High School Student
Trying to understand how cities (especially Chicago), people, and technology fit together — and building small programs to help them work better.
Hi, I’m Leo, a high school junior, lifelong Chicagoan (at least in spirit), and someone still figuring out how my interests in urban planning, AI, and business all connect. I’m exploring the spaces where people, ideas, and next-generation technology come together to solve problems that make cities stronger.
I know the L lines better than most commuters, and let’s be honest, deep dish, (specifically Lou Malnati’s butter crust) is far superior to New York-style pizza. It’s not even close. I’m a loyal fan of the Bears, Bulls, and Cubs (which builds character), and I still root for LeBron James even if that confuses a few Chicagoans.
When I’m not studying or working on my personal projects, Chicago Rising and AI for Main Street (neither are school clubs, just projects I felt were well worth my time), you’ll probably find me playing club basketball (I’m not serious enough for the school team, but I love the game), using my Six Flags Great America season pass, or trying to save money to get to other amusement parks (Universal in Florida tops my list). My friends and I love exploring new corners of Chicago whenever we can.
I have a black belt in Taekwondo, though I don’t usually mention it because it’s not about bragging rights. It’s taught me self-discipline and focus, which have helped in almost everything else I do. For as long as I can remember, my teachers have told me they wish I’d speak up more in class, and they’re right. I’m more of a listener than a talker. That’s something I’m working on, but working hard and leading quietly just feels more natural to me.
You might wonder why I’m into cities. Simple, they’re amazing and messy at the same time. Cities create most of the world’s energy and innovation, but they also face real problems: inequality, safety, and huge gaps in opportunity (for example, in some areas, people live decades less than others just a zip code or two away). I think that mix makes them the most interesting places to study and improve.
As for what’s next, I’m exploring, but right now I’m leaning toward studying business while continuing to explore how my interests in urban planning and AI, when used as tools by people who care, can help make Chicago stronger and help local institutions solve long-time problems and grow. I don’t know exactly where that path leads yet, but I’m curious, motivated, and ready to continue exploring as I figure it out.
I’m pursuing college-level humanities, economics, and research coursework to support my urban solutions and AI projects
GPA 5.273 / 5.0
As an AP Capstone candidate, I’m completing a two-year research sequence focused on independent inquiry and cross-curricular research. The program culminates in an original thesis and a specialized diploma recognized for academic excellence.
In Process
These courses help me understand real-world operations, financial systems, and community institutions — all of which shaped my AI for Main Street project.
Total Goal: 100 Hours
At 16, I figured my world-changing powers were limited. But I did know history and every Chicago “L” line. That turned out to be enough to help immigrants in Chicago study for their U.S. citizenship exam
Chicago students and teachers are entering an AI-driven world, and now is the moment to make the city a national leader in preparing them.
Why are we treating AI as academic dishonesty in schools when it is actually a career requirement? And why are we hesitating to encourage students to master the tools that will transform them from entry-level hires into six-figure professionals? Technological change has a long history of being misunderstood. Early skepticism often gives way to widespread adoption, and those who adapt first tend to benefit most. Consider the past: The internet was dismissed as incapable of replacing paper newspapers, personal computers were seen as unnecessary in the home. Even the automobile was once called a passing fad. Closer to home, many believed machine learning and electronic platforms would never replace the trading floors of the Chicago exchanges. These were not fringe opinions. They were widely held beliefs.
We have been here before. The risk for schools is not that artificial intelligence moves too fast. It is that we respond too slowly. Treating AI as a threat rather than a tool is not caution. It is surrender.
We are told AI will define our future, yet in classrooms today, using it is often treated as academic dishonesty with consequences. You cannot prepare our generation for a fire drill by telling us we are not allowed to use water.
The consequences of this “confidently wrong” approach are already here. At Hingham High School in Massachusetts, a high-achieving student used AI for research and outlining on a history project, something many teachers encourage. The student was punished with failing grades on key sections, a drop in GPA, Saturday detention, and initial denial of National Honor Society eligibility.
In Maryland’s Broadneck High School, a student received a ‘zero’ for her grade and an academic integrity violation after GPTZero flagged her essay. After public embarrassment, the accusation was later investigated, proven false, and fully rescinded. Across the country, some students deal with false accusations, months-long investigations, or disqualified essays, as reported by ABC News and The Washington Post. There are plenty of students using AI in ways that are not appropriate, but it seems that the burden has flipped: students must now prove they didn’t cheat just to be allowed to learn.
Even in Chicago Public Schools, the plan for AI is unclear and sends a confusing message. CPS has not banned AI. Its district-wide guidebook encourages AI for idea generation and for learning. It requires student disclosure, while permitting teacher use of detection tools that the district admits can produce false positives.
CPS has created rules for AI use. It has not created a plan for AI success.
This creates a “gotcha” culture that punishes the curious and rewards the cautious.
The district has started the conversation, but it needs to finish the job. CPS needs a systemwide curriculum, a defined funding stream, and an executable plan to make sure that every student and teacher will benefit. Time is not on the students’ side.
Our future as students is shifting quickly. McKinsey reports 51 percent of organizations are already reducing entry-level hiring because of AI. Goldman Sachs estimates 300 million jobs globally exposed to disruption. The World Economic Forum notes 41 percent of employers plan workforce reductions as automation expands.
Schools cannot prepare students for 21st century careers by failing to train them in 21st century technology.
The good news is there are models that are working. At Seckinger High School in Georgia, AI is fully integrated into the curriculum. Students build models, analyze data, and study AI ethics every day.
In Newark and Niagara Falls, public school students complete Stanford University-designed programs where they learn prompt engineering and are required to earn certifications before graduation. They receive grades for their AI work, just like in other classes. Illinois districts like Indian Prairie are integrating these tools starting in third grade.
These models do not promote cheating or taking the easy way out with AI. In fact, just the opposite. They elevate work and prepare students to be productive members in the workforce of tomorrow. That is hardly cheating.
Chicago has a choice: Remain reactive, or lead.
Roughly three-quarters of Chicago students are not meeting proficiency benchmarks in math and nearly 60 percent are falling short in reading. The district is failing these students.
Intentional AI programming can help address this. Stanford University research shows structured AI tutoring can improve math performance, with gains of roughly nine percent. The Brookings Institution reports meaningful improvements in math and ELA learning when AI is implemented with clear structure and guidance.
Unstructured use may increase engagement, but not outcomes. The difference is not the technology. It is how it is used.
Chicago has a choice to prepare its students and lead. Here are four focused steps CPS can take to enact swift change.
First, establish a dedicated AI Integration Office within CPS.
This team should have a clear mission: Improve student outcomes, increase teacher productivity, and position Chicago as the nation’s leading big-city school system for AI training. Without ownership, strategy becomes suggestion. A centralized team ensures consistent implementation and accountability across schools. Beyond academic gains, AI has proven to be a reliable cost saver when implemented properly, and the CPS administrative budget will be no exception.
Second, build a clear systemwide AI curriculum with a “proof of work” standard.
Make expectations explicit. Require students to show prompts used, errors identified, improvements made, and their own reasoning. Teach AI ethics so students understand not just what is allowed, but why.
Third, invest in practical, teacher-first training.
Provide hands-on use cases, shared lesson plans, and clear grading standards. AI can free teachers from repetitive tasks so they can focus on mentorship, relationships, and early intervention. This strengthens both instruction and the profession.
Fourth, build a competitive AI ecosystem across CPS.
Partner with national programs like aiEDU and TeachAI and create citywide competitions such as AI Olympiads and hackathons. Work with Chicago’s robust private sector to offer scholarships and real incentives for student participation.
These steps reinforce what already works: quality curriculum, data-driven growth, early intervention, professional development, and time on task. AI does not replace these fundamentals. It accelerates them.
AI could be the great career disruptor, but if we find healthy ways to be early adopters in our schools, it can be the great accelerator for students, teachers, and the city of Chicago.
Now is the time to trade caution for courage. By thoughtfully integrating AI into our curriculum today, we stop reacting to the future and start clearing a high-speed lane for every student in this city.
The door is wide open. It’s time for Chicago to walk through it — our students are counting on it.
About the Author:
Leo Fiascone was born in Chicago. Now a high school junior, he is the founder of Chicago Rising, an independent research project focused on data-driven solutions to the “kitchen table” issues facing Chicagoans. His work also includes AI for Main Street, an initiative exploring how ethical, practical AI can support small businesses. For more on his research into urban policy, ethical AI, and economic opportunity, visit www.leofiascone.com.
The Quiet Exodus: Why Chicago’s Middle-Class Families Are Leaving
By Leo Fiascone
April 2026
Chicago is a world-class city built for 3.6 million people. Today it has just 2.71 million and is watching its middle class deteriorate in real time. In this published piece, I lay out why families are leaving: public schools that cost $30,000 per pupil yet deliver unnacceptable results, and streets far more dangerous than the collar counties surrounding us. No sugarcoating. Just the data and a direct challenge to 2027 mayoral candidates to actually fix it.
Who will answer the call to stop the exodus from Chicago?
In 1871, Chicago rebounded from a fire that destroyed nearly one-third of the city to become the fastest-growing city in the world by 1930. By the 1950s, Chicago had built up an infrastructure to accommodate its 3.6 million people, including dozens of distinct neighborhoods, schools for hundreds of thousands of children, and a tax base built to provide services for a thriving middle class. That framework remains, but today Chicago can be described as a giant wearing clothes that don’t fit anymore. With the population down to 2.71 million residents — U.S. Census estimates for 2024 to 2025, holding steady into 2026 projections — Chicago’s population has dropped nearly one million residents from a high in 1950, which has made it a struggle to function efficiently and appealing for middle-class families to remain.
The demise of the middle class
The Windy City’s engine has stalled. Chicago has sunk to population levels from the 1920s, with public transportation lines running under capacity while costs to operate increase. School buildings, built to accommodate hundreds, remain open to educate fewer than two dozen, with costs per-pupil as the tax base shrinks without commensurate cuts in overhead. While Chicago leads in corporate relocations — Chicagoland was No. 1 for the 13th straight year in 2025 with over 600 projects, Site Selection Magazine — downtown office vacancy hit a record 28.2 percent at the end of 2025 — CBRE data via Crain’s Chicago Business — with some buildings facing 90 percent markdowns in sales prices and a dwindling commercial property tax base is causing fiscal chaos.
Most critically, Chicago is losing its middle-class. In 1970, half of Chicago was middle-income; today, just 16 percent remain according to UIC and WBEZ census-tract analysis. In the last decade, Chicago lost approximately 85,000 Black middle-class residents. A shrinking middle class also hurts remaining low-income residents by reducing local jobs and tax revenue for essential services. Shockingly, no comprehensive city-sponsored plan addresses this mass exodus.
Families are leaving CPS
Families aren’t just leaving Chicago; they are leaving Chicago Public Schools, and Chicagoans are paying the price. Nearly 55 percent of Chicago’s residential and commercial property taxes fund a system with a $10.25 billion budget for 2026, which equates to roughly $30,000 per pupil (CPS adopted budget documents).
Chicagoans are paying premium prices — equivalent to top-end private-school rates — for highly underperforming student performance. According to the 2025 Illinois Report Card, only 40.6 percent of students were proficient in English/Language Arts (ELA) and 26.2 percent in math, so it is not surprising that enrollment has plummeted by 110,000 students since 2000, a 25 percent decline.
Public safety: A staggering disparity
In 2025, Chicago recorded 416 homicides, which was the lowest since 1965. While this is progress worth praising, the disparity with Chicago’s immediate neighbors is staggering. The population of the five collar counties — DuPage, Lake, Will, Kane, and McHenry — have a population surpassing Chicago’s by 500,000 but suffered only 57 homicides collectively.
With a significantly smaller population than its collar counties, Chicago had seven times more murders (416 vs. 57) and 10 times more shooting victims than those five counties combined (1,847 vs. 180). Even worse: Over 250 Chicago school-age children —17 and under — were shot in 2025. In the collar counties, that number of school-age children lingered in single digits. Parents weigh these risks every day, and those with options choose to leave.
Facing the counter arguments
Critics will say: “Crime is down!” and “Corporations keep coming!” That is true, and we should be energized over this news. However, others argue the suburbs boomed because the 1950s federal highway expansion enhanced commuting options. This is also true; people want Chicago’s energy, just not enough for many to absorb the city’s risks and costs. The points critics make do not defend the status quo; they expose a broken system with certain components requiring immediate attention.
Proximity to Chicago is simply not the same as living in it. When families flee to safer, more affordable communities with superior public schools, Chicago suffers. Campaign slogans, pretending these problems don’t exist, and serving up excuses for why they don’t get fixed, are not plans to revive Chicago.
A roadmap for 2027: A call to action
To the 2027 mayoral candidates just getting early attention on the race: Chicago’s future depends on more than recycled promises that fail to deliver. Chicago deserves a specific vision and a ruthless pursuit of the elements that rebuild the middle class and families with kids. As a starting point, Chicagoans deserve a granular roadmap with 36-month milestones for three initial pillars; specificity is what voters want, so consider it your friend. For example, a year-one goal could include returning Chicago Police to 100 percent beat-patrol staffing in high-crime districts. Show us what your plans look like for schools, safety, and growth.
Educational choice: Today, Chicago spends $30,000 per pupil, yet the proficiency rates are abysmal., To counter this, the city must provide a broad range of options for students enrolled in its failing schools. This is not an extreme position; school choice is already welcomed in 18 states. In Chicago, the high demand for the limited selective enrollment and charter seats demonstrates parents desire more options, not less. States such as Florida, where school choice flourishes, has shown proficiency rates improve significantly without increasing the state’s education budget.
Safer streets: Utilize data-driven and focused strategies that specifically target repeat offenders. This method has proven effective in New York, Los Angeles, and dozens of other cities around the country by using data analytics to target the groups of known repeat criminals who cause a disproportionate amount of violent crime in the city. This strategy has driven dramatic drops in violence in New York and Los Angeles. Chicago is actually home to some of the world’s best data science minds, including firms like Benchmark Analytics. If departments nationwide use Chicago-based technology to reduce risk, why isn’t Chicago leading that charge?
Fiscal growth: Grow the city and the tax base, not just tax rates, to make Chicago affordable for middle-class families. Leadership must work with the business community and local developers. Bring more people back to offices, restaurants, Michigan Avenue, and hotels. Increase crane count by making new development more expedited and encouraged, and drive development as the real path to growth.
An effective mayor and administration must lead on these issues to get the city “open for business.” By attracting conventions, tourism, and jobs that generate sales tax and hotel revenue, the city can reduce reliance on property taxes, fees, and fines that hit residents who can least afford them.
Escalating property taxes, red-light and parking tickets, and fees are currently hammering lower-income families. Alleviating this regressive taxation requires a strong sense of urgency. They don’t need escalating taxes; they need escalating support and investment in their communities.
Let’s rebuild the city designed for 3.6 million, starting with the middle-class families who deserve reasons to stay. Chicago deserves leadership with specific plans and the determination to execute with conviction, not campaign slogans and catchy commercials. Chicago deserves a future we can all believe in.
Leo Fiascone was born in Chicago. Now a high school junior, he is the founder of Chicago Rising, an independent research project that has spent two years analyzing data-driven solutions for the “kitchen table” issues facing Chicagoans. For more on his research into urban policy, ethical AI, and small business support, visit www.leofiascone.com.
My 160,000-Mile Confession: Why an Old Ford Flex Means More Than Any Luxury SUV
By Leo Fiascone
April 2026
The most honest thing I own is a 2013 Ford Flex with 160,000 miles on the odometer and a dashboard cracked by Chicago winters. Parked beside new Broncos and Wranglers at Hinsdale Central, it quietly testifies to my family’s core rule: use things fully, protect what matters, and build for the long term.
The most honest thing I own is a 2013 Ford Flex with 160,000 miles on the odometer and a dashboard cracked by years of Chicago winters. I share it with my family, and in the parking lot of Hinsdale Central, where sixteen-year-olds often arrive in new Broncos and Wranglers, it is an outlier. So is my dad’s 2005 Chevy Suburban.
For a car old enough to drink alcohol and another with enough miles to circle the earth over six times, these cars are a rolling testament to my family’s logic: use things fully, and save for what actually matters.
That philosophy was forged in 2022, after a mass shooting just steps from my school and another near my four-year-old sister’s preschool pickup line. My parents called me into their bedroom and told me we were leaving Chicago. I was angry; it felt like surrender. But beneath the frustration, it was also discipline, the same logic that keeps a 160,000-mile car running: protect what matters, and plan long term.
I’ve always been a quiet builder. Suburban comfort does not define me; I am a city kid shaped by leaving. I experienced the “middle-class exodus” not as a statistic, but as a forced pivot that tested my family’s values. My parents’ model of stewardship, living beneath our means to invest in what lasts, became my own.
So my academic “receipts” weren’t bought; they were built. While peers pursued curated programs, I used a Coursera subscription and a couple hundred hours of my own time to self-teach Artificial Intelligence through UPenn and Urban Planning through Johns Hopkins. I wasn’t chasing credentials. I was trying to understand the structural failures that push families out of cities like mine.
I applied those tools at Erie Neighborhood House. Using $400 of my own savings, supplemented by $1,100 in grassroots $50 contributions, I helped architect a bilingual digital tutoring platform to replace 200-page binders for families whose schedules don’t fit institutional assumptions. But building remotely wasn’t enough. On weekends, I drove that 160,000-mile Flex back into the city, conducting field research for my Chicago Rising project and working with the Chicago Metropolitan Agency for Planning to connect policy to lived reality.
Limited resources have become a competitive advantage. They demand precision, accountability, and ethics. I’ve carried that mindset into cold-pitching community banks for my AI for Main Street initiative, where I analyze real underwriting and compliance workflows to identify low-cost AI solutions that can expand access to credit without increasing default risk. Most recently, a semester invitation at Goldman Sachs showed me how finance can either widen or narrow the gap for small businesses and middle-class families. Watching analysts run models that penalized neighborhoods based on zip code rather than individual merit made the stakes feel personal. I realized I didn’t just want to understand these systems. I wanted to help redesign them.
I am looking for programs that combine the business skills needed to support small businesses with the urban planning knowledge to strengthen cities like Chicago. I want to move from analysis to execution, building systems that make cities viable for middle-class families again.
I am not a product of elite privilege. I am a product of disciplined stewardship, unconditional love, and a 2005 Suburban and 2013 Ford Flex that still run because we take care of them. That same mindset will shape how I show up in college: building thoughtfully, questioning systems that leave families behind, and staying grounded in the realities those systems affect.
Because in the end, the goal isn’t just to keep an old car running. It’s to help rebuild systems that were designed to last and make sure they still do.
The Straw That Broke the Camel’s Back
By Leo Fiascone
April 2026
It took two shooting incidents and one dark night in my parents’ bedroom to turn me from a seventh grader into a mission-driven Chicagoan. This is the story of why I left, and the blueprint I am building to ensure other families can stay.
In 2022, the neighborhood around Holy Name Cathedral stopped feeling like a sanctuary. I was thirteen years old when, on Thursday, May 19, 2022, nine people were shot, two killed, and seven wounded just steps from my school. Shockingly, that wasn’t the only incident that hit too close to home. Several months prior, on Tuesday, October 26, 2021, a shooting occurred in the pickup line of my four-year-old sister’s therapeutic preschool. While she was not physically caught in the crossfire, the reality was undeniable. The places that were supposed to be the safest for a seventh grader and an autistic toddler had become crime scenes.
The end of my life in the city came on a dark night in my parents’ bedroom. They called me in to tell me we were leaving. I was pissed off and I frankly still am. I felt like we were surrendering, but deep down, I understood the logic. My parents were making the same choice thousands of other families were making. I was becoming a data point in the mass departure of Chicago’s middle class.
Moving to the suburbs felt like being sidelined. While my peers joined school clubs that meet once a week for window dressing, I spent hundreds of hours on my self-initiated project, Chicago Rising trying to understand the data of our troubles. I wanted to know why a city I loved with all my heart was failing to keep families like mine safe.
Over the last two years, I have done a deep-dive of city issues. I researched topics like why Chicagoans in some zip codes live to an average of 90 years old, while just three zip codes away, others live to only 60. I studied the staggering decline of Chicago’s middle class, which has plummeted from 50 percent of the city to just 16 percent today. I wanted to know why Chicago Public Schools lost 25 percent of its student population, or 110,000 kids, while the budget ballooned to over 10 billion dollars. I studied why the city of Chicago and its 2.7 million residents had a murder rate 7 times higher than its adjacent collar counties, which have a larger population of 3.2 million. I wanted to understand why my neighborhood was no longer a place where my parents felt safe to raise their kids.
Because my high school did not offer any classes on these issues, I went outside the building to find answers. I took Urban Studies courses designed by Johns Hopkins and joined the CMAP Future Leaders summer program to study how cities actually function. I did not want to be a bystander; I wanted to be a problem solver.
I do not see AI as a career, but as a high-powered toolkit to advance my projects. To master these tools, I have taken over 150 hours of specialty AI training through University of Pennsylvania courses and other advanced programs. AI is the engine I used to help architect and implement a cutting-edge digital AI tutoring platform for Erie Neighborhood House. I spent over 150 hours on my efforts with the Erie House. I raised $1500 ($400 from my savings and $1100 from 22 solicited donors at $50 a piece) to replace 200-page paper binders with a bilingual system that respects immigrants’ grueling work schedules. AI for Main Street, my self-initiated program to help community businesses integrate ethical AI tools will take over 240 hours of my time. This includes partnering with a local community bank to fix the biased algorithms that flag a 30-year Southwest Side grocer as high risk just because of his zip code.
My work is not about resume padding and, admittedly, it is not the typical suburban high school path. It is a direct response to that Thursday in 2022. While I do not have all the answers, I know my path. I will use my interest in urban planning, my love for small business, and the powerful tools that AI brings to continue my mission. I am training to be the type of leader who does not just watch the middle class depart but builds the systems that make them want to stay.
Zip Codes Should Not Be Death Sentences
By Leo Fiascone
March 2026
Two Chicago neighborhoods. Nine miles apart. One lives thirty years longer than the other. Systems created that gap. Understanding them matters and fixing them needs to be the focus.
The water taxi cut through the Chicago River that muggy July afternoon, the skyline sharp against a blue so bright it almost hurt to look at. Everyone clenched cell phones in their hands taking video of the bridges and gleaming towers. I kept staring at the shoreline, the question burning: How can a few miles of concrete and water create a gap where people in one neighborhood live decades longer than those in another? Streeterville residents reach 90 on average; Englewood, just nine miles south, hovers around 60, matching life expectancy in some developing nations. A 30 year difference. Your ZIP code should not decide how long you get to live.
For the first time, at age 15, inequity stopped being a statistic I could cite and became a responsibility I could not ignore.
That statistic had been floating around reports for years, but riding the water taxi during the Future Leaders in Planning program made it visceral. We had just toured Pullman, where history and planning collide in brick and rust, and studied stormwater models that showed how one small design tweak, a raised curb or redirected drain, could shield an entire block from flooding. I felt the urgency then. Cities are not abstract systems; they are people’s daily lives, and small, thoughtful interventions can shift outcomes dramatically.
I could not unsee it. So I started Chicago Rising, my self directed research initiative. No waiting for permission or a fancy title. I explored dozens of topics and ultimately chose seven kitchen table issues that I felt we had the power to improve locally, unsafe public transit, lead in drinking water, universal Pre K, recidivism, neighborhood commons, a City Charter, affordable housing, and researched replicable solutions from cities here and abroad. I cold emailed nonprofit directors and civic leaders, transcribed hours of interviews, and drafted pragmatic proposals grounded in evidence, not ideology. What began as research slowly became conviction: if cities are designed by people, they can be redesigned by people too.
The work was quiet and during most of it I felt way over my head. Late nights poring over data until my eyes blurred. Realizing a minor transit redesign could cut crime at stations or that a common sense zoning reform could immediately expand garden apartments, creating thousands of lower cost housing units while generating additional income for homeowners struggling with mortgage payments. One director told me, “Most people talk at us. You actually listened.” That meant more than any accolade. It affirmed something I had quietly suspected: my instinct to listen first was not a weakness. It was my way of leading.
I am not the kid who commands attention. Teachers have gently, and repeatedly, nudged me to speak up more. They are right. I am a listener first, thinker second, doer third. In rooms where others compete to be heard, I compete to understand. Leading quietly feels natural. My black belt in Taekwondo is not for show; it is the discipline of showing up daily when no one is watching. That same steady grind powers everything, whether mapping ethical AI solutions for small businesses, tutoring at Erie Neighborhood House, or enhancing its platform to serve working immigrants who need to study on their own schedules, not ours.
There, on weekends and late evenings, I help immigrants prepare for citizenship exams, breaking down the Constitution with Chicago-centric analogies. When someone passes and realizes Chicago is finally, officially home, their face lights up with a quiet joy that stays with you. Erie Neighborhood House has shaped Chicago’s immigrant communities for 150 years, and I want its impact to endure. I am now building a mobile first platform that digitizes the curriculum into bilingual, interactive modules, reshuffling missed questions until they are mastered and freeing tutors to focus on mentorship rather than paperwork. I will put in $400 from my own savings and raise another $1100 to get this new platform running efficiently. The goal is not flashy innovation. It is dignity, access, and staying power.
This sense of urgency, to notice disparities and act locally, drives AI for Main Street too. While headlines debate AI extremes, I cold pitched a community bank with a simple offer: let me map your operations and connect you to ethical consultants for low cost tools that strengthen service without replacing human relationships. People, families, and communities first, then government, and finally the businesses that create AI. In that order. Not tech for its own sake, but innovation that protects those most at risk of being left behind.
I see college the same way, not four years of credentials, but a 45 year investment compounding over decades. I do not want proximity to prestige; I want proximity to problems. I want a campus where ideas connect to urban equity, ethical technology, and community resilience. Where quiet builders like me can contribute steadily through research teams and partnerships. I will bring frameworks that make rooms and cities work better: listening hard, thinking systemically, acting with urgency yet patience for lasting impact.
Chicago taught me the city is messy and magnificent. Deep dish debates that get heated. Six Flags adrenaline. Rooting for LeBron despite the side eye. Those quirks keep me human. But the disparities keep me moving. Zip codes should not sentence anyone to shorter lives. I am not promising to fix it all. I am promising something steadier: to keep showing up long after the headlines fade, to build systems that outlast me, and to measure success not by recognition but by resilience.
If your community values systems thinkers who feel urgency yet play the long game, who listen before speaking and build before boasting, and who are focused on the outcome for people, families, and communities, I would be honored to bring that energy to your campus. Because the problems worth solving do not wait, and neither should we.
Some People Call This Cheating
By Leo Fiascone
February 2026
Some people warned me not to share this. They said explaining my process could look like cheating or give away an advantage. I get why they said that. This essay explains why I believe ethical system design is not a shortcut, but the disciplined way I have adopted to grow, build, and compete.
In football, some plays spark debate. When the Run-Pass Option first appeared, critics called it “cheating,” arguing it gave quarterbacks an unfair advantage. As a fan, I can see the power of a system designed to read, adjust, and execute with precision. That’s how I approached college admissions. Not as a contest of self-promotion, but as a systems problem.
The first time I seriously thought about it, I didn’t feel unqualified or unprepared. I felt aware. Aware of how many students seem louder and more naturally impressive in a process where clarity matters as much as accomplishment. And aware that this process asks you to compress years of work, curiosity, and growth into a few pages that someone might spend a total of 10 minutes reviewing. If success depended on presenting myself quickly, I needed to figure out a way to put forth a concise product that reflects the hard work I have done.
Throughout high school (and even before) my teachers have always told me the same thing. They say I have strong ideas and see connections others miss. Then they add that they want me to speak up more. They are right. I tend to listen first, think things through, and talk when I believe what I have to say will actually add something. That instinct serves me well in building things, but it can be a disadvantage with high-pressure processes that reward immediacy or outward salesmanship.
So when the admissions process began to take shape, I felt intimidated, not by the work itself, but by the structure of it. Every credible advisor explains the same components. Rigorous academics. Service and values. Meaningful work outside the classroom. Letters of recommendation that reflect who you really are. Essays that somehow make you memorable to someone who will never meet you. All of it is filtered through a process where an admissions officer may spend only minutes on your file. When I looked at it that way, it stopped feeling like an evaluation and started feeling like a systems problem. That shift changed how I approached everything.
The shift became real when I started preparing materials for my teachers. Instead of asking them to summarize me broadly, I shared a structured snapshot of my work (specific projects, writing samples, and reflections) that showed how my interests had developed over time. The goal wasn’t to tell them what to include, but to make my work easier to see. That clarity will allow my teachers to write more specific letters, and it helped me organize my thoughts in ways that will later shape my essays.
Instead of trying to become louder or more polished, I decided to lean into how I naturally operate. I design systems that simplify, create clarity, and help people see what actually matters. That might sound abstract, but for me it’s very practical. So, I built one for myself.
I think of it as building a closet for my work. A closet is not about displaying everything at once. It is about knowing exactly what you have and being able to pull the right thing at the right time. I built my personal website, www.leofiascone.com, as a structured, organized repository of my academic work, writing, projects, and values. I do not expect anyone to read it from top to bottom. The point is not volume. The point is coherence.
That system is changing how I approach many components of this effort. It is giving me a way to compete honestly in a process that can favor natural salesmanship. In a way, creative organization enhanced my voice.
What surprised me most was how the system did not just organize my past. It accelerated my personal projects. Chicago Rising, my independent research initiative focuses on practical, nonpartisan solutions to Chicago’s kitchen table issues like unsafe transit, lead in drinking water, and affordable housing, grew directly from this framework. Because my thinking and research are structured, I am able to engage civic leaders and planners in serious conversations rather than abstract ones. That was new for me, and honestly, very intimidating at first.
The same clarity led to AI for Main Street, a project where I am partnering with a Chicago-area community bank to explore how ethical, low-cost AI tools can support operations without replacing human relationships. To deepen my understanding and credibility, I pursued university-level coursework at Johns Hopkins and the University of Pennsylvania. I didn’t do this to collect credentials, but because I knew I needed to learn faster with content that my high school didn’t offer. That visible commitment opened doors I did not expect, including a semester-long investing program with Goldman Sachs.
Nothing in this process involved shortcuts. Everything in my system represents real work I did. My system did not add anything. It made it legible.
Some people warned me not to explain this approach. They worried it might look like I was revealing a secret or trying to outsmart the process. I see it differently. In many fields, the most effective strategies are often questioned at first, not because they break rules, but because they work by aligning strengths with structure.
This is about how I think. I am a quiet builder who designs frameworks that help people do their best work without needing attention. For a long time, I thought not being the verbal leader was a weakness. Rather than hiding my process, I believe it is important to explain it.
That mindset is what I will bring to campus. Just as the Run-Pass Option reshaped football by reading the field instead of forcing a play, I will continue designing systems that respond to reality rather than resist it. I am not trying to dominate the room. I am trying to make the room work better. Whether in research, entrepreneurship, or public-interest projects, I will keep building ethical, adaptable frameworks that accelerate meaningful work and help translate ideas into real-world impact.
An Age-Old Debate: Is the Architect as Essential as the Salesman?
By Leo Fiascone
January 2026
I used to think my progress would be much faster if I could just “fake” a salesman’s personality, until a mentor threw me a lifeline with a phrase that finally fit: Leadership by Architecture.
Shark Tank Called & They Want My College Business Plan
By Leo Fiascone
December 2025
Most people don’t think of college applications as an early-stage business plan, but it sure seems that way to me.
Maybe it started freshman year in Introduction to Business with Mr. Latorre, a class I signed up for almost on a whim because it sounded practical and, somewhat reluctantly (at age 14), I figured it would be worth more than a study hall. I had no idea that one elective would change the way I think.
Mr. Latorre had a cool way of making Intro to Business feel almost like a competitive game or sport. Units like planning a life budget post college graduation, researching a stock portfolio, or pitching a business idea weren’t just assignments; they were challenges. They were fun. And they made me look at business in an entirely different way.
The biggest lesson, though, wasn’t about stocks or profit margins. It was about the value of a plan, a real one. A business plan forces you to slow down, think, and confront whether your idea makes sense before you spend money or time. It’s not dramatic or flashy, but it changes everything.
Around the same time, I learned the power of compound interest. A simple exercise on a compound calculator showed that investing $200,000 (the possible cost of four years of college tuition) at 20 could turn it into over $14 million by retirement. I realized that small, but intentional, decisions at young ages could shape entire decades of my financial future, for far better or for far worse.
Outside the business classroom, another adult has shaped the way I think about planning: Mrs. Marshall, my high school counselor. She has met with me each semester, each time I asked, to talk about goals, classes, direction, and how to best plan for the future by taking steps now. She encourages me to step outside my comfort zone in a way that always makes me feel positive. She doesn’t tell me what to do; she asks the questions that force me to think, just like a business plan does.
Fast forward to now: I’m a junior in high school preparing for the biggest investment of my life, college. And, naturally, the business part of my brain turned on.
If I walked into the Shark Tank studio and said, “I need $75,000, $100,000, maybe even $350,000 for a four-year venture,” every investor would stop me right there and say, “Where’s the plan?”
Because nobody invests six figures without one, except, apparently, for college.
We write essays, take tests, fill out applications, visit campuses, estimate acceptance chances, guess at majors, and somehow navigate the biggest financial decision we’ve ever made, all without being asked to write an actual plan.
If I pitched college on Shark Tank with no business plan, I can already hear Mr. Wonderful: “Kid, I’m the only honest one here. Take that idea behind the barn and shoot it. I’m OUT!”
And honestly, he wouldn’t be wrong.
That realization hit harder as I started reading about student debt. It’s in the news practically every week, and it’s now something like $1.7 trillion dollars, an amount so massive that even if Elon Musk, Jeff Bezos, Mark Zuckerberg, and Warren Buffett combined their net worths, they still couldn’t pay it off. That number shocked me. It’s one of those moments when the compound-interest lesson from freshman year acted as a warning sign, and I need to think ahead.
So I decided to do the thing that felt like common sense after everything I’ve learned. I wrote a business plan for college, one that includes my passion for urban issues (especially in Chicago) through personal projects like Chicago Rising and AI for Main Street, and the respect I have learned from the discipline that a degree in business can facilitate. It’s on my personal website for anyone to see: www.leofiascone.com.
I’ve been encouraging friends to write their own, not because I think everyone needs to do it my way, but because thinking ahead might help my generation avoid becoming part of the next trillion-dollar problem.
In the end, I’m simply trying to use what I’ve already learned in real life. Isn’t that the point of education?
None of this would have happened without a freshman-year business teacher who made business planning feel like a sport and a counselor who kept asking the right questions. Thank you, Mr. Latorre and Mrs. Marshall, you turned a random elective into a process I am using to help plan my future.
My College Business Plan: A 45-year Investment Thesis
By Leo Fiascone
December 2025
The Three Most Underrated Books I’ve Ever Read
By Leo Fiascone
(And Why They Deserve Their Own AP Class)
August 2025
If you’ve ever sat through an AP English class, you know how it goes. We spend what feels like weeks pulling Hamlet apart while everyone quietly hopes he’ll just make a decision already. We dig into The Great Gatsby until that green light practically needs therapy. We feel bad for Frankenstein’s monster, side-eye Macbeth for making terrible choices, and pretend we totally “get” Heart of Darkness even though the whole class is exhausted.
These books are supposed to be the big, important ones, the ones that shape us. And yes, they’re great for the AP test or for sounding smart when someone says “existentialism” in a study group.
But honestly? They don’t prepare you for real-life issues at all. They don’t explain why your first paycheck is way smaller than you thought and why that might cause your debit card to get declined on a first date at Chipotle (and yes, that actually happened to my friend). There’s nothing about how to cook actual food without setting off the smoke detector or why every adult in Chicago suddenly talks about credit scores like it’s the Bears versus Packers rivalry.
And nothing in Shakespeare teaches you how to do taxes, how to spot a bad lease, or how to survive your first job interview without accidentally calling your boss “dude.” You also won’t find tips on unclogging a sink, changing a tire, or understanding compound interest before it ruins your life.
At some point I started thinking maybe we’re missing the actual classics, the ones written by people who want us to survive adulthood without Googling “how to fold a fitted sheet” at 2 a.m.
So here are the three books that actually taught me something useful, and they’re way funnier than I expected.
Book 1: Grown-Up Stuff Explained by Witty Ryter
Imagine The Great Gatsby but Nick Carraway finally understands what an insurance deductible is. That’s this book. Seventy-five topics, credit, paychecks, basic money stuff, explained with cartoons. I learned more from one chapter than from all my time on TikTok.
Book 2: The Big Book of Adulting Life Skills for Teens by Emily Carter
This totally looks like something your aunt gives you for a 16th birthday. I rolled my eyes too, and then I read it. It covers real stuff, cooking something besides ramen, negotiating rent, figuring out car insurance, and knowing when your mechanic is exaggerating. It feels like a mix of survival guide and pep talk, which made it easy to read.
Book 3: Adulting for Beginners by Matilda Walsh
Think The Odyssey, but instead of cyclopes it’s student loans. Walsh somehow makes responsibility feel like an adventure. The line that stuck with me: being an adult isn’t about perfection, it’s about progress. You’ll mess up, overspend, burn dinner, whatever. You keep going.
None of these will ever show up in AP English. Macbeth wasn’t choosing health insurance, and Hamlet wasn’t debating airline credit cards. But if I could pick a new AP class, it wouldn’t be something like “AP Etymology” or “Why Words Are So Complicated.” It would be AP Adulting: The Science of Survival After You Leave Home, with real quizzes like “Read this lease. What’s sketchy?” or “Explain an HMO vs. PPO without panicking.”
These books won’t get you extra college credit, but they might save you from a bunch of dumb mistakes. And honestly, they reminded me that the stuff we never test, curiosity, problem-solving, being able to handle everyday disasters, might matter more than any metaphor we’ll ever analyze. For $23 and about five hours of reading for all three, it might be my greatest prep course.
What I’m Looking For in a College
By Leo Fiascone
June 2025
When you turn sixteen or seventeen and start your junior and senior years of high school, like clockwork, the most popular question you get asked by grandparents, family friends, college counselors, and everyone in between is “What college do you want to go to?” It feels like a rite of passage that seems harmless. For many students in that situation, they already seem to know their major, their career, and exactly how everything lines up. Let’s just say I am not fully in that camp. And while it might be easier if I had that certainty, I am okay with the fact that I do not, yet. I know the general direction I am heading in, which is a mix of urban issues, business, and AI. The details are still forming.
While high school is great for exploring, I think of college as a toolkit. Every class, teacher, project, and experience becomes a tool I might leverage later, even if I do not know exactly when. My family talks about three pillars for making decisions, which are what you enjoy, what you are good at, and where there is real demand. Those help me think through something as big as college. I do not want to chase an interest I am not good at, or spend years building skills without a purpose, or forget that the world changes fast enough that most adults end up having to reinvent themselves more than once.
I am generally a quiet person, but that does not mean I am not engaged. I learn by paying attention, thinking things through, and working hard behind the scenes. I like contributing in ways that are steady and useful, not loud or showy. For me, a good fit works both ways. A university should help a student grow, but the student should also bring something to the community. I am still young, so I am not claiming I will make some major impact, but I know I can contribute. I like creating small, practical projects that help improve real world issues. I enjoy working with ideas that involve data, cities, or community challenges, and I want to bring that kind of mindset wherever I end up.
I am drawn to colleges that support curiosity in a hands on way. Not slogans, but chances to try classes outside your major, work on projects that challenge how you think, and connect what you are learning to actual situations. I also know college is a major financial commitment, so curiosity has to be balanced with some focus. I generally know what I like, and I know the direction I am leaning toward. I just do not want to pretend every step is locked down before I even start.
I learn best when ideas connect to real life. What stays with me are the moments when something from class shows up in an actual problem. The projects I have taken on, such as Chicago Rising and AI For Main Street, came from wanting to understand how systems affect people’s daily lives and seeing where I could help even a little. That matters to me, especially in urban places where life is energetic and messy, and where ideas have to work in real life rather than just on paper.
Values matter too. I want to be in a place where fairness, responsibility, and ethics are part of the learning process instead of something separate from business or technology. My work on AI for Main Street really showed me how important it is for ethics to be built into the future of AI from the start, because the choices we make now will shape how people experience this incredibly powerful and very early stage technology in the near future.
A university’s reputation is great, but what matters more to me is whether the experiences it offers actually help students grow into someone who can be productive in life after college.
If I had to sum it up, I am looking for a college that fits the direction I am already moving in but also gives me the room to adjust and improve that direction as I keep learning. I am not expecting a college to hand me a plan. I am hoping for a place where the plan I am building makes more sense as I pick up new experiences, new skills, and a clearer idea of where I can make a real difference.
So I guess what I want is a college where I can contribute with where I am today and keep building from there. A place where the tools I collect, the work I do, and the experiences I have all help the bigger picture come further into focus, one piece at a time.
