How One Frustrating Shopping Trip Sparked an AI Retail Revolution

It started with a networking event. Not black tie, not casual—just one of those "you better show up and own the room" kinds of things. I had a vision in my head: a blazer with structure, something unexpected underneath, shoes that meant business but still felt bold. Professional, but with an edge.

What I didn’t have? An outfit.

So I did what people have done for decades when faced with an identity crisis by calendar invite: I went to the mall.

The Mission: Find the Look.

And you’d think this would be simple. I had the budget. I had the vision. I even had a free afternoon and backup childcare. But what I walked into was retail chaos disguised as nostalgia.

The perfume hit me at the entrance like a scent-based security system. The floor plan? Same as it was in 1995.

Endless racks.

Harsh lighting.

No map.

No curation.

No chance of success.

I made the store shopping tour—Macy’s, Bloomingdale’s, Nordstrom, Saks. Each store bigger, brighter, and more overwhelming than the last. I wasn’t just shopping. I was foraging.

Even the boutique stores let me down. And I wanted them to win. I wanted to walk in, see a styled mannequin, and just know. But nothing hit the mark. Nothing aligned with the vision in my head—or maybe the real problem was… I couldn’t see myself in any of it.

Maybe it wasn’t the clothes. Maybe it was the disconnect between the dream and the dressing room.

I don’t need a stylist to hand me 12 hangers and hope for the best. I need to be enlightened. I need to feel like I’m not alone in trying to decode silhouettes and shrug my way through trial-and-error.

Please—someone, somewhere—build the thing that helps me feel amazing without asking me to become a fashion psychic.

Style should feel exciting, not exhausting. Empowering, not demoralizing.

I'm not looking for perfection. I just want a pantsuit with sparkle shoes that makes me feel like a boss. Is that too much to ask?

My daughter came with me, both of us dressed for speed, not style. She may have come from swimming in the pool to mall shopping. We didn’t “look like” high-end shoppers that day, and maybe that’s why no one asked if we needed help.

But I was ready to spend. I was ready to say yes.

I just couldn’t find the thing.

Retail Isn’t Dead. It’s Just Directionless.

Let’s be honest: The only reason I even knew what I was looking for was because I’d already spent hours online, saving looks and studying silhouettes. I’d already done the work.

And yet—standing in the store—I was lost again. Blouses blurred together. Dresses all hung limp and lifeless on metal racks.

Nothing was styled. Nothing was explained.

And none of it helped me know how it would look on someone 5’6”, with curves and wide feet and a calendar full of events.

What I wanted was simple:

➡ Show me what works.

➡ Help me see it on me.

➡ And please, for the love of all things retail, don’t make me guess what size I am in a brand I’ve never worn.

We Don’t Need More Inventory. We Need More Intelligence.

I didn’t leave the mall empty-handed. I left tired. Frustrated. Annoyed that this is the current state of retail—when it could be so much better.

And the truth hit me as I sat in the parking lot asking ChatGPT for ideas:

And I say that as someone who builds systems, drives transformation, and helps companies navigate digital disruption. I’ve led teams through AI strategy, built billion-dollar roadmaps, created go-to-market plans for Fortune 50 brands.

I’ve seen what happens when we apply intelligence to outdated models.

And retail? Retail is long overdue for some of these ideas!

The ironic part, is I think the idea is not a big lift and could happen quickly.

✨ Meet: WalkAbout

The in-store AI experience that makes shopping feel like success again.

Imagine walking into a store and scanning a QR code or it senses your presence like a human being welcoming you to the store.

🖼️ “Style me for a networking event. Edgy, smart, intentional.”

👖 “I need pants that flatter and shoes that fit my wide feet.”

🧠 “Surprise me with one wild card piece I’d never try.”

✨ “Mom, you should get a pantsuit… with sparkle shoes.” — powered by 9-year-old fashion wisdom and zero regard for budget

Suddenly:

• The store reorganizes around you.

• Smart mannequins show your ideal silhouettes.

• Screens in each section show outfits styled for your goal, your vibe, and your shape.

• The app guides you through racks—skip the chaos, go right to the win.

• The fitting room shows you similar items, alternate sizes, and styling options.

• Confidence? Restored.

  
  

It’s Google Maps for your closet.

Spotify for your wardrobe.

A personal stylist without the awkward small talk.

The Tech Is Here. The Customer Is Waiting.

People are still going to malls. I saw them—tweens drinking smoothies, parents chasing toddlers, families cooling off in the AC.

The foot traffic exists. But the magic is missing.

Retail doesn’t need a reinvention. It needs a bridge:

From digital identity → to physical space.

From inspiration → to action.

From overwhelmed → to styled.

This Is Not a Moonshot. This Is a Missed Opportunity.

The loyalty data? You already have it.

The AI tech? Sitting on your cloud platform.

The shopper? In your store, standing in front of a rack, trying to figure out what to do next.

We can build this fast. We should build this fast.

Let’s stop treating shopping like a chore. Let’s make it joyful. Intelligent. Successful.

Because I don’t want to spend the rest of my life choosing between Walmart, Target, or another generic Amazon haul.

And I don’t think I’m alone.

Retail doesn’t need saving. It needs to be led.

We need the Customers that Save Retail team.

It needs customer experience imagineers.

It needs engineers of reinvention—people willing to redesign the in-store display, not just for sales, but for connection.

Build the WalkAbout Prototype so we can integrate physical and digital - maybe this is why the Meta Glasses could be useful.

We don’t have to boil the ocean. We can start small—one prototype, one store, one moment of clarity in a sea of confusion.

Let’s test it. Try it. Show what’s possible.

Because the answer isn’t closing more stores. It’s changing the direction of this thing entirely.

And to the next generation—the teens with smoothies and TikToks, the ones laughing in jean shorts and slippers—do you really want to lose the last places that are massive, free-roaming, air-conditioned playgrounds with endless options, freedom, and fries?

👊 Who’s in? Who wants to build this? To pitch it? To make WalkAbout the thing that brings joy back into discovery? Open to naming ideas too!

I think we’ve got this.

Let’s bring back that moment when you look in the mirror and say: “Yes. This is me.”