Pod Insights IMO with Michelle Obama and Craig Robinson Find Your Adventure with Katt Williams About this episode Comedian Katt Williams joins the podcast for a characteristically unpredictable conversation about his complicated childhood, and how his early years set him up for a career in comedy. Katt shares what it was like being raised as a Jehovah’s Witness, how moving by himself to Florida as a young child helped form him, and what his relationship is like with the women in his life.
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Transcript 11,667 words · 5 speakers
Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Speaker 00 At that time, I had already read so many books and I was excited about it. So I was like, oh, I'm guaranteed, I'm a sure thing. A terrible childhood, like, I'm guaranteed to make it. Like, all the heroes and all of these stories.
0:16 Michelle Obama? This is where it all begins.
0:17 Speaker 00 Poor girl Cinderella's pleading the chimney. The stepmother's awful.
0:21 Michelle Obama? You're like, I'm right on track.
0:23 Speaker 00 Oh, I'm like, God, you really know how to do it. Like, no, this is why you leave at 13.
0:29 Michelle Obama? That's right.
0:29 Speaker 00 I get it, Jesus.
0:30 Michelle Obama? Yes.
0:36 Michelle Obama? This episode is brought to you by Rivian and Progressive Insurance. Hi, Craig Robinson.
0:44 Craig Robinson? Hi, Michelle Obama. How are you today?
0:45 Michelle Obama? Good. Welcome back to IMO.
0:47 Craig Robinson? Yes, on the vineyard.
0:49 Michelle Obama? On the vineyard. It's been a really, really lovely recording here in this beautiful space.
0:55 Craig Robinson? It really has.
0:56 Michelle Obama? You know, they're, they call this a barn, but.
1:01 Craig Robinson? But this is a high-level barn.
1:02 Michelle Obama? This is not a barn.
1:03 Craig Robinson? This is, this is.
1:04 Michelle Obama? This is just another house.
1:06 Craig Robinson? As, as, as Aaron said, who's my 13-year-old.
1:10 Michelle Obama? Who's with us today.
1:11 Craig Robinson? Yeah, this isn't a barn. This is somebody's house.
1:13 Michelle Obama? He heard that we were recording in a barn. He pulled up. He was disappointed.
1:17 Craig Robinson? He was disappointed. He wanted cows and horses and stuff around. This is not, this is a chic.
1:22 Michelle Obama? But this area of the island, up island, Chillmark, is the best place to have a Rivian.
1:31 Craig Robinson? Yeah, yeah. And as everyone knows, we got gifted Rivian. So I've been driving yours around and I've been all over the island, but I haven't been up this way. I haven't been up island, so I'm saving that for my next trip.
1:44 Michelle Obama? Yeah, but you can see how these backroads, you know, how the Rivian really operates well in it. Yeah.
1:50 Craig Robinson? Perfect, perfect. Raise your suspension up, have a little nice, little comfortable ride.
1:56 Michelle Obama? That feature is good. So do you have to raise it up or is it already raised? Or are you lowering the suspension?
2:04 Craig Robinson? There's two or three levels that you can set it.
2:07 Michelle Obama? Yeah.
2:07 Craig Robinson? And depending on the terrain, so in bumpy, you would raise it so that you can get over rocks and stuff and don't scrape the bottom. And you lower it to go faster on like the highway.
2:19 Michelle Obama? Have you used it?
2:20 Craig Robinson? I've used all three settings. You know I have.
2:23 Michelle Obama? Excellent.
2:23 Craig Robinson? Yeah.
2:24 Michelle Obama? Excellent.
2:25 Craig Robinson? Yeah.
2:25 Michelle Obama? Well. It's good to be here.
2:27 Craig Robinson? It is, but we not gonna mess around today because we are both excited about this.
2:32 Michelle Obama? We are so excited.
2:35 Michelle Obama? Just settle down.
2:36 Craig Robinson? Man, we have Cat Williams here. I mean, I'm chilled, I'm chilled on this hot day in the vineyard. Cat Williams is obviously a comedian and an actor who's earned worldwide reputation as one of the world's top entertainers. He's celebrated for his brilliance and ingenuity onstage, which you and I both enjoy. He's also known for his critically acclaimed stand-up specials and today remains one of the top touring comedians.
3:11 Michelle Obama? On fire, all the time.
3:12 Craig Robinson? Just on the time. And he's currently on his Heaven on Earth tour and he is performing in arenas all around the country and we have to make sure we get to one of these because I want to see him live.
3:23 Michelle Obama? We gotta find out where it's going.
3:24 Craig Robinson? But without any further ado, can we get the?
3:27 Michelle Obama? The one, the only.
3:28 Craig Robinson? The one, the only Cat Williams.
3:37 Craig Robinson? You came out like you were called out to the principal's office.
3:44 Michelle Obama? He came ready, ready. Hi, Cat Williams.
3:49 Speaker 00 Hello there.
3:50 Michelle Obama? Welcome to.
3:50 Speaker 00 Thanks for having me.
3:51 Michelle Obama? I am all.
3:52 Speaker 00 Thank you.
3:53 Michelle Obama? You're a handsome dude.
3:54 Speaker 00 Right.
3:55 Michelle Obama? Yeah, you know that. You know that about yourself.
4:00 Speaker 00 You know, there were so many options, God had to make some people fire five. And, uh, you know.
4:09 Michelle Obama? It's your turn. Say, kids, because he gave all the rest of the hype to us.
4:12 Speaker 00 Yes, yes, you guys are both strikingly tall.
4:17 Michelle Obama? Well, it's good to have you.
4:18 Craig Robinson? It's so good to have you here, man.
4:20 Michelle Obama? You've been on the Vineyard too. How is, have you been to the Vineyard before? Is this your first visit?
4:25 Speaker 00 This is my golf retreat.
4:28 Michelle Obama? So you've been here before golfing? Okay, alright, okay.
4:33 Craig Robinson? And when did the love affair with golf start for you?
4:38 Speaker 00 It was immediate.
4:41 Michelle Obama? Did you grow up golfing? Because black, we don't, we don't grow up.
4:44 Speaker 00 No, that's not a thing.
4:45 Michelle Obama? No, it's not.
4:46 Speaker 00 I grew up getting.
4:46 Michelle Obama? It's not a thing. We lived on a golf, we lived in a neighborhood with a golf course. We, as black people, we just drove right past it.
4:55 Speaker 00 Yeah, it's probably the least economical sport.
5:00 Michelle Obama? Yeah, yeah.
5:01 Speaker 00 Possible, I'm saying. You only need one ball and thirty-nine guys to play.
5:08 Speaker 00 It's not that way with golf. But yeah, I was grown when I got introduced to golf. But it is, I've really been able to grow with my own personal game. And I like everything about it. There are no negatives or drawbacks.
5:26 Michelle Obama? What's your handicap?
5:28 Speaker 00 I'm unhandicapped.
5:29 Michelle Obama? What does that mean? What does that mean? Now, I don't even understand that.
5:32 Speaker 00 Just a healthy man.
5:34 Michelle Obama? Just a, are you a scratch golfer, as they call? I'm, I know all these terms from my husband.
5:40 Speaker 00 It's rarely, I have eczema, so I am a scratch golfer, but.
5:48 Craig Robinson? What are the attributes that you take from golf? That you can use in your entertainment life or your parenting life?
6:03 Speaker 00 Golf gives you the opportunity to do something exactly how the best player in the world would do it. And then, six minutes later,
6:16 Speaker 00 you hit a shot that a nine-year-old.
6:23 Speaker 00 And this is the same you. Yeah. You know, and having the ability to navigate your own personal expectations and to understand that you always have the ability to do better. And that if you had a great hole, you put that behind you, even as you would if you had had a terrible hole.
6:53 Michelle Obama? Yeah.
6:53 Speaker 00 You have to put the greatness of that hole aside because hole 13 doesn't matter at hole 14.
7:01 Michelle Obama? Well, you know, we're gonna be, the golf course that we grew up by in Chicago on the South Side, that we just drove past and never went in. Now, the Obama Presidential Center is opening up there in May, and there's an athletic center, it's a whole development. It's on that golf course. So, we're gonna have to, I'm gonna commit you now, you gotta come out.
7:26 Speaker 00 Done.
7:26 Michelle Obama? Because we are trying to get young people, black kids, exposed. Because to be living in a neighborhood with that kind of beauty and not be able to access it, as we were not. Because all we were doing was just riding past it. It's a, it's a good way for Barack to connect his love of a sport to the neighborhood that it's given us so much. So, we would love to have you involved in that. So, I'm gonna use this opportunity to get you on the hook.
7:56 Speaker 00 Yeah, absolutely, absolutely.
8:00 Speaker 00 You and your husband are one of only a handful of actual superheroes that we've seen in the country. And...
8:12 Speaker 00 A superhero is somebody you put ungodly expectations on, you expect them to never make mistakes, and you want them to be flawless, and just things that just aren't realistic for humans. But the way that you two pulled that off was, I think when we look back 100 years from now, like you were the source of pride for a nation that needed that. So, yeah, whatever we can do.
8:46 Michelle Obama? Thank you.
8:47 Speaker 00 Pay you back for that, we'd love it.
8:49 Michelle Obama? Thank you, Kat, that's very sweet of you. Oh, we can end it now.
8:52 Speaker 00 Yeah, yes. Right, money's worth it. I'm not done yet.
8:57 Craig Robinson? Right, so when you, when you sat down, you said you, you grew up getting whoopings.
9:04 Speaker 00 That was an odd thing for me to just come out with.
9:07 Michelle Obama? Yeah, but black folks, we know, we all know about a whoopin'.
9:11 Craig Robinson? We know, so I wanna, I wanna back up and just hear how Cat Williams became Cat Williams. So I wanna know how, you know, how did that start?
9:26 Speaker 00 So I really owe everything in my trajectory to the love of books that I forged early. So, um, reading books just shaped me into this. So, for example, I can remember young figuring out that my mother and father didn't really love me, but they took really good care of me.
10:10 Michelle Obama? How good you, what made you say they didn't love you? What did they do that left you with that feeling?
10:18 Speaker 00 Nothing, nothing, I just, um...
10:23 Speaker 00 I was reading so many books. And I was seeing so many stories. And I was just trying to figure out where I fit in with these stories. If I was that type of person. And I, I realized that my mother never kissed me, right? And that there was this dynamic that existed in other households that I didn't have in mine. But I was, at that time, I had already read so many books that I was excited about it. So I was like, oh, I'm guaranteed, I'm a sure thing.
11:05 Speaker 00 A terrible childhood, like, I'm guaranteed to make it. Like, all the heroes and all of these stories.
11:12 Michelle Obama? This is where it all begins.
11:13 Speaker 00 Poor girl Cinderella pleading the chimney. The stepmother's awful.
11:17 Michelle Obama? You're like, I'm right on track.
11:18 Speaker 00 Oh, I'm like, God, you really know how to do it. Like, no, this is why you leave at 13.
11:24 Michelle Obama? That's right.
11:25 Speaker 00 I get it, Jesus.
11:25 Michelle Obama? Yes, yes.
11:27 Speaker 00 Way to turn it around. Yeah, way to turn it around. But understand, I'm that early.
11:31 Michelle Obama? Yeah.
11:31 Speaker 00 Like, because.
11:33 Michelle Obama? How old?
11:34 Speaker 00 Like, six.
11:36 Michelle Obama? Yeah.
11:36 Speaker 00 Yeah, I, I had already made the decisions at six, just because
11:43 Speaker 00 once you've read thousands of books, you see that all of these stories are similar. And that you're gonna make it through. Like, they're like, depression is the worst disease because it makes you think things that are incorrect, you know? So I, I was reading so many books of so many people in so many different circumstances. And it always works out. It always gets better. Life is always worth the next adventure. And so. That's how I was looking at things even that early.
12:26 Michelle Obama? How many brothers and sisters did you grow up?
12:29 Speaker 00 I'm the oldest.
12:29 Michelle Obama? You're the oldest.
12:30 Speaker 00 I have two younger brothers.
12:31 Michelle Obama? So, so did your parents have you sweeping chimneys and whatnot? I mean, what was it about your childhood that made you read those stories and say, you know what, I'm missing something, you know?
12:46 Speaker 00 Well, I wasn't at the age where I thought I was missing anything. Now, granted, in retrospect, I was. But I was using all of my setbacks for my benefit. So I, so for example, like I wasn't allowed to watch television or see movies or go over people's house or go to a dance. There were no extracurricular activities of any kind. But I devoted all of that time to reading. So I got three open books.
13:19 Michelle Obama? Yeah.
13:20 Speaker 00 Every day, I'm in the middle of these and I'm, I'm immersed and I'm getting, I feel like I'm really learning something from everyone's experience and that is putting me ahead of the curve because of how much knowledge and information I'm getting on something that doesn't have anything to do with me. Like I'm, I'm reading about Winston Churchill. But the stories all go together.
13:53 Craig Robinson? And, and, and this, this, uh,
13:59 Craig Robinson? situation you were in, not being able to do a lot of stuff, that was because, was that because your parents were religious?
14:06 Speaker 00 Yeah.
14:07 Craig Robinson? Okay.
14:08 Michelle Obama? They were Jehovah's Witness.
14:09 Speaker 00 Right.
14:11 Speaker 00 And high up in your organization.
14:13 Michelle Obama? Yeah.
14:13 Speaker 00 But, you know, a lot of the things that I learned, I, I learned because of that situation. So I already knew that when I got in the position to be a parent, I understood.
14:28 Speaker 00 Love is the most important thing and it's free.
14:32 Michelle Obama? Yeah.
14:32 Speaker 00 Like, you can do that.
14:34 Michelle Obama? That's right.
14:34 Speaker 00 And I know all the other stuff seems to matter, but actually, the imparting of love and creating an individual that knows how to receive it and give it and deal with it is just so important. And don't get me wrong, my father was a a great father, he's a great husband. My parents are still together, they've been together almost fifty years now. So like, they're they're wonderful, but-
15:04 Michelle Obama? What's your relationship like with them today?
15:09 Speaker 00 My love for them today, same as always. I'm more that they got more respect for me for how great of a job that they did, even when the feelings weren't there, you know? And I appreciated that and that made it so much easier for me to adopt children because I realized, you know, DNA doesn't matter, bloodlines don't matter. Family's where the love is.
15:37 Michelle Obama? Yeah, that was another thing I didn't realize about you, that you have adopted a lot of kids. Tell us-
15:45 Speaker 00 Yeah, I didn't see that in the bingo cards.
15:49 Speaker 00 But
15:51 Speaker 00 my son's mother was living in another state and she had another life and had kids. And at some point,
16:03 Speaker 00 she faced an addiction crisis and her children went to the orphanage. So when they called me, I don't have a direct relationship with these children, but they are the siblings of my son. And I did all the research and I knew that it takes a million dollars to raise a child.
16:28 Michelle Obama? Yes.
16:28 Speaker 00 And I was eager to say, wait a minute, Lord, are you-
16:36 Speaker 00 Are you, you're saying I'm gonna have 10 million dollars to take care of 10 kids? Fine, let's do it.
16:42 Michelle Obama? I'm in.
16:42 Speaker 00 Let's go.
16:43 Michelle Obama? Yeah.
16:44 Speaker 00 Because you, you, you don't wanna let me suffer. You're certainly not gonna let. And it was the best experience.
16:52 Michelle Obama? How old were you when you adopted the kids? And what stage in your life? Were, were you already in comedy? Were you already Cat Williams? Or was this?
17:02 Speaker 00 Yes, ma'am, but a lesser form, a smaller case K.
17:08 Speaker 00 I was making less than 25,000 a year. So that lets you know where I was.
17:20 Speaker 00 But I had been working and everything was looking good. It, it was a period in my life where I think
17:36 Speaker 00 that's the only way he could save me is to give me this instant humongous family and all of these.
17:42 Michelle Obama? Did you need saving?
17:43 Speaker 00 I did.
17:44 Michelle Obama? What was going on?
17:53 Speaker 00 I love women so much.
17:57 Michelle Obama? Tell us more.
17:58 Speaker 00 And so I, I had a five bedroom house with a woman in each room.
18:05 Michelle Obama? Oh, cat.
18:06 Speaker 00 Because, because I like women. I like waking up, hearing them. I like them being around. Like, that's my sweet spot.
18:18 Michelle Obama? Well, it sounds like you weren't in crisis.
18:20 Speaker 00 No, it wasn't in a crisis. No, it wasn't that type of crisis. It's just that the kids happening instantly like that meant, nah, I gotta grow up. I gotta do stuff a different way. Like, I gotta do a different trajectory. Like, I'm gonna be a family man now, you know? So I couldn't be the Bachelor superstar that I had envisioned at that point that I was getting ready to go into. So, yeah, it saved me for sure.
18:49 Craig Robinson? What was the biggest challenge in your parenting career?
18:54 Speaker 00 The hardest part is, um.
19:01 Speaker 00 Losing a child is probably the
19:08 Speaker 00 worst thing that could happen to you on this earth. There's no recovery from it. There's no...
19:15 Michelle Obama? You lost a child? I'm sorry.
19:16 Speaker 00 Yes, ma'am.
19:17 Michelle Obama? I'm sorry.
19:21 Speaker 00 Yeah, that was probably the only regrettable thing is that
19:29 Speaker 00 I had built myself to be completely impervious to the machinations of the devil. So there was nothing Satan could do that would ever
19:42 Speaker 00 take my joy from any situation. And the worst things are going for me personally, the more you can probably find me smiling and telling jokes because that's how we get back.
20:00 Speaker 00 But in that particular
20:04 Speaker 00 circumstance, it's the worst thing imaginable. It doesn't get any better. It actually gets worse. But yeah, other than that, it was complete joy.
20:27 Craig Robinson? This segment is brought to you by Progressive Insurance, a brand that knows homeownership isn't just about having a place to live. It can open doors in ways you didn't expect. And not just for you, but for those who come after you. And you know, when I think about some of the challenges and the benefits of homeownership, I really think about the neighborhood we used to live in and...
20:52 Michelle Obama? When we were growing up or where we moved to?
20:54 Craig Robinson? Where we moved to when we bought our homes. And I picked the area because I knew it had stable home prices. And we knew it had really good schools. And the really good schools part was the first part. And then we got the added benefit of it was such a good area. Our friends and family ended up moving there too. And that's how we began to build our community and build our friends. And have sports and parties. And it was not a benefit that I had looked for. I thought we were going to have to build a whole new community. And what happened was our community came to us.
21:37 Michelle Obama? Yeah, that was certainly, you know, one of the highlights of living in Hyde Park. It is a well-established community. It's diverse. It's got tons of amenities, not just schools. But where we lived was right down the street from the Museum of Science and Industry. And that was a benefit when the kids were little to have the museum that was full of exploration and wonder. A walk away from your house. So you remember, we used to grab the kids on any given day. Or mom could pick up the kids, walk down to the museum and they would spend an afternoon.
22:17 Michelle Obama? So it's not often that you get to live next to one of the most highly visited museums in the city. So that was a huge benefit.
22:26 Craig Robinson? Yeah, yeah. First time homeownership can bring unexpected benefits, creating flexibility, new opportunities for family. Sometimes the best parts of owning a home aren't what you planned for. Maybe it's the space to host family and friends, or just a sense of pride and accomplishment of owning your future. No matter your homeownership goals, Progressive has got you covered. In 2024, they committed over $7 million to housing initiatives and continue to support first time home buyers with online tools.
23:02 Craig Robinson? And resources aimed at helping you navigate the homeownership journey with confidence. The goal is to help you feel prepared for what comes next. And maybe even enjoy a few surprises along the way. To learn more about progressive tools, resources and guidance for first time homeowners. Visit progressive.com slash open the house.
23:32 Michelle Obama? What do you think parenthood taught you about yourself? Especially since you had a bunch of kids?
23:45 Speaker 00 That there's no such a thing as doing a great job. There's just such a thing as doing a bad job. And if you're making sure that you're doing a good job. Then that should take a lot of the panic and anxiety away from you.
24:06 Speaker 00 I think I learned that the most patience. If you have a special needs child, you
24:16 Speaker 00 just look at the world differently. You realize that the special needs community is like the only legitimate angels on earth. Like a lot of the things that make people a bad person. Somebody with autism doesn't even know how to do that.
24:33 Michelle Obama? Yeah.
24:33 Speaker 00 They don't know how to be jealous or envious and conniving and.
24:42 Michelle Obama? One of my favorite guilty pleasures is, have you seen Love on the Spectrum? I just love that show. Oh, I mean.
24:52 Speaker 00 Everyone on it.
24:53 Michelle Obama? Everyone on the show and Craig, my brother is never caught up on any social media.
24:59 Speaker 00 I apologize. I apologize.
25:01 Michelle Obama? It's a beautiful, it's a reality based show and the producers of that have worked on later daters with us. And so it's the kind of reality TV that I really love. I mean, I love it all, but these are just really some of the best humans. They're autistic people who want to find love. And I, I think I cry every episode. It's just like you, like you said, Kat, the best display of humanity.
25:32 Speaker 00 Yeah, I watch it just to cry.
25:34 Michelle Obama? Yeah.
25:35 Speaker 00 Like, it's a, it's a free therapy session just to go and be reminded about how wonderful it is to be human and to see people searching to attain something that they can actually get to. And the fact that it goes from season to season and like, they're famous now.
26:00 Michelle Obama? They are. They need to be.
26:02 Speaker 00 Famous now, and yet they're still right where we need them to be. So it's such a genuine experience.
26:11 Michelle Obama? Do you have children who are autistic? You have one?
26:14 Speaker 00 I have one.
26:15 Michelle Obama? Yeah.
26:16 Speaker 00 Bless her heart. Yeah, we love.
26:18 Michelle Obama? Oh, my goodness.
26:19 Speaker 00 Good old Hannah. She's the best.
26:22 Michelle Obama? And I want to get back to, because one thing I didn't ask about child, you were, you were emancipated at 13. Is that?
26:32 Speaker 00 I've read that.
26:33 Michelle Obama? Yeah. Have you read that about yourself?
26:35 Craig Robinson? You've read that about yourself.
26:35 Michelle Obama? Tell us more about, it's not often that, you know?
26:40 Craig Robinson? And at 13?
26:41 Michelle Obama? And what led to that? Did you just walk out the door? Did you just say, hey, okay, thank you, everyone? I'm gonna take all my books and I'm on my own.
26:54 Speaker 00 I don't know how to put this without sounding facetious, but if, if you came from a Bible-reading, believing family.
27:02 Michelle Obama? Yeah.
27:03 Speaker 00 Then you already knew I was finna do what Jesus did.
27:08 Craig Robinson? Okay.
27:08 Michelle Obama? Bounce.
27:09 Craig Robinson? Okay.
27:10 Speaker 00 Now go find your temple to turn over tables. Like, this is, this is the life of a Christian revolutionary.
27:18 Craig Robinson? I got to tell you, you're way ahead of me. Because even if I wanted to leave at 13, I wouldn't have had the nerve to do it, nor the wherewithal that I could do it.
27:28 Speaker 00 It was a terrible idea.
27:29 Craig Robinson? Okay, all right, here we go.
27:31 Speaker 00 I don't talk about it because I don't want any young person to hear that and think that it's possible that they can pull it off.
27:42 Michelle Obama? But I think hearing, hearing that it's terrible is useful.
27:44 Speaker 00 But it wasn't. I just say that.
27:47 Craig Robinson? It wasn't terrible?
27:47 Speaker 00 No.
27:48 Michelle Obama? Oh, God.
27:49 Speaker 00 No, of course not. I'm the adventurer in this story. Are you kidding me? Okay. Want me now, sir? I'm grown. Got a mustache and a cigarette. I'm 12. You're welcome. That was my life.
28:05 Michelle Obama? I'm picturing little cat.
28:07 Speaker 00 It was terrible.
28:07 Michelle Obama? Did you have the stick in your, your goods and a little kerchief?
28:10 Speaker 00 No.
28:11 Michelle Obama? Did you walk out with a suitcase?
28:13 Speaker 00 I had a full suitcase and a Rottweiler puppy.
28:16 Michelle Obama? You left with a dog?
28:17 Speaker 00 Destined for failure.
28:19 Michelle Obama? It's like, and of dependence.
28:21 Speaker 00 I'm taking a responsibility.
28:23 Michelle Obama? Exactly. It's like, man, and I'll take this puppy. So where'd you go? Where was the first place you and your puppy, Rottweiler puppy, went when you left your house?
28:31 Speaker 00 Miami, Florida.
28:32 Michelle Obama? You went to a whole nother state?
28:35 Speaker 00 That was always the thing.
28:37 Michelle Obama? How'd you get to Miami?
28:38 Speaker 00 I went to a truck stop.
28:40 Michelle Obama? Oh, the best place to go. Wow.
28:43 Speaker 00 Because everybody's going out of here. And so then I checked license plates because I was looking for a warm destination and I was hoping for LA or California. But Miami presented itself and the guy let me and the Rottweiler puppy get in the back part of the empty truck and it would stop every once in a while.
29:08 Michelle Obama? Did you have any money? What, what, how'd you feed the Rottweiler?
29:12 Speaker 00 I was loaded. I must have had $1,200 and you could not have told me that I was not a young million.
29:20 Michelle Obama? Did you really have $1,200? How'd you get all this money?
29:23 Speaker 00 So the only thing I was allowed to do, I was allowed to cut grass in the summer and I was allowed to shovel snow in the winter. So I probably had 60 clients on each end.
29:37 Michelle Obama? You were an entrepreneur.
29:38 Speaker 00 I owned the lawnmower and the shovels.
29:41 Michelle Obama? Wow.
29:42 Speaker 00 And so me having money just gave me the ability to not have to wear the clothes that my parents wanted me to wear to school. I could wear that out, go change, get into something fly and presentable for school. And then, like, I was living. Multiple lives, but the money made it possible for me to have that freedom. And I learned that pretty early on.
30:07 Michelle Obama? What was your alter ego with your money when you went to school? Were you one way at home because you were dressing different? And then you took your lawnmower money and went to school in your whatever? What, who were you?
30:23 Speaker 00 I had a relationship with the candy lady. So I was in sales already and I was buying at a wonderful price, up selling and supplying schoolmates with candy and treats.
30:37 Michelle Obama? So you were that kid, you were the kid that had the nai-laiders?
30:40 Speaker 00 Plus I had money, so I didn't have to.
30:46 Speaker 00 I was able to treat the women that I liked.
30:50 Michelle Obama? Nice.
30:51 Speaker 00 Really nice.
30:52 Michelle Obama? Nice.
30:53 Speaker 00 And I learned that supplying happiness to people.
31:01 Michelle Obama? So you were Money Mike early?
31:03 Speaker 00 Yes, Money Micah.
31:06 Michelle Obama? Is that, was that where your character came from? Money Micah, you were, you were practicing that at 13?
31:13 Speaker 00 It seems like it's all planned out, but you know, God showed me early on that there was this pathway and I wasn't really certain of how to make sure that I was on it or.
31:26 Michelle Obama? Wow.
31:27 Craig Robinson? So you get to Miami?
31:30 Speaker 00 Yep, so we get to Miami.
31:31 Michelle Obama? With your puppy?
31:33 Speaker 00 Yeah, yeah, yeah. This trip probably only took us maybe three days at the most, maybe two. It was a really nice ride, but there, so I'm there. And I just had never seen a place so big with so many different neighborhoods and a different culture and ethnicity every three blocks. And it was really, really a bit of a culture shock. But I found a place in Coconut Grove at a park and that's where I made my residence. And it was across the street from a library. And so I would, eight hours a day, I would be in a library reading and.
32:16 Michelle Obama? So you just camped out?
32:20 Speaker 00 Literally.
32:20 Michelle Obama? Literally. Did you buy a tent with your money?
32:23 Speaker 00 No, ma'am.
32:24 Michelle Obama? So you're just laying out on the grass with your puppy, a thirteen year old?
32:28 Speaker 00 No, no, no.
32:29 Michelle Obama? And going across the street to the library?
32:31 Speaker 00 They had a whole little seg- segment of population that this was kind of a, in the homeless world, this was kind of a gated community.
32:39 Michelle Obama? Yeah, yeah.
32:40 Speaker 00 This park by them with a marina behind it, so you can't encroach. And it's in Coconut Grove. So, yeah, I was able to purchase a brand new mattress the first day I was gonna have to sleep. So I never slept on the ground or anything. And remember, my clothes are all dress clothes. I only have slacks and white shirts and ties.
33:00 Michelle Obama? Is anybody like, I'm just trying to picture this.
33:03 Speaker 00 I can't, I can't picture any of this.
33:05 Michelle Obama? And I'm still like, are you telling the truth or are you joking? Because I'm like, still trying to picture you. You went and bought a mattress? How'd you get the mattress to the park? I mean, I'm just. They delivered. Oh, you went to a store and you had them deliver your mattress to the park?
33:23 Speaker 00 There's a homeless hierarchy in the place that I was at. So there was a guy who was in charge of whether or not you got to be there or not. And because of my age.
33:35 Michelle Obama? How did you convince him that you should be there?
33:36 Speaker 00 I didn't. I've, I've lived a...
33:41 Speaker 00 I have a presence.
33:43 Michelle Obama? Yes, you do.
33:43 Speaker 00 And...
33:48 Speaker 00 I'm one of the people that
33:52 Speaker 00 doesn't have ulterior motives. And most people I've found do. But even at that age, I did, I didn't have any.
34:04 Speaker 00 I was, I didn't think I was owed anything. I didn't think I was in a bad experience. I thought I was making choices and decisions. And I was just trying to see if I could get them to work out. So when I get there, I get the mattress. And then there's this process where I find out how everybody else ended up in this park. And...
34:30 Speaker 00 That is what was life changing is to find these, to find out these are doctors and lawyers and nurses and accountants and, and each one of these people had an experience with drugs and it led them here. And, which is why when I emerged from this part of my story, like drugs are not a temptation for me because I've not seen or heard of parties or anybody having fun. I've just met these forty people whose lives were destroyed. And they're out in the
35:16 Speaker 00 elements, living with that and the fact that they're not going to be able to get those lives back. That this is a new reality for them. And so as a young, impressionable kid, being able to see the harshness of life like that, was very instrumental. And, and so when did you emerge from that? So if I fast forward, so now I'm in Florida. I'm thinking that, okay, I've left Ohio, right? So I have a humongous family in Dayton, a hundred first cousins, both sets of grandparents. So I'm like, you know, when I leave,
35:59 Speaker 00 this is gonna be a big deal. It's gonna be in the news, on the papers. There's gonna be a worldwide. It's like. Mine for your boy.
36:08 Speaker 00 Where, where is he?
36:11 Speaker 00 And these. Milk carton, dies on the milk carton. These conniving parents of mine. Let's say I left on Sunday. They moved out of the city on Monday. Oh, my God. So no one knows I'm gone. My grandparents don't know, nobody knows. Nobody thinks anything's wrong. What? My, yeah, it was, it was crazy. And so the way God works, I'm walking down a highway, maybe three years later, two years later. I'm walking down the.
36:48 Speaker 00 Shoulder and a car pulls over and I'm like, boy, these girls will not stay off of you, boy. They're pulling over on the highway now. That's a lot. So you gotta be pretty good looking for that one.
37:04 Speaker 00 Anyway, it's not any girls. It's my parents and my two brothers.
37:08 Michelle Obama? No way.
37:09 Speaker 00 And they are in Florida and saw me and said- Just like on vacation or something? Just passing through Florida. Oh, wow. So-
37:20 Speaker 00 Right.
37:20 Michelle Obama? Were you still living in the park?
37:24 Speaker 00 No, this is, um,
37:27 Speaker 00 at least a year later. So, no, I've moved from, from those confines. But, um, yeah, so now I am at this place, I think it's called Winter Haven or something. It's where the carnival people go when they're not in carnival season.
37:44 Michelle Obama? Yeah, no, I know nothing about this. You say this like, you know, Winter Haven, you know, the carnival people? I'm like, no, Cass, no.
37:52 Speaker 00 We swing through there in the summertime.
37:55 Michelle Obama? You know, I was like, am I supposed to know about this?
37:59 Speaker 00 This goes along with hearing an unbelievable story.
38:02 Michelle Obama? I love it. I'm just like, ooh, we need popcorn.
38:06 Speaker 00 You didn't.
38:09 Speaker 00 So, yeah, I was, I'm now away from Miami, near a place called Ruskin, Florida. And, um, my parents pull over on the highway and
38:25 Speaker 00 very apologetic and let's just put the family back together. And we end up moving to Haiti to do missionary work.
38:34 Michelle Obama? No, you didn't.
38:36 Speaker 00 And so I spend the next two years in Haiti.
38:39 Michelle Obama? What? Just, did you just get in the car? Where's the puppy?
38:42 Speaker 00 I just got in the car.
38:44 Michelle Obama? Where's your dog?
38:45 Speaker 00 So here's the thing, beautiful Rasha, right?
38:47 Michelle Obama? Rasha, oh, I love that name.
38:49 Speaker 00 I couldn't figure out, once I actually got into the homeless encampment, like, I could not believe that I had brought this puppy here, like-
38:57 Michelle Obama? Yeah, you were 13, that's 13-year-old thinking.
38:59 Speaker 00 I'm like, whoa. What's the plan for the baby? Like, how, this is gonna be hard enough to navigate on your own. But fortunately, because he was purebred and beautiful,
39:12 Speaker 00 he went for a great price. And that price sustained me for a nice little period of
39:19 Michelle Obama? Wow.
39:21 Speaker 00 time. So I understood why God had let me bring him. But yeah, he went to a great home and he supplied me a great income. And, yeah, so then, parents, then
39:32 Michelle Obama? They pick you up.
39:33 Speaker 00 Right.
39:33 Michelle Obama? They pick, what, I, I, I wanna know, shoulder the road? Do you get in the car? Is it like, Mom, Dad?
39:40 Speaker 00 Right, I really didn't.
39:41 Michelle Obama? And they're like, Micah.
39:42 Speaker 00 I really don't wanna get in the car. Like.
39:45 Michelle Obama? Are they like, get it, boy? Is it like that?
39:48 Speaker 00 No.
39:48 Michelle Obama? Are there tears? Are they like, oh, we've been looking for you?
39:51 Speaker 00 I'm the tallest person in the house, so let that, understand, like, I'm a big guy, you know, five-five, alright?
39:59 Michelle Obama? Okay.
40:00 Speaker 00 So, no, there's, there's none of that dynamic. It's just, um, I'm sure as parents, they didn't think I would do that. And, um,
40:12 Speaker 00 by the same token, they had crossed the line, you know? Like,
40:17 Speaker 00 they were,
40:20 Speaker 00 they were behaving as if I was a bad child and I was a great kid who hadn't engaged in.
40:31 Speaker 00 Yeah, so there were mistakes made. I, I, I was already smoking cigarettes at this point, so I'm using this as the reason why I can't come with you guys. Like, I'm grown now.
40:43 Michelle Obama? Yeah.
40:44 Speaker 00 I got stuff I do.
40:45 Michelle Obama? And I smoke.
40:45 Speaker 00 Bad things.
40:46 Michelle Obama? Right.
40:49 Speaker 00 They were like, no, you're fine. I was like, we'll see. Yeah, but really, I was just trying to see where they were at. And I couldn't figure out how they had located me.
40:58 Michelle Obama? So Haiti?
41:00 Speaker 00 Right.
41:00 Michelle Obama? Did they have the plane ticket? Did you?
41:02 Speaker 00 Yeah.
41:03 Michelle Obama? So you just hopped on the plane? And what was Haiti like? And how long were you all there?
41:10 Speaker 00 Uh, we were there for, uh, two years until the Americans had to leave because of, um, the papadoc,
41:19 Michelle Obama? Yep.
41:19 Speaker 00 baby doc transition. So,
41:25 Speaker 00 it was magnificent. It was, it was magnificent. It was, um,
41:31 Speaker 00 One of the best experiences of my life. I was able to really be in an adventure. And my parents, when we got over there, Haiti is a different country because all of the writings at that time are all in French. So you have to read French. But then they don't speak French. They speak Creole. And Creole wasn't in any books. So you had to learn Creole and French. So for the first year and a half that we're there, I'm the only person in the family that reads French and speaks Creole. So I'm really doing.
42:16 Michelle Obama? And you just were able to pick that up quickly.
42:18 Speaker 00 Yes, ma'am.
42:19 Michelle Obama? Wow.
42:20 Speaker 00 Yes, ma'am. Fortunate.
42:22 Michelle Obama? Yeah.
42:22 Speaker 00 But yeah, that experience changed everything for me. I was eating sugarcane and mangoes and filling my pockets full of salt because I found out that Haiti had the highest mortality rate for babies dying of dehydration. And so I knew the salt in the water trick. And so I would just go out and walk village to village. And if they had sick babies, I would give them this information about the salt water. And because I was from Ohio, they weren't... I was able to bring like a different irrigation style
43:04 Speaker 00 to the part of Haiti Santo that we were at. Just because it was such a big trek from where the village is to where the water source is. And so, yeah, I filled my days full of adventure. It was magnificent.
43:24 Michelle Obama? How old were you during this period?
43:28 Speaker 00 I suppose I'm 14, 15.
43:30 Michelle Obama? Wow.
43:40 Craig Robinson? As our listeners know, we've partnered with Airbnb on this show and I've been staying in Airbnbs while traveling both for my family trips and while traveling for IMO. In partnership with Airbnb, we wanted to share an opportunity to give back during this holiday season. Airbnb.org is a nonprofit organization founded by Airbnb that connects people to emergency housing in times of crisis. Since Airbnb.org was founded in 2020, they have housed more than 250,000 people, including those affected by the Los Angeles wildfires, the central Texas floods, and earthquakes in Turkey and Japan.
44:22 Craig Robinson? When a crisis takes away the comfort of home, even the simplest evening moments like a bedtime story or a shared meal feel out of reach. Nights are special, for many sacred. Nights often represent dinnertime, a warm shower, a show on the couch, reading kids a book, followed by getting into bed. And for us, nights are for doing homework, then if time permits, catching the end of a basketball game. You can visit Airbnb.org and donate a night for a family who has unexpectedly lost their home due to a disaster. Airbnb will be matching every donation until the end of the year.
45:07 Craig Robinson? Together, we can restore sacred time at home and give back the nights that matter. Hey everybody, Craig Robinson here. Amazon has everything for everyone on your list and I want to talk to you about last-minute Christmas shopping and holiday shopping because I was a chief offender there. And I tell you, before I found Amazon, it was a stressful time for me. I'd go around collecting everybody's list in the middle of December and try and get gifts and I was running around all over the place. But then I discovered Amazon and I saw how they do their last-minute deals and I can
45:48 Craig Robinson? always find savings on gifts for my family, whether it's toys, electronics, fashion, cosmetics, you name it, house goods, they've always got stuff on sale and I can get it relatively quickly. Then I'm not running around the mall stressing and sweating and gifts show up. They're right on time. I can get them wrapped and under the tree, no problem. So this year, if you're in my position and you're stressing, Amazon makes last minute shopping feel like you planned it weeks ago. So that, my friends, is my tip for the day.
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48:34 Speaker 00 It's now that we're back because you have to get out of Haiti. So now we're back in Florida and I realize I'm not gonna be able to stay with these nice people. And so I'm off again. And so now when we pick back up, now I'm in the situation where I'm at a comedy club and I don't mean to be there, but...
48:57 Michelle Obama? How did that happen?
48:58 Speaker 00 Well, because some of the carnies are going to this club.
49:02 Michelle Obama? Oh, got it. You went back to your carny crew.
49:04 Speaker 00 And so I'm with a group now and we go there and they're asking for ID at the door and I'm not old enough to even be in there. So this is gonna be a very embarrassing situation for me, which I'm not interested in. And then God comes, as he always does, and somebody walks past and they walk all the way past the line. They say, "I'm a comedian." And the guy goes, "Yep, you're number four." And he walks in and I'm like, huh, there you are. He always delivers me this pathway. And so bam, I'm comedian number five, right? So I don't know what that means. I don't know now that we're inside of there. I don't know what goes on.
49:45 Speaker 00 So there, they just explain, "Yeah, yeah, we're having a comedy competition and..."
49:51 Michelle Obama? But don't you look 14?
49:53 Speaker 00 Get five minutes? No, ma'am, I literally had this mustache since I was 12.
50:00 Michelle Obama? No, you did not.
50:01 Speaker 00 A full mustache. Like, that's, we get 5'5". I already didn't get the growth spurt.
50:08 Craig Robinson? So you got the hair.
50:09 Speaker 00 I would've been suicidal if the Lord did not provide other provisions. But he did, right? And so he gave me a great outlook and a full mustache.
50:20 Michelle Obama? And a full mustache, dang.
50:22 Speaker 00 And remember, remind yourself what I'm wearing.
50:24 Michelle Obama? Well, I don't know.
50:25 Speaker 00 I have this on.
50:26 Michelle Obama? Okay, so you're still dressing well.
50:28 Speaker 00 I got a class, a white shirt and this is all of my clothes. I don't have tennis shoes or shirts.
50:34 Michelle Obama? Dress clothes. So you always dressed like a grown man.
50:36 Speaker 00 Uh huh.
50:37 Michelle Obama? Right.
50:38 Speaker 00 I've been grown the whole time.
50:40 Craig Robinson? All right, so you get in the comedy club and they say, "All right, you got five minutes."
50:44 Speaker 00 Right, right. So I just get up there and I talk about being the...
50:54 Speaker 00 Black community for this entire city. Like, there's nobody but me. I'm the only black guy. Nobody else. And I talk about what that experience is like.
51:09 Speaker 00 Yeah, and that was my five minutes and... Did anybody laugh?
51:15 Speaker 00 Oh, they loved it. They thought it was hilarious because, again, what I didn't understand is I didn't understand why it connected. But it connected because it was all true. Like, there was no black community there. It was just me. And everybody was looking at me like, "What are you doing here?" And, you know, you want to hear what that guy feels like about his surroundings.
51:38 Michelle Obama? What did it feel like to make people laugh? Did that... Was that new? I mean, because you were all... You had been used to public speaking.
51:46 Speaker 00 Right. Yeah, at five, I'm in front of crowds of 10,000.
51:51 Michelle Obama? Converting folks.
51:54 Speaker 00 Well, that wasn't my job.
51:56 Michelle Obama? Yeah.
51:56 Speaker 00 Everybody that was in the arena was already converted. I'm reading Bible scripture and giving a talk about this particular... Right, so I just kept asking God to show me a glimpse of where I'm gonna be. And I just kept hearing applause. But I didn't know what they were applauding or what it was that I had done or said. So it was... It was really frustrating for me before comedy came along. But as soon as I did it that first time, I was like,
52:40 Speaker 00 "That's crazy. I think I got something from that." How could I have got something?
52:45 Michelle Obama? From that? Was that the vision?
52:47 Speaker 00 Like, I...
52:49 Speaker 00 So it's probably not another... It's probably...
52:55 Speaker 00 If I'm 16 then, then...
52:59 Speaker 00 It's almost another eight years before I do stand up. But I just had that in my head that this is a thing I could do.
53:10 Speaker 00 So then I go into door to door sales. I join this organization that travels around the country selling books and magazines.
53:17 Michelle Obama? You know, all I'm thinking is, this is a movie. And we have to do it at a higher ground. I mean, we're gonna finish this story, but I'm just like, dude. I'm just, I'm watching this movie.
53:31 Speaker 00 Yes, ma'am.
53:31 Michelle Obama? As you were telling it.
53:33 Speaker 00 Right.
53:34 Michelle Obama? Anyway.
53:34 Speaker 00 And I've done my best to try to live accordingly, knowing that it's gonna get looked back on.
53:42 Michelle Obama? Yeah, yeah. So I, I did interrupt you because, you know, it was later on, you know, so you realized that comedy was a thing. But then you were doing the door to door salesman work.
53:58 Speaker 00 Right.
53:59 Michelle Obama? To still earning in.
54:00 Speaker 00 Again, I'm in another experience that is shaping me for everything that follows. Because now I'm, every door, I don't know who is going to answer this. Hispanic, Asian, white, black, monetary, love. I don't know anything and I need to connect with this person. I need to ease their fears about a stranger at the door. I then need to be funny and engaging so that they smile. And then I need them to make this purchase that we both know they don't need.
54:38 Michelle Obama? What were you selling?
54:39 Speaker 00 It started with books and magazines and then it was cleaning product at the end.
54:49 Speaker 00 All right, so.
54:53 Speaker 00 Door-to-door salesman. Yep. Comedy next, or was there something in between? So I'm doing the door-to-door sales. And I knock on the door of
55:06 Speaker 00 five ladies of the night. And they are in a traumatic situation because their pimp was murdered. And they all witnessed it and they didn't know what they were gonna do. And um.
55:23 Michelle Obama? This is another like, what?
55:28 Michelle Obama? I know everybody here is just like, what?
55:31 Speaker 00 I volunteered for the pimp position on the auspices.
55:36 Michelle Obama? Well, you were already dressed for the.
55:38 Speaker 00 How to do it. Okay, okay.
55:40 Michelle Obama? You were already dressed for the part.
55:42 Speaker 00 We're getting there, okay.
55:43 Michelle Obama? Okay.
55:44 Speaker 00 So they trained me how to do this job, right? And they taught me so much, like um.
55:55 Speaker 00 I wasn't there very long, but those ladies really um, along with my sainted mother, those ladies really showed me what it was like to be a man. And they, because they, every night for hours, they would just talk about everything wrong with men. Like, men of all nationalities, shapes, sizes and colors. What's wrong with them? Why are they horrible creatures?
56:22 Michelle Obama? Yeah.
56:22 Speaker 00 And I was able to, at a still impressionable age, learn things. And learn what bothers women. And realizing that I was in charge of so much of that.
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1:01:00 Craig Robinson? Yeah, yeah, you know, we have questions that we get from our listeners. But before we get to that, what advice would you give
1:01:13 Craig Robinson? a young Cat Williams coming along? And maybe not even a Cat Williams because you're so One of one. You're so unique. What would you give to a young up and coming artist who sees you as a role model? How, what advice would you give them on how to navigate this
1:01:34 Craig Robinson? industry, this career, these processes?
1:01:46 Speaker 00 I would say
1:01:49 Speaker 00 if you believe in God, take as much pressure off of yourself as you can and apply that pressure to Him.
1:02:00 Speaker 00 If you believe in God, then you know that in His books, He's got certain contractual obligations as well. It's certain things He has to do in certain situations. And it's okay if you put Him in those situations. It's okay for you to say, I believe there's a God and I believe that if there is, He loves me and He would help me in this situation. It is impossible for you to do that and then watch something happen and not know where that comes from. And so any artist, I would just say,
1:02:44 Speaker 00 make sure that your relationship with God is one of the relationships that you're also working on, whether it's spouse, kids, everything else. Make sure to pay attention to your relationship with God because it really, it really is the difference maker in how things turn out. Everybody doesn't serve God. Some people serve the devil and they put Him in positions. And it's terrible to say, but if that person has a better relationship with Satan than you do with God, that's your fault too. And so.
1:03:26 Speaker 00 I think that's the only advice that I would give to an artist is to find your higher power and connect. Because until you do that, you're just a rudderless ship out here. And I know from my own personal experience that it doesn't matter how young you get that relationship. It's never too early.
1:03:55 Michelle Obama? Speaking of relationships, what's your take on relationships? Have you ever been married?
1:04:02 Speaker 00 I love relationships.
1:04:03 Michelle Obama? Have you ever been married?
1:04:04 Speaker 00 No, never married.
1:04:05 Michelle Obama? Would you, do you believe in marriage? Do you believe in?
1:04:08 Speaker 00 I do. Yeah, my parents are still married.
1:04:09 Michelle Obama? Yeah, well, what about you?
1:04:10 Speaker 00 I had a wonderful example.
1:04:13 Speaker 00 Yeah, what about me?
1:04:17 Michelle Obama? You've never been married?
1:04:18 Speaker 00 Right.
1:04:19 Michelle Obama? Would you want to be? Have you found the right person? Is it not something that you're interested in settling down with a single person? Do you envision what your parents have for yourself ever? Is that even a goal?
1:04:36 Michelle Obama? That's exhausting.
1:04:39 Speaker 00 No, not really. It's not that. It's, um, yeah, I think marriage is, is great. It's just that at the point in my life when that would have been the next thing that I was going towards, that's when I had this instant huge family. And then I, I was just so reticent to bring a person into this dynamic just because of how unfair that would be to this lady to have all of these kids that are not hers. And, and so I, I was trying to make myself
1:05:19 Speaker 00 a better version of me in advance for this wife, right? But in the meantime of that, I'm the one doing the cooking and laundry and the cleaning and the school wakeups. And so it got to the point where I was the wife. And, uh, yeah, so where I am now, I finally have something I could offer a lady. I suppose. Monogamies has not been.
1:05:50 Speaker 00 A part of my journey. I've tried to share this gift with whoever needed it.
1:05:58 Michelle Obama? Why, why limit it? Why limit this? Why, why limit? Why, why limit the world?
1:06:03 Speaker 00 This gift for whoever needed it. My man. Okay, Kat.
1:06:08 Michelle Obama? And you, and you're, you, you love, I love it. I do. Cause why? That's, that's, that's the ultimate question.
1:06:15 Speaker 00 He is all of our hero.
1:06:18 Michelle Obama? But you, you have a farm. Not, not, you, there's so much. There's, there's so many kind of little surprising layers.
1:06:27 Speaker 00 Right. Yes. Lovely farm.
1:06:29 Michelle Obama? A lovely farm. Is it like a full working farm? I mean, are you?
1:06:34 Speaker 00 We have a hundred ducks, a hundred geese, cows, pigs, goats, sheep. We have animals that you never see. It's just a wonderful, a hundred and some acre property in Americana. That's just magical. And it's the thing that I am creating, which is heaven on earth. The, the name of the tour. But it's a whole philosophy of whatever you think the afterlife is gonna be for you. You can start making that for yourself here somewhere.
1:07:18 Michelle Obama? Do you tour every year? Or how is your tours? How do you think about that? Is I, is it like training? Like you wanna be on tour every couple of years just to? Or how do you think about?
1:07:33 Speaker 00 I'm, I'm, I'm an athlete. I have the same season as my athlete counterparts. So in the NBA, they play 82 games. I'm not sure what it is in baseball, but I have a, a hundred shows. I, I, I do a hundred shows and then I tape a special. And that's been the routine that I've.
1:07:57 Speaker 00 Had since, I think 2001 was my first one, so.
1:08:02 Michelle Obama? Is this that work ethic that the lawnmower kid that got you that $1,200, the feeling like if I'm doing it, I've got, I gotta do my best, I gotta put it in, I gotta, you know?
1:08:16 Speaker 00 Well, I met, I met Prince when I was 12. And he changed the trajectory of belief for me. Like, I knew I didn't have to make any changes. This was a guy who was shorter than me. He was already rich and famous. And he had a purpose in life and, yeah. So a relative of his was my first girlfriend. She was a little older than I was. So if I was 12, she was 16. She had a family member that was coming into town. He was a musical artist. Because of my background, I wasn't really up on all of the musical artists as you would think that I would be.
1:09:00 Michelle Obama? But you had wooed her with all the candy that you supplied?
1:09:07 Speaker 00 I don't know if you can tell this, but I make really good conversation. And, you know, money's not an option. And I only care what you like. So it makes me. And you had the mustache. Right, I got a mustache and candy. What more do you want?
1:09:25 Speaker 00 But, yeah, so she's like, yeah, he's just gonna be here after, after his show at the UD Arena. And you should meet him. So I ride my bike over there and I go in the house and I meet this guy Prince, right? And.
1:09:53 Speaker 00 You ever meet somebody and go, "Ooh, this person's way smarter than me." Oh, yeah.
1:10:00 Michelle Obama? Oh, yeah.
1:10:01 Speaker 00 Right, so it was really my first time being in the vicinity of real brilliance, like when it's not for show. And so we're having this super deep conversation. And you're 12. Right, and we are connecting and we have decided at the end of this conversation, we're friends, right? So I get ready to walk out, say bye to my girl. Says you'll walk me down. So me and Prince are walking down these steps, but he's thinking, "We're going to my car." When we get down to the bottom of the steps, my bicycle is right there.
1:10:46 Speaker 00 And he's like, "What's that?" I was like, "What do you mean, what's that?" That's my, I'm thinking, I'm thinking he likes it. I'm thinking he's noticed I've got the tricked out monkey. He knows I'm full of cash. Yeah, you're looking at it.
1:11:03 Speaker 00 And that's when he lets me know that he's 18, a grown man, I'm 12. But because of our sizes, we just assumed that each other was the same. I don't know what I was saying. Sizes and mustaches. So for all, so he gave me the confidence to know, because up until that point in my life, I thought that there were some things I was gonna need to do in order to be good enough. Like, I gotta get taller. I don't know, this might be the first mistake God has ever made. Like, I can't find evidence that anyone in the world missed a growth spurt. You have to understand, ma'am, third grade, I'm 5'5".
1:11:49 Speaker 00 A giant among men.
1:11:50 Michelle Obama? You were like, I got this.
1:11:51 Speaker 00 Big man on campus.
1:11:53 Michelle Obama? Truly, right. It's like, man, and that was it.
1:11:56 Speaker 00 So Prince helped me see immediately I didn't have to get taller.
1:12:00 Michelle Obama? Yeah.
1:12:01 Speaker 00 He already had just signed his movie, I mean, his music deal. He had just produced his album by himself. He played 26 instruments on it. He did all of the jobs.
1:12:13 Michelle Obama? Yeah.
1:12:14 Speaker 00 And it had worked. And so I knew that I didn't have to make any changes. I just had to be in the right position and be right myself when it transpires. So super helpful, that guy.
1:12:30 Michelle Obama? Yeah, no, that would be, that's, that's, that's pretty powerful.
1:12:34 Speaker 00 Yeah.
1:12:35 Craig Robinson? Well, let's help some folk. Let's help one of our listeners.
1:12:38 Speaker 00 Yes.
1:12:39 Craig Robinson? All right, so we've got a listener from San Antonio, Texas.
1:12:42 Speaker 00 Okay.
1:12:43 Craig Robinson? And her name's Amber. And I think her question's gonna resonate with you, so.
1:12:48 Speaker 03 Hi, Michelle and Craig. I love the podcast. My name is Amber. I'm 32 years old and I'm from San Antonio, Texas. I opened my own salon at 22 and since then I've navigated both personal and professional challenges. After a difficult relationship and some time living independently, I believed I had found healing and stability. But due to unforeseen circumstances, I had to move back home, which has brought its own emotional complexities. Over the past two years, I've been seriously considering relocating to New York City or Boston, not only to pursue greater opportunities in my industry, but also in hopes of building a life that breaks generational cycles. I've been taking small intentional steps,
1:13:32 Speaker 03 investing in my business, putting myself out there and making growth a priority. When I listened to your conversation with Kiki Palmer, I was struck by the part where you shared how you began seeking new paths and meeting people after realizing law wasn't your true calling. So my question is, when you were stepping into unfamiliar spaces and pursuing something new, did you feel overwhelmed or afraid? If so, how did you move through that fear without letting it stop you?
1:14:04 Craig Robinson? All right.
1:14:04 Michelle Obama? That's a big one.
1:14:05 Craig Robinson? That's a.
1:14:06 Michelle Obama? It's a doozy.
1:14:07 Craig Robinson? That's a college level essay question.
1:14:12 Craig Robinson? So any thoughts for Amber, just off the top of your head?
1:14:16 Speaker 00 I'm ready.
1:14:17 Michelle Obama? Yeah.
1:14:17 Speaker 00 Okay.
1:14:21 Speaker 00 Amber, you're doing the work. And when you do the work, an answer comes out. So I don't think that you're confused in any way. I don't think you're wondering what it is
1:14:36 Speaker 00 you need to do next. I think you already know. I think you know that there isn't anything for you at the Riverwalk. San Antonio is a wonderful place, but it's not going to get you to where you see yourself being. I think very specifically, you picked New York and Boston. If the fear is what you're dodging, the fear is necessary. The fear is there for a reason. The fear is to make sure that you don't take this for granted this time and end up in San Antonio for the third time. The fear is useful. On the other hand,
1:15:18 Speaker 00 you're only going to look back and go, I should have left earlier. Why didn't I go earlier? Not anything else. You're not ever going to regret this decision. You're going to regret the time it took you to get to this decision. All of the new relationships, your whole new life is there. And you deserve at 30, whatever you are, to be able to pull that parachute and do a new life. And if you mess that one up, go from New York to Boston now. It never stopped being in search of your calling and your purpose. It is there. You are going to find it. You're right on schedule. You're not behind.
1:16:01 Speaker 00 There's nobody to blame and there's only upside. So I, I think you're doing great, Amber. I think you know you're doing great. I think you just wanted us to reaffirm that you're making the right decisions. You're not crazy and yeah, good luck.
1:16:15 Michelle Obama? Yeah, I love that. I love that cat. Wise cat, all the layers of cat. I like, I like it.
1:16:25 Michelle Obama? I, I would address the fear part of it because I talk about fear a lot. You know, I, I agree, you know.
1:16:34 Michelle Obama? Fear is there for a reason and it's just interpreting the fear that you, you have. There, there is an element of fear and caution and everything. And that's a, that's a good thing. I always say there's the good fear that keeps you safe, but you just don't want to
1:16:52 Michelle Obama? overindulge the fear that keeps you stuck because fear can keep you stuck. Absolutely. There are a lot of people who
1:17:03 Michelle Obama? don't experience, don't try, don't grow because they're afraid of the unknown. And that can leave you in a small place because all the, all the good stuff happens on the other side of fear. When you, when you, you know, lean into it, get comfortable with it, know it's a part of the ride. If you can bear with that initial sort of the anxiety that comes with anything new and say, that's normal. It's normal that I'm starting something new. I don't know anyone and I'm, I feel a little anxious about it. Ride that wave of anxiety, but don't let it stop you because when you do, you miss
1:17:45 Michelle Obama? the growth that comes from taking a risk and pushing beyond the thing that makes you uncomfortable. Yeah. If you practice moving away from that fear, you just practice always feeling safe. But you'll look around and realize that you, you might feel safe, but you won't be happy and you probably have missed out on a lot of really amazing stuff.
1:18:09 Speaker 00 And you're not safe.
1:18:11 Michelle Obama? And you're not safe.
1:18:12 Speaker 00 Where you are, there is no, there is no bubble of safety because this is where you're from.
1:18:18 Michelle Obama? Yeah.
1:18:19 Speaker 00 You, you might as well have that experience because she said in her industry, right? So, yeah, she's not gonna make it out there in Texas.
1:18:27 Michelle Obama? Yeah.
1:18:28 Speaker 00 Doing hair for celebrities. She's gotta, she's gotta get to.
1:18:31 Michelle Obama? Gotta go where the work is.
1:18:32 Speaker 00 New York and Boston.
1:18:33 Michelle Obama? Yeah, yeah, so that's.
1:18:35 Craig Robinson? Yeah, that's great. Both of you have hit on some really good points. Fear is healthy.
1:18:43 Craig Robinson? And, um, and you can't let fear paralyze you so that you don't do anything. And the only thing that I would add, just to contextualize this for Amber, is that you're always gonna be nervous about the next step. So, take it so you learn what that feels like and each time it will be less fearful. That's what I've found. You know, the first hard pivot is the hardest. And then after that, you build that muscle and you're less afraid to try new things.
1:19:22 Speaker 00 Or at least it will remain consistent. So, I'm the, I'm the other part of the extreme. So, every time that I have to do stand up, I'm as nervous and direct as I was the very first time that I ever did it and got like every single. Yeah, so even though we're almost at 10,000 shows and my 23rd 100-city tour, like, that nervousness and the butterflies and it never has gone away. It's what allows me to realize something's counting on this.
1:20:02 Craig Robinson? Yeah.
1:20:03 Speaker 00 There's something on this.
1:20:04 Craig Robinson? Yeah.
1:20:04 Speaker 00 You must do well.
1:20:05 Craig Robinson? Yeah, you're passionate about it.
1:20:07 Speaker 00 Right, and, and you, you need that in your life as a barometer so that, so that you don't take things for granted. And, um, it, it's in no way should stop you. It should further, why would you be getting nervous for something that wasn't gonna matter?
1:20:24 Michelle Obama? That's right.
1:20:24 Speaker 00 If you're nervous and fearful, there's a good reason.
1:20:27 Michelle Obama? That's true, that's true.
1:20:28 Speaker 00 Still do it.
1:20:29 Michelle Obama? Yeah, yeah.
1:20:31 Michelle Obama? We like that. Well, hopefully, Amber, we wish you good luck.
1:20:34 Speaker 00 Right.
1:20:34 Michelle Obama? Um, keep, keep going. Uh, I think Kat said it right. You, you know, you're on the right track and we are all confirming that you are. Uh, so keep going.
1:20:44 Speaker 00 And we hope to see you in New York.
1:20:46 Michelle Obama? Yeah, and let us know, you know, uh, how it goes when you make that move.
1:20:51 Speaker 00 Right.
1:20:52 Michelle Obama? Uh, Kat, this, you, you know.
1:20:55 Speaker 00 My man.
1:20:56 Michelle Obama? You're a layered little dude.
1:20:58 Speaker 00 Right.
1:20:59 Michelle Obama? The layers of Kat.
1:21:00 Speaker 00 He has layers. Kat's like, I know.
1:21:03 Michelle Obama? Yeah, I know. Kat, thank you. This is, this was a real privilege.
1:21:07 Speaker 00 Thank you.
1:21:07 Michelle Obama? Thank you for putting us on your, your list, uh, making the time.
1:21:12 Speaker 00 Very short list.
1:21:15 Speaker 00 Most of my things are like that.
1:21:18 Michelle Obama? Say you set them up for that.
1:21:19 Speaker 00 That was the king of the short list. Point guard, right, alley-oop. The southest ghost. Yeah, no, I really, I really appreciate the opportunity that you both are making for yourselves and for others. Like, this is really a big deal.
1:21:37 Michelle Obama? This has been a treat. You are truly a gift in more ways than one. So, uh, thank you. Kat Williams, thank you so much.
1:21:46 Speaker 00 Thanks, man.
1:21:46 Michelle Obama? Everybody, give it up.
1:22:16 Speaker 04 I'm Emma Greed, host of Aspire with Emma Greed, the podcast where I sit down with people who don't just dream big, they build big. If you love Michelle and Craig on IMO, just wait until you hear their episode on my show. Michelle told me about the moment at 26 when she lost her father and her best friend in the same year. It made her walk away from her corporate law career to figure out her why. That's the kind of conversation you get on Aspire. We talk about mindset, ambition, and doing the work that actually moves the needle. So if you're ready to raise your standards and take charge of the life you're building, Aspire is where you start. Follow and listen to Aspire with me, Emma Greed, available wherever you get your podcasts.
Previous IMO Presents: The Look Live with Wesley Morris Next Hold Space for Grief with Anderson Cooper Page updated October 31, 2026 · transcript and summary are machine-generated
