Aspire with Emma Grede - Aspire with Michelle Obama and Craig Robinson: The Power of Knowing Your "Why"

Episode Date: June 24, 2025

Emma sits down for an intimate, inspiring conversation with former First Lady Michelle Obama and her big brother, Craig Robinson. In this special episode, Michelle and Craig open up about family, leadership, and the values that shaped them, from their early years sharing on Chicago’s South Side to the White House. Michelle reflects candidly on balancing motherhood, public life, and personal ambition, while Craig shares heartfelt stories that highlight the emotional intelligence and unwavering support they learned from their parents. Together, they discuss how everyone can create meaningful change—starting exactly where they are. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

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Visit emma greed.com to purchase the book, also available on Amazon, your favorite audio platforms, and all good bookshops. On today's very special episode of The Aspire podcast, straight from Washington, D.C., we're getting ready to learn some life lessons from two of the best. Former First Lady Michelle Obama and her big brother, Craig Robinson, have inspired millions. And now they're sitting down with me to open up about the biggest takeaways they've learned along the way. If you're thinking about how to give your life more meaning or what really matters, this is the episode for you. Study and play. Come together on a Windows 11 PC. And for a limited time, college students get the best of both worlds. Get the unreal college deal, everything you need to study and play with select Windows 11 PCs.

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Stop taking bad travel advice. Start comparing hundreds of sites with kayak and get your trip right. Bad advice. You're talking to me. Kayak. Got that right. Craig, Mrs. Obama.

I am Michelle. Thank you. Can't say Craig. That sounded odd. First of all, thank you for that because I have a lot of Mrs. Obama, Mr. Obama, Mrs. Obama, all through my thing.

I was not going to take the liberty. So thank you for that. I was ready to Mrs. Obama while away through this whole thing. I wouldn't have let you do that. I would not have let you. She might have kept it. I mean, listen, she stopped me straight away, which I'm very, very grateful for.

Thanks for happiness. I'm so happy to have you. I'm extremely grateful for the time and extremely excited to have this conversation. So we're here. Well, this is family here. Thank you. So we are happy to be here. You've been such a support to us, the foundation.

You are amazing. And we're so proud of all that you're doing here. So we are thrilled. I will speak for my brother. She is as she wants to do. Well, that means the most coming from you. And we can just finish now because that's all right. I am honestly, it's just been so wonderful.

Even doing the research about the two of you, because I have to say I always wanted a big brother. I'm one of four girls. I don't, sadly don't have a big brother. But just hearing more about your relationship and the way you describe your relationship is just so beautiful. Like this idea of you having a protector. I think you said someone,

where, you know, you feel like he's always got your arm, like he's always carrying you, has always got your back, which I thought was so lovely and so wonderful. Isn't that so nice? But as siblings, you know, we spend so much time together in our childhood. And I know that at some point you guys shared a bedroom, which I did with my sisters. And it gives like a different type of intensity to your relationships. And then, of course, we grow up. Life happens.

You go off and you do different things. And so my first question was really to ask both of you, how do you think your parents would feel about the two of you working together now and doing this new podcast. That you hit us right in the heart, right? Right, right? Really. Well, you know, our mom, it's a year since her death in May. I'm so sorry.

And I think one of the reasons that inspired us to start IMO was it was a great way once Craig and I realized that we are the elders now in our family, losing our mom. and we've lost a lot of the seniors in our life, that our generation is now the generation with the wisdom. And, you know, when you lose your mom, you have to start embracing the truth of who you are. No longer are you somebody's daughter or son, but you are the person that people are looking up to in your family,

even though maybe that was the case long before because of our positions, but you don't feel it. So this podcast is kind of a tribute to our family, our parents, a way for us to spend time together, to make it a point that we're spending time together, but also to share a lot of the wisdom that Marion and Frazier Robinson passed down to us around a kitchen table that got us both where we are today. So I know they would be proud. And they both would be cracking up too. They would, I think they would find it humorous that the two of us are sort of back in each other's lives like this.

So, so closely. And I would just love to hear mom's reaction to some of the things, some of the topics we talked about. Do you think you'd get every episode feedback? Is that the type of family you come from? Oh, yeah. Yeah. I think, especially our mom.

My mom would be like, well, I don't remember that. Actually, she would claim not to remember anything negative and remember all of the things positive. I love that. Well, you know, I started this podcast because I really wanted to speak to the people that I aspire to the most. And Michelle, I mean, it goes without saying, and probably for half the people on this planet, you are one of the most inspiring individuals ever. Thank you. I wonder who the two of you aspire to. Oh, I'll go first on that one, seeing how we were just talking about this. You know, when I was little, I looked up to my dad. He was a little. He was. the guy I looked up to. Now, there were, like most boys, I had sports figures and entertainers that you were like, oh, I wouldn't mind doing that. And I wouldn't mind being Ernie Banks from the Chicago Cubs. But, you know, our dad was such a positive force in not just our lives, but anybody's life

that he touched. And I really admired that about him. And, Emma, you probably know, he had a disability. He had MS. And I just, to me, it just made him even stronger because he got up every day and went to work. And when he came home, you know, Mish and I were just talking about this. He would sometimes come home and just get in front of the TV. But if we were outside playing, he'd come out and play with us, even after he was working. So, you know, I really aspired to be the type of dad that I had. that I had. So that's who I looked up to. Yeah. And I think similarly, instead of aspiring to people that

I don't know or didn't meet or haven't met, and I've met a lot of people over my life now, I think it was the people in our orbit. I mean, we came from a working class, lower middle class background, big family, but we had a lot of people to aspire to. You know, my great Aunt Robbie that I talk about in becoming who taught me how to play the piano, even though we were combatants at it. But she was someone in the community who was a real force. She taught piano lessons to the kids in the neighborhood. She ran what was called an operetta workshop where inner city kids came to the basement of a church and learned opera and singing and using the recorder. We learned how to enunciate, how to perform. In the basement of a church, she was the musical

director. She was a elementary school teacher. You know, we had people in our lives like that. Real live role models, other teachers in our lives that I think really left an impact and made me want to probably set the stage for me mentoring and understanding that I had an obligation in my life to do more than just make money or to work at a corporate firm. I think that those were the people who led me to feel like I owed more to life than sitting on the 47th floor of a corporate firm and making money working for corporate clients. It's interesting that that's what you both took from your childhood because I think when you grow up in somewhere like the south side of Chicago, I mean, I grew up in a very similar area in England. There was so much negativity around me.

I had a great family, but a lot of people complained a lot and they blamed a lot. And the sense that I get from the two of you is that while there was a lot of stuff happening around you, you were able and your family kind of created this amazing nucleus for you to, you know, feel like you should be mentors. How did like what was going on around you not seeps through into what was happening in your childhood? Well, I would say, see, we're older than you are. And it was a different time. And people weren't complaining. I don't remember people complaining around us. I actually, remember it being more of a village where a proper community. A proper community, yes. And I love that term proper. A proper community. But where you had your neighbors and your friends' parents and

teacher, everybody was holding everybody accountable. And I think we just are missing that these days for whatever reason. People are fearful of parenting somebody else's kids when their parents aren't around. But I remember our mom saying that we were not anything special in the neighborhood. I mean, they loved us and nurtured us, but she also felt that our friends could do whatever we could do. And the kids who were around the block who were single parent kids could do exactly what we could do with the right environment.

There was always the question my mom got when we were in the White House. How did you raise two successful, highly, you know, aspirational figures? And as Craig said, mom would say there are a million of Michelle and Craig Robinson's all over the world. You know, my mom understood that excellence wasn't because of your birthright or money or status. because she and my father, my mother didn't work until I went to high school. She was a stay-at-home mom. Our dad was a stationary fireman, worked for the city. He was a blue-collar worker.

But we came from a community of really smart people. They didn't have opportunity because of racism, but there was still a high rate of intelligence, and they produced kids just like us. And so there was a pride, you know, not sort of anger or, complaining, there was a pride and a belief that what we had was more than enough. And I think that's probably why our role models are the people that were right before us. Because, no, they weren't doctors and lawyers and successful politicians, but they were good people who cared about their kids,

who cared about their community, who invested a lot in the world. And I think there's still communities out there like it. I was going to ask you that. You do think because it's changed so much now, right? You mentioned, like, you know, that was a, it was a different time. And I think people really crave community. We also focus on the negative. And I think social media plays a role in that. Huge you so. You know, showing shots of kids getting shot down in, in, in neighborhoods is a lot more eye-catching than showing a bunch of kids going to school and doing their homework. And so I think a lot of communities get a bad rap because all you see. see is what's wrong. And we don't focus a lot on all that's right. I think Craig and I are living

proof that there is not, not yesterday, but today, there are a lot of right things happening in communities. We just have to continue to invest in them. We have to show kids that we believe in who they are, that we believe they have the skills. We saw it when we were in Malawi together, right? I mean, we went to one of the poorest communities in a poor country, and we saw dozens of girls showing up ready to learn. And they had less than any of us ever did growing up. But they had everything inside of them to achieve. Everything. You know, and we live in a world that stops believing in all kids.

We grew up in a place where everyone believed in all kids. And, you know, that's a message. This is what can be, this is what you reap when you invest and you believe in all kids, regardless of where they come from or how much money they come from. I was actually going to talk about it much later in this conversation, but because you talk about how you're investing your time, I'd love you to talk to me a little bit more about the foundation and the work that you're doing at the foundation,

because you've chose very purposefully with all of the things that you could do to invest specifically in and around leadership, believing in kids, believing in the good of people and what they're capable of. So why specifically leadership? It's leadership and it's more specifically young people. It's young leadership. So at the Obama Presidential Center,

which is scheduled to open in the late spring and summer of next year, and we are thrilled. It is not just a presidential center. Oh, no, it's not. It is an economic development engine on the south side, down the street from where we grew up, across the street from a public high school. I mean, how proud are you to have it there? I mean, so proud. I mean, we are, you know, our blood, sweat and tears, who we are, our foundation, our roots, everything that we are was grounded in that community.

And to be able to invest in that way of we are proud. But both Barack and I understand that change comes from the next generation. And we see it now. You know, if you overstay your welcome as a leader in any form, you don't make room for the next generation. And so Barack and I, in addition to both of us investing our lives in mentoring, we thought, well, we need to make room. You know, we need to use this part in our lives not to continue to build who we are, but to make space for those that are coming. and leadership comes from all parts of the world, all parts of the country. And we're trying to bring together not just young leaders from the south side of Chicago,

but from Asia and Africa and all parts of the world. And one of the things that young people need in leadership is they need to know one another. They need to be able to network. They need to know that they're out there. And these aren't just leaders working in community development or in policy. I mean, the young people coming out of the Obama presidential, Center leadership programs could be sitting in C-suits. They could be sitting in your seat. Yes. But the goal is to train them in a whole foundation of democracy and empathy and a whole

different definition of what leadership can be, not what it looks like today. Exactly. And I think that that's so clear. I mean, I spent time in South Africa with the foundation as well. And I'm a very, very proud member of the board. But what was so interesting to to me is looking at the Obama leaders is to see how varied they were. There were people working in reproductive health. There were people working in education. There were those working in climate change. And it was so interesting. I wonder what, you know, has made you, and of course, your husband and the team that you work with so uniquely positioned to tackle this issue. Like, what makes you able to take this on? Because it's no small feat. No, no. Um, you know, um, you

You know, look, Barack's presidency was the result of young people. You know, maybe it felt like it happened a long ago. But when Barack first announced, no one thought he would ever, the kid by the name of Barack Hussein Obama would ever be the first black president of the United States of America. And who believed in him first, young people. People in their teens and 20s, you know, they were using the early versions of social media, which was meetup. to develop their own. That was a long time ago. That was a very long time ago. When we entered the White House, we came with Blackberries. There were no iPhones. Social media didn't exist. Wow, that's crazy to think about. It came into being, we were all on Blackberries. First term, we were learning about Snapchat and

Instagram and it was all brand new. So the world was a world of young people. And so our field organizers, our, you know, our development folks, you know, the folks on the ground in that campaign that led to his win in Iowa and beyond, these were all mostly 30 and below, you know, young people. And so we saw firsthand the energy and the tenacity and the passion and the belief that young people bring to a movement. And so all those young people follow us into the White House. And so the eight years in the White House of learning about this country, learning. how to lead young men and women at the helms in all departments throughout the country.

And in my opinion, we had some of the best progress with a level of optimism and hope and inclusion because that's what you get when you work with young people. Oh, yeah. Well, and it had global ramifications. I didn't even live in this country at that point. And that was something that was felt globally. I mean, we would wake ourselves up in the middle of the night to watch those. speeches that had no bearings on what was happening in England, but it did. You know, the ripple

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Monopoly is a trademark of Hasbro. Hasbro is not a sponsor of this promotion. The start with yourself tour kicks off on April 15th in New York City. Tickets are on sale now at emigree.com. Ambition comes in all shapes and sizes. At First Citizens Bank, we roll with your goals because we're built for what you're building. Fit for your ambition for Citizens Bank. Craig, I wanted to ask you, I mean, you've got lots of great memories, I'm sure, of Michelle in the early years.

But is there something that you can share, like a memory that captures the essence and the core of who your sister is? Wow. I'm going to ask you the same questions you can get rid of. So this is the essence of my sister. Imagine for my birthday, it was probably my fourth or fifth birthday, and I get a brand new bicycle, two-wheeler with the training wheel. So I hadn't figured out how to ride a two-wheeler yet. And it was a really a real surprise. And I got my bike.

I ride it up in the basement. and who comes tooling around the corner on her tricycle happier than I am that I got a new bite was my little sister who couldn't have been more than four years old. And she was so happy for me. And that embodies what kind of sister she is. She's just caring and selfless and happy for other people's success. And I use that one as an example, but I could probably come up with five or six more of those

where she was as happy as I was for my success. Just a generous person. Yes. That's so sweet. You remember that? I do. I do. It's one of my favorite pictures of us,

me and my little favorite red velvet dress on my tricycle. And I'm looking up at him like, look at my big brother. He's amazing. That is just a sweet day. Do you have a memory of Craig that will tell me. me. I mean, that's one of the, I mean, that's what I thought of my brother. He was amazing. He was an amazing person to follow after because everyone loved Craig. I mean, deeply. And I would tease my mom.

I was like, I, first lady of the United States, and you still, you know, light up like a Christmas tree when Craig walks in, right? It's like, what more do I have to do? What are you going to do? Mums and sons. You know, it's true for me. I was like, hey, lady, you're living in the, White House. Whatever. You know, what else, I can't, I can't top that. My son is here. That's right.

It's hard being the favorite. What are you going to do? It's hard. But the thing is, is like, I agree. He's my favorite. He's a lot of people's favorites. And, you know, one of the memories of just our time in Princeton. Because we were at Princeton together.

You were? Two years. Yeah. Yeah. We overlapped for two years. How proud was your family? Yeah. Yeah.

Yeah. But my brother was big man on. campus, right? Because he was Division I-1 starter on the basketball team, all Ivy. So he was a big man on campus. And we weren't raised to be close, close, like,

up under each other. I mean, our mother was like, you have your life, he has yours, because he was the kind of person that would stop what he was doing to make sure I was okay. So my mother was like, you cannot worry about your little sister. You need to get on with your life. So we were together, but apart.

But the times that we were together, he would take me to alumni booster dinners, which were these free dinners at rich people's houses. And he would just bring along his little sister. That is really big. I never wanted to take my little sisters anywhere. My mom would be like, take your sister. I'd be like, oh, come. And my mom was the complete opposite. I was like, I got to bring her with, don't take her with her. She's like, no, leave her. But then he would bring me. And, you know, I could just bask in his glow. But my brother is a deeply kind, honest person who I can count on for anything at the drop of the hat. And in those White House years, just knowing that they would show up when we just needed some grounding in family, just regular old, where the girls needed regular old family, you know, not special people looking at them differently.

Just they needed to be reminded of who they were, where they came from. and having my brother and his family come around during those times what met the world to me and Barack. No doubt. It seems to me that your family are such a huge influence in your lives and the people that you've grown into being. And I just wonder if you've been able to like over the years and in hindsight pinpoint. Like what is the framework that you were given,

the tools that you were given have made you both so incredibly successful, but also just like have such an incredible family done. I would start with the fact that our parents loved us unconditionally. That was... You always felt that as a kid. Always felt that. Even if you do something really bad, you would like, knew it. Well, I never did anything bad.

You didn't? No, he stole gum off the teacher's desk. I stole gum off the teacher's desk once. And that was the worst thing I've done. But I can tell you, my parents made us Well, I did stuff to Mish every now and then. But our parents would even through all of that, our parents just absolutely loved us.

And not only did they love us, but we felt the love, but they always showed it. And that was number one. And then when you think about our dad who was disabled with MS, from the time we could remember he had, he walked with a limp that got progressively worse, he got up and went to work every day. He was such a hard worker,

and I think that drove us to be hard workers. So you're loved, and you have this great example of hard work. And then to use a term that wasn't around back then, our parents were really emotionally intelligent. Wow. And I think they imprinted that on. us and at least certainly I can see it in Mish all the time when she's dealing with people,

dealing with the public. Yes. And I feel it, you know, in coaching and I feel it, I felt it in leadership positions. And those three things are the things that I think about when you ask, what is it about our family? You know, it's interesting because we didn't talk about that and I'm listening to you. And I actually jot it down sort of, well, what are my? principles. And just listening to him, I wrote down, do what you're passionate about, do the best that

you can, be as prepared as you can, and operate with empathy. I'm so happy that you mentioned that because I have been thinking, you know, I'm like in this sort of interesting third chapter of my life and career. And I've been thinking a lot about, well, what do you want to do and what do you put out there? And for me, everything starts from like these foundational principles. And my team, because I talk about the principles all the time. They were like, what are your principles? And I told them, like, you have to do an episode on that. So I did like my first solo episode.

Oh. Very scared of, like, channeling my inner like Mel Bobbins here. And you're just talking with no one to talk to? Just with not, with no one to talk to. Because my studio would be. I would do that. It's really, it's really scary. You really test yourself.

But then I realized, I can talk for a long time. And they were like, all right, you're done. Cut. Get her out of you. But it was interesting because it really made me baked down. Like what makes me me and what do I care about? And that's why I wanted to ask you those things, because I think we all find you and your family so unbelievably fascinating. And when you see the dynamic between you two, it's so clear that there's just some foundational stuff there. There's just

stuff that you have that must have come from your parents, that must have come from your upbringing. And I love the fact that you talk about emotional intelligence because that wasn't a bedrock of my upbringing. I had to learn that and learn it the hard. way. But I imagine as parents, that's something that you were both acutely aware of and you've tried to give to your kids as a foundational principal. Absolutely. I mean, we spend more time talking about how you treat other people. I mean, I try to make it a point just as a parenting principle, not to talk about school and grades with the kids at the table. Because when you have an older one and one coming up, you don't know who the younger one is going to be. You're like creating a

dynamic. Right. You're creating the dynamic. And first daughter, brilliant, precocious. And so is the second one. But I was very careful to not sort of overdue, oh, you got an A. Oh, this happened. Oh, you achieve these things because I'm thinking emotionally, this one isn't even coming up yet. And what if that's not who she is or who she wants to be. And if she sees us falling all over the first one for, you know, things, what does that tell her? Yeah. And how does it change the way she behaves without you even knowing because she wants to please you? So we spent more time talking about what happened at school, friendships, how did you feel?

Because I felt like that was more neutral territory, you know. Let's talk through problems. You know, okay, great, you're doing well at school. That's for you. Good for you. But it's not, you know, it's not the basis of our dynamic here. So I... And what did you care about? Like, when you think about, like, one of the things that you were like, but this is a must do in this house? Kindness, self-possession. I wanted my kids to... I wanted my kids to be okay with speaking up for themselves, but not. by putting somebody else down. I wanted my girls to know how to fight for themselves. I wanted them to know how to advocate for themselves,

how to communicate, how to deal. And how did you even teach that? Oh, my gosh. You know, I think for us, it's a lot of talking to your kids. I mean, when we talk about the kitchen table, part of IMO and we sit around a table is that, We spent our time. Our house was so small. Everything happened in the kitchen table. You were like condensed. That was the place. And everybody in our family, extended family, they came and we sat around the table and we talked about everything.

We heard about our uncle's exploits at work. He was a detective and he would tell long stories about cases he was on. And everybody was a storyteller. And everybody was sort of putting their lives and their issues on the table. and the kids were allowed to be there. Exactly. You had a lot of exposure. So witness and no one was shushed. Like if you had a question and if you had to be polite about it, but you were a part of the conversation. And our parents more so than anyone in our family encouraged kids to do that.

And so I wanted, I think we both in our households wanted to create that same dynamic, a voice, right? Because that's where you practice empathy. you test out theories, you come home, something happened at school. And we're going to talk about it. Because we talk us, that's what we do. We're not going to solve it for you. But we're going to talk it through and we want to hear, well, what would you have done? And why did you do that?

What did you think about that? I mean, practicing almost scenarios in a way, real life and imaginary scenarios. And it's the conversation and the patience and something that we lose when everybody these days separates into their own rooms and their own phones and their own devices or their own devices or when parents don't share things with their kids you know i often hear especially because i've moved to l.A it's like that that's not a conversation for a kid you know and i was brought up again much like you just hearing everything the good the bad the sighting and a program if something happened at a family dinner somebody had an argument or somebody said

something crazy maybe we wouldn't talk about it then but in the car ride home We feel like, well, you were talking about it. Tell us about what Aunt Such and Such said. Can you help us understand what's going on? So I think helping, giving kids credit for understanding context, you know, not dumbing things down. You know, not having conversations that are too above kids. Inappropriate. Yes, of course. But taking children's curiosity, not as disrespect, but as an opportunity to teach. Yes. You know, my mother, for example, She used to tell the story about Craig, you know, when he was a baby, that when he was learning how to do some things, he would get on the couch and he wanted to get off on his own. And instead of stopping him from doing it, she said, I took the time to show him as early as two that you could turn around, scoot yourself down, and get off the couch by yourself. So instead of telling him, don't get off the couch, you're too young, or be careful. She was like, let me teach him. And she always talked about how smart kids were, how smart babies were. She was aware.

She was an early childhood development protege before it was a thing. She was very into how kids, children, babies thought. And she understood that they were smart and that they had ideas very early on. That's all emotional intelligence. Yes. And I think like that. I think like that about my kids. I think about that about my staff and my people. My whole question in life is, why are you doing what you're doing? What may you say that before I react, I think what's your context? Do you think that that is a good conversation that people should have with themselves? Because I feel like it's one that I'm having constantly with myself right now. Like, why am I doing what I'm doing? And what is the point of all of this? And so, going back to your principles, it feels like you guys were raised to question yourself. To have the emotional intelligence to go inside yourselves and figure it out.

Yes. Our mom was really good about saying, you tell me why you want to do something. It was so it was you had some agency in anything you wanted to do. So if I wanted to, if I wanted to go over to. a girl's house and we've talked about this before, she wouldn't say no. She would say, well, what do you think? And you imagine how much pressure that puts on you? Especially when you go to your parent and you say, what do you think is the best? And it's like, I just want you to tell me. Please. Just tell me the right answer because I don't want to mess this up.

And that kind of agency gives you confidence. Yes. To make good decisions. no matter what the situation. And another point that Mish mentioned, she mentioned empathy. My mom was the type when I would, she would come to our school and help out early before people really did that. Before there were room parents. Before they were room parents, she would just come, she knew how hard a teacher's job was, and she'd come and offer some help. And she came to my class once, and I got my work done, and I was walking around talking to other kids.

And my mom said, well, what are you doing? And I said, I'm done with my work. She said, well, why don't you help somebody else who needs help? And it never had crossed my mind to do that. Well, you're a kid. Because I'm a kid. And I think being a good leader, you have to have empathy for the people you lead because their upbringings aren't the same as yours

and their experiences aren't the same as yours. but if you can contextualize why they're doing something to Michelle's point, you'll be a better leader. No doubt. It's such a, it's absolutely true. I mean, I feel like I'm in constant conversation thinking about that all the time. Like what is happening for this person that that's the reaction? How can I see it from their point of view?

And again, it comes from a place of empathy. You have to be able to see it from their point of view. And the questioning that you were mentioning, the constant questioning, yes, that's what we were raised to do, to always ask our own why. So when I was my first job out of law school, of course, after graduating Harvard, as I wrote about, I did what all Harvard grads did. I started working at a big corporate firm, making as much money as I could. You were just on a trajectory. I was on a trajectory. I was checking a box, not questioning, because I was on my path.

And also because it's like you just come out at Harvard. You're like, I earned that too. So I'm going to do that. I'm going to take the check. I also had a ton of debt. Yes. You needed the money. I needed the money.

But I talked about one of the turning points, early turning points in my life was when I lost my father. And then the same year I lost one of my best friends to lymphoma. First time I had lost people close to me in. And you're 27 at this point? 26. Young. Yeah, young. Yeah.

And I had to look at myself and say, is this who I am? I mean, did I do all of this to just work in this firm? And there's nothing wrong with working in a firm, but I hadn't questioned myself. I realized that I needed to figure out my, am I here for the right reason? And if I'm not, what else can I be doing? And have I, if I tried anything else on before choosing this? And I think it's that that helped get me into a career of service. Yes.

You know, and I don't, I probably wouldn't have done it. My parents weren't questioning me. They, they supported every, you go into the top law firm. Exactly. Everyone's like, you've done it. You made it. And they didn't know what else you could be. I mean, we had already kind of surpassed them in terms of education and experience, right?

So they, but they were still mentoring us through this action. of showing us how to continue to dig inside and figure out our why. And I am doing that every day. That was my next question. Do you still do that? Do you feel like it happens with like frequency in your life? I'm at another why point now. I mean, you know, that's why I tell people you never stop coming. You know, here I am. I 61. Am I 61? Are I 61? Thank you. You know, I'm sort of like, How old am I? I'm 61 years old. Have I done enough?

Is it time to stop? You ask yourself that? Have I done enough? Oh, yeah. I'm in therapy, you know, trying to figure out why do I keep asking myself that? But I'm 61, but I'm only. What do you keep asking yourself that? I haven't.

She's driven. There's a drive and there's a sense of responsibility. There's probably. a bitter survivor's remorse, you know. There's also just a truth that there's so much to be done, you know, that it's hard for me to look at problems and not figure out what can I do to solve it. Is that a burden for you? Yeah, it is.

Do you have the same feeling? So I don't, and the only reason I don't have it is because I'm still raised, my wife, Kelly and I are still raising a 15-year-old, a 13-year-old. You have four kids, correct? I have four kids. Two that are grown-ups. And then two, 33 and 29, and then 15 and 13. So going into the sophomore year and going into the eighth grade.

Because you know I have four too. I know you have four kids, isn't it? It's a lot. Let's have a sympathy thing right now. We went two and two. So what you're doing is actually harder. Then you smush them all together. You smush them all together.

And you have twins. You still have some of the stuff. Yeah. Emma, you haven't thought about your wife, you know? After two, I was like, what's my wife? I'm running two companies out. I'm like, why? On the board of the foundation?

You guys, wait, why? I'm like, ma, ma, ma, why am I doing this? Is the question. Emma, are you driven? You know, I had good role models. Let me tell you what you did. Like, you fired up every woman on the planet. And I think that that's the truth because, again, living in England, you know,

there were just women. And I've spoken about this so many times. It's not just because you're here and I want to kiss some ass, but it's the truth. You know, like Oprah for me was like the one. You'd come home and I would run home from school because Oprah came on at 3.45. And so I would get my fix and I would like, you know, I learned about gratitude and I learned about like the, you know, the good stuff that I wasn't seeing around me. Like community, empathy, how do you take care of people?

What does mindfulness mean? So I learned all this stuff. And throughout my life I feel like people have appeared, right? So kind of show me the way. And, you know, for so many of us, we saw you and we were like, wow, she's a lawyer and she's so accomplished. And now she's going to take on this whole situation around what everybody's eating. And then she's going to be out here speaking and look at her arms and look at her outfit.

And she's so good. And it was like all the things. And so in my head, I was like, well, of course I can. And I think that that's so important because I truly believe you can't be what you don't see. That's for one of my biggest reasons for wanting to so bad be on the board of the Obama Foundation. And I made no secret of it. I told everybody else. What about me?

I can pull myself up for that. But, you know, for me, again, it's about this idea of what are you putting out there and how many people can it impact. And I feel like in both of your careers, you haven't just settled with making something great for yourselves and making something great for your families. But you've got, had these kind of like huge tentacles. And that is really admirable. And I think that, you know, the right age of 42 right now. Now, you start to think about a lot of things beyond yourself and beyond your own family. And that's why for me, it's so fascinating that at this point in your life, you two have chosen

to come together and share all of this golden stuff because it's what the world needs. Like, we need to hear that. I need to understand your principles. I want to know, like, how I should raise my kids. I want to know, like, what you did wrong, quite honestly. I want all of it, like all the information. So we are, like, eating it up right now, like taking notes literally all the time. time. And I feel like your whole family and the way that you guys are is just a big,

beautiful lesson for all of us. So we should be so lucky. I really feel like that. And it still goes back to what our mom said, because he quotes it a lot, we are not special. There are millions of Michelle and Craigs out there. You know this too. We are not rare. It's just opportunity, luck, we happen to have two good parents. You know, our souls are the same. Our intellect is the same. But when you luck up on two good parents, lock up, you know. It's a big deal. So, yeah, I feel like I have a responsibility to the millions of other Craigs and Michelle's that are coming up that may not get that lucky piece. And for kids like us, you know, you don't get it all. You miss a piece.

And the trajectory is intense. There's no room for error for kids like us. And it really makes me emotional, you know, because I think of one step away. And, you know, this guy could be seen as a criminal, as somebody who's dangerous. One step away, I could have been. you know, somebody who could have never gotten into college with the same mind,

the same possibility, the same art, the same soul. So I do feel a responsibility to cast a broad net and to be the light for somebody, you know, some kid like me, you know, who didn't have the right mom, didn't have the right mix. Things just didn't work out perfectly for us. And this is what I want this country to understand. It's like, life is unfair for a lot of kids. There are no safety nets for many of us. We provide that safety net for each other through our taxes, through our giving, through our empathy, through our openness, especially when you have enough, when you've been blessed with plenty. Our responsibility, our principles should be, how do we spread that? Because guess what I've learned? There's enough for me to have a lot because I've had many careers.

I've made money. I don't believe in not making money. Thank you. But I also... It's nice to you to say that part too, right? Because I don't think it's either or. It's not either or you can do both. You know, you can make a lot of money.

You can pay your fair share of taxes. There can be a good social safety net. You can have good insurance and everybody can have good insurance. You know, we can all... There's plenty on this place. planet to go around and it's not a zero-sum game. And so that's what keeps driving me is like, to whom much is given, much is expected, you know? And we're a great country where many of us have been given a lot and there are a lot of people within our own midst who don't have enough.

And it's not because I'm special and they're not. It's not because I worked harder and deserved it more and they didn't because I know who those people are. And they are not. all the same color as me. They come from all walks of life. We can't make assumptions about who people are and what they can do based on the color of their skin. There are well-deserving poor people in Appalachia and they're well-deserving poor people on the south side of Chicago and all of them are not getting a fair shake. They don't have good enough schools. They don't get health care. And I feel it is our responsibility not just to have principals for our own individual cells,

but have principles that are going to impact a broader squath of people because it makes us all better. Oh, yes. And that really does. That's the thing that keeps me pushing forward and feeling like, have I done enough? How many discounts does USA auto insurance offer?

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I really believe that to my core, but I don't know where to start. work my regular job, I'm pretty okay. Like, how do you start to extend yourself and have a broader impact if you want one? Well, one of the principles that I talk about in the light is start small, you know, the power in small change is really real, you know, and sometimes we get ahead of ourselves because we think it has to be big. And look, not all of us will ever have the platform to have big impact. And that's okay because big impact is limited.

Look, I lived with the president of the United States of America. And there were so many things he couldn't get done because there are limits on that power. And as we are learning, it's good to have some limits on power. You know, it's good to have a democracy with checks and balances. There's a reason for that. But I also think that like a teacher, being a good teacher, that's some power.

Being a good parent to the children you bring into this planet, small right there in your lap. Right there, in your house. It's like, don't, you don't have to do anything else, but raise the kids you brought into the world. That doesn't mean you have to be rich. That means you have to be present. And proper.

means you have to have some theories of your why. You know, it's not just why do I want to be important. It's like, why do I want to be a mother? Why did I bring this kid here? And now that they're here, what's my responsibility? I would just say to people, focus right in your lap first. Take care of the thing that you have control and power over. And sometimes it's as small as yourself. Like, that's, like, if you can rethink your why, it might just be yourself. It may be. It may be. be yourself, wonder, well, why you're angry? Why don't you want to give? Why are you mad? What are you mad about? Where's that coming from? So I just encourage people, start with what you can control. Don't try to change your community. Do you have a little cousin who's looking up to you? Do you have a

neighborhood kid down the street from you who looks up to you? We all have someone looking up to us and living a life where we're a role model to those people in small ways, being good, going to work, being responsible. It doesn't mean you have to be an NBA star. Doesn't mean you have to be Steph Curry. You don't have to be Michelle Obama to make change. You know, it starts right here. And I would encourage people start small. Start where you are.

Start right where you are. But just be really committed to it and passionate about it, right? Don't half acid, right? That's a really important thing. If you're going to mentor a kid, do something small and do it for real, for real. Then do it for real, for real. If you're going to be in somebody's a kid's life, then be there. You know, you don't have to be perfect in it.

You don't have to be there every day. But when you say you're going to do something for a kid, then do it. Yeah. And if you can't do it, then don't say you can. That's another thing we learned from our parents. They didn't, they couldn't give us much. But if they told us they were going to do something or be somewhere, they did it. You know, they didn't lie.

It's the same where I come from. If you're from East London, like your word is king. Is your bond? Your word is your bond. Yes. You know, and if you can't do it, then say you can't. Honesty and your word, our father couldn't give us much. But he showed up whenever he said he was, he was consistent.

So I picked a man like my father. Barack Obama is a consistent man in my life and my daughter's life. And when he says he's going to do something for us, he does it. My brother, consistent man in my life. you know, small things. You know? Craig, did you have the same type of like important people

in your life outside the family? I mean like mentors or somebody that helped you out in that way? I did. I did. It was my extended family. My dad's younger brothers who were closer to us and age than he was to my father.

There was a gap in there. There was a little gap in there when they... I love the young uncle. They were the most fun. Oh, God. They could do so much good stuff for you. And so this was during the time of high black activism. Right.

Black Panthers, that kind of thing. And they allowed me in that world at an early age, you know, 10, 11 years old. Did you have a natural interest anyway? I had a natural interest in anything they were doing. Okay. So it's more about them than a cause at that point. That's how I looked up to them. Because one was an athlete, the other.

was a bookworm. And I wanted to be like both of them. They taught me how to stand. Even though my sister doesn't agree, they taught me how to talk to girls, even though I didn't put it into practice until later. He was too busy playing basketball. He was on the court. Taking your time. So it started with them. And then it moved on to basketball coaches. I had a couple of really good young basketball coach. Johnny Gage, who I thought was older than I was, ended up being closer to me and age. We were like 12 and 11 and 12, and he was 19. But he was, he held us accountable.

He was fair and he cared about us. Do you remember any of the advice that they gave you? My uncles said whenever you're standing on the street, never stand with your feet together. always stand with one foot pointing forward and the other foot pointing at 10 o'clock. Why is this? Explain this to me immediately. No, they didn't.

No, listen. Is someone coming to push you? Like, is this an attack situation? This wasn't. This turns out to be really true because you do public speaking, right? Yes. When you have to stand somewhere for a long time,

if you stand with both of your legs under you, you can't stand as long as you can. if you stand at 12 o'clock and 10 o'clock. They were right. Is he, is he? They were right. He's true about the advice. Is that an elegant stuff?

Like, yes, that's a man thing. It's a man thing. That is not a God. We cannot take that on. It could be a man thing. They didn't let me in the room for that lesson. That was something that stuck out in my mind for a long time. And then, of course, coach is giving you an advice about how to play.

And then other people outside. side of my dad. So I just, it's, it's mostly uncles. It's a lot of man advice stuff. Yeah, but this is I mean, the men need different advice. Ain't it the truth? And we were just in a discussion about how we don't, we didn't get any inner advice as men back then because, you know, it wasn't the thing. It wasn't a thing. They were teaching you how to stand. You know what they were doing? They were teaching you how, they were teaching you how to be a leader. That's what, I mean, Under a male and under a male paradigm. Of course.

Well, it is so different, isn't it? I mean, you have to do things very differently as a woman. There weren't women leaders back then. That's true. She's 61. I'm 63. Back then, the only female leaders you saw were in the classroom. Is that true?

Just think about it. It was very few female police officers, firefighters, very few women in leadership positions. and they had to be in the church at the choir. You saw people in those six categories in the education field, but you never saw them in. This is why we're in the mess we're in. My dad would take me to his job, and there were no women there. But, you know, there were a lot of people outside of my parents

who sort of showed me the way. Michelle, I wanted to switch gears. a bit because I was looking back at your career and all of the chapters that you've had. And I wondered if you ever thought about where you might be now had public life not intervened. Yeah. I mean, I probably, and public life and Barack Obama hadn't intervened, right? Because I was on my box checking path. Just like, because when you grow up in a working class family, we didn't have, I didn't have parents who could

show me what was possible. You know, my mom used to joke after I was 10, she was like, well, you're on your own kid. So meeting Barack was someone outside of the box checking paradigm, right? He had been a community organizer before he went to law school. He had taken a gap year. He had worked in bank. He had done so much. And he wasn't interested in the typical trajectory. So when I was also starting to ask this why in my career, it was around the time. that I met him. And he opened up a whole world of possibility of how to think about life. So, yeah, if I had met him...

Do you think he changed the way you thought about what you were going to do? I think he gave me courage to take the step away. I think... How did you do that? You know, because we had started dating and there was also the question of, how do I afford to take the step away, right? Because you're making good money. And I still had debt.

I mean, our combined, our student loan debt was more than our first mortgage after we got married. And because we didn't stay on the monetary path, we both went into public service. We didn't pay off our debt until Barack wrote dreams from my father and became a bestseller. Right? We would, you know, this is the massive amount of student loan debt that we had. We were in our late. late 30s, 40s, right? Because we got off the money-making path,

and I worked in the city, and every job I took, I made less money, but I was more and more fulfilled. So I think had I not met him, and his view was, we'll figure this out together. We got each other's backs. I think that was the first step into,

let me give this a try. No way. And it was that. You disagree? What do you mean? Please tell us. I love my brother-in-law. She would have made that move eventually herself.

You think so? Because we all have that thought process. She would have developed the courage to make it on her own. Perhaps. But the question was, where would I be? I don't know. I mean, maybe I would have taken the leap. But if I couldn't afford to, right?

If I found myself still struggling to pay my bills, I might have gone back. I might have gone back because I might have been like, you know what, I'm struggling with this lower salary. I wouldn't have been as happy. Yes, no doubt. I wouldn't have been as fulfilled. I wouldn't have felt this level of purpose. I mean, with every job I took, I was going deeper into my own community, my own city, learning it in ways that I never knew existed.

I mean, I feel like I know Chicago inside and out because. through working for the city and the Department of Planning and Development, working with the mayor, running a nonprofit organization. I have literally set foot in every community in the Chicago land area. And most people don't do that.

Most people live in their communities. They're born and raised. If you're born and raised on the south side, you don't know what the north side is. You never go to the west side. The world of the city opened up to me. And so it made it easy then to try new things. it prepared me to be the first lady of the United States because after doing all this stuff

outside of law, being the first lady of the United States was easy in comparison. You know, I had started nonprofit organizations. I had worked in city government before where I had to start stuff from scratch and work on projects that I knew nothing about and had to learn on the spot, you know, learning how to build teams and work with teams. So by the time I got to become the first lady, it, was like another startup, nonprofit, you know, where I knew how to define a mission and a vision and how to develop a strategy and build a team and to execute against a set of goals. I mean,

that's how I approached my eight years. It was like, it's a business. It's a business and we are going to get things done. We're going to understand our mission. We're like a small subsidiary within this big, you know, administration that is run by my husband. So I had to think and terms of strategies and initiatives that would complement what he was doing and not compete with what he was doing. And I had to do it with basically no staff because the first lady doesn't have a budget. I was used to that. I worked in nonprofits, you know, where you had to raise everything. You know, to figure out how to, you know, cross over into other agencies and use their resources to get things done in healthy eating. I mean, it was an entrepreneurial and very familiar

endeavor. Were you able to do forward planning? Like, could you look beyond the eight years and say, okay, here's what's going to happen the minute I'm out of office? Well, that's where the initiatives came in, right? So with let's move, for example, we established a separate nonprofit organization, the partnership for a healthier America, knowing that there had to be a place for this work to go once we were out of the White House. Because it's that important. It's that important. It's that important. And it wasn't going to, it wasn't going to be solved in eight years. And as we saw, once I got out of office and there wasn't a push, you know, food companies started renegan on what they were doing. And things start to roll back.

Start to unravel. Exactly. The partnership for Healthy America is a separate nonprofit that exists today. I'm an honorary chair, but I don't run it for our girls' education initiative. That's where the Girls' Opportunity Alliance was. developed because I knew that was going to be worked that would continue to happen in a nonprofit way. So my point being is that everything had to have a future when we started it, right? Because it didn't feel to me like it made sense to start an initiative on issues that couldn't be

solved in one or two terms, which is no issue. There's nothing that you can work on on the planet. Yes. Which a lot of people don't understand. That's going to be, which a lot of people don't understand, that's going to be resolved in a presidential term. No. Or two. Change happens over generations, right? And that's also something. Whether we like it or not.

Whether we like it or not. You make a forward movement and then a step backward and then three steps forward and then ten steps backwards. And you're still moving forward, right? But it doesn't happen all under one president or one first lady. You know, so all my initiatives were like, yeah, we're going to get this started, you know. But it's got to. to be finished on the outside. You've got to pass the baton where leadership comes in, right?

Why do we have leadership? We need people we can pass the baton too. We can't keep doing this. You know, we get to an age where our voices aren't even connected with what's going on. I'm 61. Yeah. I'm not 40-something. And it's okay that I don't know everything or don't understand. Pass the baton. Pass it. Pass it over. Emma. Let's go. It's your turn. You run, girl. I'm like, let me go. Let me out of. You know. You know? And so we don't want to compete with young leaders. No. You want to enable them.

Absolutely. I want to get out of the way. No, but you built this incredible foundation for so many people to be able to do this important work. Craig, I wanted to ask you, I wonder if there was ever a time, given Michelle's public prominence and what happened, because she's still your sister as all this is going on. Was there ever a time that it impacted you personally or professionally? and just, you know, because I'm somebody who works with her husband and I've worked with my other family members in the past, did you ever stir feelings of envy or jealousy? Did you ever have any of that? No, I thought you were going somewhere else with this question. No.

Well, I'll answer that one then. No. Give it wherever the tea is, I'll take you. So, never a feeling of envy. Okay. Where I thought you were going with that was, was there ever a time where, her success or their success bled into what I was doing in a negative way. And it was all the time because half the people didn't like them, right?

Which made them not like me, you know? And I will tell you an example, how I knew this. I didn't really pay attention to this until I was on the plane with the athletic director at Colorado, which was another team in our league. I coached at Oregon State. And she said to me, she said,

Craig, I don't know how you do it. She said, you were in our arena, and I watched your every move, and every time you stood up to say something to the referees, our whole crowd focused on you. And I was like, yeah, I get it. I get it. It's because of them.

But most of the feedback because of them was positive. So I was never envious. Are you kidding? I was riding the wave. I was proud. And they're such likable people, right? I felt like you felt. Like I felt like...

Inspired. I was inspired. And I knew firsthand. that what they were doing was they were trying to do the best for the most people. Yes. Not the best for them. No, for the most people. Or not just the best for our side, but the best for everybody.

And that's just admirable. So, no, I never felt envious or jealous or that's an interesting question. I don't know if anybody's ever asked me that. I don't think anybody said that. Well, because a lot of families, you know, with success. Yeah. I mean, they do. They get envious. They get jealous. You know, one makes it. They have to feed everyone else. It starts to get difficult. Listen. I, and...

Just saying that maybe that happens in some family. But, you know, we joke all the time. She grew up as Craig Robinson's little sister. Yes, fair, fair. And now I'm Michelle Obama's big brother. It's so true. It's time. It's time. It's time. It is complete payback, but I got the better of the deal. Thanks. I'm just going to say. You may have. Michelle, what I wanted to ask you, because I think this is so critical for this specific audience, so many women feel such unbelievable pressure at the time in your life when you were in the White House in those years, when you are having to balance raising a young family, you know, being a wife to the leader of the free world, to, you know, your own career ambitions and all your own aspirations as well.

And I wonder if there is like a critical and honest piece of advice that you can give or that you can share based on your own journey and what you would say to women that are trying to seemingly have it all, do it all, live to the fullest. All right. Well, I've said this a lot. It's impossible to have it all. So stop with that. First of all, you can have it all over a period of time. but this impatience and this feeling of like, I've got to be, I've got to have the exact job at the top of the game. And I want to be the best mom to all to the, you know, I want to be there, be at all the stuff. And I want to look my best and be in my best shape and be emotionally intuned. La la la la la. And my marriage has got to be on point. Like it's, it doesn't, you can't do all of that. There are tradeoffs.

And it's okay. you know, if we're blessed and we can take care of ourselves emotionally and physically, life is long and you can have chapters. And you don't lose out because you didn't read the whole book in one sitting. Each chapter can be really special. When my kids were little and I was sort of ready to drive in my career, but Barack was a state senator and then he ran for Congress. and lost, and then he was a U.S. Senator, he was away more than he was home.

I got to a point where I said, I can't be in the highest driving point in my career life. I just can't. So I left running a nonprofit that I enjoyed running, but running a nonprofit is an all-consuming, and it's, the nonprofit didn't have a lot of money, and I needed flexibility. Did you do it happily? Or was there resentment there? There was a little resentment, but I was happy because I love my girls and I love the time that I spent with them. And I felt more at peace with that decision because it was the right thing for them. And ultimately for me, because it gave me balance that I needed at that time. And I used myself as an example.

I did that and it didn't stop my growth. It didn't, you know, I went on after that. I became an associate dean. I was the vice president and head of community outreach for the University of Chicago hospitals. As the girls grew and I felt more secure, I started re-aligning myself. People don't realize they can take a little pause. Yeah. Like life doesn't really give you the feeling right now that you can just be like, hold, please.

That's right. For whatever reason. And you can, and you don't have to stop. Like, I didn't stop. I thought about quitting completely. And then I got an opportunity to get a good job that I enjoyed in a flex situation. I negotiated flexibility for myself. I negotiated flexibility first.

That wasn't flexibility. It just was less pay. And I was irritated at that because I got half the salary and was still doing a full-time job. So I learned from that. I was like, never again. I'm too much of a driver to ever get paid less. Right. So the next job I was like, pay the full salary, but give me hard blanche over my schedule. I will get the job done. But I'm picking up my kids from school. I'm going to the Halloween parade. And I might not be here on Friday, but I'll be here when I need to be here. So pay me. Right. I learned that, right? So I would just say out there to women, it can come. And if you are choosing to drive, which that's a choice. then don't parent from guilt.

Yeah, that's really important parenting advice. You know, I'm so interested in your parenting advice because between the two of you, there are six children and, you know, I think so much about resilience and independence and what we want for our kids. What are those parenting principles that, again, looking back, that you go, this was so important that I did this. Yeah. I will start with not parenting from guilt.

Because they feel it. Your kids feel that. If they feel you weak. Yeah, they do. You know, I always say kids have nothing to do but watch us. Yes, it's really, really, really true. They don't have jobs. They don't have responsibility.

They're watching. They're figuring. And it's like, ooh, she breaks down when I do that. Yeah, yeah, yeah. And, ooh, they play. Ooh, they don't work together on that issue. Let me manipulate that, right? Yeah.

I always say, don't let your kids outlast you. They're just kids. Mm-hmm. So you can, if they have questions, answer them until they have no more questions. Our parents were really good at that. And you don't have to give them sort of the college essay, but give them answers and keep them asking questions and just outlast them. And outlast them emotionally, too. Don't let your kid tantrum you into captivity.

You know, I mean, you got to, you know, if you're going to be a busy parent, then you got to have some backbone. You can't, you can't parent out of guilt. You can't give up on the foundation and the structure they need because you're not providing it every day. But that means you have to be more clear about it. You know, even with the girls in the White House, I mean, I could have felt so bad for them. I mean, they had secret service that they didn't. You know, they had to, they spent their childhood surrounded by men with guns. They were always out there in, in the wild, on their own.

taken on incoming as little girls. But I couldn't. I was thinking about who I needed them to be when this was over. And it couldn't be some bratty kids who didn't know how to hear no. They lived in a house with a florist and maids and cooks and chefs. Yeah. It's like not normal. They could have, you know, they lived in a museum.

You know, so I had to be like, who do I want them to be when this is over? But that is great advice. Like thinking about who do you want your kids to be? be and not like parenting in the moment because I feel like there is so much guilt and there's so much immediacy to how we make decisions now that sometimes you're like how do I just make this thing better now as opposed to being like well and then we give up how do I how do I appease them now so that they stop yelling right and the thing I've always thought about is how do I make them empathetic people who understand boundaries and have a work ethic which means that I had to create

knows. You know, the girls would tell me sometimes mom would just say no because. And I would because it's like there are no real noes when you live in the White House, right? So sometimes no would just know just because you need to know how to sit and know. Because most of life is going to be no. So you're going to practice it. Can you do that? No. Why? They're doing it. Because you need to know what no is. Now go sit in your room and think about why do you have to have it, right? What is your why? Why can't you hear no? And that hurts us, you know, punishments, you know? I feel like you're so, you don't shy away from difficult conversations. Like, are you like that everywhere in your life? Because I think it's so important. I think every friend of

mine would say, hell yeah. And sometimes it's exhausting. Do you say that? Hell yeah. That's the brother. Hell yeah. Having difficult conversations, saying, no, not people pleasing. How have you trained yourself to be like that? I mean, it's very clear that that's just who you are. Yeah, I, maybe you can, I just think it's... I think it's the way she was raised. My mom raised her to be tough.

And my mom helped... So how do we make women tougher? Like, how do we make ourselves more resilient? I don't know how to make them tougher because I think they're tough already. But my mom... You're in that family. That's right. But you know what I mean, right?

You know, like, some people don't, they don't find it so easy to tell their kids, no. They don't find it so easy to say, no, I don't want to do that. That's not going to, I won't find enjoyment in that. You seem to have a very, like, you're at ease with saying, no, I don't want this. This isn't right to me. Well, it was practice. It's a muscle that you build over time. And I think part of it was like, when you are raised as a poor black.

kid from a working class community, people will set their bar low for you. They will just assume that you can or you don't. And I think there was a part of me that grew up as a fighter. Every time someone assumed, based on nothing that I demonstrated, that I shouldn't have this or couldn't do that. So as I say, I have a I'll show you attitude, maybe because I'm the youngest sister. I was never treated like that in my household. My brother was always a year coming. My father was you put on these boxing gloves. I think so in my home, I was a can doer. But then when you get out in life and the first people you meet are like,

I don't think you can read. It's like, why would you assume that I can't read, you know? What? So that would make me angry, actually. And for some kids, that would make them feel defeated. So I think some of it is temperament. Some of it is that I had this really strong foundation of love, not just from my mother, but my father.

And so I came back to a home that said, of course you can. Those people are crazy. Not everybody, not every girl has that. Not every young girl, as we see through our work at the Obama Presidential Center, there are millions of girls all over the world who are being told for no good reason that you can't and you're not and you'll never, but they're still like me and like you, because you knew in your head, Emma, when you were four or five or five, seven, what you were completely capable of. Oh, I know. And every girl knows that. And it's the

world that turns us into mush. It's the world that makes us doubt ourselves. It's our societies that oppress us and make us feel anxious and small, right? And if you don't have a place that's lifting you up like I did, then you could just become smaller and smaller and smaller. And doubt yourself and your voice gets minuscule and you're afraid of your own kids. Societally, we are in a position as women where that can be the norm unless there's something that breaks you out of that. Yes. And I think my something was this amazing foundation of,

yes, you can in my household and a temperament that went along with it. So I think I am inherently a fighter for myself, and therefore a fighter for other people. So when I'm talking to my friends or, you know, any women, I'm like, hey, come on. We can, why? Why can't, why are you, what is it? Why are you crying? What is this about?

Let's get it together. Let's get it together. You know, and with my girls, it's like, no, you can't have it. It's okay. You don't need to whine. You'll be okay. And I love you. It's like, I can say no to my girls because guess what?

I really love you. always here. Yes. And I know that. So I don't owe you anything. I am here for you. I love you. You know it. You're friends, you know, so I can't, you can get some bad news from your mom. You can get the bad news. You'll be fine. You'll be fine. What is the, what is the advice that you would wish that more young people had right now? Hmm. That they have everything it takes. The advice for kids is like, If you have a voice in your head that says that there's something special in you, believe it. Believe that voice before it gets taken away from you. You know, believe the truth of who you were brought into this world as.

Because we all have that little voice. When we're very young, it starts early. And you just want to tell kids it's the other. stuff that's wrong. Yes. The thing in you that is telling you, you know better, you can do better, you deserve better, believe that voice over everything else. And go to the light, find the voice that's telling you differently, you know,

wherever it's coming from. If you're not getting it at home, go find it at school, go find it in the coach, find it in the gym, go to church, seek the light, you know, don't let that, darkness drown you out. That is fabulous advice. I've been thinking about it so much because we come from very different but very similar places. And when you're from humble beginnings and you do a journey, you have a successful journey, there's an inevitability of having to leave something behind or some people behind. And it can be really, really heavy. And so I wonder if you've, how you guys have navigated, because you're both so incredibly successful, how have you

navigated leaving people behind on the way or leaving where you're from behind? That's a good one. I would hope that we haven't left people behind, but I think the folks we've left behind are the folks we needed to leave behind. And we've kept the people who we want to us and who mean a lot to us, we've kept them around. And I think about, I think about Mish and Barack, every Thanksgiving, they invited our whole family to the White House for Thanksgiving. And so you only got left behind if you were supposed to be left behind. And there were some instances. There were always all. I mean, there always are. But I have this conversation a lot with minority kids going to college in particular, because that can be not understanding the need to leave

behind the people who need to be left behind gets a lot of young people in trouble. Not in trouble in, you know, legal ways. It's just, you know, we have kids who go to college and they take their student loan money and they're trying to pay their, the light bill at home, you know. they're grappling with survivors' remorse. And the thing that I remind them is that, you know, you got to put your oxygen mask on first. And it's a long climb to get to a place where you can really, really help others.

And if you stop too soon and try to help too early, you'll all fall, you know. And that's not leaving people behind. That's just being real about when you are really capable of helping anyone at all. And I tell folks, we were blessed, at least in our family. We didn't have people. My mother wouldn't accept stuff from us, you know. I mean, it wasn't until after we got out of the White House that we were in a position to buy my mom a safe place to live with a doorman, and, you know, which she didn't understand. She needed, you know, you're the former first

grandmother, you can't just live in the hood, you know. But I say that to young people to say, that's how long it took before we really could afford to bring others along financially. Oh, yeah. Right. So it's just, I remind young people, you know, who don't come from a lot, that you probably can't afford to help everybody. Your real answer is probably I can't help you yet. because I don't have two feet on the ground. And when you don't come from a lot, a little bit looks like a lot. But it's still a little bit. So I just, you know, I try to remind young people,

don't rush to be the savior until you're really, really solid. And that could take much longer than you think. And then when you really get to a place where you're rock solid and you're taking care of your own business, your own debt, and you have some leftover help then. But you can help with your time and other ways. There are other ways other than financial help and support, mentoring, being there now for cousins.

You know, we've set up scholarship funds for cousins and friends' kids and so on and so forth. But I'm 60. I couldn't have done it at your age. I couldn't have done it in my 30s when something. people when I was a corporate lawyer and people would have started counting my thinking, oh, future checks. And it's like, no, I got lots of debt that I got to pay off before I can help you with your mortgage, right?

And that's, you know, learning how to say no, too. And no being a real no. And no being a real no. It's a lesson. Michelle, do you still believe when they go low, we go high? Yes. Yes. I have to.

Do you still believe it with the same conviction? Yes. Yes. Emma. Okay, good. Fine, because, you know, we're trying out here. We're trying. Because guess what?

Going high is a long-term strategy, and it's the better way to show up in the world. Because when you don't, when you lead with fear and bitterness and exclusion, no one wins, you know? No one feels. like they're winning right now, truly, you know. Amen. So yeah, I still believe, you know, and it is a strategy. It doesn't mean you don't emotionally feel low at times. It doesn't mean, you can feel low. You can feel it. But we're just going to go. But when you show up in the world,

show up high. That's, I still believe that. We shall continue. Okay, I'm going to take you to rapid fire. All righty. What is the first thing you do when you wake up in the morning? I sadly check my phone. No, you do not. I have kids. Like straight away? I do. I do.

Because over the night, it's like, did somebody need something? Is everybody alive? Right. So I do check my phone. Greg, what do you do? I play a variation of games because I'm on two text chains with people. I do wordle, connections, strands. and spelling B.

And I also do four picks and one word. You are keeping that brain fired out here. Trying to keep my little pea brain fired up. Is it the same before you go to bed? What's the last thing you do? No, no. Oh, the last thing I do before I go to bed is brush my teeth. He's so specific.

Oh, I love the specificity. That's this rapid fire. What do you want? Michelle's going to say something more than that's top. She can't do rapid fire. This is going to be tortoise fire. I am Michelle in a rapid fire. Guess what I do?

I kiss my husband. Good night. Oh. Oh, that's nice. That's nice. I love that. So nice. What are you currently both aspiring for in your business life?

Ooh. I'm aspiring that the initiatives that are business initiatives are successful and add value in a meaningful way. So, you know, we've started Plessy nutrition and we want the drinks to be profitable, but we want them to deliver in terms of good quality, lower sugar. That's your initiative with them. That's your business with Steph Carrey, right? Yeah, yeah. We have our new hydration drink out and it's, you know, providing quality without the sugar because that's the point. Like, we can do both.

We can do well and we can do good. I am very into that for you. Yeah. Do you care about money when it's those type of things? Sorry, I'm bad at rapid fire. Yeah, see, see? Sorry, Greg, I'm about at rapid fire. I still want to be, I'm internally competitive.

I want the things I do to be successful. I think Barack is the same way, Steph and Iesha are the same way. We do it. We want to do it well. We want it to be successful. And successful in a business setting is market share, right? Yes, it is. That's, yeah.

It matters. It does. It matters. I'll team up with that one and say, to use one of your words, impactful. I want to be impactful. At this age, this stage of the game, you want to be impactful. And I want to make sure I'm developing the bench, the younger crew who's coming along. I want to leave some folks around who can take care of this place.

And what are you aspiring for in your personal life? Rapid, rapid, rapid. Good health. good health and to get these last two boys raised as well as we did the first two

and that can be on their own that's a big aspiration I think my wife Kelly and I would agree on that one yeah personal for me it's I am grasping for

deeper mental and physical health taking care of this vessel that I have. That's a great aspiration. That really is. What is a book that changed your life? Oh, I know this one. Firestarter by Stephen King. And the reason is I had gotten through elementary school, high school, and college without being a real reader. I read to pass tests. And that book turned me into an actual reader. Wow.

And it happened in Stockport, England, Manchester, England. Because the four channels that you had went off at 11 o'clock. So I had to do something. And my family bought me a bunch of books. And they bought me one of them with Stephen King's Firestarter. That was that. I was hooked. I mean, good habit to get hooked on.

Yes. Right? And it's one of the, it's never too late to become a real reader. Yeah. I mean, I'm a lifelong reader. I'm extremely dyslexic. But for whatever reason, I could read big books from a very young age and always did. Michelle, for you, book that changed your life?

Song of Solomon by Tony Morrison. I read it every couple of years. And, you know, she's one of my favorite authors. and that book is deep and complex, and the characters stay with you. What is something that you valued when you were starting out your career that you don't now? Pleasing others, I would say.

Not letting money drive my decisions. That's a great one. That is a great one. All right, final question for both of you. What is something that you value now that you didn't? back then? Hmm. Freedom to do whatever I want. I mean, I guess because I didn't have that freedom.

So now I have the true, true freedom. Now that my kids are raised and you're not there yet, and my big work is done, right? I feel like I've earned the right to do what I want. And now I have to figure out what that is completely, right? Yeah. I, on the other hand, was able to figure out what I wanted to do early and got a chance to do it. So I value now my free time.

I didn't value it before. But I do now. Spoke a knock a tree, father of four. Yeah, really. You and me both. With two still, one still in middle school. Like, who, good luck. Good luck too, yeah.

It's fun on this side. I could be like, mom. It's good on this side. We're all waiting. Thank you both. You are amazing. Oh, thank you. This was great.

If you're loving this podcast, be sure to click follow on your favorite listening platform. While you're there, give us a review and a five-star rating and share an episode you loved with a friend who would be so grateful. Aspire with Em Agreed is presented by an order. I'm your host, Emma Greed. Our executive producers are Corrine Gilliard Fisher, Derek Brown, and me. Our executive producers from Odyssey are Maddie Sprung Kaiser, Leah Reese Dennis, Asha Saluja, and Jenna Weiss Berman.

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