When writer and actress Issa Rae created the award-winning web series The Misadventures of Awkward Black Girl in 2011, it was a true calling to walk the entrepreneur's path.

"There was just an overwhelming, almost suffocating, desire to tell a specific type of story," Rae said in a fireside chat with CBS Mornings host Nate Burleson. "For me, it came down to fatigue and frustration — 'Why isn't this storyteller doing this? Why isn't this writer telling this story?' — until it came down to the idea that I have to do it if I want to see it."

Rae decided to tell stories, one small step at a time, in pursuit of bigger ambitions like starring on the big screen and creating a television show. But betting on herself opened the door to self-doubt.

"Sometimes, these goals feel so out of reach. … Creating these little milestones and checking those off continually gave me the courage to know that I could do it," Rae said. "If I can achieve this step, then maybe I can do the next one. Breaking it down into bite-sized pieces was essential to building the courage and the bravery to go for the big thing."

In an open-hearted discussion on the first day of Black History Month, the pair of entrepreneurs shared candid stories from their experiences during the “QuickBooks + Mailchimp Fireside Chat: Issa Rae and Nate Burleson in a Conversation about Courage.” You can watch the full one-on-one by hitting play on the video below:

Rae’s strategy — one small act of courage after another — helped her find the big-time success she aspired to achieve. Today, you might know Rae from Insecure, the HBO series she created and starred in, and you've seen her on the silver screen in Little, The Lovebirds, and The Hate U Give.

Burleson, the owner of several small businesses that he started during his NFL career, brought home Rae's message.

"Oftentimes, the thing that gets in the way of the stuff we want to accomplish is our own fears," he said.

Rae and Burleson addressed head-on some of the pressures associated with running a Black-owned business. From their conversation, three key topics emerged for the audience of American and Canadian Black business owners: authenticity, introspection, and community.

Be your authentic self

As a business owner, there's a real pressure to conform to the way that others operate. Sometimes that manifests as adopting a popular marketing strategy, emulating someone else's brand, or, in Rae's case, bending her creative vision to accommodate show producers.

"I found that often I was a people-pleaser, to my own detriment. Then I started to realize that when I would see the products or the projects come out of that, there was nothing more frustrating than knowing I couldn't say something I didn't like,” Rae said. “And I can't blame anybody but myself. If I knew I didn't want this the whole time, and I didn't speak up, then who else can I get mad at but myself."

Rae has found a way to stay true to herself: writing down her priorities, practicing the conversation, then creating a dialogue to express her needs.

It's never too soon to share your authentic self, especially as a Black business owner, Burleson said.

"When it comes to starting a business, authenticity from the jump is important because it's better to have people adjust to who you truly are, than you try to adjust to what you think the needs of the people are," Burleson said. "You're the best at being you. And when it comes to your business, that's what people identify with when you talk about supporting Black business. [People will] support the most authentic version of that."

Staying authentic to your identity isn't always as easy as it sounds. Code-switching can take a social and psychological toll. Still, 68% of Black business owners say they behave differently with customers and vendors to avoid being stereotyped, according to a survey by Intuit QuickBooks.

The breadth of Burleson's professional career has spanned football stadiums, board rooms, and television studios, each with their own sets of cultural norms. As he navigated these changes, Burleson assessed his voice and brand to stay authentic to his own style.

"Unless you recognize the codes, you'll never know if you're switching or not. And unless you identify what your voice is, you will never know if you're being authentic or not. You don't even know if you're conforming, and somebody from the outside might see you and say, 'Yo, why won't you be yourself?'"

Reflect on your entrepreneurial journey

Meaningful growth is often the product of thoughtful reflection — a best practice as entrepreneurs run their businesses. Without taking the time to, say, write a business plan or assess financial statements, it's difficult to know where a business really stands.

Rae knows the value of competitive research and evaluation from personal experience. During Awkward Black Girl's scrappy start-up phase, she began doing live college tours for a fee of $100 plus room and board. It wasn't until nearly halfway through the tour that she learned other campus speakers were paid engagement fees in the thousands.

"You've always been very transparent about the ups and the downs, those ‘ah-ha’ moments where you realize, 'Damn, I'm worth more than this,' or 'My value has changed and I need to charge more,'" Burleson told Rae. "Oftentimes, when you're first starting a business, we have these issues with our own self-reflection, when we go through mistakes…But that's just part of the journey." 

Revenue is a common bump along the road for Black business owners — 55% told QuickBooks that they were denied a bank loan at least once when they started their businesses. Further, more than a quarter (28%) of Black business owners reported being turned down for a loan more than once.

Starting a business without a formal loan can feel like the deck is stacked against you. There are ways to start a business with no money and without loans, including a favorite of Rae's: good, old-fashioned bartering. It's how she got rolling on her first creative projects.

"It just came down to asking people to invest in you through the task that they needed, or the services, whatever it is, and if they wanted to contribute financially … then just making sure to deliver," she said. "And while you're asking, make sure you're giving, because that's a big thing, too. You can't just take, take, take, take, take."

The purpose of looking back, identifying mistakes and areas of opportunity, and assessing the state of your business is to apply those learnings moving forward. Your personal insights, including introspection into your personal motivations, can build forward momentum.

"I never want to ride on my last thing. I'm always thinking about 'What else can I do? What else can I accomplish?' Just because that is what drives me," Rae said. "For me, there's just a restlessness that exists and a curiosity of just what else I can accomplish."

Build up the Black community

Throughout the fireside chat, Rae and Burleson highlighted opportunities to build support, community, and culture.

"We are not paying rent in the culture. We are the culture," Burleson told attendees. "So make yourself at home, get comfortable in your space. We are in this house together."

One way Black business owners can support one another is by putting collaboration above competition Rae said. It's something she does in her own businesses, like when she opened a coffee shop in the city of Inglewood, California — at the same time that another Black woman opened a coffee shop down the block.

"I think the natural instinct would be to feel competitive," Rae said. "If anything, I felt like that just allowed more spaces for us. It was a period of joy: two Black-owned businesses, in Inglewood. … There's no reason why we couldn't support one another. … I'm not losing anything by their gain."

Camaraderie and support from within the Black community can be a huge asset, especially when 75% of Black business owners say Black businesses are judged more critically than non-Black businesses, according to the QuickBooks study. Judgment and biases can create the added pressure of working against negative stereotypes — so much so that 74% of respondents say disproving these stereotypes motivates them to succeed.

"We as Black people have a mentality that we want each other to succeed," Rae said. "I operate from that optimism and that knowledge, and so I never want to disappoint us. … We have to be the super example, and I don't take that lightly."

Rae's not alone in that sentiment. A full 70% of Black business owners told QuickBooks that they view their business' success as important for the success of future Black entrepreneurs. It's a legacy that Rae, Burleson, and the entrepreneurs in the Black community are building today for a more prosperous tomorrow.

"It's not anything I shy away from," Rae said. "I want to exceed expectations. I want to prove people wrong."

If you missed Intuit’s live Black History Month event, you can watch the full replay of the fireside chat on your own schedule.

Intuit QuickBooks commissioned online surveys, completed in December 2022, of 1,000 (500 Black and 500 non-Black) business owner respondents in Canada (adults aged 18+). There were 432 small business owners out of 500 Black respondents and 456 small business owners out of 500 non-Black respondents. The approximate average annual revenues are $71,200 for Black business owners and $83,750 for non-Black business owners. The average number of employees per business is 36 for Black business owners and 35 for non-Black business owners. Among Black business owners, 35% have 1-10 employees. Among non-Black business owners, 41% have 1-10 employees. Percentages have been rounded to the nearest decimal place so values shown in charts and graphics may not add up to 100%. Responses were collected in online surveys using Pollfish audience pools and partner networks with double opt-ins, random device engagement sampling, and post-stratification based on local census data to ensure accurate targeting and results. Respondents received remuneration.