Essays

Dec 7, 2020
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Listen to an audio take on this story on Capiche's SaaS Radio Hour.

“Software is dead,” declared Salesforce’s original marketing at the turn of the century. It was “the end of software,” software as we knew it anyhow, as the hopes and dreams of a generation went up in dot com bubble smoke. Maybe…

Nov 25, 2020
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“It’s a feature, not a product,” said Steve Jobs of Dropbox, after approaching founder Drew Houston about acquiring the file sync software.

Everything could be a feature, to Jobs. Cameras, alarm clocks, calculators—all features in the iPhone. Even Apple’s other products weren’t immune. The iPod was…

Nov 6, 2020
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The craziest app came out a month after the App Store opened to the public, charging $999 for a digital red gem and the text “I am rich.” It sold six copies and shut down the next day.

The next craziest app came out April 1, 2014. You’d tap a button to send your friend a one-word message: “Yo.”…

Oct 30, 2020
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Listen to an audio take on this essay on the SaaS Radio Hour’s podcast.

Flat-pack Ikea furniture can hardly rival the permanence of an oversized mahogany desk. But the mind’s a fickle thing, and you might value a desk you spent an afternoon assembling more than it’s worth.

That’s what a Harvard…

Oct 13, 2020
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“You should...commence the conversation by saying 'Hulloa!'” suggested the first phone book, New Haven, Connecticut’s The Telephone Directory. “When you are done talking, say 'That is all!', and the person spoken to should say 'O.K.'”

And so language changed, at least to start conversations.

As…

Oct 6, 2020
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It all started with a stack of books.

You don't just buy a desk on a whim, especially when you're not sure you can type reliably while standing. So, after one too many hours hunched over a desk, I enlisted my textbooks to help pay off the education they gave me. One stack to put the laptop at eye…

Aug 27, 2020
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It almost felt like common knowledge that software was increasingly expensive. Yet was it, really? Had the move from boxed software and one-time licenses to subscriptions and SaaS had actually resulted in higher prices, we wondered?

So last year we picked 100 popular business software, dug through…

Jul 31, 2020
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300,000 people are on Superhuman’s waitlist, while 95,000 requested a Hey invite before it launched—both in pursuit of a more productive email experience. Enough people paid Roam Research from $15/month to $500 for 5 years that they hit $1 million in ARR only 6 weeks after launching paid plans.

…

May 29, 2020
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Remember Google Wave?

Gmail had quickly become the most popular email service, enough that invites to the free service were bid up on eBay. Google Docs made modern collaboration possible, spooked Microsoft enough to build free, web-based versions of its Office tools. Google itself had become a…

Mar 17, 2020
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It wasn’t supposed to happen this way.

For those who have worked remotely for years—decades, even—it often started as a gradual process. We worked freelance first and figured out collaboration remotely on individual projects. That’s easy enough: One task, one set of deliverables, a deadline and a…

Nov 5, 2019
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When Google launched their online office suite with Docs and Sheets in 2006, feature parity with Microsoft Office wasn't the focus. Neither was a price tag of free, or cross-platform support by virtue of being a web app. Instead, Google focused on the pain of emailing documents back and forth to…

Oct 30, 2019
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Software’s not all that expensive when you buy one app for one person. It saves time and makes you money, and all’s well.

Then your team grows, and by the time you pay for G Suite, Slack, GitHub, and all your other work tools, software’s not such an innocent expense anymore. Pay $75 per person for…

Sep 23, 2019
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Free is a hard genie to put back in the bottle.

When Microsoft charged $999 for Office in 1990, little did they dream that 16 years later, their greatest competitor would be a free office suite from Google—along with dozens of small, often free apps that individually did many of the same tasks as…