The Most Obvious Bet Nobody's Making
Women make up 15% of tech founders globally1, yet all-female founding teams receive only about 2% of venture capital funding (and that’s been the average for 30 years!)2. If you have a male co-founder, your chances of getting funded go up by a staggering 1054%!! (from an average of 2.4% to 27.7%)3. These numbers become even more confounding when you learn that businesses founded by women ultimately deliver more than twice as much per dollar invested4. Then how come investors don’t clamor to invest in women?
For quite some time, I have been wanting to write about my experience as a female raising funding. But this topic is rather sensitive, and can easily become divisive, especially as society has become more polarized. Maybe that’s why I avoided it so far.
So I asked my friend Sephi Shapira - one of the best fundraising experts I know - to sit down for a conversation where we shared our experience-based thinking about female founders and fundraising. This is the first article in a small series on the subject.
Meet Sephi
Sephi is a successful serial entrepreneur, angel investor, and fundraising advisor. Over the past decade, he has worked with female founders who have collectively raised somewhere north of $800 million. He is also the father of two young girls and cares deeply about empowering women.
Sephi was both an investor and an advisor in my startup Cheetah, which was a tech-enabled foodservice distributor to restaurants. When our revenue collapsed during Covid-19, most advisors sent me “thoughts and prayers” notes, not Sephi. Rather, he rolled up his sleeves and became part of my war-room, where together with my co-founders we had rapidly executed far-reaching changes to the business, which included massive layoffs and budget cuts. At the same time we spun-off a B2C bulk food delivery to consumers, on top of the core business, which was wholesale food delivery to restaurants.
Though our revenue was a fraction of what it was pre-Covid, once the business had been stabilized, I raised $60M Series C at a valuation which was significantly higher than my Series B. I credit Sephi’s ongoing guidance and advice in helping reach this milestone.
Sephi wrote a book on fundraising - Fundable, and his perspective on why female founders don’t get funded is, by his own description, controversial.
Founders Who Are Agreeable Don’t Get Funded
Sephi’s core thesis is this: fundability is a quality of the founder, not the startup.
This may sound counter-intuitive: as a founder you think you’re pitching your product or service and the market opportunity. Yet, according to Sephi it is not the deck, not the pitch, not even the product. It is the founder - as a person - who is fundable or not. And the traits that make you fundable are specific, learnable, and almost entirely about behavior and mindset.
So that begs the question - what are the female traits that make women less fundable?
“Agreeableness,” Sephi said. “Agreeable founders don’t get funded. And the data shows women are, on average, more agreeable than men. That’s not an accusation - it’s a temperament trait. And it’s the single biggest thing I work to change.”
According to a 2008 cross-cultural research across 55 countries, women consistently score higher than men on agreeableness5. In this study and other research papers written on this subject6, agreeableness is not just “being pleasant,” it is defined as a cluster of six distinct facets, listed below.
Trust - belief in the honesty and good intentions of others
Straightforwardness/Morality - sincerity; discomfort with manipulation
Altruism - active concern for others’ welfare
Compliance / Cooperation - tendency to defer, avoid conflict, yield to others
Modesty - reluctance to claim superiority; downplaying one’s own achievements
Tender-Mindedness/Sympathy - emotional empathy and concern for others
If you are a woman, like me, who’s ever played the fundraising game, I am sure reading through this list brought up some uncomfortable memories. Keep reading, I think you will see why being agreeable works against you.
Female Nature vs Feminine Nurture
Okay, this is where things can get sticky for some people, especially for women; when we start talking about the innate differences between women and men. I believe this triggering point is a legacy of the first generation of feminists who strove to break the glass ceiling by ignoring those differences or brushing them away.
The fact is there are two main reasons for why women are more agreeable than men; one rooted in nature and the other in nurture.
Nature-wise, women have lower levels of testosterone, and agreeableness correlates inversely with testosterone. Studies of girls with congenital adrenal hyperplasia (CAH) - who are exposed to higher prenatal androgens - show personality profiles that trend more toward male norms, suggesting hormonal effects on trait expression7.
Nurture-wise, women are socialized, from childhood, to be more responsive to feedback, more attuned to group dynamics, more collaborative. Men, by contrast, are trained - often harshly, through criticism and competition - to tolerate rejection and push through it.
What happens in a fundraising context, is men tend to hold conviction even when a room is pushing back. Women tend to adjust to the room.
“The single most significant cause for women not being funded,” Sephi said, “is that they tend to let investors take the lead.”
Sephi’s first rule of fundraising is: the founder must take the lead and control the investment process - never let investors take the lead.
Agreeable founders comply with investors to avoid criticism, which breaks the first rule. That’s why fewer women get funded than men. It is not discrimination; it is about behavioral traits and what they signal to investors.
The Paradox That Doesn’t Add Up
Now back to our sad numbers. All-female founding teams get only 2% of all venture capital funding, and if you are a woman, partnering with a male co-founder raises your chances of getting funded by 10x. However, the standard explanation - that it’s discrimination, is quite complicated, when you consider the number of women working in venture capital firms.
The presence of women in venture capital decision-making roles has been rising. Women now hold approximately 15.4% of partner or decision-making roles at VC firms, up from 12.8% in 20208. Among new and emerging fund managers, 42% of new VC firms launched in 2024 had at least one woman managing partner9. There are more female GPs, more female-founded funds, and more institutional pressure on LPs to back diverse managers than at any point in the industry’s history.
One would expect that a larger presence of women in the upper echelons of VC funds will improve the number in our favor. Yet it has not. Perhaps it is the “Queen Bee syndrome” - a term coined in a study that found that women who successfully navigated a “man’s world” often developed a pattern of self-group distancing10.
And perhaps it is not about discrimination, or lack of sisterhood, but a behavioral trait that people aren’t comfortable speaking about publicly. Sephi says that in his experience agreeable male founders do not get funded either.
The Moment You Start Saying No To Investors Is The Moment You Get Funded
“This is what I always say to female founders,” Sephi said, “No, I’m not meeting with an associate - bring a partner. No, I’m not sending the deck before the first meeting. No, I’m not giving you access to my full data room before we’ve discussed terms and timeline. The moment they start saying no, things change.”
The reality is not as straightforward. I can tell you from my own fundraising experience; I’ve been in rooms where I felt I had to prove myself before I’d earned the right to push back. Like the investor had to like me first, approve of me first, and then maybe I could set some conditions.
Here is an example of what this looks like in practice. A female founder starts a meeting by setting her agenda - “here’s what I’ll cover, let’s have questions at the end.” Thirty seconds in, the investor says “actually, can you start with your background?” And she stops the pitch. Because she wants him to like her, she complies. What she doesn’t realize is she just told him: “I will stop doing what I believe is right the moment you suggest something different.”
Sephi says this is the exact opposite of what you need to signal. Investors invest in leaders. Leaders don’t do what they’re told - they do what they think is right for their company. And when you just comply - you are essentially communicating to them that you’re not a leader. The compliance actually signals the opposite of what you as a woman - think it signals.
The “No” Shock Therapy That Worked
There was one story Sephi shared which is a great example of how he works with founders on changing behavior.
He was working with a founder based in New York. She was in her early thirties, top 1% of founders, she had a solid product with real traction. But she couldn’t get funded, no matter what she did. When Sephi started working with her he noticed immediately that she was deeply agreeable - a pattern, he learned, that traced back to a difficult childhood where compliance had been a survival strategy.
So he gave her an assignment that sounds insane.
“In your next three investor meetings, say no to everything. Whatever they suggest, whatever they ask - decline it. Not rationally. Just no.”
You need to be deeply trusting, or desperate, to take this leap of faith; I guess she did not have much to lose. So she did it anyway.
The response from the investors - while not ideal - was more positive than when she pitched before. She came back completely shocked. And then she got funded.
I thought this was both a terrifying and beautiful illustration of human psychology.
Turns out Sephi was basing his advice on a psychological technique called flooding. You cure a phobia by immersing someone in the feared thing until they realize nothing bad happens. So Sephi basically did a version of flooding to cure that founder of her agreeableness. The experiment helped her recalibrate.
Investors Are Guests In Your Reality
“One of the best analogies I use,” Sephi said, “is that the meeting with investors is happening in your living room. You’re welcoming, you’re friendly - but it’s your house, and you set the rules. If you let the investor define the next step, you’re not getting funded. Not because they don’t like you. Because you just told them you’re not running this show.”
Sephi’s final advice to female founders: be agreeable when managing people, lean towards being disagreeable when raising funds.
I couldn’t agree more.
~
Do you have stories to share? Add them in the comments section. I would love to hear your thoughts.
Startup Genome. Only 15% of Tech Startup Founders Are Female (2023). Startup Genome Report
Harvard Kennedy School, Women and Public Policy Program. Venture Capital and Entrepreneurship. Harvard Kennedy School Research
US All In: Female Founders in the VC Ecosystem, Pitchbook, March 2026
Schmitt et al. (2008) - “Why can’t a man be more like a woman?,” Journal of Personality and Social Psychology, Vol. 94(1), pp. 168–182
Costa, Terracciano & McCrae (2001) - Journal of Personality and Social Psychology, Vol. 81(2), pp. 322–331
Knickmeyer, Wheelwright, Hooper, et al. (2009) - “Personality and congenital adrenal hyperplasia: Possible effects of prenatal androgen exposure,” Hormones and Behavior, Vol. 55(2), pp. 285–291
Women in VC & Startup Funding: Statistics & Trends published by Founders Future
Graham Staines, Carol Tavris, and Toby Epstein Jayaratne (1974) - “The Queen Bee Syndrome” Psychology Today, Volume 7, Issue 8, pages 55–60





Ok really interesting perspective and anecdote - but maybe a nuanced approach is best. Studies show that men think women and men are talking an equal amount in a discussion when women talk around 20% of the time - more than that, it is "women are too loud". A BCG report from 2018 shows that women are just interrupted and questioned more than their male peers, and often assumed to have no technical knowledge. So while I agree with the advice that women perhaps should take a more assertive stance and ask for more, it is also my view that that could easily be met with more backlash, as is too common.
So much here to disagree with, but some good points worth consideration.
Disagree: That’s why fewer women get funded than men. It is not discrimination.
This is the actual definition of discrimination.
Disagree: The Paradox that Doesn't Add Up
Saying that now there are women VCs, and women still aren't getting funding proves it isn't discrimination s a flawed conclusion. The gender of the investor alone doesn't eliminate the possibility of bias or discrimination in investment decisions. Women can be biased too.
Agree: Leaders should lead the room and lead a meeting
Agree: Leaders should be firm and have boundaries
Thanks for sharing your perspective