Retail Unhinged

Some retailers start a new pot of water every time the last one hits 190 degrees. Then they wonder why nothing ever boils.

This week Josh and Dane run through the ideas retailers keep bringing them: a coffee bar in the extra square footage, a subscription box, home decor in a fashion store, teen clothing in a kids’ shop. The answer on almost all of them comes down to one question. Are you expanding with wind at your back, or trying to patch a slow core business with something shiny? And when you “trust your gut,” is that your gut talking or your jealousy of someone else’s results?

Also: a big-name jewelry brand with an opening order that made one retailer sick, and the business plan Dane wants you to write before you sign it. A retailer thinking about dropping AI entirely because her posts stopped sounding like her shop (neither host thinks she should go all or nothing). Why corporations are paying influencers to look raw when you can just pull out your phone. The free glass of champagne that keeps customers shopping longer. And Dane’s case that independent retail wins on one thing: weirdness.

A retailer is ready to drop a brand from her store after one cuss word in an ad, and Dane and Josh land on opposite sides of it. One says protect your values and walk away quietly. The other says a brand is allowed an edge if it actually matches who's buying from them.

They also dig into the Black Friday and Cyber Monday question flooding their inbox this year: how do you drive real sales without turning your whole store into a clearance rack. Dane and Josh don't fully agree here either, and that's kind of the point.

Also in this episode:
→ A golf pro shop's plan to launch a full private label collection
→ A boutique testing a pop-up shop inside a salon across town
→ Why "finding the one thing" that'll save your business is a lie
→ Josh's case for why founders need to get on camera, whether they like it or not

If you've ever wondered whether your brand needs an edge to have a personality, or whether Black Friday really is as discount-heavy as everyone says, this one's for you.

Leave a review if you're enjoying the show, it's the best way to help more retailers find us. Got your own good idea, bad idea? DM us, our handles are in the show notes.

Every retailer who's been to a conference knows the feeling. You walked in with one plan, walked out with six. You talked to the live selling coach, the Pinterest expert, the Google Ads guy. You took the best of all of it, built something from scratch, and it didn't work.

Josh did this exact thing with webinars. Studied six experts, built what he thought was the perfect framework, and completely flopped. Then he followed one framework for a year, word for word, no deviations, and it worked.

That's what this episode is about. Also: Dane thinks you're buying from too many vendors at market, and he's probably right. Josh has a credit card setup every retailer attending market should steal. And Dane's retail soapbox is about four words he hears from retailers constantly that are never backed by data: "my customer wouldn't like that."

Oh, and the oldest Gen Z consumer is 30 years old. Josh is not ready to hear that either.

Follow us on Instagram at @retailunhinged

Connect with Josh at @retailjosh or learn more about his company at madebycaptital.com

Connect with Dane at @daneny or learn more about Management One at https://www.management-one.com

First time recording in the same room. Dane flew to Dallas. Josh immediately asked if he owns cowboy boots. He does not.

This week: a retailer considering turning her women's boutique into an Amazon pickup location (bad idea, and Josh explains what happens if it actually works), the right and wrong way to chase specialized trends like pickleball and Western wear, and the debut of a new segment: the Retail Soapbox.

On the soapbox: Josh warns that every company and their dog is about to launch a retail software because building one got too easy. Most will fail. Be a late adopter. Dane walked into a store, spotted a full shelf of new product sitting in the back room waiting for "the new season," convinced the salesperson to bring the rack out, and watched every customer in the store swarm to it. He bought three things. The lesson is obvious. Apparently it isn't.

Also: AI tools vs. agencies, and why waiting for your full collection to land before you launch any of it is quietly strangling your cash flow.

Dane has a warning before you get too excited about AI: Claude will cosign your bullshit. Feed it a bad assumption and it'll run with it. Feed it a bad strategy and it'll tell you it's great. That's not a business tool. That's a yes-man with a fancy interface.

This week: why Josh rewrote all his client resources to move from ChatGPT to Claude (and his take on the coaches who haven't made the switch yet), the fake productivity trap that comes with being able to move so fast in AI, and how to prompt it to actually push back on you instead of agreeing with everything.

Also: a Painted Tree retailer going all-in on live selling, why 100% drop shipping kills the one thing that makes you worth buying from, what the Everlane/Sheen acquisition says about sustainable fashion's failed promise, and how Trader Joe's turned a TikTok pasta trend into a visual merchandising win overnight.

And yes: Josh broke his elbow. His kid's sunscreen did it.

Josh has a name for the strategy most boutiques are using. He calls it UPS marketing: you plan your social content around whatever UPS drops off that week. There's a better way.

This week, Josh and Dane are joined by Brooke from Out of Town Clothing for Retail Receipts and Actually That's Smart. Topics include: the camera fear post everyone's seen in every Facebook group (Dane threw up before his first big presentation, and his actual advice is better than that sounds), and Dane's hot take on wanting to close your store and go fully online: the premise of that question is rude.

Also: why Brooke cut her men's department six years ago and never looked back, the moment she stood in the middle of the mall and walked into whichever store a customer walked into because she couldn't staff both, and whether tightening your weekly launches from 50 products to 25 is actually smart. Josh says your launch is not the curated part. Your marketing is.

If Amazon is your biggest threat, the real problem is that you have no competitive advantage. That's not a dig. It's a diagnosis. And it's fixable.

This week, Josh and Dane get into the Shein conversation nobody in the boutique industry is having honestly: how to handle it when an employee promotes it on your page, how much energy is actually worth spending on it, and why the retailers winning right now have mostly stopped talking about it and started leaning into what nobody else can copy.

Also: a boutique doing $10 million a year in live selling, a vacation, a margarita, some quick math, and a panic attack. The case for building a business that works when you're not in the room. A TikTok retailer doing $3 million a year whose core customer is women 60 and over (Dane is still not over this). And why the Facebook group consensus on how bad business is right now is probably not the consensus.

Your best employee is never going to care as much as you do. Dane learned that from his father. Family retail wisdom passed down over three generations: 70% is the ceiling, and if you get 70%, you're lucky.

But that doesn't mean you accept sloppy folds and phones out. This week, Dane shares the interview trick he used on every single store-level hire: throw some paper on the floor, toss a hanger, drop a tank top. Walk the candidate through it during the tour. If they don't bend down and pick something up, walk them out. That one test tells you everything you need to know.

Also: why "I just don't like being pushy" might actually be failing your customers, the GLP-1 gold mine most boutiques are sleeping on, and a real breakdown of whether AI should be writing your purchase orders and shooting your product photos. Spoiler: one is fine. One is not.

Sales are down this month. Everyone's posting about it. Nobody has money. Nobody's shopping.

Josh and Dane don't buy it.

This week: why posting that question in a Facebook group is already the wrong move, the counterintuitive case for raising your prices when the economy gets weird, and why the local marketing agency that does everything for everyone is a bad idea no matter how nice they seem.

Also: what actually happens when a kid with chocolate hands touches your inventory (and why your reaction in that moment could cost you a $700 sale), whether you should go to a retail event alone, and the one trait Dane says almost every successful retailer shares.

Spoiler: it's not what you think.

Your store next door just started carrying your same lines. A retailer asked her Facebook followers why they haven't been in lately. And somewhere across the country, a boutique owner cleared out her stockroom to set up Mahjong tables.

Josh and Dane get into all of it.

This week: what to actually do when a competitor starts carrying your brands, why asking your customers what they want is usually a terrible idea, and the Mahjong story that had Dane completely skeptical and then completely convinced.

Plus: Dane names the silent killer of most retail stores. Not the economy. Not the competition. A math problem hiding in your P&L that most owners never see until it's too late.

And: should you let AI run your marketing? Dane says probably not. Josh has a Claude tip that might change your mind.