02. The Insider's Guide: Chloe Under $300, The Real Reason Founders Get Ghosted, and ShopTalk's Power Moves
Gatekeeping is the new black + why boundaries and meditating are your real MVP
Hello to the one place on the internet where I can really talk my shit!
I am back baby… to Vegas that is. And tbh, the transition from Miami's energy back to my normal reality has been a journey.
This week has been back to the basics - calls with founders, prepping for next week's ShopTalk, and honestly, trying to recalibrate after a week of minimal sleep.
In the sake of full transparency, I am feeling not so creative, slightly burnt and a lukewarm level of overwhelm. This video sums up exactly how I’m feeling and I’m sure it resonates with more than a few of you.
credit: Charismatev
I’ll cut straight to the point - today's newsletter feels much more startup + advisor focused than strictly fashion content but it’s an honest reflection of where I’m at today. If last week I was strolling through the glorious 4x2 block also known as the Design District- this week’s equivalent has been sitting behind my computer, over caffeinating and rethinking my google calendar’s booking page (kidding!).
What you can expect today, a little TL;DR if you will:
1. Startup spotlight: The NYFTLab cohort that signals where fashion tech money is actually flowing
2. Real talk straight from my notes app: the right and very wrong ways to build relationships as a founder
3. My thoughts on Shoptalk: + why gatekeeping is suddenly cool again
4. Currently processing: An idea I'm thinking of for founders who have questions but can't get on my calendar
5. An under $300 Chloe haul: straight from TRR to get you excited about summer during these last cold weeks
6. And lastly, my founder toolkit: a few resources I'm currently recommending to everyone who asks
First things first- let’s set the vibe. Wrap yourself in that Tekla robe you justify as "work from home attire" and pour something that matches this week's energy— and I can guarantee you it’s not the $16.50 shipping fee on a case of SipMargs. Get comfy! Get cute! Get into it!
It's Thursday night, we're talking all things fashion, business and founder realities, and even on my burnt-out weeks, I deliver.
Let's get into it, shall we?
TheSkimm's Strategic Exit: Ziff Davis's Everyday Health Group just acquired TheSkimm, and it's a textbook example of audience-value alignment. While the financial terms weren't disclosed, this deal highlights exactly what I've been telling founders for years: a highly-engaged, specific audience is often more valuable than broader reach.
TheSkimm built a loyal community of millennial women who trusted their curation - precisely the demographic Everyday Health needed to round out their portfolio.
The lesson? When you own a direct line to a desirable audience's attention, you maintain leverage even in challenging markets.
The girls are putting out the bat sign: After Eshita’s brilliant community angel raise announcement for By Rotation, others are following her lead (can you blame them?).
Companies like Endless UAE and Diem are testing similar models, recognizing the power of activating their most engaged community members as micro-investors.
The strategy is particularly smart for fashion tech, where community validation directly translates to early adoption (and let’s be honest- funding remains challenging).
The playbook is clear: build authentic community even pre-MVP, consistently deliver value before asking for anything, then give your most passionate supporters the opportunity to participate in your growth financially. When executed right, you get more than capital - you get evangelical super-users who feel genuine ownership in your success.
This approach won't replace traditional funding, but it will create a foundation of advocates who will champion your brand at every stage. If you're building in this space, start mapping your community strategy like… yesterday.
NYFTLab announces its 2025 cohort for the future of fashion tech including: Slip, LiquiDonate, Vody, Athena Studio, Spangle AI and KSI Vision. Looking at the lineup, it's clear we've moved to infrastructure plays - with most startups tackling backend operational challenges through AI (which based on the feedback I get in most calls: AI + VC = 4ever rn. It’s the first question on every investors mind).
This shift reflects where the real money is flowing in fashion tech now: solutions that directly impact brand margins rather than consumer-facing innovations.
The success of alumni like Raspberry AI (with their recent $24M a16z-led round) confirms that enterprise solutions might not be as sexy, but they're where the sustainable businesses are being built.
And if you’re a B2C or D2C fashion tech company- don’t worry I still think you’re sexy too ;) Plus there is plenty of current fundraising success stories!
I spend half my waking hours on calls with founders wanting advice on their ideas, marketing, pitches - you name it. I could not love it more. However, within 2 minutes, I usually know which ones have real potential vs those who have created a solution in search of a problem.
Here's the truth: I'll back a strong founder with a decent idea over a brilliant idea with a founder who can't adapt or show EQ every single time.
Your product will change (and absolutely should) as you build community, find PMF, and navigate economic reality.
The founders who actually succeed aren't just the ones with the perfect pitch deck - they're the ones with unwavering confidence and absolute passion, paired with the self-awareness to see beyond their own vision when necessary.
My advice? Within 30 seconds I should know what you do and why you LOVE it.
On the same line of spending my days taking calls from founders- I listened to this episode of Female Founder World with Annie Evans of Dream Ventures and one thing she said stood out to me with the quickness: “Pro tip: If you’re reaching out to someone, position it more as needing a sounding board because they’re an expert in x y and z and you want to share something with them, rather than picking their brain.”
Look, what I’m about to say is with all of my love and only meant to help! I (and many others) want more than anything to help founders- that's why we take these calls. But walking into what should be a casual connection and immediately hitting someone with "if you find us funding we'll pay you a commission" is... a choice.Let's be real about what that is - you're asking for free biz dev work from someone you just met. It's not that people don't want to help, it's that you're treating them like an unpaid intern rather than someone to build a relationship with. Half the time we’re being asked and haven’t even seen your pitch.
The founders who actually build powerful networks understand this dance and they see relationships as a two-way street. They're not expecting someone to risk connections they've spent a decade building for someone they met 15 minutes ago.
So by all means, reach out! Ask questions! Put yourself out there! Just be transparent about what you're looking for so everyone can come prepared to make it worth the time. <3
Coming from the corporate world, I was always so intrigued by the fact that brands weren’t treating these industry shows as more realistic applications / activations à la influencer events for their consumers (you know, the companies who are literally there to be sold to with DEEP pockets - it's brand-eat-brand out there and everyone's been playing a little too nice the past few years), but I am happy to say that there are some interesting events surrounding this week and it’s about time.
Personally, I’m not interested in another Women’s Breakfast with someone trying to sell me their course anymore but you do you!
At the sake of my own safety some of the events I’m looking forward to are:
1. ADWEEK House at the Four Season's penthouse:
THIS is what I mean about activations.
Beware- I'm about to go down a rabbit hole.
While everyone's buzzing about "fandom marketing," what's actually happening IRL is a return to exclusivity.
Gatekeeping is suddenly cool again (as Vogue Business recently explored) but this isn't just aesthetic gatekeeping - it's community gatekeeping that's defining the shift.
Reddit subcommunities are thriving, IG broadcast channels are being ditched for private Slack and WhatsApp groups, and paid membership cohorts are exploding (and lets be real, politics has only accelerated this over the last ~4 months).
The real behavioral change we're not discussing enough is that people are, dare I say, desperate for genuine connection - not being dumped into a "community" of 10K strangers where they're just another passive recipient of one-way drive-by broadcast channels via IG throwing early sale deals at them.
Safety, true belonging and deep foundational relationships are what’s moving everything forward.
Consumers want the velvet rope experience - not because they're elitist but because true community requires boundaries.
Seeing brands finally apply this insight through intimate gifting suites and connector houses at these mass scale events shows they're catching up to what their audience has already figured out: in 2025, the most valuable spaces are the ones not everyone can access - because in an age of information overload, curation of both content and people has become essential.
Which is exactly why these brand activations at industry events make perfect sense - these companies should be creating the same exclusivity and value for their actual buyers (other brands with serious budgets) that they're so eager to create for consumers who may never convert.
2. PostPilot, Fairing, Klaviyo, Nedap, Smile.io Strip 5k Run on Wednesday: There’s a few brands hosting runs (including this one from Nosto and this one from iamota) and I LOVE to see it.
Gimme more casual, low pressure networking with a built in commonality. Again- micro communities for the win. I think I rambled on enough about this above ;)
There’s so much going on and I’m genuinely excited. Shoptalk remains one of my favorite events, namely for the fact that their speaker line up is 100% editorial (ie: no pay to play. Just truly earned positions for the highest quality info)
If you’ll be around please DM me on LinkedIn- I would love to set up time to chat.
I'm thinking about launching a founder AMA series and genuinely want your input on this. Think of this as my ~office hours~.
Should I create a Typeform for question submissions? Would you prefer this as a standalone newsletter or just a regular section in Retail Roundtable? Maybe a live webinar format?
The goal is twofold: 1) provide targeted help to those I can't always schedule calls with/those who maybe only have 1-2 questions and 2) share answers publicly that might help others facing similar challenges.
I see so many patterns in what founders are struggling with - why not address them where everyone can benefit?
So tell me - what format would actually be useful to you? I am completely open about how we do this, I just want it to deliver real value.
Puhlease share your thoughts in this survey- I pinky promise it’ll take less than a minute!
We’re all having a Chloe moment and I won’t apologize for it. Here are my best finds from TRR all under $300.
My first ever designer bag was a red leather Marcie for my 21st birthday and it is one of my most prized possessions and remains the tether to what keeps me so emotionally invested in this brand today. There’s not an era I don’t love and I thank my lucky stars every day to be alive and witnessing Chemena Kamali do her absolute fucking thing with this house. I’m not being dramatic when I say that the F/W 25 show almost made me cry. Seeing someone be so unimaginably good at what they do and just have their moment in life knowing they’re doing exactly what they should be doing- ugh, brings me to tears.
Let’s shop!
See what I did there?
Use Digest: Beyond just another email aggregator, this tool has completely transformed how I consume industry content. Instead of drowning in subscriptions that I never read, Use Digest curates everything from my substacks, news sources, calendar, weather and RSS into one personalized cutie cute daily email newsletter made just for me <3 ~swoon! The unexpected benefit? It's saved me at least 45 minutes of scattered reading time each day. I can get all of the headlines I need without endlessly scrolling, decide what’s important enough for me to dig into, and keep it moving.
I don’t feel like this one is too much of a surprise but if you’re looking to grow on LinkedIn (and if you’re not- we need to talk) then it’s a must. Kleo is a Chrome plugin to show you the most viral posts within your network so you can create more targeted content. This link has over 160 post templates with examples so you don’t have to overthink your content and you can grow baby grow!
Mental clarity is your competitive advantage. This perfectly timed meditation takes exactly five minutes but delivers the focus of a much longer session. I do this before touching my phone every morning, and it's the difference between reactive founder mode and strategic leader thinking.The short length makes it easy to maintain consistency, even on your busiest days.
Market Edit: Consider this my most shameless plug ever, but if you're a founder navigating the fashion and retail landscape, this is literally why I built Market Edit. From untangling your positioning to crafting a pitch deck that actually resonates, I'm your strategic partner who gets both the business and the culture. Book a strategy session if you're ready for some unfiltered intelligence that moves the needle (ngl, hate myself for saying that one) and an absolute ride-or-die champion in your corner.
If you made it all the way here then honestly, I love you! And I think we’re best friends?
As always, if something resonated, please let me know.
If you’re going to be at ShopTalk- let’s connect.
And if there is anything at all that you want to hear about in next week’s ep, I want to know what it is!
All my love xx,
Carly