“When will you hire a man?”—Yes, they really asked that. These moments go beyond awkward; they spotlight just how often women are still underestimated, overlooked, or outright dismissed in the investment world.
For women founders, fundraising often comes with a side of disbelief. The best ideas can be met with the worst questions—ones that reveal the quiet biases still embedded in startup culture. But as these founders show, bias doesn’t stand a chance against sharp comebacks, proven results, and an unshakable belief in their vision.
In honour of Women’s Day, we asked female founders to share the most outrageous (or insightful) investor questions they’ve faced—and how they answered back.
Trish Mackie-Smith, CEO and Co-founder of inndox
“During early fundraising, I was called an ‘agitator’ by a male venture capitalist who questioned why he should invest in me. To change his perception, I had to soften my language about reforming the real estate industry and instead, focus on how my innovation solved a problem.”
Thuy Pham, Spectrum Digital AI
“Since I haven’t pitched to investors yet, I haven’t personally been asked this. But from what I’ve seen, a common frustrating one is: ‘Who’s the technical person behind this?’ I already know my answer: ‘I am.’ I designed and built the system that will transform how businesses automate operations, and now we’re launching to bring this to market.”
Dr Louise Metcalf, Founder & CEO of Gheorg
“One appalling question I’ve encountered was, ‘When will you hire a man to run the company?’ This highlights the pervasive stereotype that only men are suited for business leadership – a notion as outdated as it is inaccurate.”
Jo Agresta, CEO & Co-Founder of Abodey AI
“One of the worst investor questions I’ve received as a female founder was: ‘Do you think your emotions will cloud your rational decision-making?’ My response? ‘Emotion fuels empathy, which drives innovation. That’s my edge.’”
Ludwina Dautovic, Founder, CEO of The Room Xchange
“When I was pitching 8 years ago, I was twice asked, ‘How is your husband involved?’ The first time, I was taken aback but forgave the gentleman as he was elderly, and I attributed it to a generational gap. However, the second time it came from a man in his 40s, and it truly troubled me. I responded by turning the question back on him: ‘How is your wife involved in your business?’”
Pascale Helyar-Moray, Executive Director, Strategy, Innovation & Marketing
“So…I assume that because you’re trying to solve for women retiring into poverty, this is a not-for-profit company?”
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