So I figured Step 1: get the bag, step 2. start pounding the pavement, step 3. orders roll in.

So Roy cranked out a beautiful bag; essentially the one you’ve all admired and ordered. (Smirk. Everyone’s still due a “friends and family” discount. Just email me!)

I put together my first “line sheet” (see right over there ==>) – a retail document giving the specs of an item including measurements, features, picture and (most importantly) the price.

So with my inept power point skills shoved in the background, I put together a faux-power point document in Word and listed the measurements, the fact that my badass bag turned into a backpack, and oh. BTW – it retails for $800.

That was an embarrassing price.

But it was also realistic. Labor with Roy cost $185/bag. Add the $100 for materials, and conservatively estimate a 250% markup for retail (apparently a luxury standard) and we’re at $712.50. Add in marketing costs and discounts and returns and storage and shipping and all the things required in retail and, well…I’m barely making a dime from the bag.

But crunching the numbers, that was the correct price. Further, the luxury world is an $800-2500 world. It’s not messing around in the low hundreds. I knew that there would be a population out there who’d pay $800 for a bag…without even thinking. I’d make fewer bags, but they’d cost twice what I’d originally set out to make. That’s a wash, isn’t it?

Nevertheless, I knew that declaring the price to anyone without bursting into laughter would put my acting skills to the test. I mean – I’d never blow $800 on a messenger bag.

And hopefully I’d establish a brand that could then have a mid-range and low-range subsidiary. I was making the Lexus model, hoping to soon make a Toyota and Scion model.

But first: high-end luxury.

Within a few days, I happily shouldered my new bag and walked door-to-door to a couple dozen men’s and baby boutiques in Manhattan and Brooklyn. I loved so many of these stores – Modern Anthology was my #1 goal, By Robert James, Babesta, Rosie Pope, Bump Brooklyn, Lulu Baby, Barking Brown. I hit dozens.

More often than not, the owners of the men’s boutiques were in the store. They’d listen to my quick schpiel as I tried to make the case that, yes – my diaper bag did fit well into their curated store full of hipster woolen pants and $400 button-downs.

They all said, “Nice. But no.”

As for baby boutiques? To a “T” (is that how one writes that expression?), they all said, “This is beautiful. I love it. Wow, you’ve really thought this through.”

And then I passed them my line sheet (and the price.) And they all laughed. “Sorry. We can’t sell for this amount. You belong in a department store. But good luck.”

And I’d head home. I was undeterred, but confused how to proceed. “How does one get into department stores?” I wondered.

Then I met Tracy.

Tracy was a mother of a child in my younger son’s nursery school. Ours was an neighborhood cooperative preschool. One of the parents’ duties was monthly meetings followed by drinking. Because duh.

I overheard Tracy say she was in fashion. I sidled over, introduced myself, and asked if we could have coffee.


“Like, soon.”


“How about tomorrow morning?”

She laughed. “Sure.”

The next morning I bought her coffee and launched into the verbal story you’ve been reading for the last 11 chapters of “Starting Up a Start-Up.”

I showed her the bag. She said, “This is great.”

“That’s awesome to hear. But ‘great’ doesn’t sell. Is it too expensive?”

“I don’t think so. There is that consumer out there.”

“Right. But I’ve been pounding the pavement and none of these dozens of stores where I’ve door-knocked have responded well. It’s too expensive for them.”

“You belong in a department store.”

“Right,” I said. “But how do I do that?”

“Well, I know someone at Barney’s. I’ll put you in touch.”

My jaw dropped.

“Oh, yeah. I forgot to ask. What is it you do?”

She responded, “I work with fashion start-ups and build them into big companies.”

My jaw dropped further into the ground.

And after picking it up, I charmingly and awkwardly said, “I mean…I don’t have any money, but…could you ever, um…work with me?”

She laughed. “You’re not ready for me. But I can help you with department stores, for now.

I’ll take it.

Does this mean no more pounding the pavement? Hardly.

Next stop? Barneys NYC.