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Meet Gregory Reintjes of The Windy City Ball in West Loop

Today we’d like to introduce you to Gregory Reintjes.

Gregory, let’s start with your story. We’d love to hear how you got started and how the journey has been so far.
I am a firm believer that my generation is more socially aware than any other generation in the past. The digital age has given us unprecedented access to knowledge about the world, both the good and the bad, which can be both a blessing and a curse. I helped co-found The Windy City Ball with two friends from college at Vanderbilt (Pat Healy and Mills Rendell) and one friend from my hometown of Kansas City (Bradley Wiedeman) because we all recognized that there was a niche of individuals in Chicago who cared about philanthropy but didn’t know the correct outlet. There is a natural alignment between a social activity and a philanthropic event that no one else our age was doing in Chicago at the time (2013). There were larger events geared towards young professionals such as Snowball but these were run by entrenched, old school organizations like the Junior League. We thought “Why can’t we do something like this?” We knew there were people who wanted to learn more about charitable causes while also having a wonderful, sociable evening so we created an experience where a young person (like us) could have both. We have partnered with a different charity each year and we are now in our 4th year of running the event. To date, we have raised close to $70,000 for different charities and we are hoping to raise another $40,000-$50,000 this year. At first, we had no absolutely no idea what we were doing and we have gotten progressively better at managing the margins of the event and legitimizing our organization with corporate sponsors. Today, we have a strong associate’s board that helps run the event and all the co-founders are still involved in some capacity or another.

Has it been a smooth road?
Define smooth! Haha. The first year was a challenge for a number of reasons. First, we had to incorporate ourselves as a 501c3 organization with the IRS and register ourselves with various federal and state entities in order to operate as a non-profit. This, being Illinois, means we had to be vetted by a lot of different parties before we could secure non-profit status. Second, we weren’t particularly effective at making ourselves as profitable as possible for our charity partner. Companies were less inclined to donate things like food and beverage for the event when we were a brand new organization run by a handful of 23 olds who also had their own day jobs. In Year 4, we run pretty efficiently although we are always looking for ways to make the event more cost-efficient since it ultimately affects how much money we can donate to our charity partner each year.

So let’s switch gears a bit and go into The Windy City Ball story. Tell us more about the business.
Our company, The Windy City Ball, throws a charity ball each year in Chicago that is geared towards young professionals who want to learn more about a select domestic/international charity. We average over +600 attendees each year and we have helped build orphanages in South Africa, a playground for a school in the Hermosa neighborhood of Chicago, and assisted a meal delivery service for cancer patients in the Chicagoland area. This year, we are partnering with a home for children with severe psychological and behavioral disorders in Evanston. I am most proud of the fact that no one on our team does this as a full time job and this is something entirely detached from our day jobs. It’s not always fun to work on this after you’ve been in the office the whole day but I think it gives my life a renewed sense of purpose whenever we get to present that check to the charity. One of the coolest moments was in year 2 when we partnered with a local family to build a playground for a lower income school in Chicago where the kids had never had a gym or playground. This was the first active play space for them and we got to show the kids the playground after we built it. If I drive there and see those kids playing and laughing on that playground, it gives me a real sense of how impactful our organization can be.

What sets us apart from other organizations like ours is that we aren’t supported by a big budget or a larger parent entity. We are the definition of a “side hustle” that has become more significant than we ever could have imagined. I am extremely proud of the fact that a handful of normal people decided to dedicate their free time to something outside of their day jobs because they wanted to help build awareness for some amazing charities. We didn’t take out loans or rely on anyone else’s support to start this-we just did it.

How do you think the industry will change over the next decade?
We are a niche within a niche within a niche-I probably haven’t done enough due diligence on the non-profit event industry! Overall, I would expect these sorts of events to always have a place within our society. Our generation wants to socialize but we also care about the purpose and rationale behind that socialization. The desire for “purpose” extends beyond socialization to consumer products (TOMs, Warby Parker, etc…) so I would only expect to see more marriages between philanthropy and everyday activities.

Pricing:

  • Standard admission tickets to the event are $100
  • VIP tickets are $150
  • You can also donate directly to The Windy City Ball and 100% of those donations will be sent to this year’s partner charity

Contact Info:

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