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Sometimes, you go to one too many New York Tech Meetups or read yet another “Silicon Alley vs Silicon Valley” blog post and come away thinking: Techlandia is kind of a quixotically silly place.

When this happens, go spend an hour or so reading through Charlie O’Donnell’s blog, and then you will feel rosier. Many VCs have blogs that are smart and thoughtful, but Charlie’s advice on all things startup (funding , branding, pitching, the founder-vc relationship) is also personal and friendly and bombast-free. Also: kayak/softball/Mets enthusiasts: this is the place for you.

[sorta long side note]I met Charlie at a barbeque joint called Iron Works, just off the Colorado river in Austin, Texas. I’m not the neatest of eaters, and this was my first plate of Texas meat, so I probably didn’t make the best first impression. Then I invited him to the GroupMe party, not realizing he’d lead FirstRound’s initial investment in GroupMe, so I probably didn’t make the best second impression, either.

But no matter -- he still let me peek into his inbox. And it’s a pretty wild and crowded place, folks, so keep your seatbelts on and your elbows in.

First email service: Not counting Prodigy[1], tie between a very complex Lotus Notes account used for an internship at GM’s pension fund and an AOL account, both acquired in 1997, during his senior year of high school.

Current email service: all Gmail, and all accounts feed into one, because “there is no line between Charlie the Person and Charlie the VC.”

Email interface - desktop: Gmail web browser and the Chrome gmail offline plugin.

Email interface – phone: Switches between Apple’s mail app for composing messages and the Gmail app for searching, since the former sucks at search and the latter isn't fast in poor coverage environments.

3rd party apps: Rapportive, OtherInbox, and

Current unread count: 1800 -- “a failure,” he says. Usually he has between 200-1000.

Emails received in a day: not counting the notifications, which go to his Otherinbox, around 4-500.

Emails responded to in a day: between 20-33%.

Desktop vs phone usage: If he's responding on the day of, it's usually from his phone, and these are usually shorter than 2 sentences. Desktop is for batch emails.

Unique behaviors: In a word, filters: Charlie has filters for his investors, portfolio companies, emails with the word "intro" in them (which get priority), and auto-notifications from his public calendar app (these are a good filter for pitches). He also has certain emails come in automatically marked as read.

First checks email: Right after waking

Last checks email: Generally, before leaving the office--he'd rather stay late and read email there than bring it home  

Overload level: yellow

Email desires:

1. Ability to quickly sort through the unreads.

2. Ability to unsubscribe to emails from his phone offline, with one tap.

3.  Daily email stats, eg: how many emails he's received that day, how many he's responded to, the people he's interacted with, and response time stats.


1. The dialog service, not the band