Dozens of enthusiastic tourists taking to the streets of Chicago is nothing new, but mix in the task of connecting these accomplished visitors with local entrepreneurs, artists, and community leaders — all within a 48-hour period — and you have the makings of a “Breakout.”

‘Breakout’ is a community that champions change makers,” said Michael Farber, a “card-carrying” millennial who co-founded Breakout four years ago. “We have members from over 22 markets we call ‘breakers’, people from 15 different cities, from all kinds of socio-economic groups, from all different industries, and we’re connecting them together to change the face of impact.”

Farber said the idea of each Breakout is to introduce people who would not normally be rubbing elbows and have them take part in a variety of unique experiences in the hopes that magic will happen — which is most often the case.

“We’ve had people get married, we’ve had people start businesses — all sorts of connections,” said Farber, who now calls Chicago home after doing research for the Breakout event. “At the end of the day, people aren’t coming with business cards, this is to make real relationships and when they make real relationships, they’re actually going to find ways to work with each other. Everything we do is immersive, and we don’t do anything in hotels.”

Chicago was home to the 10th Breakout this past weekend, with 150 participants registered. (Other cities to host past Breakouts include Detroit, Atlanta and Miami, to name a few.) Participants are asked on an invitation-only basis, and recommendations often come from other breakers. While the price tag varies from city to city (between $1,000 and $2,000 per person), all meals, lodging and activities are included. Scholarships and partial scholarships are available because Farber insists on choosing people from many different careers and economic backgrounds.

“I’ve had friends ask me ‘What’s going on in Chicago? It’s so violent,’” Farber said. “When you’re here you know the vast things that are occurring culturally, historically, entrepreneurially, and so it’s an opportunity for us to tell the story that we feel is the true story.”

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Telling that “true story” was the task of many local artists and activists who were given a platform to showcase the many talents and tones of Chicago.

“What’s the point of being in a city if you’re not actually having a relationship with it,” said Xavier Ramey, CEO of Justice Informed, and the speaker who kicked off the Breakout Live show Friday night at the Studebaker Theater on Michigan Avenue. “We have a responsibility to engage. It’s not an option… One of the things I would tell all the young cats I used to mentor is, ‘If it is to be, it’s up to me.’”

The Studebaker Theater event (which was open to the public) also included musical performances from many local artists and activists including rap from Pinqy Ring, poetry from Bella BAHHS, and words of wisdom from Pastor Chris Harris, Embarc Co-Founder Imran Khan and a song from artist and former Hamilton cast member Ari Afsar. Keeping the show on track was Master of Ceremonies Simeon Dill, co-owner of the O.A.S.I.S. Barbershop in Pilsen known for hosting “Shop Talk” community conversations every other week.

“I’m hosting one of the dinners that’s happening tomorrow,” said Dill, one of many Chicagoans sharing his space throughout the weekend. “This is my first Breakout, but Michael (Farber) and I, we’re both trying to do the same thing, which is get people talking and connecting in a comfortable environment.”

Other events and experiences for the weekend included a block party in Englewood, a live concert at a tire warehouse in West Town and conversations with community leaders in Back of the Yards. Festivities wrapped up with a group meditation on the Observation Deck of the Willis Tower Sunday morning.

“My generation, the millennials, we’re very comfortable talking about a lot of stuff,” said Rich Murray, a financial advisor for AllianceBernstein taking part in Breakout in hopes of connecting his firm to the next generation. “But we want authentic relationships first. You don’t just want to do business because it matches up on the resume, you want to do business because you actually like that person. I want to feel comfortable that I can be vulnerable in front of that person. That level of trust- I don’t think that’s new, but the older generation hasn’t figured out how to bridge that gap. My big value proposition as a financial advisor is being able to connect those communities with my mentors, and create authentic relationships.”

With the weekend festivities in the rearview mirror, Farber is relieved all went well, but still constantly looking for more entrepreneurs, artists and experiences to keep connecting those dots.

“There are definitely some big business deals happening throughout Breakout, but those aren’t the stories I’m as excited to tell,” Farber said. “Seeing some of the relationships that come from this, the lifelong friendships … we’ve seen statistics, entrepreneurs are not happy people — we work and work and work and we’re actually quite depressed. So I think people trying to find real meaning and purpose is really the biggest thing we’re trying to figure out.”