Issa Rae Reflects on Career Highs, Lows, and the Fear of Losing It All

Kev sits down with Emmy and Golden Globe nominated actress, writer, and producer Issa Rae for a hilarious and honest conversation about mistakes, growth, and resilience. Issa opens up about overspending as a young creator, her fear that success can disappear at any moment, and the importance of continuously investing in herself.

She also reflects on her pilot, I Hate L.A. Dudes, calling it “the most devastating thing ever,” and shares the invaluable lessons it taught her. To wrap things up, Kev confesses that he once auditioned for Insecure and got rejected.

See omnystudio.com/listener for privacy information.

Episode Transcript

Speaker 1 (00:08):
What up, y'all?

Speaker 2 (00:09):
Welcome to Not My Best Moment, a podcast where I
talk to my friends and people I admire about their losses.
Based on the New York Times bestselling book Successful Failure
by Yours Truly, today we have a tremendous titan in
the industry. He said, don't stop me. Let me brag
on you.

Speaker 1 (00:29):
Okay.

Speaker 2 (00:31):
The first thing that I want to say about her,
and I admire her probably more than anybody, to be honest,
because she came from where I am and wanted to go.
You probably know her from Insecure. I remember the day
I became aware of Easter Ray working at Boeing, went
to my homeboy's house. He was like, have you seen
this thing called Awqua Black Girl?

Speaker 1 (00:50):
I said no.

Speaker 2 (00:51):
He sat down, opened his YouTube, I mean his laptop.
We watch it on YouTube and I was like, this
is the best thing I've ever seen in my life.
And I've been a fan. And from that moment, from
Aqua Black Girl to the Choir which is on Tracy
Evans Alright TV.

Speaker 1 (01:07):
I worked with that.

Speaker 2 (01:09):
I was I made it in my life, my first
film I ever made, called The Family Exchange. Easter came
to my house in Recita and was a part of
that very very nice little house in Rosita. Since then,
she's done five seas of Insecure, Rap Shit, Sweet, Live,

(01:31):
Into the Spider Verse, Barbie at least eighteen businesses I've
lost count. She's a partial minority owner of a soccer
team in San Diego. Ladies and gentlemen, we are not
here to talk about any of that, but please welcome
to the show.

Speaker 1 (01:44):
Is Ray.

Speaker 3 (01:45):
Thank you so much, Kevin. It is an honor to
be here.

Speaker 4 (01:48):
Thank you for being in my second directorial debut web series.

Speaker 3 (01:53):
It was us on honor.

Speaker 2 (01:56):
Thank you so much, so Easter. Before we begin, we
are not here to talk about your successes. We will
do that at the very end of the podcast. We're
here to talk about your failures and what you've learned
and how you didn't stop as a result of that.
One thing I would love to start with is awkward
Black Girl to Insecure. That was a process, and you've

(02:19):
spoken pretty much at link about what you learned from there.
But I remember you had some high profile people that
could have been a part of the show that you
changed your mind about things like that. I'm curious about
your frustration if there was any going from YouTube to HBO,
losing amount of creative control. I imagine, how did you

(02:42):
deal with that if that was even the case.

Speaker 4 (02:45):
I my frustrations came solely through the development process like
that that period, once I had the opportunity was working
with Larry, once I thought were making gold, and they
made it seem as though we were. You know, once

(03:06):
we turned in the first outline of the pilot, they
were like, this is in great shape, minimal notes, go
straight to draft and I was like, oh, we're cooking.
We got like really really excited. And then after the
first draft they just were like it wasn't quite right,
and we were still like okay, cool, cool, cool, We'll
take these notes and then like you know, we did
like seven to nine drafts. I always forget the number,

(03:28):
and that's why I started getting frustrated once years started
going by. And you know, people, anytime you have an announcement,
they're always gonna be like, yo.

Speaker 3 (03:35):
What's up with SHO? Show it?

Speaker 4 (03:37):
You said, hey, and Matt like that. Just that's why
I hate announcements to this day, because nothing urged me more.

Speaker 3 (03:45):
Don't ask me about.

Speaker 4 (03:46):
Shit, please, because if I could tell you, it'd be
out you'd see it, you know, so like you don't
see it.

Speaker 3 (03:53):
So why are you asking me about it?

Speaker 4 (03:55):
So that's all that always bothers me, and that's what
started getting me, and that's when I started thinking about
about the internet again, about how like literally I could
just make something right now, I could put it on
the air right now. Why did I go through this process?
But I know why I went through this process because
it's my dream network. And like, no matter what I think,
I still trust these executives who I now know very well.

(04:17):
And yeah, absolutely they I get what they saw and
I'm appreciative of them. But at the time I didn't
know what the hold up was, and I felt that
I was being slowed down.

Speaker 2 (04:27):
Yeah, so give us a frame of reference of like
how long Awkward Black Girl from mine to production or screen?
And how long insecure? Because years when you do YouTube,
you could have it up in a week, two weeks,
like the idea execution is very short, but TV is
not like that, and they warn you about that, but
it never quite feels like that.

Speaker 3 (04:49):
So I also think you're going to be different.

Speaker 4 (04:53):
Well, I mean that was you, because honestly, yeah, you
but me, I'm good, But Acquard Black Girl. I though
about two years before I finally did it, and then
once I did it, you know, I put it out
I think in a week just because I had shot it,
but I just chop I only had one episode in mine.

Speaker 1 (05:13):
Oh really Yeah.

Speaker 3 (05:15):
I was just like I.

Speaker 4 (05:16):
Was thinking about doing it for so long that when
I finally did it, I was like, Ooh, I did it.

Speaker 3 (05:21):
Now we'll just see what happens. And then I don't.

Speaker 4 (05:24):
I wasn't prepared for it to be successful, and then
once it was, I was like then I was playing
ketch up and I was working on it literally every
day for a year because we did twelve episodes.

Speaker 3 (05:35):
And so so.

Speaker 2 (05:36):
Where were you in your life at that time, Like
take us back to that time. What was that like
for you? Like you working a regular job? Are you
in school? I don't know the timeline.

Speaker 3 (05:46):
I was working a regular job.

Speaker 4 (05:47):
So I shot it or I started like working on
it in twenty ten, and I shot it February two
thousand January two thousand eleven. It came out February eleventh,
twenty eleven. So I was working a job. I was
what twenty five, twenty six, and I probably just turned
twenty six, and.

Speaker 3 (06:07):
Yeah, I think I was temping.

Speaker 1 (06:09):
Wow.

Speaker 4 (06:10):
Yeah, I was temping at a at.

Speaker 3 (06:14):
In careers health.

Speaker 4 (06:15):
Yeah, and so nobody, yeah, nobody knew I was doing it,
and I knew that it wouldn't reach them because that
was demographic and so yeah, I was just I had
a little bit of flexibility, but not really because it
was still a nine to five.

Speaker 1 (06:30):
Wow.

Speaker 2 (06:31):
I love that you was working a regular job. I
think I just admire people who I remember when that
was me. I was looking forward to like getting off
or my lunch break or the two days where I
could really do what I wanted to do. Was it
like that for you? Were you're just like at your
job like man to my hours.

Speaker 4 (06:52):
Ah, yes, truly, and then having a little you know,
notebook where you're writing down the things. There's nothing that
gets you more creative than doing something thing you don't
want to do because you're always thinking about like the
shit that I want to do. Oh once I get
to do that, oh just wait, that is always the feeling.
And so like that was it was suffocating. And then

(07:12):
I had a boss that actually whatever you to do work,
so and I was actually doing good work, So it
was just extra frustrating, but you know, the when you're
putting in the extra time to do what you actually
want to do, it doesn't feel it feels so liberating.

Speaker 1 (07:25):
Yeah.

Speaker 2 (07:26):
Yeah, did you ever get to a point of developing process?
I know you talked about going to the internet. Were
you almost like gonna put your arms up and be
like forget HBO, I'm just never mind.

Speaker 4 (07:34):
I thought they were going to be that way to
me once Larry left, once he got the nightly Show.
So I think I automatically was like, well, you know,
if it is, but if they say't no, you know
it is what? It is nice actually talking myself into it,
like they obviously don't see it, so why do they
even waste Why do we waste each other's time? But

(07:55):
they gave me a shot. They were like, no, no, no,
we still want we still want to figure this out.
And that's I still did the thing where I was like,
and I think they felt the same way where I
was just like, you know what, now that he's gone,
let me just kind of take the pieces that I
know work and then let me just put my life
in it. And if they don't take this, then I

(08:16):
don't know what to tell them. Because I don't know
what they want this show to be. And that's the
draft that they ultimately.

Speaker 3 (08:22):
Picked up.

Speaker 4 (08:22):
And but that was also after they had pulled me
aside and been like, hey, what does the show look
like if it's this, because a lot of people don't
know that what I pitched initially was not the insecure
that we saw today. It was more like a set
in the nonprofit world. It was called nonprofit with the
pH and in that she just didn't know what she
was doing. She wanted to be a rapper, but she

(08:44):
worked in this nonprofit space, and she had a friend
named Molly. She had a Daniel was in in that
version of the pilot, but they were like ancillary characters
and they and Molly was still based off of my friend.
But they pulled me to the side, you know, after
Larry left, and they were like, what does the show
look like if it is more about Issa and Molly?
And I was like, oh, say, let's and so that

(09:05):
that was great development on their part.

Speaker 2 (09:07):
Wow, that's so this is so interesting because the idea
was just one episode. Your pitch was a totally different show,
and all the audience knows is what we saw. We
only see what is there and nobody knows what's going on.
Did you have other things going when you're in development
for Insecure or was it just Insecure?

Speaker 4 (09:29):
Yeah, because it was taking so long, and this is
one of my not my best moments because it was
taking so long. And again I was affected by the Hey,
what's going on?

Speaker 3 (09:40):
What happened?

Speaker 4 (09:40):
You know, cause there are those people in my mind,
I'm like, you're just rooting for me to feel You
want me to say it didn't work out because that
makes you feel better about all the failures that you have.

Speaker 3 (09:50):
Like I just hate that.

Speaker 4 (09:51):
And so I was like, I need to feel active
and I don't want to forget my Internet roots.

Speaker 3 (09:56):
So that's when I.

Speaker 4 (09:58):
I think that was around the time time that I
met Serena and we were doing like digital workshops, and
I think I did alright TV the choir while Insecure
was happening too. So all of that is happening within development.
But I decided to take a bet in terms of
trying to make the awkward black girl model, which I

(10:21):
hadn't fulfilled yet technically, but like wanting to create something online,
get an audience excited about it, and then get you know,
then have networks coming at our door. So I had
the idea to do these independent pilots and was supposed
to get funding for them. Thought I was going to
get funding for them, but ended up accidentally paying for

(10:42):
them all myself. And these were fifty thousand dollars pilots each,
and so like that was my that was like kind
of my book advance. That was all I had. But
I didn't expect to be paying for it. But I
just didn't think about it. I didn't think it through properly,
and I relied on the wrong people to fund.

Speaker 2 (11:00):
So you the wrong people like business partners. Yeah, okay,
so you had one hundred and fifty grand that wasn't
allotted to make. Boy, you talk about we were closer
in Kindred spiras. And then I even realized that you
shouldn't leave creatives along with our own money. You shouldn't
leave us alone because we will spend it all because

(11:24):
something gotta work.

Speaker 3 (11:25):
Yeah, yeah, you've bet on yourself literally.

Speaker 2 (11:29):
Like if it weren't from Melissa, I might be homeless
or a billionaire more likely to be homeless because I
have done that.

Speaker 1 (11:38):
So how bad was it for you?

Speaker 2 (11:41):
When you really your eyes just got big it was.

Speaker 4 (11:44):
It was the stupidest thing I've ever done because it
was literally all the money I literally literally all the
money I'd ever made in my life until that point.
And yeah, my business manager had called me while we
were in the middle of the first pilot and was
just like, what do you sis?

Speaker 3 (11:59):
What did you do? What are you doing?

Speaker 4 (12:02):
And I was like, oh, well, I'm no, it's and
I just didn't know what to say. But I because
these were writers that had their opportunity to make pilots,
I already told them it was gonna happen. We were
in pre production, we had hired these directors, everybody was,
we had cast, everybody was hyped to be doing it.
I couldn't be like psych, I don't have the money

(12:22):
to do this. So I just had to figure it out.
And I just I didn't know what to do. So
then at that point he was he was helpful and
was just like, we'll figure this out, but you know,
no more eat it out. You can't like you gotta
and I did. I had to just start making like
it was just it was.

Speaker 3 (12:41):
It was bad.

Speaker 1 (12:42):
So did any of those pilots become anything or they all.

Speaker 4 (12:47):
They they got people jobs, so one was like, obviously
Serita Singleton, that was her pilot and she ended up
writing on Insecure. Brittany Nichols was one and obviously she's
like a producer on abbed La Mentory. They ended up
being calling cards but nothing ended up getting picked up.
And Sean Boxy was another writer who was amazing. He

(13:09):
got staffed on the show, but he passed from cancer.

Speaker 3 (13:12):
Rip to him.

Speaker 4 (13:13):
He was extremely, extremely talented, So it was more like
a discovery tool.

Speaker 3 (13:17):
But I needed the money now. I needed it to
pay off.

Speaker 1 (13:23):
He's hungry.

Speaker 4 (13:26):
We went to all that digital to like that was
when I think you were there. We were trying to
get so Jada picked up there. It was just like
we people and a lot of people were like, hey,
these are great but and even the concept is great,
but we need time. And that's my issue is I
was like, well, I need this to happen now because
I'm already spending my time on this HBO pilot and

(13:47):
that's not going I don't need something that's gonna take time.

Speaker 3 (13:50):
I want it now.

Speaker 1 (13:52):
Yeah, what did you learn from that experience?

Speaker 2 (13:55):
Because even at your level, you can technically make the
same mistake, especially if you actually have more income, you
can fall into the same trap. Have you been tempted
to fall into the same trap? Are you smarter now?

Speaker 3 (14:07):
You ain't?

Speaker 4 (14:10):
I learned I've never spent all my money again. But no,
I'm in a position right now where I'm like, I
still feel the same, and I would do it again.

Speaker 3 (14:19):
I would just not.

Speaker 4 (14:20):
What I've learned is don't do all your money. But
what I invest in myself again? Yeah, because I know
more now and now I have more connections and there's
still more outlets, so I think I have more of
the business sense.

Speaker 1 (14:34):
Yeah now, so.

Speaker 3 (14:36):
Yeah, I I would do it again.

Speaker 1 (14:38):
Just let me ask you.

Speaker 2 (14:39):
This is totally random, but I'm just curious. Do you
ever have the thought of, like, what if this all
goes away?

Speaker 3 (14:46):
Every day? Yes? Do you not?

Speaker 1 (14:50):
I do.

Speaker 2 (14:51):
That's why I was curious, like, is it ever gonna
go Is that feeling ever gonna go away?

Speaker 1 (14:55):
For me? But if you still feel that way?

Speaker 4 (14:58):
No, Yeah, I'm like I say that I'm I'm rich
right now, and that is great, but that's a it's
a very current thing. So yeah, that is like I
think about that constantly because you just I know that
I can save now and I that was my issue

(15:18):
before it is like it was just really hard to
save money. But yes, this can all go away immediately,
and it could go away for some shit that we
were just talking about because the clip surfaces or people aside,
like they don't fuck with you anymore, and there's only
like I pride myself on being able to create on
a dime. And I'm sure you asked me the question.

(15:38):
I'm sure you would bet on yourself time and TI
make your own money one thousand like things change when
nobody wants to watch you. And I'm still at the
mercy of that.

Speaker 1 (15:46):
That is so true.

Speaker 2 (15:48):
I actually have that fear sometimes, even like a paralyzing fear.
One thing I work through is just like I gotta live, man,
I can't. You don't even know what is wrong. I
I just went through this a little bit with this
this Dinny King din A King's episode. People were frustrated

(16:08):
with me for who the guests were. They were like,
how did you? How dare you? And I'm like, bro,
I I didn't know who was on there until the
day before. Oh really, I didn't know, Like I just
got asked Kirk asked me to do and I was
like for sure, and because I had to promote CHURCHI
and the book and hospital. I'm I'm you know, I'm
not getting the opportunity to go on Jimmy Kimmel and

(16:29):
you know, Jimmy Fallon. So I'm like, yes, anything that
gives me a chance because I'm still fighting for season
two in season three and trying to get the book sold.
Like I'm I'm so I'm saying yes. When I see
the call sheet, I'm like a man, they gonna they're
gonna be mad at me.

Speaker 1 (16:43):
But it's like I don't I'm stuck either way.

Speaker 2 (16:47):
Like if I don't do it now, my partners at
the network are like, yeah, how are you not promoting
the show?

Speaker 1 (16:52):
And people you know.

Speaker 3 (16:56):
Dropping out?

Speaker 2 (16:56):
And and that's my other thing as a creator. My name,
like you pull out the day before the day with
the call she like, And I'm not even blaming them,
like I just standard I just knew, Like you get
the call sheet between eight and ten the night before.
That's you know, they didn't do anything wrong. I just
had a feeling that I was like, oh man, and
then there were some stuff I just didn't know. But
I say all that to say is my fear is

(17:17):
like one wrong tweet or something out of context or
in that case of that video, just the way my
face was looking, you know, like goes viral. They had
twelve cameras in there. In my head, I'm like, I
hope they not singling me out. I just hope not
only were they singling me out, they had a slider
they rack focused to me. I said, oh, they had

(17:37):
a special day. You set that shot up on a
scripture show. You kuldn't have time that better for real,
So let me ask I mentioned that this is anotherhing
I want to ask you. I follow you for a
long time. You used to be way more active on

(17:57):
social media, and I saw it starting with your book,
like somebody had taken a piece of your book out
of context. Yeah, and then I started slowly seeing you
become less and less and less and less active. Is like,
do you feel that way?

Speaker 3 (18:12):
Is?

Speaker 2 (18:13):
Was that on purpose? Was that like to protect the
brand or to protect your mental health?

Speaker 3 (18:18):
Yeah, all of the above.

Speaker 4 (18:19):
I actually started deleting tweets or or like as soon
as I got as the pilot got picked up. Finally
we shot it, like literally the week after we shot.

Speaker 3 (18:29):
It, I was like, oh, bitch, Nope.

Speaker 4 (18:32):
Nope, And I got that little program and started deleting
in the writer's room every day ten thousand tweets because
I had a lot, and I was like, I'm not
going through this, I'm not getting caught up.

Speaker 3 (18:42):
So that was before the show came up, and I
was like, great.

Speaker 4 (18:45):
Cool, because I was also out there where I was like,
and I didn't have any of these.

Speaker 3 (18:49):
Let's be here like homophone people, homophobic.

Speaker 4 (18:51):
Tweets, and people were just digging up and I was like,
why would you even say that? But I bought shit
like during award shows where I was just talking about
shit that people I would eventually meet, and I was like,
I don't want no smoke.

Speaker 3 (19:02):
This is all in fun. I don't want anything out
of context. And so yeah.

Speaker 4 (19:06):
Then then you know, when you have something successful, you uh,
you're people hear from you more and they look they
look for you more, and so you kind of ride
that wave of just like, oh, this is fun, people
are responding to me. I have stuff to say, and
then it gets to the people take your things out
of context. And Twitter was already just becoming annoying to me,

(19:28):
and then I just felt like not even in an
arrogant way, but like just people having access to your thoughts,
and I would get irritated with like why is this
person expressing this?

Speaker 3 (19:40):
And why am I expressing this? What is this for?
What am I looking for other people's validation? And then
I get.

Speaker 4 (19:46):
Upset when people engage in a conversation with me, so
like what am I what is this for?

Speaker 3 (19:52):
I don't now.

Speaker 4 (19:53):
I only want it to be of just information. And
also I think about my my faves. I didn't know
everything about them, yeah, and they stayed my face for
that reason because I'm like, you're giving me just enough
and I want some more. Yeah, And I just I'm like,
what am I giving?

Speaker 3 (20:10):
What is this doing for me? Nothing?

Speaker 2 (20:12):
I love that and you basically just announcing the things
that you worked on. So I want to talk about insecure,
I feel like and correct me if I'm wrong. I
feel like you've talked about it as if it fulfilled
what you wanted, like you didn't necessarily want seven eight
seasons like five was good, but sweet life, rap shit,
everything didn't get what you might have wanted. How did

(20:34):
you deal with Did it hurt when you you found
out these shows were getting canceled? Like what was going through?

Speaker 1 (20:38):
Your mind.

Speaker 3 (20:39):
Yeah, I mean all of rap shit. I was telling
cast and crew.

Speaker 4 (20:43):
I was like, hey, let's not get used to this, guys, like,
you know, really might not get a season two.

Speaker 3 (20:50):
And then even during.

Speaker 4 (20:50):
Season two, you know, I love our cast, you know,
my feeling themselves a little bit like you know, and
I was like, guys, like, be on time, let's do that, like,
let's just please because we might not get a season three.
We know that we stepped it up I know for
a fact we stepped it up season two. Season one
was a struggle and finding the show, and that's when

(21:12):
I was like, pilots and development are good because I
just felt like we just needed more development and we
found our footing by the end of season one. But
by season two we felt like we really knew what
the show was. And even still, I was like, everybody's
giving their best performances. You guys are killing it, but
like nothing's guaranteed. So around that time also, especially once

(21:35):
I saw like that things were getting canceled.

Speaker 3 (21:38):
I mean, the writer's strike was happening, and.

Speaker 4 (21:42):
What was our other big thing, pandemic Pandemic, I felt like, well,
pandemic was out before all of this, but I think, oh,
it's obviously.

Speaker 3 (21:49):
The writers and the actors strike.

Speaker 4 (21:51):
So I was just like, this is we're gonna be
on the front lines of this, and we're gonna be different.
The first ones to get canceled black shows period, and
I couldn't like assume that. Oh and then Warner Brothers
Discovery that's what the merging happened. Oh yeah, and that
was like show budgets are going to go down. So
I had an inkling that we were going to be

(22:12):
on the chopping block, but I still had hope that
because our audience seemed to be growing and more people
started learning about the show, that we'd be given the
grace that we were given with Insecure, because Insecure wasn't
a ratings juggernaut, but our show was just really also expensive,
which I didn't know, and it just you know, wasn't.

Speaker 3 (22:31):
Worth it for them to keep continuing. So that hell
of hurt.

Speaker 4 (22:35):
And I wasn't denial because I was like, Okay, well,
sure we can shop it somewhere else, and HBO was
great about yet, like, yeah, you can try to take
this somewhere else.

Speaker 3 (22:42):
We're good. But it just couldn't.

Speaker 4 (22:44):
We couldn't get it picked up anywhere else, and that
hurt because I felt like I had let the cast down,
I had let the writers down all that the end,
it was just going to be hard moving forward, and
that was a lot of people's first acting jobs that
really sucked. And same with Sweet Life, like I love
that cast. I was a fan of that show, of

(23:05):
watching that crew, and that I know for them to
go back to like regular life was going to be
really hard.

Speaker 1 (23:12):
Hey guys, taking a quick commercial break. We'll be right back.

Speaker 2 (23:37):
Do you carry that burden or even some like version
of survivor's guilt, because like you personally continue on in success,
but everything.

Speaker 1 (23:45):
You touch doesn't make everybody insecure.

Speaker 2 (23:48):
Had a really high success raised like almost like a
living color level of like especially behind the camera, Like
a lot of people got their first and went on
to success, but everything not everybody insecure and not everything.
But do you feel like man, like you wish there
was more you could do, but that like guilt just
sits with you.

Speaker 4 (24:08):
The guilt sits with me, and not even because I don't,
I still feel like, you know, I've been stunned by
a lot of the changes. I feel like everybody in
the industry has been affected in some way, but I
feel the guilt that, yeah, that I couldn't fight hard
enough to have a result because I fought, and to
this day, like to this day, I still try to

(24:29):
find ways to either like for Sweet Life, I don't
think I'll ever let that go, but like for rap shit,
just trying to make sure that the cast is good
and that people are considering them for things, or and
the writers and the like.

Speaker 3 (24:43):
But it's it sucks.

Speaker 4 (24:44):
I feel extremely guilty, and even seeing cast members or
writers again, I always have to let them know, like
I'm thinking about them.

Speaker 2 (24:51):
Yeah, that's that's I I we should be closer friends.
This is I'm just like the common of that. And
then you you also feel like sometimes to me, I'm
not putting this on you. Then sometimes you feel like
you work so hard for others, you want to make
sure people are good, and you don't really get much
out of it except giving people jobs. And then you

(25:12):
start to be like, well, dang it, I'm going crazy.
I don't see my wife or my kids, the dog
don't recognize me.

Speaker 1 (25:18):
But people are working.

Speaker 2 (25:19):
So it's like the balance of doing that versus The
worst part is when you know you can't control it.
And you wish you could, and the network is like
knowing these shows. You know, when it's a YouTube show,
it's I could afford it, But at this level you
can't afford to like pay that money that I can't
I don't have that kind of money to like pay
all those people that there's a lot of money and

(25:41):
it goes by, you know, you no production budget, it's
a lot of money, and it's gone quickly, so fast.
You're like I used to never understand people like, oh,
a million dollars ain't no money. I'm like, when I
was doing stuff for free, what do you mean A
million dollars ain't no money. But then when you get
to union rates and you like, dangn a million dollars

(26:02):
is really gone. In two you run payroll three times
and pay insurance and all this stuff, You're like, dang,
that's really gone, and none of it went to you.
You're just like a pass through account.

Speaker 4 (26:14):
Yeah, you don't even get to put a lot of
it on the screen when a million dollars like And
that is the most frustrating part, because yeah, it feels
like you should be able to And I used to
lament that part of the part of My transition even
from from awkward black Girl to insecure was that frustration
of just like why aren't we just putting the camera
on the car, like just put and let's drive, Like

(26:35):
why don't get a process trailer? And now that's six
hours that we wasted, Like what are we doing here?

Speaker 3 (26:41):
But I didn't understand the union rules.

Speaker 4 (26:43):
I didn't understand cru safety and actor safety in.

Speaker 3 (26:46):
The same way. And that was a hard lesson.

Speaker 2 (26:49):
Yeah, I agree so so much. I feel like there's
getting too much about me. We're going to back up.

Speaker 1 (26:56):
I'm cus I.

Speaker 4 (26:58):
Had questions, honestly, even about funding Churchy. Is that is
that all you right now? Or is that you're so.

Speaker 1 (27:04):
The first season was all me?

Speaker 3 (27:06):
Is that what you sent all your money on?

Speaker 1 (27:08):
Lisa marriage? Be hard?

Speaker 2 (27:13):
Melissa told me Lisa she told me two things, and
I was so gung ho about it. She was like, One,
you're gonna go over budget. She was like, Kevin, You've
done this your whole you worked at all Death, you
worked at awesomeess Win have things not gone over budget?
And two, because it's yours, You're really gonna go over

(27:35):
budget because you it's your thing, and we were doing
getting COVID. She was like, keV, oh my god, all
these fees. Like we had a setup of like get
your free tests, turn it in, you know, do all
that stuff. People wouldn't do it. So we had to
have the doctor come and the doctor's like two hundred

(27:55):
dollars a test per person, just COVID. She's like, you're
gonna go up. Biggest mistake ever that She absolutely stopped
me in my tracks. There was a production.

Speaker 1 (28:07):
Financing.

Speaker 2 (28:08):
She was like, we should cover that, like we made
like we should keep it in house, we should pay
people ourselves. It's a lot of money. We should handle it.
And I was like, no, like we're gonna trust the people.

Speaker 3 (28:23):
Damn, damn, damn, damn damn.

Speaker 2 (28:27):
To this day, she's never even told told me I
told you so, And she doesn't have to. It's always
there though, and she's not even playing the car, but
I told you so is allways there. She told me Isa,
she told me, and I didn't listen. And when that

(28:50):
money was not accounted for, I just couldn't believe it
happened to me. I sat there and I said, dang,
that money really gone?

Speaker 4 (29:01):
Did she was she in the room with you when
you like when did she find out she was right?

Speaker 3 (29:07):
Was she experiencing it?

Speaker 2 (29:08):
We experienced it together and I could see in her
eyes she was like, this is exactly what I said
could happen.

Speaker 3 (29:19):
But she saw your pain. It's okay.

Speaker 4 (29:21):
You don't need an eye told you so when you
can see the pain, and because that's all you want, Like,
I just want to see that you're suffering with me,
and that I can tell that you know that I know,
and that's you don't need that I told yourself.

Speaker 2 (29:36):
She saw me like it hit me like a ton
of bricks and I was like, oh, we're beat.

Speaker 1 (29:42):
Like that money is and it was a lot. Like
people don't understand.

Speaker 2 (29:46):
It took years of saving for me to be able
to finance that, years of brand deals, years of spectrum commercials,
years of touring. I saved that for years. And when
I tell you that production was nineteen days, that money
was gone in less than that. And I was like,
and then bills kept coming up after COVID, God ain't

(30:09):
been paid, These actors haven't been paid. I've already given
the money to pay these people. They're not paid. Now
not only is there not paid, I have to pay
them basically again and I remember when I realized it
was a moral thing because I was talking to SAG
and they were like, technically, keV you because you gave.

Speaker 1 (30:30):
The money to the people to pay them, you're not
on the hook.

Speaker 3 (30:33):
Gys crazy.

Speaker 2 (30:34):
Really, They were like, you really don't have to do this,
And I was like, but I've been there. I've been
at the point where I need twenty five dollars and
I got to have it and I don't care what
I need the twenty five and I'm counting on it
and I'm checking the mail, and I knew that I
couldn't live with myself if I knew somebody was like,

(30:57):
keV owe me twenty five dollars ninety you know some
of them are like just an extra ninety eight dollars
per day they came and did their work. I cannot
just I can't sleep at night knowing you trusted me
because and then the other part is if I'm gonna
get drug on top of that, like one, I can't
sleep with it too. They gonna come after me. But

(31:18):
more than any of that, I can't sleep knowing I
owe you bread and you did your work. So if
I got to go on.

Speaker 3 (31:23):
I know I know you. I know I owe you,
and I.

Speaker 1 (31:27):
Know I owe you that money, and I can't. I
didn't do it.

Speaker 2 (31:32):
When I worked at the bank, people at the bank
way back in Washington. I write about this a lot
in my book. People were getting over on people and
I was like, I live in this city. I just
I don't want nobody to hit me in the back
of the head with a brick because I tricked them,
like I can't sleep dollars man, But you know we're
starving in la people need every time. So I learned

(31:53):
that lesson, and I definitely haven't haven't made that exact
mistake again one COVID.

Speaker 4 (32:00):
You said you did it in COVID, Like weird. My
shoulders are still tense because that, like everything was double
during that time. But I also get one of the
instinct to like make some shit because I had that.
I was like, I want to make something and I'm
just stuck here.

Speaker 2 (32:16):
And by the grace of God, I'm very thankful it
started like a thing of like I wouldn't be having
all these things if I didn't do it. But I
wish I would have learned that lesson a different way.
I do want to ask you about La dudes.

Speaker 3 (32:31):
Oh man.

Speaker 2 (32:31):
Yeah, So as a fan, I'm looking at the trades
deadline Isa ray Seanna Rhimes comes, this show is coming,
and I didn't, you know, not close enough to be
like what's up with that? But then I remember not
having that like what is that like to like what
is that even to like get to the point of

(32:52):
that article, you know, just walk us through that if
you can, or as much of it as you can.

Speaker 3 (32:58):
Yeah, that was.

Speaker 4 (33:00):
Like the most devastating thing ever because it felt like
I had the biggest and best opportunity for me at
that time. It was like, you know, I followed Shonda
Rhime's career, I'm you know, live tweeting, and to be
able to have that opportunity to create her first comedy
show and work developed directly with the development team, Like,

(33:22):
I just felt like this was the perfect next step.
And what I always say during that time was just
I was so eager to please at that time.

Speaker 3 (33:30):
That I just didn't have a voice. I didn't know.

Speaker 4 (33:33):
I knew that I had the opportunity, but I didn't
know When I pitched I Hate La Suites, it was
you know, it was it was in one of those
general meetings for anybody who's not in the industry, you
get put on. Your representation will take you to and
be like go meet with this person, go meet with
this production.

Speaker 3 (33:53):
And there's no purpose, which I hate.

Speaker 4 (33:55):
It's like generally talking and I'm like, I don't bring
a pitch and they're like, no, don't, I just want
to get to know you. But this was one of
the rare times where they asked to meet with me,
and I asked like, should I have ideas ready? And
they were like no, no, no, it's just they want
to meet you. So I was like okay, and so
when they sat me down, they were kind of like
we got into the small talk and they were just like, so,

(34:16):
what do you got what ideas? And I was like,
oh no, what my representative was told me you wanted
to know me, and that's usually right, and so I
was just I had luckily just shot the first teaser
for the next web series I was going to do,
called I Hate La Dudes, until that was in my head,
and I talked about what I wanted that show to be,

(34:36):
and as soon as I said the title, they laughed,
and so I was like, oh, this is great. And
so they were like, well, what do you think the
show is? And I was like, I don't know, maybe
it's this and this is my encounter and this is
my experience dating in LA and they were like, let's
do it. So that was the extent of me thinking
about it and so developing it. I wasn't writing the
show with me and mine. I just wanted to. I
was thinking about a network sitcom and you know, oh,

(35:00):
just didn't know what I wanted to say and it
showed in the writing. And I also didn't know how
to take notes during that time. So whatever Shondaaland was
telling me, because they were the best, and they were like,
I'll go to that office like every week and they
would just be really hands on with me. But I
would incorporate that, and then ABC Studios and ABC Network

(35:22):
will give me notes and you'd think that they're on
the same page, but there are completely different people with
completely different thoughts, and sometimes they'd be conflicting and I
was just like okay, yeah, yeah, oh do that yeah.

Speaker 3 (35:35):
And I didn't.

Speaker 4 (35:35):
Understand, like these aren't prescriptive. This is just they're basically saying, bitch,
we don't understand, so like, what is this, what are
you trying to say, and so what I ended up
turning in was just kind of mush, and I was
so ashamed when it got passed on because we sold
it in the room, like we sold it in the room,
which I also didn't understand. Oh they bought it because

(35:56):
this is Shanda. It wasn't a testament to my talent
or my idea. It's like China has an overall deal there.
But I was still like, oh, they like this, they
liked this idea, but yeah, the pilot just wasn't saying
anything and it wasn't special, and I didn't Yeah, it
just wasn't great, but they still were like, you know,

(36:17):
we want to figure out your next show. And I
was just so grateful, but I was just too embarrassed.
I was like, they just saying that shit to be nice.
So I'm glad that there are no announcements that like,
mostly they're no announcement that that shit's not going forward.

Speaker 3 (36:31):
But I know people wondered one.

Speaker 2 (36:34):
I want you to go back to what you said,
because I think that is really important. You were such
a people pleased that you didn't have a voice expound
on that, because I think that's really important observation.

Speaker 4 (36:47):
I forgot that they wanted to work with me because
I'm me. I forgot that, and you do forget that
because you're in the presence of someone and people who
have made successful television. I wanted to deferral. I deferred
to them. I was deferential if just like they know

(37:07):
what they're talking about. I don't know what they're talking about.
I don't know what I'm talking about. So they got
to know best and saying with ABC and in the networks,
I'm like, they know what they're talking about. They make
TV all the time, so surely, like I've never done
this before, Surely I don't have the right to express
I think.

Speaker 3 (37:24):
This is dumb or I wouldn't normally do that, Like
how dare Why would I do that? Right?

Speaker 4 (37:30):
And so in the next opportunity, I think that's when
I realized, like, oh, they want my voice. They want
me to be as loud as possible with what I
want to say, they want me to know what I
want to say. That they tired me because what I said,
an awkward black girl was so loud and so distinct
and so unique. So it just took me a while
to register that. And generally I talked about this in

(37:53):
my own book was like I generally separate myself from
any success that I have. I always think that it's
the resis of the great casting I did or the
other someone else is why something is successful.

Speaker 3 (38:06):
It can't be me. And I know people call that.

Speaker 4 (38:08):
Imposter, certain syndrome or whatever it is, but it took
me a while to equate myself with my success.

Speaker 2 (38:17):
This is, man, I'm just like, this is like the
way you do your mirror shots.

Speaker 1 (38:24):
It's just like I'm maybe I'm not crazy because.

Speaker 2 (38:30):
Like, man, you're saying that, I'm just I just realized
that as you were saying.

Speaker 3 (38:35):
That that you do the same thing.

Speaker 2 (38:37):
And my wife be like, keV, you are and my
friends and I'd be like, yeah, y'all don't know man
so much.

Speaker 3 (38:44):
You guys are my friends being nice?

Speaker 2 (38:47):
Are just being nice? They could do this with anybody
they why, you know. And it's like I don't count
anything that I've done, And I always never think I
am where I belong, like I'm supposed to be there
with the people. I just be like, this is crazy, yeah,
which sometimes gets me in trouble because I'd be like,
when you used to be on tour, like you're talking

(39:09):
or whatever. Back in the day, you were just one
of the people, and then all of a sudden people
look at you different. Now you can say the exact
same thing as a million other people, and even a
less version, and you on the shade room or you
on you know whatever the summer jam billboard is. Yeah,
but that's so interesting, and that's this is literally why
I wrote the book, not to even plug it. But

(39:30):
it's like you need your I hate la Dude's failure
to become your next time where you're like next time,
I'm actually gonna say, because either way, if it's going
to get passed on, I'd rather get passed on with
me saying what I want and yeah, trying to appease
other people. But you need to learn, like you have
to learn that you don't that's.

Speaker 4 (39:50):
Lucky enough to get a next time too, which is
also like I thought that was I thought it was
over for me. I was like I blew the one bitch,
because how could all those elements come together? Like I
wanted to work with this person. I admired this person.
They called me and they accepted like the second idea
that I pitched, like this is meant to be, and

(40:10):
so when it doesn't happen, it feels like, how will
anything ever go right in this way?

Speaker 2 (40:16):
For me?

Speaker 1 (40:16):
Again, isn't that so strange?

Speaker 2 (40:19):
How in your mind you were that is the actual
thing you feel, and it makes perfect sense.

Speaker 1 (40:24):
And then looking back, you're like, I had no idea
I was gonna and.

Speaker 4 (40:28):
I'm glad that it didn't happen. Also like I'm glad
no shade whatsoever. But I'm like, oh, I wasn't a
network TV voice at that time. I didn't I need
a tars I need it, sex, I needed like I
needed all these things to tell my story.

Speaker 3 (40:42):
It would have been.

Speaker 4 (40:43):
And again I didn't write that for myself. I was
writing it was someone else in mind because I was like, oh,
they're not asking me to write this for the just
I don't know. Again, same same shit. So yeah, it
was a blessing that it didn't happen.

Speaker 1 (40:56):
Did you How long did it take for you to
realize it was a blessing?

Speaker 3 (41:00):
Uh?

Speaker 4 (41:00):
Like last month, like honestly I want honestly and reflecting
and writing the book. That's when I was like, oh, yeah,
what do you mean? Like this is interesting because I
don't really look back unless It's really one of those
embarrassing moments.

Speaker 1 (41:16):
Jesus Christ. Wait, what is what is your birthday?

Speaker 3 (41:21):
Oh?

Speaker 1 (41:21):
Are you a tourists? Yeah?

Speaker 4 (41:23):
Rounded, yes, you're that's arth sign right yeah, yeah, so
that's why we we just are sign as well capricorn.

Speaker 2 (41:30):
Se So, so do you consider yourself successful right now?

Speaker 3 (41:37):
Uh?

Speaker 4 (41:41):
I know that I appear successful to other people, But
right now, no, I feel really stagnant because and that's
literal because a lot of the ship that I've been
working on, Uh, because I don't only feel successful when
my shit is on the ear. I don't have shit
on the air right now, really, yeah, because that's my
that's my love. Like I can have the eighteen businesses

(42:04):
that you said, and those are like great passion projects,
but like what I do and what I get excited
about isn't happening right now.

Speaker 3 (42:12):
So no, I don't feel successful. Yeah I'm optimistic. Yeah
I'm not successful right now.

Speaker 1 (42:41):
I know the answer.

Speaker 2 (42:42):
But the stuff you've done, once it's over and aired,
and even though it's technically airing, if it's not a
brand new show with new episodes or movie, once it's
out of theaters and off the air, you're just like
I am nothing again.

Speaker 5 (42:56):
Yeah I have nothing, but yes that is I haven't
been worsed to.

Speaker 3 (43:08):
But that's exactly nothing again.

Speaker 4 (43:14):
Crazy, it's so real, exactly like that. I'm going to
when this comes out, take that part, and that's what
that's me.

Speaker 1 (43:26):
I love. I think that is.

Speaker 2 (43:28):
I can see how that can be a negative, but
I do see like that's a creative hunger part of
you that's like never gonna be satisfied. That's low key
why I still make Instagram videos. And that's why I
love stand up because I'm developing stuff that's in the
year's process and I'm just like, I will lose my
mind because you can do all of this and and

(43:49):
and eventually it just gets passed on. Luckily, some of
the stuff I'm developing hasn't had any articles, And I
used to like campaign for articles like yo, But now
that that stuff what would have been an art that
show went away, I'd be like, all right, Actually, maybe
I'm only gonna talk about announcements of things that are
actually made.

Speaker 3 (44:06):
Happening or they're done.

Speaker 4 (44:08):
But I can that about you because like again I
am mean the fact that you literally own your shit,
but you have the stand up quality and you can
just you can have a show anytime and an audience
will come to that anytime. And that's such a skill,
Like it's yeah, and but I have that fear like
that going on the stage is just a completely different beast.
But you get to constantly build your audience, publish, you're doing,

(44:32):
work on your craft, and have that immediate feedback reaction
at every time, and you can always make money from it.
You can always fall back on it.

Speaker 1 (44:41):
I'm so grateful.

Speaker 2 (44:42):
And one thing my dad taught me, and the one
thing I have listened to him and my wife about
is living beneath my means. I could go for some
years of people hating me and be okay because I
a man.

Speaker 1 (44:57):
I don't do a whole munch of nothing but eat
in travel.

Speaker 3 (45:00):
But what about your kids? The kids part?

Speaker 1 (45:03):
What about them?

Speaker 2 (45:06):
I got you out of you alive, man, you ain't
gonna die.

Speaker 4 (45:11):
I guess you did say that now, But there was
no part of you early on that was like I
can't oh.

Speaker 2 (45:17):
Early on, when we first moved to La Easter, I
was like, I have ruined them. I have ruined Melissa,
say Joe, there's no like what if I and we
rented our house out and quit our jobs at Boring.
There was no way, like, we could not go back,
and I didn't. I knew how volatile this business was,

(45:37):
but I realized how quickly it ends and people move on.
I used to tell the story about Tracy Evans. She
is the reason we all right, TV is the reason
we're I abuld have moved to LA. She did so
much for us, but when that closed, she was like,
all right, guys, she's on to her next thing. And
I'm like, I don't have no more money. Though she
she was like, bro. I got like, I'm not blaming her.

(45:59):
I just did no because we had dinner at your house.
She was like, yeah, man, but this is over with.
And I'm like, but I don't have no money, though,
what am I going to do? And I had to learn,
like them people, once it's over, man, everybody goes to
their next Every once CHURCHI raps that everybody on that

(46:23):
set has another gig to go to or they're trying
to get their next gig, and they will come back
if you can come back. But like I didn't have that.
I would still only work day jobs up until that point.
So I'm like, we had always shifted from a thing
to a thing to a thing and then that last
thing is over. And she tried like she she strung
us like not strung us alone. That's she paid us

(46:43):
for as long as she possibly could. And it's not
her responsibility to take care of our families. That was
another lesson I had to learn, like people got to
take care of them and theirs. They can't do things
just so you can eat. But we was in you know,
we our rent here was double what our mortgage was.
And my kids were in private school in Washington. Here
they were in public school, and they were like I

(47:04):
remember my oldest went from like a class of eight
people to thirty five.

Speaker 1 (47:08):
L a u s D.

Speaker 2 (47:09):
In the first day school, somebody grabbed a kid. Another
kid grabbed the kid and threw me against the lockers
and he was like, can we go back to our
old school please, or a school.

Speaker 1 (47:18):
Like that at school? And I was like, no, man,
you l a u s D. Now it's real, it's now.

Speaker 3 (47:26):
So yeah.

Speaker 2 (47:27):
I had such a fear and I really don't like
I had to make sure they're squared away. And in
part of my like Kevin gets canceled fund is they
have college funding, they can live. We got to move.
You're good, okay, I'm good at saving and I need.
I moved from La and I the world is overplanned La.

Speaker 1 (47:46):
You're gone.

Speaker 3 (47:47):
Yeah.

Speaker 2 (47:47):
I live in South Carolina or or Atlanta or somewhere
like that. But absolutely it's a fear to this day.
It doesn't matter how well I do. This sky is
going to be falling.

Speaker 1 (47:57):
One day.

Speaker 2 (47:57):
Everybody's gonna hate me. And when you've gotten dragged on Twitter,
you don't know when it's like for real, losing followers,
you don't know when you show time. Yeah, so it
feels like that I have a question for you, and
I'm gonna let you go.

Speaker 1 (48:11):
One.

Speaker 2 (48:11):
I wanted to say the thing that I forgot the beginning.
Thank you for telling Kevin Hart you don't ask for help,
because I would not have asked you to do this
podcast if you didn't make that. That's crazy, crazy, I
would not have asked you. I don't see anybody who
is absolutely my peer or in my network as my peer.
And you you've already done stuff for me, like but

(48:33):
I'm like, oh no, East all the way here now,
and it's so I'm really grateful for that. And you
also said you you ain't the friend that checks on people,
and I was just like.

Speaker 3 (48:46):
I got dragged for it. I found out later.

Speaker 4 (48:49):
I was like, what y'all at even watch the whole
thing we were talking about?

Speaker 3 (48:52):
Let up anyways, but yeah.

Speaker 2 (48:54):
But like I am that person too. I'm just not
good at that. I'm just so and I'm you know,
we're being honest here. So I wanted to thank you
for that, and also you gave me one of my
greatest stories. I got an email to the audition for Insecure,
and I thought I got the role, and I was
at all deaf and I talked so much trash of

(49:17):
the people at the offense office. I was like, boy,
y'all niggas don't know I'm on here on Insecure. I
got an email directly from Easter Ray, I'm gonna be
on the show, and I talked trash, walked around and
put it in everybody's face. Got home and I was like, oh,
this is It's not from Issa directly, this is from
like a casting director. And at the bottom of the email,
which I didn't scroll to in the office, there were

(49:39):
audition instructions. Oh my gosh, I auditioned for the show.
Didn't get it, and I saw who got it made
way more sense. And then to hear actually booked Insecure,
so there was a little.

Speaker 1 (49:52):
Reverse bragging when.

Speaker 3 (49:53):
You're at death when oh my god.

Speaker 1 (50:00):
So.

Speaker 2 (50:04):
Like oh snap, oh dang, So I don't do that.
The road I was season one, it was like you did.
Like it was like a montage of dates and I
think maybe a season two.

Speaker 3 (50:18):
Yeah, I did ask for you to come in through that.

Speaker 4 (50:21):
Yes, Okay, see I had actually asked you actually did Yeah,
I asked, yeah, oh.

Speaker 2 (50:27):
Wow, the people who got it. When I saw it,
I said, well, that was actually great casting. And I
didn't know how to audition at that time. I realized now,
like my homegirl Angel just helped me. Like Angel and
like watching people, they've been like doing this thing where
they post the audition and in the scene and I'm like, oh,
I haven't been doing anything remotely near that.

Speaker 4 (50:49):
I learned being during like during Insecure is when I
learned like the audition process, because I've always been scared
of it and like felt rejected by it. But once
I was on the other side, and I'm sure you
did too, it's such just like somebody could be outstanding
and just either doesn't fit the aesthetic or you're not
the only voice. Like that was another thing I had

(51:09):
to learn and be respectful, like, no matter how strongly
I felt about something, yeah, Prentice and Malina, we're gonna
feel a way too, and like, I have to take
that into account. This isn't a dictatorship. And so like
all those things, I wish actors could just have the
opportunity to.

Speaker 3 (51:24):
Be on the other side and understand, like, no, it
was it wasn't you. You were phenomenal.

Speaker 2 (51:31):
It's very helpful to be on the other side because
you you don't hear back, and that's the part that
works the most. You just don't hear back. The thing
just comes on, yeah, oh so I didn't get that.

Speaker 3 (51:41):
Yeah, you know, you don't even get feedback. It could
be helpful. Nobody wants to hurt anybody's feelings, and.

Speaker 1 (51:47):
So it hurts more.

Speaker 2 (51:48):
But at least tell me what I did or didn't do, like, nah,
we just ain't gonna say nothing, man.

Speaker 4 (51:58):
I also have to see the same cast and directors
are see the same people, which I'm sure now we're
talking about it, you just have to act like it's
all good, like oh yeah, yeah, now I saw like
I love the Trust shows on Yeah, yeah cool.

Speaker 2 (52:11):
I've seen one cast director that I've auditioned for eighteen times,
and I'd just be like, just don't call me. That's
one of the reason I make my own stuff. I
make myself number one on the call sheet. Yeah, because
it's me, Me, Kevin. I can act, I can take direction,
but you talk about just thirty seconds to prove myself.

Speaker 1 (52:26):
I can't.

Speaker 3 (52:27):
That is so nerve wracking.

Speaker 4 (52:29):
That's honestly one of the reasons I love Robin Thedi
because she made me feel when I had to. When
I auditioned for the Nightly Show, I knew I was
bad going into that, Like as soon as I got there,
I just fell apart, but she was just laughing so
hard and you know, trying to encourage me.

Speaker 3 (52:47):
And I didn't know her like.

Speaker 4 (52:48):
That, but it really just it stood out because you
don't you don't usually get that experience, and she was
just so sweet and warm.

Speaker 1 (52:54):
Wait, give me the timeline on this.

Speaker 4 (52:58):
So when Larry, I guess it was around twenty thirteen.
Maybe when Larry it was like, look, I love you, sis.
But I got the opportunity in my dreams to do
the Nightly Show. I'm gonna do that, and so I
was like fuck. So then he was like, but you know,
you should come on an audition to be a correspondent,
And so that I auditioned to be a correspondent for

(53:19):
the Nightly Show.

Speaker 3 (53:19):
Robin Thedie was a head.

Speaker 4 (53:20):
Writer at the time, and I auditioned in front of
her and yeah, bomb that audition.

Speaker 1 (53:25):
Hey guys, taking a quick commercial break, We'll be right back.

Speaker 2 (53:48):
This is what I love about in Hollywood, not that
you bombed that audition that came out at a weird time.
You don't know who's gonna become who, and treating everybody kindly.
Because Robin treating you kindly and you become Issa Ray.
You end up being part of the reason she gets
her show on HBO if I understand that correctly. And

(54:09):
some of that just comes from treating everybody with respect
because somebody who was an assistant. This happened to me
early in my career. I treat everybody nice anyway, but
it's a helpful skill people who are assistant. When Zaise
and Jojo first started were executive producers are movies within
six months, and I mean they were going across the
street grabbing coffee type of assistance, like here's your coffee,
here's your donut, here's your schedule. When I came back,

(54:30):
there are I cut playback and I'm like, dang, this happens.
And then sometimes you're on Times Square billboard that shows over,
you're on an unemployment line, you're back auditioning. You don't
know which person you're gonna be. So real, so treating
everybody nice. That's why I treat people kind like I'm
having a good moment now, but a year from now,
I might be right back in comedy clubs, which I

(54:52):
got no problem with. I gotta feed my family and
feed the dog. But I would never have nobody be like, yeah,
look at you now, Kevin. When I was trying to
get on, I couldn't do it. I'm so grateful that
I'm gonna.

Speaker 1 (55:04):
Let you go.

Speaker 2 (55:05):
One one more question. Have you struggled with Ray unknown
and now as far as like outside of or inclusive
of social media, friends, family, perception, jobs, at people asking
for stuff? Have you do you feel like you've dealt
with that in a good way. Do you feel like

(55:25):
that's been difficult?

Speaker 4 (55:28):
Yeah, it hasn't been, because you know I'm from here.
I have my my solid friends that I've known forever.
I have a obviously like a great family. That separation
like people who knew me before, you know, my husband
knew me before all this happened. That's been fine, but yes,
I've had to navigate like, oh, this person doesn't really

(55:49):
want to be my friend, you know, like oh.

Speaker 3 (55:53):
They didn't want to just go to lunch.

Speaker 4 (55:55):
Oh, like that's I've I've recognized that, and that's a
little bit longer of just like, oh, people might feel
like they need me or they they depend on me
in a different way. And I've had obviously extensive extended
family members and things like that hit me up for
the money stuff, and that feels separate, but like it's

(56:18):
the it's the undercut, like I'm going to try to
use you, and I can generally see that, but some
people are just way more slick with it.

Speaker 2 (56:30):
Do you feel like I'm very glad for you that
you have pre ease of fame? Do you feel any
different now or how have you been able to navigate that?

Speaker 4 (56:42):
Yes, and no, it's made me more close off to
maybe like newer relationships where I would have extended myself
before and just be like yeah, And sometimes occasionally I
will be like, yeah, here's my number, here's my email,
like hit me up and then we'll follow through. But
I used to do that way more often because people
will they'll suck like I've I just did that recently

(57:02):
for someone where I reunited with them, and no, lie,
they hit me like every every other day, and I
just was like, oh, this has now become a job,
and like I can't. I can't do that, you know.
So yeah, I've just been wearying. But I'll always try
to help someone. I will always always try to do

(57:24):
what I can to help someone, and I recognize those
people in my life that will do the same for me,
and I appreciate that.

Speaker 1 (57:33):
All right, He's a ray God bless you. Thank you
so much.

Speaker 2 (57:38):
If there's anything to share, you can if not, were
just appreciate you for coming on.

Speaker 3 (57:43):
I appreciate you. Congratulations.

Speaker 4 (57:46):
You know you are again someone that I admire so much,
and I appreciate all the kind things you always say
about me. They just know, I hope you never hesitate
to ask, because now I will not hesitate to ask you.

Speaker 2 (57:57):
Oh well, I've used up a favorite, So three it's
your turn for sure your term for sure, Ladies and gentlemen,
Easter Ray, It's been not my best moment. Kevi on stage,
Thank you got so much for see you next time.

(58:37):
This has been a Unanimous Media original Not My Best
Moment was produced by iHeart Podcasts and Unanimous Media. It
was hosted by me Kevin Fredericks, Executive produced by Stephen Curry,
Eric Payton and Charlotte Sumter. Jet co executive producer Kelenna
Maria Cutney. The executi producers of the iHeart podcast are
Sean Titne and Jason English. This series was produced by

(58:58):
Peter Calter and Jabbari Davis. Co producer Kurt Redman. Special
thanks to Stephen Curry and Will Pearson. Not My Best
Moment as a production of Unanimous Media and iHeart Podcasts.
For more podcasts from iHeartRadio, visit the iHeartRadio app, Apple Podcasts,
or wherever you get your podcasts.