What the best leaders do

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10 things I’ve tried to keep in mind as a CEO these past few years… “This is somewhat terrifying.” I remember thinking this when I became the CEO of Know Your Team back in January 2014. Sure, I’d started two companies beforehand — but one was with close friends, and the other was by myself. With Know Your… keep reading

I don’t have enough

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It’s been a rough week. We’ve been migrating our file storage for Highrise and you can imagine how difficult that is for a product running since 2007 with millions of users. And it wasn’t going that well. Fortunately, we had enough backup procedures in place to handle most problems. But still, on Thursday morning at… keep reading

Specific questions yield specific answers

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Specific questions are our most underrated management tool. Ask the right question… and you’ll learn that your company’s most valuable employee doesn’t feel challenged by her work and is thinking about leaving. Ask the wrong question… and you’ll hear the same employee tell you she enjoys the work environment and is confident about executing her… keep reading

Celebrate the web by using another browser than Google’s Chrome

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I like Chrome. It’s a great browser. But it’s not so good that it deserves to be the only browser. And that’s the unfortunate opportunity we, people browsing the web, are opening for Google by so overwhelmingly choosing to use it in face of the alternatives. And this is what we get by doing so:… keep reading

New file upload and browsing in Basecamp 3 for Android

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Summer brings 4 day work weeks at Basecamp, but that doesn’t mean the Android team takes a break. They just launched a new version of Basecamp 3 for Android, with an updated file browser to make attaching files to your Basecamp faster and easier. With the new file browser, you can attach an image directly… keep reading

The Business Cycle, Part 2

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Illustration by Nate Otto In 2010, as Worksman Cycles was emerging from the recession and ready to grow again, the maker of heavy-duty cycles saw an exciting opportunity to supply the bikes for New York City’s bike share program. But the city rejected Worksman’s proposal, and that disappointment lay the groundwork for the company to relocate… keep reading

Why I illustrate all our blog posts, as a CEO

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Lately, I’ve been getting asked more frequently: “Claire, do you illustrate your own blog posts?” The answer is, “Yes.” To date, I’ve written hundreds of blog posts. With the exception of a few (where I’ve used a photograph as the main image instead), I’ve illustrated each one myself. I’m not a professional artist by any… keep reading

How much should I charge?

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The Chicago Botanic Garden is large garden and tourist attraction that opened to the public in 1972. (It’s a funny name though since it’s actually in a suburb of Chicago called Glencoe.) Besides the name, one thing I find interesting about the Chicago Botanic Garden is how they charge. Most museums in Chicago, like most… keep reading