Brad Feld

Category: Things I Like

I recently decided to back three graduates on Upstart. In this new model of crowd-funding, accredited investors back entrepreneurs and have the option of signing on as mentors. In exchange, the “upstart” gives up a percentage of their future income over the next 10 years. FYI – I’m not an investor in Upstart, but I am a big fan.

The common thread with the upstarts I’ve backed is their passion to cross art with technology. Chris Mathews, Bennett Lin and Shefali Kumar Friesen are all highly-focused on their interdisciplinary efforts, applying art and music to technology to solve today’s problems.

Shefali asked me if I knew anyone interested in art and technology who might want to help her reach her funding goal. I asked her to make the case, and she came back to me with the following video (posted on her Upstart profile).

[vimeo 57611714 w=400 h=300]

I think Shefali is awesome and I’m proud to be backing her. Join me if you can!

As investors, are we the modern-day patrons of the arts?


An email was forwarded to me this morning that had the following text in it (I’ve anonymized “The College” but it’s a large, well-regarded four year university.)

The College is Going Google! What does this mean? How will it impact teaching and learning at The College? Many K-12 school districts are using Google Apps for Education, providing their students with access to Google productivity tools as early as primary school. Students coming to The College in the next five years may never have opened Microsoft Word, but will be familiar with sharing, collaborating, and publishing with Google tools. Are you ready?

I spend time at a few universities, including MIT and CU Boulder. I’m teaching a class this semester at CU Boulder with Phil Weiser and Brad Bernthal called “Philosophy of Entrepreneurship.” We had our first class last week – Brad Bernthal led so Phil and I sat in the back. I noticed a bunch of students with their email open during class – almost every one of them was using Gmail.

A meme went around a few years ago that kids using Facebook would never use email and that Facebook would replace Microsoft Outlook and Gmail. This never really made sense to me, especially since I’d already heard that text messaging would replace email, and then I heard that X would replace email, and now it was going to be Facebook. As much as email frustrates us, it’s still by far the most ubiquitous comm channel.

But as someone who switched completely from Microsoft Exchange to Google Apps a few years ago, it seemed clear to me that Microsoft was going to come under incredible pressure on this vector. Office 365 was one of Microsoft’s reactions to this, but I still haven’t met any company that uses Office 365 as it’s primary infrastructure, although Microsoft has a nice site called NowOnOffice365.com that lists a bunch.

Now, it appears that Google is taking a page from the Apple playbook and focusing on higher education. Apple did this magnificently in the 1980’s when I was in college and did this again in the past decade. Jobs was always focused on universities – I still remember “computers are bicycles for the mind” and the 50% discount off of retail promotion that MIT had in 1984 or 1985.

I don’t focus on market share dynamics (I’m sure there are teams of people at Microsoft and Google focused on this) but the anecdotal evidence I’m seeing is powerful. And when The College switches to Google Apps because the students coming to The College are already well steeped in it and “may have never opened Microsoft Word”, something really interesting is going on.

If your organization is on Office 365, I’d love to hear from you in the comments to understand how you are using it. Are you using document collaboration via SkyDrive, or just Office 365 as the backend service for Email instead of Exchange?

If you are a college student using Microsoft Outlook instead of Gmail, tell me why.


I’m finding myself using Google+ more and more. I recently decided that the long game Google is playing is absolutely brilliant. They are being understated about it but doing exactly what business strategists talk about when they describe the long game as the one to play.

Rather than making a bunch of sweeping pronouncements, struggling to jam together a bunch of random crap in a big bang release, and then worry about staying involved in a feature race with a competitor, Google is continually experimenting with new functionality, rolling it out broadly in a fully integrated fashion on a continuous basis, and providing it as a core part of an ever expanding thing that is getting more and more useful by the week.

By now I hope you are saying something like “What the fuck is he talking about – Facebook is crushing Google+” or something like that. Yeah, whatever. That’s why it’s the long game that they are playing.

Here are some examples.

I live in GmailSuddenly, I found this magical thing called Circles to be useful. When I get behind on my email, I simply go through a few of the circles (Foundry, Foundry Ents) and clear the email from my partners, my assistant Kelly, and the CEOs I work with. I have persistent chat up – I find that 80% of my chats now go through Gchat (the other 20% are Skype, and they are almost always requested by someone else.) And now that there are Hangouts integrated, many of these are videos.

Google Voice is my Phone NumberI used to have desktop phones. I don’t anymore – I have a Google voice # and an iPhone. I give everyone my Google voice #. It works everywhere. I never think about what phone I’m using anymore. And I do many calls via the computer.

Google Hangouts is my new Calendar Invite. I hate the telephone. Hate hate hate. But I don’t mind chat. And I don’t mind a Google Hangout / video call. All of a sudden I can make invites from Google Calendar that are Hangout invites. Done – every phone call / conference call is now a Hangout.

I live in ChromeI have several computers. I never notice the difference between them. I’m downstairs at my place in Keystone right now on my Macbook Air. When I go up into my office, I’ll be on my treadputer with a different Macbook Air (an older one) connected to a 27″ monitor. I switch regularly between the two throughout the day and don’t even notice.

Now you are thinking “Ok Brad, but other than the Hangouts, Circles within email, and Hangouts within Calendar, what are you using Google+ for?” Just those three things have completely changed my workflow massively for the better. And they just showed up for me one day – I didn’t have to do anything.

In 2012 I used all the normal Google+ stuff. I reposted content there. I followed people. I occasionally chatted, commented, or +1ed. Facebook-like features. But I didn’t care that much about that stuff – yet.

All of a sudden I’ve got Communities. I’ve got Events. I’ve got Pages. And Hangouts, and Circles integrats seamlessly with each of these things. And they are nicely integrated with Gmail and Calendar. And suddenly I can do On Air Hangouts. And, I can record them automatically and save them to my Youtube channel. Keep playing for another few years, user by user, company by company, integrated feature by integrated feature.

Yeah, it drives me batshit that Google still things I’m brad@feld.com, brad@foundrygroup.com, brad@startuprev.com, and brad.feld@gmail.com. Some day they’ll integrate these. And as I approach 25,000 contacts, I’ll probably start bitching about how this limit is ridiculous, just like I did at 10,000. But I can deal with all of that.

Google – thanks for playing the long game here. I wish more companies, especially other tech companies, did this especially when they have massive resources. Sure – some think they are playing the long game, but they are really playing the short game with a bunch of things that take a long time for them to get out the door. Different game.


This is a tough time of year for a lot of people. I used to be one of them. And I’ve gotten over it, and myself, which I attribute 100% to Amy helping me figure it out and not being willing to put up with my nonsense. But it’s a useful reminder for those who think it’s awesome for everyone.

While the Christmas and New Year’s holidays can be a restful, restorative, wonderful family time, it can be excruciating for those who are depressed. It can be oppressive rather than restorative to those who are exhausted and worn out from the year. And for those who feel pressure from being immersed in their family, or who feel unresolved tension in their relationships, it can be a nightmare.

My struggle with this time of year is simple – I never had Christmas as a kid. I’m Jewish and my parents didn’t embrace the “ok – we’ll pretend like Christmas isn’t supposed to be about Jesus being born” so we never celebrated it. I recall existing in this parallel universe, where all my friends had this crazy gift foreplay for the month of December, talking about what they were going to get, running around with the parents getting things for their friends, and planning for the main event. It culminated in gift orgies on December 25th, wrapping paper flying, and endless gifts piled up to be played with, inspected, eaten, and traded.

I attended a few of these gift orgies at the invitation of my friends. I always brought over a nice gift for my friend and his or her parents. I always got something – usually one thing that was generic (that everyone got), or a book, or sometimes a piece of clothing. Occasionally, out of last minute mercy, the mother of my friend would scrounge up whatever extras they had, put it in a leftover stocking, and give it to me.

As I got older, I got crankier about it. My first wife celebrated Christmas so we did it at her house, with her family. They were polite, but they never liked me very much, so the whole think was this awkward charade, which just made things worse. I refused to have a Christmas tree in my apartment, so my ex-wife and I fought every year around Christmas for the few years that we were together. And that sealed the deal for me – Christmas sucked.

I then went through the “why isn’t everyone working” phase of Christmas. I was resentful that everyone took two weeks off. C’mon – there’s work to be done! I’d grind through my work, being newly productive, cleaning up all the cruft I hadn’t gotten to, as everyone else partied and had fun.

I can’t remember what Amy and I did for Christmas for the first few years of our relationship, but after we moved to Boulder we started spending it with her family in Western Colorado. They were extremely nice to me and included me in everything they did, but I still felt like an alien in the midst of a strange human ritual. I recall spending hours huddled over a laptop trying to figure out the cheapest way to get a dial-in connection to check my email, even though no one was sending me email because it was Christmas.

At some point I just accepted that I was grumpy at this time of year. Disoriented. Confused. Sometimes a little depressed. Usually just bored. Amy put up with it, but kept nudging me to try different things.

A few years ago I finally turned a corner. We started spending the last two weeks of the year at our house in Keystone. We’d invite a variety of friends up for a few days. The only Christmas celebration we had was Jewish Christmas, where we went out for Chinese food and a movie on Christmas eve. We’ve recently augmented that with sushi and a movie on Christmas day night. Instead of being grumpy, I just chill out. I enjoy hanging out with whomever comes to visit. I read a lot, sleep a lot, and catch up on a bunch of stuff – mostly writing – that I get behind on. And I get rested and ready for the year ahead.

It took me a very long time to figure this out. Maybe I’m slow when it comes to decoding Christmas, but I’ve got a bunch of friends who also struggle with this time of year. I watch from a distance as couples bundle up their kids, stick them on a plane, and make a painful, stress-filled visit to some distant city where one of them grew up. Or my single friends searching for something – anything – to do other than a trip to their parents. Or others, just defaulting into a trip to where they grew up, knowing it’s going to suck but feeling powerless to do anything about it.

It’s ok not to love Christmas. But that doesn’t mean you have to be miserable for the last two weeks of December every year. If you aren’t loving the game, change it.


There has been a cliche going around the last decade or so that goes “hope is not a strategy.” It inspired a book titled Hope Is Not a Strategy: The 6 Keys to Winning the Complex Sale and is repeated often by VCs in boardrooms when they are confronted with companies that are flailing, especially when trying to reach their revenue goals. I’ve been guilty of saying it a few times although it always left a funny taste in my mouth and I didn’t know why until this morning when I read a great essay (unpublished at this point) by Dov Seidman, the the Founder and CEO of LRN. In it Dov has a great punch line.

“No doubt you’ve heard the old business cliché that hope is not a strategy.  During the recent presidential election one candidate in fact said this very thing in an attack ad against the other. It’s an expression usually used to belittle someone and to exhort them to deliver a linear plan.  And while they are right that hope is technically not a strategy, inspirational leaders understand one final thing:  that without hope there is no strategy. “

He is so absolutely correct.

I’m an optimistic, hopeful person. I think things will turn out ok. I don’t deny reality and I live by the words of John Galt when he said “It’s not that I don’t suffer, it’s that I know the unimportance of suffering.” I suffer plenty, I have plenty of things fail, and I’m sure I disappoint a lot of people. But I never give up hope, never give up trying to do better, and never give up learning from my mistakes.

We are coming to the end of a calendar year that has had a lot of crazy, bizarre, hostile, and negative stuff in it, especially in the past two months. I measure my years by my birthday, so my new year started on 12/1 when I booted up v47 of me. I was in pretty rough shape physically and emotionally because of the preceding few months but I was on the mend and optimistic. Other than struggling through a nasty cold (which is clearly linked to a completely trashed immune system from a pile of antibiotics and the past few months of system stress) I’ve had a great few weeks with Amy, some friends, and very little travel.

As I look forward to the next year, I have a clear strategy – both for my work, my personal life, and my health. A bunch of friends have said mildly cynical things like “you say that every year” or “I just read the annual ‘Brad broke himself” blog post” – mostly in an effort to be supportive, but clearly with the view that no matter what I try differently each year, the outcome will be the same and I’ll melt down somewhere in October or November.

Part of the beauty of an annual cycle is the opportunity to try again. To revisit your existing strategy or to create a new strategy. To shift your mindset from “this is inevitable” to “having hope for a different outcome.” Now – if you only have hope, but no strategy, you won’t make any progress. But if you have a strategy, but no hope, you are dooming yourself to failure before you begin.

So take advantage of this time of year. Do whatever you need to do to hit reset. Purge your brain of all the angry, negative, cynical, defeatist crap. Accept that context in which we are living. Then, create a new strategy for yourself – for work, for yourself personally, for your relationship, for whatever, and inject a good dose of hope into the mix.

Do something new. And be extraordinary at it. Remember Yoda – do or do not, there is not try.


Skiing off of Polar Express
Skiing off of Polar Express

I love the emails I get from readers of this blog. Yesterday morning, I got the following from Shane Schieffer of FitTrip and I just saw it as I was grinding through my morning backlog from the weekend.

“Hi Brad, Happy holidays. My friend and I were watching Polar Express with our kids last night, and he commented on the impossibility of skiing down the top of a train towards the engine, even on a crazy steep slope. I know you like to geek out on software and things such as figuring out the algorithms behind slip numbers, how about physics? The question was bothering me so I took a shot at it this morning. Thought I’d share the result. I bet users of your forum could top my work, or find errors, or extend it to further interesting observations. Kind of a fun holiday geeky thing to contemplate, so I thought I’d send it your way.”

This reminded me of a great story from Amy. On her very first trip to Dallas from Boston to meet my parents, she was sitting on a plane next to a guy who was doing a bunch of math sheet of paper. She asked him what he was doing. He said he was calculating how much fuel the airplane needed to get from Boston to Dallas. It turned out to be a guy named Christopher Couch, who was an undergrad at MIT that had crossed paths with me for some reason I can no longer remember. She and Chris had a great time on the plane together talking about all kinds of nerdy things. The entire memory made smile.

Oh – here’s the answer.

“Assuming just the train engine (not cars, and cargo) that the polar express was modeled after, which weighs 361,136kg and has an approximate cross sectional surface area of 10m^2, at freezing (0-deg Celsius) and 1atm of pressure (sea level) on a -128.5 gradient (what the sign said in the movie which equates to a -52 degree slope) assuming frictionless tracks, and a hill tall enough to induce free fall, where no braking nor engine acceleration is applied, and the coefficient of drag is  based on a rectangular shape, the train would be traveling 1,434 mph. This is clearly much faster than the terminal velocity of a 6-foot tall man with a boy on his shoulders (say a combined 3m), standing up, weighing a combined 240lbs, with a cross sectional surface area of 2.25m^2, whose terminal velocity would only be 52.5 mph on that same slope. Of course the train itself would create a wind draft that would lessen the difference, but either way the man and boy are going off of the back end of that train.  Unless the man is a spirit…”


I spent two weeks without my iPhone. I was completely off the grid for the first week but then spent the second week online, on my MacBook Air and Kindle, but no iPhone. I got home on Sunday and have had my iPhone turned on the past few days. I’ve used it as a phone, but I’ve largely stayed off of the web, email, and twitter with it. Instead, I’m only done this when I’m in front of my computer. I played around a little with the new Gmail iPhone app (which I like) but I’ve been limiting my email to “intentional time” – early in the morning, late at night, and when I have catch up time in between things.

I don’t miss my iPhone at all. It sits in my pocket most of the time. Every now and then I hop on a phone call and do a conference call with MobileDay. I used it for a map. I checked my calendar a few times.

Yesterday, it occurred to me that I was much more mentally engaged throughout the day in the stuff going on (I had a typically packed day). I had dinner with my brother at night. No phones were on the table, no checking in to Foursquare, no quick scanning of Twitter in the bathroom while peeing. When I got home, I hung out with Amy – no email. This morning, I just spent an hour and went through the 200 emails that had piled up since 5:30pm when I’d last checked my email. My inbox is empty.

There’s some magic peace that comes over me when I’m not constantly looking at my iPhone. I really noticed it after two weeks of not doing it. After a few days of withdrawal, the calm appears. My brain is no longer jangly, the dopamine effect of “hey – another email, another tweet” goes away, and I actually am much faster at processing whatever I’ve got on a 27″ screen than on a little tiny thing that my v47 eyes are struggling to read.

Now, I’d love for there to be a way for me to know about high priority interrupts – things that actually are urgent. But my iPhone doesn’t do this at all in any discernable way. There are too many different channels to reach me and they aren’t effectively conditioned – I either have to open them up to everyone (e.g. txtmsg via my phone number) or convince people to use a specific piece of software – many, such as Glassboard – which are very good, but do require intentional behavior on both sides.

I’m suddenly questioning the “mobile first” strategy. Fred Wilson just had two posts about this – yesterday’s (Rethinking Mobile First) and today’s (A Blog Post Written On The Mobile Web). He’s coming at this from a different perspective, but it’s an interesting meme and thought process.

I don’t actually care about the hardware much – it’s going to evolve very rapidly. As is my way, I’m completely focused on the software. And I think the software is badly lacking on many dimensions. Since so much of the software is happening on the backend / in the cloud, we have the potential for radically better user interaction. But we are far from it.

Fred talks in his second post about living in the future. My future, five years from now, has my “compute infrastructure” integrated into my glasses. I no longer have a smart phone – I simply have glasses. I have no idea if I carry a device around in my pocket or have an implant, nor do I care. Again, the hardware will happen. But I don’t want to live my life having all my emails appears in my glasses. And I especially don’t want a tiny keyboard that I can barely see anymore being my input device.

I don’t know the answer here so I’m going to run a bunch of experiments for v47 of me. I’ll spend some months, like this one, with email turned off on my phone. I’m going to dig deeper into “cross channel” software that helps me deal with the flow of information. I may hack together a few things to help me manage it. And I’m continuing to shove more and more communication online – via email or videoconferencing – and away from the phone in the first place.

What’s missing is my control center. I’ve been looking for it for a while and never found anything that’s close, so I end up with a manual control center in my browser. Maybe I’ll stumble upon it – finally – this year. Or maybe I’ll create it. Either way, my smart phone is officially not working for me anymore.


Fuck You Kidney Stone

As they wheeled me into surgery, I thought to myself “If this is the end it has been pretty amazing.” This is a photo my brother Daniel took of me just after they wheeled me out of the recovery room and back into my little cubby hole where Amy and Daniel were hanging out. While I don’t remember any of this, probably due to being under the influence of Versed (a truly amazing drug) at least I had the right attitude in response to Daniel saying “take that kidney stone!”

I had an 8mm kidney stone removed using Laser Stone Surgery using Flexible Pyeloscopy on Friday 11/16. While not a major surgery, I still went under general anesthesia for two hours for the first time as an adult. Amy describes this as “they take you to death’s door, open it a crack, let you peer in for a while, and then pull you back and close it.” I probably didn’t need her to tell me that description prior to the surgery.

On Sunday 11/18 I went to Cabo San Lucas for a two week vacation which included my 47th birthday. I don’t remember much of the first week – I was stoned on Vicodin and in a happy, warm, cuddly, very constipated, fields of golden retriever puppy haze. I stopped taking Vicodin on Thursday 11/22 but it still took a few more days to start feeling normal. I dropped off the grid entirely for the week of 11/8 but resurfaced to do some email and writing the week of 11/25. By 12/1 (my 47th birthday) I felt about 90% and was very relieved to have the surgery, and the prior three months behind me.

This period started off on 9/5 in Kobarid, Solvenia with a bike accident. I broke a tooth, got some stitches, and badly bruised my ribs. It was entirely my fault and my partner Ryan McIntyre, who I crashed into, saved me from much more severe damage. I then proceeded to spend the next three weeks on the road, totaling a month away from home. That was mistake #1, as I underestimated how tired I’d get from it. Mistake #2 was underestimating the damage from the bike accident. I ended up running the Detroit Marathon on 10/21 and did fine, but I was completely wiped out physically by the end of October. I continued to spend a lot of time in October and November on the road and found myself exhausted and depressed by the end of it. And then our dog Kenai died.

Oh – and Amy and I wrote the bulk of Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur during this time period (it’s done – we submitted the final page proofs over the weekend.) I recognize the irony of completely burning myself out during the writing of this book – fortunately we talk about this challenge plenty in the book and we communicated extraordinarily well as a couple during this time frame about what was going on. Finally, I do have a full time job and spent the bulk of my time working on that, so all of this other stuff was the extracurricular activity that filled in the cracks around the 60+ hours a week of VC work I was doing during this time.

I had a lot of time to reflect on this last week after I came out of my Vicodin-induced haze. At 47, I realize, more than ever, my mortality. I believe my kidney stone and depression were linked to the way I treated myself physically over the 90 days after my bike accident. While the kidney stone might not have been directly linked to the accident, the culmination of it, the surgery, and my depression was a clear signal to me that I overdid it this time around.

I’m back in Boulder and very refreshed. I’m also determined to learn from this experience. Amy and I spent a lot of time last week talking about changing the tempo on some things, including adding in some new daily habits like yoga that prioritize higher than other things. And I’ve accepted that part of my travel pacing has to include being home over the weekends to so I can recharge my extrovert.

Thanks everyone who gave me well-wishes and support the past few weeks. It means a lot to me. I leave you with the sunrise from Cabo that I saw each morning during the past two weeks.

Smile - it's the morning


If you’ve been following along at home, you know I’ve had a tough fall. It started with a bike crash in Slovenia, followed by a few weeks in New York where I physically felt awful. Fortunately I was with Amy for her birthday (we celebrate her birthday for most of September), but I underestimated how long it would take me to recover. I ended the three week trip in San Francisco for my mom‘s 70th birthday, which was wonderful until I got a terrible stomach virus on Sunday morning. I can’t remember the last time I threw up – and as I somehow managed to get home that day, I’m sure I looked like warmed over shit. After a week at home I hit the road again around the release of Startup Communities and spent almost all of October on the road, reaching Boise, Oklahoma City, Chicago, Des Moines, San Francisco, Seattle, Detroit, Boston, Montreal, Toronto, Lexington, and Louisville. While I had a great time, ran a marathon in Detroit in the middle of it, and met a lot of awesome people, I totally shredded myself.

I got depressed. And then my dog Kenai, who I loved more than almost all the humans I know, died.

I turn 47 in a few weeks. I’m extraordinary lucky to be married to an amazing woman for 22 years. We’ve figured out how to have an awesome relationship in the context of an entrepreneurial life, and we are wrapping up a book on it that will be out in January. I have extremely meaningful work with three partners who are my best friends. I get to work with incredible companies and entrepreneurs every day. And I get to define how I spend my time.

But I’m totally and completely fried. And I did it to myself. I already spend 60+ hours a week working with the companies I’m an investor in. So – all of the stuff I’m doing around Startup Communities is extracurricular activity. Writing Startup Life, while super important to me, is an extra curricular activity. Travelling all over the place is part of my work, and I have a lot of fun doing it, but plenty of the places I’m going are extracurricular activities. I feel like I’m getting all of my primary work done, but I’m neglecting one big thing in the mix – me.

I’ve found myself in a similar position every year. This is nothing new for those close to me – I run extremely hot and often up to the edge of my capacity. I keep adding stuff on top with some fantasy that my capacity for new stuff is unlimited. There is so much I want to do and I just keep going after it. I have a good internal algorithm for making sure I get all the “urgent / important” stuff done and I’m very aware of what work to prioritize over other things. When I start reaching my capacity, I focus more on the important stuff – both urgent and non-urgent, and insert a tighter hierarchy around my work, making sure my partners and the companies I’m an investor in are at the top of the stack.

But I neglect me. And that’s what has happened again this year. My extrovert is completely used up. While I’ve got a few more commitments between now and the end of 2012, I’m resetting my priorities for the balance of the year and focusing internally, on me, my health, my physical self, Amy, my partners, the companies I’m an investor in, and the writing I want to do.

I’ve been through this before – well – about once a year for the past 25+ years, so I know how to deal with it when it happens, although I clearly don’t know how to prevent it from happening. Maybe I’ll figure that out in my 48th year on the planet.