Two years ago, Ryan Laessig stepped into the role of Executive Director of the East Side BID. Somehow, in just two years, he’s managed to squeeze a whole lot of ideas, events, murals, new businesses, bike rides, plaza parties and ambitious neighborhood projects into the mix.
So, in honor of Ryan’s second anniversary, we’re taking a look back at a few of the things that made this past year such a big one for the East Side.

One of the biggest shifts this year has been the way Ivanhoe Plaza has become a true gathering place for the neighborhood.
Ryan has worked to expand the use of the plaza, encouraging community groups, businesses, artists and event organizers to bring their ideas into the space. Over the past year, Ivanhoe Plaza has hosted markets, music, community events and plenty of reasons to stop by, hang out, and see what’s happening. It’s been exciting to watch a space that started as a temporary project become part of the everyday rhythm of the East Side.
And this year, Ryan, the East Side BID Board and Korb Architecture took a major step toward imagining what comes next.
The Ivanhoe Plaza fundraising project officially kicked off this year, launching an effort to turn the temporary plaza into a permanent community space. Through deep collaboration with the BID Board and Korb Architecture, Ryan has helped develop plans for the future of the plaza and what this space can become for the East Side.
The vision includes a permanent concrete plaza, seating and landscaping, shade, improved accessibility, infrastructure for performances and events, and signature features like the Leaf Canopy, Community Stage and Flex Park. It’s a big project, but it also reflects something that has been at the heart of Ryan’s work this year: thinking beyond what the East Side is today and helping build what it can become tomorrow. Interested in making your mark on the Plaza? Explore ways to get involved: ivanhoeplaza.theeastside.org/.

If you spent any time on the East Side this year, you probably noticed something: there was a lot going on.
Summer Soulstice Music Festival, the Rolling Bike Party, East Side Gallery Night, Black Cat Alley After Dark, and Doors Open Mural Fest all gave people a reason to get out and experience the neighborhood, and they’re just a few highlights from a very full event calendar.
A big part of what makes these events special is that they’re free and open to the community. They give people a reason to come to the East Side, explore a little, grab dinner, shop at a local business, check out a new mural, and meet up with friends. And for the businesses, artists, and organizations that call the East Side home, these events create opportunities to welcome new faces and be part of the larger community.
Many of these events also continue the East Side’s long-standing identity as Milwaukee’s “creative crossroads.” Art and creativity are woven into so much of what we do, from Gallery Night and Doors Open Mural Fest to the ever-changing walls of Black Cat Alley and the creative programming that fills Ivanhoe Plaza. It’s a tradition Ryan has continued to build on, creating more opportunities for people to experience the East Side as a place where art, culture, business, and community all meet

Black Cat Alley has had a busy year, too.
Ryan has continued working to improve and care for the outdoor gallery, from adding another new mural to restoring existing artwork and installing plaques that help visitors learn more about the artists and murals throughout the alley.
It’s easy to think of Black Cat Alley as a finished project, but keeping a public art space like this vibrant takes ongoing work. Want to show your support for the Alley? Consider donating to provide supplies for artists to create and maintain their murals, weatherization for the murals to protect them in winter, general maintenance projects, and security of the alley at blackcatmke.com/support.

A thriving neighborhood needs great places to go, and in Ryan's second year of leadership we had the pleasure of welcoming even more businesses to the East Side, including Lowwstock Vintage, Jalisco’s Cocina y Bar, Smokin' Jacks BBQ, Studio B & Co., Blue Hour Coffee, The Waxwing, and Star Bar.
Ryan has continued building relationships with businesses throughout the district and finding ways for the BID to support the people who make the East Side what it is. One example is Poppy Bakery, which secured a BID Security grant this year, helping support safety and security efforts for the business.
Because, naturally, Ryan didn’t stop there.
This year also saw the fundraising effort for the North Avenue Mural Project come together, bringing us one step closer to adding another piece of public art to the neighborhood. The mural itself is still ahead, which means we get to save that celebration for another day!
Two years into Ryan’s time with the East Side BID, there’s always another project underway, another idea taking shape, and another reason to be excited about what’s next.
So today, we’re celebrating the two years of work that have already made an impact, and the many projects still waiting around the corner.
Happy second anniversary, Ryan! We can’t wait to see what year three brings!
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