“And so I wear glasses when I go into investor meetings in order to look more intellectual and like a legit CTO.”
I was out to dinner in Palo Alto in 2011 with a handful of super smart technical women. I was the least technical of the bunch (and lucky to get an invite!); I was technical in resume but not a day-to-day engineer like the rest of them.
One topic we discussed was our problems with fundraising. One of my dinner-mates was discussing how it was difficult to establish credibility in investor meetings. She was the CTO and her male co-founder was the CEO. Investor meeting after meeting, investors would ask him about how the technology worked even though she was the one who wrote all the code. One or two well-known VCs they met with did not believe she wrote the code and thought the team had other engineers.
Finally, after lots of frustrations, the two co-founders had a weird conversation:
CEO: “I need you to dress nerdier. You need to dress like an ‘engineer.’ Can you wear jeans and a t-shirt? And wear glasses?”
CTO: “I don’t wear glasses. I don’t need them.”
CEO: “Well get fake ones!”
Although she was apprehensive, she did end up buying glasses for their investor meetings. The team got funded, and they were on their way. They would later sell their company successfully two years later to a large tech company in the Valley.
I almost could not believe this story. And yet, I did.
After I finished raising for LaunchBit in 2011, looking back, I realized that all of my investors whom I met in person met me when I was wearing one particular skirt. I wore 3 different outfits for fundraising – dress pants, a long skirt, and a tea-length skirt – but only the tea-length skirt led to money. This is what it looked like:
Like my friend who wore glasses to her meetings, I can’t be sure if it’s coincidence or not. That said, when you’re doing hundreds of meetings, the data does start to mean something. I certainly didn’t split-test my clothes in a systematic way, and I can’t tell if it was the clothes or my confidence in those clothes affected the outcome.
There are a couple of takeaways from this:
1. What you wear does matter
Even if VCs say they don’t care what you wear, subconsciously, everyone forms an impression of you in the first 30 seconds based on what you are wearing.
Of course, it goes without saying that what you wear should be professional and comfortable.
2. Don’t be afraid to test different outfits
I feel ridiculous writing this point. I hope in the next 5 years to be able to delete this part of the post. If you have more fundraising success with a certain outfit, go with it.
I had actually started writing this post in 2011 (special thanks to my friend Omar Seyal for reading drafts of this back then), but I never posted because I felt so uncomfortable writing this. It’s time to get the dialogue in the open, and I welcome comments below.
Beyond that dinner in 2011, I’ve heard enough anecdotes from other entrepreneurs about fundraising and attire to realize that despite what everyone publicly says, what you wear to investor meetings does matter.