IMO with Michelle Obama and Craig Robinson, “Find Your Adventure with Katt Williams”

Host: Higher Ground | Date: December 3, 2025

Episode Overview

In this episode, Michelle Obama and her brother Craig Robinson are joined by acclaimed comedian Katt Williams for a heartfelt, humorous, and deeply personal conversation. Together in a relaxed setting at Martha’s Vineyard, they explore Katt’s extraordinary journey—from a challenging childhood and early independence, to parenting, adopting children, and his storied comedy career. The trio also tackle a listener’s dilemma on making bold life moves, while trading candid reflections and plenty of laughs.

Key Discussion Points & Insights

1. Setting the Scene and Katt Williams’ Introduction

• The episode kicks off with Michelle and Craig discussing the beautiful “barn” in Martha’s Vineyard where they’re recording, setting a warm and intimate tone.
• Katt Williams joins the conversation, greeted with humor about his stature and reputation ([03:22]).
• Conversation quickly pivots to golf—a passion of Katt’s, offering insight into how hobbies influence personal growth.

Notable Quote:
“You and your husband are one of only a handful of actual superheroes we've seen in the country. And superhero is somebody you put ungodly expectations on...when we look back 100 years from now, you were the source of pride for a nation that needed that.” – Katt Williams ([07:58])

2. Golf and Lessons for Life

• Katt shares how golf became a transformative retreat, teaching him about humility, persistence, and letting go of both failures and successes ([04:39], [06:03]).
• Michelle and Craig discuss efforts to increase Black youth participation in golf and invite Katt to join their initiatives in Chicago ([07:01]).

3. Katt’s Upbringing: Childhood, Independence, and Books

• Katt reflects on a childhood lacking overt affection but rich in parental support, leading him to turn negative circumstances into resilience, with books as an early escape and source of strength ([09:27]).
• He recounts realizing at age six the challenges ahead, comparing himself to classic underdog heroes (“Poor girl. Cinderella – Stepmother’s awful... I’m right on track.” – Katt Williams, [11:13]).
• Reveals his parents’ strict religious background as Jehovah’s Witnesses, limited extracurriculars, and how reading shaped his worldview ([13:54], [14:06]).

4. Adoption and Parenting

• Katt candidly describes how he came to adopt his son’s siblings after their birth mother’s struggles, marking a pivotal period in his life and career ([15:44]).
• Parenting forced him to “grow up,” shifting his mindset from bachelorhood to full-time father.
• Discusses the heartbreak of losing a child and the enduring pain that comes with it, highlighting the difficulty and depth of love in parenting ([18:54]).

Notable Quote:
“The hardest part is...losing a child is probably the worst thing that can happen to you on this earth. There's no recovery from it. There's no...” – Katt Williams ([18:54])

5. Parenthood, Special Needs, and Empathy

• Parenting special needs children, especially a daughter with autism, gave Katt a new lens on patience and unconditional love ([23:45]).
• The group discusses the show "Love on the Spectrum" as an example of pure-hearted relationships and learning from those with autism ([24:40-25:32]).

6. Leaving Home and Surviving on His Own

• Katt recounts leaving home at 13, setting off with a suitcase and a Rottweiler puppy, working odd jobs, and supporting himself as a young entrepreneur in Miami ([26:54], [28:11]).
• He describes sleeping in parks, learning from people who had lost everything to addiction, and eventually being found by his parents by chance years later ([36:12]).
• Lived in Haiti with his family for two years, where he learned French and Creole and helped with community work ([41:10]).

Memorable Story:
“I had a full suitcase and a Rottweiler puppy. ...I checked license plates because I was looking for a warm destination, and...Miami presented itself, and the guy let me and the Rottweiler puppy get in the back part of the empty truck.” – Katt Williams ([28:11])

7. Comedy, Door-to-Door Sales, and Character-Building

• First stand-up appearance happened accidentally after tagging along with carnies to a club ([49:01]).
• He connects his confidence on stage to years of public speaking as a Jehovah’s Witness and his adaptability from selling door-to-door—crucial skills for stand-up ([51:47], [54:00]).
• Tells the wild story of briefly acting as a “pimp” for women who had lost their previous protector, learning about men from their candid discussions ([54:57], [55:22]).

8. Advice for Aspiring Artists

• Katt attributes all progress to his relationship with God, recommending artists take the existential pressure off themselves and instead “work on” their faith ([61:41]).
• Encourages building relationships spiritually as a foundation, whether for art or life.

Notable Quote:
“If you believe in God, take as much pressure off of yourself as you can and apply that pressure to him...It doesn’t matter how young you get that relationship. It’s never too early.” – Katt Williams ([61:41])

9. Relationships and Personal Life

• Never married, Katt admits monogamy has not been a part of his journey, largely due to his adopted family responsibilities and not wanting to bring someone into a complex situation ([64:14]).
• Lives on a large farm, which he describes as his own “heaven on earth”—a philosophy reflected in both his current life and his comedy tour ([66:25]).

10. Work Ethic, Career, and Meeting Prince

• Describes his annual touring ritual as akin to athletic seasons—100 shows, then a special ([67:31]).
• Shares a formative story about meeting Prince as a child, learning confidence and inspiration to be unapologetically himself despite his own perceived shortcomings ([68:13]).

Notable Quote:
“Prince helped me see immediately I didn't have to get taller. ...I just had to be in the right position and be right myself when it transpired. So super helpful, that guy.” – Katt Williams ([71:53])

Listener Question Segment

Amber, San Antonio, TX (Listener from [72:45])
Q: How did you move through the fear of stepping into something new?

• Katt Williams’ Advice ([74:13]):
  • Fear is useful and necessary; it ensures you take new opportunities seriously.
  • “You’re only going to look back and go, I should have left earlier. ...Never stop being in search of your calling and your purpose.”
• Craig Robinson & Michelle Obama ([76:19], [78:32]):
  • Fear should not paralyze you—take it as a sign that stakes are high but growth awaits.
  • “If you practice moving away from fear, you just practice always feeling safe. But you’ll look around and realize ...you won’t be happy.”
  • Michelle notes that repeated experience lessens the sting of fear, and “the first hard pivot is the hardest; then you build that muscle.”

Notable Quotes & Moments

• “Money Micah early.” (Katt Williams on his school hustle, [31:03])
• “There’s no such a thing as doing a great job [in parenting]. There’s just such a thing as doing a bad job. ...If you’re doing a good job, that should take a lot of the panic and anxiety away from you.” – Katt Williams ([23:45])
• On resilience: “Life is always worth the next adventure. And so that’s how I was looking at things, even that early.” – Katt Williams ([11:36])
• “I suppose monogamy has not been a part of my journey. ...I’ve tried to share this gift with whoever would need it.” – Katt Williams ([65:47])
• On stage fright: “Every time I have to do stand up, I’m as nervous and direct as I was the very first time...it never has gone away. It’s what allows me to realize something’s counting on this. You must do well.” – Katt Williams ([79:19])

Memorable and Humorous Moments

• Katt’s vivid story of leaving home at 13 with a Rottweiler puppy, heading for Miami with $1,200 from summer jobs ([28:11]).
• The surreal “homeless hierarchy” in Miami parks and buying a mattress delivered to a park ([33:03]).
• Michelle’s incredulity at Katt’s adventurous youth: “Like, are you telling the truth or are you joking?” ([33:05])
• Craig on Katt’s farm: “You have a farm. There’s so many kind of little surprising layers.” ([66:15])
• Katt’s quip: “Heavy on the layers.” ([80:57])

Timestamps for Important Segments

• Golf, Performance, and Life Lessons: [03:33]–[07:01]
• Early Childhood/Reading and Resilience: [09:27]–[14:34]
• Adoption & Parenting: [15:44]–[20:27]
• Life on Own at 13, Survival in Miami: [26:54]–[33:43]
• Haiti Adventure & Giving Back: [41:10]–[43:21]
• Comedy Origin Story: [49:01]–[51:47]
• Advice to Aspiring Artists: [61:41]
• Listener Q&A – Overcoming Fear (Amber): [72:45]–[80:26]

Concluding Remarks & Tone

The conversation maintains a warm, humorous, contemplative tone, blending Katt’s trademark wit with thoughtful reflection from both hosts. The episode is rich in anecdotes, life lessons, and candid admissions—making it both laugh-out-loud funny and deeply moving. Katt’s layered narrative, paired with the Obamas’ empathetic hosting, creates a space where vulnerability and humor coexist, encouraging listeners to embrace their adventures, fears, and growth.

For listeners seeking wisdom on resilience, reinvention, and joy—seasoned with Katt Williams’ one-of-a-kind perspective—this episode is both a masterclass and an adventure.