Overcoming Bias & Building Confidence: Insights from 3 Founders

The Unique Challenges Faced by Underrepresented Entrepreneurs

Individuals launching businesses from underrepresented demographics frequently encounter greater obstacles compared to their white, male counterparts. These difficulties extend beyond systemic prejudice and limited access to funding.

Navigating Uncharted Territory

Founders who are women, transgender, or people of color must address a multitude of complex issues for which established solutions are often absent. People of color may grapple with determining the extent to which they can express their authentic selves in professional settings.

CEO mothers are statistically more likely to bear the primary responsibility for their families’ childcare needs. Furthermore, many employees may lack experience being guided by leaders who have undergone gender transition.

Insights from a TechCrunch Disrupt Panel

During a TechCrunch Disrupt Extra Crunch Stage panel discussion, titled “The Path for Underrepresented Founders,” I engaged with Hana Mohan, a transgender woman and CEO/co-founder of MagicBell, a notification platform for product teams.

Also participating were Leslie Feinzaig, a Latina entrepreneur and founder of the Female Founders Alliance, and Stephen Bailey, a Black man who serves as founder and CEO of Exec Online, an online leadership development platform.

The conversation, extending slightly beyond the scheduled time, blended candid accounts of personal experiences with pragmatic strategies for continued progress.

Acknowledging Systemic Bias

Despite their diverse backgrounds, all panelists concurred on the importance of acknowledging and accepting the reality of systemic bias for founders who do not benefit from privilege or wealth. Silicon Valley’s self-proclaimed meritocracy can create a disconnect between expectation and lived experience, leading to cognitive dissonance.

Feinzaig shared that during fundraising in 2017, she anticipated difficulty, but also expected fairness. “In reality, it felt like a deceptive experience,” she stated. “I felt lost in the dark, with no guidance on how to find illumination.”

Pattern Recognition and Presentation

Mohan, whose company was a graduate of Y Combinator’s Winter 2021 cohort, explained that pattern-recognition bias influences not only investor decisions but also how founders present themselves and their ventures.

“White cisgender men often exhibit a confident, assertive demeanor, proclaiming their intent to dominate the competition,” she observed. “I discovered that incorporating similar language into my pitch increased its resonance, suggesting a need to convey that level of enthusiasm.”

Mohan acknowledged the presence of unconscious bias, noting that the landscape is evolving. “I would prefer a true meritocracy, but I’ve begun to question whether that ideal fully exists.”

The Need for Additional Proof

Bailey, despite possessing extensive business experience and prior CEO experience, felt compelled to provide “more proof points” when seeking investment.

“I believed in my idea, which has proven successful over the past decade,” he explained. “However, I sensed I wasn’t afforded the same benefit of the doubt as someone recently graduated with a promising concept, or backed by a supportive network.”

Rethinking Traditional Advice

Feinzaig mentioned that she and her network previously advised women to “project more confidence and exuberance,” but she is now reconsidering this approach. “When women display traditionally masculine ambition, they are often perceived as unlikeable,” she noted.

The Pressure to Excel

Mohan, Bailey, and Feinzaig all expressed feeling increased pressure—both self-imposed and external—to outperform white founders simply to gain equal opportunities.

“As a trans person, I feel a need to prove myself further, to access the same possibilities as others,” Mohan stated. “This drive motivates me to push boundaries.”

Bailey echoed this sentiment, recalling his mother’s advice that Black men must strive to be “better, not just as good” to achieve success. “This dynamic certainly plays out in the venture capital world, in my experience.”

Developing Equitable Opportunities

Recognizing the lack of access to mentors and sponsors within marginalized communities, Bailey developed a framework for equitable distribution of development opportunities. “People tend to sponsor and mentor those who resemble them,” he said, adding that even organizations addressing this issue often offer generic advice that doesn’t apply to unique circumstances.

“Many readily available mentorship resources are less relevant to our experiences. Therefore, it’s crucial to cultivate your own leadership style and voice,” he advised.

Rejecting Generic Leadership Models

Feinzaig emphasized that women and people of color should resist adopting generic leadership and management advice, as it was not designed with their experiences in mind.

“I once attempted to emulate the behaviors of previous leaders and faced significant resistance,” she recalled. “Confidence in yourself and your team is paramount. I learned this through trial and error, as no one modeled it for me.”

Prioritizing Well-being

Mohan transitioned while working at a previous startup, choosing to bootstrap to prioritize her mental and physical health and avoid the pressures of venture capital funding.

“I don’t believe I could have navigated my transition with a funded startup. The expectations are simply too demanding,” she said. “Lifestyle businesses can be a viable and fulfilling option.”

Challenging Preconceived Notions

Bailey agreed, adding that underrepresented individuals often face pressure to launch companies that align with investors’ preconceived notions. “Women are frequently steered toward parenting-related services, for example.”

“When you present a B2B technology company, you may encounter surprise. Allowing these expectations to define you can erode your confidence and lead you down paths that don’t align with your purpose and capabilities.”

Embracing Fluctuating Confidence

Feinzaig concluded that founders navigating systemic barriers should recognize that confidence is not a constant state.

“It’s something you experience in waves, and that’s perfectly acceptable,” she said. “It’s not about your competence; it’s about your level of confidence at any given moment.”