The Making of Ink’d

I've written a few times on how Ink'd Stores was created and each of those stories focused on the hard facts of "what happened" and "when". The facts. If you'd like to read about them, it's here:

How Ink'd came to be and The 7.5-year-old pop-up store.

The below recounts the real life emotions through the process.

When people ask how Ink’d Stores started, I usually smile and say, “Well, I’ve worked every job you can think of.” That’s not an exaggeration. Dishwasher, valet, radio producer, dry-cleaner counter in Vegas—you name it. I wasn’t afraid of hard work then and I’m not now. That mindset has shaped everything about Ink’d.

Ink’d didn’t start with a pitch deck or a big idea. It started with me trying a bunch of stuff, failing, and figuring out what stuck. I had a good run with Marquis Jet in the early 2000s, we went to $1b in 4.5 years, it was my 2nd success in a row and I thought business was easy. That experience taught me what scale looks like, what real service feels like, and how relationships can carry a company.

But then I left to try my own thing, luxury villa rentals, it tanked. Plain and simple. I made mistakes, I got humbled, and I learned a lot about what not to do.

For a few years, I hopped around. My friends would tease me. Being in yourty's and bouncing around opportunities for a couple years is not a laughing matter. Real doubt seeps in, it's embarrassing and scary.

I ran a golf course, I consulted, I built a business on St. Barths. Each of those is a story on their own - but eventually, I partnered back with the Founder of Marquis Jet, Ken Dichter and launched a fitness brand.

The vision was to build a brand to sell licensed fitness equipment, with colleges and pro team logos. We were definitely too soon. So, we pivoted to gym/company branded fitness gear. It was a good idea, but the timing was wrong and the orders were too small and not enough of them.

Again, I was on the verge of failure. But this time, older and wiser. I knew the only thing to do was stay in the game. As cliche as it sounds, my entire existence centered on survival.

And when you get into that mode, you tend to see things you otherwise wouldn't. For years we were figuring out how to do something hard: Decorate substrates like PVC, Foam, Leather and other tough, rugged materials and do it in small quantities. Decoration was core to the business and it struck me, we were decorating products people didn't want.

I had learned hard manufacturing processes, the hard part, and now, I was going to use them on products people wanted. My Ah-Ha moments seem like 'no kidding dummy' looking back.

But as an entrepreneur, you're invested so hard in running an idea, it's easy to lose sight.

In 2015, we opened a pop-up shop in Foxboro, MA, right around the holidays. Just some DTG printing, basic designs, and a little storefront. But it worked. People came in, bought tees, and came back. That was the first real proof that Ink’d could be something.

From there, it was brick by brick. I didn’t have a fancy backend system. I didn’t know a thing about e-commerce. I picked up the phone, I met customers in person, I walked show floors, and I made sure people liked working with us. And slowly, we grew.

Then COVID hit.

Like everyone, we had to make a choice. Close up or adapt. We launched something called Commun-A-Tee (This is getting it's own blog post next week), local businesses could sell tees through our site, we printed and shipped them, and we split the money. It was simple and it kept people going. What I didn’t realize at the time was that it also gave us the blueprint for scale.

That year we launched 35 online stores. The next year, 350. Then 1,000. Real businesses, nonprofits, schools, and brands started trusting us with their gear. From DoorDash to Crocs to successful brands you've never heard of, we became the team behind their t-shirts, hoodies, polos, and swag.

We didn’t win because we had the best tech. We won because we showed up. We answer the phone. We include a handwritten note and a little duck in every box we ship. We care. That’s not a slogan—it’s just how we operate. And it’s what people remember.

Ink’d is built on a belief that real connection still matters. People want to work with people. Yes, we’ve added systems. We’ve gotten better at online stores, automation, and outreach. But the heart of this business is still the same: make good stuff, treat people right, and show up every time.

We just printed our millionth shirt. That number means a lot. It means we’ve helped thousands of companies build their brand, connect with their teams, and stand out. And we’re just getting started.

This business isn’t about swag, it’s about making things people actually want to wear. If you can do that, consistently, with care, the rest usually works itself out.

Thanks for being part of the ride.

– Jay