Finance & Operations

Hey, Female Entrepreneurs: Show Up to Investment Meetings and Lean In!

September 4, 2013

While some might blame the lack of venture-backed, female-led businesses on sexism, .406 Ventures founding partner Maria Cirino doesn’t see it that way. In this post, the former Ernst & Young Entrepreneur of the Year shares her own experience raising capital and explains why the issue has much more to do with confidence.

Typically, when Maria Cirino and her fellow partners at .406 Ventures enter investment meetings with female entrepreneurs, the tech veteran — who has founded two successful tech companies and an early stage VC — says she notices two distinct things about them.

First, they tend to be less arrogant — which Cirino says is a breath of fresh air. And second, they seem to be more hesitant to actually ask for money — which Cirino finds odd given the underlying purpose of the meeting.

“To me, the second issue is a matter of confidence more than anything else,” explains Cirino, who has spent the last 25 years building, founding, and investing in technology businesses. “Generally, male entrepreneurs enter investment meetings and expect to walk out with a term sheet. If they don’t, they’re shocked. Female entrepreneurs, on the other hand, seem to view those meetings as a forum for advice or consultative fact-finding. If they walk out with a check, that’s great. If not, oh well.”

That mindset needs to change — and soon, says Cirino.

The reality is many investors are eager to invest in female entrepreneurs with great ideas or proven business models. The opportunity for them to do so, however, remains infrequent.

“The gap between male and female entrepreneurs that we see at .406 Ventures is improving, but not to the degree that I’d like to see,” Cirino suggests. “Less than three percent of the pitches I hear are brought in by women, and I think it should be closer to 50 percent. Needless to say, we have a long way to go.”

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Marissa Mayer and Sheryl Sandberg

Cirino’s insight doesn’t just come from the perspective of a lifelong investor, either.

In 2000, she raised her first round of institutional financing as the founding CEO of  Guardent, a managed security services provider. And despite only pitching her business to male venture capitalists, she came away with three term sheets.

“I never felt like I was in a meeting with someone who was or wasn’t paying attention to me just because I am a woman,” Cirino recalls. “In my opinion and experience, the sexism or gender bias that many women think is prevalent among VCs doesn’t really exist. Are there exceptions? Of course, but those exceptions are the minority. Most VCs simply want to see confident entrepreneurs who believe in themselves and their ideas, have developed a change-the-world concept or technology, and have what it takes to grow a good idea into a great company. Whether those entrepreneurs are male or female is generally irrelevant.”

From that perspective, Cirino believes that female entrepreneurs can learn a lot from the way that successful female tech executives like Facebook COO Sheryl Sandberg and Yahoo! CEO Marissa Mayer have managed their careers.

“The ‘Lean In’ philosophy that Sandberg talks about in her book is spot on with the experience that I’ve had as a female entrepreneur and investor,” Cirino says. “As a woman, you need to have the confidence to really go after something you believe in and not be afraid to put yourself out there.”

The Right Way to Approach Investor Meetings

“Ask yourself if you really believe in your business and if you’re willing to fully commit to it. If you can confidently answer yes to those questions, then go after it like you’ve never gone after anything in your life.”

Maria Cirino

Maria Cirino, .406 Ventures

At the end of the day, Cirino says that while some VC stereotypes might be true, the one that is absolutely bogus is that VCs are sexist when it comes to who is behind a highly differentiated idea or technology that addresses a big market problem or opportunity.

“Honestly, the best venture capitalists are completely gender blind when it comes to making investments,” Cirino explains. “They exist to make money. If they see a good idea that’s highly differentiated and supported by good technology, they truly don’t care if it’s a monkey who is presenting it. It’s a success-based decision, not a gender-based one.”

In fact, Cirino says investors simply want to see that an entrepreneur possesses core qualities, including enthusiasm, integrity, energy, acumen, killer instinct, and leadership. And very often, those qualities are best conveyed when an entrepreneur can confidently communicate what it is they do and why they are doing it.

So, what would Cirino suggest female entrepreneurs do as they prepare for their next meeting with potential investors?

“Ask yourself if you really believe in your business and if you’re willing to fully commit to it,” Cirino says. “If you can confidently answer yes to those questions, then go after it like you’ve never gone after anything in your life, because that’s what your male counterparts are doing. You may not come away with an investment, but that doesn’t mean you’re a failure. Every investment meeting you have will help you form new relationships and gain valuable experience, both of which are critical to long-term success.”

Additional Resources for Pitching VCs

Don’t Raise These Red Flags

Rincon Venture Partner John Greathouse on 8 Deal Breakers that Send VCs Running

4 Common Mistakes to Avoid at All Costs

OpenView Associate Ricky Pelletier on How NOT to Go After VC Funding

We Want to Hear from You

Do you think sexism still exists when it comes to raising VC funding?


Founding Managing Director

<strong>Maria Cirino</strong> is a founding partner of <a href="">.406 Ventures</a>, an investor in early stage technology companies. In her 25-year career, she has led two tech companies to successful IPOs, and has been recognized as the “Massachusetts CEO of the Year” and “Ernst & Young Entrepreneur of the Year.” Currently, she sits on the board of .406 portfolio companies Attendware, Bit9, Digitalsmiths, Kaltura, Mineral Tree, Vaultive, and Veracode.