Michael Astorino recently walked into his favorite campus smoothie shop with two things in mind: an order and an offer. He cued up his laptop and gave the owner a pitch deck presentation, which was meant to benefit his Wesleyan University basketball teammates while also helping drum up business for the store.

The deal: If she gave players 50 percent off their smoothies for a limited time, he would create a mini-campaign for her — complete with digital content promoted on social media — in conjunction with Wesleyan hosting games on the first weekend of the Division III men’s basketball NCAA Tournament. An arrangement was agreed upon.

Wesleyan (26-1) begins NCAA Tournament play Friday night at home against Delaware Valley (15-12). The winner advances to a second-round game on Saturday night. If you should be in Middletown, Conn., from 9 a.m. to 3 p.m. on Saturday, you can stop by The Fresh Monkee, order from the signature player smoothie menu and receive 25 percent off — all because Astorino saw a name, image and likeness opportunity.

Wesleyan is having a historic season, earning the No. 1 overall NCAA Tournament seed while setting the single-season program record for wins. The Cardinals will attempt to make it out of the first weekend and reach the Sweet 16 for the first time. Yet one of their most intriguing stories comes from someone who likely won’t play.

Astorino, a 6-foot-5, 195-pound junior from Upper Dublin, Pa., has appeared in five games all season for 11 minutes. He doesn’t have a large personal brand. As of mid-week, his Instagram account had 2,289 followers, and his X account had 148 followers. Still, he has managed to carve out a niche in the NIL space, unlike many college athletes at lower levels, through an insatiable curiosity and work ethic.

Astorino, who has partnered with more than 15 brands, co-founded an NIL agency. He earned a part-time job as head of partnerships for a vegan protein company that stemmed from an NIL deal. He is even co-facilitating a “Wesleyan Shark Tank” course that teaches students how to pitch businesses to potential investors.

“He has an entrepreneurial and creative spirit that is in the top 1 percent of guys that I’ve coached,” Wesleyan basketball coach Joe Reilly said. “He’s in good company. I think the difference with him is that he’s taken a non-traditional path, and there’s no blueprint for it. He’s creating it himself. That within itself is the most impressive part.”

Most people likely think of NIL opportunities as they relate to Division I players or the best players on major sports programs at lower levels. Astorino is proof that ambition and hustle off the court are just as important, if not more, because there are few collectives or agents for Division III players.

Astorino said he was inspired, in part, by Jack Betts, who played football in the same conference at Amherst College and graduated in 2023. Betts said he earned around $9,500 combined in free product and total compensation. But he amassed more than 35 NIL-related deals, earned the moniker “The King of D3 NIL” and used that experience to found The Make Your Own Legacy Academy, a first-of-its-kind NIL education solution created to help underserved small-market athletes.

When Astorino was a freshman, he reached out to Betts seeking advice.

“I told him, if you want to find success in this realm, you’ve really got to go out there and get it,” Betts said. “It’s going to be difficult. There’s going to be a lot of no’s coming your way. But it doesn’t matter how many no’s you get. It’s not the end of the world. It just matters about that one brand that says yes. It just matters about that one contact that’s like, ‘Yeah, absolutely. I’d love to sit down and chat.’”

Astorino attempted to connect with brands through email, Instagram direct messages or LinkedIn searches looking for a marketing representative at companies. He sought out brands he used in his daily life. He estimated that he sent 20 to 30 messages per day. His unique pitch to them was that he would not only represent a brand as a college athlete but that he would create engaging videos in exchange for free products.

“It was a lot of trial and error,” Astorino said. “I probably was just pumping out emails for the first couple months to see what hit.”

He said the first company to say yes was Air Relax, which sent him about $800 worth of product in compression boots for athlete recovery. He subsequently partnered with the cold-pressed juice brand Suja Organic, along with House Pickleball, Clean Energy and Spacemilk, a vegan protein brand whose founder was so impressed with Astorino that he hired him part-time to oversee social media strategy, influencer marketing and brand collaborations.

Astorino’s ambition wasn’t so much about money as it was to network and learn about the opportunities NIL can present. He estimates he has made roughly $1,000 with the rest coming in free product. His experiences in two years have allowed him to participate in NIL from three perspectives: athlete, agent and brand representative.

Astorino thinks about ways to push something forward. He went to his local grocery store and convinced the owners to sell Spacemilk. When he was initially told the store didn’t have room on the shelves, he spent $75 to create a pop-up display with a big cardboard cutout that he set up at the end of a shelf.

“I’ve hired really expensive people, and you’ve got to hold their hand the whole way,” Spacemilk founder Walter Ross said. “And I wouldn’t hear from Michael for a week, and I’d check back in, and he’s crushed a mountain of deliverables and really pushed the ball down the field. And I’m like, ‘Dude, what? This is like some founder-level commitment that you’re just chasing after this and going for it.’”

Astorino’s foray into co-founding an NIL agency was the result of another cold outreach. His friend’s cousin is Nick O’Shea, a former kicker at Morgan State. O’Shea was thinking of starting Xtra Point Solutions when Astorino messaged him in February 2023 asking if he could be represented in exchange for designing graphics for the website and Instagram account. O’Shea wasn’t looking for a Division III athlete at the time, but he quickly realized Astorino had a legitimate interest in helping the business succeed.

“At first, I just wanted to help him feel included,” O’Shea said. “But then he started providing more value than I was providing in a lot of ways. It turned into me begging him to get on the calls with me.

“He does everything. Seriously, any meeting I go into, Michael’s there with me, whether it’s with the founder of another company, whether it’s with an athlete that we’re trying to recruit, whether it’s an athlete coming to us. Every single conversation. Even to the point where when we write for grants, we do it together. I tell everybody Michael came on as my digital wizard and turned into a wizard in every other aspect, too.”

O’Shea said neither of them has brought in much money because the initial attempt was to find free product for athletes so the two could establish their names. They have helped find deals for more than 80 athletes.

The two partnered to earn a $25,000 grant from the United Way Foundation to conduct the Payton Harvey Cheer Camp in Detroit. Harvey is a former cheerleader at Michigan. Astorino set up registration platforms for the event through the agency’s website and managed T-shirt orders.

O’Shea, a Michigan native, has used relationships from his home state as the backbone for athlete partnerships. But Astorino has been integral in helping to secure athletes, including USC women’s basketball player and former McDonald’s All-American Aaliyah Gayles. Astorino attended IMG Academy in Bradenton, Fla., for three years of high school, captained and played on the “Varsity Blue” team below the national squad and had the trust of some of his friends to help start their NIL journeys.

“The best part about NIL for us was it’s so new that nobody could tell us that they were an expert and had so many years in the business because no one did,” Astorino said.

Wesleyan hosts Delaware Valley in the Division III NCAA Tournament on Friday night. (Courtesy of Wesleyan Athletics)

Wesleyan is a small liberal arts school that is among the most academically minded Division III programs in the country. U.S. News & World Report ranked Wesleyan in the top 15 for best national liberal arts colleges. Astorino is majoring in psychology because he said the school doesn’t have a business major. Both his parents were psychologists, and his older sister, Eden, will start graduate school in September in a doctoral psychology program. His dad, David, said the family has encouraged Michael’s creativity.

“The only rules we have are you have to be a good person, and you have to find something that gives you energy and try to be the best you can at it,” David said. “Our kids are starting at a very good place in society and life. So in some cases, we just want to raise the bar higher for them.”

Astorino said his classes this semester are on Mondays and Wednesdays, which gives him time to balance everything else: workouts in the afternoon, practices in the evening, homework and his business endeavors. He is typically up by 8 a.m. and asleep by midnight. What takes up most of his time these days is the class he co-teaches as part of a for-credit student forum. His co-instructor, Ben Carbeau, is a senior and Wesleyan football player who already co-owns his own hard tea company.

The idea, Astorino said, is to prepare students to understand financial literacy, legal structure and public speaking. A recent class brought a Wesleyan alum and Harvard law graduate in to discuss how to become incorporated as a business and what constitutes intellectual property. The final project will consist of students pitching their businesses to Wesleyan alumni in a Shark Tank-style event on campus.

Astorino isn’t sure what he wants his future to look like. He has an opportunity to be a production assistant for two weeks this summer in Los Angeles on the actual television show “Shark Tank” because of a relationship he struck up with the show’s director, Ken Fuchs, a 1983 Wesleyan graduate. Astorino has a standing offer for a full-time job at Spacemilk upon graduation. There is also the NIL agency.

All Astorino knows is that he loves marketing and entrepreneurship. And, for now, he’s going to squeeze everything he can out of the Wesleyan experience, on and off the court.

“I love having packed days when my Google calendar is booked end to end,” Astorino said. “I find it’s fun for me. It doesn’t feel like work. And some days it gets super busy and overwhelming. But I love it. If there’s any time to do that, it’s now in college when you’re young and have the energy.”

(Top photo: Courtesy of Wesleyan Athletics)