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

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

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

Do people live up to our expectations?

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Let’s answer some reader mail… Piotr asks: Do you sign up to the adage that people live up to our expectations (both at work and in life? That’s a great question. And my answer today is different than it would have been a few years ago. Like many, I used to think people live up to… keep reading

Give 40, Take 0

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A manager’s job is to protect their team’s time and attention. Companies love to protect. They protect their brand with trademarks, their data and trade secrets with rules and policies, and their money with budgets, CFOs, and investments. Companies protect a lot of things, yet many of them are guilty of one glaring omission. Too… keep reading