5 Lessons From the Funniest CEO on the Planet, Fred Durham

I had the pleasure of interviewing Fred Durham, Founder and CEO of CafePress. CafePress was founded in 1999 and pioneered the online print-on-demand business model. They started as an online platform for users to create their own products and sell them online through their own webpages with no inventory risk. They did this by producing the products on-demand, only after they had been ordered. This innovative approach earned them two Webby awards. Today, the CafePress community has created over one billion unique items, sold over 20 million T-shirts and paid more than $140 million in commissions since 2006 to product creators and shopkeepers.

Thank you so much for doing this with us! What is your “backstory”?

Like my parents, I dropped out of high school at age 16. I grew up in a very solidly working-class, or perhaps sometimes, out-of-working class, home. There are pockets of these in rural America, in lower class suburbs and inner urban areas. They feel like traps — cycles of poverty with no clear exit. My parent’s goal for my sister and I was to break us out. They made it clear that we didn’t have to accept the way things were and instilled in us that we could go anywhere and do anything. Their sacrifice taught me a lot. We did get out, and I’m still running. I did end up going to college, and thought I wanted to give back — perhaps become a teacher. After graduation I took a trip to India with money I had scraped together by pocketing my meal plan money. After backpacking for four months, I came back changed — a little more Ronald Reagan than Mother Theresa. So I chose to embark on a career in business. To me, businesses were the citizens’ sustainable method of changing things. A profitable business didn’t have to mean greed and evil. A sustainable business works to make people’s lives better — through selling products people want and need, perhaps saving them money, and generating profit that pays people fair wages so they can help their kids. Entrepreneurship is a form of citizen activism. I moved to Silicon Valley, which to me is “Hollywood for geeks.” It was the mid-90s, the beginning of the Go-Go years. I was doing contract programming at the time, keeping one eye open for what I hoped would be my big break. Maheesh, my friend and ex-college roommate, called me with a crazy idea: a “1- 900” singles dating line. Think: a pre-internet, touch-tone Match.com through the phone wired to your wall. I thought it sounded totally stupid, but told him if he could sell it, I’d program it. A week later he had a contract with the #1 radio station in Seattle to launch a co-branded version. So, we moved to Seattle. We sold that business in less than a year and then went on to start 10 companies together, including CafePress. (By the way, the other eight basically failed.)

CafePress is a specialty retailer that offers made-to-order clothing, housewares and accessories that are personal to you. We believe in the power of conversation and provide a way for anyone to turn ideas, beliefs, values, identities — something you are passionate about — into something they can share with friends, family or with the entire world. Put simply, if there’s something on your mind, we help you share it with the world.

Can you share the funniest or most interesting story that happened to you since you started your company

For people that know me, running a 1–900 dating service would probably make them laugh milk through their noses. For CafePress, there’s lots of funny stuff. But one the of the, “you’re not prepared for this,” moments was when the Secret Service showed up at our office. As a UGC (user generated content) business, someone uploaded to CafePress a spoof movie poster of Kill Bill, but instead it said, “Kill Bush.” These were the early days, before Facebook and Twitter, so it wasn’t clear how to handle this type of content. We learned quickly that that’s an area of free speech that’s a little off limits. And the Secret Service seemed to understand that a poster of George Bush dressed like Uma Thurman was probably not an actual national emergency.

What makes your business stand out? Can you share a story?

That’s an easy answer for me: our customers make our business stand out. Their stories — which are essentially the way they express themselves and their points of view, challenge our world. It’s a daily growth experience. Example: when Hillary called Trump supporters deplorable, within hours we had tshirts and bumper stickers on our site declaring, “I’m a Deplorable.” Here’s another example: shortly after I came back for my second run as CEO I had the privilege to speak with a customer that had a mug that said, “It’s a trap.” The mug had broken after a few years of use, and she was quite passionate about getting a replacement. It didn’t seem like a very impressive design to me at first. Plain black text. But she explained that her siblings used that as a warning and joke growing up. Peel back a layer and this mug with, “It’s a trap,” was a connection to her brother. So to her, it wasn’t just the mug that broke, but a bit of the connection as well. She and I kept up a short correspondence and I found that she was a really interesting person — very giving to others and volunteering time for causes. It was a reminder about how passionate our customers are, and to never judge a book — or mug — by its cover. Meaning and connection are pervasive and very special. Almost every order has a story. Those stories make my job fantastic.

How have you used your success to bring goodness to the world?

Fred: First, I think sustainable businesses are all doing good. If we give people good products, more meaning and better prices, while providing jobs and paying taxes — we’re doing good things! Second, I take a fairly libertarian view towards charitable things. If we pay people well and have a morally positive culture, I trust people to make their own decisions on how to spend money and time to help others. I’ve seen our employees and others do really great things. Personally, my family believes in tithing and supporting a number of causes including helping refugees, the environment, sustainable agriculture and education. I’m not a billionaire, and so have not been invited to the giving pledge, but I’m a strong supporter of its principles. The biggest reason I work so hard is to try to make as large of a positive change in the world as I possibly can. Working is how I fundraise, and would have retired by now otherwise.

What are your “5 things I wish someone told me before I Started my Business” and why.

Fred: 1. When you own a business, you have to let it own you too. You start a business thinking you can be your own boss and control your own time. But really, you’re never in control. Learn to embrace it. As the CEO, people talk to me about ideas while I’m in the bathroom, going out to my car, or while I have my hands full with a coffee mug and donut. At the same time, my own ideas follow me everywhere I go. So, I learned a long time ago not be in a hurry, and stop and listen.

2. Experience is that thing you get only right after you need it. Everyday, you’re going to be making decisions about things you know nothing about and have never done before.

3. Never be complacent when getting to know your customers. Always talk to them and know what they think. It’s going to change the way you market your business and how you think about your product.

4. There is no number four! If you’re making a list of more than three things, it’s too many. And if you’re expecting your employees to do that many things, something won’t get done. So don’t try to do more than three things at a time, because it just doesn’t work.

5. If you’re making a list of 5 things, it’s too many! But if I have to give five, here it is a mix of two and three: always keep learning. The only constant is change and whatever is a thing today, won’t be a thing tomorrow.

I have been blessed with the opportunity to interview and be in touch with some of the biggest names in Business, VC funding, Sports, and Entertainment. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this, or I might be able to introduce you.

Fred: Ariana Grande, because I would love to understand how she sits like that on a stool. No, really, most of the people I would love to meet are dead. Gandhi, Nietzsche, Frederick Douglas, Ben Franklin, Richard Feynman. I would aspire to be able to hold a conversation with any of these folks. If I had to choose someone living, I’d love to break bread with Chuck D, Bill Gates or Madhur Jaffrey. Otherwise, I’m just amazed with the people I have met and keep meeting.

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