Brad Feld

Category: Productivity

I had a great breakfast meeting at the Cambridge Marriott with Michael Schrage, a research fellow at MIT yesterday morning. We had never met before and I loved the conversation – his brain was bubbling with ideas that are relevant to many of the things I’m interested in, he challenged some of my thinking, and we had a deep and awesome conversation about open source hardware, makers, and MakerBot.

This morning Raj Bhargava (who recently co-founded two companies I’ve invested in – Yesware and SkedulMe) sent me a blog post by Michael titled Tip for Getting More Organized: Don’t. In it Michael makes the argument that the notion of spending time each day organizing your tasks, the concept of email folders, and the idea of productively organizing yourself is obsolete. The money quote at the end is:

“The essential takeaway is that the new economics of personal productivity mean that the better organized we try to become, the more wasteful and inefficient we become. We’ll likely get more done better if we give less time and thought to organization and greater reflection and care to desired outcomes. Our job today and tomorrow isn’t to organize ourselves better; it’s to get the right technologies that respond to our personal productivity needs. It’s not that we’re becoming too dependent on our technologies to organize us; it’s that we haven’t become dependent enough.”

I couldn’t agree more. I spent almost no time “organizing my tasks.” In fact, I no longer have a task list. I have outcomes I’m going after. They fit within a daily, weekly, quarterly, and annual tempo. The daily and weekly outcomes are dynamic – I have to think about them regularly and they change and shift around (I have new ones each day and new ones each week.) I call these my Daily P1s and my Weekly P1s (which I wrote about recently in a post titled Managing Priorities)- the daily ones are the three things I want to accomplish before I go to sleep; the weekly ones are the three things I want to accomplish each week before Monday morning.

But that’s it. I have a daily schedule that is highly structured (and managed by my assistant) so I don’t have to spend a millisecond thinking about who I need to meet with, where I need to be, or what I need to schedule for later. If you know me, you know that I just “go where my schedule tells me to.” I process all of my email with one touch, I write what I want when I want, and I have a strong conceptual hierarchy for prioritizing high interrupt things. I also stay off the phone unless scheduled – if you spend time with me for a day it’s likely that the only time I’m on the phone is with Amy to say “hi – I love you” or have a pre-scheduled call.

I love the notion of focusing on outcomes rather than organization. For as long as I’ve been an adult, I’ve been hearing about, reading, thinking about, and experimenting with different technology to be “more organized and productive.” I’m an aggressive user of whatever exists and when I reflect on where I’m at in 2012 I definitely feel like I’ve gotten to the place where I’m spending almost all of my time and energy on outcomes and achieving them, not on organizing myself.

If you are someone who spends 30 minutes or more a day “organizing yourself”, I encourage you to step back and think about what you could change and how that might shift you from focusing on organizing to working toward outcomes. It’s liberating.


Fred Wilson had an excellent post up this morning titled Social Media’s Secret Weapon – Email. I completely agree that email is the key communications channel for social media and have written about this before in posts like 100% Click Through RateEmail – The Original Social Graph and Email Is Still The Best Login.

I’ve been investing in email related stuff for over 15 years going back to Email Publishing, my very first Boulder-based investment which I believe was the very first email service provider (ESP) and was acquired by MessageMedia which was then bought by Doubleclick. Fred and I are both investors in Return Path which he calls out in his post as the category creator and market leader in email deliverability. I love Return Path as a company and am incredibly proud of what they’ve done as a business.

My partners and I have continued to invest aggressively in what we believe is social media’s secret weapon which we refer to as the comm channel in a hat tip to the TV show 24. In Fred’s post, the comm channel is email. Our investment here is in SendGrid, a company that came out of TechStars Boulder 2009 and is one of the white hot companies in Boulder. They directly address the problem Fred describes which every software developer knows is a pain in the ass, uninteresting, hard to do well, but needs to be done right. Every web app sends transactional email – rather than build all the code yourself, just let SendGrid to it. They are now doing it for over 24,000 companies, sending out over 60 million transactional emails a day, and just sent their 10 billionth transactional email.

But email isn’t the only comm channel. Everyone that uses apps on a mobile phone is likely experiencing push notifications as an increasingly important as a form of engagement. While mobile phones used to only really work effectively with SMS, you now have SMS, email, and push notifications. So we invested in Urban Airship who does for push notifications what SendGrid does for email. Like SendGrid, they are growing like crazy, are in use by over 10,000 customers and have sent over 3 billion push notifications.

My message to all web developers – if you are serious about what you are doing, focus on your app. Don’t waste precious development time on all the activities around the app. You likely no longer sit around with a screwdriver setting up a server in a datacenter – instead you are using a cloud provider like Rackspace or Amazon.  Don’t spent your time coding up an email notification infrastructure – use SendGrid. And if you are a mobile developer, don’t waste your time writing a bunch of code for push notifications – use Urban Airship.

Most importantly, don’t ignore the thing that will actually make your web app get adoption and retention – comm channels!


I’ve started a new category on my blog called “Best Practices.” These are going to be posts inspired by my experiences with various companies that I feel are above and beyond the normal activities you’d expect. The first one comes from Matt Blumberg, the CEO of Return Path. Earlier this week the board received an email from him that included the following:

“Although [our CFO] approves my expenses in our accounting system, inspired by Mark Hurd, I decided it would be a good idea to add a level of transparency to you in terms of my expenses.

To that end, I’m doing two things:

  • I’ve asked our auditors to include some analysis/testing of my expenses in this year’s audit
  • Attached, please find a spreadsheet which details all expenses, with a summary tab that has the overall picture and a few explanatory notes

Trash or treasure, as they say, but please feel free to ask any questions or poke any holes you’d like.  I can assure you that I’m pretty disciplined about expenses (both in terms of not being profligate and in terms of not abusing company money for personal use), but I did think it would be good housekeeping for you to have visibility.”

To a person, we responded that while unnecessary, this was a nice gesture of transparency. The spreadsheet that Matt sent around had every expense item he was reimbursed for in the year. The summary was helpful for putting it all in perspective, but I could look and see where (and with whom) Matt ate dinner, which hotels he stayed in, how much he paid for plane flights, and what he charged to the company as miscellaneous expenses.

I thought about it more and decided it was an awesome display of trust. I have immense respect for Matt, his leadership, and his management skills. But more than that, I’d go to the ends of the earth to do anything for him. Unilateral, unexpected gestures like this one just reinforces that for me. So, more than just transparency, this best practice increases the level of trust between a CEO and his board.


I’m at the end of day three of another very intense, but enjoyable and satisfying week. I’ve been in Seattle the past two days and am headed to LA for the next two days before finally making it home after being on the road for the past two weeks.

As I was getting ready to go to bed in order to wake up in time to make my 6:40am flight, I was rolling my one remaining priority for the week around in my head. I was thinking to myself, “two down, one to go.” And I realized I have been using a construct of “three priorities a week max” for a long time.

Now, I do a lot more than three things a week. But, on Monday mornings as I’m going through my daily information routine, I usually carve out a few minutes to make sure I have my priorities for the week firmly lodged in my brain. I limit myself to three as I don’t think you can have more than three “highest priorities” at any given time. When I start the week, I make a clear mental commitment to get these priorities (or P1’s in Zynga speak) done. Each day when I wake up, I think about what I need to do to get closure on these priorities.

Some weeks I have three, others I have one or two. I always have at least one. And they are always important. Occasionally I can’t get one done and it rolls over into the next week, but once something becomes a P1 it stays a P1 until it gets done. And I can never have more than three P1’s. And they should all be able to be completed by the end of the week. But most importantly, they are clearly defined and easily explained (e.g. if you walk up to me and ask me what my P1s are for this week, I should be able to recite them without thinking.)

While I have plenty of things that I’m working on that have a much longer arch than one week, I find this weekly rhythm to be very grounding. I have a clear sense of accomplishment on a weekly basis, I clear the decks of big priorities, and I regularly tackle hard stuff that just needs to get done. I also have many more than three things that I complete each week, including things that regularly come up that are as important (or even more important) that whatever I’ve defined as my P1s for that week. But I don’t shuffle the priorities around – by having the big ones for the week set at the beginning of the week, I have a clear set to focus on whenever I need to re-ground myself.

One more to go. I’ve got two days to get it done. And I’ve got plenty of time on my remaining two plane flights to knock it off.


Over the past year the amount of emails I receive on a daily basis from entrepreneurs has reached a point where I can’t deal with it any more.  My partners at Foundry Group feel the same and as a result we’ve moved to twitter to deal evaluation

If you are interested in talking to me about a potential investment, please just tweet it.  Limit yourself to 140 characters – that’s more than enough to describe what you are doing.  Optimally, you’d DM me, although I realize that I have to follow you for this, so just use @bfeld in your tweet and I’ll see it.  And please – don’t sent me multiple tweets – that kind of defeats the purpose.


After downloading Skype 4.2, I realized that I could now invite all of my Facebook friends who had Skype accounts to my Skype contact list.  So I did.  Unfortunately the Skype UI for this sucks so I had to go through about 1,000 entries a screen of five at a time unchecking the Facebook friends I didn’t want on Skype.  I ended up inviting about 280 – fortunately I was on a conference call for the thirty minutes it took me to grind through this.

The data field used for the match was email address.  Shocking, I know.  It’s the same data field used to log in to Facebook and Twitter.  Google sort of uses email (at least the gmail) account for their authentication, although now that I have both my gmail account (brad.feld@gmail.com) and my email account (brad@feld.com) in Google’s system, I am constantly having to fight with the “reauthorize me to access that thing via brad.feld@gmail.com) game” since Google hasn’t solved for multiple email addresses yet.

More and more sites are integrating Facebook Connect, Twitter “Connect”, or both.  Yahoo has such a golden opportunity to do this and own it but they blew it.  Google seems to have also missed this and ceded it to Facebook and Twitter for some reason.  Microsoft has been trying for a decade first with Passport and now Live ID. And then there is Skype with their 20m simultaneous users.  Or Amazon with their gazillion users authenticating via email.  And then there’s Barnes & Noble – if I want to create an account I get to use my email address.  And the list goes on and on.

Facebook and Twitter are in a perfect position to own single sign on.  I just don’t understand why Yahoo and Google blew this although I don’t really care.  What I do care about is that there seems to be a natural convergence on email as the user id and authentication via widely pervasive services like Facebook and Twitter rather than entertainingly complex approaches like Oath

I predict email is going to become even more important in the next few years.  There’s no reason for me to have a phone number any more – you should just be able to contact me via brad@feld.com.  And that should authenticate me anywhere.  And – as a messaging protocol – I should be able to use my “inbox” (wherever or whatever it is) as my central notification point.

It’s remarkable that 15 years after commercial Internet email started to proliferate, it is still at the root of all the commercial Internet activity.  Very very cool.


I was thinking about how to drive CTR’s up via different mechanisms this morning when this email arrived in my inbox.

image

I remembered talking about high CTR email response rates with Dave McClure and Shervin Pishevar when we were in DC on our Startup Visa trip at the beginning of March.  I’d forgotten about this conversation until this email showed up while I was thinking about this.  Of course, I clicked to see where Dave had tagged me (it was on a Huffington Post article about innovation.)

I thought about it for a few more seconds and realized that to date I have a 100% CTR on an email from Facebook that says “<X> tagged you on Facebook.”  I can’t come up with anything else that I have a 100% CTR on, but I’m now looking out for it.

Do you have any examples of transaction emails like this you receive that have 100% (or even 50%+) CTRs?


I’ve been obsessed with the notion of email as the ultimate social network for a while.  I wrote a post in 2007 titled Social Networks In Obvious Places that catalyzed me to thing harder about this as an investor.  I eventually decided that the email address is the ultimate reference id for one’s current online identity and that it was ludicrous to ignore this notion. This ultimately led to my investment in Gist in 2009. 

Today, there are a number of folks approaching different parts of the problem.  I believe the underlying data architecture and approach is critically important, as email resides in many different data stores and move through many different systems.  In addition, there are numerous other applications that use email as the key reference id independent of username (LinkedIn, Twitter, and Facebook come immediately to mind, but there are thousands of others.)  There is no question in my mind that the web (or the cloud if you like) is your friend in this scenario.

This morning, I noticed that Microsoft had released a beta of Microsoft Outlook Social Connector for Outlook 2010, 2007, and 2003.  I’m running Outlook 2007 on my desktop at home so without thinking too hard I downloaded it, installed it, restarted Outlook, downloaded the LinkedIn connector (the only one available for 2007), restarted Outlook again, and started cranking through email.  I liked the Email Connector window that appears at the bottom of my Inbox view, but I noticed that none of the LinkedIn data seemed to be appearing for my specific contacts.  I didn’t think much of this and figured Outlook was doing something magical in the background (since various info from my Inbox and Calendar started appearing in this view.)  I noticed a few things I didn’t like, such as the every calendar item taking up two lines in the display because the second line was an invite.ics file, but I figured that was just beta stuff.  After an hour or so, I had to jump in my car and head to Denver for a board meeting. 

Once I got into AT&T cell phone range (about ten minutes from my house) I swiped left on my iPhone and typed in the last name for a CEO of a company I’m on the board of.  I noticed that I had two entries for him.  This was strange because I’m meticulous about keeping my address book clean and deduped.  The first entry didn’t have his phone number.  That was really strange since I call him regularly.  The second entry did and looked like the correct record.  I called him, but something was bugging me.

After we talked, I did this again to call another person.  Same issue.  This time I noticed a picture with the little LinkedIn logo on the first entry, but again no phone number.  The second entry didn’t have the LinkedIn picture, but had the correct phone number (and full entry).  By this point I’d figured out what had happened.  I called Amy, told her to shut down my computer at home (I usually leave it on during the day) just in case my new friend the Outlook Social Connector could be stopped before it imported my entire LinkedIn file as new contact records.

I was annoyed throughout the day that I’d munged up my address book.  Tonight, when I got home, I hopped on another board call.  I fired up my computer, uninstalled the Outlook Social Connector, and then spent a few minutes poking around in Outlook contacts trying to find an easy way to delete all the new records.  I fought my way through a few different Outlook contact views and couldn’t figure out how to get the records to consistently appear.  If I searched by name, all the dupes came up.  But if I went into a list view, no such luck – only the correct record appeared and the new LinkedIn ones were no where to be found.  I manually started scrolling through my address book on my iPhone while on the call but by the time I got through the B’s I realized this was an idiotic way to do this and there must be a better way.

A few minutes later it occurred to me that Outlook might have created a new “subfolder” in the contacts view and put all the LinkedIn ones there.  Lo and behold it did and all I needed to do to get rid of the 1800 new contact records was to delete the LinkedIn folder.  Done.  After some happy iPhone syncing they are all gone from my iPhone also.

The decision to take this approach at a data level is beyond comprehension to me.  Almost 100% of the duplicate LinkedIn contacts shared the same email address as my Outlook address records.  I didn’t want a NEW contact record for each LinkedIn one, I wanted them to be “magically attached” to my existing contact record.  So – when I look up Brad Feld, I don’t get the “Brad Feld” Outlook contact record and the “Brad Feld” LinkedIn contact record.  They are both brad@feld.com – that’s all I want.

So – be forewarned – unless you want to gunk up your address book with duplicates, don’t install the current beta of Microsoft Outlook Social Connector.  Maybe I did something wrong, or have a weird configuration of Outlook 2007, but I simply did a straight install.  Maybe Microsoft will fix this in the next version, but it definitely doesn’t seem ready for prime time, especially on live data.


I’ve been an Internet email user since early 1984 when I got my first Project Athena account as an undergraduate at MIT.  Notwithstanding all the “email is dead” messages over the years, I continue to use email as my primary online communication mechanism.  There are an enormous number of things that frustrate me about email, most notably the lack of fundamental innovation in email clients and servers.  That said, as a messaging tool – it still dominates for me.

Several years ago I started saying that “my social graph is in email.”  I found it interesting that Facebook and LinkedIn used email as a primary messaging layer to remind me to come back to Facebook and LinkedIn respectively to check what was going on.  This signaled confirmation to me that these systems were making sure they were using the most persistent messaging layer to build and reinforce their social graphs.

For whatever reason, the primary email product providers have been either painfully slow at realizing this or have decided to ignore this.  Facebook and LinkedIn have benefitted massively from this, but the biggest recipient of this neglect is Twitter which has created an entirely new messaging protocol (think Twitter API as analogous to SMTP).

Suddenly, in the past year, entrepreneurs have woken up to the potential of the email social graph.  As I’ve mentioned before, we invested in Gist to directly address this opportunity.  Xobni is another well known company that is attacking this.  But another intriguing fact is the number of younger entrepreneurs that are working on this problem.  Each of the TechStars locations (Boulder and Boston) has a company that – at its core – is built around the premise of email as the original social graph.  In addition, as a mentor in the fbFund Rev 2009 program, I’ve recently started working with another company working on yet a different angle to this problem.

Now, these companies aren’t creating new email clients.  They are working on products or web services that take advantage of all the implicit information generated by your email activity.  They aren’t limited to just email (if you are a Gist user, you understand this well), but use email (name@domain.com) as a key information pivot point.  If you step back and think about it, while https://www.facebook.com/bfeld is new and full of yummy chocolaty goodness, brad@feld.com is really my “unique” identifier.

I’m not going to talk about the three new companies I’m working with on this problem yet – I’ll let them “launch” on their own timetable and I’ll talk about them when they are ready.  In the mean time, I’ve continuing to look to talk to more people that share this premise.  If that’s you, feel free to email me.


The amount of mailing list spam I’ve been getting has been steadily increasing with a huge jump in the last few months.  I was perplexed by it – this isn’t real spam (they are all opt-in mailing lists – many of which I recognize the associated organization.)  However, I hadn’t opted-in to any of the lists!

Some were political lists, some were technology lists, and some were random things.  As the election got closer, the political ones increased.  Today, as I was hitting delete over and over again I realized that I must have been on a seed list that got passed around between organizations.  This is a pretty typical spam thing and gets 99.999% blocked by Postini (my anti-spam system), but until recently I hadn’t connected the dots on it from legitimate opt-in emails since I actually want to get the emails I’ve opted in to.

Specifically, any mailer who understands CAN-SPAM and cares about reputation won’t share their lists this way.  At the minimum, I’d get an opt-in request from the new list which – while not great – is at least tolerable.  This phenomenon isn’t limited to the political lists – I’ve been noticing it more broadly across all the tech email lists.

In addition, it appears that I’m getting added to email lists whenever I give someone my business card.  I find this particularly annoying for all the non-profit organizations that I’m involved with.  My reaction to getting email spam from them is negative, which I presume is the exact opposite of how they want me to react.  While this practice doesn’t actually violate CAN-SPAM, it’s definitely in the category of "bad email practices" in my book. 

We’ve been involved in this arena as investors for a long time with both Postini (on the email security side – now part of Google) and Return Path (on the email deliverability side).  I’m really proud of each of these companies – they’ve both created real businesses helping eliminate bad email and insure that good email gets through to the inbox. 

Fred Wilson just wrote a long post on why his firm – Union Square Ventures – recently invested in Return Path.  After thinking about my mailing list spam issue, I think we are going to have another major iteration of spam dynamics that we’ll have to address and Return Path continues to be extremely well positioned to do it.

BTW – do you want to Simplify The Season with Dell Small Business?  Unsubscribe.  Delete.