Office Hours with Ernest Wilkins
Office Hours with Ernest Wilkins
33: The Art Of Finessing

33: The Art Of Finessing

Eddie Sanders   Eddie is an experienced intellectual property attorney and former artist manager. With this combination of practices, he is able to provide effective solutions for entertainment and business clients. A native Chicagoan and John Marshall Law School grad, he currently operates; Freshly Baked Records, a music distribution company. In his free time, Eddie enjoys deejaying at your favorite nightclub or finding something bad to watch on Netflix.


Esquire — that’s what I call him, as do most folks — is an intellectual property lawyer based here in Chicago. In his career, he’s been a part of Chicago’s creative community as both an artist manager as well as a legal aide to countless members of the superstar musical talent the city cranking out on the regular these days.

Hear about his upbringing, the steps creatives need to build their business structures, how he pulled off getting engaged on-stage during Smino’s set at Lollapalooza 2019, what brands can do to get better creative partnerships (hint: It starts with realizing you need them more than they need you) as well as sharing a cultural concept native Chicagoans will recognize anywhere: The Art of The “Finesse”.

SONG OF THE WEEK: Guapdad 4000, “Flossin”


We’re 25 years out from World Cup 1994, my introduction (as well as a lot of people who look like I do) to international soccer. The final match was played here and one of my earliest memories is going downtown to my dad and seeing people in facepaint and in wacky costumes. From there, Chicago got the Fire (the MLS team, not the Dick Wolf series) and they won the title their first year in the league. Since then, things have ebbed and flowed.

Over the years, I’ve been fortunate enough to travel and see what soccer culture looks like in other cities and countries. Chicago’s segregation problem extends to our cultural exchanges (parties/events/any place where people who aren’t like each other can come together) and I think it’s what keeps soccer culture from truly catching on here — not to mention everywhere else. I want better for Chicago. So do a lot of other people.

One of those people, DJ STEP — the official DJ for the Chicago Fire — didn’t see it happening either, so we teamed up with The Fire to host the first of hopefully many quarterly events around soccer culture in Chicago.

Flyer has all the details! You gotta be 21+, but it’s free to attend.


The first paid subscriber-only newsletter drops next week. I’m sharing a list of books that creatives who want to boss up their business acumen should read that aren’t on the usual lists (No Rich Dad, Poor Dad or 48 Laws of Power nonsense) If you’re a free subscriber, you’ll still get next week’s podcast episode. Make sure you don’t miss out.

If you enjoyed this story, forward to a friend and tell them to sign up for the newsletter!
Office Hours is written by Ernest Wilkins. Follow him everywhere @ErnestWilkins

Office Hours with Ernest Wilkins
Office Hours with Ernest Wilkins
Office Hours Magazine is a new take on the B2B publication, focusing on the business of cultural industries.