Gender Bias in VC with Charlie O’Donnell
A few months ago, venture capitalist–turned-fundraising consultant Charlie O’Donnell and I had a disagreement about gender bias on LinkedIn.
After a bit of back and forth, Charlie invited me to take the argument to a recorded video discussion.
Which quickly transformed into a LIVE recorded discussion in a cafe around the corner.
(Because we're actually IRL friends and neighbors)
Charlie released the video last week (you can watch it on YouTube).
And upon reviewing it, I have multiple thoughts:
1) I’m so glad we did this.
The bias against women in VC fundraising is a widely-known phenomenon that we often turn a blind eye towards.
And honestly, I think that might be because the statistics are so stark and stubborn that it almost feels like there’s nothing more to say.
But there is ALWAYS more to say, so long as women still struggle to raise capital despite being statistically strong performers as founders.
2) Charlie and I shared valuable tips with each other from our unique advisor experiences.
Because of this conversation, I will tweak how I advise clients who face bias. And I think Charlie will do the same.
Charlie raised this phenomenal point: in fundraising pitches, women tend to be asked more risk-focused questions (ie. why their startup won’t work) and men are asked more opportunity-focused questions. And unfortunately, being asked more risk-focused questions is associated with a lower chance of investment.
Because this is true, it’s important to coach founders who get too many risk questions on conversational “judo moves” that pivot the room away from only talking about risks, and focusing instead on the opportunity.
For Charlie, I hope our discussion encouraged him to get invested in more deeply understanding the biases founders will face when they walk into the room. He previously argued that it’s most important for founders not to waste time obsessing about bias. But our conversation encouraged him to take on the responsibility as an advisor to obsess about it for them; to understand it well enough as to guide founders toward clever ways to counteract it.
3) And yet, I still find myself unsatisfied, like I didn’t do enough in this discussion.
This topic represents a HUGE problem that many folks have dedicated their entire careers to fixing. And it's a great privilege to get to sit down with an influential VC who is willing to listen and learn.
Given that context, I watch this interview brimming with wishes on what I could have done better.
First: We went straight into nuance and actions before acknowledging the reality.
In our LinkedIn argument, it was initially argued that the gender gap in VC fundraising isn’t as bleak as we think. But it is.
According to PitchBook / NVCA’s Venture Monitor, in 2025 less than 1% of VC investment went to all-female founding teams, and only 20.5% of deals are going to teams with at least 1 woman founder.
Both percentages are the lowest they've been since 2015.
I also regret that we didn’t spend more time talking about intersectionality. According to Crunchbase, only around 0.4% of U.S. startup funding went to companies with a Black founder or co-founder in 2024; a multiyear low. And the numbers get even more stark at the intersection of gender and race, in particular for Black women and Latina founders.
Finally, the focus of the discussion: We talked about our methods for helping founders, but failed to talk about who holds the real responsibility here: Investors.
Recent studies suggest women-founded companies are more capital efficient investments (higher ROI) than all-male teams. If that’s true, then overlooking women founders isn’t just inequitable; it's illogical.
As thought leaders in this space, it’s important to focus at least as much time on holding investors and LPs accountable for how they make investment decisions as we do on guiding women founders on how to fundraise.
I also wish I'd pushed back more on the portrayal of women fundraisers, especially our reflections on them "falling into stereotypes."
Venture capital runs heavily on pattern recognition. And historically, the pattern of a “venture-backable founder” has looked a lot like a man confidently pitching massive upside.
But if the data tells us that the presence of women founders makes a company more likely to succeed, why the heck should a woman ever have to worry about that?
Instead of teaching women how to pitch like men, shouldn’t VCs update the pattern to match the founders who actually perform best?
Because telling shrewd women business owners to avoid the details, focus on the opportunity, not lean into their "stereotypes",
It might work,
...But it also feels like telling a girl to shrink herself to attract a boyfriend.
And at the same time, I acknowledge that my feeling aghast about needing to code-switch in these moments comes from a place of privilege.
Here’s where I landed after watching the video back:
I think we made some progress in having the discussion and talking about adaptation,
And I think we surfaced some tips and perspectives that might help founders and advisors.
But this conversation isn't done.
We need to hold a mirror up to investors.
Because that's where change really needs to happen.
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