Brad Feld

Tag: email

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 <company> for <mycompany>”. 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 SaneBoxTodoist, 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<downarrow><enter>. 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?