Driving the Dialogue: Questions These Female Founders Wish You Asked
Women represent 50.5% of the U.S. population, but in 2022, companies with solely female founders garnered just 2% of the total capital invested in venture-backed startups. The share of funding for companies co-founded by women? That ticked up to 15.4% last year, which still leaves a massive delta. The long and short of it: Female founders face systemic barriers to founding, funding, and scaling their businesses.
This year’s International Women’s Day theme is “Embrace Equity” — a call to imagine a world free of bias, stereotypes, and discrimination. We believe part of working toward a more level entrepreneurial playing field (in addition to funding more women-led startups) is allowing founders to establish their own narratives rather than having tropes thrust upon them.
Why? Because steering one’s story is a critical aspect of the entrepreneurial journey — one that has proven to be pivotal for fundraising and outcomes. Accordingly, we checked in with a shortlist of entrepreneurs across our portfolio about the dialogues they want to drive as women scaling startups. Here’s what they had to say.
“One of the ways we can start evolving the conversation is by asking founders questions centered around the business itself…As a leader, I welcome questions on our business, growth metrics, and strategy.”
The Founder: Shivani Siroya
The Company She Built: Tala, the Santa Monica-headquartered company offering digital financial services to help the traditionally underbanked across the globe borrow, save, and grow their money.
The Questions Shivani Wishes She Were Asked Less: “I truly value the increasing spotlight on female founders and women leaders over the past decade, especially in the tech industry; it’s bringing more attention to the fact we have so much work to do to create a more equitable society. But I also wonder if the very bucket we get placed in is what sets us back. Being a ‘female founder’ is somewhat unique in the industry I work in; and while that can be an advantage sometimes, I do question whether dividing the world into ‘female founders’ and ‘founders’ ultimately moves the needle on creating a more equitable landscape.”
The Questions She Wishes She Were Asked More: “One of the ways we can start evolving the conversation is by asking founders questions centered around the business itself, rather than women-leaning questions such as managing work-life balance, personal life, and being a working mother. As a leader, I welcome questions on our business, growth metrics, and strategy.”
“Women have the ability to world-build, and those are the conversations I try to have with investors.”
The Founder: Helen Adeosun
The Company She Built: CareAcademy, the Boston-based healthcare training platform transforming the way we support and upskill essential caregivers.
The Questions Helen Wishes She Were Asked Less: “Research has shown that female founders and male founders get asked drastically different questions by VCs. While male founders get asked questions about the potential opportunities for their companies, female founders are asked questions about risks and potential losses — how you will defend your position versus how you will grow in the market. This data holds true to my experience. We’re put on defense, and I have had to turn those questions around to talk about the opportunity for growth. The line of questioning shows they’re only thinking about how I’m different from the typical founder they’ve worked with and can’t envision what success looks like.”
The Questions She Wishes She Were Asked More: “Women have the ability to world-build, and those are the conversations I try to have with investors.”
“I always like to say, if you want equality in the workplace, you have to have equality at home.”
The Founder: Kristin Langenfeld
The Company She Built: GoodBuy Gear, the Denver-based recommerce marketplace saving parents time, space, and money by enabling the reuse of quality-ensured baby and kids gear that would otherwise end up in landfills.
The Questions Kristin Wishes She Were Asked Less: “The age-old question ‘can you really do it all?’ because the truth is, whether you’re female or male, you can never do it all — especially when it comes to building a business. You need help, and that’s not a weakness or reflection of your gender. Being a mom is a superpower, and it makes you ruthlessly prioritize. So the answer is NO, you can’t do it all, but that’s not a bad thing.”
The Questions She Wishes She Were Asked More: “Surprisingly, the question I wish all parent founders were asked more (and not just moms) is ‘how do you manage to balance everything with kids?’ The answer for everyone should include the other partner or support caregiver. In my household, we re-prioritize family and work constantly. We build and rebuild support systems and work together weekly to determine who is parenting so that the kids can come above any of our business priorities. I always like to say, if you want equality in the workplace, you have to have equality at home.”
“I want more product-related questions about what we’re building.”
The Founder: Deborah Gladney
The Company She Built: WorkTorch, the Wichita-based career empowerment platform fueling service industry professionals and businesses with the resources and tools needed for long-term employee stability, growth, and success.
The Questions Deborah Wishes She Were Asked Less: “‘How can I be helpful?’ People have good intentions with this question, but we’re asked this all of the time, and it puts the onus back on us.”
The Questions She Wishes She Were Asked More: “I want more product-related questions about what we’re building, like, ‘How does WorkTorch help people? How does it work? Why is it needed?’”
“I wish more people asked about the role models that have influenced my leadership style and approach.”
The Founder: Christie Hovarth
The Company She Built: Wagmo, the Brooklyn-based tech-first wellness company empowering pet parents to get the care their pets need while alleviating the financial stress of routine and emergency services.
The Questions Christie Wishes She Were Asked Less: “What’s it like being a female founder? What do you think is the biggest challenge facing women in business today? Do you think it’s harder for women to secure funding for their businesses? What are you wearing?”
The Questions She Wishes She Were Asked More: “What do your female candidates bring to the table that ultimately make them best suited for their roles? How do you prioritize diversity within your company, and what steps have you taken to create an inclusive workplace culture? What role models or mentors have influenced your leadership style and approach?”
“I wish VCs would just ask the questions — no matter how blunt, harsh, or direct they may be…If we’re not willing to challenge female founders, then these women will never get a chance to actually make their case.”
The Founder: Haley Rosen
The Company She Built: Just Women’s Sports, the Los Angeles-based digital-first consumer media brand dedicated to 100% women’s sports, 100% of the time.
The Questions Haley Wishes She Were Asked Less: “‘Why do only 2% of VC dollars go to women?’ I’m asked this constantly and have primarily seen this question directed at female founders. This is a completely valid question that I think we need to answer, but I feel it would be far more productive to ask investors (who are responsible for making those decisions) instead of founders.”
The Questions She Wishes She Were Asked More: “I wish VCs would just ask the questions — no matter how blunt, harsh, or direct they may be. I’ve found that people can sometimes sugarcoat their feedback when it comes to female founders, because they worry they might come across as too harsh or direct. But if we’re not willing to challenge female founders, then these women will never get a chance to actually make their case.”
