From Pizza to Purpose: What One Black Shirt Can Teach Us About Leadership
An Interview With Jason Donnelly, Owner of One Black Shirt
I first discovered Jason’s post as I was scrolling LinkedIn – job interviews, job layoffs, “buy my course” posts and suddenly, pizza. Huh, let me scroll back.
Wait, this is hilarious… and on LinkedIn.
Between that funny post and Jason’s’ (I dare say) infamous headline, “Possibly 3 raccoons in a trench coat 🦝🦝🦝🧥,” I knew I had to be “friends” with Jason or at least a follower of this pizza cult. Fast forward six months, and I’m still a huge fan.
In recent weeks, the topics have switched from pizza (all good things must come to an end) to a new topic: black T-shirts.
And more importantly, the thought: could one black shirt change everything?
Here’s my conversation with Jason Donnelly — the creative mind, humorist, and founder behind One Black Shirt — about community, storytelling, and finding meaning (and mischief) in the everyday.
Colleen: Can you start by sharing a bit about who you are and your background?
Jason: I’m Jason Donnelly and I have a writing problem. 🤣
It started in college after reading Fight Club by Chuck Palahniuk. I went on to earn an MAED in Education, and then both an MA and MFA in Creative Writing — the dream was to land a cushy tenure-track teaching position. But after teaching for a bit, I realized it wasn’t for me.
I moved to New York, became a creative recruiter, wrote a bunch of books (fiction, self-help, humor — you name it), and eventually recruited myself into Gary Vaynerchuk’s agency, VaynerMedia, where I learned advertising and social for about five years.
Since then, I’ve bounced around the ad world — iHeartMedia, an agency out of Chicago — and now I’m in Denmark as the Creative and Social Strategist at Moxso, a company doing seriously cool stuff in human risk intelligence for cybersecurity.
I’ve got a 4-year-old son, and while I love Copenhagen, I definitely miss the food in the States.
Colleen: You’ve built a community of over 11,000 followers on LinkedIn — what has that experience been like, and what have you learned from it?
Jason: Honestly? It started from a slightly dark place.
I couldn’t shake this thought about AI — that soon it’s not just going to help marketers, it’s going to replace a lot of us. The ones who’ll survive and thrive are the ones with personal brands, real communities, and people who actually care.
Because on paper, so many of us look the same. But when you’re a brand, you have something extra — a voice, a following, a little power.
That said, by January 2025, I was exhausted by LinkedIn. So many AI posts. So many copycats. So many people posting things they thought they were supposed to say.
So, naturally, I started posting about pizza.
Every. Day.
For nine months.
And somehow, that turned into 5,000 new followers and the title “The Pizza Guy on LinkedIn.” 🍕
It was fun (and ridiculous), but also a marketing experiment. And when it ended, I found myself wondering — what’s next?
That’s where One Black Shirt came in.
Colleen: Tell me about the mission behind One Black Shirt — what inspired it, and what’s your long-term vision for it?
Jason: I was ideating around what to do after pizza (which is definitely not a sentence I thought I’d ever say).
I realized I wear black shirts. That’s… basically it.
And then I thought, I wonder if one black shirt could change anything.
From there, it evolved into something more meaningful — could I use my network for good? Could I tell people’s stories in a way that connects and uplifts?
That became the mission.
So, I started making shirts embroidered with “one black shirt” in simple white lettering. The goal is to sell shirts, yes — but also to tell stories with humor, honesty, and the kind of realness that LinkedIn desperately needs.
Colleen: What advice would you give others about telling their story or sharing their experiences online?
Jason: Be. You.
There are enough fake people on LinkedIn — and in the world, honestly. Say what you want to say, do what you want to do, don’t hurt anyone along the way, and you’re good in my book.
Colleen: In your view, what’s the mark of a great leader?
Jason: A great leader balances reality and dreams — while being fair to the people they lead.
They can be tough or hilarious or anything in between, but if they lead with compassion, I’m in.
Leaders don’t say they’re leaders. You just feel it. You don’t follow because you’re told to — you follow because you want to.
Colleen: When you think about the future of work and leadership, what’s one skill you believe will take people the furthest?
Jason: Drive.
The world changes. Trends change. But drive can’t. It has to be constant — always pushing toward something new.
The funny thing about goals is that they never really end. You cross one off and another appears. Success belongs to the people who keep showing up, evolving, and finding joy in the process.
If you haven’t already, go check out Jason’s work and the movement behind One Black Shirt:
👉 LinkedIn: Jason Donnelly
👉 Shop the shirts + join the story