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You Can't Lead A Company Without Feeling Confident In What You Wear

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Most startups and businesses give plenty of attention to their company culture. They host innovation sessions, offer free lunches, install foosball tables and bike racks.

But when it comes to style, the company is often overlooked. In fact, even out of date, out of style, or completely disconnected from who and what uses its products.

Yet your business’ style can be an enormous part of market position and what draws customers in. It goes beyond branding, messaging, and colors used in your various digital and physical assets to everything from how your executives speak to how they dress.

A great example is Steve Jobs. He must have had dozens of black mock turtleneck tops and midwash jeans because it was his go-to look for a long part of his career. But while most people would have thought this was a detriment to Apple, that look spoke exactly what Apple is about to this day: Sleek, streamlined, simple, polished.

Mark Zuckerberg is another good model for the role that a founder’s style can play in a company’s DNA. While he may have been criticized for his choice of hoodie sweatshirts and Adidas sport sandals when on stage, that is exactly what Facebook’s initial core user base was wearing and could likely identify with. Would they have attached to Facebook if not? It’s hard to say but it likely played a part in the company’s allure to them.

Y Combinator’s Paul Graham wore Birkenstocks on stage when I saw him speak, which isn’t that far off from the innovative, aspirational youthfulness of the Y Combinator brand. It definitely plays a big part in my own personal style as a founder as well as for my business. Everything about Condiment from the notecards I send out to say thank you to the way I speak to the audience to what I wear is geared towards the company and its brand.

While consulting with LA based startup Glossi.com, CEO Matt Edelman and I had this very conversation. As he jetted to speak at CES, I had asked him, ‘What are you going to wear?’

We shared a laugh about it but Matt’s style, along with everyone at the company, is as woven into the company’s overall vibe as anything else and it plays a part. From there it’s in everything; the walk, the talk, you name it. Glossi’s done a great job of communicating its company style—cool, innovative, creative media company—because it recognized the role style plays. It’s not a surprise that Glossi is attracting that type of brands and creators.

There are a lot of other great examples in the market.

So, how do you find your company’s style and how do you build on it from there?

  1. It starts with your customer. Your company style isn’t really about you, it’s about your customer first. Anything else might alienate them and put them off. Condiment’s readers are similar but a bit different than me and the company’s style is most centered to it. Where the role a founder and execs play is in a synergy with this.
  1. It involves your message and brand. Your company’s style is an extension of your brand and message. So, if world changing and approachable is your message and position, work that into every element of the business. Leave no stone unturned.
  1. Market and geography play a part. Union Square Ventures breathes West coast fresh and innovative, but East coast sharp and professional, a perfect match of its market (tech) and location (New York). Glossi’s very similar to a lot of companies based in the ‘Silicon Beach,’ while Google embodies a lot of the spirit of the Silicon Valley.
  1. In the end, all companies are essentially a ‘lifestyle brand’ – That doesn’t just mean lifestyle companies alone but all companies. We all represent the ideas, minds, likes, interests, dislikes, needs, wants, locations, price points or income, etc. of the market, category and our customers. Founders and executives fit in from there.
  1. Don’t try to fake it. A lot of companies try to be what they think is cool or trending at the moment versus what they are. It doesn’t work. Great company style is in part accepting the reality and truth of what your unique company and its vibe is

Most of all, don’t be afraid. You shouldn’t need to fit any mold but the one that is right for your company and its customers. Microsoft gets knocked for being as square as it gets, outdated, etc. but it has a lot of legacy, old school position and it works. Your company style, like all style, doesn’t need to be anything but authentic, appropriate and fitting. What that looks like is as unique as your business is.

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