Let’s talk about Dan.

“Dan” (not his name, but for the sake of this story and his privacy, we’ll call him that) was my boss when I worked at the corporate headquarters of a large retailer.

He was the head buyer of the Men’s Activewear Office and a fantastic manager. Calm, smart, patient.

Our office was a top performer, and it was mainly because of Dan.

I learned a lot from him, but one memory really sticks out.

It was after one of our buying meetings – where brands come in with fabric swatches, design previews, and sample options. Our team decided what to purchase and the merchandise hit the store months later.🛍️

We had our weekly 1:1, and since the question was fresh in my mind, I asked it. 

“How do you know you’re good at this? Isn’t it kind of… guessing trends?”

He chuckled and said, “Not really. That’s why I like this department.”

I looked at him, very confused.🤔🤔🤔

And he explained: “Our customer is usually two years behind fashion trends. They value function and comfort over flash and design. And if their wives are doing the shopping, they stick to the basics. I’m basically just buying what was cool, but not too cool, from last year.”

That was the first time I really understood what it means to know your customer.

Dan didn’t let his ego get involved.

He didn’t need to pick the flashiest or most cutting-edge designs.

He just bought what he knew his customer wanted.

The thing is…most entrepreneurs are not like Dan!

Raise your hand if you’ve fallen into the trap of creating an offering that YOU loved and were totally obsessed with…but your audience either – 

→ had no idea what it was

→ didn’t buy it

→ or felt like it was actually much more than they really needed

hand RAISED🤚🏼🤚🏼🤚🏼

If this hasn’t happened to you yet, you’re either brand new or a business genius. In which case, hats off to you. 🤠

But if you have done this?

Welcome to the club. This is how we learn. Through experimenting.

When an offer isn’t landing, it could be a few things:

• Could be a marketing issue (awareness, messaging, conversion)
• Could be the offer itself (positioning, packaging, price)
• Could be timing, clarity, or a disconnect between what’s cool/trendy 😎 and what’s needed

But if you notice people booking once and never coming back…or getting a ton of interest only for people to go radio silent once they take a look inside the program…

The offer might be the issue.

In those moments, be like Dan.

Dan had a skill (and the benefit of being an employee, not a founder with personal stake in the game): 

He didn’t let his personal preferences override what he knew the customer actually needed.

And here’s a little PSA if you do think your offer is the issue.

You probably don’t need to burn it all down and start from scratch.

Dan still bought basketball shorts every season. But the little choices like length, color, waistband, fabric, and weight could make the difference between “that’s a little out there for me” and “sold out.”

(His customer may never sport a 4″ inseam short, and that’s okay!!)

So go back to the roots.

→ Comb through your feedback and testimonials. (if you’ve got a lot, ask AI to help you find patterns)
→ Talk to current and past clients. Ask why they bought and how they made the decision.
→ Look for the through lines. What keeps coming up?

Then take all of that back to the drawing board.
Notice where your offer may have lost the plot.
And then rework, reimagine, reshare.