Nice Talk with Nikki Ogunnaike

So nice we’re releasing it twice! Today we’re revisiting Issa Rae’s Nice Talk episode.
Issa Rae truly does it all. Not only is she a multifaceted entertainment powerhouse, but she also runs businesses in various industries—from prosecco to food to haircare. Today on the show, the former Marie Claire cover star joins us to talk about money, power, and style, including how she crowdfunded her early projects like Awkward Black Girl, how she overcame "grateful to be here" energy after partnering with HBO, and what it means to be boldly elegant in her style. She also tells us about her newest projects: her book I Should Be Smarter by Now and her two-part docuseries Seen & Heard. Plus, Rae shares why creativity is not the most important trait to be successful in the entertainment industry.
This episode was originally released on September 25, 2025.

Today, we’re revisiting one of our earliest episodes with host, media personality, and creator Tefi Pessoa. Pessoa has forged a career—and amassed 2 million followers on TikTok—by being “professionally [her]self.” Her online presence is equal parts hilarious and authentic: One moment she’s doing a deep dive on celebrity relationship timelines and the next talking about her own mental health journey. On this episode, we dive into Pessoa’s financial ups and downs throughout her career, the surprising Kardashian/Jenner family member she would trade closets with, and how she sets boundaries online.
This episode was originally released in July 2024.

Lindsay Hubbard is a reality TV legend known for her 10-season tenure on Summer House and the debut season of the spin-off show, In the City. Before she was leaning into being “Lindsay from Summer House,” she was a PR executive with her own firm. On this episode, Hubbard discusses why the only thing worse than breaking someone’s heart is messing with someone’s money, the power dynamics at play in reality TV (including what it’s like filming with an ex), and her collaborative work with her stylist, Emily Men.

Micaela Erlanger is the Emmy-nominated stylist behind some of Hollywood's most talented stars, including Meryl Streep, Lupita Nyong'o, and Kelly Clarkson. On this episode, Erlanger takes us behind the scenes of all of Nyong'o 20+ looks for The Odyssey press tour and the mythological details she pulled from to create the ensembles. She also reveals her Mount Rushmore (aka her four favorite looks) from her work with Streep on the recent The Devil Wears Prada 2 tour. Plus, she shares the difference between "meta dressing" and "method dressing" in her styling. 

Jessica Knoll is the best-selling author of the novels Luckiest Girl Alive, Bright Young Women, and The Favorite Sister. On this episode, Knoll discusses how her own relationship with money and power informed the writing in her newest novel Helpless, which hit shelves on July 7. She also delves into what true success as a novelist would look like to her and how she feels in retrospect about her 2018 New York Times opinion piece "I Want to Be Rich and I'm Not Sorry."

Order Helpless here: https://www.simonandschuster.com/books/Helpless/Jessica-Knoll/9781668062302

Comedian Michelle Buteau is the star and co-creator of the hit series Survival of the Thickest, which dropped its third and final season today. On this episode, Buteau discusses not knowing if she had enough trauma to be a comedian, why she started making money as soon as she leaned into being herself, and the deliberate decision to make her main character in Survival of the Thickest a stylist. Plus, she shares everything she’s excited about for this new season of the Netflix series, including her directorial debut. 

Maria Sharapova is a five-time Grand Slam tennis champion, but after retiring from the sport in 2020, she pivoted into the world of entrepreneurship, taking on business roles for companies such as Supergoop!, Bala, and Therabody. On this episode, Sharapova shares her tips for creating a strong business pitch (hint: shorten your deck!), how she learned everything she knows about money, and details about her style evolution from the court to the boardroom. Plus, she takes us behind the scenes of her new podcast Pretty Tough, which airs weekly on Wednesdays.

Tia Williams is the best-selling author of books such as Seven Days in June and The Perfect Find, and her most recent novel, The Missed Connection, just came out on June 9. In addition to her career as an author, she also spent over 15 years as a beauty editor at magazines including Glamour, Lucky, and Essence. On this episode, Williams discusses what it was like working in print magazines during the Devil Wears Prada era, the financial decision to continue working her corporate job while writing novels, and why penning fanfic about her own life trained her to become a career author. Plus, she shares everything that went into the research process for her recent romance and detective novel. 

Laverne Cox is an actress, producer, and LGBTQ+ advocate, and as of June 9, she’s also the author of her memoir, Transcendent. In this episode, Cox discusses how her childhood love of thrifting has evolved into a vintage Mugler obsession, why it feels "divine" for her memoir to come out in this political moment, and what it was like being “broke and fabulous” in New York City before she booked Orange Is the New Black. Plus, Cox shares some of her greatest writing inspirations, including bell hooks and Walt Whitman.

Whitney Leavitt first rose to fame as a member of the TikTok group "MomTok" and as a star of the subsequent reality show, The Secret Lives of Mormon Wives. Since then, Leavitt has evolved her entertainment career time and time again, competing on Dancing With the Stars and making her Broadway debut as Roxie Hart in Chicago. Now, she's embarking on yet another new chapter in her career with her production company, Leavitt Media House. On this episode, she candidly discusses her career ambitions, why leaving Secret Lives feels different this time, and what she’s learned about style from her move from the Utah bubble to New York.