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Hi, I’m Brad Feld, a managing director at the Foundry Group who lives in Boulder, Colorado. I invest in software and Internet companies around the US, run marathons and read a lot.

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A Problem With Gmail When The Machines Take Over

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In general, I love Gmail. While Amy likes to complain to me about how ugly it is, I don’t even see the UI anymore as I just grind through the endless stream of email that I get each day. My biggest struggle is figuring out how to keep up, without the email ending up dominating everything I do. In the past year, this has gotten a lot harder, but I continue to try new things.

That's a lot of email young man

Fortunately, spam is almost non-existent for me. We invested in Postini, which Google ended up buying, and it’s been a joy to have flipped a switch almost a decade ago and had spam go from “overwhelming” to “almost nothing.”

Every now and then, I get a flurry of spam from a new attack before Gmail figures it out. Today was one of those days – I had about a dozen things that looked sort of eBay notification like but with Arabic characters. So I hit ! and marked them each as spam as I was going through my inbox. Suddenly, my inbox reloaded and I got the following message.

But but but it's me!

I expect that by the time I finish writing this post I’ll have access to my inbox again. But stuff like this makes me physically uncomfortable – my morning routine was just interrupted and the machines decided I don’t get to access my email for a while.

While plenty of folks complain about the ambiguity and lack of precision around many of the issues surrounding Google apps, and more specifically the general lack of support, I usually don’t worry about this much. However, in the last month I’ve had two issues that caused me to remember that I’m increasingly less in control and the machines are increasingly more in control. This is one of them; the other was that I noticed an incredible slow down of performance of Gmail – just for me. After a week of pressing on it, the response from Google enterprise tech support was “you have too many things hitting IMAP – disable all of them.” A quick look at my Google Dashboard showed around 100 different apps that I’d authorized to access my account. I cut it down to about 30 – and got rid of several that I knew were high traffic that I liked, such as the awesome new Mailbox app – and things sped up again after 24 hours.

I recognize that if as we hand over control to the machines, they will make mistakes. That’s ok. But it’s jarring when one doesn’t have control over it, even for a little while. And yes, my Gmail is back up.

Modern Day Patron of The Arts on Upstart

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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).

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?

Evidence of Google Winning The Generational Shift Over Microsoft

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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.

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The Google+ Long Game Is Brilliant

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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.

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My Smart Phone Is No Longer Working For Me

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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.

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