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Horn Entrepreneurship

From Horn to Beyond! Lilly Checkoff and Her Life as a Horn Graduate

University of Delaware 2022 graduate and former Horn Ambassador Lilly Checkoff began her start in entrepreneurship at a very young age. With her non-profit Tools For School, she provided thousands of backpacks and school supplies for underprivileged children. This non-profit guided and inspired her to surround herself with all things business once accepted as a University of Delaware freshman. Through her time at UD, she became heavily involved with Horn's different programs and excelled as a responsible student of entrepreneurial leadership. Now, as a 2022 graduate, Lilly aims to make the world her own and use her background in entrepreneurship to guide her. 

I was able to spend some time and chat with Lilly about her non-profit startup and how it prepared her for her college expenditures and future in entrepreneurship.  

Tools For School

At the bright age of twelve years old, Lilly Checkoff was shopping for school supplies with her mother. As one of four siblings, Lilly couldn’t help but notice just how hefty the final bill was. This got her thinking about underprivileged and underserved families and how exactly they provide their children with school supplies. Young Lilly got to work and founded Tools For School, a non profit organization that raises money to purchase backpacks and school supplies for children whose families can’t afford them. In this interview I was able to conduct further research on the nonprofit and how she managed to build a successful startup at such a young age. 

How did you get Tools For Schools started since you were only twelve years old?

Lilly: It really started by me asking friends and family for donations. In addition to that, I remember I would walk up and down the beach with my friends, and we would give away pretzels in exchange for a donation of $1 or more. So those were our two main fundraising methods that year. And then with the help of my parents, we were able to order 100 backpacks and enough school supplies for those 100 backpacks and pack them. The organization has since evolved to a much larger scale.

Is it still operating? If so, do you still have a part in the events or fundraising? 

Lilly: It is still operating largely under my sister's leadership, which I'm very grateful for. My sister is a sophomore at the University of Pittsburgh. When I graduated high school, she took over Tools For School. But yeah, she is insanely motivated to continue Tools for School and keep pushing forward for it to grow. Which is just, it's really amazing for me to watch, because I did, unfortunately, think that it was going to die out after I graduated high school. It has become more than I could have imagined thanks to my sister taking over.

Lilly began to explain that just last year Tools for School reached a mindblowing 10 year milestone and celebrated by packing their 10,000th bag! Needless to say the non-profit is in good hands.  

College Experiences 

With her early experiences in things such as startups and nonprofits, Lilly was well equipped for life as a hard working college student. 

How did Tools for School prepare you for college and working on ventures there?

Lilly: Working on Tools for School definitely built my confidence in my ability to put myself out there and kind of go after what I want or need. For example, fundraising. I was in high school, and I was calling corporate sponsors, asking them for money. Which was obviously no easy task. It's still not easy. But I guess it really taught me to pitch myself and pitch what I believe in. And in addition to that, it also taught me a lot about

leadership and motivating a team of people to have an aligned vision.

With this newfound confidence, Lilly was able to get involved with different ventures and programs right here at Udel. She starts off by explaining how she was inspired by our own Ted Foltyn's Landing Your Dream Internship class and how it led her to network with the CEO of Trapica. In doing so, Lilly landed an internship with the venture and quickly grew into a more associative role. Thereafter, Lilly was awarded with Horn’s Brad and Jennifer Bono award, which celebrates an undergraduate who demonstrates entrepreneurial leadership and social impact. After calling Brad Bono to thank him personally the two discussed a possible business partnership in the future. 

Lilly: He (Brad) was like, listen, I have this idea, and I want to know what you think of it. Or I'm curious to hear what you think of it. And I was like, I love your idea and when you start working on it,  I want to work for you. Fast forward like nine months later, in June of 2021 I started working for him as a business development intern at his company Aspire . It was one of the most eye opening experiences that I probably had as an aspiring entrepreneur because I got to work from ground zero, pretty much.

At Aspire, Lilly began as a business development intern but her role quickly evolved into one centered around handling connections between different higher-ups to further build the business. 

While at Horn, Lilly also participated in the winter study abroad program where she got the opportunity to study and learn from the tropical state of Hawaii! There she took a Special Topics and Entrepreneurship course where she learned about workplace etiquette and culture. In traveling and taking this course, Lilly was piqued about workplace culture and began to realize its potential to be her future career. 

Horn and Beyond

While managing these different positions and progressing through life as a college student has come with its ups and downs, Lilly explains how grateful she is for all the different opportunities that Horn has and continues to offer her. 

Did anything you experience while being at Horn prepare you for the direction you're taking in life right now?

Lilly: Horn has helped me find confidence in choosing not to follow what some people consider a typical path. In addition, Horn has helped me learn more about who I am as a person and what I'm interested in and passionate about. Also, I am grateful to have built relationships with almost all of my professors because they've been a great deal of help since I've graduated, especially in helping me find direction.

Thanks to this newfound confidence as well as her study abroad program, Horn has inspired Lilly to travel to Australia this October and build a life and career from the ground up. 

The Future 

Toward the end of our chat, Lilly wanted to sign off by sharing some advice for Horn's future entrepreneurs. 

Lilly: Spend as much time in the VDC as you can. I found the most value in my college experience when I was surrounded by entrepreneurial people and that's the place to be. There's so many cool people there. You never know what kind of opportunity or person you'll come across.

About Horn Entrepreneurship


Horn Entrepreneurship serves as the creative engine for entrepreneurship education and advancement at the University of Delaware. Currently ranked among the best entrepreneurship programs in the US, Horn Entrepreneurship was built and is actively supported by successful entrepreneurs, empowering aspiring innovators as they pursue new ideas for a better world.

Topics: entrepreneurship, careers, alumni