Her Daughter Called Her Out… and It Rewired Her Leadership

DEBORAH PALMER KEISER, CHIEF OPERATIONS OFFICER PAIR OF THIEVES

Episode Timeline

0:00
INTRO & GUEST
BACKGROUND
02:40
FROM GLOBAL BRANDS TO
COO AT PAIR OF THIEVES
10:03
PRIORITIZING CAREER: THE COST
OF BEING A PROVIDER
23:39
WHAT GLOBAL CULTURES TEACH
US ABOUT WORK-LIFE BALANCE
33:01
MY FEARLESSNESS: A TOWERING
STRENGTH & HIDDEN LIMIT
38:44
TAKE YOUR DREAMS ALL THE WAY
ADVICE FOR PROFESSIONALS

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Show Description

In this raw, honest, and deeply reflective conversation, Kevin Rice sits down with Deborah Palmer Keiser, global operator, supply-chain builder, fear-tamer, and now COO of Pair of Thieves, to explore the cost of ambition, the courage to repair, and the surprising ways our kids teach us to lead.

Deborah spent three decades opening markets, fixing broken supply chains, and resurrecting brands across the world, from Gap and Williams-Sonoma to Victoria’s Secret, AllSaints, Boardriders, and Yeezy. She built a reputation as the operator companies call when it’s time to grow up and get serious. But behind the promotions, global travel, and relentless execution was a young daughter quietly taking inventory of all the moments her mom missed.

The turning point came when seven-year-old Tilly asked to see the family’s bank balance, not because she cared about money, but because she wanted to know why her mom kept choosing work over her. That one question cracked Deborah open. It sparked a five-year process of repair, reconnection, and relearning how to sit still long enough to paint nails, draw pictures, and rebuild trust one quiet moment at a time.

Deborah shares how being fully present with her daughter made her a better leader, more human, more honest, and more clear about her limits. She explains why becoming “truthfully unavailable” actually strengthened her teams, empowered emerging leaders, and deepened commitment across her orgs. And she reflects on what her daughter taught her about emotional articulation, empathy, and creating space for others to be fully themselves.

Together, Kevin and Deborah explore what it means to raise a young artist in a world that pushes safe careers, why fearlessness can be both a gift and a trap, and how childhood instability shaped Deborah’s early beliefs about success, security, and motherhood. They talk about global cultures that integrate family into daily life, and what America gets wrong about excellence, work, and worth.

This is a conversation about the long road back to connection, the humility of repair, and the kind of leadership that grows not from ambition, but from love.

In this episode, you’ll learn:

  • Why a seven-year-old’s question about money became Deborah’s wake-up call
  • How to repair a parent–child relationship after years of distance
  • Why presence, not provision, is the foundation of trust at home
  • How becoming “unavailable” at work actually made Deborah a stronger leader
  • What global cultures teach us about integrating family into professional life
  • How fearlessness can morph into self-isolation and what breaks the cycle
  • Why dragging people uphill fails and how servant leadership changes everything
  • How childhood instability shaped Deborah’s early beliefs about success
  • What it means to raise a young artist in a world obsessed with productivity
  • Why taking your dream all the way is the antidote to lifelong regret

Top Takeaways:

  • You can provide for your kids and still lose connection with them. Repair requires presence, not perfection.
  • Kids often tell the truth adults avoid. Listening to them takes courage, but it changes everything.
  • Leadership rooted in humanity invites teams to step up, not step back.
  • Your greatest strengths, fearlessness, independence, self-reliance, can become your greatest limits if left unchecked.
  • The stories we inherit from childhood quietly shape every decision we make as adults.
  • Openness builds trust. Pretending to “hold it all together” builds distance.
  • Culture is people. People stay (or leave) because of who you are, not what you produce.
  • Every path is hard. You might as well choose the one that makes you feel alive.
  • Taking your dreams seriously is an act of courage and self-respect—and the same is true for your kids.

Episode Transcript

Deborah Palmer Keiser (00:00)
she would ask me to tell her our bank balance.

What she was trying to understand was, why am I choosing work over her? if we had enough money in the bank, Why was I not choosing her?

I missed a lot of my daughter’s first, not only working and building a career, but I traveled like a crazy person.

I honestly, naively thought that’s fine. There’s a parent at home. when she got to about seven, she let me know that I was wholly unacceptable.

that took about five years.

for me to earn my space back.

I had to sit there and whether it was painting our nails or drawing, I had to only do that. it feels really…

disorienting to sit calmly focusing on one thing with one person.

Being truthfully unavailable I think, made me more human to people who worked with me and actually let them step into the ring

and they would rise to the occasion

what my daughter’s wisdom has taught me is to really open up and realize that everybody is going through the same moments of aggravation, moments of insecurity, moments of joy, and to open yourself up to allow people to share that with

Kevin Rice (01:00)
you

Kevin Rice (01:28)
Welcome back to CEOs and ABCs. My guest today has spent three decades turning messy global supply chains into engines for growth. From Gap to Williams Sonoma, Victoria’s Secrets, All Saints, Yeezy, Board Riders. Deborah Palmer-Kaiser built her career by saying yes to the hard stuff. New markets, turnarounds, flatlines that needed a second life. Today, she’s the COO at Pair of Thieves. She’s the operator brand’s call when they’re ready to grow up,

tighten the seams and still keep their soul. But this isn’t just a story about operations. It’s a story about a seven-year-old girl in Paris asking to see the family bank balance, not because she cared about money, but because she wanted to know why her mom kept choosing work over her. Deborah spent years as a primary breadwinner because she believed stability, a roof, and a steady income was enough. Her daughter, Tilly, eventually made it clear they were not.

We talk about raising a young artist in a world that wants safe careers, and why Deborah now tells her daughter to take that dream all the way,

and what it looks like to shift from dragging people uphill to leading as a servant, both at home and at work.

This is a conversation about fearlessness, repair, and choosing presence over perfection.

Kevin Rice (02:40)
My guest today is Deborah Palmer Kaiser.

Kevin Rice (02:42)
thank you so much for being here.

Deborah Palmer Keiser (02:44)
Thank you. Happy to be here.

Kevin Rice (02:45)
Yeah,

I appreciate you making time during the Thanksgiving break. I know it’s like a busy time of the year for all of us. So I really appreciate you being here.

Deborah Palmer Keiser (02:54)
Thank you. Yeah, I appreciate it.

Kevin Rice (02:57)
We got introduced through Arne Arens who is one of our previous guests here. And, you guys worked together while you were at Boardriders And as I got to know you and understood the incredible career you’ve had, you’ve led in the C-suite across some of the world’s greatest retail brands from Gap to Williams Sonoma. I know you did a stint at Yeezy, you know,

What does kind of life look like today for you?

Deborah Palmer Keiser (03:23)
That’s a really good question. ⁓ I have worked across brands from size and scale to product categories. These days I focus on mid-sized brands where I can act as mentor, advisor, as well as hands-on operations. So I think a lot of my career was pushing water uphill with a rake.

I would describe it that way, of either trailblazing, opening up markets, the retail industry in the last 30 years has grown remarkably, truly globally, but remarkably in terms of commercial access and markets. So a lot of my earlier career was honestly trailblazing and bushwhacking. And now I spend more time

Kevin Rice (03:43)
Mmm.

Deborah Palmer Keiser (04:07)
in the retail environment today, taking from what I’ve done, what I know, by trying to coach and mentor young professionals who haven’t had or didn’t have the benefit of growing up in the trenches, so to speak. I am of the generation that worked with and in factories in America. I’m of the generation who took sewing class in school, home ecs sewing.

So I feel like I have a great advantage because I understand the very visceral essence of operations and supply chain where for a lot of young professionals today or mid-career professionals, it’s in the abstract. It’s that manufacturing is overseas, logistics happens out there, there’s a big port, but it’s a lot in the abstract. And so I spend a lot of time trying to bring it in and home.

And so people really understand what they’re, the work that they’re doing.

Kevin Rice (05:02)
And you’ve taken that experience and you’re now at Pair of Thieves, which is a brand that I’m intimately familiar with, if you get the phrase. Tell us about that decision to join Pair of Thieves.

Deborah Palmer Keiser (05:09)
Excuse the pun.

Well, I first of all, am an underwear fanatic. I’ve not worked in men’s underwear so much, but I’ve worked in women’s lingerie, earliest days with Victoria’s Secret. And then I had founded my own lingerie brand when I lived in Europe as well. I’m a big believer that if you feel good in your underwear,

you likely are going to feel good for the rest of the day. that’s the first thing you do. It’s the closest to your body. And if one were to have to dress down, you don’t want to be embarrassed in your underwear.

the founders of Pair of Thieves, they are looking to get back into growth mode. And so that’s when I usually join companies, when there’s either a

a flat line or a turnaround or something where there’s heavy lifting to be done. That’s usually when I come in because oftentimes, operationally, a company will be fragmented or stalled out, and that’s where my expertise is. So I’m happy to be both in the lingerie world, underwear world, and doing what I do best.

Kevin Rice (06:17)
That’s amazing. based on Los Angeles?

Deborah Palmer Keiser (06:20)
They’re based in Los Angeles, I’m in Northern California, but my daughter is living in LA too. So I got the added benefit of playing in underwear and seeing my daughter.

Kevin Rice (06:32)
That’s amazing. How old’s your daughter?

Deborah Palmer Keiser (06:33)
she’s 24, she’s in music school in LA and she’s gigging. usually I’m down there almost every week and I usually get to see her every week and gigging at some little music club or bar in LA.

Kevin Rice (06:48)
That’s

I’m always curious, how the relationship evolves as our kids get older. what is your relationship like with your daughter? now that she’s kind of entering into young adulthood?

Deborah Palmer Keiser (07:00)
I learn a lot from my daughter. She is a deep empath. what I have found remarkable about her as long as I’ve known her is that she takes her observations, her feelings, and she articulates herself very well in the moment.

I stuff stuff down, you know, I’ll deal with it later. I’ll I’m not going to make a situation awkward by commenting in that moment. Tilly finds the apt words in the moment to honestly express herself and leave space for the other person to

respond and understand and express themselves. even yesterday we flew from New York and New York airport was not a happy situation. of course, mama wound up instantly in an airport and my daughter was kind of doing cleanup after me. She would go and talk to the people and she would explain, is what happened. This is why my mama is reacting that way.

perhaps I would suggest that you could do X, Y, Z, and she would close it all with, ⁓ but we love you and walk away. she’s a really feeling person who leaves room for other people’s feelings. And so my relationship with her right now is very much learning how to process my own emotion and share them for the…

betterment of those I’m around. maybe being female, maybe being of my generation, especially professionally, I feel like the untold lessons were show up, suck it up, work hard, never let anybody see you crack, never say you can’t do anything. So there was a cactus coat that I wore where

It was a real facade of holding everything together. And because I thought the alternate was completely falling apart. And

what my daughter’s wisdom has taught me is that to really open up and realize that everybody is going through the same moments of aggravation, moments of insecurity, moments of joy, whatever it is, and to open yourself up to allow people to share that with

Kevin Rice (08:57)
you

Deborah Palmer Keiser (09:14)
that actually builds connection. Even in moments of frustration, it builds connection. it’s been truly eye-opening for me. My daughter makes me much more emotionally wise.

Kevin Rice (09:16)
Mm-hmm.

That’s amazing. I have many similar experiences. I very much kind of was closed I kept a lot of my personal life close to the vest. I showed a public perception that everything was going great when in reality, like behind the scenes, my personal life was not. I think that was what I learned from

Deborah Palmer Keiser (09:36)
Mm-hmm.

Kevin Rice (09:47)
not only my parents, but also society. And there’s kind of this new wave of encouragement to be more expressive and open and honest and candid about what’s going on in your personal life. And, our kids are a great mirror to learn those kinds of

Deborah Palmer Keiser (09:57)
Mm-hmm.

Kevin Rice (10:03)
was your relationship with your daughter always this way?

Deborah Palmer Keiser (10:05)
No, no, I think I assumed the role of provider. So I was the primary breadwinner in the family. My husband chose to be at home papa. he’s a freelance creative. So, you know, there’s a little bit of an assumption of, you can do what you do anywhere, which also was a little daft on my part, but he wanted to be at home papa.

And I thought, okay, this is perfect. I provide, he caretakes, she thrives, and everything’s perfect, yay.

And I missed a lot of my daughter’s first, not only working and building a career, but I traveled like a crazy person. So I would be gone two weeks, three weeks at a time, and repeatedly, just constantly. And because I’ve had global organizations, it wasn’t necessarily destination travel for work. It was…

I live there for a period of time and then I go to another location to live. And I thought it would be destabilizing to drag my family around. And so I’ve spent pretty significant periods of time away. So I missed a lot of my daughters first, but I honestly, naively thought that’s fine. There’s a parent at home. when she got to about seven, she let me know that I was wholly unacceptable.

Like she was kind of taking tabs on how much I missed. She told me I was not listening to her when she asked for time. At the time I had, it was before our phones were as sophisticated as they are, but I had three phones depending on which continent, because I managed between three continents. And I was pretty much 24 seven all the time. So I would be with her, but I would always have a text or an email or a phone call or something going on.

Kevin Rice (11:19)
you

Deborah Palmer Keiser (11:45)
And it took me a while to hear her message, but I did not have a relationship with her. I was kind of a mom by function, but I left a lot of the intimacy and the closeness to be had between her father and her. So I’ve had to earn it because

She just would not spend time with me if I wasn’t gonna put everything down and pay attention to her. Which my analogy is riding a bike a hundred miles an hour down a hill into a sand pit because

I had to sit there and whether it was painting our nails or drawing, I had to only do that. And I think we got so used to this frenetic being pulled in all directions that it feels really…

⁓ disorienting to sit calmly focusing on one thing with one person.

And at the time, one person with whom I didn’t really have a dialogue or a rapport, had to get to know her. But she was pretty clear. I had to earn her trust. I had to earn her intimacy. I had to show up in a way that was convincing to her. And

Kevin Rice (12:35)
Mm-hmm.

Deborah Palmer Keiser (12:50)
that took about five years.

for me to earn my space back. And once I started to understand that, I was determined to never let it go.

It had to be my commitments myself as much as my commitment to her. But I realized how much I had been missing earlier on. But I attribute the recognition to her wisdom.

Kevin Rice (13:08)
Yeah.

I mean, I certainly relate to that. in my career, I was traveling a lot. I was working long hours. I had become a single parent myself and so I was the breadwinner and I figured as long as I was taking care of the kids, they had a roof over their head. They were fed that was doing my job. but I had quite a few moments where my

Deborah Palmer Keiser (13:26)
Mm-hmm.

Kevin Rice (13:33)
three and a half year old, he couldn’t verbalize what he was experiencing, but through his behaviors, I could tell there was a huge rupture and disconnection between our relationship. And it later materialized in their behavior and their inability to listen to me and their defiance. And it makes sense, right? I wasn’t around,

Deborah Palmer Keiser (13:52)
Mm-hmm.

Kevin Rice (13:54)
as much as I would have liked to be because I was prioritizing my career and what I thought my role needed to be. so when I came home from work and I told them it’s time to make their bed or clean their room, like, why would they listen to me? We weren’t connected. that’s a big part of like, the dynamic of parenting is like, if you’re not connected, why would you have all these expectations of them? I’m curious, uh, were there any

Deborah Palmer Keiser (14:07)
yeah.

Kevin Rice (14:16)
key turning point moments for you. It sounds like your daughter was very clear, which is incredibly impressive for a young woman to be able to articulate that to her mother. But were there any moments that really stood out to you where you’re like, I need to make a change?

Deborah Palmer Keiser (14:33)
An odd period, she would ask me to tell her our bank balance. was like, yes, how much money do we have in the bank?

I was like, that’s a really weird question. We have enough money to live. No, I want to see how much money. And at the time, it was during the seven, eight-year-old period. At the time, I think the number would have been abstract, it took quite a lot of debating with her,

What she was trying to understand was, and what trying to get clear from me was, why am I choosing work over her? And if we had enough money in the bank, why was I choosing that? Why was I not choosing her?

And I think it was over the course of three months of kind of battling over

Why does she want to know how much money we have? just as you said, she’s got a roof over her head. She’s got everything she needs. And what she was trying to understand what was better about that than her. that was a big turning point for me because I realized, first of all, kids are not as dumb as as we treat them as being. So of course, my daughter would feel like I was choosing work over her, because that is what I

have to doing on a day-to-day basis over and over again willingly, enthusiastically, and I was not doing time with her and spending time with her and planning time with her. There’s a level of wisdom in that. What you do is more important than what you say. And I realized at that point that I had to demonstrate through action what both my intentions and my wants were.

So if I said, no, Tilly, I’ve just got to take this trip. I’ve got to take this trip. She’s like, do you really? I mean, do you really? What’s going to be solved? So on the one hand, I had to start speaking in different language. I want to take this trip because this is what I’m going to do. This is what I’m going to get out of it. And when I come back, yeah, yeah. And when I come back, I want to spend this kind of time with you. I will commit that time.

Kevin Rice (16:25)
And that’s more honest. Yeah.

Deborah Palmer Keiser (16:33)
Ironically, I studied linguistics in school. The linguist in me started coming out realizing, I have to use words that actually convey meaning, not just throw these words out to a kid and say, that’s good enough. She’ll understand. I’ve got to do this. Because what she saw was I was making choices and I was not choosing her. That was a big turning point. But it started with a bank balance.

Kevin Rice (16:58)
Wow. That’s a, like you said, it’s an incredibly insightful thing for a young woman of that age to be thinking about. And it would have taken me a bit to connect those dots, to figure out why she’s, why she’s asking. I’m curious when you did make that decision to be more conscious and, have more intention in your relationship with your daughter, what changed in your work in order to be able to facilitate you

Deborah Palmer Keiser (17:05)
Yeah. Yeah.

Kevin Rice (17:23)
repairing the relationship.

Deborah Palmer Keiser (17:25)
Um, so I’ve had the benefit of being a senior leader for a very, very long time. I’m kind of an alpha dog personality. So at a very young point in my career, when in doubt, if nobody’s taking charge, I’ll take charge. It’s less about the title. it just is my personality. I like to get stuff done. I’m organized. I can see what has to get done. And I am physically, mentally and emotionally willing to step out and do it.

When I had to reorganize work, what I realized is it also enriched the relationship I had with people on my team because I became the type of leader who didn’t ghost people. I just wasn’t not available. I would let people also know what I was doing. Hey, you guys, when I get home, I’ll be working.

these days, but I’m cutting off at four because I’m going to go off and do stuff with Tilly or I would have lunch with my daughter and I would block that out.

Being truthfully unavailable I think, made me more human to people who worked with me and for me and actually let them step into the ring and say, okay, we know exactly where she is.

And we know that stuff has to carry on and they would rise to the occasion either to have my back if something happened or to step in and just start taking charge of things. It opened up a whole new thought bubble in my career and my leadership style because I saw people willingly want to step up.

And for them to understand that, again, I didn’t have a side gig.

sleeping, I was spending time with my kid and I really loved my kid and they would get to know Tilly as well. I think built a tremendous amount of trust and reliance and having each other’s back spirit with people I work with. To this day, those relationships have lasted and my very early career to my middle career to now are marked by The connection I was able to

garner with my colleagues by letting my family in and letting my daughter be a part of my schedule, it really changed my relationships at work. I know people feel like it’s very risky and everybody’s situation is different, but it really is true. People want to know people. Again, people work with people, people quit their jobs not because of the company, it’s because of the people.

It is so true and I think we continually forget that, that being a real person and a rich person and an open person builds that connection and helps build that culture of interdependency and reliance on one another.

Kevin Rice (20:08)
Yeah. Isn’t it wild because I, and I’m sure many others would be really afraid and be in fear to cut back on hours because I thought this is the only way that I have so much responsibility. There’s so much pressure to perform. This is the only way that I can get it done. And then by pulling back, you actually found that your team was able to rise. You had better relationships with them and you know, it’s, it’s amazing to see the

Deborah Palmer Keiser (20:23)
Mm-hmm.

Kevin Rice (20:35)
positive benefits that come out of something that you would logically think would be detrimental to your

I constantly finding

Deborah Palmer Keiser (21:00)
Mm-hmm.

Kevin Rice (21:01)
the parallels of what I’m learning in my parenting and what I’m learning in my career. I’m curious, do you find that you learn different, but the same amount from maybe the teams that you work with in your professional career?

Deborah Palmer Keiser (21:16)
I would say in my early career, I was a leader of, i will show you how to get something done because I will do it alongside you. But it was more in the spirit of kind of dragging people along. Like, we’re going to do this come hell or high water, and I’m going to show you how to do it the whole way.

I think having my daughter taught me leadership as a service model. I am in service to the teams who I lead. And part of being in service to them is asking genuinely, what can I do to help? What can I do to contribute? What do I need to hear from you and understand,

in order to grasp what the situation is rather than a tops down leadership model. It’s really the servant leader of being in service, similar to a child. I am continually amazed at the magic of children. Their insight, their ability to articulate what they see, again, not laden with emotion or context or history or, you know, it’s unburdened.

And I realized that as we grow up, there’s a level of conformity and expectation, and it kind of tamps down that honest observation, insight, articulation. And if we could keep that in our adult life, we could relate to one another differently. We could share insights without them being threatening or insulting or judging. There’s a lightness to what children do.

So I think after having my daughter and observing her and listening to her say the most remarkable things out loud, I was like, oh, do we say that? And then realizing that, yeah, it’s perfectly fine. And it’s the tone and intent and spirit in which things are said. It fundamentally changed who I was as a leader. And coming into my own emotion, having a kid in the background or having my husband

come and put his face in a Zoom call just to meet people, he always says to me, can I please see the org chart? Because every new organization I’m working with, I just start throwing names at them. And to invite my husband and my daughter into my work and have people know them, it gives them insight into me and makes me a deeper, richer person in service of them. And it really has made me much

more holistic leader in that respect.

Kevin Rice (23:39)
Yeah. It sounds like you have a really close relationship with your daughter, which is special. I know a number of business executives who their kids grew up and they just don’t have a really close relationship because they chose to prioritize their career and they weren’t able to really have that deep connection with their kids.

Deborah Palmer Keiser (23:57)
Yeah, one thing I like about supply chain and operations is that it has exposed me to the rest of the world throughout my career. There are some unique peculiarities of American professional culture that is go, go, go, do, do, do, get it done, get it done, exceed, exceed, exceed that many cultures around the world don’t share. It’s not that they don’t value.

accomplishment or professional respect. It’s that they allow their culture, they allow their family to be much more holistically a part of their life. I think spending time living overseas and then working with so many other cultures gave me a good lens back into America that sometimes I think Americans look ridiculous because we do act like

We have no family, we have no personal time, we take no vacations. And I, know, the people around the world are like, is that real? I mean, are you guys happy? A really simple example is, everywhere I travel in the world, wherever I’m going, the receiving party will make sure they know my flight information. They’ll make sure I have

a pickup at the airport, even if I arrive in India at two o’clock in the morning, they are making sure that either they are picking me up or an arrangement are made. They check in that I got into the hotel, they ask about the hotel, they will come and pick me up in the morning. When people visit America, like we have a meeting at 10 o’clock, I don’t know what time they got in, I have no idea what hotel they’re staying in, I didn’t check in with them. There’s a…

an interpersonal connection that many, many other cultures have that Americans just take for granted. You’re fine, you have a credit card, you’ll get there. And so to have lived outside of America and see America through a different lens really taught me a lot about the culture that we think is excellence and professionalism is actually just a stifling of a lot of things.

Kevin Rice (25:40)
Yeah.

Deborah Palmer Keiser (25:57)
And those lot of things are the things that my daughter brought to me, my husband also, but my daughter especially of why are you acting like I don’t exist? Why are you not letting me be a part of something? And humorously, I think COVID brought that to life where everybody had their kids climbing on their laps and behind them or animals or whatever. It just forced the issue for people to realize like, yes, life is all around you. It’s all around you and

Kevin Rice (26:01)
Mm-hmm.

Yeah.

Deborah Palmer Keiser (26:23)
you can’t isolate yourself in a closet from it. So maybe it’s eased up a little bit, but it is a very American thing that we got caught up in.

Kevin Rice (26:32)
Yeah. I just got back from a trip to Fiji and probably the biggest thing that surprised me that I was not expecting was just how family oriented the culture is and how much they love little kids. We brought our 19 month old and he would run around the restaurants. And if he walked within 10 feet of any of the staff at the resort, they would run to him and play with him for five to 10 minutes. He was like the highlight of the restaurant. he’s really cute, but

Deborah Palmer Keiser (26:45)
Yeah.

Kevin Rice (26:59)
this is part of their culture. This is how they live. And if an American tourist was there, he would stop and wave to them and they would just kind of walk by and he would look at them like, you guys are broken. There’s something wrong with you. our server would pick our son up and fly him around the restaurant, Like he’s an airplane.

Deborah Palmer Keiser (27:11)
Yeah. Yeah.

Mm-hmm.

Kevin Rice (27:19)
and my fiance and I were able to enjoy a conversation at dinner I was like this is wildly different than American culture you would never expect something like this and we really we loved it we fell in love with the culture and the people in Fiji

Deborah Palmer Keiser (27:30)
Yeah.

Yeah, and it really does connect you with people. We had a similar situation. I was in Europe for an extended period of time. I had to extend my trip one more week and I said to my husband, I bought you guys a ticket. You have to get on airplane tomorrow. I’m not going to be away from you one more day. And they arrived in Florence that afternoon. We went to dinner And my daughter was two,

sitting on her lap and we’re kind of eating around her shoulder. And the wife, the owner of the restaurant came out of the kitchen, picked up my daughter, put her on her lap and then walked back to the kitchen to give her her own little kitchen experience and came back. She had her own bowl of Parmesan and everything. And they just wanted us to enjoy the food.

Yeah, the thought of that happening in America, like, wait, what are you doing? Where are you taking my kid? ⁓ It’s very different. it really, those kind of experiences really stayed with me and really changed me. So it was a combination of my daughter and then what my daughter’s presence opened up during my professional experience that never left, really never left me.

Kevin Rice (28:24)
Yeah.

I know you’ve traveled a lot in your career. Did you travel a lot when you were growing up or I’m curious how your, kind of childhood influenced how you thought you should act as a mother in those kinds of early years.

Deborah Palmer Keiser (28:54)
We largely grew up with my father, my mother had some mental health issues and basically checked herself into a psychiatric hospital, way back in the day. Like this is, you know, early 60s. Women were given uppers to get skinny and downers to sleep.

my mother couldn’t have her own bank account at the time. I explained to my daughter the environment for women of my mother’s generation. And it’s pretty shocking to think just in two generations how different things are. But my mother had a hard time. We ended up moving with my father who was a serial marrier. So we moved quite a lot between the United States and England and from one coast

to, every two years we moved. My father was either an educator in or the headmaster of the schools that we went to. And so it’s kind of hard to be the, it’s kind of hard to be the new kids every two years and headmaster’s kids and whatnot. So we grew up with a lot of insecurity, a lot of financial insecurity, a lot of ⁓ home insecurity. And I think that that fed into my assumption, my belief that if I

created a home, especially with a parent there, if I just provided that, then that was good. That’s job done. I did a good job. Because I didn’t really grow up with a mother, I would say I have had a lifelong mother want to find female mentors, to find female friends. It has always really been challenging because I don’t know what it

feels like and strangely enough in this period of my life with my daughter, I get a sense of what that feels like. The feeling of being home with your parent, wherever you are, but being home, it is safe, it is accepting, it is loving. I have that feeling with my daughter in reciprocity or in reverse and reciprocity that I feel very much home

when I’m with my daughter and I realized how much I missed ⁓ from my mother. I’m the youngest of three. I think it kind of, it’s a bug that stayed in me. I have therefore moved my entire adult life. It’s just something in my bio rhythm that I don’t mind traveling. I don’t mind picking up and moving locations.

But I think it has affected my bio rhythms, how my brain works to the extent that now I realize that maybe my daughter wouldn’t have liked to have moved around so much in her youth.

She grew up on three continents, know, born in America, but largely brought up in France, had a stint in Singapore, moved back to France, then came back to America. And I think only now that she’s 24, is she’s starting to realize she’s a child of the world. The trade off of being a child of the world is you are a little bit homeless. Like you never really feel that you’re entirely at home in any culture, which makes it easy to be

Kevin Rice (31:47)
Hmm.

Deborah Palmer Keiser (31:58)
kind of at home in any culture, but there’s a trade-off there. that’s the way I raised her. She’s handling it now, but I realized I just perpetuated what I grew up with and ⁓ offered that to my daughter.

Kevin Rice (32:09)
Mm-hmm.

It sounds like you really focused on what you needed as a child and giving her that security or safety. but missed what she actually needs. And that’s the connection. Like, you know, more than just attention, but real presence, from you.

Deborah Palmer Keiser (32:14)
Yes.

Yeah.

Yeah.

think in early parenting, we spend a lot of time projecting. I think it takes a while for us to learn what parenting is. And sometimes, parenting is making up for the parenting we had before you can actually truly parent your own child. Yeah. Yeah.

Kevin Rice (32:33)
You’re fine.

you

It’s like reparenting yourself. Yeah. I think we’re kind of the first generation

like, or just this time of the world where we’re thinking about reparenting ourself while we’re parenting others.

Deborah Palmer Keiser (32:59)
yeah, yeah.

Kevin Rice (33:01)
you moved around a lot as a young kid. How did that influence who you became in your career?

Deborah Palmer Keiser (33:07)
I’m ready to pick up and go anywhere for something that’s interesting. My career is built from curiosity and more often diving into that which I don’t know or do not necessarily have the skills yet. I have taken on challenges that either nobody else would or that’s

I wasn’t really equipped for. I think the way I was raised having to navigate around the world, oftentimes without parental oversight or support made me really

self-sufficient, willing, and unafraid. I don’t I learned long ago that our greatest, towering strengths are also our towering weakness. That it’s usually not a collection of strengths and a totally different collection of weaknesses. My towering strengths are fearlessness, willingness to jump into the unknown, and self-reliance.

And I can go full tilt on that. And, you know, I used to describe myself as an isolationist introvert because I can spend an enormous amount of time alone. And I have great courage to believe that I can do anything that is set before me. And again, I think in my early career, I would just drag people along versus inviting them to be part of it. And when I learned to

paint a portrait to lure people into wanting to be a part of that portrait, that’s when I became a much deeper person and a much more effective leader, because then everybody rallied around that.

Kevin Rice (34:43)
Yeah. I know that you are a very confident and capable leader and you were mentioning earlier that your daughter is going into a very different career path and she’s going into the arts. She’s a vocalist, a budding singer. I don’t know that I’ve talked to a lot of parents who have kids that are going into like non-traditional careers. Almost everybody I know have kids that are being groomed for entrepreneurship or business or

Deborah Palmer Keiser (34:59)
Mm-hmm.

Kevin Rice (35:09)
tech. I love that your daughter is pursuing her passion of being a singer. How did you feel about or how did you support her dream of becoming a singer as she was, moving out of the house and saying this is what I want to do?

Deborah Palmer Keiser (35:11)
Hmm.

Well, she articulated it at a very young age. she was six and she started to tell us that she wanted to be a singer. you know, kid of six, you go, yeah, yeah, that’s cute. And, you put on your little sequin dress and dance, lip sync to Mary J. Blige or something. And it’s it’s darling. It’s cute. But she she did not relent. following music, taking up

piano and She had a jazz piano teacher at the time and her jazz piano teacher said, you’re gonna

perform with me in the restaurant. And Tilly, she was pretty shy. She would hide behind her father’s legs when she was introduced to people and whatnot. But When she breaks through, that kid comes alive.

we watched her kind of throwing a fit, not wanting to do it at the last minute. And then when Ramona gave her the mic and started to play the piano and then Tilly started to sing, and I thought, oh my God, maybe, maybe that dichotomy of she’s very reserved and shy, but there’s this person waiting to bust out of her. And that is the medium that enables it. And we just continued to see that.

we continue to see that when she was on stage in any capacity she would come to life and there was something calling her for that.

So I think she comes by it naturally. Her father is a creative. He’s a photographer and a videographer, all self-taught, crazy talented. And I guess that’s part of I’m not really afraid of that world, what it implies. I think everything is hard. I think every career is hard.

Every self-actualization is hard. But people get scared because their kids aren’t going to make any money. It’s like, I don’t know. You could be a consultant for 25 years and find yourself just gutted from your soul and actually not really have any money. Personal path is a personal path. I would rather see her follow that energy and follow that life that comes out of her.

Kevin Rice (37:13)
Yeah.

Deborah Palmer Keiser (37:24)
and see where it takes her. She’s a beautiful ceramist. She’s a beautiful graphic designer. So she’s got backup stuff if she needs to. But if music is really where she wants to go, my feeling is take it all the way so you don’t have any regrets. If you decide ultimately not to do it or it didn’t work out, you took it all the way. Because I see too many people not take things all the way. And I don’t know.

I think it’s only when we get to about 50 years old that we say life is short, but it really is short. Yeah.

Kevin Rice (37:54)
Yeah, follow your passions. Not to mention,

arts could be the safest career path moving forward with so many business professional, like, you know, knowledge working jobs being replaced by AI. The arts might be the safest place for her to go, but it’s beautiful to hear you talk about her pursuing her passion. And you almost have a sense of awe when you speak about her singing and performing.

Deborah Palmer Keiser (38:04)
Mm-hmm.

Yeah.

Kevin Rice (38:19)
Did she ever want to throw in the towel and quit singing or was she always moving forward in that direction?

Deborah Palmer Keiser (38:25)
She wanted to quit playing piano a number of times. there was just a hard no. And we would say her piano teacher would come over, lovely woman. And if Tilly was having a day of it, they would just sit at the piano bench and talk. I was like, that’s fine. I don’t care. It can be going through the motions. But no, you can’t quit piano. So didn’t do your homework? You got to tell Ramona that.

Kevin Rice (38:28)
Mm.

Deborah Palmer Keiser (38:52)
But if you just want to sit at the piano and talk, then that’s fine. But Ramona will talk music theory, or she’ll talk, you know, is always music related. But she wasn’t allowed to quit that. And that’s, I mean, it’s kind of how I roll anyway. I think people quit because they get afraid. They quit because they’re scared. They quit because they’re not perfect. And to break through that perfection, oftentimes people can be great at something just because they’re having fun.

It doesn’t, they don’t have to be the best at it, but they’re great at it just because they’re having fun. And that fear, the kind of perfectionist spirit, when it starts to hold people back, I think it starts very young and that’s really difficult to break through as people grow older. So we did our best to push her through stuff. You my husband, he’s done all the cooking in our family and really enjoys food, really enjoys food. And they would travel together and he would say, whatever the food is.

You have to try it at least twice because the first time may not be the best one. If you try it a second time, then you can opt out of it. And she is very much in that spirit. Like, I don’t know what that is, but I’ll try it. And if we could capture the spirit of children

in adventurousness and support them through the fear of something. They come out the other side and they own that spirit. But if we give in to them saying, I don’t want to do it, I’m scared, that kind of gets frozen in our adult heads.

Kevin Rice (40:18)
Yeah. And I imagine that those values that you were helping instill in her like resilience and grit and not quitting are probably values that you carried into your professional career and probably helped

instill in your teams as well.

Deborah Palmer Keiser (40:34)
Yeah. Yeah, I tend to overuse the expression, the Socratic model of we don’t have to agree on anything, but I want you to walk me down your path of reasoning and process, because we’re going to get there. And when in doubt, I will always have a way, but it doesn’t have to be my way.

take me down your path of how you think we can get there. But we’re gonna get there. There’s no like, you know, it’s too hard. There’s none of that. I think that’s where my self-reliance comes in that I don’t give up. And when in doubt, I will follow my own path. But I really enjoy bringing people along and asking them, you show me, you tell me. I am happy to change my mind.

And it’s, yeah, think it’s, that’s probably the only little childhood spirit I hold on to.

Kevin Rice (41:30)
I recently had somebody ask me, he was a, entrepreneur. He’s kind of scaling his company. He knew my story of growing a business and selling it. he’d asked me. Cause we had kind of a personal conversation about, some similar topics about some of the milestones that I had missed and sacrifices I had made. And he asked me would you have done anything differently knowing what you know now? And I’m curious as you look back on your career and your personal life.

What have you learned or what maybe would you have done differently or what advice would you share with the audience?

Deborah Palmer Keiser (42:02)
My advice to people would be if there’s something you want to do, take it all the way. Take it all the way and develop an openness of expressing fear or trepidation to allow people to help you.

I was a little bit of a black sheep in my family because

I was a self-taught seamstress. I went to FIT after I went to college.

I learned the trade

by doing, just by taking jobs and doing.

But I started my career in this industry wanting to be a designer. And I had a custom clothing business when I was young. I did not have the resources and support system around me.

And I lost confidence and I switched tracks.

I just was not in that place as a young professional. I started a men’s luxury tailor clothing business And I had been making custom clothing for men in New York City. And one of them said, your product is so beautiful. If you give me a business plan, I can see how I can help you. I didn’t know what a business plan was

I didn’t go to business school. I went to liberal arts and studied linguistics And then I went to FIT. I didn’t know what a business plan was. And I was so fearful of the fact that I didn’t know what it was. I didn’t ask anybody. And I just kind of froze. And I never got back to that person. there were repeated things like that, like little signals of you might want to open yourself up. If you want to realize this dream, this is what you want to do.

Kevin Rice (43:35)
you

Deborah Palmer Keiser (43:45)
I just think a lot of people get too fearful of what they don’t know or lacking perfection or the stories of entrepreneurs starting companies at scales and that, that, that it’s a story that almost inhibits people rather than propels people because if it’s not done a certain way in a certain amount of time and a certain X factor, it’s not done well.

Kevin Rice (44:02)
Hmm.

Deborah Palmer Keiser (44:12)
So my advice would be stay the course. Stay the course of what you are wanting to be and do. Stay the course. And figure out ways to build a network, or find those mentors, or find those people who are willing and able to support you to realize what you want to do. When you decide it’s not what you want to do, change course. Because one will have acquired skills and learned a bunch of stuff on the way.

Kevin Rice (44:15)
Mm.

Deborah Palmer Keiser (44:39)
That’s what made me a great person in supply chain because I knew to the textile, to the needle, how product is made. So I don’t have to be in a foreign country in a factory to understand. I know how product is made. I can interpret it. It’s a very visceral understanding. So it made me really good at what I ended up doing, but I didn’t do the thing I wanted to do. And that’s why I am so pursuant for my daughter.

Kevin Rice (45:03)
Yeah.

Deborah Palmer Keiser (45:07)
run the course, do it, take it all the way. Because there’s going to be plenty of stuff that is going to knock you down. You’re not going to know. You’re going to feel scared of no matter what you do. So you might as well be doing the thing that you really set out to do and that you really want.

Kevin Rice (45:20)
Yeah. Especially when you’re getting those kinds of cues from the universe, like you mentioned somebody coming and asking you for a business plan. And I, I think the universe leaves breadcrumbs. If you’re willing to look for those breadcrumbs. I had a number of those when it came to just starting this podcast. And so I felt called to do it because so many little things kept adding up and it was, something that I’ve been very passionate about.

Deborah Palmer Keiser (45:26)
Mm-hmm.

yeah. And I’ve had a great life partner. I have to say, I’ve been with my husband, not married the whole time, but for 33 years. And finding a person who is your partner in life, who not only helps you grow, but forces you to grow out of love is very meaningful. And so it could be a friend, it could be a life partner, but it’s, I don’t know that I would be half the person I am.

Kevin Rice (45:58)
You

Deborah Palmer Keiser (46:07)
also without him.

Kevin Rice (46:09)
Deborah, thank you so much for being with me today. I really appreciate the candor and the vulnerability and some of the deeply personal stories that you shared with us. I think what really will stick with me is kind of that story of your daughter asking to see your bank balance, not because she was really worried about the money, but because it was proof of your priorities, but mainly how you responded.

Not with just a perfectly timed career move, but by slowing down and spending days painting nails with your daughter. And then I loved how that actually turned into a advantage for your career. Your team could see you as a more humanized leader. and it gave them an opportunity to really elevate and take that opportunity to step up in their own roles. So.

I’m deeply grateful for your honesty, your vulnerability, and your wisdom, and just sharing the stories behind your personal journey as you’ve grown as both a leader and a mother.

Kevin Rice (47:12)
in to

Deborah Palmer Keiser (47:11)
Thank you.

I really appreciate

Learn About the Guest

Deborah Palmer Keiser, COO Pair of Thieves

Deborah is a globally experienced operator and supply-chain leader who has scaled, stabilized, and transformed some of the world’s most iconic retail brands. Across 30+ years, she has held leadership roles at Gap, Williams-Sonoma, Victoria’s Secret, Boardriders, AllSaints, and Yeezy. Today, she serves as COO of Pair of Thieves, guiding mid-size brands through operational maturity and sustainable growth. A devoted mother and champion of young creatives, Deborah blends operational rigor with profound emotional wisdom, leading with transparency, service, and heart.