Issa Rae: From Her YouTube Era to Her Mogul Era
An article best enjoyed while sipping Viarae.
Hey honeys and hustlers,
Here’s a deep dive into one of my biggest entrepreneurial inspirations, Issa Rae. Spoiler alert - Yes, I’m a stan. There’s more omitted from this article than most people’s entire list would likely include so let’s dive in.
If you’ve been subscribed to my YouTube for a while, you may remember a video I made breaking down Issa Rae’s marketing strategy to rise from being a YouTube Creator to a cultural icon. If you missed it, I won’t hold it against you. I’ll link it below so that you can catch up. This will give you a little bit of a foundation for the next step in this discussion – how she’s using her chops as a media maven to become an entrepreneurial powerhouse.
From getting her start on YouTube, to becoming a business world superhero - Issa Rae’s rise to dominance is a huge influence on my approach to owning a media business.
Then she says badass stuff like this on the Today Show and makes us like her even more:
“I want to truly enter my mogul era, and that comes from empowering and building other moguls of color. I think that's my aspiration, and I just want to do it well. I want people and this industry in particular to take us seriously. I want to be a competitor with the best.”
Did somebody say iconic?
If you said the word “mogul” to Issa Rae when she was getting started, she likely would have laughed at you.
Yet 12 years after publishing the first YouTube episode of Awkward Black Girl, the online series she was discovered from, she’s on top of the entertainment world. And it seems like she’s only just getting started…
Let’s Look at What Issa Rae Has Accomplished
Successful Patreon (she was like their main poster child for 3 years running)
Stars in The Photograph and other blockbuster movies (IMDB)
Hosts “A Sip with Issa Rae” Podcast, exclusively on her Patreon (she has since uploading all for free on YouTube)
Launched Raedio and ColorCreative TV
Executive Producer of Black Lady Sketch Show
Executive Producer of Rap Sh!t
Transitioned Issa Rae Productions to Hoorae Media
Adds a teaching component featuring the members of her film crews sharing their roles and expertise (that was also formerly only available to Patreon members)
But it all started with the same grassroots YouTube hustle so many of us are in.
Given all her success in film, TV, music, and audio, her investment portfolio has become extensive. Yet it remains intensely focused on creative efforts and stays in alignment with her goals for empowering others.
Now THIS Is an Investment Strategy
Twitter business bros will all jump on investment advice, but Issa shows that you can make investments that truly matter. She doesn’t just invest to become an investor. She invests in her hometown, in causes she cares for, and in people she believes in.
We’ve all heard that diversification is the key to financial stability, but Issa Rae has found a way to diversify her business assets in a way that is authentic and aligned with who she is and what she values. She’s setting the standard and elevating the blueprint for what it means to create a social impact that extends beyond her creative talents and personal brand.
Hilltop Coffee + Kitchen
A coffee lover herself, Issa had always dreamt of a POC owned coffee shop in her neighborhood of Inglewood, California.
Viewing them as a communal source of productivity and collaboration, she knew the intrinsic value that a well-developed coffee shop could bring to a community of passionate people.
In 2019 she got to make that a reality when she invested in Ajay Relan and Yonnie Hago’s Hilltop Coffee + Kitchen.
Sienna Naturals
Sienna Naturals is a 100% vegan hair care brand that Issa Rae joined as cofounder with her sister-in-law, Hannah Diop.
Always advocating for authenticity, the Sienna brand leans on Issa’s personal journey with her natural hair - and the realization that there were really no high-quality plant-based options for her.
Viarae
Viarae is a new venture - a prosecco sparkling wine brand.
As the drink of choice for her character in Insecure, Viarae is meant to celebrate great times and great people as well as open the wine community up to more people.
It’s been perpetually not in stock at my local Target but I’m dead set on buying a bottle soon.
The Issa Effect
When I started my business, I had no “business plan”. There was no major goal beyond making real, steady money. I certainly didn’t have a 5-year plan – not even close.
Now that I’m coming into my own as a creator, that vision is getting clearer and my plan to achieve it has become more concrete. While developing my creative business is important, I want to keep an open mind for ways that I can invest back into my own communities and give back to the organizations, people, and places that helped me get here.
I’m currently serving on some nonprofit boards, but that’s just one way to be a part of change. My priority for social impact also means:
being intentional about hiring folks from diverse or underrepresented backgrounds
telling stories that reflect my community and culture
creating projects that give people a new perspective on a subculture they may not be familiar with
making my work accessible for people, regardless of means or location
investing in my local small business community
volunteering with nonprofit organizations, foundations, and community groups
investing your time, talent, or treasures in organizations that serve those in need, underrepresented subculture groups, and/or directly impact positive policy change
While you’re building a successful business, just ask yourself, what would Issa do?
BONUS: Listen to Issa’s acceptance speech for the 2022 Equity in Entertainment Award
Please Hustle Responsibly,
🤙🏾✨
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