Issa Rae

Issa Rae is entering a new chapter — not from the bottom, but from experience. After disrupting modern television with shows like HBO’s Insecure, building business across multiple industries, and creating some of the most culturally resonant work of the last decade, Issa sits down with Emma for a reflective conversation about power, execution, and what it really means to build something that lasts. Issa isn’t into chasing momentum. She’s moving discernment— navigating the industry on her own terms and only committing to work she genuinely believes in. In this episode, Issa opens up about: Why ideas are meaningless without execution The difference between visibility and real power What it means to “prove yourself again” — even at the top How she decides what not to do in this phase of her career Why money equals creative freedom, not validation The discipline of saying no, protecting her voice, and building on her own terms Her desire to continue to make people’s favorite content. Issa also reflects on leadership, ownership, and the responsibility that comes with influence — especially in an industry that feels like it’s regressing. This conversation is for anyone navigating a new chapter, resisting comfort, or learning that longevity requires a different kind of courage. What resonated most with you from Issa’s journey — her discipline, her clarity, or her refusal to rush? Share your thoughts in the comments and subscribe for more honest conversations on Aspire. 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

Join our Patreon for extra-long episodes and ad-free content: https://www.patreon.com/techish This week on Techish, Michael and Abadesi unpack why Issa Rae doesn’t feel successful despite, well, all her success; Donald Glover’s revelation that he suffered a stroke and had a hole in his heart; and why Pharrell Williams can’t simply opt out of politics. And for the Patreon fam: the uproar on Chinese social media after a man who froze his wife was spotted with a new partner. This episode is sponsored by DeleteMe. Get 20% of DeleteMe at joindeleteme.com/techish with code TECHISH. Chapters 00:23 Issa Rae, Donald Glover, And The Truth About Success 13:10 Pharrell Williams Says Politics Isn’t Real 20:55 Man Who Froze His Wife Now Has A New Girlfriend [Patreon-Only] Extra Reading & Resources Issa Rae Reflects on Highs, Lows, and the Fear of Losing It All | Not My Best Moment with KevOnStage [YouTube] Childish Gambino Reveals He Suffered a Stroke: ‘They Found a Hole in My Heart’ [VICE] Pharrell Williams Reveals His Political Stance, Says Picking Sides Inadvertently Supports ‘Division’ [Complex] Man who cryogenically froze late wife sparks debate by dating new partner [BBC] Support the show Join our Patreon for early content, extra-long episodes and ad-free content: https://www.patreon.com/techish Watch us on YouTube: https://www.youtube.com/@techishpod/ Advertise on Techish: https://goo.gl/forms/MY0F79gkRG6Jp8dJ2 ———————————————————— Stay in touch with the hashtag #Techish https://www.instagram.com/techishpod/ https://www.instagram.com/abadesi/ https://www.instagram.com/michaelberhane_/ Email us at techishpod@gmail.com

In ⁠One Nightstand⁠ , celebrity readers and writers join us at ⁠The Blond⁠ in ⁠11 Howard⁠ to discuss their favorite books.In this episode, writer, producer, and actor Issa Rae sits down with Charlotte Owen to discuss her new book, I Should Be Smarter by Now . Issa shares why life is better after your 20s, the book she’s desperate to adapt, and what she “romanticized” in her hit HBO series Insecure . The Courage to Be Disliked: How to Free Yourself, Change Your Life and Achieve Real Happiness by Ichiro Kishimi and Fumitake Koga The Wilderness by Angela Flournoy Eleanor Oliphant Is Completely Fine by Gail Honeyman Great Black Hope by Rob Franklin I Should be Smarter by Now by Issa Rae Issa’s new collection of essays, I Should Be Smarter by Now, is available now on Amazon and Audible. Credits Director/Director of Photography: Marshall Stief Assistant Camera: Jasmin Velez Post Supervisor: Delia Kelly Post Production Manager: Mateo Delgadillo Editor: Alex Viola Producer: Aubree Lennon

#ads Get premium access to stream any unabridged audiobook by starting your free trial: https://mediabooks.space/il-3924/ Title: The Business of Being Me Series: I Should Be Smarter By Now Author: Issa Rae Narrator: Issa Rae Format: mp3 Length: 34 mins Release date: 08-26-25 Ratings: 4.7 out of 5 stars, 56 ratings Genres: Entertainment & Celebrities Publisher's Summary: Even at seven years old, Issa Rae meant business, conducting herself with entrepreneurial authority on a toy phone in her bedroom. Eventually, it was a matter of convincing others that she had a lot to say and getting them to listen. From her first web series, Awkward Black Girl, to network disappointments to HBO triumphs, Issa charts her aspirational journey—self-doubts and all—of being taken seriously, finding her voice, and shaping it into a groundbreaking career.

#ads Get premium access to stream any unabridged audiobook by starting your free trial: https://mediabooks.space/il-3924/ Title: I Almost Know What I'm Doing Series: I Should Be Smarter By Now Author: Issa Rae Narrator: Issa Rae Format: mp3 Length: 29 mins Release date: 08-26-25 Ratings: 4.7 out of 5 stars, 25 ratings Genres: Entertainment & Celebrities Publisher's Summary: It’s a gamble to bet on yourself in Hollywood. But Issa Rae placed it. Charting her evolution from struggling writer to media mogul, she pulls back the curtain on her ever-evolving career in an always-changing industry and reveals that the best investment she made was her belief in herself. As she reflects on weathering storms and lessons learned, Issa moves forward with renewed purpose.

😂 Awkward, Black, and unapologetically herself—Issa Rae changed the game. In The Misadventures of Awkward Black Girl, Issa Rae delivers a hilarious, relatable, and sharp-witted memoir about growing up as an introverted Black girl in a world that often misunderstands both. Before she was the creative powerhouse behind Insecure, Issa was navigating cringe-worthy social situations, cultural expectations, and the struggle of just trying to “fit in” while standing out. Join our AI hosts, j(AI)n and d(AI)n, as we break down Issa’s unique brand of humor, her journey to becoming a media mogul, and what it means to embrace your awkwardness as a superpower. Why do we feel pressured to “perform” in social spaces? And how did Issa turn her quirks into a cultural revolution? Let’s get into it. 📖 Purchase Awkward Black Girl on Amazon: https://amzn.to/3X3pBvb 🎧 Listen to the audiobook on Audible: https://amzn.to/4b4CHhu ✨ Subscribe to our newsletter https://whttr.beehiiv.com/subscribe 🌐 Visit our website https://whttr.wordpress.com Disclaimer: Some links contain affiliate links, meaning WHTTR will earn a small commission when you purchase through our link at no additional cost to you. As an Amazon Associate, we earn from qualifying purchases. #AwkwardBlackGirl #IssaRae #BlackGirlMagic #IntrovertStruggles #HumorMemoir #RepresentationMatters #WHTTRReads #BookDiscussion #LiteraryDeepDive #Podcast #SpotifyPodcasts #YouTubePodcasts

In this episode of It Takes a Village, Delina welcomes Issa Rae for a candid discussion covering various facets of her life and career. Issa Rae is a dynamic force in entertainment, known for creating and starring in the Peabody-winning series, Insecure, and for her roles in Barbie, Spider-Man: Across the Spider-Verse, and American Fiction. As the founder of HOORAE Media, Issa champions diverse storytelling across film, TV, and music. Issa’s commitment to her community in South LA shines through her investments in local businesses, including Hilltop Cafe + Kitchen, Somerville, and Sienna Naturals, a Black-owned vegan hair care line. Issa discusses her creative journey, from the early success of Awkward Black Girl to becoming a creative producer, and shares insights into the challenges of the industry, including casting, auditions, and balancing creative control on set. Rae talks about her entrepreneurial ventures and how she navigates business, and the importance of choosing investments that align with her values. Rae also shares stories about her family background, creative process, waking up early, and balancing multiple projects, painting a comprehensive picture of her approach to both her professional and personal life. Listen to Issa Rae’s inspiring story of innovation, perseverance, and creative excellence. As she says, "I’m committed to breaking boundaries and pushing the envelope," and this episode is full of wisdom for anyone striving to make their mark. Tune in now for an unforgettable conversation with one of today’s most influential creators. Learn more about Issa Rae: With her own unique flare and infectious sense of humor, Rae first received attention for her award-winning web series and the accompanying New York Times best-seller, “The Misadventures of Awkward Black Girl.” She created and starred in the Peabody-award-winning HBO series, INSECURE, which garnered her multiple Emmy® and Golden Globe® nominations. Rae has also made her mark on the big screen, co-starring in Greta Gerwig’s BARBIE, which dominated theaters as the biggest box-office hit of 2023, SPIDER-MAN: ACROSS THE SPIDER-VERSE, Sony’s highest-grossing animated release in history and the award-winning AMERICAN FICTION. In 2020 Rae formed HOORAE, a multi-faceted media company that develops content across mediums in an effort to continue to break boundaries in storytelling and representation. HOORAE is comprised of HOORAE Media for film, tv and digital; Raedio, the music label, music supervision and "audio everywhere" company; ColorCreative, its management division; and FÊTE its marketing arm. Rae's commitment to South LA is evident in both her personal and professional pursuits. After planting roots near her childhood home, Issa set up the HOORAE headquarters in the heart of South LA. Her participation in the non-profit organization Destination Crenshaw furthers her mission of celebrating Black Angelenos and her ownership in Hilltop Cafe + Kitchen provides much-needed jobs and opportunities for local residents as well as a space for creatives to unlock their potential. Additionally, as co-owner of the Black owned and operated vegan hair care line, Sienna Naturals, Rae intends to continue to reimagine Black wellness and beauty. Rae recently launched Viarae Prosecco, a sparkling wine that's perfect for any occasion and represents the freedom to let loose and be authentic. Connect with Issa Rae: @issarae Listen to more episodes of It Takes A Village podcast: ⁠ It Takes A Village with Delina Medhin⁠ Stay updated on everything It Takes A Village podcast: <

These queens rose to fame on HBO's hit show Insecure (which Issa created), but the show also laid the groundwork for their so-called rivalry. Will they make up and become besties? We may never know - but we know they've helped each other, and Black Hollywood, immensely. Subscribe for monthly bonus episodes patreon.com/2Queens2Crowns Join the conversation: TikTok - ⁠@2queens2crowns⁠ , ⁠@iam_kjmiller⁠ , @leta_bitchknow⁠ YouTube - ⁠2 Queens 2 Crowns⁠ IG: ⁠@kjmiller⁠ ⁠ @letabknow Episode Links: How Insecure Opened Doors for Black Creatives in Hollywood Issa Rae looks back on making it big–and making big mistakes Amanda Seales Reacts to Rumors She Was a 'Mean Girl' on 'Insecure' Set Issa Rae, Who Grew Up in Potomac, Ends Successful Five-Year Run of Her Show ‘Insecure’

Issa Rae shares her tips for success as a creator and business owner. In today’s episode of the Rundown with Ramon, hosted by small business expert Ramon Ray, publisher of ZoneofGenius.com we also share about the rivalry with two private jet industry owners; insights from Amazon’s thousands of sellers and more. Issa Rae’s Keys to Success Acclaimed producer and actress Issa Rae shared some of her strategies for success with Business Insider . Waking up at 4 AM as her “cheat code” for productivity Using early mornings for workouts and journaling Hiring a TV producer as her first and most essential team member Valuing honesty in collaborations and partnerships Finding environments outside the home to boost creativity Ramon discussed the ongoing feud between two private jet charter companies via the WSJ , highlighting an important lesson for business owners: Focusing on mudslinging and personal attacks can be detrimental It’s often better to ignore competitors and concentrate on building your own brand and serving customers A Scotiabank survey revealed that many small business owners lack succession plans: 48% of Canadian small business owners plan to exit their businesses within the next decade 43% of those planning to exit within six years are not well-prepared Ramon recommends John Warlow’s books on business exit strategies Key findings from Amazon’s 2023 report on independent sellers : Over 10,000 independent sellers surpassed $1 million in sales for the first time U.S.-based sellers exported over 330 million items globally Independent sellers employed more than 1.8 million people Over 100,000 sellers used Amazon’s AI listing tools Rural sellers grew sales by more than 60% Maria Cho discussed her company’s work in synthetic food technology: Using biotechnology to create sustainable food sources Leveraging AI in research and development processes Emphasizing the importance of company culture and values Encouraging women to get involved in STEM and AI fields Time Magazine explored why some people need more sleep than others: Sleep needs change throughout our lifetimes Factors like gender, genetics, and sleep disorders can influence sleep requirements Understanding your personal sleep patterns can lead to better rest and productivity A CDC study, via USA Today , revealed interesting traits of landline phone owners: More likely to live in the Northeast Tend to have healthier lifestyle habits Less than 25% of Americans still own landlines Ramon Ray’s Rundown provides a diverse mix of business insights, technology trends, and personal

On this episode of Gen X Amplified, I am welcoming back serial entrepreneur Ian Schafer, repeat guest and friend of the podcast, for another round of "Gen Xceptional" wisdom and inspiration. Ian is the President and Co-Founder of Ensemble , a next-generation branded entertainment studio that he co-founded with acclaimed producer, writer, actress, and entrepreneur Issa Rae. Ensemble collaborates with brands, platforms, and publishers to produce and distribute epic content and activations that shape culture, engage audiences, and move product. Ian, Issa, and the team at Ensemble is on a mission to make the creator economy more equitable for creators from underrepresented communities. In this episode, Ian and I unpack: Ian's experiences and journey as a founder, particularly during the disruptive landscape of the 2020 pandemic The story of how Ian began his business relationship with Issa Rae and her team at HOORAE Media to launch Ensemble Why Ensemble's mission is focused on creators from underrepresented communities The overall state of the creator economy, especially in the age of AI Why mid-career professionals (i.e, Gen X) can thrive and create value in the creator economy based on their seasoned experience and expertise, coupled with deep knowledge and unique insights. And more! Ian's Personal Theme Song "Electric Relaxation" by A Tribe Called Quest About Ian Schafer Ian is an award-winning global brand, marketing, advertising, and sports & entertainment entrepreneur and executive. He is and currently the Co-Founder of Ensemble , a next-generation branded entertainment studio that he co-founded with acclaimed producer, writer, actress, and entrepreneur Issa Rae. Ensemble collaborates with brands, platforms, and publishers to produce and distribute epic content and activations that shape culture, engage audiences, and move product. Ian is also a strategic advisor to ROCK THE BELLS, the preeminent voice for classic and timeless hip-hop founded in 2018 by LL Cool J. Also, Ian is the co-founder of ON_Discourse, owner of Queensboro FC, and an advisor to Accelerator. Previously, Ian Co-Founder & CEO of Kindred, a membership organization that's on a mission to build a more equitable society by advancing the actions of today's leaders. Prior to launching kindred, Ian was the founder, CEO, and Global Chairman of Deep Focus, a transformative advertising agency that eventually he sold to Engine Group in 2015. Before he began his entrepreneurial journey with Deep Focus, Ian worked at Miramax Films as the VP of New Media, where he learned many lessons on the power of content and innovation. Previously, Ian started his career as a Sr. Account Executive at i-Traffic, which was one of the first digital agencies in the world. In 2015, he was inducted into the American Advertising Federation's Hall of Achievement, named one of "100 People Who Make Advertising Great" by the 4A's in 2017, and was also named named a "Media Maven" by

Writer, actor and producer Issa Rae commented to Terry Gross, host of the NPR show Fresh Air, that she was socially uncomfortable and introverted growing up, and one day wrote the phrase "I'm awkward. And black." in her journal. Rae says it was a revelation. "I knew I was black, obviously, but the 'awkward' part really just defined me in a sense," Rae noted. "That felt like an identity that I had not seen reflected in television or film before, or at least in a very long time." Terry Gross : "So what made you think that the parts of your life that made you feel awkward and insecure you could claim as an identity and then use that to your advantage and create a character who would be kind of like funny and relatable and everything. "And that so you could turn what you perceived as like your weakness into a strength." Issa Rae: "Well, for me, it came from watching shows like Seinfeld and Curb Your Enthusiasm, and even 30 Rock, and just identifying with the very specific sense of humor that those shows had, but also being like, wow, there are no people of color in these shows that have the same sense of humor, you know? "Wondering like why is there this segregated humor? There seems to be like black humor and there seems to be white humor and you know a lot of my friends...we like both, but we don't get to see ourselves reflected on the quote-unquote white humor side. "And so I wanted to take these traits in the same way that, you know, a lot of my favorite comedians have done it, and Ellen included. Ellen takes so many relatable, embarrassing moments and amplifies them and makes it like, Oh my god, I've been through that too, and that's so funny. "And have a black character go through those things and make it very racially specific but universal at the same time." (See the transcript for more.) ~~~ Show notes for the Fresh Air podcast interview summarizes: "Her Web comedy series The Misadventures of Awkward Black Girl [based on her memoir] ran for two seasons, and Rae continued to explore themes of race, identity and belonging as the creator and star of the HBO series Insecure." This audio in an excerpt from that interview. Fresh Air episode with Terry Gross (on NPR): 'Awkward' And 'Insecure' Get To The Root Of Writer Issa Rae's Humor. video: Issa Rae Teaches How to Get Out of Our Own Way and Create Content Successfully Learn about MasterClass " Issa Rae Teaches Creating Outside the Lines " Related Substack/Creative Mind posts/podcast episodes: ~~~~ This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit thecreativemind.substack.com/subscribe

Max rebooted Project Greenlight and this relaunch focuses, under the guidance of Issa Rae as Executive Producer, on the next generation of diverse, up-and-coming talented female filmmakers who are given the chance to direct a feature film. In the first season that filmmaker is Meko Winbush. I've had a chance to watch the whole season and the film they made, called Gray Matter. As a fellow filmmaker, I wanted to share some of my thoughts. So check it out and please share your thoughts down in the comment section or hit me up on social media @PhilSvitek. Also, you're welcome to check out the Variety article I referenced here: https://variety.com/2023/tv/news/project-greenlight-meko-winbush-directing-issa-rae-1235670646/ , which includes what Meko thought of her mentors Issa, Kumail Nanjiani and The Woman King director Gina Prince-Bythewood. Lastly, for more free resources from your 360 creative coach, check out my website at http://philsvitek.com . RESOURCES/LINKS: -Coach or Consultant Services: https://philsvitek.com/lets-work-together/ -Podcast Services: http://philsvitek.com/podcastservices -Love Market Film: https://www.amazon.com/Love-Market-Amy-Cassandra-Martinez/dp/B09DFS3FTZ/ref=sr_1_14 -Patreon: https://www.patreon.com/philsvitek -Merchandise: https://shop.spreadshirt.com/phil-svitek---360-creative-coach/ -Instagram: http://instagram.com/philsvitek -Facebook: http://facebook.com/philippsvitek -Twitter: http://twitter.com/philsvitek -Financially Fit Foundation: http://financiallyfitfoundation.org -Master Mental Fortitude Book: http://mastermentalfortitude.com -Elan, Elan Book: http://philsvitek.com/elan-elan -In Search of Sunrise Book: http://philsvitek.com/in-search-of-sunrise -A Bogotá Trip Film: https://philsvitek.com/a-bogota-trip/