Chicago’s own Pat “The Manager” Corcoran recently sat down with Complex for the latest installment of The Blueprint, a series hosted by their Editor-in-Chief Noah Callahan-Bever. Usually not one for interviews, Corcoran is in good company with this one as the series has previously featured industry titans such as Jimmy Lovine, Ronnie Fieg & Todd McFarlane to name a few. Clocking in just shy of an hour, Pat discusses everything from his early days in the city to his rise in the music industry as Chance the Rapper’s manager. Throughout the interview he gave much insightful perspective into his personal life, Chicago music, and finding success in the music business. Here are our four biggest takeaways from his sit down:

1. Trial and Error is the Best Way to Learn

Pat recalled in his early days starting a music blog with These Days’ own Eric Montanez and doing whatever they could to help artists through that outlet. During this time they threw their first show at Lincoln Hall with local artist Rhymefest. Unfortunately, the show happened to take place at a time where the majority of Chicago’s music scene was heading to Austin, Texas for SXSW, and the show fell far short of capacity. ”We didn’t know what the fuck we were doing, but we tried it and through trying it we learned so much of what we wanted to do.” Instead of taking this failure as an excuse to quit, Pat took this moment as a great learning experience and ironically found himself back at Lincoln Hall selling out the venue with Chance the Rapper the next year.

2. There’s No Job Too Small or Too Big

Prior to Chance the Rapper, Pat got his first break with Kids These Days, a band that featured most of Social Experiment and Vic Mensa.  “What led me to getting into [artist] management is when I met Kids These Days, and [I told them]] I will do anything I need to do for you guys. I tried to be around them as much as I could”. He seized this opportunity with the group and ran with it doing everything from running the merch table to making runs to fast food locations for the band. To outsiders, performing these tasks without pay may seem foolish, but Pat gained valuable experience and it opened doors for himself to further his career.

3. You Have to Have the Tough Conversations to Achieve Your Goal

After Pat and Chance decided to forgo joining a major label, they found that a number executives proved hard to work with when trying to lock down features with their artists for Coloring Book. Pat found himself having many hard conversations with high major label executives in order to get artists like Kanye West and Justin Bieber on the album.  “We just kept knocking on that door and being the good guys, centered about it and [trying to] create the best deal that would make everyone happy.” This tactic proved timely when dealing with Kanye’s label for his feature on “All We Got”. ”At the end of the day Chance had written three songs for Kanye the month prior, [Def Jam’s] Biggest artist of all time. They asked why are we supposed to allow you to [have a Kanye verse] and the retort would be, why do we have to allow you to keep the Kanye record up? Those were tough conversations to have.” These conversations ultimately were the key in order for Coloring Book to become the critically acclaimed project it is today.

4. Never Be Complacent

By now Pat already has achieved a lifetime of accomplishments from his artist landing multiple covers, three grammys, throwing the first concert at Guaranteed Rate Field, and maintaining Chance’s independence. Inner drive is essential to keeping the wins coming, and Pat points out that this is thanks to the mentality of never being complacent. “I want to be great, I want to be a big deal and I think that's half the battle. What Chance and I have done in little time has been incredible but I’m looking forward to changing the world even more, changing business even more and spreading positivity and optimism along the way.”