Be So For Real (Real)
a laundry list of things I'd rather see The RealReal do than have a Substack
In October 2019, on a balmy autumn evening, I resigned from my job as a private client wardrobe stylist for a luxury fashion tech start-up.
I drove home with the radio off, all four windows down, the deafening wind whipping my hair across my face as I descended the winding highway through the Santa Cruz mountains. For the first time in years, the turbulent, anxious tummy ache that stormed through my insides subsided.
I was free.
Well, almost.
By dawn, the digital footprint of my recent past came stomping back with vengeance. Buzzing, pinging, flashing alerts. Discount! Sale! SALE! VIP event! Exclusive! BOGO! Limited time! Back in stock! New! Now! Trending! Buy buy buy!
In my three years at that company, I had subscribed to a truly heinous volume of marketing emails. I spent the entirety of the following day unsubscribing from each and every company, brand, designer, and retailer. It took hours to clear out years of copy that, in retrospect, made me neither smarter nor more discerning. It was content, yes, but not information.
By the end of the day, somewhere between nausea and clarity, I made a decision: I would be intentional about what I consumed about consuming.
My inbox stayed quiet for years, until last February, when I decided to let one that I thought would be different, back in.
I first learned The RealReal (TRR) was dipping their toes into the Substack waters exactly a year ago, via an interview in Emily Sundberg’s Feed Me. Like Sundberg, I was cautiously optimistic, intrigued by the prospect of a retail giant attempting to connect with consumers through a more personable lens, infiltrating what felt like at the time, a decently tight-knit creator collective.
When Sundberg asks why an anonymous, Gossip Girl-esque voice was the decided strategy behind the newsletter’s tone, Kristen Naiman, TRR’s Chief Creative Officer, explains, “We wanted to create a character that’s familiar to everyone but bigger than any individual. The RealGirl is the narrator of our collective obsession with The RealReal. And, because she’s an outsider, whose take is through the customer's lens, she can be more objective when writing about us.”
In its inaugural year on Substack, The RealReal’s “RealGirl” averaged the following:
Read Time: 2–4 minutes
Engagement: 20–60 likes with 0–4 comments
Community: almost no replies/engagement with comments or posting to Notes (I counted three replies in a very quick scroll of their archive, only a few posts where they’ve “liked” a comment)
Consistency: A notable two-month hiatus where they didn’t publish anything
Their best performing posts are ones written by guest editors, Substack creators who already have large, actively engaged audiences like Emilia Petrarca. Their chat page is heavily neglected, overgrown with AI slop/creepy conspiracy theory think-pieces, annoying robot spam and people desperate to get more eyes on their own newsletters (a bit gauche, imo). They’ve only posted in their chat twice, one of which was their bizarre opener of a comically priced $4000 (or was it $6000?) Dior puffy jacket that came with absolutely zero context.
Naiman goes on to discuss the emphasis of community saying, “We show up in a lot of other channels, but we always crave a place to have more long form conversations so it felt authentic to us. We want to create content with depth for our die-hard users. And it’s clear the place to do that is on Substack. So many of our core audience, our TRR obsessives, are already there.”
But none of the work they’ve done thus far quite squares with the ambition of the original pitch. The RealGirl feels antiquated, a little corny and faintly infantilizing. Her tone skews young and too casual, which doesn’t capture my attention or make me revere her expertise, especially with three minute content that feels rushed and often times, a little half-assed, the subtle air of something executed out of obligation rather than conviction. If engaging with their Gen Z consumer is the thought process behind making her so informally chill, I think they’re underestimating the intellect of the girls in their mid-twenties on this platform who are deep in intricate-keyword-search-strategy to find the perfect black satin evening jacket that whispers “The Row” on a beer budget. And as resale increasingly becomes the first stop for Gen Z and Millennial shoppers, that naive assumption feels even more misguided.
As we pass the RealReal’s one year Substack-a-versary, I don’t think they’ve done much, if anything, to “world build” their newsletter into a functioning ecosystem that feels distinct, immersive, or meaningfully exclusive in comparison to any of the hundreds of marketing emails that used to flood my inbox daily or the monotonous “fashion” content I scroll past on every platform. Mediocrity is flourishing, the bare-minimum shallow take often rewarded when it comes to virality and algorithms — nothing they’re doing particularly disputes this. I’m bored.
In this current chapter of Internet culture, there are dozens of micro-influencers, content creators, writers, bloggers, whatever-you-want-to-call-them of every generation educating their viewership/community/die-hard fans on how to find treasure through navigating TRR’s labyrinthine interface. For every “RealGirl” dispatch rounding up a modest ten trend-adjacent finds, there’s a girly-pop on TikTok doing it harder better faster stronger and packaging it in a way that’s fun, flirty, and impossible not to engage with.
PS: The RealGirl also alienates an entire consumer demographic they’ve yet to fully capture: their male-identifying client base — a space that continues to feel largely untapped, especially within the fashion Substack landscape.
Unless the RealGirl is about to spill genuinely provocative tea, I’m not convinced that an “unbiased” outsider looking inward is the sharpest strategy for a behemoth company with a history of mixed reviews and sticky controversies.
In Naiman’s interview with Recho Omondi on The Cutting Room Floor, she waxes poetic (in the glossy cadence of someone painfully media-trained) about this being a transformative moment for fashion, about authentic storytelling, about shepherding a connection with the consumer rooted in genuine love. It’s an appealing thesis, but feels slightly at odds with the third-person caricature they’ve introduced and barely developed, not to mention the broader flatness of their overall social media presence. (But we’ll get to that.)
They’re a company that, despite their flaws and pitfalls, inspire a particularly fervent fanbase with passionate devotion. Naiman notes that the average user visits the site four times a week, a statistic I surely fall into alongside many others on this corner of Substack. (Six months ago I swapped doomscrolling for late-night TRR scrolling and never looked back.)
As a Bay Area native, I’ve spent most of my life cohabitating in tech bro society, observing inferior, mediocre men explain to women what we want, usually in service of whatever artificial intelligence they’re trying to fund. (My fashion-tech styling job was, naturally, run by a man — boo, hiss, tomato, tomato.) So yes, I would like to see a circular, female-founded, mostly female-run company like The RealReal triumph. At the moment, they feel like the central artery keeping the idea of wardrobe sustainability alive, however long and aspirational the road ahead may seem.
I’m a committed romantic to the old and the used, and want it to be known I offer this as loving, constructive criticism. I want a corporation to surprise us in this era of ✨viral marketing✨ with something that feels not just buzzy and of the moment, but enduring, immortal, steadfast!
Corporations aren’t our friends, but at this point in the late-stage capitalism game, I wouldn’t mind one that at least takes some risks to make me believe for one brief moment, we shan’t be parted! If I must be inundated by consumption, let it be by a company evangelizing luxury consignment, something I would gladly take over spending another Super Bowl being bombarded with commercials about AI, GLP-1s or Kendall Jenner pushing sports betting in her private jet.
(A slight digression, but I ✨couldn’t help but wonder✨: where was The RealReal at the Super Bowl? For a company headquartered in the Bay Area, I saw absolutely zero activation from them. Nary a pop-up! a reel! a commercial! I kept imagining an ad set on the frenetic trading floor of Pierpoint & Co., with Harper, Yasmin, and Sweetpea executing a breathless, high-stakes negotiation over what to hold, what to offload, what to covet on The RealReal — missed opportunity, if you ask me!)
So much of The RealReal’s story feels left unsaid, and there are far more avenues to explore than an unenthusiastic newsletter. With 37 million buyers and consigners and 793,000 followers on Instagram, there’s a great big audience ready to lock in.
I want a RealGirl who’s a little more in touch with The RealWorld.
And I’ve got some ideas.
Build a Media Empire (but not the boring kind)
In January, Gap Inc. appointed Pam Kaufman, formerly of Paramount, to the newly created role of Chief Entertainment Officer, a position meant to draw the retailer closer to film, television, and sports, etc etc etc and to bridge the gap (no pun intended) between fashion and entertainment.
If any company were poised to take a similar step, it might just be The RealReal. At present, their marketing feels competent but lifeless. The campaigns are attractively styled, yet narratively static; their Instagram presence veers from “starter pack” memes to random cartoons to influencer hodgepodge with little cohesion. (One can only encounter so many “I wonder what’s on The RealReal” reels before the joke wears thin — it was only funny the first time.)
For devoted users, browsing the site is often described as a hobby. If that’s the framing, then it’s worth considering what sustains a hobby: education, insight, a sense of discovery. A hobby is, ideally, a pleasure—an absorbing diversion from the dull and mundane. There’s an opportunity to build a more expansive, imaginative world around that instinct, one that doesn’t relentlessly pressure a sale but instead invites the user to linger. “Adding to cart” is likely inevitable for the TRR user.
Maybe it means conceding that Substack, for all its virtues, is still just a feed. Perhaps it’s time to imagine something more architectural, something that feels more like a magazine, something where the goal isn’t spectacle so much as atmosphere: a world dense enough with visual pleasure and editorial thrill that you linger, uninterested in toggling back and forth to mindlessly scroll other apps.
If I were sketching out this strategy it might look a little something like this:
Build a sexy editorial platform
Integrate magazine-caliber content directly into the site and app—something closer to Net-a-Porter’s Porter than a blog. Longer-form features (we need in-depth information in 2026), thoughtful deep dives into emerging designers, examinations of color and styling theory, editorial concepts and photography, conversations with serious vintage collectors about archival runway, humanize the editors who shape the assortment! Dabble in profiling people outside the usual fashion orbit, tracing the link between their particular discipline and the art, or science, of getting dressed! Let readers understand the eye behind what’s deemed covetable and create more emotional attachment. Push the narrative that each and every thing on TRR means something to someone.
Introduce a tiered membership model
One that merges content and commerce: themed drops of rare designer pieces, coveted tastemaker edits, exclusive interviews, tips and tricks/know-how behind a paywall, paired with tangible shopping benefits—early access, bundled shipping (I beg of you!) or returns, stylist consultations, etc etc
Invest in (gorgeous, stunning, visually compelling!) video content
We mourn for the days of E! red carpet coverage and the celebrated legacy of Joan Rivers. I would love to see The RealReal step into red carpet commentary, especially if they engage the absolutely-charismatic-mesmerizing-charming babe that is Mary Beth Barone because she fucking dominated that Golden Globes red carpet (do it now, because she’s about to be a mega star!) From there, produce deeper recap segments that unpack themes, moments in history, silhouettes, etc etc then pull visually exciting, shoppable parallels from the site.
Style an entire press tour exclusively in The RealReal
Partner with a stylist and vintage/sustainability-minded celebrity like Hannah Einbinder (Hacks) or Myha’la (Industry) and source every press appearance look from TRR. Document the fittings and decision-making process in thoughtful, process-driven documentary styled videos— like Vogue’s “Get Ready With Me” or “What I Wear in a Week.” Then make each look, along with similar options, shoppable, reframing resale as an intentional styling choice even for public figures.
Lean into professional sports.
As an avid F1 fan, I’m a firm believer the TRR could make a successful entry into motorsports. In 2024, Charlotte Tilbury became the first female-founded company to sponsor F1 Academy—the women’s division of Formula 1—a move that felt symbolic for the future of women and sports. As F1 grows in popularity in the US, pulling in engagement from new demographics of creators, there’s undoubtedly space for TRR to engage in a way that’s exciting and intentional. (Pop up party at the Wynn for the Las Vegas Grand Prix? I’ll host. Holy grail points if you can get Eric Mcneal to dress Lewis Hamilton in head-to-toe TRR.)
This applies to other sports, too, like the WNBA — perhaps a series styling players in TRR pieces for their tunnel fits—styled by someone like New York Liberty superfan Nicolette Mason, merging fashion and fandom with some genuine storytelling.
Get the (Trunk) Show on the Road
It may be time to revive ye olde Tupperware party—call it a trunk show, a traveling salon, a retail roadshow! Shoppers are craving occasions, online browsing only suffices so much.
TRR goes on tour! thoughtfully! selectively! staging pop-ups in cities that rarely receive this kind of attention. (Presumably, their data already maps where their most engaged customers live; why not meet them there?)
In her Cutting Room Floor interview, Naiman notes that some of her friends prefer a boutique environment—someone to help them navigate, contextualize, editorialize the product from hanger to body. A more intimate, in-person format could soften some of the annoyance of scrolling online: sizing ambiguities, wildly incorrect measurements, the eternal puzzle of mannequin photography, and various categories that have never translated seamlessly to the screen.
Some concepts I’d personally love to see:
Bridal
A wedding-season trunk show feels like an easy win. We’re in the era where the unconventional wedding is more popular than ever, the wedded-to-be determined to find something unique, personal.
I imagine something with breathtaking, transportive editorial to back it up. An introductory campaign in the romantic style of Autumn de Wilde’s Emma or her work with Rodarte: lush, slightly theatrical, but still modern. A traveling set that echoes that mood —intimate, cinematic! showcasing off-the-beaten-path options for every stage of the wedding weekend. The appeal is twofold: the thrill of finding something truly singular, and the quiet satisfaction of doing so sustainably.
I nominate the first stop is Las Vegas — I have connections to Elvis, don’t worry.
Denim
I’m calling this the 🎪 Traveling Pants Circus 🎪! Denim remains one of the most notoriously difficult categories to shop—especially in luxury, where sizing can skew narrow, long, cropped, rigid, or unexpectedly generous. A well-curated, size-inclusive edit paired with actual guidance from experts on how different brands fit would transform the experience from depressing frustration into collective discovery! No crying in the department store fitting room here! Building that confidence will bring people back to shop time and time again, prioritizing the plethora of secondhand denim TRR has to offer.
Nurturing the Creator Community
There’s an opportunity to collaborate with independent creators and their readerships—perhaps those building thoughtful communities on Substack (let’s skip those solidified in the Top 10 bestsellers, we need to diversify.) Invite them to curate a personal edit and host intimate styling nights for their readers. People yearn for connection! Commerce may be the underlying structure, but the atmosphere can read more like togetherness. Events like these don’t just drive sales —they reinforce the broader idea of shopping secondhand to those who may not be as familiar and reinforce the importance of shaping your own sense of personal style.
(Maybe this could give some direction to their influencer strategy, which right now feels scattered and unclear—especially as they keep lowering the dang affiliate commission rate! Whoever takes this open position has a lot to figure out!)
Luxury Managers are the ✨Stars✨
As someone who owned very little designer clothing at the start of my career in private wardrobe styling, I naturally understood very little about the mechanics of consigning at The RealReal.
Naiman has said that the challenge isn’t driving traffic or convincing customers to make a purchase; it’s persuading them to part with what’s already in their closets. That feels right. There’s a noticeable gap in the strategy around consigning—one that isn’t solved by a barrage of brightly worded emails or texts from overly enthusiastic strangers (Ryan, if you’re reading this, stop blowing up my phone!)
What might resonate more is a campaign that positions Luxury Managers as the human counterpoint to what can otherwise feel like a vast, impersonal machine. An “Employee of the Month” feature, perhaps, spotlighting an LM from a particular region in intriguing documentary style content. Lean into the narrative—their expertise, their process, a day in the life, what’s in their bag, hearing the stories behind the garments people are consigning, the lives they’ve already lived.
As someone who spends the majority of their time in other people’s closets, I can attest to how intimate and personal it can feel. Channeling that into genuine, honest storytelling might do more than highlight the role—it might inspire someone to give that forgotten piece in the back of their closet a new life with someone else.
Is anyone else completely captivated by The Staples Doll on TikTok? I’m sure by now she’s made her way into every marketing deck from here to Jupiter, but what she’s doing works because it’s simple—something we all too often forget — she talks to people like they’re normal ass humans. Maybe this is the key to finally cracking the code on live shopping, making it feel less like a pitch and more like a conversation. I’d love to see an LM approach like this.
You may be wondering why I’m offering all of this genius so freely. The answer is fairly simple: I’d just like to see something interesting happen! And also, it’s my party, I can whine if I want to.
So much of the internet now feels disturbingly passive—content engineered for glossy, frictionless consumption, little to no depth, context, or conversation. Nothing activates my existential dread quite like a 30-second reel about “what cool girls wear.”
I love the internet!!!! But I’d prefer to feel a bit more intentional in how I spend time there. Even if the end result is likely participation in capitalism, couldn’t it at least make me feel a little electric?
I keep waiting for someone to step forward as a true disruptor, as we hurtle toward being swallowed by a sea of polyester plastic. The pace is relentless; everything feels increasingly synthetic. The RealReal likely does some of these things in some capacity already, but I find the activations they do do, end up in an IG carousel reel never to be seen or heard from the second the algorithm deems it done.
What I’m craving is slower, more deliberate ambition. To sit across the table with someone who values atmosphere as much as output, who understands that creativity needs oxygen. The industry moves so fast now that there’s barely time to think about what we’re making, let alone why.
Let’s make a film. Build a stage —something tactile, dimensional, a little improbable!! Sure, most of this would make a CFO sweat and a boardroom snicker, but maybe it sparks someone to actually try. Let’s get our hands dirty. My DMs are open ;)
They need to hire you
Glenn, this is the most truly thoughtful and well written post I’ve ever read on the stack. You are a genius. You are the moment. You need to be in charge of everything ever. This was amazing and I will be spreading the gospel