persevere through this. For those of you that listened to the very first intro episode of this podcast where I told the story of throwing a dinner party in my New York City apartment with a group of amazing women to help me find my way out of a confusing and difficult time, which then set a trajectory of a now decade-long tradition of that same group of women getting together over food and wine and hashing out our lives.
My guest today was one of the original guests at that very first dinner party. She is a seasoned marketing executive for brands such as Athleta, American Eagle, Kate Spade, and Gap. She is now a brand consultant for companies including Anthropologie, The RealReal, and Lulus. Nothing to sneeze at over here. She is an advisor for Visible Ventures, a pioneering early-stage consumer venture capital firm, and for Nuudii Systems, an innovative intimate apparel brand, which I need to hear more about. She is also a board member for the San Francisco-based handbag company, Senreve and a member of the board, a community of fractional and project-based experts. She's a slouch.
She's also a wife, a mother to two young adults, a friend, a mentor, and a member of my own personal board of directors. She's also my former boss. Fun fact, she and I have traveled the world together through our work and had some wild adventures, including traveling to Kabul, Afghanistan during the war and scaling the Sydney Harbor Bridge in Australia wearing very snazzy blue jumpsuits. I think that was the only time in my life where I saw you actually frightened, and not just of the jumpsuits. She is a brave leader, an incredible marketer, a brand guru, and a devoted and steadfast friend. And I am so deeply honored to have you here to talk to me. Kyle Andrew, welcome to Eat My Words.
Kyle Andrew:
What a lovely introduction. Thank you so much.
Johanna Almstead:
Thank you.
Kyle Andrew:
I wish I could say all the things about you in return because a lot of it is true, and we have been through a lot together. But I'm very honored to be here. I'm very excited to talk to you, as always.
Johanna Almstead:
Thank you so much. I'm honored to have you here. There's so much to talk about. I do want to talk a little bit about your journey and where it began, because it's a little unconventional. You were born in Japan, right?
Kyle Andrew:
Yes.
Johanna Almstead:
How did that come about? Because you are not Japanese. Your parents are not Japanese.
Kyle Andrew:
Yeah, my dad was part of that whole Mad Men advertising industry back in the '60s, and so they moved him around to markets where they thought they needed American help. And so one of them was Japan. And then we moved on to Italy, the Philippines, and Australia. They just kept moving him around. When we ended up in Australia, we loved it so much we stayed. And that's where I did most of my growing up. But yeah, it was because he moved around so much. Yeah.
Johanna Almstead:
Do you consider yourself Australian?
Kyle Andrew:
No, not really. Most of my family is still there, and they all have Australian accents and Australian citizenship, but I haven't lived there since I graduated from college. As soon as I graduated, I traveled, like a lot of Australians do, and then ended up in New York. And I've been in and around the New York area for a long, long time; much longer than I lived in Australia. No, I consider myself American, but obviously I have very strong emotional ties to Australia.
Johanna Almstead:
And you're really just a New Yorker.
Kyle Andrew:
Yes.
Johanna Almstead:
A global citizen, but a New Yorker. How do you think living all those places influenced you? And do you think it helped you in your career as a marketer?
Kyle Andrew:
I do think so, because I do think moving around so much forces you to adapt quickly to different people and cultures and try and fit in and try and get along. And so yeah, I do think that it helped me. It definitely helped me moving around to different jobs, adapting to new cultures of different organizations and the politics and the people. Yeah, I do. There are parts of my life that I wish that I had been in one place for a long time surrounded by old family and friends and having the support. Especially as a young mother; I didn't have my family around me. But overall, I think of it as a positive experience for sure.
Johanna Almstead:
One of the big topics I want to talk with you today about is confidence. And it sounds like maybe that moving around did that for you. You're one of the most confident leaders I know. Cringe. I'm sorry. I know.
Kyle Andrew:
No, no, because when you say it, I get it, but you know yourself a lot of times I don't feel confident. People have told me that they think I'm a confident person, but a lot of times I don't feel confident at all, so it's just funny to hear it from people.
Johanna Almstead:
Where do you think it came from?
Kyle Andrew:
I do think moving around, having to adapt and stand up for yourself probably helped.
Johanna Almstead:
Were you confident as a kid?
Kyle Andrew:
I think so. I don't feel like I've changed dramatically as a person. I went to an all-girls school. I don't know, maybe there was something there. I was a second child; learned a lot from the mistakes of my older sister. I don't know. I really don't know. I'm also a very tall person.
Johanna Almstead:
Yes, you are.
Kyle Andrew:
I'm 5'11". And so I do think that brings with it some level of confidence because you're bigger than most people, even often a lot of men in the room. I don't know. I don't know.
Johanna Almstead:
You literally can own the room. Hello, down there.
Kyle Andrew:
I don't know, I don't know where it came from. I guess I do have to credit my parents a little bit. I don't remember them ever doing anything in particular, I think that they just always... I always felt like I could do anything I wanted. There was no restrictions on me. There was no, "Oh, you can't do that," or, "You shouldn't do that." And I don't know, I think I'm lucky because being perceived as confident is everything-
Johanna Almstead:
A million percent.
Kyle Andrew:
... because confidence breeds confidence. If you feel like other people have confidence in you, you then get more confident in yourself. And I've had the experience. When you and I worked at Kate Spade, I felt like I had the confidence of our leaders and the leadership team, and they said it to me. And so then I just thought I could do what I wanted, and I did it. Subsequent jobs that did not have that level of confidence from leaders either because they just didn't know how to express it or they just had different expectations, I don't know. But in other jobs, I never had that feeling again of, oh, I've got the backing of my team and my leaders and I can go for it.
Johanna Almstead:
I think that was something that was pretty rare and pretty amazing in that culture. You gave that to me. I was thinking about this the other night how I had been on your team, but not directly reporting to you, there was someone in between us, and that person was let go. And I remember you sitting me down in your office and telling me that. And I said, "Well, who's going to run the department?" And you said, "You are." And I said, "What do you mean?" And you were like, "Because I know you can." And I was like, "Well, if she thinks I can, then maybe I can."
Kyle Andrew:
You did. And you did and you did it beautifully for years. You did an incredible job.
Johanna Almstead:
Thank you.
Kyle Andrew:
And so, yeah, I do think confidence breeds confidence.
Johanna Almstead:
Yeah, and it's funny how just something so simple as telling someone that you believe in them can really change how they operate. I think of you... I said you're one of the bravest leaders I know. Did you genuinely believe in all those hard decisions you were making, or were you shaky on them but just did them anyway? Maybe a combination of both?
Kyle Andrew:
Probably a combination. I think I knew in that job that we had to take risks because we had a lot to do and we didn't have a lot of money and a lot of time, so I felt like we had to do things fast and take some risks. And then when some of those risks paid off and we started to see that things were working, then it just again bred more like, well, let's keep going. Let's try these crazy things. And-
Johanna Almstead:
And it became part of the culture to take risks.
Kyle Andrew:
Yeah. And not all of them worked, as you know. But also, again, our leaders, I felt like they were pretty supportive of that. And when something didn't work, it wasn't like we were hauled through the mud and yelled and screamed at, just moved on and learned from it and kept going. It was that culture, I think.
Johanna Almstead:
Yeah, I feel like we had... I don't want to call it a leash, but we had a pretty long leash. We-
Kyle Andrew:
We had a pretty long leash. They were just so busy doing other things. They were like, "Just do it. Just do what you think is right. And we trust you." We've got all these other fish to fry. They were not micromanaging in our business every day.
Johanna Almstead:
I definitely valued that when we were there. I didn't understand how rare it was until I went to other companies.
Kyle Andrew:
Same. The micromanaging I think has gotten worse since then, but I also think that was a very special place and the micromanaging was not an issue at all. But I've been micromanaged by CEOs at much bigger companies. And I've been like, "Why did you hire me if you are in the weeds with me if you don't trust me to do the job?" And that's always been something that I think, and you can tell me, that I have tried to do is not be a micromanager.
Johanna Almstead:
No, you were not a micromanager. You had very high expectations, but you were not a micromanager.
Kyle Andrew:
Yeah, you knew much more about the PR world than I ever did. Why would I try and control what you're doing? As long as we were doing it, we were aligned on the goals, why would I want to get in the weeds on that? Just doesn't make sense to me. Hire the people that are good at their jobs and have some experience, and give them a real clear path and goals and strategy, and then let them do their job.
Johanna Almstead:
Yeah, I think that's another lesson. Now that you say that, that's another lesson that I learned from you and that team is the very clear goal setting and the very clear pointing everyone in the same direction. I feel like that was also a very rare time and place that that all happened. We all were shooting for the same north star.
Kyle Andrew:
Yes, we had a very clear mandate, again, from leadership, and so I think we just knew what we had to do. And if we had different paths to get there, as long as we got there. Whereas other places I've worked, since then there've been so many different goals and different priorities and different mandates from different parts of the organization. I do think a good leader is someone who really gets the priorities right and clear with the team and saying, "This is our main goal. This is what we're doing. Let's all go for it." That's so helpful to teams to know what you're shooting for, what the end goal is.
Johanna Almstead:
Yeah, all ships pointing in the right direction. I think that's huge. And I agree. I've had experiences in other organizations that were like, this one's going this way and this one's going that way. And it's very hard to know where to focus.
I want to talk to you about some of the isms in the fashion industry, sexism, ageism, all the other things. I was saying to someone the other day... And I've always thought this because when we were coming up through the fashion industry, I had friends in finance, I had friends in law or friends in other industries that were more predominantly male, and I always felt like we were protected from gender bias and sexism partially because we were the majority. For the most part, women were the majority of most of these companies, so we weren't usually going up against men for the same jobs. And if they were there, they were in the minority and didn't have a leg to stand on.
But it was interesting for me because when I had children, that was the first time I felt like, I call it motherism, some sort of bias against me the moment I became a mother. And often, that was from other women and other mothers, which was scary. And then I think now, as an older person in the industry, I'm definitely getting a sense of ageism, which I didn't ever feel before. I want to just talk to you about your experience. And did you experience any of those things? And how did that play out for you in your career?
Kyle Andrew:
Yes, I've thought a lot about the sexism thing, especially when the Me Too movement happened. And I think, again, I was very lucky working in the retail fashion business that had so many women as part of it, I never really had any issues with men. Probably some micro sexism, but never anything overt. Nothing that I felt like made me angry or upset or scared. And so I do consider myself lucky, but I do think it's because we are surrounded by so many women and we were lucky to have a lot of women in leadership roles that could be mentors for us.
The motherism, I don't think I experienced it the same way you did I think because when I had my children, I was actually working at Gap in San Francisco at the time, and most of my peers and even some of the leaders were women with children. Most of them were the breadwinners. It was a very unique time, I think unique to Gap. It wasn't unusual to have children. It wasn't unusual to have to deal with things, but most of us had these amazing husbands who either had more flexible schedules or weren't working or had decided to stay at home to help. I think I was lucky because I was surrounded by these women who had children and same struggles and issues that I did, and so I never felt like I could really complain or had anything to... If I had an issue, I could deal with it. And we all had to travel so much back to New York that that's just something that happened.
When I came to New York, back to New York at Kate Spade, I was one of the few who had children. It was quite different. But by then, my children were old enough, I think, that they were starting to be more independent and so on. I don't think I've experienced motherism in the same way maybe as you did. Ageism, for sure.
Johanna Almstead:
And how has that played out for you?
Kyle Andrew:
I never expected it.
Johanna Almstead:
Gob smacked.
Kyle Andrew:
Yeah, which I think probably is true of all of these isms. You don't expect it and you don't expect it to happen to you. And then when it happens to you, you're like, "What do you mean? I'm different? I'm not-"
Johanna Almstead:
But I'm a cool mom.
Kyle Andrew:
Yeah, I'm a cool mom.
Johanna Almstead:
But I'm young. I'm cool.
Kyle Andrew:
Yeah. I had never ever felt like my age was an issue until maybe mid-50s. I'm now late 50s. But yeah, mid-50s I realized, oh, everyone else is younger than me. My bosses are younger than me. And there's definitely a bias towards younger, hungrier, more ambitious, more go-getting people who had a little more patience maybe than me.
Johanna Almstead:
Well, I also think you had the double whammy of that new generation that was coming up was wildly ambitious, wildly entitled, wildly savvy on social media in a way that we weren't. And so it became very old guard, new guard. I feel like there's a little more gray area now, but I feel like, particularly for you, that pendulum was swinging really far in that other direction. All of a sudden, there were people who were 25 and, because they had huge Instagram followings, were becoming editor in chiefs of magazines or becoming heads of marketing departments, and it just felt very strange and scary.
Kyle Andrew:
Yeah, it coincided with a huge shift in marketing. As you know, my core competency and my passion, my love is brand. It's changing a little now. There was a time when that was very unfashionable and not interesting to anyone. Everybody was focused on performance marketing, digital marketing, being able to really show short-term results from the marketing that you did. And I will admit I don't think I did enough to keep myself current. I was more steadfast, no, I [inaudible 00:18:44].
Johanna Almstead:
Digging your heels in.
Kyle Andrew:
Yeah, this is what I'm good at, and I'm not going to... And that was probably a mistake. Not that I think I would've enjoyed that other part of it, but I think I should have maybe been a little more open to it and learned more and gotten more expertise and gotten into it more. But that, yes, I do think because marketing changed so much, the age factor was much more obvious.
And it's interesting because it feels like there's a ceiling in the retail fashion marketing world for women for sure, potentially for men as well. When you hit a certain age, you're just no longer as relevant anymore and no longer as interesting to people. And so I have found it harder to find work harder; harder than I thought. I always took it for granted that I would be able to find another job because I was so successful and I kept going to bigger job, bigger job, bigger job, and then nothing. And yeah, that was quite a shock.
Johanna Almstead:
I think also the culture changed so much, not just the job of marketing. But there used to be a time when we came up in the business when it was all about brand and people's roles were siloed in that you were a brand builder, you were a digital marketer, you were something. And I think now I find it, especially with some of my clients who are startups who are 10 years younger than me, let's say, and they're these founders who are doing everything. They're their own graphic designer and they're their own growth marketer, and they have a much broader... Because they watch a YouTube video and figure out how to be a growth marketer. They're much more of a hands-on, do it yourself, whereas we were like, "Well, we'll hire someone to do that." We have big budgets, and we're used to doing that. I think that's also a big change that I find in the business a lot with my younger startup clients who are like, "Oh yeah, no, no, no, I'll just design that email and send it out." I'm like, "Oh, okay."
Kyle Andrew:
It's interesting, though. I think I've found my niche as a consultant with these younger companies.
Johanna Almstead:
Because they don't know how to build a brand.
Kyle Andrew:
Because they don't know the fundamentals of it. They've developed a new product or idea. They have done a lot of performance marketing. They've realized how expensive that is and how short-term that is without the brand piece. I have found with a lot of these companies that teaching them the fundamentals of how to build a brand is something that they really appreciate and are very grateful for, whereas in the more corporate world, brand is still considered, I don't know, too touchy-feely, too emotional, too whatever. And they've got other bigger priorities and-
Johanna Almstead:
Other metrics.
Kyle Andrew:
Yeah, exactly. I do think these younger companies, at least the ones I've been working with, have been really interested in learning and grateful for the experience.
Johanna Almstead:
And I think the pendulum has swung back a little bit more towards the middle where it was growth marketing doesn't matter about the brand messaging, it just is like go, go, go, go, go. And then a lot of those companies failed. Or we've had the girl boss movement fall apart or whatever it is, and now people are like, "Oh, I think I need both. I think I need a brand story that's real and rich, and then I also need this growth marketing and funnel and all the things."
I want to touch on something that you mentioned already before about your time at Gap that you said that you were the breadwinner in your family. And it's something that I've always admired about you because you seem to have navigated that dynamic quite beautifully. And I remember you telling me a story that basically before you married your husband, who is a research biologist and conducts super important scientific research on spiders, that he said to you, "Are you sure you want to do this? I'm never going to make a lot of money. It's all going to be on you." And you said, "Yeah, I'm okay with that." And I remember being like, "Wow, did she really mean that?" And has that ever come back to bite you in the ass?
Kyle Andrew:
Yeah.
Johanna Almstead:
And how did you navigate it?
Kyle Andrew:
We were dating at the time, and I was still pretty young in my career, but I was sadly, even though he's a PhD from Yale and is the smartest person I know, I was already making more money than him. And he said, "You're always going to make more money than me, just so you know." And of course I was like, "Oh yeah, sure. Why? That's fine. I don't care." Not knowing that's a big thing to sign up for.
And yeah, I mean in the end, has it worked out? Absolutely. Absolutely, I wouldn't change it. But you're right, I don't think I knew what I was signing up for. And I definitely had moments throughout our marriage where I was like, "Why is it always me? Why am I the one who has to? I'm exhauste.d I'm done. I don't want to do this anymore, or I want to just take the pressure off a little bit," and there wasn't that option. It wasn't all smooth sailing; there were definitely some moments. But in the end, the only reason why I could have the career that I had is because he was able to be flexible, was able to do a lot of things with the kids and look after the kids, especially when I was traveling so much. And so it balanced out. And now he is still working at the same job that he had when I met him, and he has insurance and he has pension.
Johanna Almstead:
Which is so sexy when you're a consultant.
Kyle Andrew:
So sexy when you're a consultant. In the end, he is providing the stability in a different way than I did previously. But it worked out fine. And I am proud of the fact that we modeled a very different marriage than a lot of my kids' friends. There were plenty of days where I'd be able to go to school pick up for a change, and I was very different than the other mothers there.
Johanna Almstead:
I remember you told me a story how Baz asked you if you could dress like the other mothers.
Kyle Andrew:
Yeah, yeah, that was a highlight of my mother.
Johanna Almstead:
And what did that mean? That meant not wearing work clothes, that meant wearing Lululemon leggings or something?
Kyle Andrew:
He was talking about... I had put him in dance class, and normally the nanny would pick them up from there. And one day I came home from working at Kate Spade, and we used to dress up in our Kate Spade finery.
Johanna Almstead:
Like we were going to a cocktail party.
Kyle Andrew:
With the colors and the heels and the jewelry and everything. And we were going to go out for dinner, and I said, "Okay, let me just change." I changed. I put on jeans and a T-shirt and whatever. I came down the stairs, and he said, "Oh, now you look like a real mother." It was a dagger through the heart because I, of course, always had guilt about not being a real mother, and here's my 11-year-old son saying essentially I wasn't. And so he saw how upset I was, and he quickly was like, "Well, when I get picked up at the dance class, all the other mothers are wearing Merrell shoes and they're in jeans and they're giving out snacks, and so that's what you look like." And I was like, "Okay, we got to stop talking about this because-"
Johanna Almstead:
You're like, "Just quit while you're ahead." Or not ahead, but quit now.
Kyle Andrew:
I think, especially for my daughter, I'm glad that she saw, A, that I was working, whereas my husband works, but he's at home a lot and he's the cook in the family. He cooks every meal. We had a very different looking marriage than I think a lot of their friends. And I think that's a good thing just to have differences, to see that there are different ways of behaving.
Johanna Almstead:
Yeah. I've had moments where, since we've moved out of the city and I've adjusted my work schedule where I try to be with my kids in the afternoon, I try to take them to school, and then I get all the work done in between while they're at school, and then 80% of the time try to be the person that picks them up and takes them to their after school stuff. And I've had moments where I was like, "They probably don't have any idea that I have a job." And then they actually have said it. The other day, I was super stressed and I had a lot going on, and I was like, "I have a lot of work to do." And my little one goes, "You have a job?" I was like, "Oh my God, what do you think I'm doing all day? What do you think I'm doing all day?"
Kyle Andrew:
They want to make sense though because they're out of sight, out of mind and they're busy doing their thing and they're not thinking about you. Yeah, yeah.
Johanna Almstead:
And I'm like, "Do you know how hard I worked to be able to be here and have a job? Do you know?" And they're like, "Well, all the other moms, they don't have jobs." I'm like, "Right." Yeah, it's hard. And they only know what they see and they believe what they see.
Kyle Andrew:
Yeah. If I could say anything to my younger self is stop feeling guilty. Don't feel guilty. And I think I can only say that in hindsight because my kids, knock wood, have turned out to be decent.
Johanna Almstead:
The proof is in the pudding. You've got fully formed humans. I'm still in experimentation mode.
Kyle Andrew:
And I can see that they're good kids and they're going to be good adults. And I've made 1,000 mistakes; more than 1,000 mistakes, I'm sure. But I wish that I hadn't beaten myself up so much about it because they're fine. They're good.
Johanna Almstead:
They're fine. Yeah. Why do you think we beat ourselves up? Because that is something that I didn't really... I guess you just don't know what you don't know until you have kids. But I did not fully understand the level of emotional torture it would be to be a working mom. I didn't anticipate that. I thought I'd be good. I was like, "I love my job, I love working. I'm going to do this. I'm going to balance it. It's going to be fine. They're going to be cared for." And the tug, the pull inside is so deep. Why do you think that is?
Kyle Andrew:
I think it's just still so entrenched in our culture to have mothers be mothers mothering. And we probably, a big part of us, even though we love our jobs and we want these careers, we also want to be there with the kids and see everything and be part of their lives. And so it's interesting. I don't know, I'm always talking to women who feel guilty always. And I try and tell them, "It's not productive. It doesn't make you feel better to feel guilty, better to feel positive about what you're doing and the role model that you're creating for your kids about being a strong woman who's got a great career and is supporting her family." But it's hard, it's really hard.
I remember I was on a business trip in Hong Kong, jet-lagged and whatever, and I got a text or a call from one of the mothers at my son's school saying that I had forgotten that it was green day and my son was the only one that didn't show up with the green clothes. And of course it just killed me. In the end, was it important? When I came back, I apologized to him. He was like, "you didn't even care." Whatever. But-
Johanna Almstead:
But you tortured yourself that entire time while you were in Hong Kong. Yeah. I'm leaving my kids tomorrow for only four days. It's not even a work trip, it's actually a pleasure trip.
Kyle Andrew:
It is.
Johanna Almstead:
The amount of lists and the amount of things, and I'm like, "Oh my God, what if they don't have their shin guards at the field hockey tournament? They're going to remember forever. It was the time their mom went away." It's like, God, stop, just stop.
You spoke about modeling a different type of relationship or a different unconventional family. Did you have a sense when you were younger or did you have a picture in your mind of what having it all meant or what your future looked like? Or you just made that one up as you went along?
Kyle Andrew:
I think I made everything up as I went along. Is there one thing I would maybe want to change? Is I wish I had a better plan. I think I just went. I went, and that worked so I did that and I did this and that and there wasn't really a plan. When I hit this ceiling of ageism and realized I'd have to pivot and do something else, I wish that I had a plan B.
And that's one of the other things that I like to tell younger women. Don't take everything for granted, that it's all going to keep going the way you want it to go. Things happen and things change and unexpected things happen, and so have a plan B. I wish that I had a plan B. It's working out for me, this consultant thing, but I wish that I'd had some other, I don't know, purpose or interest or idea that I could put my energy-
Johanna Almstead:
Dive into.
Kyle Andrew:
Yeah. That would be my only thing. No, but I never planned it, it all just organically happened.
Johanna Almstead:
Yeah, which is interesting because you say that you wish that you had had more of a plan, but I think part of not having a plan is being open to reinvention, being open to metamorphosizing yourself, because I think there are people who are just not open to that at all. And I think that becomes hard because then you're stuck. And then I think it's interesting to think about how we approach our... Do we hit a wall or do we become water and spread around the wall? Do we find our way around these obstacles? Because I think, again, you don't know what you don't know. You don't know what life is going to present to you, so it's hard to have a plan. But is it more about just being open to being flexible and being inspired? Continuing to be inspired, I think that's a big one, right?
Kyle Andrew:
That's true. I don't know how I would've come up with a plan B being a mother and having a serious job. There's no time to be thinking about-
Johanna Almstead:
I'm just going to think about this possible other career I'm going to have, this third career I'm going to have. Yeah, I think it is more about just being like, "Okay, this is where we are now," and not taking it as the end of something, but the beginning of something else, right?
Kyle Andrew:
Yeah. And I do think when I hit this ageism idea, I had decent amount of time where I was like, "Oh, it's done. I'm done. There's nothing left for me to do. I'm just going to stop working and not do anything."
Johanna Almstead:
I remember some of those dinners.
Kyle Andrew:
Yeah. And that was hard. It was really hard. And it took a while, but yeah.
Johanna Almstead:
Well, you're also in a totally new season as a mother. Your children are... One's out of college, one's in college. To have that be happening at the same time as your career transition is happening is a lot of change.
Kyle Andrew:
Well, it is because everyone says your identity shouldn't be about your work, your identity shouldn't be about your children, but it was. Those were two major things. Those were my two things. And my kids becoming adults and moving away and then me not working, all of a sudden I was like, "Who the hell am I? What am I if I'm not those things anymore?" And that was really hard, that was really hard. That was not a period of feeling confident. That was definitely like, I'm old. I'm irrelevant. The people around me who love me love me because I'm this big, strong, powerful career woman, and now I'm not that anymore. What is there left for me to be? That's when I thought, am I not being a good role model for my kids because I'm all of a sudden just sitting at home doing nothing?
Johanna Almstead:
But what if taking a minute is being a good role model? I think we are both products of the grind culture. I remember you saying this to me. Oh, this is funny. I hadn't thought about this. You were talking about your time at Gap when your children were on one coast and you had to travel back and forth to the other coast. And I remember you saying something like, "Well, at least when I'm on the other coast when I'm not with my children, I can go get a manicure or something because when I'm home, I can't do that. There's no way I could take time away from my children to go get a manicure because I'm already away from them however many days a month." I wasn't getting manicures either, don't worry about it, but I finally found someone who would come to my apartment at 10:00 PM and give me a manicure after my kids were in bed. But we were products of this culture that were like, we never allowed ourselves a minute to stop and reflect or rest.
Kyle Andrew:
Yeah, exactly. No, there was guilt around that too, not doing anything. I'm going to get in trouble. From who? Who? This is just me. Yeah.
Johanna Almstead:
Right. And it's funny because I feel like that is something I admire about the younger generations who are learning better, self-care. I hate the word self-cafe. And learning to advocate for themselves better. Or not learning, somehow they've come out of the womb having a better sense of self and a better sense of boundaries and a better sense of what they deserve and a better sense of taking the time. When I'm the boss of them, it's a little bit hard, but when I can step back and be like, "Wow, this is pretty miraculous. Look at them advocating for themselves. Look at them."
Kyle Andrew:
We would never. We-
Johanna Almstead:
Never in a million years.
Kyle Andrew:
We would never.
Johanna Almstead:
I remember a trip, a business trip that one of our colleagues was pregnant on and we were working. That was a really extraordinary trip. We were working 20 hours a day. We were actually just going home to sleep for two hours at a time. And I remember you looking at that person who was pregnant and being like, "At least go home by midnight." What the hell? We were just insane.
Kyle Andrew:
Just as guilty, just as guilty. Yeah.
Johanna Almstead:
Yeah, I was too. I did the same thing. I remember having a moment... I think it was when you were not my boss anymore, but things had gotten a little crazy, and I remember a moment saying to my team being like, "I think we might need to take better care of ourselves. I'm not sure what that means, but I feel like if you guys think of something," knowing that they were going to know better than I was, "come to me and talk to me about it. Should you go take an exercise class in the middle of the day? I don't know." That's just not something our work culture was about, but I had this inkling, this is not sustainable. We're going to burn out.
Kyle Andrew:
Yeah. Well, that's great that you recognized it, and it's great that you said something. I'm sure-
Johanna Almstead:
I don't think I was a particularly inspiring leader in that department, but I tried for a second. It was too little, too late, but I did try for a second. I'd love to know if there was any major pivotal moment in your life that you look back and you think, wow, if I hadn't done that, where would I be? Or if I had done that, if I'd taken that job or married that person or gotten on that plane or... Do you have any moments like that where you think, this is what set me on this trajectory?
Kyle Andrew:
Yeah, I think leaving Australia. I graduated from college, and I was dating someone pretty seriously, and I knew that if I stayed in Australia that I would marry him and that I would have a certain life. And I knew I didn't want that life, even though he was my boyfriend and I loved him, I guess. But I knew I had to get on that plane and travel. I knew. And that's what happened. What I told everyone was that I was going to travel across the US and Europe and then go back to Australia. And I didn't even get to Europe, I got to New York. And I was like, "Yep, this is me. This is it."
Johanna Almstead:
You had never been to New York at that point.
Kyle Andrew:
I had been before traveling with my parents, but I was like, "No, this is the energy I want. This is where I want to be." And I've pretty much lived here ever since. We spent some time in London, we spent some time in San Francisco when I was at the Gap, but I keep coming back to New York. It is my place. And I try to explain it to people, and a lot of people don't get it, but I know I was meant to be in New York. Sometimes I think, oh God, I raised my children in New York. What am I, insane? But again, I am glad because I think they've turned out to be who they are because they live in this amazing city that's incredibly crazy but wonderful at the same time.
Johanna Almstead:
When you landed in New York, how did you go about building a life for yourself? Did you get a job? Did you-
Kyle Andrew:
I was lucky, my godparents lived in New York. And they were in the advertising business, and so my godmother helped me get a job at an advertising agency. And so first part of my career, I was in the advertising agency business like my dad. I just just did what he did. And that set me on my course to be in marketing.
Johanna Almstead:
Wow, that's cool. What is something that you once believed about yourself that you have now outgrown?
Kyle Andrew:
I don't know. I think it comes back to this confidence thing. If you were to ask me, I would never say I was a confident person. I just know I am because people keep telling me.
Johanna Almstead:
If you say it loud enough, someone will believe it. Right.
Kyle Andrew:
And so I never thought of myself as confident. I love it when I hear it from people. And so I think I believe that now because people like you tell me. But I've not felt that way for most of my life.
Johanna Almstead:
That's so interesting. I always say that most of the bad decisions I ever made in my life were because of lack of confidence. And raising two daughters, their confidence is my highest priority. And one it's worked and one I haven't quite figured out yet. I haven't tapped into her intrinsic, deeply held self-confidence. But one, it's wild to see. And I'm like, "Wow, she's going to be okay. She's going to be okay." Because I feel like as young girls and then as young women and then as older women, there's a lot of reasons to start to doubt yourself and there's a lot of people telling you you should doubt yourself. I think that the confidence-
Kyle Andrew:
Confidence is everything.
Johanna Almstead:
It's everything. Yeah. Is there anything in your life that you've said no to that you wish you said yes to?
Kyle Andrew:
I don't think so. I think I've been pretty good at, as you said, taking risks and doing things. And I don't think there's anything I regret. I've made lots of stupid mistakes along the way that I look back at and cringe a little bit, but there's nothing major that I'm like, "Should have done this or should have done that."
Johanna Almstead:
What do you think the best thing about your career has been or continues to be?
Kyle Andrew:
Oh, by far is the network of people that I have around me now. Maybe that's one thing that I wish I'd done better is maybe cultivated it more and understood how powerful your network can be. And people have said that to me throughout my life is, "Oh yeah, you got to keep networking, you got to keep networking." But I don't think I really understood what that meant. What means is cultivating almost a little garden of all these different flowers and people that you can then go to for different things you need throughout your life. And the people that I have met, become friends with, become associates with throughout my career are remarkable people and people that I keep going back to again and again for help, advice, friendship, ideas. It's really the most incredible thing I think I feel in my career are the people that I've met and I've surrounded myself with.
And I would say that's true of all the jobs I've had, but in particular, the people that I met at Kate Spade when you and I were there. Again, there something really magical about that time and the people that were there. But that has been such a resource for me, such a pleasure for me, such a support for me. And I just think there's so many creative, talented people that came out of that company that are just wonderful friends and people I want to stay connected to for the rest of my life and who have helped me, especially in this time where I was a little at sea and I was at a loss. And so many people from that time have come back into my life and helped me and supported me.
And so that is another piece of advice I give to young women coming up is don't neglect your little garden of your network. I know there's not a lot of time to really tend it in the best way possible, but that will be one of your most valuable things at the end of your career or even throughout your career. I think that's one of the most powerful things you can create.
Johanna Almstead:
100%. And I think it's funny because I think when I was in college, I was in fashion school so they talked a lot about networking then, but I think there was a certain time in my life where I cringed at the idea of networking, networking events, and it just felt cheesy.
Kyle Andrew:
Like LinkedIn.
Johanna Almstead:
Yeah, I'm not going to publish articles on LinkedIn. I don't even know how to use LinkedIn still. But I feel like the difference, for me at least, or what made it feel... I don't know if it was a conscious decision, but it was building real relationships, real friendships. And I think having a vulnerability and an authenticity with people, I think it's amazing. You talk about many of our former colleagues at Kate Spade, it's wild how people from that time... That was 10 years ago, 11 years ago, and we left 11 years ago, so the people you worked with 15 years ago will pop up. And it's like we all speak a shorthand, I think, because-
Kyle Andrew:
We had this shared experience. [inaudible 00:43:29].
Johanna Almstead:
... we had this shared experience, but it's also people I genuinely just loved. I loved working with them, I respected them, I was inspired by them. And I think that feels like the difference to me is that you are not collecting people for the sake of collecting them, you're collecting them for the sake of what those relationships add to your life, right?
Kyle Andrew:
Yep. Yeah.
Johanna Almstead:
And how you can help them, you know?
Kyle Andrew:
Yeah, that's actually a really good point because one of my great pleasures is helping people who are in my network, helping them find jobs, helping them connect to other people. That's been very gratifying for me. Especially a lot of the younger women that worked for me over the years, I love being a resource for them. I love making connections, finding people, helping people find jobs, that's very gratifying for me too. Yeah. But it is because it was a shared experience, and we all have a very similar way of doing things and thinking about things and also a very authentic relationship. Yeah.
Johanna Almstead:
It's funny that you say too about the helping other people because I think of a couple... There's only a few, but there's a couple people that I think about who were not that way, you know?
Kyle Andrew:
Yeah.
Johanna Almstead:
Who were much more go-getter, single-minded, ambitious for the sake of ambition for themselves. And I think now those aren't people I would call. Those aren't people I'm inviting onto my podcast. And so it works both ways, you know?
Kyle Andrew:
Yes.
Johanna Almstead:
And I think that there's so many people that... I think I was telling you the other day, the reaction to this podcast has been incredibly supportive. I could call someone I have not talked to in 15 years and they'll be like, "Hell yes, I'll come on your podcast. Of course I will. And then we'll scream it from the rooftops. And how can I help?" And I think there is something so, number one, self-fulfilling in that. I think that those are the same people that are getting helped, right?
Kyle Andrew:
Yes.
Johanna Almstead:
By our network and by people who have influence or access or anything. I do think that's an interesting thing because I think there's some people who think of ambition as being lone soldier. I'm just going to go and do what's right for my career, and I'm going to climb the ladder and kick off whoever's in my way. And I don't think that's how it works.
Kyle Andrew:
No. I do think the lesson for me is learning, as you said, to be vulnerable and to ask for help when you need it. I think I definitely was one of those people who was like, "I got to just do it. I got to do it myself, otherwise I'll look like I'm weak." And became very clear to me that there's strength in people helping each other.
Johanna Almstead:
That's another lesson we can learn from the youngins who are not afraid to ask for help. And they're not afraid to ask for favors, they're not afraid to ask for support, connections, any of it. And I think it's took me watching them to learn the same thing. I was the same way. I was like, "I'm just going to do it myself. I'm not going to tell anyone." And it's like, that doesn't really get us anywhere.
As we said, you're totally in this new season. I feel like it's a world away from where you were when you were my boss. You were raising two small kids at the time and running the marketing department of a big brand. What are you excited about now? Because now it's like you're an advisor and you're a consultant and you've got grown kids, and so what feels inspiring to you right now?
Kyle Andrew:
Well, it's different when you're a consultant. I sit at home all day most of the time. I make sure that I have enough in-person meetings during the week to make me feel like I've got that connection. But I loved working in an office environment because all the places we worked at were so creative and you were surrounded by young, creative people. And I always felt like a little bit like a vampire, like I was sucking the energy and the life and the ideas from these people and got me going. I definitely miss that piece of it for sure.
I do force myself to get out there and try and get that feeling in different ways. I've become a huge fan of Substack. I read so many substacks. I love so much of the writing there and so many ideas and the connections. Honestly, my kids, because my kids are just starting out in the work world, and I love hearing about their lives and helping them, giving them advice. They don't always take it. Let's be honest.
Johanna Almstead:
"Oh, mom."
Kyle Andrew:
Yeah, exactly. But I love seeing them get into the world and becoming these people, so I get excited by that. And then travel has always been something that I just love. As you said, you and I went to some crazy places. I can't even believe they let us go to Afghanistan. It was just-
Johanna Almstead:
I can't either. I was telling someone that story the other day. I dropped it in conversation not really realizing how impactful it would be, and they were like, "What?" And then I told them the story, which we'll talk about on another podcast. We might have to have a whole other episode to talk about that. And they were like, "Your company let you go to war torn Afghanistan?" Yes, they did.
Kyle Andrew:
People with guns.
Johanna Almstead:
Our driver and our shooter. Remember?
Kyle Andrew:
Yeah.
Johanna Almstead:
I had a crush on my shooter.
Kyle Andrew:
Yeah. It's insane. And so that piece of it, going to crazy places. Remember you went to Middle East and rode a camel for one job.
Johanna Almstead:
Was that in Dubai, Abu Dhabi?
Kyle Andrew:
I missed that kind of travel. Again, as many times I can get out in the world and go and experience a new culture and new people, that gets me excited. Yeah.
Johanna Almstead:
Cool. All right, we're going to do my favorite part of this whole thing, which is the lightning round of silly questions. Do not overthink them, because I know you're a very thoughtful person. This is just for fun. No judgment. There's no prize at the end. You just get to answer silly questions that I like to ask. Favorite comfort food?
Kyle Andrew:
Shrimp tacos.
Johanna Almstead:
Oh, that's a new one. What is something you're really good at?
Kyle Andrew:
I'm a good shopper. If my daughter needs something for an event or something, I'm very good at finding exactly what she needs.
Johanna Almstead:
That is so not what I would've thought you would say, and I love that. What is something you're really bad at?
Kyle Andrew:
I'm just not a very patient person. Anything that requires having to learn a set of rules and then put them into practice, I'm terrible at games, for example. I like learning all the rules of a game and then having to go through that, I'm terrible.
Johanna Almstead:
Yes. Favorite word.
Kyle Andrew:
And.
Johanna Almstead:
Ooh, I like that one. Least favorite word.
Kyle Andrew:
No.
Johanna Almstead:
Okay. Least favorite food? Deal breaker. Because I know you eat a lot of things, you're very adventurous, but no way you are not eating it.
Kyle Andrew:
I don't like any of those innards like liver or brains or anything like that. I don't think I can do that.
Johanna Almstead:
Okay. Do you have any hobbies?
Kyle Andrew:
Not really. I am a prolific reader. I read a lot. I really use reading to escape. I would say that's my hobby, if that counts. Yeah.
Johanna Almstead:
Me too. I hope it counts. It's the only one I got. Best piece of advice you've ever received?
Kyle Andrew:
I think it's not one piece, but I think in general, what we talked about, don't be so hard on yourself, don't take it so seriously. Things change, things are different. It feels terrible now; it won't feel so later.
Johanna Almstead:
Don't beat yourself up.
Kyle Andrew:
Don't be hard on yourself. Yeah, don't beat yourself.
Johanna Almstead:
Easier said than done. If your personality were a flavor, what would it be?
Kyle Andrew:
I think maybe like a matcha. I don't think I'm-
Johanna Almstead:
Ooh, maybe like a matcha. That was so cute.
Kyle Andrew:
I'm not super sweet, but I don't think I'm bitter or twisted or whatever, so I think I like a matcha or-
Johanna Almstead:
You're secretly strong but frothy on top.
Kyle Andrew:
Maybe it's my Japanese birth thing that's coming.
Johanna Almstead:
Oh, it's coming full circle. Matcha in your veins actually from your being born on Japanese soil. Okay, last supper. You're leaving this earth. What would your last meal be?
Kyle Andrew:
Peking Duck.
Johanna Almstead:
Ooh, fun. And what would you drink with your duck?
Kyle Andrew:
Probably a nice red wine. Yeah.
Johanna Almstead:
Okay. Have you had any moments in your life when you've had to eat your words, when you've had to be like, "I was wrong or I shouldn't have said that"?
Kyle Andrew:
Oh yes, many times. I'm trying to think if I can give an example. I can't think of anything right at the top of my head, but yes, that's happened to me a lot. Yes. And that's moments where I'd lie in bed at night and remember something I said to my daughter when she was five or something about what she was wearing. "You can't wear that. You look terrible." Why? Who cares? Who cares what she put on? Who cares? Why would I even want to say that to my daughter? Yes, there's plenty of times I've said something and I've regretted it.
Johanna Almstead:
I was going to say I feel like parenthood has really been an experiment in that for me, and I'm trying to learn to take it back as soon as I realize it. I'm trying to be not proud about it and go back and say, "You know what? I really shouldn't have said that." If you could eat only one food for the rest of your life, you have to eat it three meals a day for the rest of your life, what would you eat?
Kyle Andrew:
I think bread, like a baguette. I could eat that for-
Johanna Almstead:
So versatile too.
Kyle Andrew:
Exactly.
Johanna Almstead:
What is your happy place? Or where is your happy place?
Kyle Andrew:
Oh my God, any beach anywhere. Grew up in Australia, so I'm a beach person. Just put me on a nice piece of sand with some nice water and I could be there forever.
Johanna Almstead:
What do you wear when you feel like you need to take on the world? What's your power outfit for your own power?
Kyle Andrew:
I think anything that makes me feel confident would be something that I feel like makes my body look good, right?
Johanna Almstead:
Mm-hmm.
Kyle Andrew:
I don't know if you remember, I have this dress, it's a black Jil Sander dress. Do you remember that dress?
Johanna Almstead:
I was about to say is it black?
Kyle Andrew:
Yes. I still have it, and I haven't worn it in a while, but-
Johanna Almstead:
It's a sexy dress.
Kyle Andrew:
It's a really sex... But it's not sexy, meaning it's not revealing.
Johanna Almstead:
No, it's not revealing, but it is gorgeous.
Kyle Andrew:
But it's got big shoulders and a small waist. It just makes me feel like a boss lady. Yeah.
Johanna Almstead:
What's the most memorable meal you've ever had?
Kyle Andrew:
I've had lots of memorable meals. I think one that comes to mind is my husband and I were in Italy and we went this tiny, little restaurant we hadn't heard of. This was before Instagram told you where to go. We just walked into a place in Pisa and had a dish that I don't think we knew exactly what it was, but we ate it. It was incredible. It was spaghetti a lardo, lardo being the fat, you know?
Johanna Almstead:
Mm-hmm.
Kyle Andrew:
And spaghetti sprinkled with bits of fat. And I would never have eaten that if I knew what it was, but it was so delicious. And we both looked at each other like, oh my God. It was just-
Johanna Almstead:
Mind-blowing.
Kyle Andrew:
Those moments we were like, "Okay, we love this country, and we were going to keep coming back to this country and eating this food because it's crazy."
Johanna Almstead:
Yeah. Turns out pasta with fat on top is delicious. What's your go-to coping mechanism on a bad day?
Kyle Andrew:
I do think reading for me is a total escape. Whether that's reading a novel or reading a great article or something, that for me is escape; just block out all the horrible stuff and get into this really interesting story or idea.
Johanna Almstead:
Okay. What is your dream dinner party guest list? You can have as many people as you want since it's a dream.
Kyle Andrew:
I don't know. I would want it to be a mix of artists and fashion designers and people in culture, but I'd also want to have... I just would be really curious, what are all the cool people doing? I want to just hear them, have a conversation. I want to hear. Because I feel like I'm out of that world, especially these days, and so I'd just want, for example, Sofia Coppola. I think she's so cool. I would love to hear her.
Johanna Almstead:
I love her.
Kyle Andrew:
Miranda July I think is such a cool person. I would love to just be listening to her.
Johanna Almstead:
Man, that would be a dinner. Did you read All Fours?
Kyle Andrew:
You know what's funny? I started it and I have not finished it.
Johanna Almstead:
Really?
Kyle Andrew:
A lot.
Johanna Almstead:
It's a lot.
Kyle Andrew:
And I [inaudible 00:55:23]-
Johanna Almstead:
It's intense.
Kyle Andrew:
I started it when I was going through this weird time in my life where, again, I didn't really know who I was or what I was doing, and I think it made me feel worse.
Johanna Almstead:
A little too close to home.
Kyle Andrew:
Maybe. Yeah. I think I need to revisit it now that I'm in a bit of a better place. But I love her. I think she's incredible. And I know this book has changed people's lives and has opened up amazing conversations, but I don't know, it wasn't the right time for me.
Johanna Almstead:
Timing is everything. I feel like I was a little bit shell shocked by it because I hadn't read anything about it. I didn't know anything, and I bought it right after it was released. And I love her, and so I just was like, "Oh." And I read it, and I was like, "Whoa, that was not what I was expecting at all." Yeah, you have to be ready. It's a lot.
Kyle Andrew:
Yeah, I have to go back to it.
Johanna Almstead:
What is one thing for sure right now in this moment?
Kyle Andrew:
I know for sure things are going to be fine. Things are going to work out. I hate reading the news and I get so anxious about what's going on in the world in this country right now, and I have moments where I'm like, "Oh my God."
Johanna Almstead:
What are we going to do?
Kyle Andrew:
Yes. And then you'll send one of your things. Sometimes it makes me feel worse or sometimes better, depending what you-
Johanna Almstead:
I'm trying now only to send ones that make people feel better.
Kyle Andrew:
But I think in the end, I'm an optimist and I do believe in the power of positive thinking, and I do think things will be okay. They may be different, they may be not what you wanted or expected, but I do think things generally work out.
Johanna Almstead:
I love that. I think that's a really nice note to end on. Do you have any last little morsels of advice for our listeners?
Kyle Andrew:
I just think, especially for young women in their careers, I have a lot of women who still reach out to me and say, "Thank you for being mentor. Thank you for being understanding, for showing me that you can do both the mother and the work side of this," when I didn't even realize I was doing it. "Thank you for being a role model," when I didn't even realize-
Johanna Almstead:
You didn't set out to be a role model necessarily.
Kyle Andrew:
No, I didn't. And I didn't know I was doing it. And again, if I'd known that, maybe I would've done something differently. But anyway, at least I have enough people who say I did a good job that I feel, okay, good, great. But I would say to anyone is find a good role model in your life, find a mentor. Find someone who you can talk to about your life and your career and your struggles and your guilt, because I think talking about it with people who are in the same situation as you is so helpful. And people say having it all doesn't make sense anymore and it's not a goal, but I do feel like I have been lucky. I have had a lot. I don't know if I had it all, but I had a lot, and I feel pretty good about it. And I think you can try and have a lot. It's okay if you want to try and have a lot. [inaudible 00:58:17].
Johanna Almstead:
It's okay to try. Yeah.
Kyle Andrew:
You can do it.
Johanna Almstead:
I love that. This has been an incredible honor and a big full circle moment for me. I was thinking about that as I was thinking about you gave me some big chances in my life, you took some chances on me, and so it's really an honor to have had you here and to listen to your wisdom and your encouragement and your advice. And I hope our listeners know how lucky they are to be able to have had this hour with you. I'm eternally grateful. And thank you so much for being here.
Kyle Andrew:
And thank you for having me. I'm very honored. And it makes me feel great that someone that I worked with wants me to talk about myself. I'm very grateful for that. Thank you.
Johanna Almstead:
Thank you so much. Well, that was super fun. Thank you all for joining us. I'm so grateful that you guys keep tuning in and listening to our stories. If you've enjoyed this episode, please, please, please follow the podcast, subscribe, like it, share it, comment on it. Please send it to any of your friends who you think might like it. We are actively trying to build this community so that we can just keep sharing our stories with one another, keep inspiring each other, and keep supporting each other. As always, thank you so much for being here.