No one wants to see Black businesses succeed as much as the Black community, entrepreneur Issa Rae said during an event kicking off Black History Month.
"We have such a vested interest in our own success that nobody else has," said Rae, who's best known for creating and starring in HBO's Insecure. "It's so important to take advantage of that. Our baseline is that we want each other to succeed."
Nearly all (95%) Black business owners view their success as important for future generations of Black entrepreneurs, according to a recent survey by Intuit QuickBooks. Rae underscored the importance of using available resources — even small actions, like posting flyers in your own business — to help others in the Black business community succeed.
The writer, actress, and producer shared candidly from her own experience during “QuickBooks + Mailchimp Fireside Chat: Issa Rae and Nate Burleson in a Conversation about Courage.” Rae dropped five gems for aspiring small business owners that they can apply right away.
1. Make time for your side hustle.
Starting a business is a courageous pursuit as it can often take a while to develop the planning, resources, and self-trust to launch. Budding entrepreneurs often begin by cultivating their small business on the side of a full-time job, which can feel like a financial security blanket.
"We have those main jobs that are sustaining our living, and so much of the courage is about taking that leap to put that job behind you and to make your passion for your business your full-time focus," Rae said.
It can take time to develop that courage, Rae added, so entrepreneurs should give themselves grace as they develop their business plans. But she advised holding yourself accountable to working on your own business alongside your day job.
"Carve out those little moments to be able to say, 'Okay, I have my 9-to-5, but from 6 to at least 7, I'm going to make this happen,'" Rae said. "And then eventually those hours will widen, until you're able to say, 'Bye, job, I'm going to make this my full-time.'"
2. When you ask for something, always give back.
Like many Black small business owners, Rae had a tough time getting funding through traditional financial institutions.
"I was denied loans all the time. I also had a lot of credit card debt, which I don't advise," she said.
Over 55% of Black-owned businesses in Canada and the U.S. have been denied a loan at least once, according to the QuickBooks survey. When Rae needed funds for her first productions, she didn't give up — she got creative.
"It just came down to asking people to invest in you through the task that they needed, the services," she said. "The first step is obviously doing the work and showing people that you're serious, and people will support [you]."
Rae turned to old-school bartering to get what she needed. A friend's dad wanted someone to film school talent shows, which she did in return for time to use the camera herself. She sought out others who would pay her a hundred bucks for small tasks, which she earmarked as funds for her own productions. For Rae, the key was always giving back to those providing her with funds or resources.
"While you're asking, make sure you're giving, because that's a big thing, too. Like, you can't just take, take, take, take, take," she said.
3. Co-create the future with your team.
When small business owners are struggling to get the loans and funding streams they need, it can make hiring a challenge. This is another situation where Rae suggests getting creative to find value to offer potential employees.
"A lot of my conversations have been like, 'Look, I don't have the money to pay you right now, or I only have this much, but as soon as we get to this milestone, I got you,'" she said. "I've always made good."
This kind of approach has the additional benefit of getting your employees invested in the success and future of your venture. Ideally, they're getting something they want out of the deal, too.
"It goes back to making sure that the people that you're working with can see their future in your vision and to also trust that you're going to help them get there," she said.
Rae's biggest challenge as an entrepreneur has been learning to be a great team leader. She says it has been a work in progress as she's built out a team, made mistakes, and applied the lessons she learned moving forward.
"You can be so focused on what your mission is that you can forget that there are other people who have missions of their own and to make sure that you're nurturing that as a leader," Rae said. "My biggest challenge has been curating the right team, but it's also been my biggest blessing."
Rae suggests frequent check-ins with staff: Are they set up with what they need? How's their family? Are you both still aligned on their goals and growth? She said she learned the hard way that having those conversations can save a lot of heartache later on.
4. Break big goals into small steps.
Being a small business owner doesn't mean that you aren't dreaming big. Even as Rae created her web series The Misadventures of Awkward Black Girl in 2011, she was dreaming of a life writing for television and starring on the big screen (things that she's since checked off her list). But the path from here to there can feel impossibly daunting.
"Sometimes, these goals feel so out of reach," Rae said.
Instead of letting fear and self-doubt take over, Rae created a series of achievable steps that built her confidence.
"Creating these little milestones and checking those off continually gave me the courage to know that I could do it. If I can achieve this step, then maybe I can do the next one," she said. "Breaking it down into bite-sized pieces was essential to building the courage and the bravery to go for the big thing."
5. Pursue your passion.
Every small business owner's journey looks a little different, and they might have different sources of motivation that fuel the drive to succeed. What has fueled Rae's creative entrepreneurial pursuits is passion — an "overwhelming, almost suffocating, desire to tell a specific type of story” — and she suggests aspiring entrepreneurs find that passion for themselves.
"You have to be willing to make that sacrifice and have that passion for what you do because it is going to consume your life," she said.
The drive to share her work with the world has taken a toll on Rae. There was the year she said "yes" to too many things. She followed it with "a year of no" to try to find balance. When she realized that she was working every single day, she created a mandatory day of rest and procrastination each week. But for Rae, the stress is worth the reward.
"Despite the stresses that I have on a day-to-day basis, I'll still talk about it with a smile. It is still the only thing I would rather be doing," Rae said. "If you don't feel that way about your business, then maybe reconsider. But if you do, just know that it will be worthwhile in the end."
If you missed Intuit's live Black History Month event, you can watch the full replay of the fireside chat on your own schedule.
