I’m Desmond. I’m the person behind pinStripe IT.
I wanted to share how this all got started, because honestly, it’s not really a tech story. It’s a New York story.
I came to this city as a two year-old immigrant. Kingston, Jamaica gave birth to me. Brooklyn raised me. Elementary school, junior high, high school, all of it.
For the past 15 years, I have been living in the Bronx. It’s home and I can’t think of living in any other borough. I still love Brooklyn; I go there to visit family and friends and tread on my old stomping grounds. I also frequent the Barclay’s Center as a Nets and Liberty fan.
So when I say pinStripe IT is a New York business, I don’t mean it as a slogan. This city is in my soul.
I knew I loved computers when I received a Talking Wiz Kid as a gift. I played it until I memorized the answers without needing to plug in the cards.
My affinity was further fostered by Ms. Ticotin in the computer lab in elementary school. I thirsted for Word and Number Munchers and any other games I could play on those Apple IIs. In retrospect, I loved the consistency of computers. They were what they were. I didn’t have to guess. I knew what they would do next. That spoke to me.
At Brooklyn Tech, Mr. Poleshuck had old computers in the Media Communications rooms in the basement. I could open them up and touch them. I’d touch the memory chips tenderly at first, getting to know them intimately as if I were learning to read Braille. It made me confident enough to try things and fix my home computers before it was easy to search AltaVista, Ask Jeeves or dig through Yahoo! for help.
Everything in my youth pushed me toward computer work.
People, not computers
While I was “finding myself” in my early 20s, I found myself doing IT work for friends and family. I would travel across boroughs to fix computers for people. I would often not even ask for payment. Whatever they wanted to pay was fine by me. I just loved to see them happy. Fixing some quirk, a virus, anything was sweet to me. Any funds were the icing on the top. More than anything, I enjoyed the people.
I got my first official job at DeepVertical in Brooklyn in 2007. I was blessed to work with Paul, Serkan and Vsevolod. They gave me a good glimpse into the different facets of IT before it sadly closed later that year.
Then I was found by Help with a Smile in Manhattan with Michael. It was the place that fostered me, mentored me. Although we’d often get called about dental work, the business focussed on what I had learned to love. I was helping folks at their kitchen tables, sitting down next to someone who was stressed out because their computer wouldn’t cooperate, and we’d sort it out together. I loved that. Watching someone go from frustrated to relieved never got old. It still doesn’t.
The thing that kept bugging me
Over the years, I kept noticing the same thing. So many people I cared about; nonprofits doing real good in the community, small business owners pouring everything into their dream, startups, folks running the whole show by themselves, were getting left behind when it came to technology. After Help With a Smile was acquired, and as the companies I worked for grew, they would necessarily leave some of those people behind. And I understood it.
It was business.
But why did business have to be like that? That never sat right with me. They deserved someone in their corner too.
So I decided to be that someone
That’s why I started pinStripe IT. We keep things simple and honest, the way I’d want to be treated:
- Everything’s included – Everyone gets everything that they need to run a business and be secure. No guessing about what constitutes a project. EVERYTHING that we do is included.
- Agreements, not locked‑in contracts – I don’t believe in staying in abusive relationships. Leave whenever you want if you find better. You won’t though, because I will treat you well.
- Fair pricing – No surprise charges, no nickel‑and‑diming. We decrease per user pricing as the size goes up. The effort won’t be linear, so why should pricing? And no built-in annual price increases. As you grow, we grow.
- Everyone matters – Solo pros are just as entitled to get an onsite visit as the bigger clients. You are all valued.
- Boutique forever – There is a certain joy that comes from calling a help line and they know you by name. We will always be that way. We don’t want massive clients. We want clients that we can get to know and who know us.
Proud to be a neighbor
Many IT companies do not get the Bronx, Brooklyn, Manhattan, Long Island or NJ the way I do.
I am from here. I am still here. My family is here. My friends are here. I am here physically. I am here spiritually.
I am invested in this city.
I am this city.
We’re proud to call the Bronx home (with an office in Manhattan, too), and we’re members of the Bronx Chamber of Commerce and a CEA Fellow because showing up for the neighborhoods we live in matters to us. We work with people all across the New York metro and around the country.
If you, your nonprofit, business, or startup needs an IT partner who’ll actually pick up the phone and treat you like a neighbor I’d genuinely love to hear from you. Reach out for a free evaluation and let’s talk.