How three close friends turned an encouraging phrase into a business—and why they decided to invite in a new partner.
From left to right: Ejay O'Donnell, Bart Szaniewski, and Grant Eastey. Credit: Dad Gang
The business of Dad Gang is far from child’s play.
Nearly two decades ago, Dad Gang founders Bart Szaniewski and Grant Eastey met when they were classmates at Washington State University. Ejay O’Donnell was introduced to Szaniewski during a business deal shortly after. The trio struck up a strong bond as their lives hit similar milestones involving fatherhood, career choices, and relocations, with Eastey working in personal training and sales in California, Szaniewski serving as director of marketing at a DTC startup in Washington state, and O’Donnell 45 minutes away from Szaniewski, serving as the VP of customization for a global drinkswear company. .
In 2022, the three decided to take an encouraging phrase they often texted each other—“Dad Gang”—and print it on baseball hats for themselves. That first custom creation has grown into Dad Gang Co., a fatherhood-focused social media community and apparel and accessories brand that recently announced they sold their 1 millionth hat, hit over $35 million in revenue, and added marketing guru Gary Vaynerchuk as a partner and active strategic advisor.
“With Dad Gang, it’s just a real business. This is not a thesis, it’s not a pitch deck,” Vaynerchuk told Founder Brew in an interview.
But Vaynerchuk’s decision to partner with Dad Gang went beyond the business fundamentals. “One of the things that was important when I was looking at Dad Gang is their dynamic,” he told Founder Brew. “When push comes to shove, that’s what’s left, not how good of a brim is the hat, or how good of an idea it was.”
In early June, O’Donnell, Szaniewski, and Eastey joined Founder Brew at the Morning Brew Inc. headquarters. Over a long, laughter-filled conversation that demonstrated just how aligned they are with their thinking—they often finished each other’s sentences—the trio discussed how they started their growing brand, inherently trusting each other to make decisions, running a startup remotely, and why they invited another partner into the company.
This interview has been edited and condensed for clarity.
How did Dad Gang go from an idea to a company?
Bart Szaniewski: It wasn’t like, “Okay, so let’s put ‘Dad Gang’ on a hat and start a business, and let’s get the margins right, and let’s do all this stuff. Let me make sure there’s a distributor.” None of that. It was just like, “Let’s make some hats.”
Initially, the thought was, “Let’s make some hats for ourselves,” but you had to make 100 with this factory. And so they came in. We loved the samples.
I reached out to Ejay before making the actual design. I was like, “Hey, let’s take ‘Dad Gang’...and can you give me a cool vintage cursive?” And he just nailed it, first try, and that’s how much we didn’t care. The beginning is like, “Cool, looks good, it’s going on a hat.” From there, they came in, we loved how they looked. And then, well, we have 100, so let’s try and sell them, and we spun them up on Shopify…and then we all individually posted on our Instagrams, like, “Hey, we’ve got some ‘Dad Gang’ hats,” and they sold out in less than 36 hours…that was awesome. Let’s just go make some more and try again, and that’s kind of still to this day the mentality of how we do things.
Ejay O’Donnell: I think, though, we intentionally did that because we didn’t want to bring on unnecessary stress, where there’s a lot of people. Getting started is the hardest part, because people overcomplicate, they got to do some pitch deck, got to get your LLC, you got to talk to your lawyer, then you see all the costs add up. They’re like, “Well, I don’t have enough money to start the business”... We all have full-time jobs. We’re like, “Let’s just see what happens. Let’s not create all this chaos. Just start a business, because I wasn’t trying to start a business.
Why hats? You made them for yourself first, so you were all hat wearers?
Grant Eastey: Yeah. Especially now that I’m starting to— [gestures to his hairline, hidden by his Dad Gang hat]
O’Donnell: That might be a small strategic decision. It’s one hat, one size, one SKU. Super simple.
O’Donnell: Well, maybe then a dad gang t-shirt.
Szaniewski: Then it’s like, “Okay, I think we can support this now.”
O’Donnell: “Designed by dads” on our hats is a tagline that we came up with, because we started building this community online of other fathers all over the world, and they were giving us ideas all the time. We’re like, well, we’re really designing this by dads for dads, so let’s make sure the community is involved. And so that’s where the tagline came into that. And so we’ve evolved because of the community more so than anything.
How long was it just the one product, one hat, one size, one colorway?
O’Donnell: Probably about seven or eight months. And then we started getting the request for, like, hey, “Make a tan hat, make another hat.”
How did you guys decide who’s going to do what?
Szaniewski: Ejay had been in operations forever. I’ve been in direct to consumer marketing, and Grant has been in direct to consumer marketing, but also in sales his whole life, so it’s like [points to Grant] sales, customer service, contracts, [points to himself] marketing [points to Ejay] ops.
O’Donnell: All operations, and then I handle a lot of the design work with our factory and stuff.
Eastey: Then I do all retail. We all have that lane, and we all knew that, but we never discussed it, but we all just knew it. There’s no way I’m going to jump in and try and tell Bart what to do with marketing, because we trust him, because he’s so good at because of experience, Ejay has done operations and design, and we’ve just known that about each other, getting to know each other, and so it just really flowed.
What do disagreements look like?
Szaniewski: The other day, what was it? Grant looked over something that I didn’t have a chance to, and Ejay looked over it too. It’s a contract or something. We were on the phone, and I was like, “Ejay, you saw?” I’m like, “Grant, what do you think?” “Oh, looks good.” I was like, “Looks great.” And they’re like, “You want to look at it?” I was like, “You two loved it. Then that’s fine with me.”
We have been friends for so long that the trust is there. Grant’s a beast at sales and retail. I don’t care to interject myself in that, because it would be an obstacle in the process. Same with ops—Ejay would smack me if I tried to do warehouse work. And it’s the same with him. He’s not going out there and shooting a bunch of content.
It’s a little unheard of when we speak to other founders, but we hate cooks in the kitchen. We just don’t like that process. It removes stress, and then if somebody does mess up, like disagreements or whatever, then it’s on them. We’re not there to be like, “It’s your fault.” It’s more like, “All right, let’s maybe banter about this a little bit.” And brotherhood comes out and then, [we] figure it out for next time. We don’t think any move we’ve made is detrimental to the company by any means. It’s really important to have each other’s back when there is a mistake.
Eastey: I think that also comes to, like, how we never wanted to have added stress. Life in itself is....
Szaniewski: We have toddlers!
O’Donnell: We were constantly talking about business decisions anyway, so like, “Here’s what we want to do. What do you guys think?” And we just hear each other out, and we come to the conclusion we have a kind of an unspoken voting system of like, if two agree and one disagrees, it just is what it is, and we move on.
You two [O’Donnell and Szaniewski] are both based in Washington. When did you [Eastey] move to California?
Eastey:
A little over nine years ago, when my son was one. He just turned 10.
O’Donnell:
I do think this is a good point, though, for founders. We’ve been able to do this remotely...We just actually did a collaboration with Shopify, and Shopify makes it possible to sell things online so easy, so if you go back 10, 15 years ago, it wasn’t this simple for three founders sitting in three different cities to actually create a company together.
How did the trust that you guys have as friends translate into your ability to start this company when you’re hundreds of miles apart, and how does that affect the dynamic of your decision-making?
Eastey: We’re all workhorses. It’s 24/7. I bet that question would be answered best from our lives, to be honest. But we, we really are workhorses. It’s around the clock in our text thread, so we have an ongoing meeting.
Szaniewski: I feel like Grant’s right next to us at all times, or to me, and next to Ejay. It’s this living text thread that just feels in a weird way like they’re just right there.
At what point did you realize this could become a sustainable business?
Eastey: Black Friday, the first one.
O’Donnell: After about eight months of us kind of building a little momentum, it was our first Black Friday, Cyber Monday. I turned my entire house into a 3PL [third-party logistics], like five SKUs at a time. I had boxes of pallets showing up. My whole downstairs just was a pick-and-pack. I had my kids helping, my wife, my in-laws. We had everyone literally just packing hats, and they would load up my truck, go to USPS, they would hate me because I’d have like 300 boxes, which was so many, and I was just doing that every day. Yeah, in my house, and mind you, we all have full-time jobs at this time.
When did you quit your other jobs? Was that something that all three of you did at the same time?
Szaniewski: Mine is 5/22/23. I said no more main gig.
Eastey: I was a couple months prior.
Szaniewski: Yeah, so [Eastey] jumped first. For me it’s like, “Look around, like this thing is growing.” Some of us only get one shot at this, like Eminem says…
Eastey: If this didn’t work out, I’d go find something else. I could always land on my feet.
Szaniewski: This one just feels right, so you might as well jump, or take the leap, and so that was kind of it for me. Then, as you’re having boxes stack all over the place, and we’re having like Mookie Betts, Dak Prescott, Russell Wilson wearing our hats, it’s like you’re silly for not taking this chance at this point…Obviously, I had a discussion with my wife around how things are going, and if we can afford for me to even do this, but it just made sense.
O’Donnell: I just went no other work 31 days ago…I juggled it as long as I could, and it was almost like not intentionally resisting it, but it was definitely resisting it in a sense, because it was like a comfort thing. [My last employer was] still paying my entire family’s healthcare, so it wasn’t like a burden for Dad Gang at the time. There’s a lot of positives, but also it was slowing down some things, too…
I probably had the softest transition because [Dad Gang] was already well-established. We had all of our systems in place, and it was really just like closing one laptop and just staying focused on one, and I mean, we have not stopped since.
It’s just the three of you guys right now in the company, but you’re bringing in Gary Vaynerchuk. What made you decide to bring another person into the family?
Eastey: We’ve watched his content and lived and breathed it for so long...Bart has read every single one of his books, probably 12 times. He’s listened to probably every podcast he’s ever done, and we’ve just really lived his lifestyle...I feel like I’ve known Gary.
Szaniewski: Yeah, it just felt right…My mentality in marketing has been based off a lot of stuff he preaches…I’m on the StairMaster at the gym watching GaryVee YouTube videos until they’re done, no matter how long they are. So I was just dripping sweat watching these videos and just trying to consume a lot of this content because it resonated with me…This feels right, bringing on the biggest community builder there has ever been, in my eyes. Let’s work with that guy. All very organic.
O’Donnell: We weren’t really thinking we needed to bring on a fourth, like we technically didn’t need to, but it’s like, why wouldn’t we if this opportunity is here.
What do you wish you knew years ago when you were starting off on this journey together?
Eastey: Founding something can be highly criticized by people who don’t genuinely love you, because they’re looking at what you’re doing and they may not have the fear to take the leap themselves. As a founder, you’re taking a very profound leap in a belief in yourself that you are capable of building something that’s going to last…Don’t worry about what other people are saying, just do what you need to do for your own heart, and just have those horse blinders on.
Being a founder, when it does finally resonate, and those seeds turn into that plant, and that plant starts to bloom? That’s probably the most rewarding feeling that you can have, not based on the monetary success of it, but based on “You did it.”
