Barrett Sheridan

Former technology editor at Bloomberg Businessweek. Knight-Bagehot Fellow at Columbia Business School.

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Options 101

Joining a startup? Here’s what you need to know about employee stock options

Hey! I just joined Jump.ly, a Google Glass-only social network for parachuting enthusiasts. I’m employee No. 4 and got 10,000 stock options. Can I put in my Tesla pre-order now?

Maybe you should ask your HR department a few questions first. Most new hires receive only cursory information about options, how they work, and what they could be worth; there’s no standard for communicating this information. Knowing the details of your options will be essential when you decide to leave Jump.ly and whether to exercise the options.

First, let’s define a few of the terms.

Option: An option is the right, but not the obligation, to buy stock at a pre-determined price. In plain English, an option is kind of like a bet with no downside, like when your cousin offers you $5 to snort wasabi. No harm if you turn him down, just...

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Data Visualization on a 4" Screen

To walk through San Francisco is to interrogate the lurid, sometimes brutal history of California’s settlement in the mid-nineteenth century. Each street has a story. Guerrero Street is named for Francisco Guerrero, a landowner and politician killed by a slingshot-wielding horseback assassin in 1851. Charles H. Gough, a local milkman, served on the committee that named many of the streets in 1855; in a bit of minor civic corruption, he named a major thoroughfare after himself and other streets after his sister, Octavia, and a friend, Steiner.

Noah Veltman, a San Francisco-based coder and designer, wanted to create an application to exhume this history. He envisioned a scrollable, zoomable map to surface the stories behind each street name. And because each tale is so intimately tied to geography, he wanted explorers to be able to access his map on-the-go. These days, says Veltman, “...

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Convertible Debt in Plain English

Finance is a bit like a secret society in that it likes to obscure commonsense ideas with intimidating language. Loans become bonds, bond insurance becomes credit default swaps. It’s a way to separate insiders and outsiders and raise a protective moat around in-the-know practitioners.

Anyone who reads TechCrunch has heard of the term “convertible note,” and knows it’s a common way for early-stage investors to bet on startups. But it’s a hard-to-grasp term, even for someone like me with an economics degree and a year of an MBA under my belt. I recently learned exactly what it does and why it’s used so frequently, and wanted to share that knowledge in a no-bullshit way. It’s not super complicated, but if you’re a 22-year-old Y Combinator grad building your first company, and investors start making offers, don’t you already have...

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Why Evernote Wins at Memory-Outsourcing

A year and a half ago I sat down with Evernote CEO Phil Libin for a wide-ranging chat. At the time, I was smitten with memory-decay algorithms, basically mathematical methods for learning new facts and concepts as efficiently as possible, and so of course I brought it up.

Phil didn’t have any immediate plans to include such a feature in Evernote. But he did have a really interesting response to the idea (which I’m paraphrasing because I can’t find my notes):

The hard part isn’t periodically reminding people of something they’re in the process of learning right now. It’s what happens in 5, or 10, or 20 years, when people have decades of memories and information stored in Evernote. It’ll be overwhelming. How do we smartly filter that information to remind people of what they already know when they need to know it?

It’s taken me a while...

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Did Tim O'Reilly Run Over Evgeny Morozov’s Dog?

My first thought on reading Evgeny Morozov’s dense, brilliant, and ultimately unfair takedown of Tim O'Reilly was: When did O'Reilly run over Morozov’s dog? Morozov’s Baffler piece is the academic equivalent of a flaming bag of shit on the tech publisher’s doorstep, a pie-in-the-face as O'Reilly strolls down the red carpet.

Plenty of others have summarized Morozov’s novella-length (over 16,100 words!) piece; i09’s Annalee Newitz does a decent job:

Morozov is worried that the memes of Silicon Valley will reshape our government’s future in a way that sounds democratic and progressive on paper – but will turn out, in practice, to create a nation whose citizens are impoverished and disempowered. Government will abdicate responsibility for providing its citizens with basics like roads, schools, scientific research, and health...

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