Brad Feld

Category: Technology

Let’s start with my bias. I love Twitter, use it all the time (a lot more than Facebook), and will continue to love and root for Twitter.

I’ve been a Twitter for Mac user for a long time. I know it’s out of favor with all the cool kids, but it works for me.

It sits quietly on the left side of my giant screen and whenever a little dot shows up next to the second icon (I think it’s a tilted bell) I know I have something that has @bfeld in it that I should look at or respond to. And, when I feel like tweeting something, the app is right there on the left side of my screen.

Last week when Twitter for Mac was upgraded to raving from folks like Cult of Mac in their post Twitter for Mac doesn’t suck anymore I was psyched to install the update from the Mac App Store. So I did.

Here’s the problem. Suddenly refresh no longer works on the notification page (second icon). Now, when there’s a little dot there, I have to click the first icon (Home) and then the second icon (titled bell).

Sadness ensued. I presume that this has already been reported to gang at Black Pixel. I was hoping this would get fixed in version 4.0.1 which came out yesterday. But it didn’t. So here’s hoping for 4.02.


The first time I experienced someone accidentally wiped out a full set of data was on an IBM PC with a Tallgrass  Hard Drive and Tape Backup. I was at PetCom Systems, my first real job. It was a Friday evening and I was the only person around. The phone rang and I answered it, “PetCom Systems, how can I help you?” It was a user from somewhere who was trying to back up for the weekend and didn’t know what to do next. I asked her what she had done. She walked me through what was on her screen, which basically said “Are you sure you want to delete all the files on your disk.” She had already pressed Enter in a panic, it had finished whatever it was trying to do, and her PetCom software (and nothing else) worked anymore. She had somehow, from within Tallgrass, wiped out all the files (except for DOS) on her drive when she was trying to make a backup.

I told her what I thought had happened. I was 17. She cried. She told me her boss was going to fire her when he found out. She cried some more. I tried to say something soothing but I didn’t really know what to say. She eventually stopped crying, told me thanks for trying to help (I think she knew I was 17) and we said goodbye.

I went into the bathroom and threw up.

Since that time, I’ve typed some version of del *.* and answered Y more times than I’d like to think. I became good friends with Norton Unerase. After deleting the wrong directory a few times in the mid 1980s, I started always typing the full path name when I wanted to delete a directory. After doing this wrong a few more times and having MS-DOS eat files I wanted, I started making a backup before I deleted a directory. At some point I became pretty paranoid about backups.

And then I got casual again. About five years ago I decided I didn’t really care about any of the data that I had and if it all went away, I’d be fine with that. Fortunately, I’m not responsible for any data at work so I can’t really do any harm there. The only data that really matters to Amy are her photos so I’m extra careful with them (and have plenty of backups).

As I started down the Great Photo Organization of 2016, I made a backup. Yay. As I fell in love with Mylio, I gave myself the illusion that it was backing things up correctly because of its “Protection” approach.

Early yesterday morning, I set up Mylio on Amy’s computer, feeling ready to get her rolling with it now that I had organized 22k+ photos and was very happy with them. I installed Mylio, set it up, pointed it at the photo directory, and hit Enter. It did something different than I thought it would (and that it had done when I added on my second computer – or at least I think it was different.)

I then tried to set it up correctly again, the way I wanted. It created a second photos folder in Amy’s instance of Mylio and started adding all the photos to the library again, doubling the photo count. I highlighted the first folder in Mylio that I had set up and hit delete. I told it to only delete from this local computer. However, I’d pointed it at the Dropbox file share of our photos.

Two minutes later as one folder was counting up and the other was counting down, I realized I’d fucked myself. My heart rate and blood pressure went up and a giant “Fuck, fuck, fuck!” emerged from my lips.

It took me about ten minutes figure out what state things were really in and how bad it was. I knew I had a backup pre-organizing folders, so my worst case was that I lost four hours of moving files around from folder to folder. Mylio grinded away for about 30 minutes synchronizing all machines to the same state, which was one where there were no photos anywhere.

Amy said soothing words to me during this stretch of time. She had only asked me 351 times the previous few days if all her photos would be ok, so I put her behavior in the heroic category. Heroic calmness. “I feel bad for Brad” was soothing said by her, instead of “You fucking asshole – you deleted all our photos!” which would have been appropriate for her to say.

After everything settled down, I went into Dropbox, clicked on Deleted Files, and clicked on Restore next to the folder that said “Photos.” Dropbox is happily doing its thing, giving me back the four hours I might have lost.

Dropbox wins today. You get huge karma points for saving my bacon without me really deserving it. Thank you.

Mylio – you need to clean up a little of the UX around Dropbox.

Brad, ok, you’ve blown it once – be more careful now.


From the comments, tweets, and emails I got on yesterday’s post My Travels In Digital Photo Organizing Hell it appears I have a common problem. Basically, the existing photo approaches – in general – have created a massive mess. Apple and Google have just made this worse by continuously changing their underlying tools and approaches.

Buried deep in the comments was one from Darla DeMorrow. And it’s a gem.

“Hey, Brad. You’ve got a better handle on this situation than the average bear, but it’s still tricky, no matter what platform you use. And guaranteed it will change tomorrow, which makes us all crazy. But I’ve found a solution that I can recommend to my clients, who depend on www.APPO.org professionals like me to keep them sane. Check out www.Mylio.com. It’s a cloud-enabled service (not cloud-based) that allows you to organize in your own space, sync across devices, and only store in their cloud if you want to. It’s platform independent, sort of like the Evernote of photo organizing. You can throw stuff in the photo pile (making you happy), and it will automatically organize, to a point, making Amy happy. I’m happy to talk with you if you want to know more. You can find me online.”

I’ve been playing with Mylio for about 90 minutes on my Mac and iPhone. So far it is amazing – basically what I was looking for when I started this journey.

All my photos are still in Dropbox. I can access them, move them around, edit them, do whatever I want from a beautiful UX. Amy will be able to run this app on her Mac independently but see the same photo store and do whatever she wants. There are numerous backup options that preserve the directory structure and do NOT force me to use the cloud. I can sync with all my devices seamlessly. It knows how to import stuff like my Facebook photos, Aperture, and iPhoto. It works with Lightroom. It’s extremely fast.

It’s not free but I’m happy to pay for something that actually works. Thanks Darla!


I’m three days into trying to figure out the best way to deal with our large collection of digital photos that have accumulated since 2000.

When I started (on Christmas Day – I figured it was a one day project) Picasa said we had around 35,000 photos. After several different clean up approaches, we now have about 15,000. That’s the power of Duplicate Photos Fixer Pro which has been probably the cleanest and most straightforward part of this whole exercise.

But – let’s start from the beginning. Several years ago I created a shared Dropbox folder for me and Amy and moved all of our many folders of photos into one folder in Dropbox. I didn’t try to organize anything then – just get them all in one place. I then installed Picasa on each computer, spent a little while with Amy figuring it out, and let time pass from there.

Amy spent a lot of time over the past few years cleaning up photos, arranging them in folders, and copying things from place to place from within Picasa. We had various applications, like Dropbox and iTunes, set up iPhone sync directories. We avoided iPhoto, but every now and then it opened up somewhere and did something. Amy would sync her digital SLR photos with Picasa and then move them around. A bunch of other stuff probably happened in the background as we connected Picasa to the web, installed various Google apps on our machines, and I had a brief foray into using an Android phone.

However, I mostly ignored the problem. Every few months Amy would get frustrated looking for a photo and ask if I was ever going to clean everything up. We constantly talked about getting our iPhones set up to share stuff in a useful way. I bought Amy a new camera (the Sony A7) and decided as part of it I was going to clean up the mess that I’d help create over the years.

I vaguely remembered installing a Google Photo uploader thing on my desktop at work several months ago and letting it run for a few days while it uploaded the mess of photos we had. I looked at https://photos.google.com/ and scrolled through a huge photo collection. Yup – it uploaded them, although preserved none of the folder hierarchy Amy had painstakingly created. And then I started noticing lots and lots of duplicates. That’s weird – I wonder how that happened. After poking around for a way to have Google just automatically eliminate them, I discovered no such feature existed. Ok – I can delete a bunch of duplicates – let’s just share all with Amy. Oops – no way to do that.

Well, that would have been too easy. So, I spent most of Christmas Day afternoon using Picasa to clean up all the folder hierarchies, move photos from the hundreds of randomly named (usually with a date) folders, or the folders named “Move These Later 7.” I started as a Picasa novice and now have mastered it, with all of its quirks.

And then I realized there we had nested folders of duplicates spread out all over the place. Aha – now I knew why Google had duplicates everywhere. After a few searches, I found Duplicate Photos Fixer Pro and, after making a backup of the gigantic photo folder (via the web – so there was no web to desktop to web traffic), I quickly reduced our photo collection by over 50%.

I went to bed and let Dropbox and Picasa do their thing as everything synchronized on my painfully slow home Internet connection (there’s nothing like seeing a “10 hours left” message to decide to call it quits for the night.)

When I woke up yesterday, Dropbox looked fine but Picasa wasn’t synchronized. After messing around with Picasa for a while, I decided to just unlink the scanned folder (which was just the high level photos folder) and let it reindex. That worked. I messed around with the Dropbox hierarchy some more to try to clean things up. I noticed that Picasa again got out of sync. After doing this a few times, I started reading about Picasa on the web and my soul was crushed. I had a fantasy that the long term solution for everything could be something that lived on top of Dropbox, but as I realized that Picasa was getting old and stale (it shows in the UI) and there was a pretty clear path for Google toward everything being entirely web, Android, and Google+ (or – well – Google Photos) based. In other words, Picasa isn’t likely a long term solution.

Deep breath. At this point I checked with my partner Ryan who has 10 zillion photos and he quickly responded Apple Photo plus iCloud Photo Library (iPL) with a backup on Google Photos.

So I spent the rest of yesterday getting my mind around Apple Photos including a multi-machine and user struggle to understand the implications of what Apple thinks a family is and what can be shared between family members. Of course, the relic of the Apple iPhoto library didn’t help, as it introduced a new wave of duplicates which Duplicate Photos Fixer Pro figured out. Eventually I realized I had about 20 remnant Picasa temp files, each which were getting indexed in Apple Photos, so I hunted down and expunged them all. I started a bunch of folders uploading (I was trying to create some semblance of an Album structure). I was getting the hang out it, but it was dinner time so I was done until the morning.

When I woke up this morning, iPL told me that it has 11,781 files left to upload. Amy and I went out to breakfast. When I got back 90 minutes later, iPL now only had 11,721 files left to upload. Well – that’s not going to work.

I gave up, deleted all the photos from my instance of Apple Photos that was uploading, and read a draft of Eliot Peper‘s newest book Cumulus, which was awesome. I did a few other things, had dinner, and am still waiting for Photos/iCloud to figure out what it’s doing several hours later.

For now, I’m taking a break as I ponder my next move. Suggestions welcome.


When I think of geniuses who inspire me, Stephen Wolfram is near the top of the list. I’ve never met him but have followed him from a distance since I was introduced to Mathematica in grad school in the late 1980s.

Backchannel just published a a long, detailed exploration of the life of Ada Lovelace and her work with Charles Babbage that Wolfram wrote a few weeks ago. It’s awesome. By going through a lot of original source material, Wolfram formed his own view and discovered a number of things, including that the common reference to Ada Lovelace as “Enchantress of Numbers” is incorrect – Babbage actually referred her as the “Enchantress of Number” (9/9/1843 – letter from Babbage to Lovelace.)

In his article, Wolfram uses the Difference Engine and the Analytical Engine as the focal point to undercover and explain what Ada Lovelace actually accomplished. He pieces together Lovelace and Babbage’s history and relationship to each other. He extrapolates their work and places it in clear historical context. And he states his conclusions about who made which contributions.

His writing is magnificent. I’ve read some of it in the past and tried one summer in Alaska to get through his epic book A New Kind of Science (with very little success, although I read a bunch of science fiction and all the Barry Eisler John Rain books that summer.)

Buried deep in the article are a number of gems. One that jumped out at me was:

“Ada seems to have understood with some clarity the traditional view of programming: that we engineer programs to do things we know how to do. But she also notes that in actually putting “the truths and the formulae of analysis” into a form amenable to the engine, “the nature of many subjects in that science are necessarily thrown into new lights, and more profoundly investigated.” In other words — as I often point out — actually programming something inevitably lets one do more exploration of it.”

followed quickly by:

“representing mathematical truths in a computable form is likely to help one understand those truths themselves better.”

There’s a lot more like this. I encourage you to read the whole article slowly and thoughtfully as it’s a delight. But, if you want the punch line:

“Today, with computers and software all around us, the notion of universal computation seems almost obvious: of course we can use software to compute anything we want. But in the abstract, things might not be that way. And I think one can fairly say that Ada Lovelace was the first person ever to glimpse with any clarity what has become a defining phenomenon of our technology and even our civilization: the notion of universal computation.”

Last November, I read a number of biographies on my sabbatical including Ada’s Algorithm: How Lord Byron’s Daughter Ada Lovelace Launched the Digital AgeHere’s what I wrote about it then:

“I’ve read lots of articles on Ada Lovelace, but I’ve never read a comprehensive biography. The story was fascinating, especially when pondering what life much have been like in Victorian-era England and how much of any uphill cultural battle Ada Lovelace had. While we’ve got lots of challenges around gender still in our society, we’ve definitely made read progress in the last 150 years. This linkages to Lord Byron, Lady Byron, and Charles Babbage were fascinating and, in many ways, disheartening. Ada Lovelace was clearly a genius – I can’t even begin to imagine the amazing stuff she could have done if she was born in 1990 instead of 1815.”

Wolfram’s summary of what Lovelace might have accomplished if she hadn’t died so young (36 years old in 1852) was much more detailed and eloquent, but seems very consistent to what I have accumulated in my head. And I loved his conclusion.

“But the challenge is to be enough of an Ada to grasp what’s there — or at least to find an Ada who does. But at least now I think I have an idea of what the original Ada born 200 years ago today was like: a fitting personality on the road to universal computation and the present and future achievements of computational thinking.”


A few days ago, I noticed that my MacBook Air fully charged battery life had suddenly gone from around seven hours to under two hours and the fan was going full speed.

This has happened in the past and I couldn’t remember what I did to fix it. I blew it off for a few days until I got tired of having to plug my computer in every few hours. A quick look at Mac Activity Monitor showed me that Google Chrome Helper was eating up all my CPU (often at 100%) and subsequently crushing the battery life.

A search on Google didn’t turn up anything terribly satisfying. I found lots of complaints, a few suggestions to turn of automatic plug-in loading, and lots of “hey Google, fix this” dating back to 2011. Buried somewhere in one of the threads was a note to try clearing my browser cache.

Clear Google Browser Cache

Of course, there is no “clear browser cache” option any more, but there is now a “hamburger menu: More Tools: Clear Browsing Data” option.

That solved it. I saw over seven hours of battery life today. No fan. Simple, but buried.

Some day all this shit will just work. Well – maybe not.


When I was 14, my dad gave me a copy of Alvin Toffler’s book The Third Wave

It blew my fucking mind.

I then read the prequel – Future Shock – which was good – but since my mind was already blown, it was anticlimactic.

If you don’t know the arc of Toffler’s waves, they go as follows:

  • The First Wave: agricultural society
  • The Second Wave: industrial society
  • The Third Wave: post-industrial society

Future Shock was written in 1970 and The Third Wave was written in 1980. While the idea of post-industrial society seems obvious in hindsight, in 1980 it was a completely new idea.

Ever since then I’ve been wondering what the next wave would be. While Kurweil’s The Singularity Is Near is probably the closed book I’ve read that stimulated me the way The Third Wave did when I was 14, at some point I just felt hollow and disappointed when I read the latest futurist manifesto. Instead, I ventured further into the future with the science fiction that I have always read on a regular basis and used it as my stimuli.

Recently, a bunch of smart and famous tech entrepreneurs have been talking about AI and the impact of AI on civilization. I’ve read a few of the books that get tossed around, like Bostrom’s Superintelligence, and a bunch of the articles that people have written. But none have spoken to me, or blown my mind the way Toffler did 35 years ago.

I’m on a search for the “Third Wave” of this generation. Any ideas for me?


I spent the day yesterday doing Denver Startup Week stuff. I was on a bunch of panels and during one of the Q&A sessions someone asked something to the effect of:

“Now that things are moving faster than ever before, how do you deal with / keep up with them?”

I thought about it for a second and responded that I wasn’t sure the assertion was correct. I don’t think things are moving faster than ever before. I paused to make sure I believed that. Then I continued with my answer.

I was a freshman in college in 1983. It felt like things were moving at an extremely fast pace. I started my first real company in 1987. The pace of things was incredible. After I sold my first company, I started a company called Intensity Ventures to make all my personal investments from. The name kind of says it all. When I started making venture capital investments in 1997, the pace of things, and the amount of work I did, was massive. In 1999 things were moving so theoretically quickly that everything was a total blur.

After riffing on this for a while, I suggested we approach it differently. It’s not that things are moving faster, it’s that information is much more available and there’s much less friction around communication. My communication mechanisms in 1983 were a landline telephone, letters, newspapers, magazines, and an airplane. The only constant in that equation 32 years later is the airplane, and as far as I can tell it takes about the same number of hours (six) to get from Boston to San Francisco that it did in 1983.

By 1987 I was regularly using faxes and Federal Express (the only overnight mail I was aware of), but a mobile phone and email didn’t really show up until around 1993 for me. The web appeared in 1994 and a completely different method of communication started its long march into integrating in our universe.

While all of this was different, the pace of things – at least the intensity of how work got done – didn’t feel much different. I was young and had a huge amount of energy and ambition, so 100 hour work weeks were typical. Redeyes were the norm for me as I wanted to spent the least amount of waking hours on airplanes. By 2001 when the Internet bubble burst, I was completely exhausted, and then I began a relentless grind for several years of cleaning up the mess I had created, followed by another relentless grind of working to get Mobius Venture Capital into a steady place and ultimately starting Foundry Group.

I never once felt that things were moving slowly. Instead, as time passed, my approach to communicating with people changed, although lots of humans in my world still want to get together face to face or fly to meet me for 30 minutes when a video conference would be perfectly adequate.

But more significantly, when I calmly observe the world around me, we want to feel, like every other generation, that what we are facing right now is more complicated, more important, and changing faster than ever before in human history.

On an absolute basis, it might feel this way because of communication mechanisms. But if you take the first derivative, I think you’ve got a flat line, as the relative pace (when normalized for communication mechanisms) feels constant to me, at least during the 1983 to 2015 time period that I’ve experienced as an adult.

Remember – All this has happened before and all of it will happen again. Ponder this the next time you get on an airplane, even if it has WiFi.

Agree or disagree?


As I read about the unveiling of the Tesla Model X, I have two thoughts. The first one is “I want” (hint: Amy – you need to replace your red Range Rover.) The second is that price of admission is an amazing product.

Indulge me while I go on an amazing product rant from our portfolio.

  • Glowforge is turning 3D printing inside out by using a laser to cut and engrave, instead of an extruder to, well, extrude. They just crossed the $4 million mark in day five of their thirty day pre-order campaign.
  • Sphero has sold more BB-8’s in the month since they launched than even I thought possible. I have one on my desk and it gives me joy every day I’m in the office.
  • Accenture just launched their Connected Analytics Experience’s immersive environment which is enabled by Mezzanine. As a daily user of Mezzanine, it actually makes video conference and collaboration tolerable.
  • The demand for the 3D Robotics Solo drone is off the charts.
  • Rock Band 4 comes out next week. Yesterday two new U2 songs were added as exclusives. Enough said.
  • We closed an investment yesterday in a company that will announce next week. I’ve been using the product for sixty days along with their competitor’s product. Their competitor has raised 10x the amount of money so far (prior to our investment), and the product from the company we invested in, from my own head to head comparison, is amazing, compared to the “meh” product from its competitor.
  • We are issuing a term sheet today to another company that I hope accepts our offer. Your mind simply explodes when you use this particular product.

I could keep going but you get the idea. When I reflect on our successful investments, regardless of the form factor (software or hardware or both) that they take, they all are amazing products. And the founders come from a product first mindset – their goal is to unambiguously create the best product that delight users every time they come in contact with it.

I’ve heard the discussion about how important product is for over 20 years of being an investor. But it’s not important anymore. Instead, an amazing product is simply price of admission. If you don’t have an amazing product, you don’t get to play, at least in my little corner of the world.