Brad Feld

Month: December 2014

Let’s start with a brief history of my investment-led fight against the perils of spam and my never-ending love of SMTP.

We were investors in Postini and my partner Ryan sat on the board. It transformed my life – with one minor change of an MX record some time in 2002 all the spam in my inbox disappeared. Well – it disappeared before it got to my inbox. Or even my server. The awesomeness of Postini was that it was the first cloud-based email anti-spam solution. And it was a beautiful thing that Google acquired in 2007 for $625m.

One of the benefits of our investment in Postini is a life-long friendship with Scott Petry. Scott is the co-founder of Authentic8, which we are also investors in. Scott also sits on the board of Return Path, which is run by another life-long friend Matt Blumberg.

Scott worked at Google for three years after the transaction for Dave Girouard (who used to run all of enterprise for Google and now is CEO of Upstart and on the board of Yesware with me) integrating Postini into all of Gmail’s infrastructure. We continued to use Postini as our spam filter (in front of Gmail) until Google transitioned all of Postini into the Google apps service.

You get the picture. There’s a nice thread through all of this SMTP, email deliverability, and anti-spam stuff in my world, both in investment and relationships. So I generally don’t think much about spam since in the past it just disappeared, or well, never appeared in the first place.

When I came home from my one month sabbatical in Bora Bora, I archived all the 3200+ emails in my inbox. If you missed my vacation reminder during that time, it said:

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.

On Thursday, 12/4, Amy decided to scan through her email so I went to the business center at the St. Regis in Bora Bora with her and did the same. I simply started at the top and “read / archived” each of the around 3,300 emails (using the “[” shortcut). I’m a fast reader so I skimmed the emails I cared about. Mostly I just played a video game with the [ key.I might have had a tropical drink while I was doing this.

I didn’t respond to anything and just ran this drill again early Monday morning to finish up. I then turned off my vacation reminder, had Inbox Zero, and got started again.

Yesterday, I had a weird feeling that I’d missed something that I heard about in another email thread. I was procrastinating from working on the final edits to my new book Startup Opportunities (yes – I’m doing that some more right now, but I’ve got a nice empty day in front of me) so I randomly checked my Spam folder in Gmail. I never, never, never do this so I was suprised when on the first page I saw a legitimate email. I opened it, clicked on Not Spam, and scrolled to the next page, where I saw another one. And another one.

I had 5,500 messages in my spam folder since I got back on 12/8. I went through all off them – it only took about 10 minutes. I found 39 legitimate emails. Not notifications, not email newsletters – but real emails sent to me by people I often get emails from. Here’s a screenshot of the legit ones.

Valid emails in gmail spam folder

I did my dutiful work and hit “Not Spam” on all of them. I was perplexed and talked to my friends at Return Path who gave me some feedback.

This morning, I had 433 messages in my Spam folder. This time, they all looked like they should.

Screen Shot 2014-12-24 at 7.36.51 AM

I’m hoping that this was only a temporary glitch in the matrix. However, I’ll be checking my Gmail spam folder on a daily basis for a while. Boo.


There is a moment during the exploration of a new relationship where a switch flips and the answer is “I want to do this.”

With Mattermark, I remember the moment clearly – I was at The Kitchen in Boulder with the founders (Danielle Morrill, Kevin Morrill, and Andy Sparks) and my partner Seth. I had just put a garlic french fry in my mouth (if you’ve never had them at The Kitchen, they are epic) and looked over at Seth. He looked at me and gave me that “yeah – we should do this” look. And that was it.

As an investor for the past 20 years, I’ve had this happen many times. When I first started investing as an angel investor in 1994, I was focused on a very simple set of criteria. First, did I care about / have affinity for the product? Next, were the entrepreneurs obsessed about their product? Last, did I want to be a long term partner with the entrepreneurs?

With a slight diversion in the late 1990’s when everyone (including me) lost their mind for a few years, I’ve held to this algorithm for all my investing. If you look at the boards I’m on, including companies like Fitbit, FullContact, Oblong, Orbotix, littleBits, Yesware, and Return Path, this pattern should be pretty clear. And if you ponder how I originally got involved in Techstars, and how my role has evolved, those three criteria loom large.

I’ve been interested in private company data since I started Feld Technologies in 1987. Well before the web existed, I was physically tearing articles out of industry magazines and sending them to customers, prospects, other entrepreneurs, and my partner Dave, who probably got tired of the stack of paper with notes scribbled on them that landed on his desk each day. I’ve been through multiple iterations of competitive databases, endless applications for trying to keep track of companies I’m either an investor in or compete with, and every different type of alerting system you could imagine.

During the first decade of my experience with this, I couldn’t afford to subscribe to anything. Every now and then I’d get a free trial and realize how shitty the underlying data was. For the past almost 20 years, I’ve been able to afford the subscriptions, but the data is still shitty. There have been several efforts to crowdsource this kind of data, or make it publicly available, but none have resulted in anything magnificent.

So, regarding the question of “do I care about / have affinity for the product of Mattermark”, the answer was a strong, unambiguous yes. I know how hard the problem is, how wide open the opportunity is, how far it will scale in multiple directions (not just the data set, but the use case, target market, and ultimate product family.) My affinity in this case borders on obsession, just like it does with the Contact Management problem.

Now, let’s shift to #2: “Are the entrepreneurs obsessed about their product?” If you know Danielle, Kevin, and Andy, you know the answer is yes. But there’s nothing quite like experiencing it. Over the past year, as I’ve gotten to know Danielle, I’ve seen her obsession and focus, not just on the short term Mattermark product, but on the long game she and the team is playing. During dinner at The Kitchen, which was the first time we were face to face since we’d met at the beginning of the year, and the first time I’d interacted with Kevin and Andy, all I had to do was sit there, prompt every now and then, and I got another layer of product vision. Obsession. Endless intellectual exploration of where this could go. When I challenged ideas, there was no defensiveness, just more exploration. When I suggested things, there wasn’t blanket approval or rejection, but rather a socratic inquiry as Danielle, Kevin, and Andy tried to understand what I was suggesting. I watched Seth do his thing and the gang continue to engage the same way. At some point, Seth and I had the look I referred to at the beginning of this post.

I’ve always been impulsive about #3: “Do I want to be long term partners with the entrepreneurs?” For the first decade of my investing experience, I made a lot of mistakes on this dimension. Howard Diamond, a close friend and entrepreneur I’ve worked with since 1996 (now the CEO of MobileDay), regularly criticized me as been too trusting, too willing to see the good in people, and too patient with people. This kicked me in the ass very, very hard between 2001 and 2004. While it didn’t make me cynical, I calibrated my filters as I slogged through three more very long years between 2004 and 2007. I like to believe that I brought a new frame of reference around this to Foundry Group, informed by Howard’s constructive criticism, feedback from lots of other friends, learning from my mistakes, and all the long-term positive relationships that I now had as a frame of reference.

I also have a lot of people in my world who know me well, know what I like, and know who I will work well with. This includes a small set of VCs, such as Jon Callaghan at True Ventures and Greg Gottesman at Madrona who know me so well that they only approach me with companies and founders they know I will love. But mostly I use the many CEOs and entrepreneurs I have developed a long-term relationship with to help me calibrate what Amy likes to refer to as my “poor impulse control”, sort of like Raven’s from Snow Crash.

The combination of my own experience and feedback from my universe – both good and bad – made it clear that I wanted to be long term partners with Danielle and team. Recognize that I’m not looking for unambiguously good feedback – we are all flawed in different ways, make mistakes, and have endless and enormous opportunities to learn. An understanding and appreciation of that by the entrepreneurs I work with is deeply important to me.

Back to dinner. Seth eventually had to leave and we kept at it for a while. Driving home, I rolled around what was left in my mind as questions and concerns I had about making an investment. When I got home 20 minutes later, I had none. When we got together the next morning for more discussion, it was easy to look forward and pretend I was already an investor, which felt good. At some point, we shifted to a mode where I asked Danielle, Kevin, and Andy what they wanted, expected, and demanded from an investor. I let them ask me whatever they wanted for a while. But by this point I was all in, as long as they wanted to work with me.

Sure, we did some more up front work and some formal legal diligence, but in that moment at The Kitchen, Seth and I knew that we wanted to be investors in Mattermark.

And that was that. Last week we led a $6.5 million round in Mattermark. I’m delighted to finally be an investor in a problem I’ve been obsessed about for 20 years. We are at the beginning of the journey – check back in a decade from now to see whether or not we are successful. But, regardless, this is a team I hope to work with for the rest of my investing career.


I rarely read physical magazines anymore. I only read in the bathroom and most are things I forget to unsubscribe to or that Amy gives me.

Today, I finished the most recent MIT Technology Review where I was reminded about the amazing MIT Science Fiction Society. As a sci-fi nut, I realized I’d screwed up by not having a lifetime membership. So, I’m now trying to figure out where to send my $260 to be a lifer.

As I was reading the other MIT thingy I get regularly (the MIT Science News and Events) I saw a mindblowing stat from the most recent Putnam Competition (the 74th). MIT took four of the top five places, won the team competition, and had 43% of the top 81 scores (depending on the rounding, that’s either 34 of 81 or 35 of 81.) Either way, it’s nuts.

When I was a freshman, I thought I was hot shit at math. I was the star of my high school Mu Alpha Theta team and as a senior had an unexpected first place finish in a Rice University national competition for Algebra. I was pretty damn good in the calculator competitions on my TI-58C. Yes, I was a nerd then, and I’m still a nerd now.

While I got an 800 on the math SAT, I booted all the AP tests except Biology (to place out at MIT you need to get a 5) – I can’t remember what I did the night before the tests but it clearly wasn’t something that I should have been doing if I wanted to pass them.

So, when I got to MIT, I took 18.011, which was the “advanced first calculus course.” It was straightforward. I then took 18.021 (“advanced second calculus course.”) It was less straightforward. If I had placed out on the Math AP test, I would have taken 18.02 and 18.03 instead. So I felt a little less like hot shit.

My friend (and future business partner Dave Jilk) knew I liked math so he encouraged me to take a course called 18.701: Algebra. I figured “Algebra – I’ve got that.” I don’t know if Dave was serious or just fucking with me, but when I got a 12 on my first test I knew I was fucked. I dropped the class shortly thereafter. Dave, of course, got an A in that one. He’s much better at math than I am.

While I ended up being “fair” at math by MIT standards, I developed a weird savant like numeric skill. I can remember crazy amounts of number and data pairs. I can also do a lot of math in my head, although I’m often off by an order of magnitude, which of course either matters a lot or is easy to adjust when you realize it.

Mitchell M. Lee, Zipei Nie, Bobby Shen, and David Yang – y’all are math studs. Well done representing the Beavers in the 2014 Putnam.


I’m gearing up for a long series of posts about the various books I read on my month off on Bora Bora. In the mean time, I read a bunch of stuff online this morning (from Friday through today) and thought I’d give you a taste of some of it in case you feel like digging in.

I started with How Reading Transforms Us. It’s a good frame setting piece about some new research on the impact of reading – both fiction and non-fiction – on humans. There is a pleasant surprise in there about how non-fiction influences us.

As with many of you, I’m deeply intrigued by what’s going on around the movie The Interview. Fred Wilson wrote a post titled The Interview Mess in which he expresses some opinions. I’m not in opinion mode yet as each day reveals more information, including some true stupidity on the part of various participants. Instead, I’m still enjoying The Meta Interview, which is how the real world is reacting to The Interview.

Let’s start with the FBI’s Update on Sony Investigation followed by Obama Vow[ing] a Response to Cyberattack on Sony. 2600 weighs in with a deliciously ironic offer to help Sony get distribution for The Interview. Sony’s lawyers unmuffle their CEO Michael Lynton who fires back at President Obama.

Now it starts getting really interesting. North Korea says huh, what, wait, it wasn’t us and seeks a joint probe with US on Sony hack (yeah – like that is going to happen.) After everyone worrying about not being able to see The Interview (which might now be the most interesting movie of 2014 before we’ve even seen it), Sony says Nope, we didn’t chicken out – you will get to see The Interview.

Apparently, Obama isn’t finished. Instead, he’s just getting started. He’s decided that the North Korea hack on Sony Pictures was not an act of war but is now trying to decide if it’s terrorism so he can put North Korea on the terrorism sponsors list to join Cuba, Iran, Sudan and Syria. No wait, maybe it’s to replace Cuba which Obama has decided to restore full relations with.

Thankfully, Dr. Evil weighs in on this whole thing and makes sense of it (starting at 0:40).

At the same time we are struggling over North Korean’s cyber attack terrorism censorship thing, we are struggling with our own internal efforts by some very powerful companies to figure out how the Internet should work in the US. Hmmm – irony?

Let’s start with the cable industry’s darkest fears if the Internet becomes a utility. According to the Washington Post, Congress now wants to legislate net neutrality. And Verizon tells the FCC that what they do doesn’t really matter to them.

The FCC situation is so fucked up at this point that I don’t think anyone knows which way is up. Fortunately, we have the Silicon Flatirons Digital Broadband Migration Conference happening in February which I’m speaking at to clear this all up. Well, or at least watch some entertaining, very bifurcated arguments about First Principles for a Twenty First Century Innovation Policy.

If you are a little bummed by now about how humans behave, check out this article where MIT Computer Scientists Demonstrate the Hard Way That Gender Still Matters. For a taste:

The interactions in the AMA itself showed that gender does still matter. Many of the comments and questions illustrated how women are often treated in male-dominated STEM fields. Commenters interacted with us in a way they would not have interacted with men, asking us about our bra sizes, how often we “copy male classmates’ answers,” and even demanding we show our contributions “or GTFO [Get The **** Out]”. One redditor helpfully called out the double standard, saying, “Don’t worry guys – when the male dog groomer did his AMA (where he specifically identified as male), there were also dozens of comments asking why his sex mattered. Oh no, wait, there weren’t.”

But the fun doesn’t end with cyberterrorism, censorship, incumbent control, or gender bias. Our good friends at Google are expanding their presence in our lovely little town of Boulder from 300 employees to over 1,500 employees. I think this is awesome, but not everyone in Boulder agrees that more Googlers are a good thing. I wonder if they still use Lycos or Ask Jeeves as their search engine. And for those in Boulder hoping we municipalize our Internet net, consider FERC’s smackdown of the City of Boulder’s Municipalization position.

Oh, and did you realize the US government actually made a $15 billion profit on TARP?


I always look forward to the annual Techstars video. I enjoy seeing it, and usually enjoy being part of it.

This year I’m one of your favorite Sesame Street characters. Hang in there for New Years Resolution #9.

Cookie cookie cookie. Give me cookie.


I live in Gmail. Gmail Contacts has been lame for a long time. Within an email, it’s even lamer on the right side bar, especially since it could be so amazingly useful.

FullContact has just released their FullContact for Gmail product. It’s a free download in the Chrome Store. I’ve been using it for about six months since and it’s just awesome.

I’ve been obsessed about the contact management problem for many years. In 2012 when we invested in FullContact, I wrote a post titled One Address Book To Rule Them All. FullContact has made great progress in the past two years on this problem while building a substantial enterprise API business. At the same time, we’ve been working extremely hard on a wide range of consumer products which are all just now rolling out into production (many have been in beta for the past year.)

I use all of them. FullContact for Gmail. FullContact for iOS. FullContact for MacOS. FullContact Web. All integrate with each Address Books on all my devices and computers. Everything syncs bidirectionally. Everything integrates with my contacts in Facebook, Twitter, LinkedIn, AngelList, and Foursquare. FullContact deduplicates everything so I only have one integrated contact record for each person. It enriches each contact record automatically with new public data that is finding on a continual basis.

This is a really hard problem. We invested in a company called Gist in 2009 – it was acquired early in its life by RIM in a deal that was financially successful for everyone involved, but before Gist rolled out in a big way. At the time, Gist was competing with several other companies, including Rapportive, all which were ultimately acquired and then more or less abandoned.

While we hoped to blanket the world with FullContact in 2014, we knew that waiting until we got the underlying massively large data infrastructure right, at scale, in a way that wouldn’t fuck up any contacts, was price of admission for going big on the consumer side. So we focused on building out our enterprise API business which started the year at a substantial level and tripled in 2014. At the same time, we acquired a company called CoBook and went extremely heads down on getting to a place where we thought we were ready to fix everyone’s address books on Planet Earth.

We are there. FullContact for Gmail is the first product to be released. If you are a Gmail user, quit fooling around, download it, and make your life a lot better right now. And get ready for several more releases in the next few months.

The FullContact team works as hard as any team I know. I’m proud of you guys and glad to be on this ride with you to finally solve a problem that has vexed me my entire adult life.


I’m fascinated with Detroit. When I was there in October 2012 with my partners Ryan and Jason to run the Detroit Marathon we talked about the idea of getting more involved there in some way. Jason grew up in Detroit and has lots of stories there. He goes back regularly to visit his parents and Ann Arbor where he went to school.

Since we were there, I’ve read a few books on Detroit and many articles that popped up about it’s downfall along with some of the entrepreneurial activities trying to revive the city. My partners and I believe that Detroit hit rock bottom around 2012 and in a decade has the potential to be an amazing city once again.

So, Jason and I started talking more about things we could do to positively impact the Detroit startup community and looped the Techstars gang into the conversation.

David Cohen, David Brown, and the team at Techstars grabbed it and ran with it. Last week Techstars announced the new Techstars Mobility program, Driven by Detroit. The local Detroit startup community engaged very powerfully in the idea. From the post about it:

“Throughout the development of the Techstars Mobility program, Techstars worked with Detroit based venture capital firms Fontinalis Partners, Detroit Venture Partners and Renaissance Venture Capital to recruit mentors and ensure capital was ready to deploy in the region. Many other venture firms have also contacted Techstars communicating their interest in bringing capital to Detroit.

Techstars will be bringing their proven accelerator model and extensive network of mentors, founders and corporations to Detroit to support this program. Techstars will also coordinate efforts across the Detroit entrepreneurial ecosystem as a member of the Detroit Technology Exchange (DTX), ensuring that Techstars can have a positive impact across the entire community. Techstars Mobility, driven by Detroit will run for three years with a new class of 10 startups each year.

Several years ago I met Ted Serbinski. Three years ago he moved from San Francisco to Detroit to help rebuild the city. In his words:

“Ten years from now, San Francisco will be just as good as it is today. But in ten years, Detroit will be a roaring city once again, defining a new technology hub at the intersection of muscle and brains. Where do you want to be in ten years? Status quo? Or one of the heroes that rebuilt a city?”

I think Ted is awesome and it’s super exciting to have him join Techstars as the Managing Director of Techstars Mobility. He’s written a great story about how it came together and why it is so powerful at Joining Techstars in Detroit.

My partners and I at Foundry Group – especially Jason – will be playing a role in this new program. Also, expect something really fun from us in the next six months. Hint – it’s something we’ve done before that I’m not sure any other VC firm has ever done – at least not that I’m aware of.

And – if you missed it, Techstars also launched a new program with the Mayo Clinic in Rochester, Minnesota called Techstars++ with the Mayo Clinic. Look for a bunch of new Techstars++ programs coming, along with lots of interesting new startup communities in our future.


Jerry Colonna spent a few hours with me and Amy on Saturday at our house. Jerry is one of our closest friends on this planet so any time we get time with him is a treasure for us. It was a cold-ish, snowy, gloomy Colorado early winter day. Amy and I were pretty off-balance due to my blood clot so it was especially nice to be with him as he always helps rebalance us.

We talked some about his new company Reboot. I’m a huge supporter of Jerry’s work – recommending many of the CEOs we work with to him, or his associates, for coaching. I attended a recent CEO Bootcamp as a special guest and it was amazing – I recommend it to every CEO.

Jerry mentioned that the recent Reboot podcasts were doing great and really fun. I noticed this morning that the podcast he did with Rand Fishkin, another close friend, titled #7 Depression and Entrepreneurship – With Jerry Colonna and Rand Fishkin, came out today. So I read the transcript (I can read a lot faster than I can list) and thought it was dynamite.

As usual, Jerry goes deep and intimate – very quickly. So does Rand – total, extreme, full transparency. Enjoy!


I’ve had a powerful exchange via email with Mario Cantin over the past few days. He pointed me to a post he recently wrote titled Empathy is feeling *with* others and an amazing three minute RSA Short video on The Power of Empathy by Dr Brené Brown. It’s stunning crisp and enlightening.

Amy and I are huge believers in empathy. In our book Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur we come back to this idea over and over again as one of the biggest challenges in communication between people.

Thanks Mario for sharing this with me.