
Raise A Glass To Issa Rae: Prosecco, Profit, And The Power Of Diversified Success

Issa Rae is the blueprint.
As if the multi-hyphenate media mogul couldn’t add any more credentials to her already extensive resume, the Insecure creator has now entered the spirits industry with her new Prosecco line in partnership with E. & J. Gallo Winery, Viarae.
For years, this bubbly Italian wine has maintained a supporting role in the storyline within Rae’s universe. From being the drink of choice for the show’s lead character of Insecure, Issa Dee, to making special appearances during her A Sip series, it’s safe to say that you can’t indulge in Prosecco without thinking of Issa Rae.
Issa Rae, creator and founder, Viarae Prosecco
Courtesy of Viarae
In her October cover story interview withLos Angeles Magazine, Rae shared her hopes to take the stuffiness out of wine drinking and create a brand that makes luxury more approachable. "[Prosecco] just felt not as stuffy as Champagne, which I couldn't afford at the time. And it just felt approachably luxurious, which is how I like to think I live my life."
The Barbie star understands the power of her congeniality, which contributes to the success of her many endeavors. Fans and customers alike know that whether they’re tuning into her shows or picking up her Prosecco, they’re buying into the Issa Rae brand and community-driven pursuits, and truth be told, she can take all our coins.
Her Viarae Prosecco partnership is just one of the many entrepreneurial endeavors that Rae has launched on the tail of her meteoric rise.
The 38-year-old entrepreneur is one of the partners at Hilltop Coffee + Kitchen, a chain originally rooted in the heart of South Los Angeles, is the owner of the production company Hoorae, along with her record label, Raedio, has starred in hit films like Barbie and Spider-Man: Across the Spider-Verse, and recently been named as the creative director for the 2024 American Black Film Festival — just to name a few.
During an interview with Billboard, the writer shared that her secret is all about having multiple streams of income. “I always say that I model myself after Diddy, Ellen [DeGeneres], and Oprah: Oprah for being able to diversify her businesses and being a major influencer in that way; Ellen for being able to make a business out of being herself; and Diddy for his business acumen in expanding beyond hip-hop. I’ve looked to them in terms of ways to make my own imprint,” Rae told the publication.
Being entrepreneurial and scrappy is a personal acumen that Rae accredits the internet for. “It comes from being on the internet. When I just wanted to put out some s**t that I had written, and then being forced to market it and then build a team around it and then having ideas about promoting it.”
"I always say that I model myself after Diddy, Ellen, and Oprah: Oprah for being able to diversify her businesses and being a major influencer in that way; Ellen for being able to make a business out of being herself; and Diddy for his business acumen in expanding beyond hip-hop. I’ve looked to them in terms of ways to make my own imprint."
Viarae Prosecco, a bright, crisp, lively, and refreshingly refined take on the classic Italian sparkling wine.
Courtesy of Viarae
In a 2020 Bustle interview with author and journalist Elaine Welteroth, Rae was clear that while she has achieved a great deal of success in her career, she was only just beginning. “Every single time you do something, there’s a moving goalpost. I still feel like I have so much more to do and so much more to prove,” she said. “To the point of competing, I guess, with myself or with some invisible being just ahead of me, I don’t feel any impact yet. And a lot of that comes with time. Yes, 2007 was 13 years ago, but [it] feels like it’s been two years. I’m like, 'I need more time.'”
Watching Rae soar as a serial entrepreneur, it’s evident that it’s Issa vs. Issa, and the bar just keeps rising — it makes you wonder what can’t she do and what will she do next, all at the same time.
In her October interview with WineEnthusiast, she shared her plans for the future, “I think if people f*ck with this, then absolutely, I would love to expand!” she said. In Issa’s world, lifestyle is king, and her mission is clear. “I want to tell stories around that lifestyle.”
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Featured image by Arturo Holmes/Getty Images
- Issa Rae Is #TeamLeaveThatJob To Pursue Your Passion ›
- Issa Rae Says Procrastinating Makes Her Work Harder & I Can Totally Relate ›
- Cover Story: Issa Rae Comes Full Circle ›
- 10 Inspirational Issa Rae Quotes For When You Need Them Most ›
- Issa Rae Wants You To Know Manners & Money Don't Always Mix ›
- Issa Rae On Having Multiple Streams Of Income: 'Because, Why The F*ck Not?' ›
Aley Arion is a writer and digital storyteller from the South, currently living in sunny Los Angeles. Her site, yagirlaley.com, serves as a digital diary to document personal essays, cultural commentary, and her insights into the Black Millennial experience. Follow her at @yagirlaley on all platforms!
'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