Tell Your Story with Jonathan Capehart

Summary

Podcast Summary: IMO with Michelle Obama and Craig Robinson

Episode: Tell Your Story with Jonathan Capehart
Guest: Jonathan Capehart
Original Release: January 7, 2026
Host: Higher Ground

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Overview

This episode features a candid, warm, and insightful conversation with Pulitzer Prize-winning journalist and author Jonathan Capehart. Michelle Obama (Sa), her brother Craig Robinson, and producer Natalie sit down with Jonathan to discuss his bestselling memoir Yet Here I Am, his formative years in the segregated South, the influence of his mother, navigating identity as a Black gay man, and the meaning of chosen family. The episode also addresses a heartfelt listener question about familial acceptance and boundaries, with Jonathan offering practical wisdom rooted in his personal journey.

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Key Discussion Points & Insights

1. Memories of the Segregated South and Family Heritage

[00:00–16:47]

• Summers in North Carolina:
  Jonathan recalls his childhood trips to Severn, NC, living with his devout Jehovah’s Witness grandmother, Sister Isla Mae. These summers were crucial in shaping his view of race, heritage, and self.
  • “Going witnessing with my grandmother was this woman ... such a devout Jehovah's Witness ... we'd go witnessing on these country roads.” (Jonathan, 06:47)
  • Vivid descriptions of rural customs, witnessing, and the fashion sense passed down from his grandmother and Aunt Annie.
• Racial Segregation and Small Acts of Protest:
  Jonathan’s mother, Margaret, always drove down “White Street” in their Mercedes—described as “a slow motion protest at 15 miles an hour.”
  • “The black daughter of Severn is back in town. ... I'm home. I'm here with my northern address and my education, and I'm bringing my kid.” (Jonathan, 14:31)
• Miss Betsy Story:
  A touching account of his grandmother’s friendship with Miss Betsy, a white woman secretly practicing as a Jehovah’s Witness due to her racist husband.
  • “Miss Betsy would dive into the backseat and get on the floor ... and then she would get up, and we'd be laughing ... it was so sweet.” (Jonathan, 12:08–12:36)

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2. The Unbreakable Bond with His Mother

[19:25–30:14]

• Margaret’s Resilience:
  Jonathan’s father died when he was four months old. His mother worked double shifts, teaching him self-reliance and the importance of education.
  • “She taught me how to iron, how to do laundry ... you have to be able to depend on yourself. And there’s some upsides to that. There are also some downsides.” (Jonathan, 21:40)
• Navigating Race in Predominantly White Spaces:
  Margaret deliberately moved to safer neighborhoods and prioritized Jonathan’s academic readiness.
  • “She would say, ... 'if anyone calls you the N-word, you let me know right away,' and ... 'don’t let them put you in vocational education.'” (Jonathan, 23:54)
• Hard Conversations About Race:
  Margaret offered frank guidance about the inevitable inequalities Jonathan would face.
  • “You and Skip, right now, you’re equals... But as you get older ... Skip is going to climb higher. And he’s gonna climb higher because he’s white.” (Jonathan, 27:30)

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3. Coming Out and Embracing Identity

[30:14–36:47]

• College as a Place of Liberation:
  Carleton College provided a nurturing environment where Jonathan could come out and accept his identity.
  • “Coming out at Carleton was easy. I mean, relatively easy.” (Jonathan, 31:16)
  • Matthew Brooks, a peer, moved the gay group from the basement to the student union, symbolically encouraging openness and pride.
• Coming Out to Family:
  Jonathan recounts his carefully orchestrated conversation with his mother after college—her surprise, concern for his career, but ultimately, ongoing love.
  • “Are you gay?”—“Yes.”
    “First she goes, 'Why?' and I said, 'I don’t know.' ... 'It’s not your fault. It’s just me.' ... Next thing she said was, 'Don’t tell anybody. You don’t wanna ruin your career.'” (Jonathan & Natalie, 35:42)

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4. The Power of Chosen Family

[41:01–61:37]

• Stepparents and Uncles as Role Models:
  Jonathan’s stepfather was a negative influence, but his Uncle McKinley provided a loving, affirming example of manhood.
  • “From him I learned what it meant to be ... a good dad, a good person, a good man.” (Jonathan, 41:39)
• Navigating Familial Rejection:
  Describes being rejected by his grandmother for wanting to bring a partner home but later discovering it was due to external pressure and experiencing reconciliation thanks to loving relatives.
  • “You are always part of the family ... And Giuseppe.” (Jonathan, 43:19)
• “Shoulders Down” Spaces:
  Importance of finding community (“chosen family”)—from 1990s NYC Black professionals to Martha’s Vineyard—as sanctuaries of affirmation.
  • “When you realize ... you walk into this room and I’m surrounded by people ... and we all have this common cultural ancestry ... that’s why Martha’s Vineyard is such a special place. That is a place where shoulders come down.” (Jonathan, 61:00–61:37)

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5. Listener Question: Family Acceptance and Boundaries

[46:47–54:41]

• Dominic’s Dilemma:
  A listener named Dominic, the only openly gay man in his family, struggles with his brothers avoiding gay spaces and feeling unseen.
• Jonathan’s Advice:
  • Assert boundaries within family just as you would with anyone.
  • Find and cherish your chosen family if your biological family cannot fully accept you.
  • “Sometimes I think family uses the family tie to keep you ... in place. ... At a certain point, you are going to have to stand up for yourself, family or no family.” (Jonathan, 49:05–49:22)
  • “When you know who you are, when you are just firm in your belief ... then everything else should flow from that.” (Jonathan, 51:41)
  • Recognize that setting boundaries may require sacrifice and can sometimes limit opportunities or relationships but will ultimately increase wellbeing.

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Notable Quotes & Memorable Moments

• On showing up in the South:
  “It was a slow motion protest at 15 miles an hour. ... I don’t have to honk my horn, let the car do the talking. And I’m home.” (Jonathan, 14:31)
• On childhood resilience:
  “I was always going to college. It was just a matter of getting in and where would I go.” (Jonathan, 29:55)
• On coming out:
  “‘Are you gay?’ ... I said, ‘Yes.’ [My mother:] ‘Why?’ ... ‘I don’t know. ... It’s not your fault.’” (Jonathan, 35:15)
• On chosen family:
  “Shoulders come down ... that is my New York. This family was formed in the mid-90s ... and we have these common aspirations.” (Jonathan, 61:17)
• On boundaries and self-worth:
  “Just because they’re family, that does not give them a pass to not treat you with respect or the way you want to be treated.” (Jonathan, 52:41)

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Important Timestamps

• Segregated South & Main/White Street:
  [00:00–15:37]
• Childhood, Family, and Educational Upbringing:
  [19:25–30:14]
• Coming out, Self-Acceptance, and Mother’s Reaction:
  [30:14–36:47]
• Listener Question and Guidance on Family Boundaries:
  [46:47–54:41]
• Chosen Family, Cultural Community, and Martha’s Vineyard:
  [59:09–61:37]

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Tone & Atmosphere

The conversation is intimate, conversational, and full of laughter and shared reminiscences, grounded in warmth and respect. Jonathan’s openness sets the tone for heartfelt advice and camaraderie, making this episode both moving and practical for listeners navigating identity, family, and self-acceptance.

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For More:
Jonathan Capehart’s memoir Yet Here I Am is available now wherever books are sold.

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Transcript

[Jonathan Capehart]

The formal name was Main Street. The colloquial name was White Street. And so my mother would make that right. And I never understood why. I was like, mom, you just go down there and go. But you know, driving down south in your brown 450SL Mercedes, which I was like, stop there.

[Sa]

Stop.

[Natalie]

Stop there. Mom. K part with your bins.

[Jonathan Capehart]

I know, with her bins.

[Dominic]

She was like.

[Natalie]

And we going down White street in our bins.

[Jonathan Capehart]

In our bins. And as I write in the book, it was like. It was a slow motion protest at 15 miles an hour.

[Natalie]

This episode is brought to you by theraflu. How are you?

[Sa]

I am really well. I got a good night's sleep last night and I have the beds at the Airbnb to thank for it too, because.

[Natalie]

Oh, that's right. Yeah, you've got. So the beds are comfy. Comfy where you're staying.

[Sa]

And you know, not everybody has the same Matt. But this one is on a platform. So it's not like a box spring and a mattress. This is just the mattress on a platform. But it feels like I'm on a regular bed.

[Natalie]

Oh, well, there you go. Yeah, that's a good tip off.

[Sa]

Enough about my night.

[Natalie]

Uh huh. Yeah.

[Sa]

We have a guest here.

[Natalie]

We do. But one of the things we said we wanted to do today because we want to officially welcome back Natalie, our producer who has been on maternity leave and she is a new mommy of a beautiful baby girl. Remind me of your daughter's name, Leona. And she's back. Welcome back. And you know, we also have to.

[Sa]

And we also want to say thank you to Julia, who substituted in your stead and did an excellent job. So Julia, thank you so much.

[Natalie]

Welcome back. And now to Natalie and thank you to Julia.

[Sa]

We got em both one.

[Natalie]

I know. Do we get both of you now? All the time.

[Sa]

Okay, so we have a friend of yours and I met him many years ago during the first administration in the White House. But I told him it was so many people I met and I probably, I was still coaching, so I probably had lost the game and didn't want to.

[Natalie]

I don't know how you can not Jonathan Capehart. I mean, Jonathan Capehart is like, he's a fixture in so many homes.

[Sa]

Yeah, I know of him, of course.

[Natalie]

But you didn't remember what he met.

[Sa]

I remembered meeting him. And you know, Jonathan is a Pulitzer Prize winning journalist. He's also the co host of the morning edition of the Weeknd. He's an analyst on the PBS NewsHour.

[Natalie]

This man's got a lot of jobs.

[Sa]

I know.

[Jonathan Capehart]

I know.

[Sa]

Capehart was previously associate editor at the Washington Post, where he was also an opinion writer. His memoir, Yet Here I Am, was published earlier this year and was an instant New York Times bestseller.

[Natalie]

Yes, it was.

[Sa]

It is a really nice read.

[Natalie]

It's a beautiful book.

[Sa]

It's a beautiful book, and I'm looking forward to talking to him about it.

[Natalie]

So without further ado, Jonathan K. Park, here he is.

[Jonathan Capehart]

Thank you for having me.

[Sa]

Thanks for being here, man.

[Jonathan Capehart]

Great to see you. Nice to see you again.

[Natalie]

Jonathan. Jonathan, welcome to imo.

[Jonathan Capehart]

Thank you very much.

[Natalie]

We did this. We concocted this visit because of your bestselling book. We talked about it a bit. I was like, why don't we talk about it on imo?

[Sa]

Yeah.

[Jonathan Capehart]

And I was thrilled. Thrilled that you wanted to have me on and talk about the book. And I'm looking forward to these de. Do you understand how weird this is? I'm the journalist. Yeah. I. I can imagine the questions and try to find ways to get you to not get off your talking points. And now I'm getting it from you guys. We're gonna be real funny. I don't know. Do you say that now?

[Natalie]

But this is what I love about the book. It's a beautiful book. It's. You know, it. It's a wonderful journey through your life, but I love it because it's. In telling your story. We get to see all of Jonathan Capehart. It gives us a real connection to you as a human being, as a man. Your journey is beautiful, and it's beautifully told in this book. So congratulations.

[Jonathan Capehart]

Thank you. Thank you very much.

[Sa]

And it's a nice read. It really is. And I didn't become a reader until I was an adult. I knew how to read, but I didn't have to.

[Natalie]

Well, I know the way you say that. I was like, whoa.

[Sa]

I read for school, and I've told the story many times that the first book that got me to be a reader was Firestarter by Stephen King. And so I try to. I have this pattern of I have to read two nonfiction books in order to get to read one fiction book. And yours, of course, is a nonfiction book. And it was a nice. So thanks for doing it, man.

[Jonathan Capehart]

Sure.

[Sa]

I feel like now I feel like. I know.

[Jonathan Capehart]

I mean, if you don't know me, if I read that book, I don't know what book you read.

[Sa]

Tell us about the process of it and how it sounds like it was wonderful, but I want to hear from you so what was it like writing it?

[Jonathan Capehart]

So during the first Trump administration, I decided to. You know what? This is a little intense. I'm going to get off this merry go round. And all these stories that I had in my head from my summers as a kid, spending them in North Carolina with my maternal grandparents, I'm finally gonna get them out of my head and onto the screen. And I spent an entire weekend just writing what I started calling the down south chapter.

[Sa]

Wow.

[Jonathan Capehart]

Writing about how the prominent thing is, I went to Catholic school in the north and then would go down south to North Carolina and spend the summers with my Jehovah's Witness grandmother.

[Natalie]

That was. That. That stood out. Cause I don't think I knew of your connection to Jehovah's Witness. Grand. And I didn't realize that your grandmother was such a devout Witness. Are they called Witnesses?

[Sa]

Yeah.

[Natalie]

Yeah. So you had started. You've been going down south since.

[Jonathan Capehart]

Yeah, since I can't even remember the first time I went down. But, you know, I went basically every summer until I was 12.

[Natalie]

Yeah.

[Jonathan Capehart]

And so going down south, being in the heat, the humidity, the mosquitoes, the thunderstorms, the rain hitting the tin roof, all of that just. I mean, those memories, the smells of the summer never left me. And especially going witnessing with my grandmother was this woman. She only had a fourth grade education. She knew how to read, she knew how to write, and she was such a devout Jehovah's Witness that we would go witnessing on these country roads in North Carolina.

[Natalie]

That's a trip if I'm just picturing this old lady and this well dressed little man in the back. Talk about what, you know, help us. Paint that picture for us.

[Jonathan Capehart]

Grandma or Sister Isla Mae?

[Natalie]

Sister Isla May.

[Jonathan Capehart]

Sister Alame and I made for quite a pair. Now we'll put aside my fashions for a moment. My grandmother, she liked to dress and she would get a simplicity. She would look through that. Wasn't there a book or something?

[Natalie]

You saw Simplicity, Buttermilk. There were tons of catalog. Catalogs, patterns and.

[Jonathan Capehart]

Right. So she would flip through and then she would see a pattern. And then we'd go into town, Muffersboro, and go find the pattern and bring it back home. And Grandma would make her dresses right there on the kitchen table. I could still hear the scissors crunching on the metal tabletop. And then she would sew them. She'd get behind her little Singer sewing machine, and then on Sunday, you couldn't tell her nothing. She'd slip that sack dress on over her head, put her Faux pearls on. Cocked that wig on just right and put her, you know, purse in the crook of her arm, Queen Elizabeth style.

[Natalie]

Yes.

[Jonathan Capehart]

And you couldn't tell. Sister Isla made kindred. Not a thing. And so then there's me, you know, so my family calls me Todd. Everybody in my family calls me Todd. So there I am, little Todd or Todd Todd. And I see myself in, like, khaki pants, of course. A little shirt, button down. Little button down.

[Natalie]

Blue, white.

[Jonathan Capehart]

I don't remember. I mean, I do remember, like a khaki pants and a red. Like a red polo of some sort. I like to look good because my grandmother, but also my Aunt Annie, my Aunt Annie Branch, she was like, I like it when you dress up. You look nice. And so it was all about looking good for Aunt Annie, looking good for Grandma, and of course, you're going to Kingdom hall on Sunday. You gotta look your Sunday best. So it's stuck.

[Natalie]

So you're pulling up to somebody's house. I'm sorry.

[Sa]

No, I'm just gonna say we didn't go down south as often as you did. You went every summer? We went like a couple of times, three times maybe, in our childhood.

[Natalie]

Yeah. So you all. You and Grandma all dressed up. You go go down a country road to witness, and you're going to all kinds of folks. White folks, black folks. Oh, I wasn't sure, because one of her friends.

[Jonathan Capehart]

Ah, yes, Miss Betsy.

[Natalie]

Miss Betsy. Tell us about Miss Betsy, because that story was very sweet to me.

[Jonathan Capehart]

So I don't remember how Grandma met Miss Betsy, but Miss Betsy was a true character. True, true character. Jehovah's Witness. But her husband didn't know. Her best friend was my grandmother. Her husband, according to Miss Betsy, was just this out and out racist. So could never know that. One, she was a Jehovah's Witness, and two, she was cavorting with black people. And so whenever we would have to go, not to Kingdom hall on Sunday during the daylight, she could make her way. But if they went witnessing or at, you know, in the evening or Bible study, Miss Betsy would call and the phone would ring and we would go. I'd go get the phone. Hello. And then there would be silence on the other end. And that was like, oh, this is Miss Betsy.

[Natalie]

Okay, it's time to move.

[Jonathan Capehart]

Right? So I would wait to listen, and then she would whisper into the phone like, I'm on country Road Route 4, by the Big tree across from the house on the bend. I'll be in the. Hiding in the ditch. You just, You Honk your horn when you get there. Like, okay, hang up the phone. I'd run in, okay, I know where Miss Betsy is. I tell Grandma. And Grandma driving rail.

[Natalie]

Hour later, I'm just picturing Miss Betsy in the ditch, wondering, where is she?

[Jonathan Capehart]

No, she knew.

[Sa]

She knew.

[Jonathan Capehart]

So we pull up in this one instance that comes to mind. And, you know, it's pitch black, the brights are on, and Grandma beeps the horn, and we just sit and we wait. Because, you know, what if we were followed? What if her husband's following us? And then out of nowhere, Miss Betsy would pop up out of the darkness, and she's this white woman in her own sack dress, purse crook in the crook of her arm, Bible in the other hand.

[Natalie]

Just the white version, right?

[Jonathan Capehart]

The white version of Grandma. And she would come running, you know, old lady waddy, running to the back. Miss Betsy would dive into the backseat and get on the floor. And then we would drive away in case her husband was following us, which he never did. And then she would get up and we'd be laughing, and she was just wet. She was always just.

[Natalie]

Well, after laying in the ditch and then running in a sack dress. I mean, I'm like, I bet. I bet she was sweating, humidity.

[Jonathan Capehart]

Like, she would kiss us, you know, give us hugs and kisses, cheeks all wet. I hate that to this day. But it was so sweet. It was really, really sweet.

[Natalie]

I mean, it's a sweet story. Moving, touching on so many levels. But it spoke to the challenges of a deeply still segregated South. And you witnessed, you grew up in that. I mean, like Craig said, our experiences in the south were intermittent. But you going down there every summer, every summer and living it and talk about what it felt like to be a black boy in the segregated South.

[Jonathan Capehart]

I mean, I didn't know what it felt like until, you know, decades later and particularly when writing this book, understanding. Well, wait. Well, what were those summers like? Oh, Severn, North Carolina, is a Jim Crow relic of a Southern town. You know, my mother, I write about how my mother, when driving down south, when you're coming down the road, the first right will take you down Main Street. The second right further down will take you down the street where she was born and raised. My mom always took that first right down Main Street. Main Street, Wide paved boulevard, double yellow line. The street was lined with these big houses, and the formal name was Main Street. The colloquial name was White Street. And so my mother would make that right. And I never understood why. I was like, mom, you just go down There and go. But, you know, driving down south in your brown 450SL Mercedes, which I was like, stop there. Stop.

[Natalie]

Stop there. Mama Capehart with your bins.

[Jonathan Capehart]

I know, with her bins.

[Dominic]

She was like.

[Natalie]

And we going down white street in our bins.

[Jonathan Capehart]

In our bins. And as I write in the book, it was like her. It was a slow motion protest at 15 miles an hour. You know, the black daughter of Severn is back in town. She's announcing, I'm here. I don't have to honk my horn, Let the car do the talking. And I'm home. I'm here with my northern address and my education, and I'm bringing my kid. Yeah. And so. But then you get around the bend. In those early years in Severn, that street wasn't paved. It was a dirt road and it had no name. And one summer we came back and it was paved, but it was paved in sort of like tar and those pebble rocks. So when the sun was beating down on the summer, it would bubble up in tar. So my feet would be covered in tar. Cause I'm running around. I'm a kid in the summer, running around in the street and on the grass and everything. Again, no formal name until they named it south street, but it's still known to this day. Colored street.

[Natalie]

Yeah.

[Sa]

Wow.

[Jonathan Capehart]

We were the first generation in our family that didn't have to pick cotton. And we were sort of the first generation of sort of quote unquote, post civil rights movement kids. I was born exactly three years to the day after the enactment of the 64 Civil Rights act, less than two years after the passage of the 65 Voting Rights Act. So at, you know, five, six, seven years old, I'm the first child. We're the first children in our family to live in de jure freedom in the United States. And I'm doing it there in this, you know, where segregation is still kind of. Still kind of around us. It is among the many memories in writing the book where I realized just how much those summers shaped my worldview, my view of this country, my view of myself. Ms. Betsy.

[Sa]

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[Natalie]

Your mom. I want to talk about your mom too because just a lot of things you said in describing your time down south. Number one Southern girl comes back after with an education, a beautiful car, successful. But your mom was a single parent and she did all that on her own. And I just want you to talk a bit about Margaret who by the way I would want to have here because Margaret is actually my favorite Capehart.

[Jonathan Capehart]

You know she is gonna dine out on that forever.

[Natalie]

Well tell us about your mom's story, her journey and you know how she pushed through and was she like as a mother to you, all of that good stuff.

[Jonathan Capehart]

So a few things, foundational facts.

[Natalie]

Yes, I know you know how to.

[Jonathan Capehart]

Do my mother and father Married two years before I was born.

[Sa]

Right.

[Jonathan Capehart]

They moved to Brooklyn to Park Slope, and then moved to Newark. My father died when I was four months old. He had a blood clot that went from his legs to his lungs to his heart. I found out from my godfather years later that the doctors told him he needed to have his legs amputated. And so my father apparently said to them, well, I like to dance, so you are not taking my legs. I was born with two legs. I'm gonna die with two legs. And my godfather told me that from that moment, he decided to live life the way he wanted to live it. And unfortunately, that meant he left his pregnant wife before I was born. And so when he passed away in 1967, no one called my mother to tell her that he had passed away. Oh, I left out a key point. When he left, he moved in with the girl.

[Natalie]

With another woman. Yeah.

[Jonathan Capehart]

No one called her to tell her that he had passed away. She would call daily the hospital to check in on him. Cause my mother is a nurse. She's now retired. A nurse. And they said he passed away. And then she told me a guardian angel called, came to the apartment in Newark and said, you need to get over to Capehart's place now and get his legal papers. Go and get all of them. My mother said, you know, he always traveled around with an entourage. And so she goes over to the house with police officers. And she said, you walked in and there were just people sitting around. Any of these jokers are gonna, like, call his wife. Cause he didn't divorce her. She got the legal papers. And then another person, another guardian angel, as she described them, told her that, you know, you're entitled to veterans benefits for the rest of your life. And it's those two guardian angels who change the trajectory of our lives. I would also say that, you know, Willie Capehart changed the trajectory of our lives by not divorcing my mother. Because as a result, we were able to avail ourselves of those things. So my mom, she worked her butt off double shifts. She taught me how to iron, how to do laundry, how to. Okay, mom even knows this. She's not a great cook, but she did teach me how to boil water to make pasta. She taught me things. So that way, as she said, you don't want to have to rely on anybody else. You have to be able to depend on yourself. And there's some upsides to that. There are also some downsides to that. But she instilled in me and independence that she knew I would need. She Sheltered me as much as she could from the slings and arrows of life, particularly when it comes to matters of race. And we left Newark and moved predominantly white towns. And the first day of school, she would say, okay, two things. One, anybody calls you the N word, you let me know right away. And two, don't let them put you in vocational education. They're always trying to push us into voced. You are going to college and you should be in college. College prep courses. Yes, ma'. Am.

[Natalie]

And did she intentionally move into a neighborhood where she felt you would have. How did she think about education and, you know, and the fact that she lived in a predominantly white community? I think you said she made choices about where she was going to live to ensure that you got.

[Jonathan Capehart]

Oh, sure. It wasn't as like today, folks like, hey, what is the elementary school? What are their scores and their placement within the state. No, mom was like, we gotta get outta Newark and we gotta go someplace where it's not Newark. So the first place was North Plainfield. Lovely. Not ideal. We only lasted two years, and then we went further south to Monmouth county, to this town called Hazlett, New Jersey. And we were only there for four years, but to me, that was an incredible lifetime. And, you know, another predominantly white school, white town where I just dove. I just dove in. I ran for student council, became student council vice president at Beer Street Elementary School, and then did the same at Raritan High School. Like, dove right on into it.

[Natalie]

And you felt accepted? Did you have issues of race, Teachers lowering your expectations? Did you have any of those kind of challenges?

[Jonathan Capehart]

When I got to Raritan High School, you know, I was looking forward to going to homeroom with my fellow nerds. And instead, my homeroom was the shop. Yeah, yeah. You know, sitting. Attract you sitting around this giant wedge table with the. What is that? That. What's that thing called?

[Natalie]

The vice.

[Jonathan Capehart]

The vice, yes, that vice thing. Smell the turpentine and wood and oil and metal and stuff.

[Natalie]

Jonathan's like, where am I? This isn't Kansas anymore.

[Jonathan Capehart]

What is? My khakis. They're gonna get dirty. How dare they?

[Sa]

But, Jonathan, I wanna go back because I think there are a lot of mothers who are like, Margaret, single mothers who are raising black kids. And somehow she gave you the confidence to walk into these spaces and be okay, fit in, not feel intimidated. How did she do that?

[Jonathan Capehart]

That is a great question. I mean, I think it's a combination of her parenting, but then also just sort of the way I was. I took it upon myself to Be like, hi, I'm here. Let's be friends. Also, you're an only child. You want to go make friends. So it was just perfect. My mother, I'll never forget again. Her admonition was, if anyone drops the N bomb, you let me know. Well, it happened one day in Hazlet, right outside our apartment. And it was a kid who was not part of our crew, but he dropped it. And I ran in screaming to my mother, it happened.

[Natalie]

He said it.

[Jonathan Capehart]

He said it. Mom. She comes running out halfway, wanting to.

[Sa]

See what would happen, right?

[Natalie]

It's like.

[Jonathan Capehart]

So mom comes out and she breaks it up and says, my little friend's home. And then she says, todd, come here. We have to talk. Sit down on the sofa. And Skip, my next door neighbor, was also my very best friend. And she says, now listen, you and Skip, right now, you're equals. You're right here. But as you get older and you move through life, Skip is going to climb higher. And he's gonna climb higher because he's white. I was screaming at the tops of my lungs, how can you say that? That's not true. You're lying. Why are you doing this? I really, like, she tore my heart out. This conversation. Tears. I screamed myself hoarse. And I remember just the look on my mother's face, in hindsight, was one of sorrow. Yeah, sorrow is the way I would put it. Because just think about it, she has had to have this. She knew this conversation was coming. She probably, knowing me, she knew what my reaction would be. And you can steel yourself against that and prepare yourself for that as much as you can. But when you see your child respond in that way, how could that not be heartbreaking, but also heartbreaking because you know at some point that same child is going to come back to you decades later and say, you were right. I was naive in a lot of ways. I still am that naive little boy. But it was that naivete that gave me the blinders to plow ahead, to walk into rooms where people would look and like, who's this black kid? Who does he think he is? And also, you know, back to my mother, my mother always made a point of ensuring that our education was front and center. We would go out to the mall, and she would say, don't even think about going into Toys R Us. KB Toys. Not going. Not buying you a damn thing. But we go into Barnes and Noble. Cause mom would always go into the bookstore. You all spend whatever you want on any books. She said, you are going to college. And if you are 18 and not in college. You are not living here, because I'm not taking care of a grown man. So I was always going to college. It was just a matter of getting in and where would I go?

[Sa]

So speaking of college, I want to delve into Carleton College because you write about knowing that you were gay since you were 10 years old, but you did not feel comfortable until you got to Carleton. Can you talk about that? Because I'm just fascinated by that, because I'm a Midwesterner, and I think people in the Midwest are nice. What was it about Carlton that made you feel comfortable enough to sort of be yourself?

[Jonathan Capehart]

Well, two reasons. One, Carlton is a very nurturing environment.

[Sa]

One.

[Jonathan Capehart]

But two, it boils down to a person. And his name is Matthew Brooks. And he was a year behind me in college. And we met my sophomore year, his freshman year, and it was in Goodhue Hall. And he was gay. He didn't tell you he was gay. You could just, look, he's gay. He didn't run away from it. And in fact, he took over. Took over. He, you know, became part of the leadership of the gay group on campus.

[Sa]

Okay.

[Jonathan Capehart]

Moved it from the basement of the chapel to the second floor of the student union. And just symbolically bringing it out of the shadows, putting it someplace where, you know, yeah, people might see you, but guess what? You're not hiding. This is not something to be ashamed of. And so, you know, coming out at Carlton was easy. I mean, relatively easy.

[Natalie]

And what was going on with you internally in this process? I mean, you know, you're. You're having this awakening at Carleton on so many different levels, but you're doing it away from home. And there was the Jonathan at Carleton, but then there was this whole Todd back.

[Jonathan Capehart]

Oh, back home, at home.

[Natalie]

And how did you feel as you were coming into your own? What did that do to you? Was it frightening? Did you worry about, you know, what this would mean?

[Jonathan Capehart]

I never feared that my mother would disown me, that my family would kick me out and do horrible things.

[Natalie]

Why did you know that for sure?

[Jonathan Capehart]

I just did. I just did. And also, I'm of the. Even then, I'm of the mind that you gonna kick me out of the family, because this is who I am. Okay, well, bye. Bye. Exactly.

[Natalie]

Bye.

[Jonathan Capehart]

So when I was at Carlton, sure, You know, you're dealing with these things. You're struggling, like, who am I? Is this me? What's going on? How will my friends react? And then. But there's a liberation there. But then you go home and now you're under the roof of your mom and me, at the time, my stepfather. But you get home, and now you have to go back into the closet.

[Sa]

Yeah.

[Jonathan Capehart]

And so finally when I came out to my mother, it was, you know, it was a relief.

[Natalie]

Was it a surprise to her? Was it sort of like I was just waiting for you to tell me.

[Jonathan Capehart]

It'S a yes and no. All moms know, you know, I maneuvered. I maneuvered the conversation so that she would ask me. Cause so many times I came up to the line of saying, mom, I'm gay, and chickened out. So I'm back from Carleton. I graduated and stayed a year to work as assistant to the president of the college back home in my childhood room in Hazlitt, which suddenly feels a whole lot smaller now, right? I'm sitting on the futon. And my mom, she's mad because I corrected her on some of her language about her about college boy, right? And she said, ever since you came back from college, you've become so. So liberal.

[Natalie]

It's like, ooh, slap me in the face, dare you.

[Jonathan Capehart]

And I said, well, what are you talking about? And so we go back and forth, and I said, you know, I just somehow made the way to, you know, gays and lesbians, they're always talking about, you know, wanting to be accepted and blah, blah, blah. Well, they're doctors and lawyers and journalists and all these things. You are part of the mainstream. Blah, blah, blah. And my mother standing in my door, she's like this, well, are you gay? And right then, I'm sitting on my futon, feel like this beam of light, like I'm in my own one man show. And it was the moment of truth. And I said, yes. The first thing she said. First she goes, why? And I said, I don't know.

[Natalie]

And then she says, why? Oh, that's sweet.

[Jonathan Capehart]

And then I said, it's not your fault. It's not your fault. It's just me. It's just who I am. And then the next thing she said to me was, don't tell anybody. Mm. You don't wanna ruin your career. And I looked at her and I said, too late. I'm not gonna go out and tell. You know, if someone asks me, I'm not gonna lie.

[Natalie]

Yeah, right.

[Jonathan Capehart]

You know, and also, besides, have you seen. I got a big. There's a gay bar in. I don't know if it's still there in Minneapolis called the gay 90s. And it has a big neon sign says gay 90s. And then it has like these rainbows that come down in neon lights like this. And I said, I've got this neon sign over my head. So I mean, if you got your eyes open, you know, you already know. So. But I'm not going to lie. And you know, this was a part of the tension between my mother and me. She's from the older generation where you don't talk about these things. You don't put yourself out there like that, you don't make risks. And I am from the new generation, the post civil rights generation. I'm still that kid. I'm free. And the world is changing. While it's not changing as much or as fast as I think it is, or that I hope that it is.

[Natalie]

So the truth is still somewhere in the middle.

[Jonathan Capehart]

Yep.

[Sa]

Foreign. You know, January always feels like that moment to hit reset. To finally stop saying maybe one day and actually start becoming who you're meant to be. And that's why I love Shopify. If you've got a dream, whether it's a side hustle you've been sitting on or something bigger, Shopify makes that first step simple. So let me ask you, what's the one thing you've always wanted to build but kept putting off? And how different could your year look if you just started now, if 2026 is your year, go to shopify.com imo and make your move. This episode of Imo is brought to you by Progressive Insurance who help people move forward and live fully. Owning a home can be one of the most powerful ways to build financial security. But for many, especially first generation buyers, it can feel out of reach. That's why I appreciate what Progressive is doing. In 2024, they contributed over $7 million to help individuals and families break the cycle of renting by providing support, offering educational resources and developing tools to build long term financial stability through home ownership. Their work goes beyond just insurance. They're opening doors through their newly created Up Payment program. Progressive is helping first generation home buyers move closer to the dream of home ownership by offering eligible applicants a chance to receive a down payment assistance grant. You know, owning a home for me made me feel grounded and also set me up for the future. And as a coach, when your life is dependent on wins and losses, it's really important to have the comfort of a really nice home to come home to, especially for your family. Homeownership is one of the biggest investments you'll ever make and Progressive wants to help more people take that life changing step. Learn more [e-mail]. openThe House. This episode of Imo is brought to you in part by Acorns. You know, one of the most valuable pieces of money advice I've ever gotten is that financial wellness isn't about how much you make. It's about making the most of what you have. That's something I've carried with me from my time on Wall street to today. And that's why I love Acorns. Acorns is a financial wellness app that makes it easy to start saving and investing for your future. You don't need to be rich. Acorns lets you get started with the spare money you've got right now. Even if all you've got is spare change, you don't need to be an expert. Acorns recommends a diversified portfolio that can help you weather all the market's ups and downs. You just need to stick with it, and Acorns makes that easy. Acorns automatically invest your money, giving it a chance to grow with time. The best advice I've gotten was from my father and that was to pay yourself first. So sign up now and join over 14 million all time customers who have already saved and invested $25 billion with Acorns. Plus, Acorns will boost your new account with a $20 bonus investment offer only [e-mail] IMO that's a C O R-N-S.com IMO to get your $20 bonus investment today from Acorns. Mighty Oaks do grow. Investing doesn't have to be complicated. Acorns makes it easy to invest for your future, plan for tomorrow, and spend smarter today. Paid non client endorsement compensation provides incentive to positively promote Acorns Investing involves risk. Acorns Advisor LLC and SCC registered investment advisor. View important [e-mail] IMO.

[Natalie]

Now, Margaret was your protector. I mean, in so many, at so many stages of your life, she was. She was being honest with you, protecting you from the truth, preparing you, making sure that you she was taken care of. And the reason why I want to talk about her, her second marriage. Your stepfather became one of the voices that could have made you think that you weren't worthy.

[Jonathan Capehart]

He was someone. You know, we can learn lots of lessons from people.

[Natalie]

Yes.

[Jonathan Capehart]

You know, good people and bad people. Good lessons and bad lessons. And I learned from him.

[Sa]

What not.

[Jonathan Capehart]

To do, how not to be, how not to treat people. And so if he did it or said it, I knew, you know, this is not right. This isn't kind. This isn't how you should treat someone. Or at least that's not how I'm gonna treat someone. And especially when I had someone like my uncle McKinley Branch, who was the complete opposite of him. I had the counterbalance. And he had been in my. Uncle McKinley had been in my life since birth. My favorite aunt and uncle, Annie Ann McKinley. And from him I learned what it meant to be, you know, a good dad, a good person, a good man. He was so caring and loving of his wife and his son, of the family writ large. I mean, Annie McKinley, they were like William and Kate in our family. They came that one. They came that way.

[Natalie]

And you spent time with them, too.

[Jonathan Capehart]

Yeah, a lot of time.

[Natalie]

When did you come out to them? Oh, and how.

[Jonathan Capehart]

I was going to bring my first long term partner down south for Thanksgiving. Grandma was still alive. And my grandmother said, yes, come on down.

[Natalie]

I want to. And she knew. She, yeah, wonderful. Yeah.

[Jonathan Capehart]

Oh, yeah, I want to meet him. And then I got a phone call from my grandmother about a week before Thanksgiving or two weeks, saying, I can't have that in my house. And I said, excuse me. You know, I was talking to so and so, and I just can't have that in my house. And I said, are you talking about Giuseppe? And I can't come down. And she said, no. And so I was heartbroken. And Grandma, we were close, super close. I didn't talk to her for a good two years after that. And it was Uncle McKinley who said to me, he called up and he said something like, I heard what happened. And I want you to know, Annie, and I want you to know that we love you and you are always part of the family and, and, you know, and Giuseppe. And it was all just. It was loving and affirming and he didn't have to do that. Yes, but he did. And you know, an African American man picking up the phone and calling to tell me that told me everything that I needed to know. Well, one, I already knew this about him, but the fact that he called me just sort of showed that this is a guy who pays attention and knew that I would be hurt by this.

[Natalie]

He knew you.

[Jonathan Capehart]

And called and wanted to make sure that I knew that, you know, don't get it twisted. We are here for you. We love you. And then I go and talk to Grandma. Grandma and I finally talk after a couple years of not talking. Come to find out she was fine. It was my Aunt Dorothy.

[Sa]

That's always Dot, Aunt Dot.

[Natalie]

Dorothy got in the grandmother got in her ear. You don't want none of that. Down here, she's like, maybe I don't.

[Jonathan Capehart]

Right.

[Natalie]

But it was good that you found out your grandmother's intent.

[Sa]

Oh, yeah.

[Natalie]

You know, where her heart was. I mean, I'm sure, you know, you can't win them all. And people will be who they are. I just sense in you, you know, just an internal security that isn't always there in young people as they are dealing with their sexuality. And you've continued to hold onto that. It's a reasonable man approach to things.

[Sa]

Yeah. And particularly a young. Particularly a young black man. Because, you know, I'm a little bit older than you. But in black families, being gay is tough. Cause we're tough on gay folks. And your level of security in yourself. Young people should look at that. And our mom always said, just be yourself. Never be afraid to be yourself. People will like you or they won't like you, but all the people who care about you will. It won't matter. They're gonna like you no matter what.

[Jonathan Capehart]

So as you get older, you soon realize. What? You don't like me.

[Sa]

Yeah.

[Jonathan Capehart]

Great.

[Natalie]

Yeah.

[Sa]

One less.

[Jonathan Capehart]

I don't care.

[Sa]

One less person to deal with.

[Jonathan Capehart]

Seriously.

[Natalie]

That's a good time to move into our listener question. Thank you, Jonathan. Thank you for that.

[Sa]

Yeah, yeah, we're not done yet.

[Jonathan Capehart]

Oh, okay. I'll settle back.

[Natalie]

Yeah. And Natalie will read it for us.

[Sa]

And this is from Dominic from Washington.

[Dominic]

D.C. i'm writing as someone who is hurting and feeling deeply frustrated. As the only openly gay man in my family, I often feel isolated, especially when spending time with my brothers. One is a professional athlete. And our social outings usually revolve around straight bars or environments where I feel like I can't fully be myself. Recently, I invited them to join me at a gay bar for the first time after going to multiple straight bars. And they wouldn't even come inside. They stood outside and waited. I ended up crying, feeling rejected and unseen later in the night. Am I wrong to feel frustrated? How do I keep showing up for my family who don't always show up for me? Dominic in Washington, D.C. wow, Dominic.

[Jonathan Capehart]

I have so many reactions. Please, so many emotions. One, I wonder how many. Like, where does Dominic fall in among the siblings? Is he older? Is he younger? Is he in the middle? Is he the Jam Brady of the family? Two, and this gets back to something that I said earlier about family. And maybe this is because I'm an only child and an only child of a widow who taught me to be self reliant. And it's being taught self reliance to the point where it is not hard for me to even say to family members, mm, mm. You're not gonna treat me that way. This is who I am. This is what I am on a whole range of issues. And if you don't like it, well, you will not have the pleasure of my company. And I wonder, Dominic, at a certain point, you are going to have to stand up for yourself, family or no family. Sometimes I think family uses the family tie to keep you, to keep you in place. And sometimes, you know, what if family's not treating you right in the same way that friends aren't or strangers aren't, at a certain point, family needs to learn who you are. And so those brothers of yours. I don't know how close the relationship is. It must be close if they're at least gonna come to a gay bar and stand outside. I don't know what that's about.

[Natalie]

Right, right.

[Jonathan Capehart]

But if they don't want to, you know, see you, you know, the full you by coming inside the gay bar. But at a certain point, you're just gonna have to, like, where is your chosen family? At a certain point, the real family has to give way to the chosen family. Because as you get older, family ties can be corrosive, toxic, not right. And sometimes it's difficult. But you're gonna have to say, you know what? You're not treating me right. I treat you with all the love and respect because you are my brothers. You are my family. But if you are not going to give as much as I give, well, I'm gonna have to go and take care of me, what makes me happy. And if that means we don't spend as much time together because I'm with my chosen family, where I am seen, where I am respected, in the end, that's what this is about. Family or no family, are you seen? Are you respected? Do people really care about you? And that's what you should feel. You shouldn't feel guilty in demanding that. Certainly of family, definitely of family.

[Natalie]

Do you think Dominic's potentially afraid of losing that connection? Because, again, you were an only child. The connection was different. What do you say to the kids out there who are. Do have they feel like, well, this, yes, I have a chosen family, but I don't want to lose this relationship to my brothers.

[Jonathan Capehart]

And I understand that and recognize that as an only child, I don't know what it's like to have brothers and sisters with all the teasing and the joshing and the talking over each other.

[Natalie]

And, yeah, it gets jeweled sometimes.

[Sa]

Yeah. Yes it does.

[Jonathan Capehart]

But you know, in the end, I think what I'm trying to get to is Dominic, when you know who you are, when you are just firm in your belief, like this is who I am, then everything else should flow from that. And that should dictate and determine how you relate to your brothers, how you relate to the rest of the family. I'm not saying, oh, just give up on them, dump them, tell them, bump you, I don't ever want to talk to you again. That's not what I'm saying. In the end, what I'm saying is, Dominic, learn who you are. And then once you know who you are, and by that I mean what do you like, what don't you like? What will you put up with, what you won't put up with? Just as a human being from people, regular everyday people, but also from family. And just because they're family, that does not give them a pass to not treat you with respect or the way you want to be treated. And so whether you are an only child or you are the middle of five, or the oldest of five, or the youngest of five, or however many, as long as you know who you are, then you will know how to navigate this and never, never stray from that. You will always be safe and secure when you know exactly who you are.

[Natalie]

How old did Dominic is? Dominic? Did he say?

[Jonathan Capehart]

Oh yeah.

[Natalie]

He didn't say. Yeah, yeah. Well, that's.

[Jonathan Capehart]

He strikes me as young, like maybe in his twenties.

[Sa]

Still not self assured yet. Right, right, right.

[Jonathan Capehart]

But you know, life has a way.

[Sa]

Of feeling, you know, in the end.

[Natalie]

It'S all about boundaries, you know, and it takes a while to learn what your boundaries are and then learn how to protect them. And that takes some practice. And Dominic, if you are young and you're just learning it, that's what you know. You're gonna have to figure that out for so many levels of your life. Cause if you're not able to do it with your brothers, you're probably not doing it on the job. You may not be doing it with your chosen family and friends. And that's, that's work that you know at some point you can't avoid that, right?

[Jonathan Capehart]

There's sacrifice. There's sacrifice in when you set boundaries. You then learn who your friends are and really sometimes who your family is and with that sacrifice. So you have to be comfortable in the sacrifice. I know because of the boundaries I've drawn and the things that I won't do that I probably limited opportunities for myself. And you know what? I am just fine.

[Natalie]

Just fine with that.

[Jonathan Capehart]

Just fine with it. You have to be just fine with the known sacrifices that come with setting those boundaries.

[Sa]

You know, January always feels like that moment to hit reset, to finally stop saying maybe one day and actually start becoming who you're meant to be. And that's why I love Shopify. If you've got a dream, whether it's a side hustle you've been sitting on or something bigger, Shopify makes that first step simple. So let me ask you, what's the one thing you've always wanted to build but kept putting off? And how different could your year look if you just started now, if 2026 is your year, go to shopify.com imo and make your move. You know, whatever you're focused on right now. Work, family, big goals. There's never a perfect time to feel your best. There's just right now. AG1 has honestly been the easiest, most impactful habit I've added this year. Real sustainable health isn't about perfection, it's about consistency. And AG1 keeps it simple. Multivitamin, pre and probiotics, superfoods, antioxidants, all in one scoop. And AG1 is the opposite of complicated. One scoop, 8 ounces of water, about 20 seconds. I drink mine first thing in the morning, before coffee, before the phone. It's become this little microhabit that sets up the whole day. And the new next gen formula has more vitamins and minerals than ever clinically proven to help fill common nutrient gaps. I use this every single day and you should too. They've got original citrus, berry and tropical and I'm an original and citrus guy myself. AG1 has over 50,000 verified 5 star reviews and comes with a 90 day money back guarantee. Go to drinkag1.com imo to get their best offer. For a limited time only, get a free AG1 duffel bag and a free AG1 welcome kit with your first subscription order only while supplies last. That's drinkag1.com IMO. Drinkag1.com IMO January always puts me back in the reset mindset. I'm not trying to overhaul my life. I'm trying to feel better by creating good, simple wellness habits. Whole Foods Market is where I start. I'll pick up a multivitamin or protein powder I trust. And for when I'm short on time but still want to cook a simple dinner, I'll grab a wild caught sockeye salmon and one of their 365 salad kits. My favorite if you're ringing in the new year with dry January. They've got great non alcoholic drinks that don't feel like a compromise, which makes sticking with my healthy habits more enjoyable. It's wellness that actually fits into real life. Shop all things wellness at Whole Foods Market.

[Natalie]

And on the other end of that, those boundary settings, there's room for new, better, more. Because if you free yourself up from the things that don't serve you and bind you down, you'd be surprised, Dominic, that there's room for something really special in there. I mean, you talk in your book, Jonathan, about your chosen family, this beautiful New York life that you've built for yourself. And having that attitude, you know, led you to what felt as you described it, this amazing community of support, full of diverse people who accepted you. And the dinners that you all would have together, the travel, what that all did to expose you. You developed a love for other countries and because you created some boundaries that opened up opportunities to bring other people into your world.

[Jonathan Capehart]

And also with this New York family, as I read, I met these people through a friend who said, come to this party. And then he didn't come to the party, but I walked into this room that felt like just a giant hug because in the room were other nerds, other black nerds. They're not gonna like that. I call them that. But these were.

[Natalie]

They're special, right?

[Jonathan Capehart]

Well, these were African American mostly, not all, but young professionals to whom I didn't have to explain anything. They knew, they understood where I was coming from. Similar backgrounds. We all watched Soul Train Saturday Morning. We all knew the music and the songs, and we bonded over that from disparate parts of the country. And here we are in New York, young black professionals, and we have this common language and we have these common aspirations. We came to the city to do stuff, to make names for ourselves, to just forge a life on our own. And when you realize that you, especially for an only child of a widow who had this destination with no roadmap, doing all this stuff on my own. And I walk into this room and I'm surrounded by people who are all doing the same thing, generally speaking, but come from different backgrounds and different sized families, and we all have this common cultural ancestry. I mean, just the shoulders come down. I mean, that's why Martha's Vineyard is such a special.

[Natalie]

Yeah.

[Jonathan Capehart]

Such a special place. That is a place where shoulders come down, come down. That is my New York. This family was formed in the mid-90s in New York. And then, you know, come to Martha's vineyard in, you know, my tender age, you know, late early 50s. And again, it's that place where the shoulders come down. I am with. I am with friends who I know from outside the vineyard, but we're there and we don't have to explain a lot, if anything, and sometimes we just. We need to have those places.

[Natalie]

And I would encourage Dominic to focus his energy on building that place. You call it the chosen family. And it's not to replace the current family, but we all have a chosen chosen families. I mean, I love my brother, but he's not coming to the venue. I come to the venue. I come to the venue. Thank God for my chosen family, because my actual family is not choosing me.

[Sa]

Just hit your brothers one at a time, one at a time. Take them out one at a time. Find out which one is the leader and which one you can pick off, and then slowly get them into your chosen family.

[Jonathan Capehart]

That's actually a good point. Why are you doing all this stuff with all of them? Which one are you closest to? And just go and just hang out.

[Sa]

With him and do that with each one. And I think life is individual relationships.

[Jonathan Capehart]

Yep.

[Sa]

Jonathan, thank you.

[Natalie]

Jonathan, you are a beautiful storyteller and your life is it. It is rich. And thank you. Thank you for your willingness to share it and thank you for being out there on the front lines fighting for our democracy. It is sometimes thankless work, but you do it with grace.

[Jonathan Capehart]

Thank you. It's a calling.

[Natalie]

Yes, it is. It has been a calling from the time you read in the National Geographic. It's a little kid, a little bit kid.

[Sa]

But appreciate the truth.

[Natalie]

It is a. It is. It is such a pleasure.

[Jonathan Capehart]

Oh, thank you. This is fun.

[Sa]

Sa.