Brad Feld

Tag: email

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.

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.


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.

Cliche 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://www.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://www.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.