An image of the interior of the under-renovation io theater. There are walls with bright panels and cubby holes, and ladders set against brick walls. In the foreground is a desk with chairs.
Coming soon: a new and improved iO Credit: Courtesy iO

After the comedy revolution during the COVID-19 pandemic, when many performers began speaking out about toxic culture in the sketch and improv world, iO was one of the many theaters that had to close its doors, seemingly for good. Upright Citizens Brigade, which began its life in Chicago, closed its longtime New York venue; they also faced charges that they had fostered institutional racism. While many theaters remained open, mainstays like Second City had to completely rethink their mission towards diversity and inclusion. 

After the iO space was purchased by real estate executives Scott Gendell and Larry Weiner in 2021, it, too, needed such a makeover. Annoyance Theatre’s Jennifer Estlin and Mick Napier stepped in to help guide iO into the comedy future. 

For Estlin and Napier, the most important step was hiring a core management staff. These newest staff members are an integral part of the conversation in filling in the blanks on what is happening with the new iO.

Under Charna Halpern’s management, iO faced allegations of institutional racism, leading to a petition from BIPOC performers that circulated prior to Halpern’s decision in summer of 2020 to close the theater. There had also been earlier allegations that Halpern had not done enough to address a culture of sexual harassment both in Chicago and at the now-shuttered iO West. Halpern and iO weren’t alone in facing such allegations; Second City՚s former owner, CEO, and executive producer Andrew Alexander stepped down in 2020 after Black performers went public with what they experienced there, and SketchFest founder Brian Posen stepped down in 2018 from the festival and as executive director for Stage 773 in the wake of widespread allegations of sexual harassment. (That venue is in the process of reinventing itself as Whim, an “experiential theater” with cocktails.)

The familiar pattern is that theaters caught in these controversies often hire “diversity consultants,” but, for those who have followed the scene for a while, it often feels like a never-ending trail of “woke-washing” in hopes of convincing us that these institutions are actually trying to do better. 

All that being said, much rests on the backs of new iO artistic directors Katie Caussin and Adonis Holmes. Caussin has been around the improv scene for many years as a performer at iO, Second City, and the Annoyance and knows the nuances and history of the community, their performers, and producers. Holmes is newer on the scene but has been highly involved in both the Annoyance and iO. He is currently a Bob Curry fellow at Second City (a program designed to foster diverse talent, named for the first Black member of Second City’s resident company). 

Not every team member is new to iO. Managing director Steven Plock worked at the theater before they closed their doors in 2020. Plock’s institutional knowledge means he is very familiar with how the business was run previously, for better or for worse. During the pandemic, Plock went out west and worked at a “cowboy bar,” so he’s surely ready to wrangle whatever needs wrangling. His food and beverage experience is a plus, since that’s a major area of revenue for the for-profit theater.

Classes are also a major revenue driver, and Rachael Mason, known as one of Chicago’s top improvisers and instructors, will be leading classes as director of education. Mason will be managing the entire class program. Online classes, taught by longtime veterans such as Susan Messing, have been running for around three months already

When Estlin met Kim Whitfield, she was doing a show at the Annoyance. Subsequently Estlin hired her to direct a show Annoyance was coproducing with Dispensary 33. Whitfield joins iO as managing producer, along with technical director Kyle Anderson and Jesse Swanson, executive director, special programs/content. Swanson was formerly a production manager at Second City and producing artistic director at Off-Color Comedy in Philadelphia.

“What a great thing if we can actually pull off an iO that has all the good stuff and gets rid of the bad stuff.”

It appears that diversity among staff is a priority and will continue to be for the new iO. Racist trends die hard, and have been known to kill theaters in the past in addition to alienating incredibly talented performers of color. What is also clear is that the new staff assembled with the input of Estlin and Napier all have deep roots in the improv and comedy scene. 

By contrast, the new owners Weiner and Gendell do not, though they excel at the “business” side of running a business. The ownership team now also includes Steve Sacks, who recently sold his family’s truck-parts business and has put his focus and interests into iO. Sacks does have a history with comedy performance himself, having performed stand-up in Chicago and New York. Of the three owners, Sacks will be serving as iO’s CEO. He has become the most involved on a day-to-day basis, maintaining an office in the iO building on Kingsbury. When Sacks got involved, he read the petition that so many people had signed, and this was the driving force to his involvement in the investment process. Sacks says, “What a great thing if we can actually pull off an iO that has all the good stuff and gets rid of the bad stuff.”

In regards to how exactly Sacks and the team will combat years-old discrimination issues, Sacks had this to say: “It’s not enough to set up a diversity, equity, inclusion, and accessibility (DEIA) team and say, ‘Yeah, we checked that box.’ We really do want them to help us with concrete steps necessary to make performers and audience members feel safe. BIPOC performers didn’t feel comfortable, and we want to make sure they do feel at home and that this is a place they can thrive.”

In contrast to the way iO used to be run, Sacks states, “We’re not doing what was done before, which is one person deciding who does or doesn’t go on stage. One person deciding who is and isn’t paid. These decisions are going to be made collaboratively, and ownership is going to stay out of those decisions because we don’t want it to be a colonized management system. I think the DEIA is going to hold our future to the fire. Mistakes will be made, but we’re going to have to figure things out as we go along. We are doing it in the spirit of collaboration and healing, the spirit of equity. That’s our objective.”

When it comes to working with owners who largely aren’t from comedy backgrounds, Estlin has found collaborating with them to be quite refreshing, as they are the first to admit they don’t know anything about theater.

“These are great people, and they have been super nice to work with, very supportive,” says Estlin. “It’s always amazing when someone says they don’t know anything about a topic. They are like sponges, soaking up every bit of knowledge,” adding, “They’ve put a lot of trust in Mick and I. It’s nice when someone asks you for help and actually trusts the help you are offering.”

Building renovations are still underway and started about a month and a half ago under the direction of longtime Chicago scenic designer Bob Knuth, who has been generally working to make the bar area warmer and more conducive to hanging out with lots of people. Audience members should expect to see a refreshed and enlivened space.

Renovations at iO are expected to be finished by the second week of September, at which point they’ll begin hiring support staff for hosting, bartending, and box office. Sacks says, “Ownership believes that we can add value on the renovation of the building in creating a cozy and relaxing vibe and in allowing and facilitating our team to create hilarious shows. These creative decisions will be made in the most collaborative, equitable way possible.” Though construction and permit delays are always part of the equation, iO aims to have a soft open by early fall, with hopes of having an opening celebration closer to winter.

As far as growing postpandemic, Estlin says, “We’re constantly having to remind ourselves that the old is the way things were, and this is what we do moving forward. We want to make sure it’s an equitable space that provides opportunities for as many types of people as possible. That is super important to all of us.”

Sacks and the team are committed to producing high-quality comedy. “The shows have to be funny. The quality has to be very high, and we believe there are enough talented diverse BIPOC and para-ability comics alike. We want it to be funny; we want it to be edgy. We want it to be challenging! We want to be proud of what we’ve done, and we all want to do something good for the community. If it can be a place of momentary joy and belonging, then we’ve done something. It’s an amazing, fun challenge for us. I get to hang out with these talented people, it’s like a blessing. Our goal is to earn the trust of improvisers, work staff, and audience members who may not have felt safe or comfortable at iO. We’ll strive to create a supportive, inclusive atmosphere, and we want people to hold us accountable to that. There was a lot of trauma, and we have to gain the trust of talented improvisers that would like to perform here.”

It’s yet to be determined what iO’s place will be in this new comedy landscape, but, given its long roots in Chicago, it’s a safe bet that expectations will be high. The theater has already started programming shows that will be ready to go up toward the beginning of fall. With the help of Estlin and Napier, and the business savvy of these new owners, iO looks to be on the road to make amends for decades of damage. With so much riding on the necessary changes to its previous exclusive culture, audiences and performers alike are eager to see the future of iO.

2022 Fall Theater & Arts Preview

A fall edition

A note from the Reader’s culture editor who focuses on film, media, food, and drink on our Fall Theater & Arts Preview issue.