Meet The CEO

 

Robert Webb – Founder of Freshman

My name is Robert Webb. I was born on October 17, 1995, and raised on the South Side of Chicago, IL. Growing up, I always had a passion for clothes and style. I got caught up in the streets at a young age, selling drugs—not because I didn’t know better, but because I was chasing the money to keep up with the lifestyle, the sneakers, and the fashion I loved.

Eventually, that path landed me in jail. That time gave me the clarity I needed. I realized I didn’t need to sell drugs to make money—I could create something real, something mine. That’s when I came up with Freshman—a brand built on hustle, growth, and second chances. Now I design and sell my own clothes, giving people quality fashion at fair prices, and a story they can believe in.