Lena Waithe On Chicago’s Best Burger And Her Passion For Mentorship

When you consider Lena Waithe’s public persona, or at least when I do, there are certain things that come to mind:

If you’re going to have a few things about you floating in the ether, those are three very solid picks. The first two are recreations with rabid fanbases and lots of experimentation. But that third one is the kicker. In an era when often-manipulative-sometimes-abusive models of mentorship are being scrutinized, Waithe is genuinely committed to empowering up-and-coming creatives without any expectation of something in return. Her Hillman Grad Mentorship Labs connects mentees from historically marginalized communities with opportunities and guidance from Waithe herself and other creative professionals.

That’s a big undertaking that requires serious partners with deep pockets, the most recent of these being Häagen-Dazs. The ice cream brand’s “That’s Däzs” initiative committed $100,000 to support the work of the Hillman Grad Mentorship Lab, part of a $1.5 million commitment to support “underrepresented creatives and tastemakers” over the next three years.

With a new Waithe-starring season of Master of None on Netflix, a new season of the Waithe-created The Chi about to land on Showtime, and Hillman Grad launching a record company, I caught up with the superstar multi-hyphenate to talk mentorship without strings attached, dealing with critique, and her favorite burger in Chicago.

You did David Chang’s show as a guest, guest judged Top Chef, and you won an Emmy for the incredibly food-focused Master of None — though the show is obviously so much more than that, especially this season. How long has thinking about food at that analytical level been a real passion for you At what point were you like, “Whoa, this is going to be something that I geek out about and I get really into”

Oh, man. Well, I think being from Chicago is a reason why I think I love food and also growing up in my grandmother’s house. She was originally from the south, Arkansas to be exact, and her way of cooking was always, of course, by feel and by gut and by instinct. Never any recipes around. I think that, to me, was always something that I just really got into and then, being a part of Master of None and being around Aziz — you can’t not become a food snob while being around him. He’s going to introduce you to the best restaurants, all those different kinds of things, and so, I ain’t even joking, he’s a person that got me into eating oysters. I wasn’t into that before nor had I really tried it. He was like, “No, this is how to do it.” It was that kind of thing.

His passion inspired you to dive deeper.

For me, that’s also important about food — not being afraid to try new things and not being afraid to try things that you ordinarily would never try. And then you never know you may like it, or you may hate it, but it’s about trying and it’s about having those experiences. For me, this has been a wonderful journey and I’ve grown so much. And also too, I learned how to get a little bit healthier and be more mindful of the things I’m eating and what’s in it and all that kind of stuff. The journey with food has been such a lovely one as I continue to grow as a person and find tastes and things that I like. And it’s tricky because we haven’t been able to travel as much over the past year, but I think that also goes hand in hand with… Whenever I will travel somewhere, I always want to go to the best spots that look like the hole in the wall that the locals really like.

So working with an ice cream brand actually feels like an organic fit, especially with the causes so aligned

It’s been a wonderful thing. Because Häagen-Dazs is all about two creators who knew that ice cream was a bit of a luxury and it’s something that’s been very decadent. And so what they wanted to do was they wanted to make that luxury accessible to everyone. And that’s what was so interesting about their new initiative now, and that they want to donate $1.5 million to many different organizations over the next three years, obviously Hillman Grad Mentorship Lab being one of the first recipients of a 100K, donated to our program in order to pay for teachers and resources and things like that. They’re in line with what we believe, which is following your dreams is a luxury that should be accessible to everyone.

But it’s not. It’s isn’t accessible. Because so many people don’t have the luxury of just quitting their jobs or going to work in a mailroom with no pay for six months and so what that does that do It lends itself to a certain group of people that can do that.

And those people often have the privilege of generational wealth.

Oh yeah, absolutely. Absolutely. And that’s why it made so much sense when Häagen-Dazs reached out because we had already locked the program. And again, it was one of those things, if you build it, people will come up. So they had heard about the program that said, “Hey, we’d like to donate some funds.” And we’re like, “Great! Because we’re paying for everything on our own.” We didn’t ask for any outside funds. We just were like, “We will take the money that we’re making from these other projects and put it into this program,” which we had done already, but then we’ve added to it so that way we can make sure all the teachers are getting paid and the resources are there for people.

Because if you also do want to be a writer, you’re going to have Final Draft. So we did a little partnership with Final Draft and that way they could make the software more accessible. And they gave some of our folks some free software. So it’s all about working with different companies and making sure that our mentees have everything that they need in order to be successful. And also, they’re not paying anything. This is all free and we got five execs, on the exec track, we have 10 people on the writing side and 10 people on the acting side. So it’s just been really beautiful.

And I just met with the mentees the other day, as well as the instructors yesterday, and so we’re in it. We’re in it with these folks. We’re having these conversations. And I’ve also realized, I think people think mentorship is just giving somebody a job. It’s not. It’s about getting to know them, knowing what their dreams are, having real conversations, and what made them want to follow this dream in the first place So I think once you get to know the person that you’ve hired and brought in, that’s when the real mentorship begins. Because then you know who they are as a human being and they’re no longer just a statistic, but they’re somebody with a dream.

I’ve read some interviews with you where it’s so clear that not only are you unafraid of the next generation of people coming through, but you want to champion them. You’re like, “Get into this space and let’s make better stuff. And if that puts you chasing on my heels, then I’ll live with that.” I think that’s an incredibly brave approach.

I appreciate that. And the truth is, a lot of the stuff we do behind the scenes — there are things that I’m doing and working with people that folks will never know because it’s not about that. And I think that’s the true work. That, to me, makes me feel like that’s a… That’s a part of this revolution. That’s a part of this uprising. That’s a part of this protest. It’s about just helping somebody own their strengths. There’s no reason for… Because a lot of times we try to help folks, they think, “Well, what you want in return” And I often say, “I don’t want anything,” but I think we’ve been so trained to not trust anyone, to think that if somebody wants to help you, they want something back. And it’s like, “Nah, you Black, you Brown, you queer, out here just trying to do it, let me be helpful. How can I do that”

And for me, I’m a person that’s very accessible. Somebody hits me, I’ll try to respond or at least point them in the right direction. And it doesn’t matter, I still get swung at on Twitter. People are still like, “Oh, you trying to do this…” And that’s what I try to tell people that really want to do this. When you actually have made it to the place that you think is the promised land, that’s when you’re going to get swung at the most. That’s when you’re going to really go in and remind yourself of why you wanted to do this in the first place. Because there are going to be days when “you made it” where you want to quit. It’s just like, “What am I doing What am I doing this for”

What do you tell people at that point

You got to remind yourself, it’s about following the purpose that was put inside of you and walking in it. Because the thing about walking in your purpose is that it’s a joy and it’s a privilege and it’s a luxury, but what will happen is you’ll have people that’ll celebrate you for it and also there will also be people that will resent you for it. And that just comes with the dinner. And so that’s what I also try to impart on these mentees as well, because they feel like, “If I could just get that movie out, this TV show going, if I could just do this thing…” I think there’s also this idea that people will like me, people will applaud me. Not necessarily.

I always make sure that that’s not what’s driving it for them.

Damn, people are coming to you and they’re saying, “If I could just get to your level of success, I won’t have to be wrestling constant insecurities while staring into the void of a collapsing empire at the end of capitalism.” And you’re like, “But first, you got to just love the art.”

Yeah, you do.

I like that.

And that’s the shit nobody wants to hear. You got to love the process because the truth is people will go, “Oh, I want to be successful. I want to get to where that person is,” but then how many documentaries that we’ve seen about big stars and people that we love and admire and you realize, “Damn, they were going through all that behind the scenes Shit.” And a lot of that is because people do what They put expectations on people. They hold them to a different moral standard. They want them to be perfect. They don’t want them to do anything that they don’t like. So that all comes with it. That all comes with being quote-unquote successful or quote-unquote making it. And that’s where I think a lot of people falter because they start buying into the image that people have created or projected onto them.

While that’s happening, you still got to go make art. And when you put it out, people are going to say, “We don’t like this.” Then, guess what Do it again, yeah. Make it again.

You know what I’m saying

Yeah, put something out. If it fails, put something else out.

That’s the thing. Every time I put something out, you know people are going to try to drag it. That’s just going to be a part of it, but now it’s become so commonplace that I’ve learned to expect it. And so that gives me freedom to do what I want. Because guess what It’s going to happen anyway, my guy, so why not just write and do whatever the fuck you want Because people are going to be mad regardless. And you are always going to have those people that go, “Hey, I like this.” And other people go, “I hate that.”

And guess what They both get to be right.

Yep, we don’t have to argue with critics.

No, they both get to be right. And the only thing that gets tricky with all this social media, sometimes some person can say something that’s not accurate and then people can start to believe that it’s the truth. That’s when I think it really frustrates people because then you’re like, “Well, no, there’s a narrative. That’s not correct that’s being taken.” And that’s really hard.

That’s a little different — when people make character-based assumptions.

But also, guess what You can’t fix that. You can’t fix it. You can’t go to each person and say, “Hey, I’m a good person.” That’s not how this goes. If somebody wants them to understand you, they will. If somebody wants to believe a lie about you, they will. So you got to let people do what they going to do. I’m a big believer in live and let live. If somebody wants to hate me, you have every right to do that. But the tricky part is, but if they’re hating me because of something that isn’t even true, that can be really frustrating. But what are you going to do

Just keep creating, I guess.

Yeah, just keep making shit. You just keep making work. Now imagine having this conversation with a young person that just wanted to be a writer and tell a story. It’s like, “Guess what It’s not that simple.” It’s not. If following one’s dreams were easy, everybody would do it.

You seem deeply committed to the idea of mentorship without expectation of return — which I find very rare and admirable.

How can we use these funds to pour into the communities that need them That’s always my first question. So, that’s what I’m saying. Even if some of my own people are swinging at me, I’m always going to be swinging for them.

Major pivot because we both love Chicago and we both love food — where should people eat in the Chi Small Cheval is my number one rated burger in the country. That’s the one we called out on our “best burger” list back in 2018. Have you ever —

You just took my answer, man.

No way!

You took my answer, yeah. And the tough thing is that I’ve tried to fall back on meat a little bit just because you can’t do too much, but that’s the place I always go to eat. It’s ridiculous. I always go whenever I’m in Chicago and I recommended it actually to some friends, the two amazing ladies who run on Black Market Vintage. They were in Chicago and they said, “Where should we go” And I said, “Au Cheval” and they went and they had a wonderful meal and I was like, “Yes, great.” Because there’s nothing better than giving somebody a really good restaurant recommendation. So that’s what I would say and I’m hoping… Because I haven’t been to Chicago since the pandemic for obvious reasons, but I’m hoping they still are able to deliver or give people that amazing experience with their food.

Wait, so you were going to say Small Cheval or Au Cheval

Au Cheval is how you say it, correct

They have a place called Small Cheval, which is like a little fast-food burger concept that you should try next time.

Oh, I haven’t been there. I haven’t tried that.

That’s the one that’s my favorite burger and it’s right on the loop.

Oh okay. I only knew about Au Cheval.

Yeah, Au Cheval is great, too.

It’s cool that they have that available. That’s actually cool. Because again, getting into Au Cheval is a whole thing. You got to wait an hour. It’s a whole situation. So, they have something else that’s a little bit easier That’s really good to know.

It looks like a 1950s fast food joint, but it’s just a one-off and the burgers are incredible, so check that one the next time you’re in town. What about shooting with Master of None or shooting with David Chang What’s the place from one of those experiences that you tell people about

Oh man, that’s a loaded question. You know what I’ll say this. If we’re in LA, we’re going to My 2 Cents, with Chef Alisa’s [Reynolds] stuff. That’s the restaurant I would tell people.

What makes you love that spot so much

Well, the fact that it’s Black-owned, the chef happens to be Black and queer, which is a bonus. But I just love the fact that you can have a vegan spaghetti that’s amazing, but then you can also have an oxtail taco, which is brilliant. Her mac and cheese is undeniable. The desserts are phenomenal. It’s just the kind of soul food that you have that you just feel like, “Yeah, this is actual soul food because it’s good for my spirit and it also just tastes amazing.”

And also the chef is just phenomenal and she’s a force of her own. She’s amazing. And we hang out. We vibe out and we hang and she’s just the best. So My 2 Cents — whenever somebody’s in LA, they need to pull up.