There’s Only One Way To Make Men Enjoy Shopping
For Clothes – And Trunk Club Did it

Think back…

When is the last time you were truly blown away with a buying experience?

You know, the kind where you say, “Wow, I just had FUN spending money… (and I’m not even hung over!)”

While it should be every seller’s goal to create that feeling, it’s incredibly rare for two reasons…

One is that most retailers are royally screwing up the process by complicating it beyond any possibility of enjoyment.

(No, I don’t want to save 15% by applying for a credit card today… No, you cannot have my email address… Please stop circling the link to the survey I’ll never take.)

The second reason is that we are trained from an early age to resist the urge to spend money. Why? Because “money doesn’t grow on trees!” And “you should be saving” (for when you’re too old to enjoy it)!

We all bring our own special blend of head trash to the act of spending money.

My wife for instance, gets restless as a bag of cats carrying an eleven-dollar t-shirt from the rack to the checkout at Target. Yet, she wouldn’t bat an eye at plunking down several thousand on a new kitchen because, as an investment that pays a return, it “makes sense”.

I’m the opposite. I can’t make it out of the Gas ‘n Sip without five impulse items I have no logical use for (“Cool! NASCAR trading cards!”). But when it comes to big ticket items, I need reams of research, three quotes, and nine hours of transcendental meditation before I can make up my mind.

Face it… we humans carry less baggage into the bedroom than we do into a shopping cart.

So it makes sense that, as online marketers, we’re thrilled when a measly one percent of our cold prospects actually complete the purchase and become our customers.

That’s why I was stunned recently when I received an email out of nowhere, from someone I’d never heard of, about a service that I’d never even considered, and immediately became this person’s new happiest customer.

Here’s how it went down, and how we can all discover better ways to get in front of our prospects – even if they don’t know they need our stuff yet…

Let me set the scene…

I was in Seattle doing a presentation for a very cool training platform called creativeLIVE. I was brought in as a guest-expert by my friend, Derek Halpern, who also brought along marketing powerhouses Pat Flynn and Melanie Duncan to spill their secrets on the webcast.

Now, click on these screen grabs from our presentations and tell me what you see…

It looks like Derek is introducing two savvy professionals… and a stagehand.

Now, I admit that I dressed down with intention that day. (Even declining Pat’s generously offer to loan me one of the eight neckties he’d brought on the trip.)

But I have a good excuse…

… it was my first time in Seattle, and as a devoted rocker, I was soaking up every remaining bit of the grunge vibe left over from the 90s. Thus, my decision to wear flannel to the gig.

Hey, I don’t regret it. I’m much more comfortable in the role of outcast than main cast any day. But I will admit to being conscious of how stylish my runway ready costars looked and wondering if it wasn’t time to step up my fashion game. That’s why the email I received 2 days later was so eye-popping.

The subject line read: “Kevin, I’d like to be your personal stylist”




It’s important to know that the constant goal of every copywriter is to “enter the conversation” taking place in our prospect’s mind. To do that, you’ve got to be keenly aware of the struggles they face and what REALLY matters to them. Guessing will not do.

And entering the conversation is exactly what this out-of-the-blue email from a woman named Mary did.

The email was brilliantly crafted to win my attention and excite me about Mary’s offer. I could (and likely will) write a separate post breaking down all the great lessons in that email, but for now let’s stay focused on creating a “dream come true” customer experience.

Mary is a personal stylist at a company called Trunk Club, a men’s retail clothing boutique in Chicago.

Her proposal was very simple and completely irresistible to me…

Mary suggested we chat on the phone about how I’m dressing now (she thought it was cool that I went casual on creativeLIVE), how I might like or need to dress in future situations (I don’t even own a suit) and what kind of clothes I’m comfortable in.

Then Mary heads to the racks at Trunk Club’s downtown Chicago retail space, picks out a few outfits she thinks will fit my style (and my gangly limbs) and ships them to my door at no cost or obligation.

I simply keep what I like, the price on the tag is deducted from my card, I ship back the rest (again, for free) and provide feedback on the clothes. That’s it.

We keep this up until my closet represents who I am now, rather than what I thought looked cool on a mannequin or was available six hours before my flight left.

This was huge for me.

It’s like having a new friend with amazing taste in clothes to not go shopping WITH you… but go shopping FOR you!

That’s a dream come true – and I don’t even hate shopping.

Could I find similar clothes cheaper, I suppose. But paying full retail to have clothes hand selected and shipped to my door? That more than evens the score. Personally I’d rather be home earning money, than running all over town desperate to save some.

Even my wife, who takes pride in finding a bargain, was thrilled about it.

Keep in mind, this service was nowhere on my radar. This was a great reminder that you can never assume anything about your best prospects.

I could have latched onto any of 20 logical objections to say “thanks anyway” to Mary, or just ignore her email altogether. There was zero pressure in her offer. No scarcity, no social proof, none of the stuff most experts swear is so critical to closing the deal.

Instead, I sold myself on the deal because I’m committed to reaching more people and image matters. All Mary had to do was remove any friction stopping me and let the rest happen naturally.

The minute the trunk arrived, my wife and I tore it open like kids on Christmas morning. I immediately tried on the clothes… posing for my wife, who happily “yayed” or “nayed” each item.

The experience was overtly self indulgent and completely practical all at once. What more could you want?

PLus the entire process went just as smoothly as Mary promised.

There were no hassle returning the trunk, there’s a user-friendly page for providing feedback on the clothes, and Mary was very responsive to my feedback, without needing any more of my time.

A 100% feel good exchange.

Are you thinking about your own business right now, and how you could incorporate this type of service to your best prospects?

When we experience a buying process this good, it all seems so simple. So why is this the exception instead of the norm?

Why is checking out of the Apple store with a new iPhone nearly void of friction, while getting out of Best Buy with a pair of earbuds makes you need a nap?

How come will send anything I want to my front door with one click, but buying a domain at GoDaddy gives me a finger cramp from clicking “no thanks”.

Because it’s just easier to leave things as they are or follow proven models because “they work”.

Growth means change and most business owners live to avoid the pain of loss just like their customers live to avoid the pain of spending money.

It’s easy to see why the typical buying process is so mired in pain.

And that’s why I get so inspired by companies like Trunk Club who know the risk and do it anyway.

They could have settled for being just another hip Chicago retailer fighting for the small pool of local customers. But instead they took a “what if” and turned it into a “here’s how” and expanded their customer base from “Chicagoland” to the entire United States and anywhere else FedEx delivers.

So, the questions we should all be asking…

What could I be doing in my business to remove the friction for my prospects to become customers?

How could I improve my offers to make them irresistible to my best prospects?

Is there a way I could offer a sample taste – free of obligation – to show the true value of what I’ve got?

And… how can we smoothly enter the conversation taking place in the minds of our prospects and help them solve their problems?

I’m currently waiting on my third trunk from Mary and I’m just as excited as the first. We’re searching for the perfect sport coat to wear with jeans and my faith is strong.

In all I’ve spent no more money on clothes with Truck Club than I normally would, but have eliminated my persistent need to “run to the mall” before a business trip or speaking engagement.

These days I could pack in the dark, board a plane and know I’ll show up in style. It’s a Tony Stark aspect to my otherwise Phil Dunphy life.

Some products sell themselves, (if anyone has a device that will train my dog to use a toilet, I’m ready to read you the numbers off my credit card)…

… but most do not, so it’s up to us to remove every bit of friction we can, and make our customers get excited about spending money with us.

I’d love to hear about a “dream come true” buying experience you’ve had (or even a nightmare that could have been avoided) in the comments.

And if you’re interested in Trunk Club << that’s my personal invite. Free of obligation, of course.



One thing that Mary did not reveal when she approached me was that both Derek and Pat, the guys out dressing me on creativeLIVE are both her clients.

It wouldn’t have spoiled my interest, but it’s interesting that she didn’t lean on that, as many people would have, to convince me to get in touch with her.

Goes to show that when you have a great service, and you’ve become well versed in communicating the benefits, the value speaks for itself.



PLUS: Get fill-in-the-blank templates that instantly establish “Know, Like, and Trust”

PLUS: Get fill-in-the-blank templates that instantly establish “Know, Like, and Trust”
PLUS: Get fill-in-the-blank templates that instantly establish “Know, Like, and Trust”
100% Secure. We Never Share Your Email

100% Secure. We Never Share Your Email

100% Secure. We Never Share Your Email