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Tell Your Story with Jonathan Capehart - IMO with Michelle Obama and Craig Robinson | Wave AI Podcast Notes

Back to IMO with Michelle Obama and Craig Robinson

Tell Your Story with Jonathan Capehart

IMO with Michelle Obama and Craig Robinson

Wed Jan 07 2026

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

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.

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)

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)

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)

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)

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.

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)

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]

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.

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

Loading summary...

Transcript

Jonathan Capehart (0:00)

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 (0:19)

Stop.

Natalie (0:20)

Stop there. Mom. K part with your bins.

Jonathan Capehart (0:25)

I know, with her bins.

Dominic (0:26)

She was like.

Natalie (0:26)

And we going down White street in our bins.

Jonathan Capehart (0:28)

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 (0:41)

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

Sa (0:48)

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 (0:56)

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

Sa (1:00)

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 (1:16)

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

Sa (1:20)

Enough about my night.

Natalie (1:22)

Uh huh. Yeah.

Sa (1:24)

We have a guest here.

Natalie (1:25)

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 (1:54)

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.

Sa (16:48)

This episode of IMO is brought to you by theraflu. Theraflu, makers of Fast Acting Cold and Flu Relief, believes everyone deserves the right to rest and recover when they're sick, no matter where they live or how much money they make. When I was coaching, if I got sick, I found it hard to choose between taking time for myself to rest and heal and showing up for my family and my team. Luckily, I had the ability to take paid sick time when I really needed it. But not every American has that option. In 2021, Theraflu launched the Rest and Recover Fund and they've committed more than $1 million to provide micro grants to families and individuals, helping offset the cost of taking a sick day for those that don't have coverage. Everyone should be able to prioritize their health without risking their ability to put food on the table. That's why Theraflu is committed to keep fighting, because rest and recovery is a right, not a privilege. Learn more or help someone. Apply for the fund@theraflu.com right to recover this episode of Imo is brought to you by Indeed. Typically your college major is unlikely to be your profession, and that's certainly the way it was for me. So it's really important to be extremely flexible and open minded about what you're willing to pursue. Think broadly in your search. That's why it's important to think outside of the box and tap into your skills for your next career move. Indeed Career Scout can help you land your next role fast leveling up your job search process with personalized recommendations and support. Being open to change helped me explore roles I hadn't imagined, which made my career richer and more fulfilling. Indeed Career Scout can help you do the same by connecting you to opportunities you might not have considered based on your skills and interest. It's like a personal career coach that makes every part of the job searching process easier. It can tailor your resume for specific applications, match you with new opportunities, and even help you practice your interviews. Indeed's mission is to empower people to use their skills to find better work and and Career Scout is their latest innovation to help you do that. The future of job searching is here and it's called Indeed Career Scout. Try it today in the Indeed app.

Jonathan Capehart (21:41)

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.

Jonathan Capehart (27:30)

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 (36:54)

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Sa (54:56)

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