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35. Competitive Advantage

35. Competitive Advantage

This is the thirty-fifth chapter of “Scammer,” a serialized novel about ambition, fame, and influence in the age of the Internet.

Helena Holloway’s Competitive Advantage

By Marnie Tucker | May 18, 2016

In Helena Holloway’s world, there’s no difference between Instagram and reality.

I’ve been good friends with her since this past July, when I iced her with a bottle of green-apple Smirnoff, got her onto my boat, and sailed us both off into the sunset. Through all the Nops, video calls, and trips we’ve taken together since then, I’ve never seen her with a hair out of place. 

Helena is basically a Stepford wife who hasn’t been brainwashed into submission. She oversees all of NipNop’s major ad campaigns as the company’s Chief Marketing Officer; since she came on board, NipNop has consistently been the number-one most downloaded app on both Android and iOS. Her own NipNop and Instagram accounts offer delectable glimpses into her days as the most glamorous tech executive in Silicon Valley. Helena is also NipNop HQ’s chief interior designer — we held this interview in its newest communal workspace, a pale pink delight with a rotating carousel bar and several lounge seats shaped like hot air balloons — and the author of her memoir And We Weren’t Like, available in stores next winter.

I’m telling you, this bitch doesn’t miss a single beat! While I’m slurping up my second extra-large strawberry green tea, wondering why the hell I agreed to meet at 7:30 AM in the first place, she’s sitting with her hands folded neatly in her lap, nails painted her signature shade of Cajun-shrimp red. Her drink isn’t even caffeinated. Can you imagine that our literary agent, Wren Falcon, once told her that she should be more like me?! Oh, how the turn tables.


TUCKER: Can I, like, live in your office? It’s much nicer than my current Airbnb situation.

HOLLOWAY: You’re welcome here whenever. I’ve been known to sleep here myself, especially during crunch time.

TUCKER: I’ll be back after I submit this piece.

HOLLOWAY: I’m serious.

TUCKER: So am I. This place is a dream. And the carousel bar is new, right?

HOLLOWAY: It opened last week. I was inspired by Carousel SF [a bar in SF’s Mission District that also opened recently] and wanted NipNop to have its own beverage-serving merry-go-round.

TUCKER: But it doesn’t have alcohol.

HOLLOWAY: That it does not. Elio [NipNop co-founder, current Chief Technology Officer, fellow drink enthusiast] conducted a survey and found that a lot of people here don’t drink, so we decided to make Carousel NipNop serve only boba and fruit tea.

TUCKER: [Finishes drink] I’m not mad about it. Though I’m probably gonna have to take a potty break before this interview is over.

HOLLOWAY: You’ll love the bathrooms. The mirrors are optimized for selfies.

TUCKER: On-brand AF. [Gestures around seating area] Why hot air balloons?

HOLLOWAY: To remind people that they’ll never get off the ground without a little hot air.

TUCKER: You’re great at modeling that go-getter attitude yourself. You designed the entire office on your own, right?

HOLLOWAY: I did, and I supervised the construction, too. Andre [NipNop co-founder, current Chief Financial Officer] called this place “the inside of a Barbie closet” when he first walked in. I think he meant for it to be derogatory, but he’s really grown to like the vibe.

TUCKER: That’s a huge responsibility, putting together the space where all the magic happens on top of your regular duties.

HOLLOWAY: I wouldn’t have it any other way. I’m honored that Oliver [NipNop co-founder, current Chief Executive Officer, boyfriend] and the rest of the NipNop team trust me to get it right.

TUCKER: Does Oliver disagree with any of your decisions?

HOLLOWAY: Never. He once told me that he’d support me releasing a thousand helium-filled condoms into the sky to promote a launch. I love that he’s up for anything. It’s a big reason why I find him attractive.

TUCKER: Would he let you take over as CEO someday?

HOLLOWAY: Maybe. But I’m pretty happy where I’m at right now. Branding is my core strength.

TUCKER: You also take care of all the little details, like making it warm enough inside for shorts and crop tops.

HOLLOWAY: I wear dresses every day, so creating a comfortable environment to exist in was definitely top of mind. My secret is that I’m my own ideal user. By making things good for myself, I’m making them good for everyone else, too. You know, when I moved to the city I didn’t know it would be so cold all the time. I still don’t care, though. I’m always in a dress, no matter what the weather’s like.

TUCKER: I remember that one time when you called me up in the winter, and you were in New York getting ready to meet with editors. You were all, like, “which dress should I wear” … I thought you were going to freeze your ass off.

HOLLOWAY: I did end up buying outerwear on that trip. I got this tea-length princess coat in pale blue wool. It’s the prettiest thing. I have a little collection of dressy coats now.

TUCKER: Good! Ugh, I am strictly a warm-weather person. I can’t believe that it’s only sixty degrees here right now. It’s May! Like, what the fuck. 

HOLLOWAY: Mark Twain did once say that the coldest winter he ever spent was a summer in San Francisco.

TUCKER: Did he? I thought that that quote was misattributed.

HOLLOWAY: Well, someone said it, and they’re right.

TUCKER: Speaking of personal style, I recently saw someone calling you an “ideal of a smart girl who wished that she were pretty.” What do you think about that?

HOLLOWAY: Where did you read that?

TUCKER: … on Reddit, I think? Or some other message board? I personally thought that it was funny, like the opposite of a backhanded compliment. You’re so self-possessed at all times.

HOLLOWAY: I guess that relatability is relative. I aim less to be an everygirl and more to be a view into a different world. Like a friend who goes to a party and then tells you all about it.

TUCKER: I think that’s how I’d describe you to strangers. You did a great recap of Hunter White’s party on Instagram.

HOLLOWAY: I don’t think that her publicity team appreciated that very much.

TUCKER: The best memories come from breaking the rules.

HOLLOWAY: Amen to that.

TUCKER: What would you be doing if you weren’t in tech? Writing a book doesn’t count, either.

HOLLOWAY: I’d probably start my own fashion line. I’d make dresses that look vintage but are comfy and easy to take care of — no crinolines needed, machine-wash-friendly, that sort of thing. I spend an ungodly amount of time taking care of my vintage dresses.

TUCKER: I bet people would snatch them up. You’re so popular online right now.

HOLLOWAY: I sure hope so. [laughs] I’m so grateful for all of my followers. Really.

TUCKER: Does NipNop’s algorithm contribute to your popularity at all?

HOLLOWAY: I purposefully fought for NipNop’s Discovery algorithm to prioritize smaller creators. I know first-hand how frustrating it can be to dedicate your life to making good art, only to feel like nobody appreciates you for it. That’s why Discovery, at the heart of things, prioritizes those with unique viewpoints that may not necessarily be popular. The fact that I’m still showing up so much is a testament to how much we love good stories. Good storytelling is my competitive advantage.

TUCKER: What’s the secret of good storytelling?

HOLLOWAY: Reading a lot … and, like you mentioned earlier, breaking the rules.

TUCKER: Are there any people who don’t like your stuff?

HOLLOWAY: If there are, I have yet to meet them.

TUCKER: Speaking of stories, let’s talk about your new memoir. You gave Wren a completed manuscript that you banged out in a month. Which he still raves about, by the way. How did you do it?

HOLLOWAY: I went to Sarasota with my best friend and collaborator, Nevaeh. She was really good at helping me find the passages where my authentic self shone through.

TUCKER: What is And We Weren’t Like about? Pretending that I haven’t read it yet, obviously.

HOLLOWAY: It’s a memoir about everything that’s happened to me over the last two to three years, and the lessons I’ve gleaned from those experiences. Learning to navigate Instagram in the summer before college. Meeting Oliver. Proving to the world that I was a person, not just Oliver’s girlfriend. Becoming CMO. It’s about truly having it all and being unapologetic about it. Readers will find out how I got to be involved with NipNop in the first place and see even more behind-the-scenes adventures.

TUCKER: My favorite chapter is the scene where Oliver shows you his first pitch deck — the first vulnerable moment between you two. It’s very sweet.

HOLLOWAY: That’s one of my favorite memories.

TUCKER: You two are like something out of a fairy tale. It’s crazy that the entire thing is a true story. Do you anticipate anyone having a negative reaction to you using real names in the book?

HOLLOWAY: I think it’ll be okay. Everyone who appears in the book got a chance to read it, and no one was too upset.

TUCKER: You and Oliver decided to open up your relationship this year. Whose idea was that, and how’s it been working out so far?

HOLLOWAY: The decision was mutual. Both of us travel a lot, and we both just sort of came to the realization that there was a huge opportunity cost to being exclusive. It was pretty cool how we had the discussion, actually. He was away at this conference and I was in LA with a friend of mine, and he called me up in the middle of the night like “I have something to ask you.” I was like, “same. I just met this one girl at a party and I think she’s really pretty …”

TUCKER: Wow. It sounds like you’re on the same wavelength, almost.

HOLLOWAY: We for sure are.

TUCKER: So your arrangement works well.

HOLLOWAY: It allows us to be fully us, without losing any of the love we have for one another. Our bond is based on something bigger than sexual attraction. It helps that neither of us are the jealous type.

TUCKER: Some people will tell you that opening up a relationship is the beginning of the end, but I’ve always thought that that was bullshit.

HOLLOWAY: They have no idea what they’re talking about. And plus, is the truest form of love not creating something you love together?

TUCKER: You sound like a mommy blogger on the cusp of divorce.

HOLLOWAY: Oh, please. I’m never having kids. They’re way too hard to control.

TUCKER: Not to mention annoying.

HOLLOWAY: And sticky. My real baby is … well, I should probably say my real babies are my projects. I sink my heart and soul into every one.

TUCKER: Do you get all protective-mama-bear-like over them? Like, what do you think about Instagram creating a new Stories feature? They’re even calling it Stories.

HOLLOWAY: [rolls eyes] I wanted to trademark the name, but Andre convinced the board that that was an unnecessary hassle. When I get too salty about it, I re-frame things in my mind. Instagram copying us is proof that I — we — had a good concept to begin with.

TUCKER: Are you afraid that Instagram will steal your users?

HOLLOWAY: Not especially. We still have some tricks up our sleeve.


HOLLOWAY: I have to keep the specifics hush-hush for now, but I think what we’ve got planned is going to be a big hit.

TUCKER: Can you spill any founder tea, just to tide us over?

HOLLOWAY: [Shakes head] What happens in the boardroom stays in the boardroom.

TUCKER: Fair enough. We stan an honest leader who sticks to her principles. Are there any influencers whom you look up to?

HOLLOWAY: You, of course. I also really like Cairee Reesemarks. Her account is the first one I pull up when I want to make my palms sweaty.

TUCKER: Oh, Cairee’s great. She keeps telling me that we should all hang out.

HOLLOWAY: You can both come for boba anytime.

TUCKER: Again, will do. How’s it been like, getting so big in a relatively short time? Has your life changed since you’ve blown up?

HOLLOWAY: Surprisingly, not really. I guess I travel more. That’s about it. I’m not really the bougie type, despite all this. [Nods at surroundings] I just like clean, girly aesthetics, not displays of ostentatious wealth. If I were to move to, say, New York City, I would get a nice one-bedroom with a pretty view and an in-unit washing machine. That’s my idea of luxury.

TUCKER: You and me both. Though I wouldn’t say no to a new yacht …

HELENA: Me neither. We’ll have to do a girls’ trip sometime.

TUCKER: Down. What are you most excited about moving forward?

HOLLOWAY: The book release. I’ve wanted to be an author since I started reading.

TUCKER: And how do you feel about that?

HOLLOWAY: Excited! A little in disbelief that it’s finally happening, but I’m so, so excited. I feel invincible most days, honestly.

TUCKER: Like you can do anything?

HOLLOWAY: Anything at all. ♔

Next chapter

Chapter 36: Implementation Details

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