The importance of sucking

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Lessons from a bruised leg… My leg looked liked this a few months ago: Gross. No, I didn’t get surgery. No, I was not mauled by a bear. I went snowboarding for the very first time over New Year’s. The experience was brutal, needless to say. I fell probably a hundred times. Over and over and… keep reading

Jobs to be done — Getting started

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If you don’t know me, Hi. I’m Nate. I took over as CEO of Highrise as we spun it off from Basecamp in 2014. It’s been an exciting project, but holy crap is it hard. Highrise is a simple CRM you can get your whole team on in a few minutes and it’s been around… keep reading

Can’t crack that programming problem? Go to sleep (or take a walk)

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Think back to the last time you had that really tough programming problem you couldn’t crack. If you’re like me, you may have spent a few hours trying to brute force a solution. Then, in despair and frustration, eventually you gave up for the night. And then the next morning, you wake up and the… keep reading

Screenshot? Ugh, you’re doing it wrong!

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A proper sharing feature has been part of iOS for years. It has a consistent, system-level UI that’s available from most any app with anything worth sharing and yet no one seems to use it. Well, no one but us geeks, right? Everyone else just takes screenshots—which require mastering an unintuitive multi-button press and a… keep reading

Web 3.0

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Whatever happened to Web 3.0? What was it? Did it ever happen? I’ve seen multiple attempts at definitions. Things about artificial intelligence. The semantic web. Social networks. One thing I remember about Web 2.0 was that 37signals (the original company behind Basecamp) was labeled as a company who was very “Web 2.0”. I’m not sure… keep reading

Google won’t be able to resist listening in on your conversations

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Mr Algorithm is always listening The advertising trial balloon from Google Home really shouldn’t have come as a surprise to anyone. Okay, perhaps, the linguistic contortions performed by Google’s PR rep to The Verge should have raised an eyebrow. I mean just listen to the bullshit drip from this one: This isn’t an ad; the… keep reading

The Richest Man In Town

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Illustration by Nate Otto Cullinan’s Stadium Club and Beverly Records sit next door to each other in the Chicago neighborhood of Morgan Park. The owners of the two businesses have been friendly since Dan Cullinan opened his bar and grill in 1989. But even Dan couldn’t imagine how John Dreznes of Beverly Records would rush in… keep reading

How to launch software changes without pissing people off

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Go the extra mile to avoid interruptions and protect your customers’ time. Software designers and developers are all about NEW. We like to experiment with far-out ideas and make shiny things. Our livelihood depends on it. We’re so addicted to NEW that sometimes it clouds our judgment. We love NEW and everyone else should too,… keep reading

Don’t accelerate your startup

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Once you’re onboard, you’re not getting off Selling 7% of a mere startup idea for tens of thousands of dollars, mentorship from Silicon Valley royalty, and the contacts that come with it seems like a no-brainer proposition. No wonder the mostly young, fresh-eyed recruits are lining up for that deal. But that’s because they’re not reading… keep reading