Pitch dress code. How to dress when meeting investors

Dress code. Really? You have so much stuff to deal with growing your company with like, no resources, and having to beg investors for cash to make the hires you need to close. Seriously, now we’re talking about fashion with VCs?

Well, you’re reading this blog, aren’t you? 😉 Doing stupid things isn’t on your to-do list (hopefully). Don’t worry, we’re going to go through this in detail. And honestly, it’s pretty simple.

Overdress or underdress?

If you have a meeting lined up with an investor, you’re probably thinking about this in binary: is it better to overdress or underdress?

That’s not the right question as it depends on your baseline. Mark Z clearly has a view of a casual baseline and that shizzle won’t fly if you are a financial, enterprise dweeb. You wouldn’t be caught in a hoody on a sick day.

But sure, over or under? Pick one.

You’re probably intuitively saying overdress rather than underdress. But that’s not quite right.

  • Overdressing can imply that you are desperate to impress the investors and you may be portraying someone who is not you. In that case, you come across as inauthentic as you are not comfortable with yourself. Imagine wearing a suit two sizes too small and holding in your breath. You’re going to come across weird.
  • Underdressing to the point of ambivalence implies you are lazy and don’t take the meeting, nor the investor seriously.

You need to portray your business character in your dress code. It is imperative that you take that into consideration because you don’t want to start engaging your potential investor with a false start.

Underdressing

If your chat is quite normal, then you shouldn’t underdress. Your appearance can actually compensate a little 😉 A smooth, but not a super bright talker, that is well dressed creates a mini reality distortion field. Yes. I’m basically saying you can bulls*** your way to funding. I’ve seen it. My bet is the founders won’t get anywhere, but who knows. But let’s be honest, you want to get funded by hook or crook, right?

You really only have downside looking like a hobo. Think about it. Have you ever heard of someone getting a job for looking fly, but I’m sure you can believe someone going to an interview and getting nixed for wearing shorts. Makes sense, right?

VCs don’t really care about how you are dressed. But if you look like you’re too dumb to be aware you look ignorant, or that you don’t care, you’re making issues for yourself out of your own negligence. Shame on you.

Suranga Chandratillake, a GP at Balderton Capital, advises against what one might think are extremes:

There’s a low bar, but you probably shouldn’t wear shorts. In any given week I see people in T-shirts to suits, but suits and a tie are rare.

Suranga is being a little polite, but he made the point I want you to internalise:

  • Don’t be ignorant: Don’t wear shorts
  • Don’t suit it and boot it unless it makes sense, to you

Overdressing

Underdressing is basically being ignorant.

Do you know what though, overdressing is just… weird. A VC might take kids to a pantomime, but they don’t want Dick Whittington playing the pipes in their boardroom.

Can you imagine a Breakfast at Tiffanys’ moment where a founder arrives in a tiara and little black dress? You’re thinking, wtf is going on right now? Is there a camera?

Yes, you can overdress. Wouldn’t you wear a black tie to a pitch? That’s clearly an extreme.

Don’t be weird.

If you’re a bit flamboyant as a personality, your dress can reflect that. But can you imagine a back-end engineer in a Brioni suit explaining “middle-out”?

Be authentic

If you want a safe uniform, you can’t go wrong with this:

  • Khakis, shirt with collar and normal brown shoes (with or without sweater)
  • Dark jeans, white collared shirt, blue blazer and normal brown/black shoes

But being authentic is always about being true to you. Truth is investors have expectations with whom they are meeting.

Bill Reichert, MD at Garage Technology Ventures believes the best entrepreneurs strike a balance between the customer and the VC. A balance between the two means entrepreneurs find a look that gives them credibility.

How would you dress if you were meeting with a group of customers? If you are building a VR game, you would probably have a cool T-shirt with your logo on it. If you are selling enterprise software, you would probably have a sports coat, if not a suit. A young game developer wearing a suit is not at all credible, an old fart wearing a T-shirt and jeans is painful to look at.

There are some expectations depending on your category of startup:

  • Social/ecommerce: Jeans and shirt or your startup shirt
  • Sports: A tight Under Armor shirt with khakis and a few muscles
  • Fintech: Bit banky, meaning a white button down shirt and suit trousers. You can wear a jacket if it is you
  • Fashion: Dress up like you are meeting GQ. If you are female, just stop short of a ballroom gown (That’s weird, right?)
  • Gaming/security: Non-ripped jeans and Tor t-shirt AND pizza stains
  • Healthcare: Similar to bankers, but you might get away with a tie if you are doctor. Again, that’s authentic to you
  • VR/AR: Non-ripped jeans and a Reddit t-shirt

I also think it changes by stage. The earlier you are, the more casual it’s almost expected you to be. You’re busy, broke and need to get your s*** together. Later stage companies imply you have more people and more time to like, get dressed.

  • Angel: What you would wear to meet a friend at a normal restaurant. It doesn’t really matter, but don’t wear anything you would be ashamed to be seen in if an ex-gf stopped by (ie. Crocs). I actually LIKE seeing founders in their startup branded t-shirt at this stage
  • Seed: Similar to Angel, but up your game a bit. For a little seed, sure, wear your startup t-shirt, but if you are raising $5m+ then wear a collared shirt at least. Jeans or khakis etc, don’t matter. Just not ripped
  • Series-A: You want to take things a little more seriously, so investors take you seriously. You’re talking bigger money, so why take the risk?
  • Growth: You can actually do whatever you want as investors are knocking on your door. But you can’t go wrong with being formal. You may even have a CFO from an investment bank, so there you go

The final interesting factor is age:

  • Old: If you are 40+ (or at least look old), dressing more formally is natural. Would you think it weird for a 45-year-old to wear a casual suit? No, not really. It’s probably very normal for you
  • Young: If you are in your late teens, early 20s then one would expect you to be more casual. If you are a bit aristo with a signet ring, then appearing dapper is authentic to you, right? That’s fine too

Suits are dangerous (most of the time)

When I was fundraising for an enterprise AI company I always wore suits. We were selling to major investment banks, so we dressed to match clients. I wore a suit pretty much every day on the odd case I would pop over to see a COO of a bank. Only if I was pretty sure I wouldn’t have a meeting would I wear whatever I wanted. But it wasn’t really worth the risk. Suits for client facing execs was just what we did (of course the devs did whatever they wanted, even when they came to meet clients! Clients almost expect it, ha!).

So when it came to pitching VCs I wore suits. No one really batted an eyelid. I was pitching super nerdy stuff and telling them about the millions banks would pay us. I used to work in M&A so I’m comfortable in a suit. It’s normal to me.

There was only one VC who laughed at me. But I’m friends with a lot of VCs and this one was a drinking buddy. I took off my jacket and told him to go f*** himself, lol. I did feel a little embarrassed as I really didn’t need to wear the jacket. But I like fancy pocket scarfs, so I like the excuse 😉 But how I dressed didn’t matter at all. Traction and the pitch did.

So why tell that story?

  • It was congruent to the business we were engaged in
  • I was comfortable in a suit and it didn’t distract me from pitching
  • 80% of the time I was pitching people I knew, so it didn’t matter. It was just me reflecting the startup in new dress code
  • I was authentic

But, 99% of the time this is NOT going to apply to you. If you are an ex-banker, maybe a bit introverted and/or older, and working in fintech, no one is going to think it strange you wear a suit. No one. Do you know what, a lot of fintech investors wear suits too…

But most of the time and for most investors, you’re going to come across a bit weird in a monkey suit. And some VCs hate suits.

Peter Theil (You know who he is) has a hatred of suits:

Maybe we still would have avoided these bad investments if we had taken the time to evaluate each company’s technology in detail. But the team insight —never invest in a tech CEO that wears a suit — got us to the truth a lot faster.

Jeff Clavier, managing partner at SoftTech says:

We want people to be themselves. An investment will potentially be for five, seven, 10 years. The last thing I want is to have someone show up in a suit and a tie when it’s clear they’re not used to it.

Peter is Peter. Jeff’s point is more valid. You need to be authentic, comfortable.

Finally, Mitchell Kertzman, MD of San Francisco-based VC firm Hummer Winblad Venture Partners.

Entrepreneurs who present to us are often engineers by background . . . what they say is overwhelmingly more important than how they look. Don’t come looking like you’re dressed for the beach and don’t come looking like a fashion model. After you leave, you want us to be talking about your product, your team, your technology, your business plan — but not how you looked.

Safe Bet: Business Casual

Ross McCammon, Articles Editor, GQ magazine says:

A general rule of thumb for an appropriate dress when speaking with VCs seems to be “business casual.” Here’s a sample outfit that fits this profile, starting from the ground up: black dress shoes or boots (no sneakers, flip-flops or Crocs), a nice pair or jeans or dress slacks (no rips, darker shades work better, in my opinion), solid color t-shirt or polo (collared shirt with no tie could work also), and a black casual sport coat.

 

1) Forced casual: There are few approaches to style more unfortunate than attempting, through fashion, to look more laid-back than you actually are. And the perpetrators are so crucially unaware of their sins. They have no reference point other than the one they’ve attempted to borrow from someone else. Their children, for instance. A few questions to determine if you’re forcing the casual: Are you wearing shorts even though you’ve never thought of yourself as a “shorts” kind of guy? You might be forcing the casual. Are you wearing eyeglasses that would look better on a German filmmaker? You might be forcing the casual. Is there a reference on your T-shirt that you’re not familiar with–Galaga, Eight is Enough, a random summer camp in Wisconsin? You might be forcing the casual. Are you successful stand-up comedian Jeff Foxworthy? If so, thank you for years of chuckles.

2) Ambivalent casual: Zuckerbergian. Like, a hoodie. A pair of shorts. A pair of flip-flops. All set against a worldview that somehow allows for being both wide-eyed and smirky. To pull this off you have to be really good. Really good.

3) Business casual: A now-meaningless term left over from the ’80s. It involves pleated pants, wrinkle-free button-downs and a bit of fence-walking that is not recommended.

4) Unimpeachably casual: Which is to say: appropriately casual. Which allows for “formal.” Which is ironic. Which means: Now is the point of the discussion when we must look to the Italians. There’s this helpful Italian concept called sprezzatura,which dictates that perfection comes from the slightly imperfect. It’s an old idea that was reintroduced to the world in 2006 by Esquire Fashion Director Nick Sullivan in the original Big Black Book, Esquire’s biannual style manual. It allows for whimsy, messiness, flaws. Your tie is askew. Sprezzatura! That pocket square seems unnaturally bulbous. Sprezzatura! You’re wearing your company-logo golf shirt inside out. Sprezzatura, man! Sprezzatura promotes a sense of style but allows for comfort, individuality, even ambivalence. What the Italians are saying is (and this is a loose translation): “Give a s***. But only up to a point.” Sprezzatura lets you look formal and casual at the same time. (Another helpful thing Sullivan taught us: “Always cut. Never pull.” He’s referring to the occasional stray string, but it’s a useful metaphorical notion for business.)

Don’t be weird: Plus or Minus 20%

The point of dressing appropriately is to not only convey that you have the wherewithal to make the simplest of decisions, but also to keep the VCs focused on what’s important – your product and your business. If there is any question about what you’ve decided to wear to a pitch, this will ultimately distract the VCs, preventing them from being sold on your idea.

New York VC Steve Brotman, co-founder of Greenhill SAVP, gave The Wall Street Journal an example of very distracting clothing worn by an entrepreneur pitching him an Internet startup during the dot-com era. According to his story, a woman dressed in a strange green outfit entered his office unannounced and offered up a business plan. “You lost me at hello,” Brotman told her.

The woman was selling a product with “avocado” in the name, and was attempting to dress like an avocado. “I’m not about to do a deal with a lady dressed like an avocado,” said Brotman. The lesson here? Don’t let your product influence how you dress; VCs don’t enjoy gimmicks.

My mate Simon Menashy, a partner at London-based MMC Ventures says:

Be credible and that doesn’t mean suit up. It means be sensible. I have turned someone down because they weren’t wearing their product — although it wasn’t the only factor.

Jim Barksdale:

Our dress code is, you must dress.

While your appearance should not be distracting or influenced by gimmicky product promotion, if done right you can use it to your advantage. Boulder’s Andrew Hyde of TechStars suggests entrepreneurs use the “20% rule” when deciding what to wear.

You want to look 20% better or worse than your actual position,” he says. “The key is to either look good enough to make them think you’re trendy, or bad enough to make them think you’re hungry.

I would recommend going the safe route, but more confident entrepreneurs could use this tactic to their advantage. Hyde, who also co-founded a clothing line of humorous T-shirts for venture capitalists, says whatever you do, “Don’t wear a blue shirt, or they will think you are mocking them.

Some tips for women

I would strive for casual to business casual. Definitely, don’t wear a suit-you’ll be known as the uptight company that doesn’t get the startup lifestyle.

If your company sells high-end fashion, then you should probably dress nicer. In my case, my company is a hardware tech company so I stick to the more conservative, plain “nice-casual” outfit.

Probably aim for the upper end of business casual.

  • Plain top
  • Skirt or nice jeans
  • Closed-toe black high-heels
  • A watch
  • Earring studs (do not wear any dangly earrings-too distracting. Don’t wear any jewellery that makes noises either like clunky bracelets)

Conclusion

It’s really not that complicated. If you wear a nice shirt and khakis, or simple professional dress, you can’t really go wrong.

Don’t be weird. Be true to the best you.  VCs care what comes out of your mouth more.

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