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Feminine Leadership: Pitching Like a Woman

When I raised my first VC round as a founder of a technology company, I was scared to be in my feminine leadership. So I dressed up like a guy, with a t-shirt, short hair, and Converse sneakers.

Why Converse?

my sneakers which were the opposite of feminine leadership
Day 1 of VC Meetings…cringe

Because my male mentor at the time proudly walked into his VC meetings wearing Converse sneakers. Which worked for him.

But honestly, I NEVER dressed like this. I loved my feminine shirts and heels.

I was scared.

Scared to be seen as a woman and associated with being “weak” and “emotional.”

It breaks my heart to look back at my photo of sneakers. It makes me cringe.

It’s been 10 years and I ended up raising $40M. But not dressed like a guy.

I got rejected 32 times in a row in those Converse. It wasn’t until my 33rd meeting where I got real with investors and told them I was building a company based on love and respect for the human that I secured our first multi-million dollars of investment.

Deepening into my emotions was my way of embodying feminine leadership.

The key here is to be authentic. No matter how scary.

No matter how many people tell you that you need to fit the dominant culture. You have to stay in alignment with who you are deep down, and that alignment is bigger than any fear or scarcity out there.

And with patience and courage you will be rewarded, as I was, with the success you seek.

Leave a comment below if you’ve ever felt you’ve had to conform to the dominant culture and lose yourself. How did you overcome that?

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