#301: Julie Bornstein – Founder & CEO, Daydream – People skills matter most

23 Jul 2026 · 1 h 14 min · 34 chapters

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In short

Julie Bornstein, founder/CEO of Daydream (AI-powered fashion search), discusses how “people skills matter most” in the age of AI, plus her retail-to-tech journey and what she learned building consumer shopping experiences.

Guest background

Julie is a long-time retail and digital leader. She led e-commerce transformations at Nordstrom and Sephora, later scaled Stitch Fix (board member then executive) from about $10M to $250M and then to ~$1B, and launched The Yes (women’s fashion entertainment shopping) before its acquisition by Pinterest.

Key claims

  1. People skills are the most durable leadership advantage, even when AI changes everything.
  2. Customer understanding is the edge: being the customer lets you translate needs into product, engineering, and creative decisions.
  3. Building on LLMs is hard because outputs are non-deterministic, making consumer UX difficult.
  4. Startups teach humility; success isn’t enough—you must keep building capabilities.

Notable examples

  • Nordstrom: grew e-commerce from $10M to $350M by creating product management and aligning brands/vendors to sell online.
  • Sephora: built Beauty Insider loyalty and multi-channel digital experience (YouTube video integration, mobile as bridge to stores), growing web to $1B and doubling store business.
  • The Yes: launched May 2020 after COVID forced a pivot to “entertainment and levity”; Pinterest later deprioritized shopping after a CEO change.
  • Daydream: natural-language fashion prompts (e.g., “Valentine’s Day party… lace… sleeves… sexy”) and “find this, but in orange” style refinement; monetizes via retailer sales.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Reflecting on Year One of Daydream

0:36 to 1:04

Julie discusses her feelings about the first year of her business.

“You know, I didn't realize this, but I guess it's been almost a year since you, almost to a day since you launched Daydream.”

Childhood Influences: The Jetsons

1:04 to 1:53

Julie shares how watching The Jetsons inspired her interest in technology.

“And I feel like we're still just at the beginning.”

Shaping Leadership Through Family Dynamics

1:53 to 2:46

Julie discusses her upbringing as a middle child and its impact on her leadership style.

“And here you are, you spent your career helping millions of people shop better.”

Early Fashion Interests and Entrepreneurship

2:46 to 4:30

Julie talks about her early passion for fashion and starting a barrette business.

“I had an older sister and a younger sister.”

The Courage to Connect with Howard Schultz

4:30 to 7:26

Julie recounts her bold approach to meet Starbucks' CEO Howard Schultz.

“But I was definitely someone who was always aware of what was out there, really interested in it, really interested in the new things.”

Creating Your Own Opportunities

7:26 to 9:27

Julie shares her philosophy on crafting career paths and taking initiative.

“So I called his office and his assistant said to me, oh, he's actually interested in meeting with you.”

Transitioning to Nordstrom and E-commerce

9:27 to 11:52

Julie describes her path to Nordstrom and her role in launching e-commerce.

“And you mentioned Nordstrom's was another company you really admired that was in Seattle.”

Understanding the Customer's Needs

11:52 to 13:18

Julie explains how knowing the customer drives successful business strategies.

“And, you know, when you see that kind of growth, what belief did it reinforce that you've carried with you as you moved along in your career?”

Leadership Lessons from Sephora

13:18 to 15:55

Julie recounts impactful leadership experiences during her time at Sephora.

“And I would say, you know, both of those experiences really underscored for me the ability to really understand your customer and be able to express that in a way that's compelling to others.”

Building E-Commerce at Sephora

15:55 to 19:18

Discover the challenges and successes in establishing a modern e-commerce strategy at Sephora.

“So what did you do at Sephora that is statue worthy?”
Show all 34 chapters

The Decision to Leave Sephora

19:18 to 24:14

Understand the factors that influenced Julie's decision to leave Sephora and pursue new opportunities.

“And it was a lot of me and my team, who was amazing, nothing is done alone, as we all know, you know, really sort of trying to express before, ahead of the time, why this was going to be so important.”

Experience at Stitch Fix and Growth

24:14 to 25:46

Explore Julie's role at Stitch Fix and how it contributed to her growth as a leader and entrepreneur.

“But when you were at Stitch Fix, you really helped scale the business.”

Choosing Entrepreneurship Over Corporate Roles

25:46 to 28:01

Learn about the internal struggle and motivations behind choosing to start her own company rather than taking a corporate CEO role.

“You know, you once said that the job wouldn't be about creating something new.”

Transitioning from Corporate to Startup

28:01 to 29:34

Julie Bornstein shares her shift from corporate life to entrepreneurship and the motivations behind starting her company.

“It was very helpful to have Stitch Fix as a transition because I really got to sort of live the startup experience, which is very different from corporate life.”

Navigating the COVID Launch Challenge

29:35 to 31:28

Julie discusses the effects of COVID-19 on her company's launch and the pivot required to adapt.

“I mean, what was going on in your mind when that happened?”

Acquisition by Pinterest and Its Lessons

31:29 to 35:26

Julie reflects on the unexpected acquisition by Pinterest and the lessons learned during the process.

“And, you know, Pinterest ends up acquiring the yes.”

Introducing Daydream: A New Shopping Experience

35:27 to 37:12

Julie explains her new venture, Daydream, and its innovative approach to e-commerce search.

“So one of the things that I had always seen in e-commerce is that about quarter of the population uses search when they're on a site to find what they're looking for.”

Building Daydream and Learning Humility

37:13 to 40:34

Julie discusses the challenges and humbling experiences of building her startup, emphasizing the unpredictability of technology.

“So we're basically a consumer-facing search engine for fashion that links to all of the retailers and all of the brands out there.”

Leading a Startup Team through Challenges

40:35 to 42:00

Julie shares her strategies for leading her startup team through the ups and downs of entrepreneurship.

“competitive space is that it's very hard to predict what's going to happen, especially in today's world with AI.”

Leadership and Team Engagement

42:00 to 43:34

Learn the importance of transparency and leading by example in team dynamics.

“I mean, you've got that drive and you're optimistic and you're going to figure it out.”

The Rapid Evolution of AI

43:34 to 45:02

Discover insights about the fast pace of AI development and its societal impacts.

“first with, you know, the internet, and then with mobile really transforming the way we all use technology.”

Essential People Skills for Leaders

45:02 to 47:14

Understand why strong interpersonal skills are crucial for effective leadership.

“And so I just think it affects, you know, the psyche, the human psyche in a whole new way that creates a different vibe in the workplace.”

Recognizing Patterns in Business

47:14 to 49:18

Explore strategies for leaders to identify significant business patterns and trends.

“And we don't know, you know, what the future is going to hold in terms of like where industry goes.”

Risky Decisions and Future Trends

49:18 to 51:44

Learn from Julie's experience about making bold decisions in uncertain times.

“One of the things I do is I sit on a couple of boards and, you know, I find that the time away from my company is really hard.”

The Future of Retail

51:44 to 54:21

Gain insights on the enduring relevance of physical retail and its evolution.

“What's the belief that you have about retail and where it's going that maybe people don't quite see yet?”

Lightning Round with Julie Bornstein

54:21 to 56:01

Enjoy a fun and candid lightning round with rapid-fire questions.

“go away because when we need something specific, we go online to get it.”

Lightning Round Wrap-Up

56:01 to 56:46

Julie shares her daily rituals and personal fears.

“because I just made my daughter watch it with me.”

Insights on Loyalty Programs

56:46 to 59:11

Julie discusses the importance of service experience in loyalty programs.

“I I just got a few more questions and I'll let you go back to work here.”

Lessons from Motherhood

59:11 to 1:01:37

Julie relates how being a mother has enhanced her leadership skills.

“And, you know, speaking of leadership, what's a lesson that you've learned in your career that makes you a better leader at home?”

Future Aspirations and Impact

1:01:37 to 1:04:04

Julie talks about her goals for Daydream and her desire to give back.

“You know, you're going into your second year.”

Advice for Aspiring Leaders

1:04:04 to 1:05:01

Julie offers practical advice for becoming a better leader.

“What's one piece of advice you'd give to anyone who wants to be a better leader?”

The Importance of Persistence

1:05:01 to 1:07:16

David reflects on Julie's persistence and her journey to success.

“Most women on the planet have shopped at Sephora.com.”

Passion and Self-Awareness

1:07:16 to 1:10:01

David and Julie discuss the significance of passion in leadership.

“It's sort of like this, Kula, you know, Nike, Nike's commercials, just do it.”

The Power of Self-Awareness in Leadership

1:10:01 to 1:13:01

Discover how self-awareness shapes effective leadership through Julie's journey.

“up when she talked about, you know, her career?”
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Transcript

Automatic transcript. May contain errors.

0:00David Novak:Hello, friends, and welcome to another episode of How Leaders Lead with David Novak. Today, we have Julie Bornstein on the show. She's the founder and CEO of Daydream, which is an AI-powered fashion search engine. But online shopping isn't new to Julie. She's been at the forefront of retail for decades, leading big brands like Nordstrom and Sephora through the e-commerce revolution. Through every shift that Julie and her team has made, the thing that she keeps coming back to is this, people skills matter most, especially in the age of AI. Enjoy this conversation with David and Julie, and I will see you at the Debrief.

0:43David Novak:You know, I didn't realize this, but I guess it's been almost a year since you, almost to a day since you launched Daydream. That's right. The longest year of my life. It's the longest year in your life. How do you feel about where you're at right now? I mean, as most entrepreneurs feel, you know, it's never enough. There's still so much to do. But I think it's been really exciting. We've learned a ton in the first year. And I feel like we're still just at the beginning. Julie, growing up, I understand that you loved watching the Jetsons. I love the Jetsons, too. But, you know, what was it about that show that made you like it so much?

1:22I think before I realized it was all about technology, I loved the innovation and the futuristic idea of being able to get to people faster through flying, not having to deal with traffic, being able to talk to your friend by clicking a button and seeing their face. It was all the possibilities that innovation could bring and technology could bring. And I couldn't wait to have those things someday myself. I'm still waiting for, you know, the flying from our apartments, but I love the FaceTime.

1:53David Novak:Yeah, we definitely have FaceTime. And here you are, you spent your career helping millions of people shop better. I got to ask you, I mean, who's the toughest person in your family to shop for? Um, probably my whole family would say me because they say I know exactly what I want and have everything I need. So my whole family says I'm impossible to get a gift for. yourself okay you know you've had a remarkable career transforming the way people shop that's really what you you've focused on and and before we dive into your journey I want to go back to where it all began can can you share a story uh from your childhood that shaped the kind of leader you are today I would say probably the thing that shaped my leadership the most is being a middle child.

2:46I had an older sister and a younger sister. And they, you know, a lot of my parents fought quite a bit. And my sisters were also very outspoken. We were sort of a typical opinionated Jewish family. And I was the peacemaker. And whether it was sort of negotiating a conversation or finding a restaurant that everyone could agree on, I was very much sort of always aware of what everybody wanted and needed and figuring out how everyone could win. And I think that definitely relates to how I lead. I like to listen to different perspectives and figure out, you know, play some judgment on the different perspectives, but also figure out how we can all win together.

3:31I learned that when you were 10 years old, you would read Seventeen Magazine and then you'd

3:38David Novak:head to the mall and try to recreate the outfits that were in 17. What was different about the way your mind worked, even back then? Well, my mom tells me that as a two-year-old, I was very opinionated about what I wanted to wear. So I think style and interest in it is somewhat innate. And I always had a real interest in it. And, you know, to me, sort of like what you wear expresses who you are and helps think, you know, how you feel. And so I was just always really drawn to also beauty and aesthetics. And so I think that was innate in me. And then, yes, I was always interested in fashion. When I was young, I wanted to be a fashion designer and I would draw.

4:21I also built a little business around making barrettes and selling those. And I knew every corner of the mall. I spent my weekends there. And I knew when a product became popular and it was in the magazines, it would take another six months to actually hit the mall in Syracuse, New York and be able to buy it. But I was definitely someone who was always aware of what was out there, really interested in it, really interested in the new things. You know, I remembered, you know, exactly what I laid out as my outfit in fifth grade to wear for the first day of school.

4:54David Novak:That's great. And you were an entrepreneur even back then. you started a barrette company? You know, just tell me about that. That's kind of a great idea. Well, so I was always like good at doing my friend's hair. And so for summer camp, everyone would come to me and I would braid their hair and I would cut their hair. And I love, you know, a new trend came around, which was these braided barrettes. And so I figured out how to make them. I still don't understand how we did many of the things we did before the internet, But, you know, someone taught me and I learned how to do it. And then I made them for my friends and they loved them.

5:28And so I started to sell them as a little business.

5:30David Novak:Guys, you're just a born entrepreneur, you know, startup as a kid. You know, one of my favorite stories that I learned about you is that early in your career, you really wanted to get in touch with Howard Schultz. Can you tell us that story? So I met my husband in business school. He got a job early on at Amazon, actually. he met Jeff Bezos when he came to campus and ended up driving him to the airport and getting a job in that ride. So that was fascinating. And I had taken a job in investment banking, working with retail and consumer companies in San Francisco. So I really wanted to move to Seattle because Brian loved his job and investment banking was clearly not my long-term gig.

6:11And as I looked at the companies that were there, Starbucks was the most exciting to me. Nordstrom was the other exciting company to me, but I had heard that it was run by the family and you had to have worked on the shoe floor since you were 12. So it didn't even seem like an option, whereas Starbucks seemed like a very dynamic, really amazing brand and company. So I heard that he was speaking at an event in Seattle. So I read his book over the weekend. And of course, I loved Starbucks, like, you know, everyone did. And it was this was in 1997. And so I went to hear him speak. And I waited in line to talk to him after he spoke and basically just went up to him and sort of took all the guts that I had and said, I would love to work for you.

6:57And he said, well, you know, who are you and what do you do? And, you know, what do you want to do? And so I told him that I had worked on a deal at my investment bank that was in the coffee space. I told him about that, which interested him. And then I told him a little bit about what I wanted to do. and he said, well, send me your resume. And so I flew back home down to San Francisco, faxed him my resume and got basically, hadn't heard from him about a week later. So I called his office and his assistant said to me, oh, he's actually interested in meeting with you. So we set up a time and I got a chance to go meet with Howard Schultz.

7:36We spent over an hour talking and then they were trying to build a couple of new businesses. And so I got hired for one of those businesses.

7:45David Novak:You know, a lot of people wouldn't have the gumption to, you know, stand in line, you know, ask for that opportunity. You know, what is it about you that that gives you the kind of courage to do things like that? And and what advice can you give to others on how to do something similar? Yeah, I mean, I think throughout my career, the the thing that I learned is the hardest part is figuring out what you want, because there's so many things out there. And as a young person, it's so hard to figure it out. And I always tell young people, take something that just really interests you. Don't worry about what the end game is because it's so hard to know.

8:23And with each job you take, you learn what you like and what you don't like, the kind of people you want to work with, the sort of skills that you have naturally and what you really shine at. And so, you know, for me, I had had a few jobs leading up to this moment. I looked at Starbucks and I knew that it was a company that I wanted to work for. And so my feeling about everything in life is you have to create your own reality. And, you know, no one's going to do it for you. And so I knew that I wanted to work at Starbucks. I had the benefit of being limited to a certain town because I wanted to move to where my boyfriend was.

8:59And so I just had to like, you know, get the courage up. I did feel like I had context. I read his book. I had sort of prepared, you know, a little bit in my mind what I would say. And it's hard to put yourself out there. But if you don't, you will never know. And so I think you prepare as much as you can, but you do everything in your power. And my next set of jobs were also sort of the same way. You figure out whatever it's going to take to make your reality happen.

9:26David Novak:Yeah. And you mentioned Nordstrom's was another company you really admired that was in Seattle. And you said, you know, you basically had to work on the floor since you're whatever age or be a part of the family to be successful. Yet, somehow you made your way to Nordstrom and had a heck of a run there. How did that happen? So I had a terrific couple of years at Starbucks. But what I realized is I was doing corporate dev business development. And I realized I didn't want to do that. I really wanted to be more of an operating role. And at Starbucks, the interesting jobs really were in the field.

10:04And that was sort of running a store. and that wasn't quite the life I wanted to lead. And so I started to think about what I wanted to do next. And e-commerce emerged as a category. And I was obsessed from the day that Amazon actually launched and was selling books, which was what they were selling at first. I thought this could be so interesting for fashion. And what happened was during the time I was at Starbucks, a few fashion companies started to emerge on the internet. And I just had a million ideas and I knew that's what I wanted to do. So I was, you know, stuck in Seattle for better and for worse.

10:38And I thought, I really want to do this. And I started to talk to a startup. And I was talking to a guy who didn't know what the hell he was talking about. And I certainly didn't feel qualified to start a company to raise the money. I didn't have the access to the capital. And so Nordstrom was really actively going after this space. And as soon as they announced that they were launching e-commerce, I knew that's what I wanted to do. So I basically spent six months trying to convince Dan Nordstrom to hire me. I used every connection I had to him. When he kind of ignored me, I came back and I said, I have some ideas for you.

11:11And I basically had to create the job by describing to him what they needed to have, which was this sort of product management function, which was brand new in 1999, and explained to him why it would help, what I could do. And then, you know, I basically used my connections through my husband, a friend of his, knew an investor. So I sort of worked that route. And eventually, Dan Nordstrom couldn't get rid of me and hired me.

11:42David Novak:And good thing you did. You took a business, an e-commerce business, from$10 million to$350 million in a very short time. And, you know, when you see that kind of growth, what belief did it reinforce that you've carried with you as you moved along in your career? The main thing that it reinforced was if you are the customer and you know what the customer wants, it gives you such an advantage in building an experience. So I was so the customer that we were targeting, and I had so many specific ideas of how I wanted the website experience to work and what I needed to be able to buy online. And I was able to firsthand really sort of translate that experience to the product team, to the engineering team, to the creative team.

12:35I hired other people who also really understood innately what the experience was they wanted. And so we were really able to build something that we knew was needed in order to get people comfortable with buying online because we were still back in those days. I also needed to be able to go to all of the vendors that sell, the brands that sell to Nordstrom because we were a separate division and Nordstrom Inc. didn't want anything to do with this sort of like little fledgling division of the dot-com and convince the brands to sell to us online too. And so that was kind of being able to paint a picture of what the future was going to look like, which I had a very clear sense of as a consumer with what I wanted.

13:18And I would say, you know, both of those experiences really underscored for me the ability to really understand your customer and be able to express that in a way that's compelling to others. And whether it's to convince Nordstrom Inc. to give us the money we needed or to convince the brands to sell to us, all of that was really helpful to be able to paint the picture to these different constituents.

13:42David Novak:And that's obviously a towering strength that you have, and you've made your way to Sephora. And I understand the former CEO said that they ought to build a statue of you and put it outside of the headquarters because of the impact that you had on the company. Tell us your favorite leadership story from your time at Sephora. Yeah. So David Slitianu, he was an exacting person and not everybody loved working for him. He would say that himself, but he was incredible, incredibly sharp and, you know, incredibly insightful. And it was the year 2009 and the market was really in the doldrums. So this was, you know, the recession and basically the housing crisis, which led to consumer confidence and consumer spending way down.

14:39And every single company was rethinking how they were going to keep their business alive. And David basically pulled the entire company together and came up with seven things that we were going to do that year that was going to help the company survive this, you know, decrease in overall business. And they were so clear. They were simple. And he used metaphors and stories to make each of those points so important. They were all resonant across the business, whether you're in the store, in corporate headquarters, running the e-commerce, you know, side of the business. And it really helped the whole company rally around what we were going to do to basically survive this challenging time in retail.

15:27And it was so clear. And then every month we would get together and we would revisit these seven principles. And we would talk about examples that basically helped the business to do these. And it was really just an experience for me of when times are tough, you know, it's the best time to actually pull the team together and focus and stop a lot of the things that didn't matter and feel really empowered and excited by the things that we could control.

15:55David Novak:So what did you do at Sephora that is statue worthy? I mean, you know, when you look back on that, why would he say that that's such a compliment, you know, that they should put a statue of you outside the building? Well, I got to Sephora and there wasn't an e-commerce division. We were, you know, marketing was run by the corporate marketing and merchandising was run by corporate merchandising. And there was no one who was really saying, here are the next things we could do with technology and sort of digital capabilities to make the experience better. The second thing that happened was when I got there was we had the idea of a loyalty program and we were about to launch it, but we didn't have the specifics or people to run it and how it was going to roll out.

16:38And so those were my two challenges when I got to Sephora. How do we actually build an e-commerce business and sort of modernize the way that we were thinking about customer interaction as Facebook was becoming a thing and as Google and YouTube were becoming a thing? And we were starting to get tons of feedback from customers through these new channels. And we basically needed to rebuild an e-commerce site so that it could basically grow and allow us to not only sell product, but make it a much more dynamic experience. We also had to launch a loyalty program that was going to resonate both in-store and online.

17:18And so in the next, I guess it was eight years of being there, we did those things. We built the most successful online beauty business. We incorporated all the learnings of what was happening on YouTube by pulling videos into the site. We understood that mobile was becoming an important mechanism. And I basically educated both the company as well as corporate, so LVMH, who owned us, on why mobile, both webs and mobile apps, were going to change the way we all shop and the way we think about things. was going to become a bridge from e-commerce to the store. The customers don't care where they're shopping.

17:58They want the same information. We launched Beauty Insider, which was one of the most successful loyalty companies ever and used as an example by lots and lots of other retail companies on what to do. We used the customer's love for beauty as our currency. So we gave product based on how many points you had. We understood that like our best shoppers, which we called, at first we called them VIBs, very important beauty insiders. And then VVIBs, we had like top tier, we created experiences for them. And we sort of, you know, I think understood their love of beauty and really leaned into that. So we really sort of modernized the company to create a very sort of digital and store experience that felt like one.

18:41And what we were able to do is create incredibly loyal customers who felt like We were actually leveraging technology to make their life better. You could scan a product in a store and read the review of it. You could walk into the store with your phone and remember the color foundation that you love to buy. And I think that there were just so many, we did so many really interesting, both digital things that actually helped people and also really thought about what that store experience coming back to the site should be. So we grew our business dramatically. We grew our web business to a billion dollars.

19:17We doubled our store business in that period of time and became really the leader in what I would say, you know, multi-channel retailing during that time period. And it was a lot of me and my team, who was amazing, nothing is done alone, as we all know, you know, really sort of trying to express before, ahead of the time, why this was going to be so important.

19:41David Novak:And that's what I want to ask you about, Julie, because, you know, you really are a trailblazer. I mean, you wanted to get into e-commerce. You know, you mentioned you started out banking, you go to Starbucks, and then you realize you have this idea of what you can do at Nordstrom. And then, you know, you just talked about how you really pioneered the whole digital loyalty transformation at Sephora. How did you educate yourself on even how to do this? I mean, you know, how did you get prepared to do what nobody else was doing? I think that mostly I'm just an early adopter. And so I was playing with the technology and thinking about how it could be used for other purposes.

20:24And so, especially because fashion is such a passion of mine and I love it so much, I'm thinking about it all the time naturally. And I'm also always thinking, I'm sort of an optimizer by nature. So I'm thinking, how can you do this better? How can you do this more efficiently? I love the idea of like marrying those two things and technology is the ultimate efficiency driver. So what I think about when I was 10 and the first version of a portable TV came out and I just was obsessed with that. And I saved my money and I bought it and I was going to bring it to camp where no, you know, it wasn't like people were told, don't bring tech to camp.

20:59Like there was, there's no tech. So no one was bringing anything. Like my bringing this was really exciting for everyone. And I just think I've always been really interested in it. So, you know, I remember that literally where I was sitting the day Amazon went live. I mean, Jeff Bezos is really, you know, the pioneer of it. What I did was took like his, you know, initial ideas and then thought about all the things you could do to make shopping, especially for fashion and beauty better. And so I am constantly, I'm sort of a problem solver by nature. And to me, technology is like the ultimate way to solve so many problems.

21:30And so that sort of naturally all comes together in my mind.

21:34David Novak:Now, you left the Sephora, you didn't get the CEO job there. In looking back now, Now, what did that ultimately open up a door for you? You know, sometimes, I don't know if you wanted to be CEO or not, but you didn't get that job. But, you know, because you didn't get it, what opportunity did it give you? When I was at Sephora, sort of later on in my time there, the head of marketing left and they said, Julie, why don't you also take on the CMO role? And at that time, David announced that he was leaving. and because I had just taken this new role as I think a factor in it, they brought on someone else to be CEO and I just, you know, I felt a year in that this was not the sort of the place for me to stay, that I needed to go out and find something else and I think in some ways, you know, it would have been incredibly fun to be CEO of Sephora and I'm so proud of the fact that one of the women that worked for me while I was there is now the CEO, Artemis Patrick.

22:33So she's amazing. And I, you know, I think that there are a lot of things that we did during our time that probably helped her to become CEO. So I'm proud of that. Mostly proud of how amazing she is. But, you know, I would say that that really led me to think, OK, what do I want to do next? And I had always wanted to start something. But I was nervous. I'm, you know, not a millennial. I'm not a Gen Z. I'm a Gen Xer. And so the idea of going out on my own and starting something still felt a little bit scary. and I had been on the board of Stitch Fix and I had really gotten to know Katrina Lake, the founder, well.

23:05I had loved that experience, was very involved. And she said, when I was thinking about leaving, why don't you come work for us? We have so much we need to figure out. You know, the business had so much potential in front of it. I knew everything about it and I loved the business. And so I thought, you know, this will be a great way for me to figure out if I wanna go start my own company. And so it was an incredible experience. I'd been on the board for two and a half years. I came in, you know, we had grown. It was an incredible growth story, that company. So at first we, during the time as a board member, we grew from about 10 million when I started to about 250 million.

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23:41And then I joined and over the next two and a half years, we grew the business to a billion. And that growth was so exciting and was a result of many people and many conditions in the market, really. I think you realize over time, there's definitely a lot of luck with this thing. And so that was really an incredible experience and really, I would say, confirmed everything I thought about starting my own business. And so that was what gave me, I would say, the courage, frankly, and the experience I felt I needed to then go start my own company.

24:13David Novak:Yeah. And I want to get to that in a second. But when you were at Stitch Fix, you really helped scale the business. You just talked about the dramatic growth. Yet you left before the IPO. What made you not stick around for the IPO? There were a couple of factors. One is that I knew I wasn't going to stay. And it's really hard as a top executive to leave right after an IPO. It really leads to all sorts of questions. So we knew if I was going to leave that it should be before the IPO. It was really hard to leave then because I was so excited after having helped build the company to not be part of that.

24:55I also think that Katrina and I kind of came to a realization that she was going to stay. It didn't make sense for me to stay. We were sort of at a point where we were, I think she had left on maternity leave. I co-led the company with Mike Smith, who had been there for a long time. I loved doing that. And then, yeah, just became clear that she at one point was thinking she might leave, decided to stay, and it was really time for me to go and do my own thing. Years later, after she decided to leave, she reached back out to see if I was interested in coming back. But at that point, it didn't make sense.

25:31So, you know, it's interesting with life, the way these things work.

25:35David Novak:Hello, friends. I hope you're loving this conversation. Be sure to stay tuned to the very end of the episode. As always, David and I are going to debrief some of the concepts that he talks about with this week's guest. So stay tuned to the very end, and I will see you soon. You know, you once said that the job wouldn't be about creating something new. It would be more about managing decay. What did you mean by that? Not at Stitch Fix. That was sort of the idea of going to another big company at that point. Oh, OK. All right. Yeah. So, you know, I was sort of at that moment, I was actually, when I announced that I was leaving Stitch Fix and I was starting to work on my startup, I also got approached by a couple of big companies for the CEO role.

26:16and some companies that would have been, you know, a dream to run those companies. So I spent some time as I was thinking of starting up, do I want to go do that? I'd always wanted to be the CEO of a big company. And so that would have been a real checkbox of my dream. But what I realized over the years was that that actually wasn't my dream. My dream was to start a company. I just didn't really know that until this point. And so that was a great opportunity to test out, you know, which direction I wanted to go. Such different directions. But what I realized in going to these larger companies was that they had so many headwinds and there were the focus of what I would be doing was, you know, to some degree, managing decay and other, you know, in other ways, trying to figure out how to transform.

26:57But it would not be leaning into the things that I love to do most and that I was best at.

27:02David Novak:Yeah. And, you know, so you were at that point in time in your life where you had to figure out which fork to go down. You decide that you're going to be the entrepreneur. You're going to go the startup route. and you create the yes, you know, you know, that takes a lot of courage. I mean, you know, you know, what, what was it that the, what was it, what was the tipping point that made you say, hey, I, I want to run my own thing versus go to the established company. I know you, there are all kinds of challenges with that, but you know, how'd you get the courage to go start the yes. Yeah. I mean, I think that it's hard for a senior exec who has a cushy job in a corner office and, you know, all of these things to suddenly switch gears.

27:48And, you know, I remember talking to an investor and he was saying to me, well, you're not going to really be like in the day to day, right? Like you're going to kind of oversee it. And I was like, oh no, I'm going to be in a day to day. I'm going to be building. And, you know, what I realized is, first of all, It was very helpful to have Stitch Fix as a transition because I really got to sort of live the startup experience, which is very different from corporate life. And it was very helpful both as a board member and even being inside to know what it was going to take. I would say the reality was the thing that I loved about my corporate jobs was actually the new stuff that we were building and creating.

28:26And that's what I was best at. And so I realized that, number one, I liked to build from scratch. And number two, that I was making lots of money for these big companies. And I would much rather be the person that owned the business that I was creating and, you know, hopefully succeeding at. So that was a motivation. But it was scary. I mean, I was 47 when I started The Yes. And I felt like, am I too old? People said, you know, you shouldn't start a company if you're not young. And you just don't understand, like, you know, the thinking. and so I got some skeptical people, although the main person that told me that ended up investing in my company.

29:05So, you know, at the end of the day, I'm not sure he believed it, but he was sort of saying it as a challenge. And, you know, you're exposing yourself. Like any artist, you know, who goes out there and writes a song or writes a book or creates a podcast like you, you put yourself out there in a way that's very different. And so, you know, you're like, are people going to like this? Am I going to be able to get higher people to work with me? There's so many questions And it really was incredibly nerve wracking, but I'm so glad I did it.

29:32David Novak:And just days after the launch of the, yes, COVID shuts the world down. I mean, what was going on in your mind when that happened? So interestingly, it actually, we were about to launch. So we hadn't launched. We were planning to launch on March 20th and COVID kind of, you know, became a known thing around the first week of March. And so I kept thinking, because I'm the ultimate optimist, which you have to be if you're an entrepreneur, because otherwise, you know, you would just see all the problems and you couldn't move forward. I always assumed things are going to work out. And so I said to my team, oh, let's just wait three weeks, a single pass, and then we'll launch.

30:09So we held off on launching. And during that time, the good thing was there were still a bunch of things that I really wanted fixed before we launched. So we got a chance to fix those things. But you know, three or four weeks in, it was very clear that COVID was not going away anytime soon. So we kind of retooled and we figured out what would be the right time to do it. It felt very sort of out of place because it felt superfluous to think about shopping for clothes during this major pandemic where people were getting sick and dying and there was, you know, the whole world was shut down. So we really had to sort of change the way we thought about it and make it about entertainment and a little levity.

30:44You know, this is something to play with while you are sitting at home, bored, scared, stressed, whatever you were doing. The other thing is we needed to find the right moment in time You know, as you remember, there were a lot of things that happened during COVID. And so we needed to find kind of a quiet moment where we weren't stepping on the toes of something that was much bigger to get some publicity. So anyway, we ended up launching in May and we got lucky because it happened right before a lot of other terrible things happened. And we had a moment where we had some space in the media to launch.

31:18And then we learned how, as every company did, how to pivot and work from home and continue to build and create an audience and a product in a very strange world.

31:29David Novak:And, you know, Pinterest ends up acquiring the yes. But I don't know that things really played out the way you'd hoped there. You know, what happened and what did you learn from it? So much learning. Um, we were not looking to sell the company. We, this was two years then after we launched, it was 2022. And, uh, we were just starting to get traction and growing and we were going to go out for our next raise. And I got, uh, outreach from Ben Silberman and his head of product, Naveen, and they were really interested in what we were building. And so we started to talk and I said, I'm not looking to sell the company, but I love Pinterest.

32:14I always have. I actually remember exactly where I was when I learned about Pinterest and when I started to use it. So it was exciting to hear from them. We had had calls from a lot of the tech companies over the couple of years. There was a lot of interest in what was sort of evolving for shopping, how to sort of create a layer that didn't require owning inventory, a tech layer that could help match people with the right product. And so we were just in women's fashion. So we were pretty narrow at that moment, but it was, we were interested in, you know, sort of what was happening with the social media space.

32:47And when we got the call, I was intrigued. So I started to talk to Ben and he is great and was really interesting and had lots of interesting ideas around what he wanted to do with Pinterest. He had always thought about making it more of a shopping destination and not just kind of a search and browse destination, but he hadn't had the right person to sort of build out shopping for them. And he had loved what we built at the Yes. He could tell that we had built something that was really for the user and really well thought through. And so we had great conversations and lots of plans on how to work together.

33:22And they were willing to pay the price that made sense for us to do this deal. And so we did the deal. And it was kind of a crazy moment. I learned how hard it is to be patient during an M &A process. and I learned a lot about the M &A process, which is really interesting and useful. But then we closed the deal and we started to work together. We did a town hall. It was really exciting. All of Pinterest was thrilled to have the Yes join them. And about a month later, Ben announced that he was stepping down and I was very surprised. I had no idea that was sort of his plans. And then a new CEO was announced.

34:00And unfortunately, as often happens, the new CEO had a very different agenda. He was very interested in building onto the ads business. And so he was not interested in building a shopping surface. And so we spent some time talking through. I tried to see if there were, you know, I could change his mind and I couldn't. And so it was really hard, I have to say, from an emotional standpoint. We were so excited to build this idea and vision that we had. And so in the end, I stayed for six months. And as an employee, I helped find roles for my team that was all there that would make them useful in the new direction.

34:43And I stayed on as an advisor for six months and was helpful where I could be. And during that time, ChatGBT launched. And I had a whole new idea for the next wave of shopping and started to think about what I would do next. But it was a really interesting experience. I would say financially, it was a great opportunity for me and my team. And so I'm very thankful for that. You know, I think Pinterest was able to use the tech we built in many ways. So that was a great experience. But I definitely learned that you cannot predict what's going to happen after a deal closes.

35:19David Novak:And then it really led to this new idea that you have. And so tell us about Daydream and what makes it different. So one of the things that I had always seen in e-commerce is that about quarter of the population uses search when they're on a site to find what they're looking for. Search has traditionally not worked great on e-commerce sites and especially on apparel and accessory sites. You know, if you don't use the right terminology, then the right product doesn't show up. So we've trained consumers kind of to be suspicious of search and really rely on more of the navigation to find the things they're looking for.

35:56What happened when ChatGPT launched was that it started to train users. Not only could you actually use search to leverage this new form of technology to find what you're looking for, but you could go beyond sort of simple terms. Like instead of red dress, you can say, I'm going to a Valentine's Day party and I want to look sexy. And, you know, I definitely need to wear sleeves. I would like something with lace. Show me what you got. And no one had ever searched for fashion that way. But that is how we think as consumers. We have a need, we have some desires, you know, about how we want to look.

36:33And to me, especially in fashion, that is such a big unlock. And so I got really excited what ChatGPT would do on two dimensions. One is obviously using LLMs to marry to search and be able to actually create a dynamic search that understands natural language, understands the user, and understands the product so we can actually show users the right products for them. But also, we were training users now, instead of keyword search, that they could actually use these prompts that express what they want. And both of those things were enormous unlocks for creating sort of the next generation of a shopping experience.

37:09And that's really what drove me to launch Daydream.

37:12David Novak:How does the business model work? The business model works. So we're basically a consumer-facing search engine for fashion that links to all of the retailers and all of the brands out there. And you as a consumer can come on and search for anything you want. When you find something, you can either go see who sells that product and link out to those sites, or you can say, I like this product, but it's not quite right. It's too expensive. It's too low cut. It's not the right color. And you can tell the agent, you know, I like this product, but I want it in orange. You know, you're looking for a short sleeve Henley, but you want a color that's going to pop.

37:49And that's kind of a, you know, maybe a common style in greens and blues, but is there actually an orange out there? And so you can take the product and you can say, I want this, but an orange. And then you can find what you're looking for. And so some of those tools, the ability to combine text and image to find what you're looking for is quite powerful in fashion because it's such a nuanced category. And so then once we find your orange short sleeve Henley shirt, you can see that you can buy it at Nordstrom or you can buy it directly from Faraday or whoever makes it. And so you'll see the prices at those places and you can click out and you can go buy that shirt.

38:25So we make money when the retailer makes money and the consumer finds what they want. Once we actually learn about you, the more time you spend on Daydream, the better we understand your preferences. And so the search results become more geared towards you and the whole thing becomes more personalized and easier to shop. So that's the premise of the business. We're doing a lot of additional things as well, but I'll stop there.

38:48David Novak:That is great. You know, and I've talked to a lot of founders, Julie, and, you know, every founder talks about what what they learn, you know, when when they start a start a new company. What is, what's Daydream teaching you right now that you didn't know when you started it? Well, I would say, first of all, there is nothing like trying to build a startup to keep you humble. You know, I think that we are very, you know, we have successes and then we think, okay, we can do this. We're really talented. We're really capable. And then you start a company and, you know, one day is up and the next day is down.

39:29and it is an emotional rollercoaster because there are so many little wins and losses all the time. So I would say if I didn't have enough humility before, definitely it has taught me humility. But I would say the other thing is just there's so much unknown. And so I have always been a huge believer that people kind of know what they want. They may not know exactly what they want, but they know what their needs are. So whether it's, I need a dress to look great at a wedding in Austin that's a daytime wedding this summer, or it's, you know, I want a very specific thing. I assumed starting with search would just blow people away.

40:09They would come in droves, they would tell each other about it. And, you know, this would be on fire because we really are the best search that exists in the fashion space. And while we're definitely not perfect and we get better every day and every week, it's the best thing out there. And what we've learned is that's not enough. We need to build more capabilities, more tools, find new ways to drive users in. And it's been really humbling. And what I would say is also the other piece about working in technology and working in a competitive space is that it's very hard to predict what's going to happen, especially in today's world with AI.

40:44It is changing so quickly. One of the things that's really interesting about working with an LLM, a large language model, and you relying on that to sort of power what you're doing is that it's non-deterministic. And so you can type the same thing two times and get different answers, which makes for building a consumer experience really hard. And so, you know, there are a lot of parameters you have to build around it. And so building the technology for this product has been so much harder than I expected. And I have really talented engineers and machine learning people working on the team. So I think that has been very humbling is just how hard it is to build a consumer experience on top of a new technology that is still being understood and improving and changing every day.

41:28And sometimes you think, you know, if you're building a technology versus a physical store, let's say in retail, you know, it's easier because you don't have to be out there sweating, you know, blood, sweat and tears, but there are more controllables in the physical world than there are in the technology world. And so that's been a really interesting experience more now than ever.

41:46David Novak:And you have this, you know, as you mentioned, when you have a startup, it's a roller coaster ride, You know, and how do you take people with you on that ride? I mean, you know, how do you get your team to have that perseverance that you as a founder, you obviously have? I mean, you've got that drive and you're optimistic and you're going to figure it out. I mean, you find a way. I think by being honest and transparent and being in it with them. I mean, I definitely am a big believer in lead by example. I don't ask my team to do anything I wouldn't do. You know, I'm in there with them solving problems.

42:23We had this amazing experience to do a project with Apple. And, you know, I was right there with my team building these new things that were exciting and hard. And so, you know, I think and sharing with them my fears and sharing with them the hard things and not kind of sugarcoating things and not pretending when, you know, we see something that doesn't work, that it works. And so, you know, I think that keeping an eye on where we want to go and the problems we're trying to solve and what the vision is, but also being really realistic about, you know, trial and error and making it feel OK for people to take risks and try things, even if they don't work.

43:02Those are kind of, I think, the most important things for keeping people engaged and motivated in a startup world and also making sure they have, you know, they have skin in the game. I mean, equity is a cornerstone of being able to get everybody as excited and feeling like they're owners in this process.

43:19David Novak:The world is changing so fast. AI is changing so fast. You know, when you look back at the last five years, Julie, what do you see happening today that you could have never possibly even imagined, you know, happening five years ago? Well, first of all, I would say that this pace of change is so much faster because I think about the first wave and the second wave of technology change. first with, you know, the internet, and then with mobile really transforming the way we all use technology. And, you know, I see this as the third wave of AI, and it's just, it's the pace of change is so much faster.

43:56But the level of unknown is also so much higher. And so what I see is just a lot more stress. And, you know, across the board, how do I work with this thing? I'm supposed to use it? What does it mean? I'm supposed to be working smarter. I'm supposed to be creating new things that suddenly transform the world. And so I think, you know, obviously I would have never expected a model to be able to answer the kind of questions it can answer when you go to ask an LLM. Like, you know, people who are much more deeply technical, they saw this. They saw this 10 years ago, 20 years ago. I don't have that insight.

44:30So certainly I'm blown away by what, you know, what we can teach these models to do and the learning, the speed at which they're learning. But I think the thing that really surprises me the most is the level of anxiety that this has created among literally every human. You know, I think that it really is quite different in that regard. Like there wasn't a huge level of anxiety when the internet created and when mobile was created. There was like, cool, I like this. I want to try it. But with AI, it has so many unknowns. And so I just think it affects, you know, the psyche, the human psyche in a whole new way that creates a different vibe in the workplace.

45:11David Novak:For the young leader, you know, watching this, what skills would you spend the next five years becoming great at? I mean, I think that the people skills always matter the most. unless you are building your own company and you are going to be the only employee, understanding how to work with people, communicate, hire, fire, motivate, those things are always going to be the most important because no matter what you're working on, you're working with a team. And, you know, one quick story from like the past when I was at Nordstrom and I was a young, very eager beaver, I got pulled aside by some senior people and said, like, you are stepping on people's toes and you are pissing people off.

45:54And if you don't figure out how to work better with your peers, you're not going to be here. And it was the most embarrassing thing I had ever experienced in my life. I was mortified and I was so ashamed. And I realized in that moment that learning to work with people who worked for me, who I worked for, and most importantly, who I worked with was so critical. And I really sort of attribute that moment to my success at Sephora, really realizing that I was working on one thing, but my thing could help everyone. And so we should all be looking at this and working on this together. And I think the best advice that I give people is, you know, put yourself in the shoes of your boss and the shoes of sort of the CEO and think about what they would want done and behave that way.

46:43Because when you are focused on your own little world and trying to make your fiefdom succeed, you are not actually thinking about the whole and really building the relationships across the team, no matter how small or how big it is. So helping others has always been like at the top of my values list. And I think that it's really ties to sort of the skills that we need for the future, which is learning how to work well with other people, because we have no idea what the actual technical skills that are going to be needed are going to be. And we don't know, you know, what the future is going to hold in terms of like where industry goes.

47:21And I just think whether you're in the nonprofit world, you're in the business world, you're in the legal world, you're in the medical world, all of those things, of course, are going to need technology. So pay attention. Don't be a lot of, you know, jump in there, try stuff out. But ultimately, I think focusing on how to build good relationships and motivate those around you, no matter where, you know, what position they sit in is always going to be the most important skill in the workplace and in the world.

47:48David Novak:You know, you mentioned earlier, you look at patterns. You talked about looking at Amazon and seeing what they're doing and then figuring out what you could do in the world that you're in. You know, that's pattern recognition. That's an important skill. What advice could you give leaders on how to get better at recognizing the patterns out there that could influence your business or help you identify something that isn't being done today? I find that the best way that I am able to detect patterns as a leader is actually by making sure I'm not like sort of only focused on my own thing. So getting out there, talking to other people, both in your industry and even in other industries, and, you know, talking to customers and like reading things.

48:45It's these moments where you kind of start to see things that you then can realize the patterns. And, you know, I think being someone who sees patterns and recognizes them, that's probably more of an innate skill. And most strong leaders probably have that because it's such an important skill in growing in your business and rising the ranks. But I do think that you're not going to see the ideas that then lead to patterns if you're not actually out there paying attention to things that are happening outside of your world. One of the things I do is I sit on a couple of boards and, you know, I find that the time away from my company is really hard.

49:26But I also find that the things that we talk about tend to be things that even though it's a totally different industry actually relate back to the things that are important to my business. And I always come back not only with, you know, of course, ideas for that business, but also ideas for my own business. So I think you have to be out there listening and learning to make sure that you're pulling from all sorts of places that can be helpful.

49:50David Novak:Can you think of a time when you recognized a pattern that led you to make a decision that everyone else thought might be pretty risky, but to you, you looked at it and said it's a no-brainer? I mean, it was just, it's completely obvious given what was going on? I have a couple. I'm going to actually pick my decision to go to Stitch Fix. So I was in an amazing job at Sephora. Our business was doing really well and, you know, only had like, you know, there was so much more to do. And I chose to leave and go to a startup. And what I could see was that we were at the beginning of basically being able to use machine learning and pattern recognition and data to actually create better consumer experiences.

50:40And, you know, we all had Netflix. So we were starting to see that. At Sephora, I was seeing that when we actually could get data on what a customer was doing. And keep in mind, this was 2013 to 2015. And we knew about the customer, we were able to basically put the right content in front of her to make it feel so much more relevant. And she was so much more likely to act on it because it was, you know, so much more personal. And so what I saw in Stitch Fix was this idea of building personalized user experience that could materially improve the satisfaction of the customer. And that was pre-gen AI.

51:23And, you know, that is what then led me to start my own, you know, AI-powered experience and recommendation engine with the yes. And I think that I saw that early because it was so clear to me that we were doing kind of a one-size-fits-all experience. And that just wasn't where the future was going. So that's an example.

51:46David Novak:What's the belief that you have about retail and where it's going that maybe people don't quite see yet? I truly believe that physical shopping is here to stay. I think that it is, you know, it's going to markets and as an outing is a pastime since the beginning of man. And as someone who loves to shop in physical stores, you know, I think it's very important. It's important to touch and feel, and it's a whole experience. I do think that retail is in big transition. Having these huge stores with tons of inventory and so few customers is a very hard situation to justify. And so I do think that being able to figure out how to get the right inventory and the right amount of inventory into a space, whether it's in hardware or it's in clothing or in any other category.

52:44Being able to make that in-store experience actually not frustrating. It's a low bar, to be honest. You know, there's still so many frustrating experiences where you walk in, you can't find what you want, you can't find help. Apple's at the standard. I think Nordstrom's also amazing. You know, we have to make those investments make sense. And so I think it's going to take another 10 years, to be honest, until we sort of right-size the physical box and what we're doing in it, understanding the impact it drives to online and the impact that online drives to offline and being able to make that financially make sense by looking at the whole thing.

53:20So whether it's using the inventory in the store to ship to people and making that cost-effective, which Nordstrom's done a great job of doing and retailers are more and more doing this, that makes a lot of sense. Your store in some cases can also be a warehouse. But I think that my hope is that retailers really figure out that it's worth it to invest in making that store experience great. So people have a good experience, can learn what they need to about the product, can build that attachment to the brand or the retailer. And, you know, in a world where, you know, everyone has so much coming at them at every moment, and it's so hard to sort of like actually land an idea or an experience with somebody, physical retail is an amazing way to do that because you're actually getting that time and that attention.

54:08And hopefully, you know, everyone who spends money to have physical retail will understand the importance of that experience so that they make that touch point really count. And then, you know, I think leveraging online is never going to go away because when we need something specific, we go online to get it. You know, when we're looking for something in general or looking for a pastime, we go to a store and that sort of dichotomy needs to be thought of as one overall experience.

54:35David Novak:And daydream is going to be the experience that makes it really easy and easy for you and something you as a consumer you've been looking for forever. It is. I believe that. You bet. And this has been so much fun. I want to have some more with my lightning round of questions. So are you ready for this? Okay. The three words that best describe you? Tenacious, loving, and helpful. If you could be one person for a day besides yourself, who would it be? Probably Oprah Winfrey. Your biggest pet peeve? People not doing what they say they're going to do. Who would play you in a movie? Jennifer Aniston.

55:12David Novak:We talked about the Jetsons earlier. What's one invention from that show you still wish existed? Being able to fly my car or my motorcycle. What's something you've been curious about lately that has nothing to do with work? I am really obsessed with reproductive rights and access to women, for women everywhere. I think that bodily autonomy is like the most basic form of freedom. And so I've spent a lot of time learning what's going on in states where abortion is outlawed and seeing how I could help. The one thing you do just for you? Hang out with my kids. Besides your family and friends, what's your most prized possession?

55:52David Novak:Sephora.com. If I turned on the radio in your car, what would I hear? Well, you'd hear today, you'd hear a song from Fame because I just made my daughter watch it with me. Great. What's something about you few people would know? I'm totally afraid of scary movies and you couldn't pay me money to see a horror movie. So scream is not in the future, huh? Okay. What's one of your daily rituals, something that you never miss? every morning I have a cup of coffee and a bagel. And no matter what happens with protein going up and carbs going down, I love a good bagel. And it's sort of like my moment to think about the day ahead.

56:36And yeah, I sort of really enjoy that, you know, five to 10 minutes of eating my bagel and drinking my coffee.

56:43David Novak:That's great. All right. We're out of the lightning round. Great job. I I just got a few more questions and I'll let you go back to work here. You know, one thing I wanted to ask you earlier that I didn't ask you about, you really pioneered loyalty programs. What do leaders really miss out on when they think about loyalty programs? Yeah, I think that they are focused on first, kind of the economics and second, kind of the very basic tenets of what people have done in the past. So, you know, it's either money or they get money back or, and they're sort of trying to use the reward system as a way to make people come back and buy or, you know, do whatever they want them to do.

57:39And I think that the thing that is singly most important as you're thinking about a loyalty program is your service experience overall. You can put the best loyalty program ever on top of a shitty service experience, and it's not going to do anything. And so loyalty is not a solve for, you know, like bad customer retention. Bad service and bad experience is the problem. And so, you know, my feeling is I think people look at this as like a way to solve for other problems in the business, and that just doesn't work. Whereas, you know, I think one of the things we really did at Sephora is we had a good experience and people loved, you know, the experience.

58:20And we really spent, I mean, the company spent eight years building that experience with so much love and attention and really refining it. And so by the time we launched the loyalty program, we had a couple of thoughts in mind. One is make sure this doesn't hurt the current experience. Don't slow people down. Don't make it like, you know, sort of a hassle. and make it, the second is make it connected to what people love about the business. And so we used, as I mentioned before, we used beauty products as the currency and it gave people a chance to sample new things and always have new products to try out.

58:54And so, you know, I think you need to think about the customer experience and then sort of figure out the economics and back into it. But you need to build this on top of a solid experience. And when people jump to loyalty as the solution, I would say it is not, it is an add-on.

59:09David Novak:You know, that's great advice. And, you know, speaking of leadership, what's a lesson that you've learned in your career that makes you a better leader at home? It's funny because I think a lot about how my role as a mother has made me a better leader at work. You know, I think the patience that's required and sort of the ability to listen really well and be able to like play back what you're hearing. I find that that works well at work. I guess what I would say is, you know, at work, you're really, you're required by your team to be able to explain why you're doing something. If you don't do that, people just don't get on board and they don't execute well.

59:55If they're just sort of given a direction without the context, it's really useless and they're going to fail. And so really being able to like tell the whole story and give the context is essential. And I think that has made me a better mother, too, by sort of not just saying yes or no, but explaining the why behind my reason, I think, has helped me become a better mother.

1:00:17David Novak:And, you know, I have to ask you this one. You know, what role has your husband, Brian, played in the person and the leader you've become? I literally would be nowhere without him. I mean, you cannot have a family. Well, you can. People have figured it out. But it's very hard to have a family and be a leader in a company without having a partner who helps you through it all. So Brian is, you know, I would say both my partner in everything in life in terms of like picking up what I can't take on. He's also been incredibly supportive of my career and not at all, you know, I would say defensive or, you know, resentful.

1:00:56He very much is excited for me and the things that I do and wants me to have success, you know, in my life, the way he has had success in his life. And I would say also, he's just a great sounding board. You know, whenever I'm like really struggling with someone, I'm not someone who verbally processes a lot. I keep a lot in my head and I sort of think and write myself. But when I have a problem that I can't solve, he's the best person on earth to talk to. And he just makes things seem, you know, so much easier. So for all three of those reasons, he's been an enormous part of everything that I've done, including taking the risk to go start my own company, which definitely is something the spouse is very much a part of, too.

1:01:36David Novak:And, you know, it's early days right now with Daydream. You know, you're going into your second year. You've got a lot to do there. when you look at your life and who you are and where you want to go, what do you see as your unfinished business? Yeah, I mean, I think about it a lot. I mean, certainly building Daydream into a place that truly helps people find the things they love and helps the industry by creating more, you know, demand and just understanding overall is really a big goal of mine. And if Daydream could become a household name, I mean, there are a few things that would make me more proud.

1:02:23But I would also say that I've always been someone who's very public-minded as well. I've always had volunteer efforts and other things that matter to me, making the world a better place, taking care of women and children, making sure the earth stays alive, and making sure democracy remains. And so I see myself over time. And then, of course, the other thing that I'm so excited for is becoming a grandparent and enjoying. I've always loved kids. When I was little, I babysat. I loved having my own kids, although I've also loved being an empty nester. Don't get me wrong. Having that kind of freedom is incredible.

1:03:04But I think that, you know, was I look at my life in the future. It includes not only sort of building a business that helps people and is successful, but it also includes being a great grandmother and having impact on the world in a way that I can. I feel like I've already done some things that I'm very proud of there. And then giving back to others in the business world. So I love talking to entrepreneurs. it's probably my favorite thing to do. And the thing I think I will spend probably the most time doing when and if I ever retire. And, you know, helping other people who are going through the same experience.

1:03:47It's just really rewarding to be able to take all the lessons you've learned and pass them along. And it's really rewarding to hear from someone else. Thank you so much. That was so helpful. That's going to help me do X, Y, and Z. So those are the things that I think about when I think about, you know, my later years in life.

1:04:04David Novak:Great. And last question here. What's one piece of advice you'd give to anyone who wants to be a better leader? Either think about or ask the people you trust the most where you think you can improve the most. It's so hard for people to tell leaders what they're not doing well. No one tells us the truth. And so you have to find people that you trust who, you know, say to you, like, if there were one thing I would improve, what would it be? and, you know, really listen and take it to heart and then work on it. Well, Julie, I'll tell you what, you've obviously worked on being a good leader and you are a great leader.

1:04:43David Novak:You're a great thought leader and you've, you know, you're redefining what can really go happen in the retail space. And I want to congratulate you on your, all your success. And I hope Daydream becomes that household name you want it to be. Thank you. And thanks for your time and interest. I love your show. So it's a real honor to be here.

1:05:08David Novak:David, I don't know if you'll quite appreciate this the way that I did, but the fact that Julie Bornstein can say that her most prized possession, aside from her family and friends, is Sephora.com is one of the most iconic answers to a lightning round question ever on our show. Explain why. I mean, she built Sephora.com. Most women on the planet have shopped at Sephora.com. It's like the place to go when you need anything related to beauty or aesthetics. And she literally built that platform. It's crazy. It's like saying that, I don't know, Amazon.com is my most prized possession. But it actually is her thing.

1:05:49David Novak:Yeah, I love it. Yeah, I love it. I love how she still loves that company and still loves the roots of it and felt great about the fact that one of the persons that worked for her is now the CEO of the company. And I think that says a lot about her. I mean, she went down her path, but she's still roots for the people that she's left behind. I love it. David, as we do at the end of every episode, I want to debrief some of the main themes that stood out from your conversation with Julie. And the first one is this concept of just going for it. I mean, she tells a couple stories in the episode about how she envisioned the reality that she wanted, and then she just freaking went for it and made it happen.

1:06:30David Novak:The story about, you know, tracking down Howard Schultz and then begging Dan Nordstrom to let her work for him. What does it take to get that gumption and confidence to just go for what you want? I always think about what's the alternative going to be like? If you don't get what you want, how are you going to feel? If you don't, you know, go after something, you know, how are you going to feel about yourself? You know, and what do you have to lose? You know, if somebody says no, you can handle it. You just got to be tough. You got to be tough minded and you got to put yourself out there. And she did.

1:07:09David Novak:And she got the job at Starbucks and she got the job at Nordstrom. She's those are great examples of just being persistent and and believing in herself and going for what she wants. I thought it was great. It's sort of like this, Kula, you know, Nike, Nike's commercials, just do it. Okay. You know, if you don't go, Is it really that easy? Yeah. Yeah. No, it's not that easy. But if you, if you, if you wait for somebody else to give you something, very rarely does it happen. You better go for it. I love that she said she felt comfortable going up to Howard Schultz because, you know, she had read his book and studied up on what he was doing at Starbucks and, you know, had done some M &A work with a coffee company in her past.

1:07:56David Novak:So there is a level of preparedness that you have to go into those situations with. But I just love that attitude. What do you have to lose? Just freaking swing for the fences. But she wanted enough to get the context that would make her effective when she went for it. OK, so if you want something, get grounded in whatever it takes for you to get it and then go for it. If you go in there and you have no idea what you want and you're just going for it and you don't have any end benefit for whoever you're trying to convince that they should give you a shot. Well, good luck. But she she had enough perspective and enough.

1:08:38David Novak:hey, this is what's in it for you if you go with me, that she got those opportunities. And just going forward has to run hand in hand with substance. So you bring up a really good point there. But I still think you should just do it. I love it. Just do it. The first theme kind of runs into the second one that really stood out to me is the way that Julie shows up. And it's this idea of passion. I mean, she talks about being a young girl and selling barrettes and having this little business when she was younger, selling barrettes and then her obsession with fashion and Seventeen Magazine and the mall.

1:09:15David Novak:And then that just continued on through her career. And I think so many leaders today feel like, you know, their passion might be separate from their job. What do you have to say about finding your passion, David? I mean, can your passion really be the thing that you do? Well, it sure is wonderful when it happens. And everybody always tells you, you know, to do what you love. And the reason why you do what you love is because you're not really working. You know, you want to learn everything about it. You want to get better at it and you want to spend more time at it because you love it so much, you know.

1:09:53David Novak:And, you know, and passion also gives you enthusiasm that takes you through the good and bad times. Didn't you just love the way she lit up when she talked about, you know, her career? I mean, she got all excited and that excitement and creates a contagious enthusiasm that's important. But I think she's building something that she's passionate about. And it's making her life much more meaningful. And she's passionate about a lot of things. And I think that really, really helps her. I think to know what you're passionate about, first you have to know yourself really, really well. And that passion that Julie has has kind of acted like a filter for her in terms of where she's gone in her career.

1:10:39David Novak:I mean, she talks about when she was approached to be a CEO of several companies that she took some time to think about it. And then she ultimately said no because she knew that she wanted to start her own company. And, David, we talk about the idea of knowing yourself, of self-awareness on this show a lot. But what stood out to you about the way that Julie stays true to who she knows herself to be? You know, I think that what stood out to me was that she had opportunities to go be a CEO of a bigger company. But she just she knew that she wanted to be an entrepreneur. She's a born entrepreneur.

1:11:14David Novak:She wants to be in control of her thinking. She wants to benefit from her thinking. I mean, if she's going to come up with the idea, she'd like to, you know, maximize the financial return from that as well. I mean, you know, I think she gets a lot of emotional benefit and hopefully financial reward from this approach that is more right for what she wants to do. But I think it said a lot about her when I asked the question is, what's the one thing, one bit of advice you'd give to every leader? And she talked about the importance of getting great feedback, you know, really learning from people the truth about what you need to do to get better.

1:11:56David Novak:And because she wants to know herself and know how she's impacting others. And then, you know, that she knows will help drive her success. So, you know, I love the idea of knowing yourself and growing yourself. I think that's what she's all about. She knows herself. She knows she wants to grow business. She knows herself. She knows she wants to grow herself. And I think that's really powerful. That's so true, David. And I think that, you know, knowing yourself kind of feeds into both of the themes that we talked about. The first one, going for it. You know, you have to have that sense of confidence and self-awareness to go into those situations and know that you can get the thing that you really want out of that conversation or situation.

1:12:39David Novak:And then you also have to know yourself to figure out what you like. I mean, Julie said in the episode, one of the hardest things that young people have to do is they have to figure out what they want. And so I just love that this kind of main theme of like getting really clear, not only on who you are, but what you really want and what you're passionate about is an impactful and effective way to show up as a leader. Yeah, I would say the big, big takeaway for me is just know yourself, grow yourself. She's a great example of someone that's done that. Go for what you want and do it with passion.

1:13:12David Novak:and, you know, enjoy the hell out of life. I love it. Well, it certainly seems like Julie is enjoying the hell out of her career. And it was an excellent conversation, David. So thank you so much. And thank you to Julie for joining us for this show. And of course, thank you to our listeners for tuning in to another episode of How Leaders Lead. Come back next Thursday and we'll see you soon.

1:13:41you

From the publisher

The tech landscape is changing faster than ever, as we’re all trying to navigate big shifts in AI, consumer shopping habits, and more.

But it’s nothing new to Julie Bornstein. She’s been at the forefront of retail for decades, leading big brands like Nordstrom and Sephora through the ecommerce revolution.

And now, as the Founder and CEO of the AI-powered fashion search engine Daydream, she’s once again at the bleeding edge of technological change. 

But through every shift, the thing she keeps coming back to is this: people skills matter most.

In this conversation, Julie will help you stay on the front edge of technology – without sacrificing the people skills it takes to make them work.

This episode is for you if:

You’re thinking about making the shift from corporate to entrepreneurship 

You’re doing any work with customer-facing AI 

You want to understand the future of retail and ecommerce

You’re trying to design a strong loyalty program

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