Dear Target: It's Not About the DEI

Last week on Instagram, I shared my take on Target’s recent troubles and asked if you wanted a deeper dive.

100% of you said yes, including a Real Houswife:

My love for Bravo reality shows is (seemingly) boundless, so to see Dr. Moon’s expressed interest meant that I had to commit.

This is my first time experimenting with longer-form content. I aimed to blend personal reflections from years of shopping at Target with data and comparisons to other major retailers.

I had a lot of fun writing it and would love to hear your thoughts! So without further ado…

 ❌Target’s decline is not about DEI

Target has been going through it y’all:

You’ve probably heard about Target’s share price woes. Things have gone from bad to worse in 2025. Earlier this month, the company slashed its full-year outlook, pointing to mounting uncertainty around tariffs, a shaky economy, and softening consumer demand.

Notably, the company pointed the finger at DEI, and rolled back a slew of initiatives that have had negative consequences for black-owned brands selling through the reatiler.

But let us not confuse cause with convenient scapegoat. The roots of Target’s issues go deeper—and they have been there for years. To paraphrase one of my all-time favorite quotes from Vanderpump Rules, “It’s not about the DEI!”

A Confusing Experience—By Design

Even as a teenager back in 2007, something about Target stores felt off. But back then, this was praised as “quirks.”

For starters, the entrances were always on the right. Not the left. This was not an accident—it was a tactic meant to nudge you off-kilter. That unease? Intentional. And it worked—for a while.

Walk in, and the first thing you would see was a clearance or bargain bin. Smart. You came in for toothpaste, but before you could get there, you were offered the thrill of scoring a $5 candle. That dopamine hit? It helped you justify the rest of your cart.

But Target’s layout was never intuitive. The checkout area always felt like a cave. The aisles were offset and staggered, so you would often be standing behind a full line, unaware that a cashier up front was free.

Even as a high schooler, I remember thinking: this is a bad system.

The Original Brand Bet

Back then, Target was positioned as the anti-Walmart. That mattered.

My high school classmates made their own hemp clothes and debated the ethics of big-box retail. For us, Target offered a more “conscious” alternative in an era where Wal-Mart was receiving mountains of negative press for crushing small business. Cleaner stores, better design, and a more palatable brand image. It felt like the cooler cousin who still let you shop on a budget.

Target even flirted with a solid e-commerce strategy. I remember getting free shipping on home goods in New York—an absolute gift in a city with few big-box options. However, Target failed ot invest in digital retail the way Wal-Mart did. Now, it’s eating Target’s lunch:

And the clothing? It was genuinely wearable. I still own a swimsuit I bought in 2012. Target was at the forefront of trendy collaborations - from Missoni to Lily Pulitzer. There was a reason we pronounced it “tar-zhay.

But somewhere along the way, that magic wore off. Take a look at these 2 comments from Reddit, taken almost a decade apart (side note - Reddit is an incredible research tool):

Exhibit A:

Exhibit B (from this year):

Today, the quality feels off. The design is uninspired. And yet, a disproportionate amount of store space is still devoted to these sad, shapeless “Little Prairie Housewife” dresses. It is hard to grab toilet paper without navigating a sea of polyester floral prints.

The Real Red Flags

Critics claim DEI ruined Target. But that is not new, and it is not the point.

I grew up in Louisville, Kentucky, where I remember our city allowing a KKK rally when I was 10 years old. My teachers gave us an honest, heavy conversation about the First Amendment and hateful speech. I remember watching the news and seeing maybe 20 people in white hoods.

The lesson: fringe hate always exists. It is like bacteria—you will never get rid of it entirely, but you do not shut down the body every time it flares up. Social media might amplify these voices, but the hate is not new.

Target’s problem is not a reaction to DEI. It is a reaction to frustration.

The Real Target Problem

Target has become expensive, confusing, and frustrating. They abandoned a once-strong e-commerce play and doubled down on weak categories like apparel. They let design quirks turn into UX nightmares.

From the very beginning, Target embraced contrarianism: doors on the “wrong” side, cashiers hidden from view, layout choices that felt like puzzles. That used to be charming. Now, it just feels like a test of customer patience.

And DEI? That is not the problem. The problem is a company that bet too hard on being clever, and not enough on being clear.

So before you blame the diversity officer, take a look at the org chart. Ask yourself: is the DEI in the room with us—or is it just easier to point fingers than fix systems?

TL;DR

1️⃣ Target’s design quirks and UX confusion were once charming—but now they are just frustrating.
Aisle layouts, hidden checkouts, and disjointed store experiences have long made shopping there feel unintuitive.

2️⃣The real decline stems from strategic missteps, not DEI.
Missed digital opportunities, overreliance on low-quality apparel, and rising prices have alienated customers more than any diversity initiative.

3️⃣Blaming DEI is a distraction.
The backlash is louder, not newer—but Target’s actual problems lie in leadership choices and outdated brand bets, not inclusion efforts.

I’ll leave the last word with another Reddit observation:

🎙 Content Recap

🎧 New episode of Money Memories drops Wednesday! Still finalizing which guest will join, so stay tuned—surprises can be the best kind.

📝 Also, check out my latest Forbes article:
I explore why Europe has struggled to build the next Silicon Valley and what that tells us about the intersection of policy, capital, and culture. Read it here.

📍 Where I’ll Be

If you are attending any of these upcoming events, let me know. I would love to find time to connect:

• May 26 - 31: I’ll be attending Web Summit in Vancouver for the first time. If you are around and want to meet, or have any recommendations, send me a note!

• June 10: I’m hosting my own networking event for founders and investors in Los Angeles. Sign up here to attend and / or share with a friend!

🔗 Other Interesting Reads & Listens

📌The Chinese Adoptees Who Were Stolen: A thought-provoking read. I was surpirsed at how much I related to the identity questions and challenges of adoptees.

📌Sinners Summos the Demons of American Music - I’ve been listening to Switchd on Pop for more than 5 years, and this episode is one of my favorites.

As always, I would love to hear your feedback. Is there something you want to see more (or less) of? Just hit reply and send me your thoughts—or DM me on IG.

Till next week!
💛 Ilona