Worst Corporate T-shirt Designs Ever

Don't Hate My Swag Guy Kawasaki’s The Art of the Start, addresses a number of valuable startup issues, including fundraising, partnering, branding and beyond. In addition to these foundational startup issues, Guy also briefly discusses how to properly design a corporate T-shirt.

When I evaluated Guy’s book for its potential use in my UCSB entrepreneurial classes, I was impressed overall, but I thought his comments on T-shirt designs were gratuitous. My initial thought was, “Guy, are you really telling me how to design a corporate T-shirt?”

Then I took a moment to consider a couple T-shirts we developed at Expertcity (creator of GoToMyPC and GoToMeeting, acquired by Citrix). Upon reflection, I realized that we would have been well served if we had applied Guy’s T-shirt suggestions.

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As described in Lousy Product Names, Expertcity was initially a marketplace for services in which users utilized our technology to solve technical support issues. In our attempt to make this flawed business model successful, we partnered with Sun Microsystems. They licensed our screen sharing technology to support their StarOffice customers.

As part of the launch of this new service, we collaborated with Sun to design a T-shirt. The logo that was displayed on the shirt is show below. In isolation, it appears fairly innocuous. Our message was, “If you need help, all you have to do is click.”

Need Help

In those days, I derived as much value from Expertcity’s SWAG as I did from my meager paycheck. When I came home wearing the Sun Microsystem T-shirt, with an extra one for my wife, she took one look at it and responded, “I would never wear that.” I was shocked, as she generally welcomed a chance to promote Expertcity. However, her reaction was clear when she poked me, literally “clicking” on the logo.

Getting “clicked” on the nipple is not welcomed by most people, especially women. However, before you become indignant at the insensitivity of the men who undoubtedly designed this shirt, take a breath. It was actually designed by two women, a VP at Expertcity and a VP at Sun.

Need Help Click Here



One terrible T-shirt design should be enough for any startup, but we managed to come up with two. To promote the Expertcity marketplace, we created the following design.

Click Me

Seen up close, the text is not particularly compelling, nor is it particularly offensive. However, when seen from afar, the message changes considerably.

Click Me Far View

If you do not see anything other than “click me” in the above photo, ask a friend.

Not only is this shirt offensive, it breaks most of Kawasaki’s rules of T-shirt design, which are summarized as follows:

Do Not Use White – It quickly becomes dingy, reducing its life. We, of course, used white.

Minimize Text – We did adhere to this suggestion, although our execution was abysmal.

Use At Least A 60-Point Font – We blew it here. Our tiny font contributed to the potential misinterpretation of our messaging.

Spend Some Money On Design – Epic fail here as well. We did everything in-house.

Make Kid Sizes – Thank goodness we did not adhere to this rule, as we might have been arrested for child endangerment.

List Source: Guy Kawasaki, The Art Of The Start

Satisfied Students

I have used Guy’s clever book in my New Venture Creation class for the past five years, sharing it with thousands of students. Categorically, they find the book to be extremely additive to their entrepreneurial education. My hope is that they learn from Guy’s thoughtful discussions of numerous entrepreneurial issues, including branding, promotion, product development AND T-shirt designs.

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John Greathouse is a Partner at Rincon Venture Partners, a venture capital firm investing in early stage, web-based businesses. Previously, John co-founded RevUpNet, a performance-based online marketing agency sold to Coull. During the prior twenty years, he held senior executive positions with several successful startups, spearheading transactions that generated more than $350 million of shareholder value, including an IPO and a multi-hundred-million-dollar acquisition.

John is a CPA and holds an M.B.A. from the Wharton School. He is a member of the University of California at Santa Barbara's Faculty where he teaches several entrepreneurial courses.


Note: All of my advice in this blog is that of a layman. I am not a lawyer and I never played one on TV. You should always assess the veracity of any third-party advice that might have far-reaching implications (be it legal, accounting, personnel, tax or otherwise) with your trusted professional of choice.





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