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S2 E22 How Treating Your Brand Like a Magazine Will Help Your People Connect More to You and Your Offers

S2 E21 Everything You Need to Know Before Hiring a VA or OBM for Your Business with Alexandra Smith

S2 E20 The Truth About Building a Community of Over 100 Creatives

E29 Keeping a Creative Outlet + Pursuing a Full-time Career with Rolanda Evelyn 👗🌀

You probably heard several stories about creatives leaving their day job to pursue their side hustles. But some creatives manage to wonderfully balance their full-time work and find time to fuel a creative outlet.

In this episode of The Pollen Podcast, Diana talks to Rolanda Evelyn, the senior product development manager at Rent The Runway and editor-in-chief of her blog, leave a little sparkle. She talks about pursuing your desired career while having a creative side hustle that brings joy. It takes more than talent; critical elements of Rolanda's journey were knowledge of what she wanted and the grit to keep going.

Listen to this episode to gain insights on how to have a creative outlet that fuels your wants and needs!

Create your own creative entrepreneurship story of clarity, professional confidence, and profit. Join Diana’s 90-day group course Camp Clarity and learn everything you wish you already knew, like how to land dream clients, harness the power of social media, and make the money you deserve. Learn more here.

🔥Here are three reasons why you should listen to this episode:

  1. Find out the value of having a creative outlet that you can balance with your job.

  2. Understand the different challenges and advantages of growing up in an immigrant household.

  3. Discover what paths can be created for you when you dive into new things headfirst.


🎧Episode Highlights

[07:16] Getting to Know Rolanda

  • Rolanda is a New York native.

  • She grew up in an immigrant household and was among the first-generation Americans in her family.

  • She is a full-time senior product marketing manager at Rent The Runway, a service and subscription-based fashion company.

  • Rolanda is also the editor-in-chief of her blog and creative outlet, leave a little sparkle.

[10:32] A Focus on Excellence

  • Rolanda’s parents believed education was an equalizer and they raised her with a high bar for academic excellence.

  • She spent her childhood studying, using her weekends for enrichment classes, and taking extra homework.

  • Her parents did everything they could to ensure their children excelled in school.

  • Focusing on excellence taught Rolanda to have grit in everything she does, including her creative outlets.

[15:05] Rolanda’s Childhood Creativity Pockets

  • Rolanda grew up with different creativity pockets that gave her a creative outlet.

  • Her parents enrolled her in different extracurricular activities like ballet and karate classes.

  • However, Rolanda’s main interest was fashion.

  • She remembers dressing up every Sunday for church with her grandmother, pairing different handbags and shoes together.

  • Every week, her mother would take a photo of her Sunday outfit and add it to a photo album.

[18:19] The Birth of leave a little sparkle

  • Rolanda grew up knowing what she wanted to do: communication and fashion.

  • She pursued studying at the University of Pennsylvania because it had a communication major and a fashion community.

  • Rolanda did her best to be involved in the University of Pennsylvania's fashion community and retail club.

  • The blog, leave a little sparkle, was born out of her desire to continue creative pursuits in fashion.

[23:36] Rolanda: “The hardest part I learned once [I] started [was], I don't have to wait for this thing to be perfect in order to launch it. If you wait for it to be perfect, [you’re] gonna be waiting forever.” - Click Here To Tweet This

[24:17] Starting a Career in Product Marketing

  • Rolanda recounts hearing about the product marketing industry and being captivated by the work and people inside.

  • She decided to follow this path and pursue the blog on the side. This way, she gets to have both worlds at the same time.

[26:38] Rolanda: “Sometimes the plan that you have set out for yourself, as I just described, doesn't always go the way that you thought it would. But it's kind of the path that you should be leaning towards.” - Click Here To Tweet This
  • Her product marketing job sits between brand marketing and product development.

  • Rolanda enjoys her job in marketing because it's an intersection of the left and right brain — creativity and strategy.

[30:47] Building A Fashion Network

  • Rolanda looks for people on the San Francisco geotag and "fashion blogger" tag to grow her network.

  • She would follow and DM them. Sometimes, she also finds other bloggers from her Following’s posts and stories.

  • Rolanda would also ask her colleagues to connect her to fashion groups and photographers in their communities.

  • The creative fashion scene in San Francisco is small. Once you've been in it, you most likely know everyone.

[33:27] Creating Her Identity In The Blog

  • Rolanda wants her blog to be a creative outlet where she can share her day-to-day experience as a Black woman working in the tech industry.

  • Rolanda learned that her blog, like life, cannot be all sparkle and rainbows.

  • She wants the blog to “sparkle” but also show realness.

  • Her blog also acts as her place to escape.

[40:27] Moving To New York and Pursuing Fashion

  • After finishing her program, Rolanda moved to New York to become YouTube’s product marketing lead for fashion and beauty.

  • Quitting Google without having another thing to land on was a significant point in her journey.

  • Rolanda’s job with Google gave her financial independence and allowed her to pay off her student loans. However, she wanted to transfer to the fashion industry.

[43:54] Rolanda: “What are you waiting for? Just go do it. What could possibly go wrong? Try it. If you hate it, you can undo it. What have you got to lose?” - Click Here To Tweet This

[45:27] Signing Up with Rent The Runway

  • Rolanda was supposed to start Rent The Runway in March 2020 but had to delay it to July 2020.

  • While waiting to start her new work, Rolanda got numerous offers from other tech companies.

  • However, she was set on Rent The Runway because it was what she wanted.

  • Eventually, she learned to ignore calls from the other companies.

[47:22] Rolanda: “What are you waiting for? Just go do it. What could possibly go wrong? Try it. If you hate it, you can undo it. What have you got to lose?” ce. I was like, ‘I'm going to remove the things that make it hard to choose my choice until I can no longer choose my choice anymore.’” - Click Here To Tweet This

[49:56] Continuing leave a little sparkle

  • Six years after starting her blog, Rolanda still maintains leave a little sparkle as a creative outlet.

  • Rolanda remains intentional with what she posts.

  • She does not create content to appease the algorithm. She creates content that brings her joy.

  • The blog gives her this creative freedom because it is not her source of income.

  • You have to have something that makes you feel creative and protect it. For Rolanda, this is her blog.

[53:28] ⚡️ Rapid-Fire Questions with Rolanda

  • Rolanda is a Pisces. For Rolanda, creativity means reimagining and romanticizing anything — people, movement, nature, and other things.

  • Rolanda’s entrepreneur crush is Crystal Beck, a former Googler turned full-time blogger. She finds her the perfect example of being creative on your terms and doing what brings you joy.

  • Rolanda’s current read is Happier Hour by Cassie Holmes. It’s a book about living a happier life, using your time for things you care about, and being present.

  • Rolanda is currently listening to Angela Duckworth, the author of Grit and developer of the concept of grit.

  • If Rolanda didn’t have to think about money, time, and resources, she would do a talk show.

About Rolanda

Rolanda Evelyn is the Senior Manager of Product Marketing at Rent The Runway. Rolanda describes herself as a strategic storyteller passionate about the intersection of fashion, retail, and tech. She is also a blogger and content creator for her blog, leave a little sparkle.

Learn more about Rolanda through her blog, leave a little sparkle. You can also follow her on LinkedIn and Instagram.

Enjoyed this Podcast on Balancing a Full-time Career and a Creative Outlet?

Are you torn between keeping your day job and pursuing your side hustle? Here's a confidence booster: you don't have to give up either of them. Having a full-time career while maintaining a creative outlet is a balancing act, but it's worth it!

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Rolanda: When I think about now, you think about what were the things that I used to do in my free time as a kid that are basically windows into the things that I was naturally curious about. So yes, I loved fashion from a very young age. My mom would take photos of me; this is literally — it's like self prophecy — my mom would take photos of me in a different outfit every week. I would go to church with my grandmother and there's a photo album of every Sunday outfit.

Diana Davis: Welcome to Pollen, the podcast for creative entrepreneurs. I'm your host, Diana Davis, multi passionate creative, business coach, Gemini, manifesting generator, macha drinker, and travel junkie. I'm also the founder of Diana Davis Creative, where I went from a six figure photography business to coaching creative entrepreneurs like you. If you want to have a career and a life you love, you're in the right place.

On this show, I'll be coaching on all things creative entrepreneurship, and you'll hear stories from fellow creative entrepreneurs that will show you it is possible to do life the way you want to. They'll share the nitty gritty of their journeys, like the real shit, and how they are doing it differently. I'm stoked to have you along on this journey. Let's go.

Hi, y'all. It's another day, another week, another podcast guest, my friend Rolanda is incredible. And I can't wait for you to hear her story.

She is one of the few entrepreneurs that we featured that actually has a full time job, as well as a little side hustle. And she's actually stoked to be in her full time job and is not looking to get out of it. So if that is you, you're definitely going to find a lot of inspiration in this episode. She's actually a senior manager of product marketing at Rent the Runway. But she's also headed up really amazing new ventures for YouTube and Google.

She's a badass. She also has a fashion blog, and she's just a kick. So definitely check out this episode if you are someone who's in a full time job and maybe even not wanting to leave it. But check out this episode either way, it's going to be epic. The other thing I want to remind you about is we started Camp Clarity yesterday. Round seven. And even though we've had our kickoff call, it is not too late to join.

If you want to jump in, DM me over on Instagram, that you are ready to jump into building the foundations for your creative business. Let me know, it's an amazing, amazing group already. And there's room for you at the table. All right, enjoy this episode.

Hello, Pollen. We're so excited to have you. We have a really special guest today, my friend Rolanda. And I feel like we've been playing kind of like the phone tag game for a while to try to get this on the books.

Now, we're in the same city but in different boroughs right now, sitting in our offices. And we're gonna chat. So Ro, how's it going? What's up? Glad to have you here.

Rolanda: So pumped to be here. And I'm so pumped to talk to you. I was just like– I feel like we have really deep, authentic conversations more generally. Like you're always the person that I'm like, “Well, my friend Diana.” So I'm like, you want to record it and have other people listen to us. Like, I'm so gay.

Diana: This is basically like us at brunch, on a podcast.

Rolanda: Yeah, our extended brunches that always take an hour or two–

Diana: Five hours.

Rolanda: Then we moved to a park and then we moved to–

Diana: So good. So a quick backstory of– I think it's so expansive how people meet each other. Rolanda and I literally met in a book club before the pandemic, because we were meeting in person and the book club kind of had to end because of the pandemic. And it didn't really end, it just fizzled out. We were doing it on Zoom for a while. But I just knew she's just going to be my friend.

We're going to be friends. And all of just like the quirkiness and outgoingness. And also all of your little stickies in your books. She's known for showing up with 50,000 stickies and notes and all the books, even if it's like Little Women or some classic novel. So, I love that, that we met that way and then we actually started–

Rolanda: Well, do you remember Diana? It was– so we had our first book club, and we shared the elevator together. I'd never met you.

Diana: Yes.

Rolanda: You said my name is Diana, like Princess Diana, so you won't forget. And then we were on email because we were coordinating the next book club meet up. And in your email signature, you had– because this is what I feel like our book club was one of the places where you don't lead with like what you do for work. We were nicely there. It's so refreshing.

Diana: Yeah.

Rolanda: I did it. I like the majority of the people in the room who I'd never met. I didn't know what they do for work. And so when you sent the email about when you were available, in your email signature, you had your website, and at the time as being a photographer. And I was someone– I had just moved back to New York, and was looking for people to collaborate with.

I was like, “Oh, my God, I spent like three hours with this girl, and she's a creative, and she's a photographer, and I had no idea.” We could probably find that email. And that's how we like–

Diana: Yeah.

Rolanda: –ventured off. And I was like, “Oh, like Diana is my person.” But I would have never known that because we didn't talk about like what we do for work at all.

Diana: Totally. I don't think I remembered that it was through that email signature. I just know–

Rolanda: That's why.

Diana: Yeah, I love it. And so, you're my people. So we did some shoots together, which we'll talk about why you do shoots and all the things. And then we went– and we're friends through some crises of our own and our personal life. And then we're friends through some pandemic crises. And then we've now– every time I come to New York, we try to have brunch or something.

We're always venting about books over voice memos, and all sorts of stuff. So I want to tell your story, because not a lot of people do we have on this podcast that actually have a side hustle. And then just a really fucking successful career. You're such an expander in like, as a career woman. It's so badass. And also, you're not wanting to leave your career, which is very rare for people to hear.

I think there's a lot of entrepreneurs out there, or side hustlers that feel the societal pressure of quitting their day job. And that's not always the case. Like you can have a creative side hustle that fuels your wants and needs on the side. So let's just get started with who you are as a person. And what you do now? Who are we today?

Rolanda: Where are we today? Well, I would say the first question of who I am as a person, I would have to go back to one being a New York City native, because that is tried and true to who, how I grew up, where I was raised. I feel like New York is a very big part of me. I think I would also be remiss if I didn't mention that I– my family is from the Caribbean, they were born in Guyana.

I grew up in an immigrant household. My brother and I, and our cousins are the first generation to be born in the states, to be born in America, to go through the education system here, to graduate college. All of those things are milestones in my family. And so, so much of how I think I was raised and how I see the world is coming from that perspective.

The mentality and the values that are handed down to you in an immigrant household, I think are very different than those, I would say at large, like in America more generally. And then like, even if you move outside of communities of color. So, we're– this is my voice, so people can't see what I look like. But being a black woman and being a woman who was born to immigrant parents, who come from the Caribbean, that is such a big part of my identity.

I think that permeates through a lot of the ways that I show up, whether that be in a relationship, whether that be in friendships, whether that be at work. So that's like I would say, at the crux of my identity and who I am.

To the second part of your question as what I do. So I– for my full time job, let's say, I'm a product marketing manager at Rent the Runway. For those who don't know what Rent the Runway is, Rent the Runway is a service where you can rent clothing.

Oftentimes, you can rent items for special occasions like a wedding, dresses that you'll never wear again, or you could sign up for a subscription and get clothes sent to you on a monthly basis to rent for anything from coats, and jackets, and bags to jeans and tops. Which I know, Diana, you've tried to. So yeah, I spent– I've been at Rent the Runway for a little over two years.

Diana: How freaking flies.

Rolanda: I know because you met me when– you met me before all of that.

Diana: Yeah.

Rolanda: I've been there now for over two years.

Diana: Wild. And we'll talk about this but I think it's cool like you were such a fan of Rent the Runway before you were there. It's not like you're like “Okay, I'll accept this job.” You've been like a Rent the Runway queen for years and years and years of like you barely own clothes, you just rent them, which is so cool because you have so many different ways to express yourself.

You're such like a colorful, expressive person that really jives for you, which is always fun to follow along with. Something I want to go back to, because I think it's important, are the first guest of the Pollen podcast ever was Wini Lao, who grew up in New York City as well. And she is born to Chinese immigrants. And she talked about this a lot as well.

You mentioned very specific things or themes from being in an immigrant household and being the product of that in the first generation American. Can you give us a couple of those, what those themes are and how that plays out?

Rolanda: Yeah. So for me– oh, my God, my parents are gonna be like, “What is she saying?” I'm just kidding. For my brother and I– like, the bar was pretty high. The bar for excellence was very high. And there wasn't really an alternative other than that path to excellence. And when I say excellence, I would say in our house, that meant educational achievements.

For my parents, so much of what they wanted for my brother, and I was to prioritize school, go to college, go to a great college, because that was really important to them. And that those weren't opportunities that they had. And so for us, that meant my childhood, my weekends were spent in enrichment classes. I actually went to a New York City program called Prep for Prep that specifically takes students of color from the New York City public school system.

You go through a 14-month process, which means you go to school in the summer after fifth grade, you go to school after school on Wednesdays and on Saturdays in sixth grade, and then you go to school, again in the summer, right before seventh grade before you transfer to New York City Independent School. The reason you have that 14-month process is to basically catch you up between the difference in the education gap in the public school system and the independent school system.

It's a very competitive program. It's a program that my parents prioritized for us. I was accepted and then transferred to my prep school. And then from then, from 7th through 12th grade, I stayed at that prep school. And then for undergraduate, I went to the University of Pennsylvania. So I say that to say everyone's path to success doesn't need to look like that. In my household, though, in the way that we were raised, that was the number one goal.

Anything that could get in the way of studying for a test, or taking an AP exam, or doing really well on an SAT, or any of those, I would say very traditional quotes, or standardized quote, measures of success, those were the things that were priority. And my parents did everything in their power to make sure that those were the only things we had to be concerned about or be worried about. Because in their eyes, education was the equalizer.

That would be the way that this generation could do better than them. So hard work, studying, using your weekends to get ahead in class, like having extra homework that your parents assigned you outside of what your school assigned you, that was how I spent my childhood. And of course, you don't know that you would see other kids outside, like, “Why do they get to play for one more hour?” Or whatever it is.

You follow the rules that your parents set, but looking back, you're like, “Oh my gosh, I had such a different perspective.” Because that's just what was taught to me as what was the most important and I will say, like, “I think this idea of diligence, and I'm not gonna lie, it was a lot, it was really hard work.”

But I obviously achieved it and did well. It definitely teaches you grit, and how far you can go even if you think that you may not be able to– I obviously caveat that with there's a flip side of that, where mental health, well being, happiness, all of those things are also important.

I would say as an adult, those are the themes that I had to teach myself. Those are the things that weren't, that are not talked about in immigrant household, especially in Caribbean households. Talking about therapy and mental health, those are not things that are common. And so in my adult life, though, that was the side of the spectrum that I had to learn on my own.

Diana: Thank you for sharing that. Was there a piece of– just really quick before we dig into like the full story. Was there a piece of fun that little Rolanda expressed herself through? What was– were there moments of creativity we can spoil that you're in fashion, we know Rent the Runway, but you're also in fashion for yourself and your side hustle? Like, what– do you look back and go like, “Oh, my God, of course.”?

Rolanda: Yeah. Oh, my god. It's so funny because I always think about– when I think about now, you think about what were the things that I used to do in my free time as a kid that are basically windows into the things that I was naturally curious about? So yes, I loved fashion. From a very young age, my mom would take photos of me. This is literally– it's like self prophecy. My mom would take photos of me in a different outfit every week.

I would go to church with my grandmother and there's a photo album of every Sunday outfit that I used to wear with my church dress, my church handbag, and shoes that were paired together. And I loved that.

But I would say so from a young age, my mom– I was enrolled in ballet classes. And I would say like my parents were good about– they would expose us to different extracurricular activities. And if you liked them, or if you didn't like them, that was up to you.

But it was like, “Are you copping out of this? Because you don't like it or because you don't want to do it?” Like, “Do you have enough information to make that decision?” So I tried karate, didn't like that. But I– so I ended up doing ballet classes, I loved dance. I love performing. I loved being on stage. And dance was something that took me all the way through high school. I ended up being the co-captain of my dance company in high school.

Also led our student choreography showcase. So like choreographed pieces, with my peers at the time, and it was so much fun. So dance was such a big outlet for me. And continues to be, it's actually something that I would love to do more of now. So there are definitely creativity pockets.

Diana: Yeah.

Rolanda: They were diligent, like we're gonna sign up for this activity. We don't quit. We show up to the rehearsals every Saturday like–

Diana: Outfit every Sunday.

Rolanda: Exactly.

Diana: Yeah, very by the books. Okay, so what was your degree in?

Rolanda: I studied communications as my major. And then my minor was a double minor in Hispanic studies and consumer psychology.

Diana: Interesting. Okay. So then–

Rolanda: Which was the whole thing because I didn't want to be pre-med, which, in an immigrant household, you have three careers to choose from.

Diana: Okay.

Rolanda: Being a communications major and wanting to work in marketing is not one of them.

Diana: What are the three? Pre-med–

Rolanda: You be a doctor, you can be a lawyer, and there's some like business, like–

Diana: Right. This is literally one of my tag lines of like, you don't have to be a doctor, or lawyer, in finance to make money.

Rolanda: Exactly.

Diana: So true. Oh, my God. Okay. So we got these majors and minors. When did the blogging– tell us about the birth of your blog? Where did that come from?

Rolanda: Yeah. So I've always been the person, I would say, that I know what I want. I know what other people want me to do. But I also know what I want. And I'm not very good at doing– I'm not very good at taking instructions from other people. I like to lead. I like to lead. And you can give me advice, but I'm probably going to pay attention to what I think is best.

The reason I even landed at Penn was because they had a communications program, which is so random, because people were like, “What is communications?” But I had– I went to a communications conference, my senior year of high school, long story short, and the editor in chief of Seventeen magazine, was the keynote speaker.

For all of the things that she was talking about, I remember thinking, “Oh my God, these are all of the things I love. I can– this could be my job, like I could work in fashion and I can write.”Iit was such a lock to be like, “Oh, I don't have to be one of those three things.” There were like, “All these other things I could be a part of.” So from that conference is what I decided I was gonna major in communications.

Long story short, there are not that many colleges that offer communications as a program. They'll have English or have journalism because they are going into like news marketing.

Yes, but communications as a field, especially when you're looking at undergraduate degrees is very limited. So I felt very fortunate to land at Penn that has a very well established communications department. When I got to Penn, the other thing that I was very much looking for was a college campus that had a fashion community. So that often meant that you kind of have to be in a city, because you needed to have some sort of relationship with the boutiques and the scene there.

There's also Philadelphia Fashion Week, like not all cities have that.

Diana: Right.

Rolanda: I was also kind of set on leaving New York having been here like, “Oh, I chose Philadelphia, which is two hours away.” But I wanted to–

Diana: Very different though.

Rolanda: I wanted to move to a new city. So when I got to Penn, I was very much on the hunt for how can I get as involved in fashion as I could. We had a fashion magazine that was very well known.

I was immediately involved in that; I would work on the shoots, I would go pull samples, I would write for the website. I literally was like, “I will do anything,” like I just want to be able to be a part of this. Because this wasn't something I was able to have in high school, we didn't have a fashion magazine or anything like that.

We also had– because of our business school, we also had a retail club, which meant we basically had the executives from the biggest retailers in the world coming to give keynote speeches to our undergraduate community. And it was so interesting to just hear from different thought leaders, different marketers, etc. About the changing landscape of retail at the time. I know that sounds probably like such a snooze fest and most people, but I was eating it up. I was so excited about it.

Diana: That's how you know. It’s a snooze fest to people and you’re interested. It's like, “I got some time.”

Rolanda: This is my thing.

Diana: Yeah.

Rolanda: I think I– having been able to be a part of all of those things in college, as I was graduating, and I at the time knew that I was going to Google and I was moving to San Francisco, I was like, “I don't want to lose this thing that I found that I loved, all of this creative outlet.” And I remember, this sounds so crazy. But I remember freshman year, where someone had said to me, “Well, you're the creative one.” Like, of a friend group.

I had never thought of myself as a creative, ever. Because I was like, I can't draw, I can't paint. Creative meant such a very specific word, like definition in my head at the time. And so I had never thought of myself as a creative. And by the end of college, I was like, “Oh! Creative. That's what I do.” And so effectively, the blog was born out of my desire to try to hold on to creative pursuits in some fashion. I'll be so honest, I had no idea how I was going to launch a blog, I'd never done that before.

I didn't know how to use Photoshop, or InDesign, or any of those things. But I remember thinking if I keep saying it out loud, and I tell people that I'm going to start it, I'm going to have to start it because I've told people that that's what I'm going to do. So I kind of jumped in blindly I, you know, reached out to some people who had blogs that I was following, who I liked, and asked for advice or things that they wish they knew when they started.

Diana: Yeah.

Rolanda: People are at work, amazing and gave me everything down to like what to host your blog on. I didn't even know that you had to like host blogs anyway. And you kind of just do it. And then you figure it out. The hardest part I actually learned was starting. So once you start then like, “I don't have to like wait for this thing to be perfect.” In order to launch it. If you wait for it to be perfect, we're gonna be waiting forever.

I kind of just– I did a little like interview circuit and was like– I, one of the pieces of advice was to have at least three like blog posts already shot so that you could have a steady stream of content. And I went from there.

Diana: I love it. And so you got a job at Google. You moved to San Francisco. You're working in YouTube. Yeah?

Rolanda: Yep.

Diana: In Google. What was your job title there? Were you excited about it? Are you still–

Rolanda: Yes. So I was a product marketing manager. I've been a product marketing manager this entire time, which is like kind of crazy. Actually, I take that back. Not kind of crazy. I say not kind of crazy because I spent my entire four years at Penn, trying to figure out what it is that I wanted to do. So at first I thought, ” I want to be an editor in chief. I want to work at a magazine.”

Spent some time talking to people, shadowing people, learned that that was probably not the best place for me especially you have to remember this was 2012, 2013, the birth of magazines are kind of starting to have a fall out, online is really taking off the future of like– the editor her in chief title in that way was very much changing. And I think there's been a couple of articles written about how a bunch of those editor chiefs now work in tech, which is really interesting.

I thought I wanted to be a buyer. I was like, “Oh, great, I get to go to shows, I'll be able to pick inventory for a large department store.” I shadowed a buyer who went to Penn, spent the whole day with her and decided, “Nope, don't want to be a buyer. Don't want to be in front of an Excel spreadsheet all day. That is not what I want.” And I very random, not randomly, but I interned at Google in PR because I couldn't intern in the buying internship until the following summer.

To me, Google was just a, “I'll do this for one summer.” But then I really go get to do the buying thing, that's like really what I want to save my junior summer for. And I went that summer, and I loved it. And then I learned that I didn't want to be a buyer. And then so I actually when I went back the second summer, I had my internship in product marketing. And that's when I was like, “Oh, that's it. This is exactly the thing I want to do.”

Even though it wasn't in the industry that I thought I wanted to be in, the work and the people were so captivating to me. I was like, “That's what you follow first.” And I can obviously always come back to New York I can I have so many chapters in my career, for it to be in fashion. And I then decided to start the fashion blog. So I was like, “I get to have both worlds at this time.” And so that's how I ended up not living in New York, not working in fashion, moving to San Francisco, and working at a tech company.

Diana: Yeah.

Rolanda: Sometimes the plan that you have set out for yourself, as I just described, doesn't always go the way that you thought it would, but it's kind of the path that you should be, you should be leaning towards.

Diana: Absolutely. Universe always has your back.

Rolanda: Exactly.

Diana: Yeah, I love it. So can you, just in a couple of sentences, because I'm sure a lot of us don't actually know like what is a product marketing manager? What is product marketing?

Rolanda: Yes. So product marketing definitely takes different shapes at different companies. But I would say, more generally, a product marketer sits in between what I would say is the traditional one folks hair marketing brand, like a brand marketing team.

The folks who are in charge of leading all of the marketing campaigns, the things that you see on TV, the ad that you see online, the billboards that you see outside, the emails that you read, the things that are posted on the company's social handle that’s what the traditional brand marketing team does, I would say more generally. And then on the left side would be what the product team does.

A product team, normally at a tech company consists of product managers who decide what products you're gonna want, what features we're going to launch, what are we going to roll out next to evolve whatever app you're working on.

Product team normally includes a product manager, a UX designer, or UX writer. They literally design what websites look like, what the words on your app says, how notifications pop up. Everything that we interact with online, is designed and built by a specific team.

A product marketer, I would say, sits in between those teams, and that you help shape what the journey and what the user experience looks like in the app or on the website. And then you also then work with the brand marketing team to send the comms and the communications that you then alert all of the users of how to use this feature, or what's new, or what's changed.

For me, I really enjoy it because it kind of like the intersection of like left brain, right brain. I get to be creative, I get to be strategic. And it's the perfect, you should have that for me. So that's like–

Diana: Love it. So we're in San Francisco are working at Google slash YouTube within Google, and we are starting our blog. How's the blog going? What what was that like? You start doing shoots in collaborations with other photographers, you're putting up your posts. Are you starting to work with brands? What were some kind of the evolutions and also some surprising things that happened?

Rolanda: Yeah. So when I first started my blog, I started it the summer before I moved to San Francisco. So that meant I had my brother, and my brother was my photographer,

Diana: Love it.

Rolanda: Shout out to my brother. And it also meant that I had some of the photographers that I knew from Penn who were interning in New York that summer. So in a way I was able to take advantage of the network that I had here, which was really great, especially in the beginning. And then I moved to San Francisco.

I effectively knew no one. I didn't know photographers and no other bloggers. I was kind of starting from zero again. So I remember it being really hard in the beginning to meet other creatives. I know that sounds kind of strange now, but especially I would say, in San Francisco, where the scene is very much dominated by tech.

Diana: I feel like a lot of people have, even though it might sound strange, I feel like a lot of people can relate. Just like, how do you build a community, let alone a community that is like-minded, you know? And was really quick, was Instagram really, really a thing yet? Like, you're really going for it on Instagram as well. Like, were you meeting people through there? How did you meet these people?

Rolanda: Yeah, so effectively, you just– what I did was you stalk people based on the geotag in San Francisco, and fashion blogger tag. And then I would start following them because I hadn't started falling like that, like San Francisco bloggers. I would follow them, and then I would like DM some of them or you would see events that they would be going to, and then you would find someone else from their story, who is more similar, more of an overlap. So then you would DM them.

It was very scrappy. And I remember– so like, that's how I started following fashion bloggers on Instagram. And then at work I had– like it was a, my marketing program there was like, I don't know, maybe like 30 of us new grads.

Two of them went to Berkeley, like undergrad. So I asked them to, introduce me to I was like, “Oh my gosh, you must have had a fashion group on campus. Can you connect me with any like, like any photographer or the fashion group that you may have known?”

I was really– I was trying really hard to create a creative community there. And eventually, it happened. So eventually, a photographer, that I DMed and on Instagram was like, “Sure, let's meet up. Let's have a shoot.”

I remember I was so nervous because it was the first time I had a photo shoot with a stranger, like where the photographer wasn't my brother, or my friend from my Penn.

Diana: Yeah.

Rolanda: I was like, “Okay. I guess I'm just gonna show up and hope for the best.” And it was amazing. She was amazing. It was such a beautiful show. It was actually on the Golden Gate Bridge.

Beautiful, clear day, like, obviously– and we got there super early, so that it would– everyone would always be so surprised by like, “Yeah, I have to go to bed at like 10pm on Friday night, because my shoot on Saturday is like at 7am.” Like, that's the only way that this works.

Eventually, as you start meeting people, and they start introducing you to people, you go to events, and you meet other people than you like– and to be honest, the creative scene, the creative fashion scene in San Francisco was very small. So once you made it, then you know the entire group.

Diana: Totally. And what was– what were you blogging about? Like we're doing your outfits basically is like Sunday church style, but in blog form?

Rolanda: Yeah.

Diana: Were there stories coming along with this? Were you working with brands? Were you tagging them? What really was the why behind it?

Rolanda: I remember having a huge, internal conversation about this, because I remember thinking, I don't want to tell people what to wear. Because they think that I can tell you what I wear. But I'm not going to tell you that that's what you should wear because they think fashion is so personal.

Diana: I love that.

I remember thinking, “I don't always want to tell you to buy something because that feels so like consumerist. I care a lot about sustainability.”

I also think that if you invest in a couple of pieces, and then you hold on to them that are timeless, I think that's also very much a part of my identity, too. So it's like, “Okay, I'm not going to tell you to shop these things.” So then what do I talk about? I don't know what to say. And I remember kind of searching, internally searching about this. And I was like, “Oh, I'm just gonna talk about my day to day experiences.”

I don't have to create this brand new, content pillar, or come up with, my experience as a black woman who's from New York, who moved to San Francisco, working in tech is fine enough.

Diana: Yes.

Rolanda: People who want to resonate will resonate with that or interested in hearing those experiences will follow along, and those who aren't, “Whoa.” And that's totally fine with me, but I was I'm not gonna I perform here, I'm not going to do something that doesn't feel genuine to me.

The thing that’s most genuine to me is what I'm– my lived experience.

Diana: It’s been you.

Rolanda: Yeah, I would get into it on my blog. I was living in San Francisco, would not recommend that as a place to live as a person of color. I was very clear about that on my blog. And obviously, I'm speaking in the first person I'm speaking and the experience that I've had.

I remember even when I was posting articles similar to that, I'd be like, “Is this too much?” I wanted this to be a place of– my blog is called leave a little sparkle. I wanted this to be sparkle. I wanted this to be, like my place of escape. And I remember having a reckoning about like, “Does this muddy that if I bring all of these negative sentiments here?” And then I was like, “No, this is an accurate portrayal of my experience in San Francisco.”

You get the sparkle, but you also get the realness too. So both of these things can exist together both can be–

Diana: Yeah.

Rolanda: That was a big learning for me too, because I felt I had to pretend that everything is sparkle and rainbows when to be obviously frank, I think we all know now, that's not true. And I was just like, “Okay, that's like what we're gonna lead with. And if people don't want to read that, they don't have to, because they can just close.”

Diana: Yeah.

Rolanda: That was very, like, liberating for me.

Diana: Yeah, that's what makes you, you. It's like, there's a million fashion bloggers out there. We could be looking at outfits on people. Who cares, right?

Rolanda: Yeah.

Diana: But like, leading with your authentic self, you know I'm about that.

Rolanda: I know you are.

Diana: I love that. Okay, so we get transferred to New York,

Rolanda: We worked really hard to get to New York.

Diana: We were needing to get out of Stanford.

Rolanda: We needed to get out– I was in San Francisco for two and a half years, I would say the first year and a half was the best part. It was a new city I did all of– I traveled everywhere, I did every single West Coast California thing that any California person will tell you. I did it. And then you– after that wears off and you stop, you have checked things off the box.

I would say that in combination with the class that I started with the majority of folks, you have the opportunity to to rotate, so you could move to London, you could move to New York, you can move to LA. The majority of people in my class chose to move, which I think is also telling–

Diana: Is a lot.

Rolanda: That's a lot. Though, I was falling of the role that I wanted. And that role was based in San Francisco.

I stayed in San Francisco for the second rotation. And so when the majority of your friends move, you see the city in a completely different perspective, from a completely different perspective. And I just remember feeling like “God, this is not a place that I want to be in. This is not a safe space. This is not a diverse space. This is very– this is so anti the things that I stand for– in my being.” So effectively after my pro– the program was two years.

I did two teams in two years. I was like, “Okay, I have to get out now.” And the universe works in strange ways, as you said. And effectively after I graduated the program, YouTube decided to start a fashion and beauty team based in New York. I know that sounds kind of crazy, because people were like, “YouTube didn't have a fashion beauty team.” We did it. They started a fashion and beauty team in New York. And I was like, “That's my ticket. It's either that's my ticket to New York, or that's it.”

I was like, “Well, then we go for it.” So I put together a pitch alongside some of my mentors at work, my manager at work, and pitched it to our CMO and said, “Here's where I think we have opportunity. Here is why I think I am the best person to lead product marketing for this. Here's a vision I have that we could execute on.”

Diana: Yeah.

Rolanda: I just need you to greenlight this for next year. And she did. Then moved to New York in January 2019 as a product marketing lead for our fashion and beauty, and public figures team in New York.

Diana: Cool. So what I know about you, I'm gonna fast forward a little bit. But we know you're super successful in this. You were kind of like had an inkling to just do something else. You and I had a conversation in a coffee shop, actually Clean Market on Upper East side.

We're just talking about like quitting the job like, “What is quitting the job with like?” Do you do fashion full time, could you do your blog full time is that even something you want, your passion project, making you money like that putting that pressure on it.

You are very wanted and desired in this role. There was a lot of resistance from your team to let you move on, which is very flattering. But how did we finally go from deciding to make the leap?

Rolanda: Diana, the road points back to you.

Diana: That wasn't where we're going with this .

Rolanda: I will say, saying that you want to quit Google, I know this is gonna sound so– whatever. Saying that you want to quit Google is not a thing that people get, understand. I will certainly tell you that my immigrant parents were like, “You want to do what? You want to quit the job that we did all of that work to get you to? And do what? What do you want to do? What could possibly be better than working at this company?” And I, like I said earlier, I know, I'm an intuitive person.

If I feel that there is something that I need to be paying attention to, I need to pay attention to it. And it'll catch up to me eventually. So you might as well pay attention to it. Yeah. You might as well pay attention to it sooner. And effectively, I would say, we had a really successful year at YouTube on the fashion and beauty team. And I kind of felt like, “Okay, I did it.” We did the thing that I set out to do. We kind of crushed it, like not gonna lie.

Diana: Of course you did.

Rolanda: But now, I live in New York, I live in the best city to work in fashion. Why am I staying at a company where fashion and beauty is this like little tiny, little thing? That's like a priority three project when I want to be working on the biggest priority project. And there's so many companies where the biggest priority project is fashion, right? So that's where I want to be.

Once I decided that. Once I was going to make this decision to go pursue this dream that I've been holding on to since college, right? I still haven't yet worked in the fashion industry. Let me go try now. I could try it out. And I could find that I actually eat it, which is also very valuable, I would say like, knowing what you don't like is almost like, twice as powerful as knowing what you do. I just tried out, I could hate it.

Great. Now I know that that's not a thing I actually want to pursue. I could go find and I could go back to Google, I could go to a different tech company. It’s not the end of the world. So I think getting over– sorry, and I should also add, because I was at Google, Google and– that gave me the financial independence because I was able to pay back the student loans that I had, after I graduated Penn. So that is not something to skip over. Having financial obligations is very real.

My financial obligations were to myself and paying back debt, which I was able to accomplish at that time. It was almost four years after I paid back my loans, I think a year after I graduated and–

Diana: Amazing.

Rolanda: The financial obligations were to myself, I don't support other family members. That is a very real thing for other people. And so that was not something that I had to consider when thinking about can I let go of this high paying job?

Diana: Yeah.

Rolanda: Given that, and given that I wanted to transfer to the fashion industry, it was also clear to me that I wouldn't be taking a pay cut, because let's just put the two things on the table. Fashion industry and the tech industry are apples and oranges. And then Diana, I read the book that you told me to read called You're a Badass.

Diana: Love it.

Rolanda: I don't know if you remember.

Diana: Yep.

Rolanda: That book was just like, what are you waiting for? Just go do it. What could possibly go wrong? There's like– try it. If you hate it, you can undo it. Like there's nothing like– what's what have you've got to lose? So I said–

Diana: Yeah. So you quit without another thing to land on.

Rolanda: I quit without another thing to land on. I had– I think I was interviewing about seven companies at the time. And they were across all– they were all in fashion. That was a requirement.

Diana: I remember we were in Madison Square Park in that little triangle–

Rolanda: In the little triangle. I had met you after, I think it was like a Tory Burch interview. And I was like listen, any seven of these, whichever, I would be the most grateful because then I get to understand, I get to answer the question. It'll be the learning opportunity that I need. And then we can take it from there. So yes, Rent the Runway was one of them. So I was like we'll see whichever of these seven work out. That's where I'll be.

Diana: Yeah. Now you've been there two years. And you got your answer, I guess. You love it. From when started recording, there's a lot of fun that's to be had.

Rolanda: Well, I would say the part that we can't leave out is when I decided to quit my job at Google, this was February 2020.

Diana: Ah, yes.

Rolanda: I was like, “Oh, I will take a break, I'll take like a month off, I'll start this job in April or May, that would be great.” And any one of these seven companies would be perfect. And the story goes that the world didn't look the way that I thought it was gonna look. In March, April, or May of 2020, the retail industry as many other industries were severely impacted.

I was supposed to start Rent the Runway in March of 2020. And there was– so I ended up starting Rent the Runway to give the secret away in July of 2020. But I do remember, during those four months, the question came back again, the question was, well– by the way, there was no you're gonna start in July 2020. It was we'll see.

Diana: “We’ll see if we can even hire you.”

Rolanda: Yeah, we'll see if we'll like– yeah. So there was no– so the question came back, “Rolanda, are you sure that this is what you want to do?” Jens Sincero calls this the big snooze, she called like in the book, and I was like,” Oh, my God, this is literally what's happening to me. I'm being tested again. Am I actually going to stay the course and wait it out to find out this question.”

Whereas in the interim, other tech companies, Instagram, TikTok, Microsoft, Facebook we're like, “Oh, my God, we'll expedite you to the final round. We know exactly you've done this. Let's do it. Anything you want, we can get you there.” And I remember always having this internal question.

I would take the call, and then I would feel so awful after it because there would be this cognitive dissonance of, “Well, I'm unemployed, I should take a job because we're in a pandemic.” But that's not the job that I want.

I just said no to that job when I left. And so eventually, I learned, you don't always have to take the call. That was a piece of advice that a mentor told me, You don’t always take the call. And I would actually argue, “You don't always take the call.” So I stopped taking the calls, because it just made me feel worse, and it made it harder to choose my choice.

I was committed to choosing my choice. So I was like, “I'm going to remove the things that make it hard to choose my choice, until I can no longer choose my choice anymore.”

Diana: That's a quotable quote, holy shit.

Rolanda: Oh, I say choose my like we have– I know that sounds really crazy. But we have like tenets and my boyfriend and I, one of our core tenets like a quote that I say all the time. It's also a quality that I like to see in the other people in my life. Or if there is conflict, I'm like, “Why are we fighting right now? And it's because I need you to choose your choice too. I can't choose your choice for you. So you're gonna choose it or it's done.”

Yes, a core tenet of mine is to choose your choice. Either we're going to do it or not. And so I was like, “We're going to do it, we're going to choose the path that I want to choose.”

Sorry, to all of the LinkedIn requests, but I have to say no. And so I held on with as much hope and positivity that I had during that time, which was really hard, as I know, for many people too. And eventually, the question was answered, and I was able to start in July.

I remember my manager called me, she was like, “Do you want to push it out? Because I know you didn't expect to start in two weeks.” I was like, “Push it out? I will start tomorrow.”

Diana: I'm in the chair– I’m gonna be in the chair tomorrow.

Rolanda: Yes.

Diana: Yeah

Rolanda: Exactly.

Diana: Which also just not a storytime, but like caveat, that you also didn't meet your people in person for like a year or so.

Rolanda: Oh yeah. I just interviewed in person. So I have never been teammates with them in person. And that's what led me to my coach, which was another conversation that I went to you for, because I was just I was like, “This is a challenge I've quite literally never had. I've never been on a team or I've never met anyone. How do you join the team? Build relationships, build a community, build a personal brand?”

Diana: Yeah. As a corporate career woman having a coach as well. It was having support, allowing yourself to get support. I love that. So before we go into the lightning round of things, and I can't wait for you to give your astrology, but where is the blog now?

Rolanda: Yeah.

Diana: What are we doing with it?

Rolanda: What do we do with the blog? Diana, what do we do with the blog? Do blogs exists? Are blogs dead? I don't think that blogs are dead. So I think it's been six years since I first started my blog. And I still create. I think the blog looks different for me now, because now there's so many different ways to create. I know that sounds like– but I could write a blog post, I could do a story, I could create a reel– I don't have TikTok, I can't say I can create a TikTok.

But there's so many different avenues to express creativity. And I think two things I have had to be honest with myself around, like, what kinds of things bring me joy? That's why I created this blog in the first place.

Diana: Right.

Rolanda: So I'm not going to create content, just because an algorithm tells me to do it.

Diana: For sure.

Rolanda: I'm not going to create content that I don't want to create, that doesn't make me happy to create.

I've had to teach myself that it's okay, to follow again my intuition and continue blogging, because that's the thing that makes me happy. And I think that is the creative freedom that I get because it is not the thing that is the source of my income, my full time income. So I understand that that would be a completely different equation, if that were the case. And I think that is what has led me to keeping it as something that is a part of my day, but not my entire day.

Diana: Right. I love that. I think it's– I often tell creatives that if this were your job, which it is like the full time entrepreneurs that I coach, this is your job.

Rolanda: Yeah.

Diana: I know we want– like I'm here for things bringing us joy, and like doing what feels aligned, I am that coach, for sure. But also girlfriend, you got to show up. Because if your boss was looking over your shoulder, you do it.

Rolanda: Yes.

Diana: Treat it like a job, if it's actually your job. You don't just get to sit in a hammock all day. And hopefully, like sprinkle some fairy dust and hope someone comes in clients come in projects come in, money comes in.

But when I think it's so important as creatives, which I love that you had that realization that you were, we have to have something that makes us feel creative. And it's not necessarily always going to be the creative thing that we do for a job, or we're going to start resenting it.

You get to be creative, and you're Rent the Runway job too. But it's like you truly have this thing over here that has no pressure at all, and you just get to kind of throw paint at the wall and do what feels good. Which is really cool.

Rolanda: Yeah, I get to say– I usually say like, I get to be the editor in chief on my blog. And you don't get to do that when you're writing for a company, or writing for a paper, or writing for whatever. And I want to protect that. It is so– it's hard to find places to do– yes, exactly. And so, at least for now, I want to keep it at that special place until I have many lives to live.

Diana: Until you don’t.

Rolanda: Yeah, until I don’t.

Diana: Yeah. I love it. All right. You ready for lightning round?

Rolanda: Yes, I'm very ready.

Diana: What is your astrology if you know your sun, your moon, and your rising?

Rolanda: Ah, this is really funny because everybody at work talks about this. I'm a Pisces and that's all I know.

Diana: Okay, there's gotta be some Leo in there. You're gonna have–

Rolanda: But everyone says to me, “You’re such a Pisces.” And I think that's because I'm really emotional?

Diana: Pisces is, to be fair, gets a really beautiful rap. People are like, “Ugh, Aries,” or like even Geminis, though. They're like, “Ugh, Geminis.” People are like, “Ah, Pisces,” because you're the oldest sign in the zodiac and you're just like really wise, and watery and beautiful, and people really love to be around Pisces, I feel like, you know?

Rolanda: Oh my god. That was like the– I love that. I did not know that.

Diana: You are an old soul.

Rolanda: Oh my god, I totally am.

Diana: Yeah, so Pisces. Got it. You'll have to report back on the other ones because I'm curious.

Rolanda: I will. My coworkers are gonna kill me that I don't know.

Diana: Right? Like what? Okay. What does creativity mean to you?

Rolanda: Creativity to me is reimagining and romanticizing anything like, this people, movement, nature, items. It's so remarkable to see what other people can interpret.

Diana: My perspective.

Rolanda: 1,000% Yes.

Diana: Yeah, I love that. Do you have an entrepreneurial crush? Or it could even be like a CEO of a company or–

Rolanda: Okay, this is gonna sound planted but before I started at Rent the Runway, Jen Hyman, who is the CEO and co-founder of Rent the Runway was my crush.

Diana: Okay. Perfect. Manifested.

Rolanda: I was an on campus ambassador for Rent the Runway when I was in college, and so it is a dream to be able to work at Rent the Runway. But I will leave you with– there is a blogger. A former Googler turned full-time blogger. Her name is Krystal Bick. That is also her handle on Instagram.

When I said to you, creativity on your own terms and making, doing what makes– brings you joy, I think she is the perfect example of that. So I encourage you all to follow Krystal Bick.

Diana: I love that. Love it. I think I follow her. She kind does that–

Rolanda: I think I told you about her.

Diana: It’s classic stuff.

Rolanda: Yes.

Diana: Yeah, in New York.

Rolanda: In New York.

Diana: She’s so– such a vibe. Like very–

Rolanda: Like art. So artistic.

Diana: Just like old school. Very swanky. Yeah, it's so good. Okay, what are you read– Oh, man, back to full-circle book club. What are you reading to or listening to right now? And Rolanda will tell you if she fucking hates it. I think that's the first curse word we dropped.

Rolanda: I literally just devoured– I'll probably gift it to you. It's the book that I'm gonna gift to all of the people I care about. It's called Happier Hour by Cassie Holmes. She was my professor at Penn, and now she teaches at UCLA. The book is effectively how to live a happier life. How to use your time in the way that works best for you. Spending the time doing the things that you care about, and spending less of the time doing the things that you don't care about. How to be present.

I quite literally started it on Saturday, and then couldn't get up so I finished the entire book. So I was like, “I think that's what you know that a book is good.” So, Happier Hour, couldn't recommend it enough. What I'm listening to, I think you already know this, Diana. I'm obsessed with Angela Duckworth, who is the positive psych professor, founder of Grit. And No Stupid Questions is a podcast that I listened to with her and Stephen Dubner. And I just love it. I love– You know that I love Psych.

Diana: Yeah, love it. Okay, last question. If money, time, resources, rent, savings, all the things, parents opinions didn't matter. What would you create, just to create?

Rolanda: I'm going to caveat this question by saying, I fully believe that we have multiple lives and us to live. So I'm going to answer this question, but I don't think that I can't do it. I think that it's just a next chapter of my life. That just isn't the Rolanda that is sitting in front of you here today.

Diana: Love that.

Rolanda: What I would do is– this is so old school. I'm such a– You're so right. I would have a talk show. I was obsessed with Oprah.

Diana: Yeah.

Rolanda: Growing up, I would watch The Oprah Winfrey Show as a nine year old. I don't know what was wrong with me. And I just love the format of sitting on a couch, interviewing someone. Old school days, I would literally have like a talk show.

Diana: Yeah, maybe there's a podcast soon in your future.

Rolanda: Maybe.

Diana: Love it. Rolanda, I'm so stoked to share your story with our audience. For everyone out there listening, tag her. We'll have all our Instagram and all the things in the show notes. Tag her and I if you've listened, we would love to connect with you. And just like hear what resonated, and hear where you're listening from, and all the things.

Just think your story is so expansive to so many people especially that are really wanting to have those high-level corporate careers but follow their dreams at the same time, like the creative dreams. So thank you for being here.

Rolanda: Thank you for having me.

Diana: And I'll see you for brunch, probably in a week.

Rolanda: We're 100% doing brunch in a week.

Diana: Beautiful. All right, over and out.

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