Lessons from the Top: Navigating Career, Tech, and Life’s Curveballs

Welcome to Retailistic, the official podcast of CoreSite Research for July 21st, 2025. This week, our CEO, Deborah Wineswig, welcomes Lori Shaper, CEO of Digital Wave Technology. for a far-reaching discussion of professional development management styles applying ai tools and much more

But first, let's check in with Isla Meldon from the London office to discover what you can expect from Coresight Research this week. Retail is evolving faster than ever, and your decisions need to stay one step ahead. At Corsight Research, we deliver the insights that help retail leaders, like you, make smarter moves in an unpredictable market. Here's what we're covering this week, and why you can't afford to miss it. Consumers are heading into the new school year.

and what they're planning to wear matters for your bottom line. In our latest report, we wrap up our Back to School 2025 series by diving deep into the apparel purchases shoppers plan to make this season. Find out which categories are seeing the most interest, what trends are shaping the back to school apparel mix, and how you can position your brand to capture share.

At the start of 2025, we forecasted the key trends shaping retail in the US, China and India, as well as major shifts in the US retail real estate landscape. How are those predictions holding up? Our mid-year reviews will help you recalibrate strategies by assessing where we got it right, where surprises emerged, and where the next six months may take us.

With the latest US Census Bureau retail sales data now in, our team analyses the trends and reveals our predictions for July 2025 retail sales growth. Whether you're looking to benchmark your performance or set realistic expectations for the month ahead, our outlook gives you the data-driven clarity you need. By subscribing to CoreSite Research, you'll get these reports and more delivered directly to your inbox every week.

Join thousands of retail executives who rely on our actionable, forward-looking analysis to stay competitive. Thanks, Isla. Now let's welcome Deborah and Laurie.

Lori, thanks so much for joining us today. Deb, always a pleasure. Hope you're doing well. Thank you. You too. So I still remember, oh my gosh, it was at least a decade and a half ago, being on stage with you at NRF and just... being so in awe at the way you thought about the industry, the way you were able to communicate what was happening and really resonate with the audience. If you go back...

in your career, what was it that got you to that moment? And how did you know kind of your calling was to not only work in tech, but also, I think you've always led with education. And that's what's really unique about you. Well, thank you. So when you say what led me to it, I think obviously everybody's a product of the way they're brought up, the way they're raised, the education they have, all those things come together. And I was raised in a...

Midwest, very traditional family, great values. I very much love my parents to this day for everything they've taught me. And then I went away to school and I was very good at math. and analytics, that kind of a thing. And so somehow I ended up in the computer science field quite a while back. And from that perspective, I also ended up at Procter & Gamble as my first job and then in retail. So that combination.

of AI type of analytics, data science, computer science, and business, especially in the retail and consumer goods field is really where I've left my mark. And I love to teach people. I love to help people. That's just part of, I guess, my nature. That's great. And how did you figure out in high school? what you wanted to do. How did you then like figure out what college, because there's a lot that had to line up for you to get to where you are today. I'm going to say a lot of luck, candidly.

I wanted to be either a doctor or a photographer. I had a creative side that wanted to be a photographer, and I wanted to go to New York fashion and major in photography, and the other side of me wanted to go to MIT, and my father said, no, no. Your older brother's in medical school, and this is back in the 1980s in the Midwest. And heck, you know, other than I had very good grades in high school, I really didn't have much ambition. And honestly.

I pretty much got told, you need to major in this because it's going to go places, which is a combination of computer science and mathematics and business. And that was it. And what was it, you've mentioned a few times, you really loved math. What was it about math that drew you to it? You know, it's problem solving in general.

I've always enjoyed solving complex problems, and mathematics is nothing more than solving numerical problems. And I just happened to be gifted at it. You know, I just fell into it. I was very good at math. I was one of these people that did well on everything, but when it came to things like grammar and English, let's just put it this way, I had to struggle to be good at those sorts of skills, whereas the math just automatically came to me. Did you...

I don't know if it was in high school or college, were there things that you participated in to kind of like test your math prowess? Or how did you kind of outside of the classroom continue to level up or really kind of test the mettle? I was very active in high school and college in a number of things. I can't say that I really tested my prowess for math outside of school. Honestly, like I said, there was probably a lot of luck.

And upbringing, my father is an extremely brilliant engineer. And so he would, at the dining room table, he would make me derive integrals and derivatives and actually walk through the way that... done at the dining room table so that when I was in calculus, advanced calculus in high school, he was my mentor.

It's such a great story. So my dad, I wanted to be a doctor as well. And I was getting there through chemistry. And so my father would do my chemistry homework before me. And then I would do my chemistry homework. And then we would sit down and we would compare.

Right. How we and it was such a I think having kind of that strong parental foundation and someone who I mean, literally like he got an additional textbook. Right. And and the idea that you could talk about something that you love so much. It's academic. cool, which is not supposed to be fun. Yeah, no, I, I totally, he, he really kind of also like, I don't know about how you felt. It brought it to life.

Absolutely. Yeah. Yeah. I mean, he brought it to life. And candidly, I got my mom's natural personality in a lot of ways, but I got my dad's drive and my dad's, I'll say, love of math. Honestly, today, I couldn't do it if my life depended. on it. I am 100% business, but I know who to hire. And back in the early days, I did all the fancy algorithms and now I couldn't do it if my life depended on it.

But I think that actually having that background, I mean, it goes back to, I can see things, especially in this day and age of Gen AI, Gentic and beyond, right? I can see things. Like if someone was like, can you help me fix my code or whatever? Right, it goes back to. it's all like pattern recognition, right? So I feel like you're, so even though you're not necessarily doing it day to day, I bet your ability to see something that others can is still second to none.

I think it's because, again, yes, absolutely. And it's really that training early on in life. And, you know, I think about in college, my job was I was an assembly language program debugger because it paid well and I needed to pay my way through. school and that was a great way to do it. And that is about as granular and basic as you can get in terms of computer science and also the math that...

went behind solving some of those problems. And so nowadays I'm dangerous, no question. I'm not the right person to go too deep on anything, but I know the questions to ask. I know the traits of, you know, the human character that we want to... hire wherever I am in my role today at Digital Wave. Goes back to those jobs, I think in high school or college. They define you. Yeah, I mean, it was, I mean, when I was younger, I had like a paper route.

I had to get up every morning at 5 a.m. right by like 630 or covered like head to toe and newsprint. Right. I mean, it was. But going back to my dad, because they were my parents were afraid, like pitch blackout. So my dad would like drive along near me.

I'm delivering papers, right? Good for him. And so it is interesting when you think about some of those earlier and going back to whether it's, you want to look at being scrappy or kind of being able to figure things out, there is something to be said.

about being able, almost like pushed out of the nest early on to figure some of that stuff out. I agree with you. I agree with you. Yeah, I was pushed out of the nest at college and never looked back. But I am grateful to my parents for doing that. With your first job after college, how did you decide where to work? What did you hope to get out of it? And how did that set you up for what was next in your career?

Great question. So I have to admit, as a 21-year-old graduating from college and needing to make my way, I admittedly looked for, gee, who's going to pay me the most? You know, that's one of the factors I have to say I took into account. I happened to be interviewed by a number of companies one of them Procter & Gamble who I had also interned with and that I was you know honestly kind of flying blind in my

Once again, my family said, oh, that's a great company. You know, you can almost get an MBA by going to Procter & Gamble. Okay, I'll do that. And they needed data scientists way back then. And that's how I got my start. And obviously, at that point in time, dating myself, personal computers were just coming out, you know, the double, dual floppy disks, that sort of thing. The CEO of P&G picked me amongst four people to say, hey, these young kids are going to...

teach us how we need to work with retailers so that we can get more shelf space and more control of the categories. And that, long story short, that got me into retail, that got me into AI early on, and then I jumped into retail. technology and the rest is history. But that's so interesting when you think about it, that they were thinking about it back then, right? I mean, what a fascinating approach. And I think the great thing about it, I also had an internship at PwC.

And the funniest story is on the last day, they make me an offer. I'm only a junior, right? It's like my second semester of my junior year. And so I'm like, yes, I want the job. And I think they, the HR person was like, We've never had anyone accept the job. But I was like, they went to...

There were only like six public accounting firms. I'd had a phenomenal experience. And so, you know, I was like, yes. And so it was amazing because it allowed me my whole senior year to either focus on studies. I took a big exam as well, but it was amazing how kind of how.

Having the internship set you up well for post-college. That's right. One less thing. And you already knew the culture then a little bit as well. That's right. And so, you know, I hadn't expected them to ask me to start. I had like a whole summer plan in Europe and like I got a call and like mayo. Can you start June 1st? Of course I can. So, no, it was interesting. And so if you think back on it, how did you learn to work with others? And because I think, right, that's a skill set that.

You know, you know your craft, but oftentimes kind of interpersonal, a lot of those things that come up at work. How did P&G help teach you that? And how did that stay with you the rest of your career?

I think that first role out of college, large company, well-known company. Good ethics at the time, very strong HR policies. Even back in the 80s, they were already focusing on everybody's equal, that sort of thing. And back then, you had to wear either a blue suit or a gray suit or a black suit.

But those rules taught me a lot about interacting because I was interacting with people, obviously, from 20s to 70s, perhaps, or even 80s in age. And I think that early discipline, you're not allowed to... drink on the job. You're not allowed to do anything that would misrepresent the company's brand. That's ingrained at an early age. You start at 21 years old, it sticks with you. So I think pretty much that, and then just tons and tons of experiences as I continue.

on. And did you end up doing any kind of post-college, post-graduate work? Because I feel like you're a lifelong learner. What are more of the details around that? I'm intellectually curious.

That was from the time I think I was old enough to remember, and I can remember at a very young age, but I just want to learn everything. There is to know. And there's never time in a day, and I've had to give up a lot of the perfectionism that I had. when I was in grade school and high school and college. And gosh, you know, it's okay if, you know, I'm not perfect in business. You learn to go 80-20 and not 99.999. But it's just intellectual curiosity.

When Generative AI first came out, I was the first one to say, okay, I'm going to put my entire company through the MIT course on Generative AI because that was a few years back because we are going to have to know this. So it's more that type of thinking. It really wasn't about getting the perfect education. It's just more, I just always want to learn everything I can about what I'm doing or what affects my life.

I tend to read an enormous amount. It's just part of my makeup. So leaning into that... There's so many distractions today between social media, all kinds of video, TV, etc. How do you limit the distractions? How do you think about managing your time? Because to me right now, it gets increasingly difficult by the day.

It does. It does. It's incredible the amount of distractions in a business day or in anybody's day. The phone's constantly ringing. You're expected. I think about in our company, there's Slack, there's Teams, there's text, there's email, there's WhatsApp.

You can't possibly keep up with everything. I set ground rules. I tell people this is where I'm going to be. These are the priorities that I use for communication. You have to set up communication boundaries. Otherwise, it will take over you instead of you. you being able to direct what you need to in business.

So I'm very clear about that with my team, you know, i.e. I only check WhatsApp twice a day. I can't keep up with it. Great example or Instagram, that sort of thing. LinkedIn, it's once a day in the morning. I do block a couple hours. every day for my own personal time of learning in business. and doing that sort of thing. But beyond that, it's really about you setting the priorities for yourself and your business, not the other way around, because it will take over if you're not careful.

Yeah, I think there was some research done by a large tech company and they were saying that if there isn't some kind of movement or whatever on screen, like every eight seconds, because we're so now hardwired for constant engagement.

So I think about that now, like even when I'm presenting, right? Like I'll have like a video behind me or something because like I get it. I mean, I'll tell you one of the things that I had done and I was in China in 2019 and then coming back to the U.S. was spending so much time at home.

I literally wiped out all notifications and I moved all news into like a Gmail account because I was like, if it's all coming into my inbox, in many cases, you're like, oh, right, like it's all like clickbait. And so what I found was if I didn't do that,

If I didn't separate, then some of the work emails I would either not get to or you'd forget about because you were like all on this 12 levels down on some clickbait. Absolutely. I'm laughing because as you're explaining the story, Deb, of what you did, I didn't do that.

In the amount of time you've just talked, I've had seven messages fly by on my screen. A personal message from my brother about my parents, a bunch of business messages, none of them, by the way, that couldn't wait. But it's those constant distractions that you have to be... able to just say okay tune it out till later wait wait okay that's important to reprioritize but you have to be very quick

Yeah. I think the greatest challenge, and I think you nailed it, was, right, you get messages in text. You actually get messages in LinkedIn. WhatsApp is increasingly used for business around the world, right? Like, I'm on WeChat. Then there's email. And then...

if I get going back to, I moved all, all news to a Gmail, but then if I see something interesting, I'll forward to the team. Now, now they're like responding to my Gmail and I'm like, Oh no, no, no, no, no. We've got it. We got to like going back to, I like the rules of the road. Like maybe I'm saying.

you're from Gmail, but let's kind of include like the work email on the other side. But I think some of those things are challenging. So let's talk about the learning piece. And if you think about over the years, because there's so many different avenues and so much of it is free now, right? I mean, a lot of the universities have great. And once again, all free.

How do you decide what to look at, when to look at it? Because to me, you can also set aside that time for learning, but if you're doing it in maybe an inefficient way or maybe looking at things that aren't really relevant. you're not going to kind of achieve the success you have. No, that's right. I wish I had the perfect recipe. I don't. I learn every day as I go. And the number of channels of communication just keep growing literally every week, I think.

One of the things, I mean, and even business email now has gotten to be where there's so much spam that you can't keep up anymore. I have to live by priorities. Everything I do. And I have to be able to just go into my day first thing in the morning and say, okay, this, this, this, and this. And you know what? If nothing else gets accomplished, that's okay.

And in terms of, you know, at nighttime, sometimes late at night when I want to unwind, I unwind by getting on generative AI and asking questions that I don't understand about life or about health problems or what have you. you know, during the day, I've got to just stay very focused on what are the most critical priorities that I need to do for our business today. And do you have like a morning routine or do you try and get up at the same time?

What do you do when you wake up? Like, can you just walk us through like what? Because I've always thought that the more that we can call it wash, rinse, repeat, the less decision fatigue. How do you start your day and how do you think about that?

Well, I try to start my day. And as an entrepreneur in technology, it never quite comes out the way I wanted it to. But, you know, I try to start my day with about 30 minutes at the beginning of just thinking through the day. I'll be on the computer. I'll be saying, okay, how many thousands of emails did I get over the course of the last 24 hours that some I've read, some I haven't gotten to? And then I look at my calendar.

And I just think it's private time. I think through, okay, this is what I need to accomplish. No interruptions. And I'd usually get up early enough that I can do that. And then I just go. I know, I mean, we've been friends for a long time. I know that physical fitness has always been really important to you. How do you make time for that? And whether it's physical health or mental health, how do you find time to balance that?

It gets, you know, it's hard. I'm not perfect. I'm far from perfect. I love physical fitness. You know, for a long time, I ran marathons. I was a runner and a swimmer and, you know, all that sort of thing. And then your career takes different paths. Life takes different paths. My parents became ill a few years back. I started a new company. And all of a sudden, there wasn't enough time for that. And, you know, honestly, fitness took a little bit of a backseat. It had to.

But I've pulled it back again where it's pretty balanced. But, you know, you go through phases where you're on and sometimes you're not as on as you should be. But life is a learning journey all the way to the end, I believe. And I'm at a place now where I've realized...

you know what, physical fitness is really important. I may not be great at it, but I took a walk this morning, five mile walk and did three calls on the walk, you know, so because there's no time otherwise to get the physical fitness in. So, you know, you just have to adapt. your own lifestyle and make sure that you could fit everything in.

It's funny because I love to be outside. I love to walk and run. Going back to setting your priorities, you know the stuff that keeps on getting pushed to the next day to the next day. And so what I've started to do is I'll walk and do it. And I try to do it when it's not super dark out so I can make sure.

I'll be on my phone. But I find that if I'm doing something that's hard or really don't like or don't want to do, that I can do it better if I'm outside walking or, well, my gym won't allow you to do phone calls, or at least I've gotten yelled at a few times.

Because you get excited, right? And you're loud. And I get shushed. So I don't do that anymore. Actually, I probably don't go to the gym anymore as much as I... As much, yeah. At a certain point, I'm not used to being shushed. So it... No, but Deb, you're an amazing individual. I'll tell you what, if I can have the focus and the pace that you keep, boy, I'd be more of a person than I am today. I have to give you credit for all that. You're amazing.

It's just why we're having this conversation because I've always thought that you've done such a great job. I've never had you say something and not eventually do it. there's very few people and you know and sometimes we get there faster we get there a different way it's it's shorter sometimes it's longer but i do think going back to like as a friend right like you're someone like i know if you say something i don't have to worry right

It's going to happen. And that really, I think, from a work perspective as well, right, that that says a lot. Absolutely. As we start to wind down, if you were to go back and change any of the major decisions that you had made.

what would that be? Good question. Well, I'd change a lot of decisions, but my life's been pretty good, I have to admit. I would just say I was too serious. In my upbringing, sometimes I wish I would have enjoyed things a little bit more. In high school and college, I was involved with everything, but... Deep down, I was always trying to make sure, as I said, I have a streak of perfectionism. It's long gone now, but it took a long time to get to that point.

And I guess that's the one thing I would change. I wouldn't change my upbringing. I wouldn't change my values. I wouldn't change the bad things in life that happened to me because they all taught me a lot.

I remember my father loved his job. And even when he wasn't working, he was working. And sometimes he'd be sitting right across the table from you. I'm like, Dad, he's like, oh, I'm just figuring out this problem at work like I need to solve. Right. And I met somebody and I was very, very fortunate to meet her. Actually, I met her at a Fortune Brainstorm.

event and i remember her telling me i don't work to live i live to work she's like because i love i love what i do and i and like not apologetic but there's right it goes back to like oh i you know you learn this little thing and it ends up having a huge impact on your Or you spent all this time and went down this rabbit hole and you probably learned something from that. But I think that this kind of constant excitement about the retail landscape.

about where your company sits in that, about where your team sits, to me, that's so much of who and what you are. Thank you. I have, yeah, I definitely have two sides. I have the personal side and I have the business side. And sometimes they intersect. Most of the time, I'm pretty good at keeping them separate. But there's no question that the personal side is who makes you as an individual. The values make you as an individual.

I love people. I love teaching. I love caring for people. At the same time, as I said, I can't help, but in my genes from the other side is a very, very driven person. So it's a combination of both. Last question. If you were to provide a few critical pieces of advice to kids graduating now, right, and it's a challenging landscape.

The amount of kids I know who graduated in May who are still looking for roles. Of course, many, many have amazing jobs. But what what advice would you give them in terms of how to think about the environment, how to think about their career? And, you know, if they're still looking for something, what would you suggest that they do? A couple things. I think things are a lot different now than certainly they were when I was in college, but a lot of things are still similar.

First of all, definitely do what you love. I think that's important. That's probably, I probably didn't get enough of that kind of thinking growing up, but it ended up fine. The other thing is I do think that kids nowadays also need to find their way and they need to make their way. That's a personal opinion that I really believe that young people coming out of school.

their parents do need to kind of push them off and let them swim without a life preserver. You know, I know that might be controversial, but I really believe that that's what builds character. That's what builds strength. And the earlier that that can happen, I think the better off in the long run of life. And I could say that because I'm over that, quote, magical hump and coming back down the other side of it. What was that, 35? And now it's, what, probably 50.

The point of it is that I really do believe when I look at the types of people we hire in our company, you want people that are self-driven. You want self-motivation. You want all those characteristics. an individual. And whether or not you make the most money at first doesn't matter. That doesn't matter at all. But what really does matter is your values, the way you come across to other people, the way you treat people, and also your own motivation and drive.

to learn that as a young individual by, I hate to say it, school of hard knocks, I think. No, I think those are some very wise words. And one of my very good friends said to me, he's like, whatever you do, don't let them come home.

And he was thinking from personal experience. And I was like, because he's like talking about like, he was talking about a bunch of goblet group. I'm like, what's going on? He's like, he's like, you have no idea. Just don't let them come home. He's like, they try to tell you what to do. And I was like, that's so, so funny. But it's fair. funny actually kind of listening to you because i remember my my parents when i decided to go into equity research and they're like

what on earth are you going to do when you decide to like do something else? They're like, that's just to them. That didn't seem like a very, like banking. Yes, that seemed practical or sales and trading, but like research, they're like, what do you, what do you do with that? And so it was like, I remember like, I think that that's.

those things they're like here i am right many many moons later for making that decision and and still some days i'll be like okay like what am i gonna do like after the research but you know what you stand you know and i my peers did the same thing with me it's like You left Procter & Gamble? How could you leave Procter & Gamble and you went to some startup company? Are you crazy? But, you know, you learn to stand on your own two feet.

And as long as you're true to yourself and from that standpoint, you're going to be just fine. And again, also, thankfully, I had great parents who taught me to stand on my own two feet. And life is going to throw curveballs at you constantly. I am living in right now the most curveballs I've ever had dealt to me as an individual. But you know what? It just strengthened you.

And I think one thing, Lori, we didn't talk about is how important it is to have friends like each other. Because I will say one of my very good friends said, right, you can probably count your good friends on one hand. Like people who you call in the middle of the night, stuff is not going.

going well or, you know, who are always going to be there no matter what. And I mean, just to give some context, Lori and I have known each other for well over two decades and here we are. And during some of the challenges, I'm like, Lori, I will get on a plane and I will be there. And and she knew I meant it. And so I think those are the things. And don't ever hesitate. And you can you can actually intertwine like friends in business. But you can. I do think I've always said like health first.

then family, then friends, and then work is like at the bottom. That's right. Because I think all of those need to align in order for you to have a great life. They do. And, you know, Deb, I went through a, both my parents are in hospice now. It's a tough, tough, tough. from that perspective. I woke up one morning in January of this year, ready to go to NRF.

National Retail Federation show. Sunday morning, walked into my bedroom to try to get some clothes out of the dryer. And no warning whatsoever. And pow, I had the worst headache of my life. I passed out. I started vomiting on the floor. I figured I had the flu. I ignored it. Thankfully, somebody else that I live with didn't ignore it, and he called for help. And it turned out to be a ruptured brain aneurysm. And if you know the stats of it, they're not good.

I was put on a helicopter and airlifted to a hospital and had the best neurosurgery team around. And, you know, here I am. Six months later, it's completely recovered. But it does put things in perspective when you have a, you know, you have that type of experience. And you were one of the few people while I was in the hospital in ICU for weeks that was saying, I'll come down, I'll do whatever you need. just meant a lot. So I'm grateful for that.

I just had to share at FMI Midwinter two years ago. I was like, and for those of you who know me, I booked travel at the last minute because I'm going back to decision fatigue. I'm like, well, I could take this flight or I could take this flight. I could save up $50 here or 25 here. So now I just book everything really last. minute because it takes a lot of the decisions out like i'm like it makes total sense except

You can't always do that. And I had nowhere to stay. And Lori's like, you can stay with me. And she's like, I'm like across the street in an Airbnb. And so I stayed on like, you know, sleeper sofa. I mean, I can sleep pretty much anywhere. And it goes back to, right? Like when you're.

And there will be challenges. They can be personal. They can be professional. They can be both. But, you know, having, it goes back to like having those friends. And then I just also have to share, I'm very much kind of a night walker. Lori is very early morning. So I will say we stayed with each other for three days and never stopped. We never saw each other.

So I was making room in my suitcases for the candy bars I prioritized. And so I left all this stuff. And Lori's like, did you mean to leave? She's calling me, right? She's like, did you mean to leave this stuff? I'm like, yeah, I thought you'd love it. It was your size. So Lori, thank you for joining us. It's always a pleasure. Thank you, Deb.

The best success at Digital Wave. And for those who don't know, Lori has really been a pioneer in Gen AI and Argentic. And we wish her all the success at Digital Wave. Thanks so much for coming on today. Thanks, Deb. You take care. Good talking to you again. All right. Take care. Bye-bye. Bye. Thanks, Debra. And thank you for joining us this week.

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