Venture Capital Fashion Statements
Do the clothes an investor wears correlate with their success?
Studies have shown that Mark Twain was right, “clothes [really do] make the man.” In fact, one study from Northwestern shows that what you wear can affect how you think and perform. After reading the study I wondered if there was any correlation between what a venture capitalist wears and how he performs. It turns out that VCs that buck the standard VC fashion norms by not wearing a blue button down shirt, khaki pants, and (if it is chilly) a Patagonia vest vastly outperform their peers. In fact, the more a VC blazes a new fashion trail the better their returns. Fewer than 12% of VCs are considered “successful” and a surprising number of these successful VCs have a unique or specific fashion sense. Here are just a few that stand out:
Chris Sacca — Cowboy Shirt
My first encounter with Chris and his trademark cowboy shirt was at SXSW where he was judging a pitch competition. We ended up winning the event and I got a chance to ask him about the shirt. It turns out he bought his first button-down cowboy shirt with ornate stitching at an airport gift shop in Reno, Nevada. The shirt had been marked down 80% and was an immediate hit with the entrepreneurs at the conference he was attending. While some people may take offense at what could be seen as appropriation of cowboy culture, the billionaire investor explains that he wears the shirt to remind himself not to take himself too seriously. Whatever the reason the shirts seem to have worked.
Firm: Lowercase Capital
Investments: Twilio, Twitter, Stripe, Uber
Dave McClure — The Branded Black T-shirt
Shortly after I met Chris Sacca I met Dave McClure at the Four Seasons. He was wearing his black 500 Startups branded t-shirt. He ended up investing in my next startup and in each of our subsequent meetings he was wearing his trademark branded black t-shirt. During his tenure at 500 Startups Dave ate, slept and breathed the firm — he was a walking billboard for the brand and his shirt telegraphed his commitment to his firm and the entrepreneurs they supported.
Firm: 500 Startups (formerly)
Investments: Twilio, Credit Karma, Grab, Udemy, Ipsy, Talkdesk
Brian Singerman — Sportcoat + T-shirt
It is very common to see software developers in t-shirts and jeans — a uniform Brian Singerman became accustom to as a software engineer at Google. When he left to join Founders Fund in 2008 he decided to dress up his standard uniform with a sportcoat — it seems to be working as he was promoted to partner seven years ago and has been going strong ever since.
Firm: Founders Fund
Investments: Stemcentrx, Oscar Health, Stripe, Wish
Michael Moritz — The Sweater
Michael Mortiz is one of the most successful VCs in history and much of his success could be due to his traditional v-neck sweaters.
Firm: Sequoia Capital
Investments: Zappos, LinkedIn, Stripe, Instacart
Bill Gurley — The Undershirt
Bill Gurley has a diverse wardrobe, but the one constant is his undershirt. You’ll never catch this Benchmark VC without his trademark crewneck undershirts. In fact, he has even been known to wear undershirts under his t-shirts. The one thing to remember is that undershirts aren’t t-shirts — they are thinner and generally ribbed — t-shirts are often bigger, ticker, and stiffer.
Investments: Uber, GrubHub, OpenTable , Zillow , Stitch Fix
Peter Fenton — Half Zip Sweater
Peter Fenton, like Michael Moritz, loves to wear sweaters, but prefers the half-zip vareity as opposed to Mortiz’s traditional v-neck sweaters.
Investments: New Relic, Quip, Twitter, Zendesk, Docker, Elastic, Zuora
Josh Kopelman — The Tux
Josh Kopelman, known as the 007 of Silicon Valley, is routinely called out for being the best dressed investor in the Bay Area. Very few investors can pull off a tuxedo, but Josh is certainly the exception and his returns prove it.
Firm: First Round Capital
Investments: Bazaarvoice, OnDeck Capital, AppNexus, Clover Health
Jeff Jordan — The Lucky Shirt
Many of us have that one go-to shirt. For some of us that shirt may be lucky, it may be slimming, or it may just be comfortable. Jeff Jordan’s favorite shirt is a checkered dress shirt. He wears it to all of his important meetings at it has obviously brought him a lot of luck.
Firm: Andreessen Horowitz
Investments: Tilt, Airbnb, Instacart, Pinterest, OfferUp
Ravi Mhatre— The Exception That Proves the Rule
While most venture capital partners wear the traditional blue shirt and khaki pants — they’re copying Ravi Mhatre (with less than stellar results). Ravi popularized what has become the standard VC uniform — as the originator he’s had great success with his blue shirts. Remember, bucking the trend sometimes means you’ll eventually set the trend.
Firm: Lightspeed Venture Partners
Investments: AppDynamics, Mulesoft, Nutanix, Clever, Stitch Fix
Alfred Lin — Cowboy+Undershirt
Sometimes innovation can be additive. Sequoia’s Alfred Lin borrowed Chris Sacca’s cowboy shirt and combined it with Bill Gurley’s undershirt to create an entirely new fashion statement. Obviously, it has worked very well for Lin.
Firm: Sequoia Capital
Investments: FutureAdvisor, Airbnb, Houzz, Doordash, Uber
The moral of the story? If you’re an institutional investor looking to invest in a VC fund — make sure their professionals aren’t wearing blue shirts and khaki pants (unless you’re talking to Ravi Mhatre).