The Office Hours Interview w/ Ernest Wilkins

THE OFFICE HOURS INTERVIEW: Eddie “Esquire” Sanders

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”

COME TO THIS IF YOU LIVE IN CHICAGO: Can I Kick It?

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.

SUBSCRIBER UPDATE:

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

This is a public episode. Get access to private episodes at officehours.substack.com/subscribe

The reveal of XXL Magazine's Freshman List is one of the biggest moments on the hip-hop. Ernest and Alex discuss ways to market around the List to increase it's relevance -- and revenue.

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

This is a public episode. Get access to private episodes at officehours.substack.com/subscribe

The reveal of XXL Magazine's Freshman List is one of the biggest moments on the hip-hop. Ernest and Alex discuss ways to market around the List to increase it's relevance -- and revenue.

The reveal of XXL Magazine's Freshman List is one of the biggest moments on the hip-hop. Ernest and Alex discuss ways to market around the List to increase it's relevance -- and revenue.

We put together a full episode of recommendations for interesting things that live at the intersection of culture and business.

Recommendations:

Partying with Australians (1:14) 

Japanese men's magazines like Popeye (that’s a copy up above) and Hail Mary’s (that’s a copy below this blurb) as well as a “personal research” line item in your budget (8:46) 

Khan Academy (15:20) 

Creative Strategy and the Business of Design (20:30) 

Rap music! 26:43  

Every Stevie Wonder album from 1972 - 1980 (33:15)

"The Beneficiary" (41:12) 

SONG OF THE WEEK: Stevie Wonder, “Happy Birthday” aka the only Happy Birthday we respect.

FUTURE OFFICE HOURS HANGS:.

Thursday, July 19, 2019: (Pitchfork Music Festival x Complexcon Chicago weekend kickoff hang) at The Freeze with Chicago-based music writer/world-class human Leor Galil. More details when I have them but pull up if you’re going to be in Chicago!

ICYMI:

The first paid subscriber-only posts will be rolling out starting in August. The podcast episodes will remain free, but the written stuff — including interviews — will be for paid subscribers only. This is your second warning that now’s the time to subscribe if you haven’t yet (and thank you to everyone who has so far!!!).

This is a public episode. Get access to private episodes at officehours.substack.com/subscribe

We put together a full episode of recommendations for interesting things that live at the intersection of culture and business like Japanese men's magazines like Popeye and Hail Mary (8:46), Khan Academy (15:20), books (20:30, 41:12) and every Stevie Wonder album released between 1972 and 1980 (33:15)

We put together a full episode of recommendations for interesting things that live at the intersection of culture and business like Japanese men's magazines like Popeye and Hail Mary (8:46), Khan Academy (15:20), books (20:30, 41:12) and every Stevie Wonder album released between 1972 and 1980 (33:15)

The Office Hours Interview with Darryl “Big Homie Doe” Williams

Former rapper-turned-manager-turned-minority cannabis business owner, Doe has built a house at the intersection of business and culture by now. Currently managing King Louie (one of the most influential rappers of the last 30 years, no hyperbole) and recently moved into the cannabis space.

This week, Illinois became the 11th state to legalize recreational marijuana and with the surge in business, there’s a lot of people who influence culture getting left out in the cold when it comes to profiting from legal weed. Carly tried to tell y’all. Doe is a representation of what a minority-owned cannabis business can look like, one that aims to provide a quality product but still feels cool and not exploitative. It’s a very small lane and one that a lot of businesses in the cannabis industry will struggle to fill in the years to come.

This episode has a LOT of free game for people in music, management, cannabis or people who are looking to break into those industries.

SONG OF THE WEEK: King Louie, “Tesla”.

FUTURE OFFICE HOURS HANGS:

I’ve been asked when I’m going to do another IRL Office Hours hang and I’m happy to report that I have TWO dates on deck, so add these to the calendar if you live in Chicago.

Thursday, July 19 (Pitchfork Music Festival x Complexcon Chicago weekend kickoff hang)

Thursday, August 8th

Updates to come, but add these dates to the calendar if you’re going to be in Chicago.

ICYMI:

The first paid subscriber-only posts will be rolling out starting in August. The podcast episodes will remain free, but the written stuff — including interviews — will be for paid subscribers only. This is your first warning that now’s the time to subscribe if you haven’t yet (and thank you to everyone who has so far!!!).

This is a public episode. Get access to private episodes at officehours.substack.com/subscribe

Darryl "Big Homie Doe" Williams is a multi-faceted creative who currently works as manager to Chicago's King Louie as well as one of the few minorities working in the top levels of the booming cannabis market (39:45). From the first time he met Kanye West to his new partnership in the cannabis space, this is the intersection of business and culture like you've never heard before.

Darryl "Big Homie Doe" Williams is a multi-faceted creative who currently works as manager to Chicago's King Louie as well as one of the few minorities working in the top levels of the booming cannabis market (39:45). From the first time he met Kanye West to his new partnership in the cannabis space, this is the intersection of business and culture like you've never heard before.