Startup: What to Wear to Pitch

If you’re reading this, you are probably not sure what to wear to a pitch.

So I’m going to start this article by caveating that as much as I would like to think that I have a sense of fashion, in reality, I really don’t… I care, but fashion doesn’t care for me…

Over the last year, we’ve seen a lot of different styles catwalk the InsurTech Gateway and Hambro Perks reception, en route to pitch. Rather than commenting directly on what to/not to wear, I’ll be going through a series of looks/styles/general characters and let you judge my unconscious bias…

Pitch #1 Stashed Up

I’ll start with my favourite and debatably the boldest. This individual is dressed head-to-toe in his own startup branded gear. And when I say that, I mean a branded headband and tote bag on the arm. Not only is he/she clearly representing the brand, but they have come prepared with stash for me too. Clearly, even if we don’t invest, we are expected to indirectly market the startup.

Although I was a fan of this marketing technique, it did draw my attention to their marketing/merchandise spend in their financial information. We declined to invest…

After the meeting, I stashed (pun intended) the branded t-shirt into my desk drawers, using it merely 3 days later when I split a coffee on my shirt. Who’s the real winner here I wonder?!

Pitch #2 The Peacock

This is the main man…He seamlessly slips into the office wearing flip flops and a baseball cap. At this point, he may as well be wearing a vest… This guy reeks of watching too much Silicon Valley.

Some say its a good idea to wear one item of clothing that makes you memorable or reveals personality, but this look takes the Financial Services colourful sock game to a whole new level. There is the chance that they could be remembered as ‘cap guy’, but is that really a good thing?! In reality, it’s the business that you want to be remembered for… not being known as that guy who didn’t take his cap off in an interview. (Call me pretentious)

Pitch #3 Look good, feel good

Many say that “first impressions count”, and I have to admit I think this statement goes a long way. A pitching founder that walks in with an aura of confidence about him or her will likely deliver a great pitch; creating a sense of confidence in them from the audience.

Now, this is not to say that you need to be suited and booted, but rather know yourself and what you are about. In many industries, there are lots of ways your outfit can make a poor impression — badly-fitted clothes, a missing button, dirty shoes or even a heady perfume. It’s not just whether you are formal enough; it’s about showing you know who you are and that you are comfortable in and believe in yourself… There’s no act here.

The shabby startup look is just fine, just don’t distract the investors from your pitch because you haven’t washed in a week.

You have to remember that when you walk into that boardroom, you are asking a group of individuals to invest their own, or their Limited Partner’s money, into you. They must believe in you to deliver on your vision. They will overlook your Mexican Sombrero hat if your product is brilliant and you deliver your pitch with spice… and maybe you supply them with a little tequila.

The reality is, wear what makes you feel comfortable. Don’t dress to impress, don’t overthink it… be yourself

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