The “Problematic Girl” Era

“My entire life right now would be completely different (in a good way) if I had a friend like Maggie 15 years ago. I was a pivotal moment in my career and really needed this kind of advice. Saving this and sharing with my nieces and my younger friends. ❤️” - Ginger, podcast reviewer on Spotify. If you haven’t already, rate, review, and subscribe to the show on YouTube, Spotify, or Apple!

ICYMI ⋆˚✿˖°

HAPPY SUNDAY HSR!

I’m writing this sitting in the cherry capital of the world’s airport, waiting for Lucky #3 to get off his transatlantic flight so we can see each other after 2.5 weeks apart. In addition to glowing up my appearance this week thanks to my ChatGPT prompts (specific prompting tips below), I spent my week at home obsessing over the fact that women are entering into their problematic era, and it’s not what you think, it’s so much better.

It all started when I got back into my journaling routine every single day this week (even in my 31C economy seat before 8am to Traverse City, Michigan), and I often wrote down affirmations of qualities I love about myself but are sometimes misunderstood. So I posted a video about it, and it seems to have resonated with a lot of HSR girls.

That, plus the resurgence of DTC Darling Founders like Ty Haney and Audrey Gelman from The Wing making their well-deserved comebacks, really got me thinking about what a “problematic girl” is, why the world has had such a hard time with them - and why I think we’re entering the “problematic girl era” in brands, culture, and capital.

As the worlds of culture and capital become more merged (it was evident looking at the Sephora Store Managers Conference 2025 Booths featuring celebrity founders like Hailey Bieber, Jen Atkin, and Mary Phillips, with next-gen beauty founders like Amy Liu or Dianna Cohen in attendance), we’re waking up to the fact that the female leaders of the future are unapologetically themselves. If Hailey Bieber can be respected by Sephora, why can’t Susan Yara if she wants to post the same type of pics in a bikini? Well, I think in this era, she can.

🪞 Top Prompting Tips to Try for AI Color Analysis with ChatCPT

♡ Be Specific - Don’t Say “What color season am I” ask a question like ““What is the best way to have you help me figure out my color theory?”

♡ Use imagery! Don’t be afraid to upload a few selfies

♡ Treat it like the most experienced color theory analysis expert. If you’re not sure what something means, ask it to explain multiple layers deeper. The more information you give it, the better!

♡ This Week’s Mood Board ♡

♡ Consumer Trends The HSR Angels Gossiped
About Most This Week ♡

♡ dairy is so back. I’ve been saying this for years, but the market is finally catching up. Brands are starting to pivot away from plant-based milk and back to whole dairy—and one of the boldest moves yet just dropped: Dream Pops is officially introducing dairy after years of only plant-based products, launching exclusively with Whole Foods. I spoke with the founder, David, and here’s what he told me about what’s going on behind the scenes: “Extremely challenging market dynamics for plant-based. Buyers and category managers are deprioritizing it in favor of grass-fed and A2 dairy. Dairy is 95% of the market. Plant-based is 5%.”

♡ Female founders are already seeing the power of female-led capital. OneSkin—co-founded by four female scientists—just announced a $20M raise from Prelude Growth Partners, just one day after Prelude revealed their $600M third fund (closed in three months!!). I’ve said it before: if you want more women funded, you need more women writing the checks. This is a win for all women in business.

♡ Should beauty brands be built slow and steady? Merit certainly makes the case. In a beauty world obsessed with trend cycles and fast drops, it’s refreshing to see brands win by doing the opposite: slow, steady, intentional. Rhode launched just 12 products in 3 years. Merit? 18 in 4. Turns out, slow and steady might actually be what wins the race.

♡ The Girl Boss era is dead and we’ve officially entered the Problematic Girl era—because the DTC darling female founders are so back, with Ty Haney, Audrey Gelman, and Yael Aflalo at the helm as reported by Emma Hinchliffe.

♡ Even the biggest media companies in the world are buying influence. Katie Feeney just secured the bag with ESPN to lead their social and digital content. Proof that it pays to be that girl—unbothered, unconventional, and unapologetic (and problematic).

♡ InStyle’s The Intern Season 2 just dropped—and it’s even better than the first. @mickeycashflow, it might’ve been just one line, but I swear you made your acting debut. Someone get this girl an agent

♡ HSR Podcast Updates♡

Last week’s episode was a good one 👏

Dianna Cohen came through with some of the sharpest, most grounded advice we’ve heard in a while. With so much news around beauty brands struggling, we dug into how Crown Affair has carved out real success — and why staying sharp and hungry matters more than ever.

From fundraising to spending smart, Dianna’s insights are 🔥 "Give your kids enough to do something, but not enough to do nothing." One of many gems.

Catch up if you missed it!

♡ Consumer News ♡

♡ the brands, people, places, things that have captured my attention ♡

♡ Women’s Health & Beauty ♡

• Youthforia announces its closure after four years, ending the run of its viral blush and playful aesthetic. – Cosmetics Business

• Martha Stewart unveils new skincare brand Elm Biosciences, focused on aging well and launching September 2025. – Instagram

• Glamnetic partners with Fanatics for a lash collection celebrating NFL, MLB, and college sports fans. – Instagram

• AG1 introduces three new flavors—Tropical, Citrus, and Berry—for its signature greens supplement. – Instagram

• Sephora hosts its Store Manager Conference, building team excitement for Fall 2025 launches. – Byrdie

♡ Media, Entertainment & Creator ♡

• Amazon shuts down Wondery’s podcast studio in a major reshuffle of its audio strategy. – Bloomberg

• InStyle revives its Gen Z scripted series The Intern for a third season with a new cast of chaotic assistants. – TikTok

• True Religion leans into exuberant marketing, and it’s already paying off. The denim label’s bold, nostalgic campaign is capturing attention and sales — authenticity turns profit. – Glossy

• SKIMS drops the “Campus Collection”, starring real college students modeling tees, sets, and pants for back-to-school season. Retail meets relatability. – Instagram

• SKIMS goes TikTok viral again with its back-to-school launch — users can’t stop saying, “Makes me want to go back to college for real.” – TikTok

♡ E-Commerce, Retail & Social ♡

• Spanx and Bala team up for their first activewear collaboration, blending compression and sculpting with fitness. – PR Newswire

• Claire’s files for bankruptcy protection as it struggles with debt and shifting teen shopping behavior. – CNN

• Heaven Mayhem debuts a pop-up at Selfridges, complete with photobooth and book box walls — pop-up retail, but make it luxe. – Instagram

♡ Tech, Business & Investing ♡

• Prelude Growth Partners raises $600M for its third fund to back female-founded and consumer-first brands. – Buyouts Insider

• Sensorï closes a $100K seed round for its AI-driven biofeedback devices in beauty and wellness. – AfroTech

• LeBron James and Maverick Carter announce plans for a $5B international basketball league. – Complex

There are lots of $10–$30M businesses out there doing exactly what you’re doing. I’ve seen firsthand how many of them are struggling to survive. Not because their product stopped working, not because the founder isn’t smart enough, but because their brand identity is stale and no longer resonates with customers.

Brand identity isn’t just a logo, a font, or a tagline. It waterfalls down into product assortment, category strategy, and what you’re actually selling your customer. When that identity isn’t clear or compelling, it leads to bad strategic calls that eat time, cash, and customer trust.

I’ve watched startups, all with finite time and resources, make the same mistakes over and over:

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