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99U's best entrepreneur idea of 2018, represented by a series of circles that represent new interpretations.

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From Creative Bridges to Copyright Cash Cows: 99U’s 10 Best Entrepreneurial Ideas

Entrepreneurial thinking was in the air this year, from bridging creativity and capital to scaling side hustles. We rounded up the best advice from 99U thinkers who have been there, won it all, failed big, and kept on coming back for more. 


A good entrepreneur mixes creativity, strategy, and smarts. From uncovering under-the-radar gems to the hard science of Gee whiz, how the heck do I price this?, we gathered some of the brightest ideas from 99U stories this year to help us put our entrepreneur thinking caps on.

Design Army co-founder Pum Lefebure in Design Army's new creative co-working space. Image courtesy of Design Army.

Design Army co-founder Pum Lefebure in Design Army’s new creative co-working space. Image courtesy of Design Army.

1. Create an experience.

Design isn’t just cosmetic fixes; it’s savvy business strategy that gets to the structural heart of a problem. When a real estate client asked Design Army to create a one-page magazine ad for its new condos, co-founder Pum Lefebure had a better idea: make your own magazine. The slick glossy profiles creatives and business in the developer’s neighborhood, with ads for the condos in the back pages. It’s a recurring win for both creative and client.

Metajive's Dave and April Benton deep in paperwork. Photographed by Franz Steiner.

Metajive’s Dave and April Benton deep in paperwork. Photographed by Franz Steiner.

2. Set a standard pricing formula.

Ask 10 people for their pricing strategies, and you’ll receive 10 different answers. Which is best for you? The one that works for you. So ignore what other businesses are charging or how much you think your client can afford to pay. Instead, focus on the value of you and your work. “We ask ourselves how much time will it take to do a good job, then multiply that by our hourly rate (cost + desired margin) and add in a 5 to 10 percent buffer for unexpected events,” says Metajive CEO and founder Dave Benton. “We use this principle no matter if the client is a 20-person company or a 2,000-person company.”

Lumi focuses on making the best looking packaging around, such as these bright orange shipping bags for Cotton Bureau.

Lumi focuses on making the best looking packaging around, such as these products for Cotton Bureau. Image courtesy of Lumi.

3. Search for opportunities where others aren’t looking.

“Usually, people starting businesses, and entrepreneurs in general, are very interested in looking cool and being cool people,” says Jesse Genet, co-founder of shipping supplies company Lumi. Instead of going for the glitter, ask yourself: What does everyone overlook? Packing tape, anyone?

4. Engage in creative hallucinations.

A designer is never executing the status quo. Good designers are always moving forward. Many people have great jobs, but they don’t change the way people do things; they don’t envision a different world. “Zero designers are just operating in the existing world,” says Jon Hirschtick, founder of computer-aided design software giant SolidWorks. “You have to see something that doesn’t exist. You have to engage in creative hallucination.” Visions and hallucinations look the same until you try to build them.

Blue Bottle Coffee founder James Freeman makes coffee in the early days of his company. Image courtesy of James Freeman.

James Freeman makes coffee back in the early days of Blue Bottle Coffee. Image courtesy of James Freeman.

5. Embrace your constraints.

Art is about constraints, right? When Blue Bottle Coffee founder James Freeman started out he had a cart and a 250-foot kiosk. Those constraints meant he couldn’t have a lot of extra stuff, so he had to be very pared down. And Blue Bottle’s hallmark design became recognizable for what is not there. “I don’t like things arranged on shelves, for example. Shelves are for books or dishes. They are a tool, not a decoration,” says Freeman. “After working on 40 cafes now, we mostly think about what shouldn’t be there.”

The World Character Summit in Hanyu, Japan. Photos by Chris Carlier, for his blog Mondo Mascots.

The World Character Summit in Hanyu, Japan. Photos by Chris Carlier, for his blog Mondo Mascots.

6. Make it cute.

This tenet sure doesn’t apply to all projects. But it’s hard to argue with the booming Japanese mascot market. “Simple, colorful, symmetrical designs tend to work best,” says artist Chris Carlier on what we can all learn from mascot design. “And don’t shy away from silly, absurd ideas—those grab the most attention.”

7. Don’t get sidetracked by other people’s best practices.

Having a lay of the land is important. But too often, overemphasizing industry averages, generalities, and best practices reveals a lack of trust in your own instincts. Remember, you’re the expert in the nuances of the problem you’re trying to solve. “Tasty little morsels of detail swim right in front of us every day,” says Jay Acunzo, author of Break the Wheel. “If only we’d use that information to inform our decisions.”

Radim Malinic's Book of Ideas is filled with his insights on the design life. Image courtesy of Radim Malinic.

Radim Malinic’s first Book of Ideas was so successful, he decided to publish a second volume. Image courtesy of Radim Malinic.

8. Treat your side hustle like your day job.

If Radim Malinic had treated his side hustle, the recently-published Book of Ideas, Volume 2, like a passion project, he’d still be writing today. Instead, he approached the project like a daily commitment. “There’s always an hour at the beginning or end of the day where you can do something for yourself,” he says.

A kitchen scene from Meow Wolf's immersive art installation that bridges the real and imaginary world. Photo courtesy of Meow Wolf.

Meow Wolf is an immersive art installation that bridges the real and imaginary world. Photo courtesy of Meow Wolf.

9. Build a bridge between creativity and capital.

Vince Kadlubek is a role model for turning a scrappy arts experience into a successful business with his art experience Meow Wolf. Now, he’s out to bridge the Grand Canyon-sized gap between creatives and business. The first step? “End this narrative that there’s such a thing as selling out. That’s what keeps creatives broke and powerless,” he says.

Delphine Diallo photographed holding boxing gloves outside in her Brooklyn neighborhood. Photo by Frances Tulk-Hart.

Delphine Diallo photographed in her Brooklyn neighborhood. Photo by Frances Tulk-Hart.

10. Copyright is your cash cow.

Photographer Delphine Diallo has plenty of prestige publications like The New Yorker and Esquire knocking on her door. But those shoots don’t pay all the bills. The real financial foundation of her business? The royalties that come in for usage of photos—on T-shirts, coffee mugs, and more—from big campaigns or celebrity projects. “I own the copyrights for my images for multiple years, and it can be renewed,” says Diallo. “These provide for me well beyond any editorial job.”

Emily Ludolph

Emily Ludolph writes about business, history, and culture. She has published in Quartz, Narratively, TED Online and Design Observer. She is the host of a live show and podcast called Dedicate It


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