Multiple times a day, someone in my network asks if I’ll make an intro to someone else. I’m almost always happy to do this and, if not, I will explain why.

I like to do opt-in intros, where I ask the person on the potential receiving end of the intro if they are open to the intro. Most of the time people say yes. Sometimes they say no. Very occasionally they don’t respond to me.

In the past, I’ve written posts about the best way to do this, at least from my perspective (and for me). However, as the number of requests of me increases, the ease and clarity by which people ask for the request has gone down.

So, here’s a new post on the topic, with simple directions that both (a) help make it easy for me, and (b) in my experience, make the ask a lot clearer and easier for the person the receiving end of the request to say yes to.

For the email title, do something like, “Intro to for ”. For example, if you are the CEO of Xorbix and you want an intro to GiantBigMonsterCompany, title the email “Intro to GiantBigMonsterCompany for Xorbix”

Write the email “to me” but make most of it about you. Start with something like “Brad, thanks for the offer to intro me to someone at GiantBigMonsterCompany.”

Then, quickly follow with the ask in another paragraph. “I’m interested in talking to GiantBigMonsterCompany about sponsoring the Xorbix conference in July for underrepresented founders.” Include a sentence describing the “why” such as “This is a great opportunity for GBMC to get exposure to an audience of diverse founders.”

Next, write up to three paragraphs, with links, about Xorbix and the specific activity you are addressing

End with whatever you want, including a repeat (in slightly different words) of the ask.

I’ll then forward it with an introduction from me to add credibility and ask if they are willing to connect with you, or ask them to forward on to the right person in the organization to make the connection.

They will either reply with Yes, forward me on to someone else in the organization to see if they are game, say No, or ignore me. The Yes / forward happens about 80% of the time, so you’ll usually get the intro and it’ll have context. And, for me, it’ll take me 60 seconds to do it, rather than a few minutes to put a thoughtful email together.

I got the following note from a friend this morning.

Hey. Over the past 6 to 12 months, I seem to be getting more requests from individuals in the City-1, City-2, and City-3 asking for introductions to you.
Curious as to your preference in how to handle some of these.

Many words on the web have been written about double opt-in email intros. This is the best and simplest way when you know the person asking for the intro and think the intro would be a good one.

To make the double opt-in easy for you to do:

• Have the person send you something to forward to me.
• Forward it to me and say “I vouch for this person” (or any other context you want to provide). Game for an intro?
• If I say yes, then connect us.

But, how about the situations where you don’t really know the person. In that case, someone is asking you to do work and use some social credibility in a situation where you don’t really know how much to provide.

If you don’t know much about the person, simply say “I think Brad is pretty easy to reach – his email is public – just send him a note.”

If you think the person is interesting and want to help, simply give out my email. I already get hundreds of random emails a day. I like getting them because there’s occasionally magic in them, so rather than fight it I just let it be part of my life.

It’s 2018. I’m still an incredibly heavy email user. It’s the primary tool in my workflow and has been since the early 1990s. I’ve tried a lot of different things over the years, but always come back to email.

I’ve been a Gmail user for almost a decade. While I’ve tried client-side apps, Gmail in Chrome has been the only thing that has stuck for me. I’ve also tried many of the iOS email apps and always end up back at Gmail for iOS.

Until now.

An increasing number of people in my world have been using Superhuman so I decided to give it a try. I was skeptical that it would capture my attention beyond a day. Two weeks later it is, in fact, superhuman. I’m using the Chrome app and the iOS app as my primary email clients.

The other tools I have in my email workflow are SaneBox, Todoist, Notebene (which recently replaced Captio), and FullContact. As a result of Superhuman, I eliminated TextExpander from the mix. The one limitation of Superhuman that causes me a little pain is lack of direct integration with FullContact, which would make managing my address book better.

I didn’t realize how sluggish Gmail on Chrome is, even on a 225Mbps connection (which is what my office is clocking in at this morning.) And, at home, where I often see 3Mbps at high peak usage times, it’s a dream. But, that’s a tiny part of the speed. The big change is that I keep my hands on the keyboard 100% of the time. While I’ve been a heavy Gmail keyboard user, it turns out that you need the mouse for a bunch of Gmail things. Superhuman has turned them all into either keyboard commands, a slightly different workflow, or a “snippet” that lets you create your own compound shortcuts.

I never thought I’d recommend a web-based email client that costs $30 / month, but Superhuman is worth every penny of it. I wish I was an investor, but I guess I’ll live with being a Superhuman user.

As I’m already getting lots of out of office messages for people taking this week off, I thought I’d revisit an approach to how to deal with email after a vacation.

In 2011, Josh Kopelman of First Round Capital came up with what, at the time, was what I thought was the best email vacation auto-responder in the history of email. Now, I have no idea if Josh invented this, but I’m going to give him credit for it.

I evolved this in 2014 when I took a one-month sabbatical. If you ever send me an email when I’m on my quarterly one week off the grid vacation, you now get this.

I’m checking out for a vacation until [date]. I’ll be completely off the grid.

When I return, I’m going to archive my inbox so I’ll never see this email. If you’d like me to read it, please resend it after [date]+1.

If you need something urgently, please email [my_assistants_email_address] and she’ll either help you or get you to the right person at Foundry Group to give you a hand.

On [date]+1, I usually get around 50 emails (in addition to my usual email flow of 500 daily emails) that are resent to me. That’s only 50 to respond to, instead of the roughly 3,000 emails I get each week.

It appears that The Atlantic has caught up with this thinking in The Most Honest Out-of-Office Message. I thought the article was fascinating, both in how the writer addressed the issue, but also in the intellectual and emotional tension around it.

Does it make you nervous to think about “Selecting All” on your existing inbox and archiving (if Gmail) or deleting (if Outlook)? While some of my friends do it periodically – as a result of pain or just to get a fresh start on a new year, I like to do the equivalent every quarter when I get back from a full week of an off the grid reset.

Josh – it was a while ago, but thanks for the inspiration. And, for those of you on vacation this week, I hope you aren’t reading this.

Unlike the person with a similar slogan, this one is highly accurate. Sanebox does indeed make email great again.

I’ve been using email since 1983. I started with MH and Rmail, then cc:Mail, then Microsoft Mail, with Compuserve mixed in. Eventually I ended up using Pine for non-Windows stuff and Outlook for Windows stuff. For a while. About seven years ago I switched to Gmail and never looked back.

Over the last seven years, I’ve tried a bunch of different add-ons and plug-ins and whatever you want to call them to try to clean up my inbox. As investors in Postini, I was able to eliminate my spam problem early on. But I struggled endlessly with bacn. I get 500+ emails a day so the bacn is intolerable in my main email flow and ends up getting ignored, rather than read later.

So I’d go through weeks of unsubscribe fits, where I’d try to mash out my misery by unsubscribing to things I didn’t want. Often, this just resulted in more bacn, sometimes from the same senders but often from others. I once again would go through another cycle where I’d try a different unsubscribe tool, but I’d always end up with better, but not good enough.

Over Memorial Day weekend, I decided to try Sanebox. My partner Seth has used it for a while and several other people I know swear by it. I tried it when it first came out (as one of my endless efforts to tame my inbox) but it didn’t satisfy me then.

This time – about a month later – I can definitively state that Sanebox is awesome. Not sort of awesome. Extremely awesome. It should consider running for president.

Magic trick #1: @SaneBlackHole: If I want to never see a piece of bacn again, I just label it @SaneBlackHole by typing v. Gone, forever. Anything from the sender never ever shows up in my inbox again, kind of like how Ramsay Bolton will never show up in Game of Thrones again.

Magic trick #2: @SaneNotSpam: I trust Gmail’s spam filter so I never, ever look in my spam folder. But Sanebox does look there for me because it knows not to trust it as much as I do. It finds at least one piece of NotSpam every day – sometimes as many as five pieces. Some of the NotSpam is amazing – on Friday a distribution notice from a VC fund I’m an investor in showed up there.

Magic trick #3: @SaneLater and @SaneNews: Sanebox automagically figures out which things I can look at later. It also figures out which email is a newsletter of some sort. It’s easy to adjust these if it gets it wrong, or label an email in my inbox with one of these labels and it then becomes one of these forevermore. At least 20% of my daily email ends up in one of these folders which I can then process once a day.

Within 30 days, with almost no effort, the signal in my inbox has reached about 99%. I read through notifications and news once a day. The crap that I don’t really want shows up once in SaneLater or SaneNews, I relabel it SaneBlackHole, and it’s gone forever.

Suddenly, my inbox is remarkably clean, useful, and free of noise. Thanks Sanebox!

Before you have an allergic reaction to the title of the post and respond with “you are stupid”, bear with me for a second as I set up the problem.

I’ve been a heavy Slack user for at least six months (probably closer to nine). We started using it internally at Foundry Group and then I joined a number of Slack instances of companies that we are investors in. For at least three months, I joined a number of relevant channels for each organization and tried to participate. I use Slack on the Mac primary so I used the left side bar to have multiple teams active, tuned my notifications so they weren’t overwhelming, and engaged as best as I could. I tried to post on Slack when I had an issue with the company – usually around a product – that needed to be communicated to a group instead of one person. And, for a few of the CEOs, we used Slack as our primary DM channel.

I hit the Slack wall about a month ago and stopped regularly engaging with the organizations other than Foundry Group. There is a long list of functional issues with how Slack handles things across orgs that makes using it this way a burden that suddenly felt worse to me than email. I could go through them and I expect Slack will eventually address some of them since I can’t imagine that I’m the only person in the world struggling to try to deal with Slack across 15 organizations, but the thing that really perplexed me was a new phenomenon that I noticed a month or so ago.

I’m increasingly being invited to other Slack groups of curated people.

This hit me in the face over the weekend when I was invited to a new Slack group by someone well-known. It’s a fascinating group of randomly connected people who ramped up a handful of channels over the weekend. I stayed on top of it until Monday morning and then was swept away in my normal week.

I just went and checked it again. There are over 60 members, but there were less than 30 new Slack messages since the last time I checked. Most were in one channel. As I skimmed it, I thought to myself that this would have been just as effective, or possibly more effective, as a typical group email list. And, since I do most of my group email lists in Google Groups, they are easily searchable and archivable, so the archive/search argument goes away away immediately.

As the amount of time I have to spend engaging with Slack increases, it suddenly feels more ponderous. And, when I started thinking about it in the context of the very active Foundry Group CEO list, it felt much less effective to switch this to a real time channel, as very few of the interactions necessitate real time.

So – I’m trying to get my mind around the value of Slack instead of an email list for large, cross-organization communication. Other than “it’s a new thing”, what are the foundational benefits of it. If you are someone engaged in a large, cross-organizational Slack group, now is the time to weigh in and give me a clue.

There are two common email conventions in my world that I use many times a day in Gmail. I don’t remember where either of them came from or how much I influenced their use in my little corner of the world, but I see them everywhere now.

The first is +Name. When I add someone to an email thread, I start the email with +Name. For example:

+Mary

Gang – happy to have a meeting. Mary will take care of scheduling it.

Now, why in the world can’t gmail recognize that and automatically add Mary to my To: line? If I needed to do “+Mary Weingartner”, that would be fine. Gmail is supposed to be super smart – it should know my address book (ahem) or even my most recently added Mary’s and just get it done.

The other is bcc: Whenever I want to drop someone from an email chain, I say “to bcc:” For example:

Joe – thanks for the intro. To bcc:

Pauline – tell me more about what you are thinking.

Then, I have to click and drag on some stuff in the address field to move Joe from the To: line to the bcc: line.

Dear Developers Working On Email Clients Of The World: Would you please put a little effort into having the email client either (a) learn my behavior or (b) Add in lots of little tricks that are common, but not standard, conventions?

Here’s a perplexing thing to ponder.

After trying virtually every email configuration on iPhone and Android devices, the best experience that I have had so far is using Microsoft Outlook on my Apple iPhone to access Google Gmail.

I’ve been using Outlook on my iPhone for the past few months. I’ve tried several times to go back to Apple Mail, but it is impossibly bad when compared to Outlook. I’ve also tried using the Google iOS Gmail client, which – while better than Apple Mail – is still very klutzy at certain things.

I know that Microsoft Outlook is really Acompli rebranded at Outlook, but in the eight months since the acquisition the product has continued to get better and better.

Go figure.

An increasing number of companies that I work with are using PGP to encrypt certain email. While they are comfortable sending a lot of email unencrypted, there are periodic threads that different people want to have encrypted for a variety of reasons, some rational and some not.

Each company is dealing with this a different way. Suddenly I find myself managing a bunch of public keys in different PGP tools on different computers. I started by going with the recommendation of each company and predictably found myself managing multiple solutions that sort of worked some of the time.

Last night I was on a hangout with one of the CEOs trying to troubleshoot the problem we were having with the implementation his company was using. After 15 minutes of fighting with a Chrome plugin, we gave up. Of course, when I went to a different computer, it worked just fine.

This seems like such a simple thing for Google (and Yahoo and Microsoft) to build into their email clients, especially the browser based ones. Keep the keys locally (or even in Dropbox or iCloud). Encrypt and decrypt from within the browser. Only transmit encrypted email. Only display the decrypted email.

Why hasn’t this been done yet? Am I missing something obvious?

Amy and I had a wonderful week off the grid in Paris. No phone, no email from Friday night 5/8 when I boarded the British Airlines flight in DIA until Friday morning 5/15 when we decided to turn stuff on and just lay around the hotel all day getting reading to go home.

I’m always fascinated by the email patterns I have when I’m off the grid for a week. I almost always go off the grid late Friday or Saturday morning so there’s the weekend lull followed by an intense flurry on Monday. By Tuesday my regular emailers have seen that I’m off the grid and their pattern of copying me slows down, but doesn’t stop completely. The emails then become more random.

By Wednesday, I’m getting three kinds of email.

1. #Important: Important stuff from people I know that I’m being copied on.
2. #New-Known: Stuff from people I know who didn’t email me earlier in the week.
3. #Random: Stuff from people I don’t know.

#Important and #New-Known tend to have similar tones. They are things for me to respond to, send to someone, make a decision around, or acknowledge receipt of information. Occasionally they require me to do something, but the action requested rarely takes more than five minutes.

#Random is completely different. Almost 100% of the #Random email has a specific request for me. These requests are often for meetings, phone calls, interviews, or speaking engagements. Some of them are specific sets of questions about a topic while others are long essays that never really get to the punch line, but clearly are begging to get to a question of some sort. Some are requests for introductions. And others are direct asks for financing.

This trip, when I went through my email upon my return, I left all the #Random ones for last to process. I had over 200 of these. This time I responded to all of them, but it wasn’t very satisfying. It took about four hours on Sunday and when I was done, I felt relief to be done, but when I reflected on it, I didn’t feel like I ended up with any new knowledge. That was disappointing as processing four hours of email to result in zero learning mostly just sucks, at least for me.

In this case, I packetized appropriately. Rather than getting bogged down in the stuff I needed to do while getting worn out by stuff that wasn’t that important to do, I only responded to stuff in #Important and #New-Known, ignoring the rest until I was completely finished with these categories. I think took a break and dealt with the rest later when my headspace was clearer.

As I sit here, I wonder why I responded to the other 200 #Random emails. I have a long-standing self-identity of responding to all emails that I get. For some reason, that’s important to me, but I’m no longer really sure why. It’s not satisfying in any way and the signal to noise ratio, or at least the value to non-value ratio, is way out of control at this point.

I guess I have something new to ponder in therapy. At least something good came out of responding to the 200 emails.

A few days ago, David Brown at Techstars wrote a great post titled “Staying Organized with Workflow” about how he stays organized. Brown and I work across the hall from each other and interact regularly. Often he’ll send me a note about something and I’ll just wander over and talk to him. He’s always available, super responsive on email, and very good at having a three minute meeting that results in a decision.

There was one thing in his approach that was something I used to do a long time ago, but stopped doing when I started using Gmail.

“Email Order. I process my email from oldest to newest. Yes, I cheat sometimes and answer a new one, but I try not to. It’s harder in Gmail because you can’t sort chronologically, but I just start at the bottom.”

A long, long time ago, in a galaxy far far away when I used Outlook, I processed my email in chronological order – oldest at the top. Gmail doesn’t let you reverse the sort order from newest at the top, so I just got out of the habit of this. But when I get behind on email by a few days and end up with 100 or more to grind through, I always go to the bottom and work backwards.

When I saw Brown’s note, I thought “duh.” Often, I have an almost empty inbox (as I do now – there is literally one message in it – read, but not responded to – right now.) So, even when there are 17 brand new emails, just clicking on the bottom one and reading backwards works just fine. In fact, it’s even better in the current world than my previous Outlook galaxy because of conversation mode.

Unlike Brown, I don’t use tasks or filters. I find that when I move things to a task list, I’m literally exiling them to the land of never-get-done. The only exception is longer form writing that is not urgent, which I just star in Gmail, archive, and periodically grind through my starred folder.

Regardless of the process you use, contemplate reverse the order of response from oldest to newest. If you aren’t going to do something with an email, just archive or delete it – don’t let it sit there. And, if you want some additional good tips, go read Brown’s post Staying Organized with Workflow.

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.

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.

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.

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.

I try to respond to all of my emails. I’ve always been like this – it’s just part of my value system. I used to be annoyed by other people who don’t, but I let go of that emotion a long time ago. But I still try to respond to all of my emails. A big hint, which is the reason for this post, is to ask specific questions if you want a real response.

Part of my morning drill is to systematically go through all the emails from the previous night. I usually end up at close to – or at – inbox zero when I finish this drill. Over the course of the week I get a little behind on non-urgent stuff so I end up responding to them over the weekend.

The result is a lot of what I like to call cliche loops. Here’s an example of the “will you look at our business, no, will you make a referral” loop.

Fortunately I use Yesware so I can respond quickly via templates I’ve already set up. Here’s how the more detailed conversation goes:

Entrepreneur: Happy New Year!  Attached is the our BP. Please let me know if you are interested to talk.

Me: Thx for reaching out again. I took a look – I don’t think it’s something we’d be into investing in but hope to run into you at anonymous-place at some point.

Entrepreneur: Thanks for the quick reply. Can we apply for the techstars?

Me: Of course!

Entrepreneur: Thanks for the advice. If you are willing, can you please comment on our BP? We wish you can be our advisor.

Me: I can’t be “an advisor” in any formal way. I’m also not part of the selection process for Techstars so I encourage you to just apply.

Entrepreneur: Thanks. We understand. You turned down our BP almost right away. So we are really appreciated if you can tell us what we can improve, or whats wrong there.

Me: I wrote a post about saying no in 60 seconds a while ago – https://feld.com/archives/2009/06/say-no-in-less-than-60-seconds.html. Your overview is ok – just not something I’m into.

Entrepreneur: Thanks for the detailed message. Do you have any other investors that you can point us to?

Me: Re: Asking for a referral – I wrote a blog about this a while ago – I hope it makes sense. https://feld.com/archives/2007/11/dont-ask-for-a-referral-if-i-say-no.html

Now, I’m not try to be an asshole with my responses. I’m just trying to get through one of “yet another email I’m not interested in” and be polite to the sender. If the entrepreneur had asked me any specific questions about his business, I would have tried to answer it or said “sorry – I have no clue” if I have no clue. But all of the questions are of the “please engage more with us” kind. Even the most specific question “So we are really appreciated if you can tell us what we can improve, or whats wrong there.” is painfully generic.

I realize that part of the reason I’m writing the book Startup Opportunities is so that I can point people like this at it. I get between one and five emails like this a day and have for a long time. I’m happy to get them – I just wish I could help more.

Lately, I’ve been struggling to figure out the best way to have expanding email groups. I’ve tried all the obvious stuff and nothing is satisfying to me.

Historically, I’ve just used Google Groups. That’s great for things like the Foundry Group CEO list, where we control the list, but then we have to host it at a @foundrygroup.com domain.

For the Colorado CEO Jobs list, we were using Yahoo Groups for a while. Even with the new upgrade last year I find the UX to be terrible so I recently moved it over the Google+. Now I’m hearing complaints about not getting the emails which usually results from notifications being turned off, but you wouldn’t know that unless you were paying attention. And, if you don’t have a Google+ account, you can’t be on the list.

I tried Facebook Groups for another group – it had zero engagement.

What do you use? Any suggestions for me getting out of hell?

I woke up this morning to another wave of holiday email cards. I had over 50 of them this morning. Yesterday I probably had at least 50 – by the end of the day it was likely over 100.

STOP! UNSUBSCRIBE.

I’ve never really understood the physical holiday card thing. I think it’s a secret ploy by the US Government to keep the USPS in business. I used to get a lot of Merry Christmas cards, which just annoyed me since I’m jewish and don’t celebrate Christmas. The world has become more politically (or religiously) correct so these are now Happy Holiday cards.

Amy likes these so you can keep sending the physical ones to us, especially if they have a nice photo of you or a story about what you did this year. But please stop sending the email ones to me.

Do a holiday video instead. Like one of these.

or

Love,

Brad “I’m only a little grinchy this year” Feld

I turned 48 on December 1st. I took a week off the grid (from the Wednesday before Thanksgiving until the Wednesday after my birthday) – part of my quarterly off the grid routine with Amy. We had a very mellow birthday this year, spent it with a few friends who came to visit us in San Diego at the tennis place we love to hide at, and basically just slept late, played tennis, read a lot, got massages, ate nice food, and had adult activities.

I returned to an onslaught of email (no surprise) which included a long list of happy birthday wishes. I had 129 happy birthday wall posts and about 50 LinkedIn happy birthday messages.

As I read through them, I was intrigued and confused.

• The Facebook wall posts were nice – almost all said either “happy birthday” or “happy birthday + some nice words.” I received one gift via Facebook (a charitable donation – thanks Tisch, you’ve got class!) Ok – that felt pretty good.
• The emails were mixed. Many of them were like the Facebook wall posts. A few of them were online cards. But about 10% of them asked me for something, using the happy birthday message as an excuse to “reconnect.”
• About 50% of the LinkedIn messages were requests for something. The subject line was “Happy Birthday” but the message then asked for something.

I decided not to respond to any of them. There were a few emails with specific stuff that I wanted to say, but the vast majority I just read and archived.

I found myself noticeably bummed out after going through the LinkedIn ones. I woke up thinking about it again today, especially against the backdrop of reading Dave Eggers awesome book The Circle (more on that coming soon.)

I’m an enormous believer in the idea of “give before you get.” It’s at the core of my Boulder Thesis in my book Startup Communities: Building an Entrepreneurial Ecosystem in Your City  and how I try to live my personal and business live. Fortunately, many of the people I am close to also believe in this and incorporate it into the way they live.

When processing my birthday wishes, especially the LinkedIn ones, there was very little “give before you get.” That’s fine – I don’t expect that from anyone – it’s not part of my view of an interaction model that I have to impose it on others. But I was really surprised by the number of people that used my birthday as a way to “get something” without “giving something” other than a few words in a social media message.

This confused me. The more I thought about it, the more I was confused, especially by the difference between email, Facebook, and LinkedIn. When I tried to organize my thinking, the only thing I could come up with was that email was “variable”, Facebook was “generic”, and LinkedIn was “selfish.” I didn’t love these characterizations, but this prompted me to write this post in an effort to understand it better.

Oh – and the best thing I got electronically for my birthday was from Andrei Soroker via a different channel – Kato.

I’m going to ponder the “culture of different communication channels” more, but I’m especially curious if anyone out there has a clear point of view on the different cultures between email, Facebook, and LinkedIn. Feel free to toss Twitter in the mix if you want.

Today, Return Path launched three new products and reframed its business as “email intelligence.” Matt Blumberg, Return Path’s CEO has an excellent post up titled Email Intelligence and the new Return Path.

Return Path is an extraordinary company that I’m proud to have been involved with for the past 12 years. At our board meeting last week, Matt gave me and Fred Wilson our 12 year anniversary gift – a pair of red Return Path-branded Adidas sneakers. I still vividly remember the phone call Fred and I had where we cut a deal to merge two nascent companies – Veripost and Return Path – in what became Return Path. We cut a deal in 10 minutes – I offered up a 50/50 merger and Fred suggested he wanted a little more since Return Path had raised 3x the money Veripost had. I responded with “how about 55/45” and Fred said “it’s a deal.”

Twelve years later Return Path is company with over 300 people, major offices in New York, Boulder, and the Bay Area, and other offices around the world. It has created and leads an entirely new category we call Email Intelligence. In 2008, after plenty of forward progress as well as some twists and turns, we finished divesting several older lines of business and focused the company entirely on a new category we created called “Email Deliverability.” As we grew, we expanded the definition to the point where the word “deliverability” only covered a subset of what we did, hence the creation of the category of “Email Intelligence.”

Matt says it extremely well in his post:

“Our solution to these problems is email intelligence. Email intelligence is the combination of data from across the email ecosystem, analytics that make it accessible and manageable, and insight that makes it actionable. Marketers need all of these to understand their email performance beyond deliverability. They need it to benchmark themselves against competitors, to gain a complete understanding of their subscribers’ experience, and to accurately track and report the full impact of their email programs.” 

I’ve been investing in and around email since my first email-related investment in 1994 in a company very creatively named “Email Publishing” which was the very first email service provider. Since then I’ve had a number of investments in email companies including Critical Path, Postini, and SendGrid. I’m psyched with the success and leadership of Return Path to date, love working with everyone at Return Path, and look forward to continuing the journey as we work to ensure that inboxes contain only messages that users want.

tl;dr – Yes.

I’m on the all@company.com list for a number of the companies I’m on the board of. CEOs and entrepreneurs who practice TAGFEE welcome this. I haven’t universally asked for inclusion on this list mostly because I hadn’t really thought hard about it until recently. But I will now and going forward, although I’ll leave it up to the CEO as to whether or not to include me.

In an effort to better figure out the startup board dynamic, I’ve been thinking a lot about the concept of continual communication with board members. The companies I feel most involved in are ones in which I have continual communication and involvement with the company. This isn’t just limited to the CEO, but to all members of the management team and often many other people in the company. Working relationships as well as friendships develop through the interactions.

Instead of being a board member with his arms crossed who shows up at a board meeting every four to eight weeks to ask a bunch on knuckleheaded questions in reaction to what is being presented, I generally know a wide range of what is going on in the companies I’m on the board of. Sure – there are lots of pockets of information I don’t know, but because I’m in the flow of communication, I can easily engage in any topic going on in the company. In addition to being up to speed (or getting up to speed on any issue faster), I have much deeper functional context, as well as emotional context, about what is going on, who is impacted, and what the core issue is.

Every company I’m involved in has a unique culture. Aspects of the culture get played out every day on the all@company.com email list. Sometimes the list is filled with the mundane rhythms of a company (“I’m sick today – not coming in”; “Please don’t forget to put the dishes in the dishwasher.”) Other times it’s filled with celebration (“GONG: Just Closed A Deal With Customer Name.”) Occasionally it’s filled with heartbreak (“Person X just was diagnosed with cancer.”) Yet other times it is a coordination mechanism (“Lunch is at 12:30 at Hapa Sushi.”) And, of course, it’s often filled with substance about a new customer, new product, issue on tech support, competitive threat, or whatever is currently on the CEO’s mind.

As a board member, being on this list makes me feel much more like part of the team. I strongly believe that board members of early stage companies should be active – and supportive – participants. My deep personal philosophy is that as long as I support the CEO, my job is to do whatever the CEO wants me to do to help the company succeed. Having more context, being part of the team, and being in the flow of the all@company.com communication helps immensely with that.

There are three resistance points I commonly hear to this:

1. “I don’t want to overwhelm my board members with emails.” That’s my problem, not yours, and the reason filters were created for people who can’t handle a steady volume of email. If you are a Gmail user, or have conversation view turned on in Outlook, it’s totally mangeable since all the messages thread up into a single conversation. So – don’t worry about me. If your board member says “too much info, please don’t include me”, ponder what he’s really saying and how to best engage him in continuous communication.

2.”I don’t want my board members to see all the things going on in the company.” That’s not very TAGFEE so the next time you say “I try to be transparent and open with my investors”, do a reality check on what you actually mean. Remember, the simplest way not to get tangled up in communication is just to be blunt, open, and honest all the time – that way you never have to figure out what you said. If you don’t believe your board members are mature enough to engage in this level of interaction on a continual basis, reconsider whether they should be on your board.

3. “I’m afraid it will stifle communication within the company.” If this is the case, reconsider your relationship between your board members and your company. Are you anthropomorphizing your board? Are you shifting blame, or responsibility to them (as in “the board made me do this?”) Are you creating, or do you have, a contentious relationship between your team and the board? All of these things are problems and lead to ineffective board / company / CEO interactions so use that as a signal that something is wrong in relationship.

Notice that I didn’t say “all investors” – I explicitly said board members. As in my post recently about board observers, I believe that board members have a very specific responsibility to the company that is unique and not shared by “board observers” or other investors. There are plenty of other communication mechanisms for these folks. But, for board members, add them to you all@company.com list today.

In December I wrote a post titled It’s Not About Having The Most Friends, It’s About Having The Best Friends. Since then I’ve been systematically modifying my social networking behavior and cleaning up my various social graphs. As a significant content generator in a variety of forms (blogs, books, tweets, videos) and a massive content consumer, I found that my historical approach of social network promiscuity wasn’t working well for me in terms of surfacing information.

I made two major changes to the way I use various social networks. I went through each one and categorized each on three dimensions: (1) consumption vs. broadcast and (2) public vs. private, (3) selective vs. promiscuous. These are not binary choices – I can be both a content consumer and a broadcaster on the same social network, but I’ll use it differently depending where on the spectrum I am.

For example, consider Facebook. I determined I was in the middle of the consumption/broadcast spectrum, public, and selective. With Foursquare, I determined I was closer to broadcast and private and very selective. With LinkedIn, I was 100% broadcast, public, and promiscuous. With Twitter, I was similar to Facebook, but with a much wider broadcast and promiscuous. With RunKeeper, very strong on broadcast, public, but selective.

I then looked at the tools I was using. Yesterday I noticed Fred Wilson’s email The Black Hole Of Email and it reminded me that I view email as my primary communication channel for broad accessibility (I try to answer every email I get within 24 hours – if it takes longer you know I’m on the road or got behind) and often respond within minutes if I’m in front of my computer. But I’ve worked very hard to cut all of the noise out of my email channel – I have no email subscriptions (thanks OtherInBox), I get no spam (thanks Postini), I run zero inbox (read and reply / archive immediately), and am very selective with the notifications I get via email (i.e. I check Meetup.com daily, but the only email notifications I get are for Boulder Is For Robots.) As a result, I find email manageable and a powerful / simple comm channel for me.

Tuning each social network has ranged from trivial (15 minutes with RunKeeper and I was in a happy place) to medium (Foursquare took an hour to clean up my 800+ friends to 100-ish) to extremely painful (going from 3000 Facebook friends to a useful set seemed overwhelming.) I decided to clean up the easy ones first and then come up with manual algorithms for the harder ones.

My favorite approach is what I’m doing with Facebook. Every day I go into the Events tab and look at the birthday list. I then unfriend the people whose name I don’t recognize or who I don’t want to consume in my news feed. Since Facebook’s social graph is on the public side, people can still follow me (ala Twitter follow). I view this as a reverse birthday gift which probably enhances both of our lives.

In contrast, I’ve continued to just accept all LinkedIn requests except from obvious recruiters or people who look like spambots. I know they can pay to get access to my social graph – that’s fine – I want them to have to pay someone or work a little for it, not just get it for free, but the benefit of having a wide social graph on LinkedIn for the one time a week I use it to hunt someone down somewhere far outweighs the pain of being promiscuous.

I’ve continued to find and use other tools for managing all the data. One of my new favorites is Engag.io. Rather than getting a stream of Facebook email notifications, I check it once a day and respond to everything that I see. I’ve noticed that I find comments in other services like Foursquare that I was previously missing, and rather than having a pile of clutter in my inbox, I can interact it with once a day for ten minutes.

When I reflect on my approach, it doesn’t surprise me that it’s very algorithmic. That’s how I’ve always driven my content consumption / content generation world and part of the reason it doesn’t overwhelm me. Sure – it spikes up at times and becomes less useful / more chaotic (like it did last year when I realized Facebook wasn’t really useful for me anyone.) This causes me to step back, figure out a new set of algorithms, and get it newly tamed. And yes, Facebook is now much more useful and interesting to me after only a few months of cleanup.

I’m always looking for new tools and approaches to this so if you have a great one, please tell me. For example, the “unfriend on birthdays” approach was suggested several times in the comments to one of the posts and after trying a Greasemonkey plugin, manual unfriending on the iPad while watching TV, and other brute force approaches, I just decided I’d clean it up over a year via the birthday approach. So – keep the comments and emails flowing – they mean a lot to me.