

I was raised in the south, where forgetting to address your elder as "ma'am" or "sir" is a mortal sin, and "please" and "thank you" are sprinkled at the end of sentences like salt and pepper. But as I get older, I've learned that manners and money don't always mix, and in a recent interview with The Hollywood Reporter, Issa Rae explained how she learned this firsthand.
The Insecure creator explained that although she may have been naive when she entered the business, she now is completely aware of her worth and her personal obligation to add tax. She explained:
"I've definitely demanded. Yvonne joked before the Emmy nominations came out, 'Girl, I told all my agents, 'Don't make no deals until after Tuesday or Monday,' whenever the announcements were, 'because our price is going up or down.' So there is something to that, too, of just realizing your worth."
"Also, seeing how little these white people care about asking for more than they're worth in many cases.You can't be polite or tiptoe, or be modest about those things. You're seeing these nine-, 10-figure deals out there. I have a great team that also is not afraid to ask for beyond my worth. I have an amazing Black lawyer who is constantly being like, 'No, I'm going to get you better.' Or, 'No, I'm going to make sure. I heard that so-and-so made this, you're about to make this.'"
For more gems from Issa on how to align your business mind and get your business mind all the way together, scroll below!
On Managing Self-Doubt:
Successful creatives aren't immune to self-doubt and Issa Rae says that this is big facts. In the interview, Issa broke down how her insecurity and negative self-talk almost blocked her bag:
"[With] 'Insecure', it took so long and every draft was like, 'No, this isn't it. No, this isn't it. No, this isn't it.' I was just like, 'Oh, OK. Maybe this is the end of the road for me,' especially when I'm investing in this big venture, which ended up being ColorCreative, and spent all my money and didn't have anything. I remember being on the set of a pilot we were filming ['Words with Girls'] and getting the call that HBO was not feeling the latest draft and I was losing Larry [Wilmore, 'Insecure''s first showrunner]. I was like, 'This isn't going to happen for me, and I just did all of this for nothing.'"
"Thankfully, Larry leaving for The Nightly Show, as much as I love him, was the best thing that could've happened because it forced me to be like, 'OK. It's not a workplace comedy,' and having a conversation with HBO was really helpful just in terms of centering it. It was just like, 'I'm going to put everything that I'm going through out on the table in this pilot. If they say no, at least I tried, and fuck it.'"
On Accepting Constructing Criticism:
"I'm open to all criticism. I feel like you have to be, to be in this industry. There are Black critics that I value what they think because I read what they read, or I read what they write about everything. I love it. I can see this point of view, and that's so interesting. It may be reflected in something else that I do down the line, or it may spark inspiration for conversations that we may have. We feed each other in that really interesting way."
"But let's be real. There are a couple where I'm like, 'Oh, this person just comes for me,' or 'This person doesn't like me.' You're putting your personal life into it. You're a blogger, not a critic at this point. It's an art form."
On Keeping Business & Personal Life Personal:
Last year, it was announced that Issa and her longtime boyfriend, businessman Louis Diame were engaged to be married and had us shook. Issa, who is normally tight-lipped when it comes to her personal life, said that we can expect it to stay that way––because it's none of our damn business.
"I guess because it's private. Whose business is it? I realized I just don't like to be the subject of conversations if it doesn't have to do with my work. I've always been like that, where I'd be dating someone and my friends would find out six months later. Like, 'B*tch, what the f*ck? Why don't we know this?' So it's just always been that I want to vet situations for myself. I really value that part of my life a lot."
To read Issa's full interview, click here!
Featured image by Getty Images.
Taylor "Pretty" Honore is a spiritually centered and equally provocative rapper from Baton Rouge, Louisiana with a love for people and storytelling. You can probably find me planting herbs in your local community garden, blasting "Back That Thang Up" from my mini speaker. Let's get to know each other: @prettyhonore.
'He Said, She Said': Love Stories Put To The Test At A Weekend For Love
At the A Weekend For Love retreat, we sat down with four couples to explore their love stories in a playful but revealing way with #HeSaidSheSaid. From first encounters to life-changing moments, we tested their memories to see if their versions of events aligned—because, as they say, every story has three sides: his, hers, and the truth.
Do these couples remember their love stories the same way? Press play to find out.
Episode 1: Indira & Desmond – Love Across the Miles
They say distance makes the heart grow fonder, but for Indira & Desmond, love made it stronger. Every mile apart deepened their bond, reinforcing the unshakable foundation of their relationship. From their first "I love you" to the moment they knew they had found home in each other, their journey is a beautiful testament to the endurance of true love.
Episode 2: Jay & Tia – A Love Story Straight Out of a Rom-Com
If Hollywood is looking for its next Black love story, they need to take notes from Jay & Tia. Their journey—from an awkward first date to navigating careers, parenthood, and personal growth—proves that love is not just about romance but also resilience. Their story is full of laughter, challenges, and, most importantly, a love that stands the test of time.
Episode 3: Larencia & Mykel – Through the Highs and Lows
A date night with police helicopters overhead? Now that’s a story! Larencia & Mykel have faced unexpected surprises, major life changes, and 14 years of choosing each other every single day. But after all this time, do they actually remember things the same way? Their episode is sure to bring some eye-opening revelations and a lot of laughs.
Episode 4: Soy & Osei – A Love Aligned in Purpose
From a chance meeting at the front door to 15 years of unwavering love, faith, and growth, Soy & Osei prove that when two souls are aligned in love and purpose, nothing can shake their foundation. Their journey is a powerful reminder that true love is built on mutual support, shared values, and a deep connection that only strengthens with time.
Each of these couples has a unique and inspiring story to tell, but do their memories match up? Watch #HeSaidSheSaid to find out!
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Love Is The Muse: How Skylar And Temi Built A Creative Life Together
When Temitope Ibisanmi DM’d the word “muse” to Skylar Marshai, he knew he was shooting his romantic shot. He didn’t realize, however, that he was connecting with his future business and creative partner, too.
“I was the boyfriend,” Temi says. “Everybody out there knows, you’re the cameraman at that point.”
Skylar sees things differently. At the time, she was shooting content on her iPhone. Temi came into the picture with a new perspective, an understanding of tech, and, eventually, a camera. “He doesn't give himself enough credit,” Skylar says. “He wasn't just my tripod. He wasn't just standing behind the camera and going ‘click.’ He was giving advice. He was giving me insight to how I could look at things from a different perspective. And I was like, 'Oh, he’s an artist.' I think it was maybe a heartbeat of that kind of energy of like, ‘Baby, can you take this picture?’ And it turned so quickly into, we're partners. We can work together in a way where we're advancing each other's creative thinking.”
The pair often says they’re two sides of the same coin. Skylar is an Aquarius. She attended art school, paints, and loves poetry. She’s more than happy to let the couple’s management firm and agency, Kensington Grey, handle their admin work. And, she loves to sleep in. Temi, on the other hand, wakes up early. He’s a Virgo. He loves a to-do list and regularly checks in on the couple’s brand partnerships spreadsheet to make sure everything is on track.
Because his storytelling was steeped in his love of technology, he didn’t always think of himself as a creative person. “Where I [am] the dreamer who wants to pluck things out of the sky and spend all day with my head in the clouds, Temi [is] so good at grounding me and helping me figure out how to make things make sense on paper. We just work together in such a complimentary way,” Skylar says.
It’s been more than six years since Brooklyn-based couple Temi and Skylar started dating, and nearly four since they cemented their working relationship. On TikTok and Instagram, the couple’s travel, fashion, and home content regularly rack up hundreds of thousands of views. They’ve worked with brands such as Coach, Aesop, Away, and Liquid IV, bringing their vibrant perspectives to every campaign they execute. Still, nearly two years since both Temi and Skylar committed to full-time content creation and creative directing, the couple says their romantic connection remains their priority.
“We told each other we would much rather go back to full-time jobs and preserve our relationship than to be full-time freelancers, barely getting a night's rest [and] barely kissing each other because we're so busy shooting,” Skylar says.
Working from home can make it hard to separate work from personal life for any entrepreneur. It can be even more challenging when your business partner is also your lover. Temi and Skylar had already used couples therapy as a tool to help them effectively communicate with one another. When they ran into challenges while working together, their therapist helped them set physical boundaries to help combat the issues.
"We told each other we would much rather go back to full-time jobs and preserve our relationship than to be full-time freelancers, barely getting a night's rest [and] barely kissing each other because we're so busy shooting."
“It actually took us doing very specific physical things to create boundaries between work and play in our relationship,” Skylar says. “So, for instance, we will only have conversations about work when we're out of bed or we're at the table or in the office. Initially, when we started, we had to light a candle to say that, 'Okay, this is a space where we're connecting, we’re not talking about work.' We needed really hard boundaries at the top. And then it became a little bit more organic.”
The boundaries have been crucial to implement, especially because the couple began working together so naturally. When the pair first met, Skylar was NY-based a social strategist for BuzzFeed and was using content creation to drive business to her lingerie company. She was shooting her own content. Temi was working for Microsoft in D.C. He’d recently traded in his DJing equipment for a camera. “I've always loved taking pictures,” he says. “Even when I was a kid, my African mother would wake me up at 3:00 a.m. [during a] party, and be like, 'Come take the family picture.'”
Growing up, Temi says he watched his parents support each other and be the true definition of partners. He knew he wanted the same for his own relationship. But, the couple also wanted to make sure they were being financially responsible. The pair didn’t quit their traditional jobs until they’d saved up two years' worth of their cost of living. And, Temi received his Master of Business Administration from New York University with the knowledge that it could either help him advance in his corporate career or be applicable to his business with Skylar.
Today, they say their working relationship is more of a “quiet dance.” They still implement some of the boundaries they learned in therapy, but they also lean into their natural strengths and deep love for one another. When we speak, Temi has planned a date for the couple to see Princess Mononoke in 4K IMAX and added it to their Notion so they can factor it into their busy schedules. “I fully plan to date for the rest of my life,” he says.
Skylar says the couple doesn’t just wait for date nights to check in with one another, though. This often happens in the mornings, after Temi has made her peppermint tea and poured himself a cup of coffee. When they ask each other how they slept, she says, it’s not just a “nicety.” It’s a genuine question meant to foster connection.
“A lot of it happens during the day in the midst of work. We'll stop and we'll hug. Or we’ll slow dance in the kitchen,” she says. “Sometimes it's hard to set a whole date night when you have 7,000 things going on. So, we must grasp these moments and check in when we can. And I think it's become so organic to us that I actually didn't even realize how often we do it. But all day long, we're like, 'Are you good? I felt like your energy shifted,' because we're best friends, we just know. We just feel it happen.”
What’s better than being in love? Building wealth while doing it. Watch Making Cents here for real stories of couples who make money moves together.
Featured image by Cj Hart @hartbreak