From First-Gen to Full Ride: How Youssef Hacked His Way to UChicago

Youssef's approach was bold, but grounded in research.

He made sure to communicate through various metrics they might track, and in his Why UChicago essay. For his other essays, he made sure to communicate his personal values and skills through storytelling. For UChicago's supplemental prompt, he picked one that let him rewrite history. He was able to showcase his admiration for an underdog story, his passion for giving voice to silenced histories, and his ability to use humor to disguise empowerment as entertainment.

His main essay was even more unexpected, but that’s exactly what grabs an admissions team’s attention when sifting through thousands of applicants when they’re unable to set one apart. Once again he was able to use humor to engage the reader, while communicating his bold and creative nature. By stepping outside his comfort zone, he proves to a university he’s willing to take risks and be outside the box to chase his goals.

Even with all his planning, Youssef’s path to UChicago didn’t unfold exactly how he imagined.

When Match Day arrived, he braced himself for disappointment.

Youssef’s relief quickly turned into reflection.

But acceptance didn’t mean the end of his strategy and research, it was the start of a new phase.

Youssef kept looking for leverage, not simply for more, but for fairness.

🎓 Scholarship Founder & Creator – Built Youssef University to make admissions advice accessible for first-gen students. @youssefuniversity 🎤 Speaker & Storyteller – From TikTok panels to Adweek keynotes, he uses storytelling to demystify college access. 🤝 Creative Partner – Collaborates with brands to build scholarships and amplify diverse student voices.

💡 The Wildcard Wildcards don’t follow the script, they rewrite it. They bring energy, humor, and originality that admissions teams remember long after reading their essays. For Youssef, standing out wasn’t strategy, it was instinct and genuine to him. “I was the first male cheerleader that ever touched my high school's team… it won me so many scholarships, got me on the news twice, two awards — just for doing something uncharted that other people wouldn’t do.” His unpredictability wasn’t about shock value, it was authenticity. By being himself unapologetically, he showed schools he could make any campus more interesting, and wasn't afraid to contribute something new entirely. 🦄 The Unicorn Unicorns make impact before the diploma. They turn ideas into movements, brands, or communities that live beyond their own story. Youssef built Youssef University, created six scholarships with national partners, and took the stage at Adweek before graduation. “I feel like it was a fluke. I was a a pandemic creator, and it was just a random video during quarantine. A snippet of it was "I got a full ride to Chicago," and 100% of the comments were all, "Wait, wait, tell me more. What do you mean by this?" And what I like to say is, to this day, people have questions, and thank God I still have the answers.” His journey proves that success isn’t about waiting for opportunity; the students universities want create their own, then bring everyone else along for the ride.

Want to talk to Youssef? You can message him directly using Scholarly’s messaging feature! If you’re not sure where to start, here are a few questions that can get you started: 🎯 Application Strategy What kind of questions did you email to admissions reps that weren’t Google-able? If you could redo the QuestBridge process, what would you do differently? How can a first-gen student start “hacking the system” without burning out? 📖 Essays & Storytelling What inspired your Ona Judge essay — and how did you balance serious and playful tones? What’s your advice for making an essay sound like you instead of what colleges expect? How do you turn a personal moment into a bigger story about identity or growth? 💸 Scholarships & Financial Aid How did you find independent scholarships outside your school? How do you organize multiple scholarship deadlines and essays? What would you say to a student who’s afraid to advocate for their financial needs? 🚀 Life After the Acceptance What’s something UChicago didn’t give you that you had to build for yourself? How did Youssef University go from a TikTok idea to a national platform? What advice would you give someone trying to turn their own story into impact? 💡 Or start simple: “Here’s what my situation looks like — how would you approach it?”

Xander Hastings: Let's start off by walking me through what your college application journey was like. Youssef Hasweh: That's a good question. I was super freaking hyper-analytical with every single part of my college app from freshman year. I joined two CBOs. Again, I was first gen, low income. The only person in my family that went to college was my sister, and she had only done a year and then had to take a leave of absence for family reasons, my dad's health reasons. And then when he passed, she didn't know if she was able to go back to school, so she was like, "I'm putting all my eggs in your basket. You really have to tap in." So I joined two CBOs—those are community-based organizations—and they worked with me to draft a super well-rounded college app where I could show my personality, show the things I'm dedicated to, but also not throw too much at the schools I was looking at. And then I kind of say this on my platform a lot: I feel like I tried to hack the system as much as I could from someone who didn't know what they were doing. I read as many case studies as I could of similar students and tried to learn what was important to schools—yield rate, retention, all those things. And essentially what I did was I tried to find the person reading my application at all the schools I was into. So UChicago was my dream school, I was into Princeton, Columbia—I found every single rep that my application was gonna go on their desk first, and I would not stop bothering them. Every single day I was emailing them questions that weren't Google-able. I was really trying to get them to know my name. And then the minute they touched foot in New York for a conference or an admissions fair, I was there, and I was first at their table, and I was like, "I've been emailing you"—face to name stuff. So I was on a first-name basis with the admissions officer at UChicago, who later would accept me and give me a job in admissions. Yeah, that was the thought process, and then I just shared a bit about it on TikTok, and the rest is history. Xander Hastings: Yeah, yeah, I think that's so smart, because it shows that you're advocating for yourself, it shows that you take initiative. You're a doer, you don't just sit around and wait for your application to go to their desk. You're gonna make the first move. Youssef Hasweh: Crazy. No, it was so annoying. I was literally so annoying. But what I like to say is every single school tracks demonstrated interest. There are schools that say they don't track demonstrated interest in their application material, so they don't consider that for admissions, but they will just naturally know if you are extremely interested or you're extremely not. At the end of the day, this college stuff is a business. All these colleges are businesses. They just want people that will 100% go if they give them the green light. Xander Hastings: Absolutely. That's the big metric for them—acceptance rate. And that's why waitlist culture has gotten so big, because they need you to prove it. Youssef Hasweh: Yeah. Almost half of my entire friend group at UChicago got off the waitlist, and they were called the day of and were like, "We're gonna give you a spot on the waitlist and accept you if you say you'll come right now." They would give them max an hour. That's insane. I know someone who accepted on the spot, and I was like, "You didn't even negotiate financial aid? What are you doing?" Xander Hastings: Yeah, so many of the scholars I've talked to too, I feel like almost half have been waitlisted. It's just what they do to make you prove, like, "Hey, is this your number one? Prove it." Youssef Hasweh: Crazy. It's a flex for other schools. I mean, I don't know why they take the US rankings so seriously. It's all just nonsense. Xander Hastings: And then what did you write your essays about? Youssef Hasweh: Oh, that's a good question. I haven't done too many videos on this. My UChicago supplement was one of my best work. I was so proud of it. I did the "choose any prompt ever," and the prompt I picked was "pick a historical figure from a different time period, put them in a different time, and what would happen?" And then I chose Ona Judge. Do you know who that is? She was George and Martha Washington's slave. Yeah, and she escaped captivity, and George and Martha—she was specifically Martha Washington's slave—they spent the equivalent of millions of dollars trying to find her, because she was their favorite. Trying to find this woman all over the continental U.S., and they couldn't find her. So I kind of framed her as the only person to beat the man that won the American Revolution, and then I threw her in the Great Depression, and I was like, "If she could do that, she could freaking cure the Great Depression." And it was fun. It was so serious in the beginning, and then I had a good time with it at the end. That was my supplement. My main essay, which I don't talk about online much—I've done a lot in person—was in high school, I tried out for the cheerleading team, and I was the first male cheerleader that ever touched my high school's team. So that was the main part of the essay. And then, fun fact, I was also on the baseball team. So I was sharing a bit about these differences—it felt like an oxymoron to be a baseball cheerleader. It was like, "Hey, I just really wanted to throw people in the air, and I really wanted to be the best shortstop that team's ever seen for one year." And then I was benched the next year. It's fine, it's fine, we're not gonna talk about it. But yeah, that was my main college essay, and then the rest of the supplements were whatever. Xander Hastings: Dude, that's so cool! I really feel like your personal narrative, the cheerleading one, fits so well into the wild card archetype. It's unexpected, it's so fun. You want those kinds of people to bring life to campus. You're not afraid to try new things, not afraid to put yourself out there. Youssef Hasweh: For real. All of my friends in high school clowned me so hard. And I was like, "Well, one, I'm on this team with all these girls," and then it won me so many scholarships. I used that one personal statement for so many scholarships, it got me on the news twice, I got two different awards for it—just for doing something that's uncharted territory, that other people wouldn't do. Not really giving a heck. Xander Hastings: Yeah, that's dope. It truly demonstrates so many of the qualities that schools look for in their students. Very much like a pioneer. How did you get started with Youssef University? Youssef Hasweh: Oh, that's a good question. I mean, Youssef University literally, I feel like it was a fluke. I was a COVID creator, a pandemic creator, and it was just a random video during quarantine. A snippet of it was "I got a full ride to Chicago," and 100% of the comments were all, "Wait, wait, tell me more. What do you mean by this?" And what I like to say is, to this day, people have questions, and thank God I still have the answers. And that's why—the only reason why I think I'm still kind of relevant in this space—is because I feel like I'm still providing value to new generations of students, advice that they haven't heard before. And I just kept blowing up, and then brands reached out, and I made scholarships with them. I've made six scholarships in my name through other brands, which is really cool—to give back money and stuff. And then so many random things. I've worked with so many brands, so many different brand deals, activations, things like that. I worked on TikTok's diversity collective—they only picked 12 creators at the time for that for the entire year. And then BuzzFeed reached out, and I was a part of their meta residency. So it was just—again, it's brought me to places I just never would expect, and I've met so many cool, weird people. Finals week of third year, I missed two finals because TikTok flew me out to speak at Adweek. I was the keynote speaker of day one, and I was like, "I'm not missing this, no way, no way." And then I ended up making them up, it was fine. Xander Hastings: That's so cool. I think truly, you're never gonna lose relevance and value, like you were saying, because at the end of the day, college apps is storytelling, and you're just a fantastic storyteller, and that's all that matters. Youssef Hasweh: That's the biggest compliment you can give anyone. Xander Hastings: Well, that's what jazzes me up about doing Scholarly and all this stuff—I love hearing stories, and I love seeing people's colors. I'm like, "Man, I want to go apply to college again" when I hear a cool essay like yours, or I read someone's essay. I feel like I would do it so differently now or try it so many different ways. Xander Hastings: Were there any challenges you faced during the application process? Youssef Hasweh: Oh, so many different challenges. I'm trying to think about Youssef's mindset in high school. There were a bunch of challenges. I mean, I did the QuestBridge process, so—I mean, it's kind of how I built my platform. I got in with sort of a guaranteed full ride, and I applied through QuestBridge, and that was a challenge in itself, not even just because of the selective nature of the scholarship on top of the selective nature of the schools' different admissions rates, but I actually had regretted applying through QuestBridge and doing the ranking system, because I thought I had a better chance, and I would get a comparable financial aid package if I had applied and taken the time to develop my app for early decision in November. Because QuestBridge was due in September so I thought I actually joined way too prematurely. I thought I had ruined my shot. I'd spent all this time developing relationships with admissions counselors, and really diving deep into case studies of—again, we didn't have TikTok. The best advice I give students is, if you really want to know a school, search up "day in the life, [blank] school," and find out what the students are saying, or join their Reddits, their subreddits. We didn't really have that, so I was just leaning on what I could find, and I just felt like I shot myself in the foot by trying to be over-prepared. I somehow was underprepared, and again, that's the imposter syndrome a first-gen student is gonna face. And I got ready to find out which school I had matched to, and in my head, I was like, "It's definitely not UChicago." That was my first thought. I saw a match, and it doesn't show the school yet, and I was like, "It's not UChicago." And then I was surprised. I was so shocked. Yeah, but I think the biggest challenge was—there was just a lot to navigate. There was just no one to hold your hand through the process. You can have as much support as you want, and honestly, I think less support is more sometimes. There shouldn't be too many cooks in the kitchen. But yeah, it's not even just applying to college. You are trying to apply to a selective elite group of people, and it's so daunting. It's not just applying to college, it's a lot more than that. This generationally has already changed my life. Yeah, and there's just a lot riding on it. Xander Hastings: No, absolutely. I mean, that's everything that I believe in. It does make the difference generationally in your life, and it's something that if you're applying blind or applying alone, and you don't have someone who's gone through that process—even just knowing, "Oh, my brother went here, or my cousin went here, and I can reach out and talk to them"—makes all the difference because it's not as daunting and scary. But if you're just applying alone in the dark, first time, it's just... yeah, I completely agree. I think that it's so important that everyone should have access to that. And while there is r/ApplyingToCollege now, it's kind of a toxic environment, and so doing that in a way where it's healthy, supportive, creative... Youssef Hasweh: Yeah, the comments are bad. Everyone's freaking tearing people up. No, it's a mess. I felt like we didn't have as many resources as we should have had, and almost now there are too many, to the point where some of them have become toxic, and then there are still gaps missing, which is so weird. Everyone's doing the same thing, everyone's doing the same exact model. And it's like, you would think this abundance of people having eyes on this thing would mean more gaps being filled, but I feel like it's still the same. So weird. College admissions is so weird. Xander Hastings: I know, yeah. But I think if we all work together towards a better system, then I think—because ultimately, I'm not the guy to change things. I want the community to change things. I want people to work together, and that's what changes things, you know? Youssef Hasweh: Heck yeah. Xander Hastings: If you could go back and give yourself any advice, if you were doing the process over again. Youssef Hasweh: Oh, man. That's a good question. I wish... I would tell myself to vlog the whole thing. I would tell myself to start on YouTube, not TikTok. No, I think I would genuinely tell myself to calm down. Not only did it all work out—every single thing happened for a reason, and I didn't have to be in a million clubs and do a million things so that people knew I had density, I had layers. Also—this might be a little too recency biased, but I just—I wish someone sat me down and was like, "Okay, UChicago can be your dream school, but you should not put any school on a pedestal, at least the type of pedestal I was putting UChicago on in high school." It was as if this school could do no wrong. I would literally tell myself, "Don't—you can like UChicago, but don't have a dream school. That's crazy." I realized pretty fast that I wasn't actually interested in what UChicago was giving me besides my platform and then all the other opportunities. God and myself made those from it. UChicago wasn't handing me things. Xander Hastings: I think that's really real advice. Like, I was similarly disillusioned, because it was my everything, too. Don't put anything on a pedestal. I think that's fantastic advice. I would give that to myself, too. Youssef Hasweh: Oh, because I mean, especially us two, I feel like we took the untraditional UChicago route, 100%. We used it to kind of find our own path. Xander Hastings: 100%. And then any—I'll let you, for the last bit, just anything that you'd like to tell the high school students. Youssef Hasweh: Okay. Yes. Love college. Love college admissions. Apply to scholarships. Apply to scholarships. I won over 30 scholarships, over a million in scholarships that were not school scholarship-based, so I'm not counting anything that's financial aid from the schools that I was accepted to. These were true scholarship programs. I applied to so many and won so much that I was getting well over 20K a year directly to me from scholarships. And renegotiate your financial aid packages. Again, this is a business. You need to play it like a business. Don't put these schools on a pedestal. Renegotiate your aid. Advocate for yourself and your communities and whatever identities you hold. And then just have a ball with the rest of it. And that's the true college experience, that's the true college dream. Yeah, my dream school is Youssef University. That's it.