Who’s On First, What’s On Second, I Don’t Know’s on Third

My mom sent me this today. It’s still possibly one of the funniest comedy routines I’ve ever seen. I saw it for the first time as a little kid and I remember rolling on the floor laughing.

A brilliant demonstration of how complicated the English language can be, even in its simplicity. By about minute six, my guess is Abbott is feeling like most entrepreneurs do when they are tangled up in something.

It’s worth watching all eight minutes – it’ll put a smile on your face, regardless of how your day is going.

Long Form to Nano Form

As my newest book, Startup Opportunities: Know When To Quit Your Day Job, has begun shipping on Kindle (order now and give me feedback, leave a review) I’ve been thinking a lot about writing lately. Startup Opportunities took 18 months to write and most of the slowness was me, not my co-author Sean Wise. It was an interesting struggle to get done which I’ll write about at another time.

I love to write. It’s the way I put my thoughts together. I’ve never really understood the phrase “I’m thinking about it” – I never consciously sit and think, but when I’m writing my brain is often doing the job of thinking.

I also love to read. It’s the way I put my thoughts together and learn new things. I’ve never been an auditory learner. I remember sitting in classes at MIT, listening to the professor lecture, and understanding almost nothing. But then, when I sat down and read the course notes, or whatever reading material was assigned, it all became clear. I’m sure the verbal stuff entered my brain somehow, but it didn’t really turn into something I understood completely until I was able to sit and read.

Fortunately, I’m a fast reader. And after writing millions of words, I’ve become a fast writer. When I’m asked how I read or write so fast, I have a simple answer – practice.

I continuously read essays that talk about the end of books. The end of the publishing industry. How humans are reading less. Crap like that. While it makes for nice self-referential essays in magazines like The Atlantic, or books by authors about how Google is making us stupid, I think it’s all wrong.

I think the fundamental thing that is changing is the distribution of written information. This is nothing new – it’s been going on since the Egyptians created the writing systems 4,500 years ago. And, it is going to get really interesting in the next twenty years as humans become much more integrated with machines, as I’m completely ready to jack in to the Internet full-time.

When I think of the different forms I read and write, it ranges from what I call “the long form” (books) to “the nano-form” (tweets). On a daily basis, I consume books, essays (posts on Medium, magazine articles), blogs, emails, Facebook posts, Tweetstorms, and Tweets. While I don’t use Yo anymore, you can bring it all the way down to the human-nano level.

When I look at the activity in my Goodreads feed, it’s clear to me that the book is not dead. Many of the people I respect, follow, and have relationships with are deep thinkers and love to read – both for learning and recreation. Sure, the book is competing with a lot of other media types, but reading (and writing) seems to persist quite successfully.

Is the book really dead? In 20 years, will we still be calling them books, or will they be something else, in the same way that no one under the age of 10 knows what a record is.

Mentors 10/18: Hold Information In Confidence

As we continue deconstructing the Techstars Mentor Manifesto, today’s item is about keeping information confidential.

Techstars operates on a FriendDA concept. It’s not official, but it’s understood that the entrepreneurs are going to bare their soul, be completely open and transparent, and not ask anyone to sign anything. In exchange, mentors will hold information in confidence.

This can be tricky. It’s hard to know what is confidential, a secret, something someone is merely pondering, a brilliant new idea, something that conflicts with something else you know about, or, well, something that is going to make someone upset if it gets around.

There’s a simple approach to this. Use your judgement. If you are uncertain, ask the person who you got the information from.

We operate this way at Foundry Group also. We don’t sign NDAs. If you don’t trust us, don’t share something with us. If you don’t want us to know something, that’s fine. If it’s important to you that something be held in confidence, feel free to say so. But assume we are respectful, conscientious about what we can and can’t share, and fundamentally default to holding information in confidence.

It’s kind of that simple. Remember my fuck me once rule. It’s my responsibility to tell you that I’m unhappy with what you did and it’s your responsibility to own it. That generates a second chance. There is no third chance.

How To Deal With Email After A Long Vacation

Since I’ve had dealing with email on my mind recently, I thought I’d write about how to deal with email after a long vacation. Over the years, I’ve heard over and over again from people who never going on vacation or getting off the grid explaining that they can’t imagine doing this because they would be more stressed out when they return to all the email they have to respond to. I don’t think it has to be that way.

For context, I’m a huge believer on completely going off the grid for vacation. Amy and I have been taking a weekly vacation off the grid for 15 years. No phone, no email. Just the two of us. Given the pace of our lives and the amount of time we spend apart, it’s an awesome way to reconnect. There’s nothing quite like spending a week with your beloved on a periodic basis to remember why you love each other.

Whenever I’m off the grid for a week, I always come back to loads of email. I used to organize my trips from Saturday to Saturday so I’d have Sunday to go through all my email and catch up. That works, but ruins the last Sunday of the vacation. Then I shifted to Monday, so I basically scheduled nothing on Monday and just went through all my email during the day while getting back in the flow of things. That made for a shitty Monday and usually damaged my calm that had resulted from my week off the grid.

When Amy and I took a one month sabbatical in November, I tried something different. Here is my vacation reminder from that trip.

I’m on sabbatical and completely off the grid until 12/8/14.

I will not be reading this email. When I return, I’m archiving everything and starting with an empty inbox.

If this is urgent and needs to be dealt with by someone before 12/8, please send it to my assistant Mary (mary@foundrygroup.com). She’ll make sure it gets to the right person.

If you want me to see it, please send it again after 12/8.

My partners covered for me when I was gone and dealt with anything that was important. The three of them had each taken a month off before my sabbatical so we had a nice rhythm around this.

At the last minute I chickened out on archiving everything without looking at it. Instead, I just scanned through my inbox, archiving messages without responding to them. I didn’t save anything, even if it asked me to do something. I archived it just like I said I was going to. But I had some context around what was going on. It took me about three hours to get through the 3,200 emails I had waiting for me. Not surprisingly, when you don’t send any emails, you get a lot less.

On Monday morning (12/8) when I came back to the office, I had an empty inbox except for the emails that had come in since I did the scan (which I did on 12/6 – we traveled home on 12/7). It was unbelievably liberating. I sat down with each of my partners and went through things that had happened when I was away in companies I was on the board of. That took less than 15 minutes per partner. At lunch, I got caught up on the overall portfolio.

By Tuesday I was back in the flow of things and felt very calm and relaxed. My vacation mellow wasn’t harshed at all.

This approach works for any length of time. Amy and I took a five day off-the-grid vacation for Valentines Day week. Same drill, although this time I responded to a few emails that came in when I reappeared and did my scan. But I set the expectation that I wasn’t going to look at anything, so plenty of “resends” happened on Monday and Tuesday, which meant that folks who really wanted to interact with me took responsibility for it.

There’s something about taking control of how email interacts with you that is very satisfying. I’ve heard the complaint, over and over again, that email allows other people to interrupt your world. That’s part of the beauty of a low barrier to communication (e.g. just send something to brad@feld.com and it gets to me.) But it’s also a huge burden, especially if you want to engage back.

I’m always looking for other approaches to try on this, so totally game to hear if you have special magic ones.

The Magic of OtherInbox

I get 300+ non-spam emails a day. No matter how diligent I am at unsubscribing from stuff, I still get an endless stream of valid, opt-in email that I want to unsubscribe to. Google takes good care of my spam and they even jumped all over my complaints about their spam filtering, figured out the problem, and fixed it (thanks friends at Google). So, I’m not talking about spam, but all the rest of the stuff that I don’t need to see right away.

I’ve tried to use Google’s categories, but it doesn’t really work well for me. Others are emails I never want to see and want to unsubscribe from, but (a) it takes longer to do that, (b) trying to unsubscribe from a mobile client is painful, (c) many of my unsubscribes don’t seem to work (I just end up seeing the email again in a few weeks), and (d) the whole experience / UI is sucky.

Now, before you jump to “use a different channel than email”, recognize that I have also Slack, Kato, iMessage, Twitter, Facebook, Skype, and Google Hangouts open on my desktop with stuff hitting them all day long. Voxer lights up regularly on my iPhone, along with notifications from each of these apps. Channel proliferation has become a mess for me and one of the companies we are investors in is working on that problem earnestly.

Ultimately though I spend most of my time in Gmail especially given the amount of email I get from all different senders. It is unyielding – here’s an example from last week.

Email stats from last week

About 25% are emails that I do not need to see right away. Probably 10% are ones that I want to unsubscribe to.

OtherInbox’s Unsubscriber and Organizer solves both of these for me. Josh Baer, a long time friend and leader in the Austin Startup Community, was the co-founder. OtherInbox was acquired a few years ago by Return Path, which I’m on the board of. I used OtherInbox for a little while before and after the acquisition, but in one of my mad Gmail / Chrome plugin-performance-misery-slowdown-cleanup-fits I stopped using it.

OtherInbox folder list

Last fall, after playing the endless unsubscribe-to-clean-things-up-each-morning I decided to try OtherInbox again. I went all in this time. Within one week I was in email heaven.

Here’s how it works. If I want to unsubscribe to something, I simply label it “Unsubscribe” using Gmail labels and I never ever see it again. Then, OtherInbox constantly moves new emails that match certain criteria to folders. This happens automatically and in the background it figures out the organization of the emails.

I can adjust it if I want, but I’ve found that I spend almost no time adjusting it anymore. Typically, I have some unreads in there and they show up as unreads normally do in Gmail, so at the end of the day I just go to label:oib is:unread and take a quick look.

Give Unsubscriber and Organizer a try. I think you’ll find them as magical as I do.