Entrepreneurs from underrepresented groups are more likely to face an uphill climb than their white, male counterparts, but their challenges stretch well beyond systemic bias and a general lack of access to capital.
Women, transgender and Black startup founders must navigate myriad issues for which there is no playbook: People of color may question how much of their authentic selves they can bring to the workplace, CEO moms are more likely to shoulder the majority of their family’s childcare responsibilities, and many workers have never been led by someone who’s gone through gender transitioning.
In a TechCrunch Disrupt Extra Crunch Stage panel titled “The Path for Underrepresented Founders,” I spoke with Hana Mohan, a transgender woman who is the CEO and co-founder of MagicBell, a notification platform for product teams; Leslie Feinzaig, a Latina entrepreneur who started the Female Founders Alliance; and Stephen Bailey, a Black man who is the founder and CEO of Exec Online, an online leadership development platform.
We went slightly over our allotted time; the conversation was a blend of frank talk about their lived experiences and practical discussion about some of the strategies that help them keep moving forward.
Despite their varied backgrounds, each panelist agreed that it’s important for founders who aren’t from privilege or wealth to understand and accept that systemic bias is real. And because Silicon Valley touts itself as a meritocracy, the gap between expectation and reality can create cognitive dissonance.
When Feinzaig was fundraising in 2017, “I expected that it would be hard. But I also expected that it would be fair,” she said. “And in reality, it was just kind of a gaslit experience. I felt like I was in this really dark room. And nobody would tell me how to turn on the lights.”
Mohan, whose company graduated Y Combinator’s Winter 2021 cohort, said pattern-recognition bias doesn’t just influence who investors decide to work with; it also informs how founders present themselves and their companies.
“White cis men, they tend to have a bravado about how they talk, this kind of exuberant, ‘we are going to crush the competition,'” she said. “I definitely felt that when I would sprinkle my pitch with some of those words, it definitely resonated more, like you have to communicate that excitement is naturally amply balanced.”
“Very unconscious bias is obviously like that: They don’t see many people like you, which is probably changing now,” Mohan said. “I would like it to be a meritocracy, but I have started to question that it’s not as much.”
Even though he had years of business experience and had previously served as a CEO, Bailey said he felt like “there was a need for more proof points” when he pitched to investors.
“And I felt like I had a really good idea, which has been proven out over the last 10 years or so. But it felt like I wasn’t getting the same benefit of the doubt as maybe someone who might be coming in a couple years out of school with a great idea and because they’re in the right network, or someone who’s invested in them sees themselves in that person.”
Feinzaig said she and many investors in her network once advised women to “talk things up, put [on] more bravado and show that exuberance,” but she’s started to rethink that approach. “When women exhibit traditional masculine ambition traits, we come off as unlikable,” she said.
Mohan, Bailey and Feinzaig each agreed that they felt more pressure — from themselves as well as externally — to be better than white founders just to get a chance to pursue the same opportunities.
“I’m actually out there to prove a little bit more because I’m a trans person, and I’m kind of excluded that I sort of want to go anywhere anybody else can go,” Mohan said. “So at least for me, that’s a bit of a driving force.”
Bailey agreed: “My mom told me at a young age, if you want to be successful as a Black male, and in the world, you’re going to need to be better. Not just as good,” he said. “And I think that certainly plays out, in my experience, particularly in this world of venture.”
Because founders from marginalized communities often lack access to mentors and sponsors, Bailey crafted a framework to equitably distribute development opportunities. “People like to sponsor and mentor people who look like them,” he said, but even organizations that overcome this challenge still provide generic advice that doesn’t apply to their circumstances.
“A lot of the mentorship resources that others can rely on don’t apply as much to us. And so you’ve got to find your own leadership style and voice,” he advised.
Women and people of color should resist the urge to follow generic leadership and management advice, because it was not written with them in mind, said Feinzaig.
“I remember modeling the behavior of the leaders who came before me and just [being] flat-out hated,” she said. “What makes a big difference is confidence in yourself and confidence in your team. And I think I learned that the hard way, but nobody modeled it for me.”
Mohan transitioned while working at her previous startup, bootstrapping so she could focus on her mental and physical health and avoid the stress associated with accepting venture capital.
“I don’t think I would have been able to do my transition with a funded startup. I think the expectations are just so different,” she said. “I think lifestyle businesses are actually great, and people have scaled them.”
Bailey agreed, adding that underrepresented people often face unique pressure to spin up companies that satisfy investors’ preconceived notions; women are often nudged toward parenting-related services, for example.
“And when you come in and say, ‘Well, actually, I’m starting a B2B technology company,’ people say, ‘Oh, wait! I don’t expect that to come out of your mouth,'” he said. “If you allow this to define you, over time, it can really reduce your confidence. It can pull you in directions that aren’t consistent with your own sense of purpose and your own capabilities.”
Feinzaig said founders who carry the double burden of building a company while finding their way around systemic barriers should understand that confidence is something that ebbs and flows.
“It’s a thing that you walk in and out of, and I think that’s okay, just acknowledging that,” she said. “It’s not whether you’re competent or not; it’s whether you are a little bit tuned in toward feeling confident, or trending a little bit less toward it.”
