About the Creator & How the CHICAGO LOVE™ Vision Was Born
In high school in Cleveland, Ohio, Ryan Lessam dreamed of moving to New York City and working in the music business. After graduating 2nd in his class at Full Sail University in 1997, he moved to NYC just days later to begin as an intern at the world-famous Quad Recordings in Times Square — cleaning studios, running errands, and learning from the best. From 1998 to 2005, Ryan worked at legendary studios including Quad, Unique, and The Hit Factory, engineering sessions with artists such as Jay-Z, Mariah Carey, Missy Elliott, Timbaland, DMX, Stevie Wonder, Alicia Keys, The RZA, Isaac Hayes, and Brandy. His success led him to open his own Manhattan studio, The Padded Room, where he focused on developing and producing artists of his own..
After leaving the music industry, Ryan bounced around before visiting a friend in Wicker Park/Bucktown in 2010. Experiencing a Chicago summer for the first time — seeing U2 at Soldier Field and realizing how welcoming and affordable the city was — he was instantly hooked. Within six months, he made Chicago home.
By 2014, Ryan felt the creative itch again. He picked up acrylic paints and began pouring, throwing, and experimenting with color and motion. He was mesmerized by how the paint moved and blended, creating something alive — and he knew he had found his new calling. That same year, he began taking classes at Lillstreet Art Center, discovering a deep passion for abstract painting.
Ryan’s inspiration to become an abstract artist comes from many places, but one of the pivotal moments that sparked his curiosity to experiment with paint came around 2011 and 2012, when he would spend his weekend nights at Danny’s — the iconic Bucktown bar and nightclub located inside an old apartment building at 1951 W. Dickens Ave. The vibrant graffiti murals covering the walls of the men’s bathroom lit a creative fire in Ryan, inspiring him to start experimenting with abstract art and to capture that same raw, expressive energy in his own work. Danny’s quickly became one of his favorite late-night spots to get his groove on — and a place Ryan will always hold dear in his heart for sparking the passion that ultimately led him to become an artist.
From 2014 to 2020, Ryan continued to paint while supporting himself through various roles in the craft-beer industry. That same year, some friends who had founded the Chicago-based brewery Hopothesis Beer Company invited him to invest and take over as Head of Sales. He jumped at the opportunity, invested immediately, and helped grow the company’s footprint and sales across the Chicago market by more than 64% between 2014 and 2017.
Hopothesis became known for its creative branding, bold flavor profiles, and connection to Chicago’s culture — values that deeply resonated with Ryan’s own artistic spirit. But when the majority owners decided to be acquired by Finch Beer Company in 2017, things took a different turn, and like many independent breweries post-acquisition, Hopothesis eventually closed its doors.
The experience gave Ryan invaluable lessons in entrepreneurship, brand-building, and creative marketing — all of which would later shape the foundation for CHICAGO LOVE™.
From 2017 to 2020, Ryan supported himself as Sales Manager for other local Illinois breweries including Wild Onion, Kinslahger, and Prairie Krafts, continuing to build relationships throughout the city’s vibrant craft-beer community while pursuing his art in his free time.
In 2020, Ryan had to leave his Ukrainian Village apartment in Chicago to care for his mother after she suffered a stroke. The next five years turned into the most challenging and difficult years of his life. Together they moved cross-country, living in three different states to obtain proper care.
By the summer of 2024, his mother had finally recovered to the point where doctors said she could live on her own again — a freedom she desired badly. She now lives near her daughters, grandchildren, and great-grandchildren in Cleveland, where Ryan visits regularly.
Ryan returned to Chicago — the place he loves more than anywhere — in November 2024. After going through such a difficult period — if it wasn’t bad enough having to live with his mother again for almost five years, having to do it while living in Florida for two of them was probably the worst of it all — Ryan came out the other side determined to reclaim his life.
Since returning to Chicago in late 2024, he has been working toward his long-term goal of becoming a full-time artist. This new chapter began with the release of limited-edition prints of his original artwork, available as of August 1, 2025.
Over the past eight months, Ryan also developed the vision for CHICAGO LOVE™ — the brand, mission, and community inspired by the city that has given his soul life again. As soon as he returned, CHICAGO LOVE™ was born. Coming back home to Chicago has sparked and filled Ryan with so much joy and inspiration to continue creating. CHICAGO LOVE™ is his way of sharing that feeling — a place where everyone can be part of celebrating this great city.
There’s much more art to come — stay tuned.
The Birth of CHICAGO LOVE™
Back home in Chicago, Ryan felt something shift. The city’s energy, its grit and warmth, reignited his soul. He wanted to give back — to create something that celebrated Chicago’s neighborhoods, its people, and its stories.
That’s when CHICAGO LOVE™ was born:
A Brand that blends art, storytelling, and community.
A Community — a place for everyone to share what they love about Chicago and connect with new places and people.
A Mission — a way to give back to all of Chicago.
CHICAGO LOVE™ represents Ryan’s belief that art can do more than decorate walls — it can build bridges between people, spark hope, and remind everyone what makes this city special.
Through projects like the limited-edition “Vivo” bracelets, the upcoming coffee-table keepsake book (Product A), and community initiatives that highlight local voices, Ryan hopes to share that spark with others.
CHICAGO LOVE™ is more than a brand — it’s a way to give back to the city that gave him life again.
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