Making New Friends Is Easy As Pie With This Chicago App

DOWNTOWN — Christie Jackson woke up Thursday morning anxious about going alone to a run club filled with strangers. 

But before she arrived, Jackson opened Pie, the social events app hosting Zoomies Run Club, and found a chat filled with people admitting they were just as nervous.

“Everyone is saying they’re also anxious. They’re coming alone. It really helped me feel more at peace, feeling like I’m gonna meet other people like me,” Jackson said.

By the end of the morning, participants were exchanging contact information, following each other on social media and making plans to meet again during Lollapalooza weekend.

The gathering offered a glimpse of what Chicago-founded Pie says its platform can accomplish when enough organizers, events and users converge in one city. The company is now trying to replicate the model across the country.

Pie is a social media platform started in 2020 by Chicago native Andy Dunn, who co-founded the menswear company Bonobos and later sold it to Walmart. The company, which now has offices in River North, was originally intended to help people make friends through a one-on-one model, but shifted to an event-hosting-type platform in 2024, according to Inc. 

Earlier this month, Dunn announced he was bringing in entrepreneur and content creator Nadya Okamoto as the company’s new co-founder and chief marketing officer. Okamoto is the founder of the period care brand August and has a whopping 5 million followers across all social media platforms.

The goal? Tap into the Gen Z generation, which the app took off with, Dunn said in a Substack post in July.

Even more so, Okamoto has been tasked with helping Pie attract the organizers and active users needed to recreate the busy, event-filled experience the app has developed in Chicago.

Okamoto first encountered Pie as an organizer herself. She launched Zoomies, a run club, with her sisters late last year, but found herself piecing together several tools, including Instagram, email, text messages, an event-planning platform and a website, to manage it.

When she was introduced to the app, Okamoto said it immediately felt like the “centralized organizing tool” she had been missing. She began sharing feedback with Dunn, who was an angel investor in her company, August, and she later came on as adviser to Pie. After helping the app build a presence in New York, she officially joined its leadership team.

One of her main responsibilities is helping Pie replicate the experience it has developed in Chicago and grow it in other major cities.

Pie currently has 330,000 users. About 150,000 of them are in Chicago, which has created what Okamoto calls “social density,” or enough event hosts and attendees that users can regularly open the app and find something to do.

Users who download the app are prompted to create a free profile and answer questions about event preferences and hobbies. The app will give you a personalized feed with upcoming local events. Users can also add friends and see what events they are attending.

According to data provided by Pie, the app’s most popular event categories are night markets, run clubs and DJ sets. Participation varies by city. DJ sets and artisan markets are the most popular in Chicago, while New York City users favor fitness events, run clubs, listening parties and watch parties. Matcha tastings and wellness pop-ups lead in Los Angeles, while identity-based meetups and day parties are most popular in Austin.

In Chicago, creators on the app include groups like Windy City Cowboy Club, Chicago Beach Clean Up, Sin Titulo, Meet Your Neighbor Chicago, local DJs and small businesses. Events range from ticketed and free events to people looking to meet up to see certain artists at Lollapalooza.

The city’s social density was visible Thursday morning as at least 100 people gathered for Zoomies run club. Some attendees were longtime Pie users and others had downloaded the app specifically for the event.

For friends Nik Zakimi and Aizat Azmi, who were visiting Chicago for Lollapalooza from Canada and Malaysia, the run offered an opportunity to meet people in a city where they knew few others.

Zakimi discovered the event through Okamoto’s Instagram page and sent it to Azmi. The pair downloaded Pie to register and used the app to see who else planned to attend. They enjoyed seeing some of the chatter between attendees, which helped ease the anxiety of not knowing anyone.

“Coming in as an outsider, it definitely is a relief to meet or somehow know some people before going to a real event,” Azmi said. “It gives you some sort of insight into how friendly these people are [while] … establishing common ground before heading into a big event.

“This was a good way to meet people.”

By the end of the run, the two met someone new and were discussing plans to meet her at the lake later in the weekend, Zakimi said.

Other attendees also agreed that Pie’s chat feature made it easier to attend events alone because users could introduce themselves and make plans before arriving.

Some runners told Block Club they had already used Pie to find workout groups, parties and other gatherings around Chicago. Isabella Pak said she discovered a mahjong event at Gangnam Market, an Asian grocery store in West Town, and used the attendee list to find a group of four to play with.

Karina Rodriguez, a suburban Chicago resident, said she had organized faith-based gatherings, volunteer events and a field day through Pie. The platform made it easy to promote events and contact attendees afterward, even if they had not exchanged phone numbers, she said.

The larger test for Pie, however, is whether those interactions continue after an event ends.

Annais Gangolf said she met three women at previous Pie events who later reached out to her. She also had plans later in the week with some of those same women.

“I go to a lot of events in Chicago, and that’s not something that typically happens,” Gangolf said. “Sometimes there’s a continued connection, but I really find the people that Pie draws, and also the way that they engage their users, makes for a continued connection.”

Okamoto said those repeated interactions are central to Pie’s model. Instead of matching two people for a one-on-one meeting, the platform places users in group settings organized around shared interests, where they may encounter the same people again.

“Going on a one-on-one friend date is intimidating, but going to a run club where there’s 300 people and everyone’s there to mingle and make friends … takes that pressure off,” Okamoto said.

To keep the event lineup active, Pie is also temporarily incentivizing organizers to join the platform through its creator rewards program. Organizers are compensated for hosting events and driving new sign-ups by as much as $3,500 a mnth, Okamoto said.

The program is open to established community organizers but Okamoto stressed the company also wants folks who have always wanted to start hosting events but never had the tools to do so.

The supply of events will be critical as Pie continues on its journey to expand toward its first one million users. The success will depend on whether people not only download the app, but also continue to use it.

“We want a million users, but we don’t want it to be like they downloaded the app and then they never came back,” Okamoto said.

For the runners making plans after Zoomies, Pie has already cleared the first hurdle: giving people a reason to show up and someone to see again.