Jun 17

Decentralized VPN – Zero Knowledge Systems v2.0

Before there was TOR there was Zero Knowledge Systems, they were a privacy network that let you set the number of hops you’d like to make before exiting as well as a simple system to manage multiple online identities. Sadly, they were not a commercial success, but they were an early cypherpunk company.

There is a now an open source project that hopes to bring a privacy VPN to the market using cryptocurrencies to pay for the solution. Mysterium just did an ICO (initial coin offering) arnd raised over $14M USD for development.

This is interesting for a couple of reasons. First, it is a direct throwback to a late 90’s failed cypherpunk idea. The question is are there now enough privacy conscious people out there willing to pay for such a service? If there are then maybe this time will be different.

The second is that they are going head-to-head with a free service that is trying to provide the same benefits. From their competitive matrix it seems their belief is that by putting an economy behind this they will be able to provide a faster service that TOR.

It is certainly true that TOR is slow, but the question is will be people willing to pay for privacy, especially if it is on metered usage instead of a flat fee. I’d be skeptical since I think the cognitive overhead of micropayments is why they haven’t been adopted and this feels similar to me. Anytime I have to think about whether or not to use a service it creates barriers, this is why most VPN providers have some sort of fixed pricing model, at least for “normal” usage.

This is one of those time I hope to be proven wrong. I’d really love a decentralized VPN to get wide scale adoption. Once I get my new high speed FIOS connection this month I may even try to run a node for a while to get a better feel for the project.


Jun 17

Back in the Saddle


Wow, more than a year. A lot has changed. I’m at a new firm: Evolution Equity and I’m expecting a kid in September. I’m super excited about both.

To start the job I’m going to do a couple deep dives to create a new investment thesis. I’ll be focusing on cyber security and dabbling in the block chain.

Finally, I’ve decided to try to blog more. To do so I’m going to write a bit more informally and try to publish faster. No promises. But here we go.

Feb 16

Honeymoon Reading

I’m just back from 14 days in Thailand. It was beautiful and relaxing.

2016-02-16 18.11.17 2016-02-16 18.09.31

While we did a whole bunch of amazing things during the trip like visiting temples and eating amazing food. I also had a lot of time to restart my meditation practice and read.

The Girl in the Spiders Web – Fourth book in the Girl With the Dragon Tattoo series, but not written by Stieg Larsson. A good book on its own merits, but continuity breaks with the original three made it less enjoyable. I understand what people mean when they say the magic is missing.

On Strange Tides – A really great pirates and voodoo magic novel. I’d never read anything by Tim Powers before, but that’s a mistake I’ll remedy. If you want something that is like Pirates of the Caribbean, only a ton better, grab this.

V for Vendetta – Never saw the movie, but this story of authoritarian regimes spying on society feels extremely relevant today.

The Atrocity Archives – I’ve loved Charlie Stross’s short stories so I finally got one of his novels. Supernatural spies. Fun stuff.

Nothing Like it in the World – The building of the transcontinental railroad is a fascinating story of epic proportions. It is hard to imagine today a project of that scale. Maybe SpaceX comes close.

Having the luxury to unplug and read was great, especially since I feel re-energized and ready to tackle big projects.

Aug 15

My Secret Email System: The Simple Trick That Changed My Life

I’ve finally found an email system that works, and I can prove it. Using the same tool I wrote about in my War On My Inbox post, we can see that I’ve shaved about 10 hours off my response time while increasing my percentage returned.

Screen Shot 2015-08-04 at 12.04.25 PM

So there are a couple of parts to my new system, one high-tech system and one simple trick.

The first piece to my achieving Inbox Zero almost daily is a new inbox system. Andreas Klinger showed this life hack back in 2013, it is by far the best email system I have ever tried. You’ll want to read his post to get the details, but he sets up multiple inboxes so that your page looks like this:

On the left is his empty inbox and on the right are all the messages he has flagged as needing some sort of attention. The single biggest key for me was to turn on the feature that automatically loads the next email instead of sending you back to the index. This makes it much more likely that you’ll process “just one more” and you don’t waste time scanning the index to pick the next email to process.

Using his system I can efficiently get to Inbox Zero every day; it has been a game changer.

The second system is decidedly low-tech; after reading about some studies that showed that simple physical reminders greatly improved productivity I made this todo tracker:

2015-08-04 13.14.51


I flip up the paper clip from todo to done each time I finish a task; it makes a very satisfying click. And the paper clip with the green rubber band, that one represents getting to Inbox Zero.

The physical system has really made all the difference for me. With a glance I can see how productive my day is so far, and it motivates me to get things done. My system works well with my desk setup, but one could use almost anything to track work done. Moving marbles from one bowl to another, or marching action fiction across the desk. Really you’re only limited by your imagination.


Jul 15

How to Live in the Future – My 4 Experiments


The future is already here — it’s just not very evenly distributed. – William Gibson

I love that quote so much that I have it inscribed on my wallet; it’s custom work done by Moxie & Oliver.

I want to try an experiment, I want to live in the future. To do that, I’m trying to find those pockets of the future that exist today, and try them for myself. These are things that could be mainstream in 5-10 years but are niche today. I’ve already written a post about the Amazon Echo. I’m also trying the Apple Watch, and some lightbulbs controlled by an App.

Now I’m looking for ideas. What else can I do to live in the future. Here are some that I’ve thought of.

  • 23andMe – Map my genome. Not sure what to do with it, but mapping it will probably be common in the future.
  • Smart home stuff – Philips Hue, Amazon Echo, and maybe a Nest, though they aren’t really practical for apartment living in NYC.
  • Soylent – I am not really a believer in this, but I may give it a try.
  • Tesla – I want to rent one for a road trip and see how the charging stations really work.

What else? Well, I’m hoping you’ll tell me. What other experiments should I be running?

Jul 15

Amazon’s Echo: The Interface for the Digital Home?


I’ve been using my Amazon Echo for a couple of weeks now and here are my thoughts.

  • It was the first device I made sure was working after my move on Sunday. That was a bit of a surprise to me since I wanted it working more than my Apple TV.
  • I’m listening to more music. I used to stream music through my Apple TV, but that required Spotify & turning on my TV.  Now all I have to do is ask for music.  This feels magical.
  • NPR –  I love NPR’s Marketplace. I used to listen to it on my drive home from work when I lived in San Francisco.  For some reason I don’t like it as a podcast during my subway commute though.  Now I play it as I get ready for bed.
  • I don’t use the App and hence the shopping list hasn’t worked for me.
  • My fiancee delights in asking Alexa random questions…

“ What is the capital of Puru?”

and trying to trick ‘Her’.

“Alexa, are you smart?”

  • She recently discovered this list of questions on Reddit, some are really funny.
  • I find myself asking about the weather a lot as well.

I think Alexa could become the operating system or interface to a connected home.  I already want her to be able to turn on my TV, to play shows and dim my smart bulbs. It may be the reason I go get Phillips Hue bulbs.

I hope Amazon opens the API and keeps working with IFTTT to add more functionality. I know they just launched a fund to back companies that are creating applications around their platform and I think this could be a killer app for them. Speaking to your smart home just feels like a magical interface and Amazon really got this one right on the first try. It is like living in the future.

Jun 15

The Traction Cycle: Why Sectors Become Hot In Venture Investing And Who You Should Raise From

virtuous cycleI’ve said many times that traction is how venture investors get comfortable with sectors they don’t have experience in. When you’re raising early stage capital from angels or seed funds, it is easier to raise from people who understand your business; that usually means people with experience in the space.

If an angel or VC doesn’t have experience in a sector it is difficult for them to know if an idea is good so they fall back on traction. This is why every demo day pitch has a slide with a graph going up and to the right; they are trying to demonstrate traction of some kind.

This also explains why sectors become hot in VC. Once one company starts to do well, the number of VCs who have dug in and now have some level of experience with the sector increases. Take Uber for example, after more than five rounds of funding there are plenty of VCs who have experience with the on-demand space. That makes investing in companies that are “Uber for X” easier for those investors.

If you are in an established category, finding venture investors that are familiar with your space will be relatively easier than if you’re attacking a area that most people don’t have experience in. If you don’t happen to be in a well-understood sector, look for investors that have some background in your space since they will require less traction and proof points to get comfortable with your business.

Apr 15

Virtual Fireside Chat

I’m doing a fireside chat with Zach from ReplyAll. It is ongoing, so you can either check back here, or get a notification when it has been completed.

Mar 15

Life is a Game of Skill: In Zero to One is Peter Thiel is Half Right

Zero to OneIn Zero to One Peter Thiel states that your life isn’t a lottery ticket and goes on to make the case that skill and not luck is behind great achievements. And while I agree with a lot of what he says, I don’t believe that luck and skill are mutually exclusive. A game of luck is one in which you can’t lose on purpose; an example is a lottery, once you’ve bought the ticket there is no way for you to lose on purpose. Contrast that with a game like poker where one can lose on purpose if one wishes.

By that definition, your life is a game of skill.

So in this I agree with Thiel, but it is the next step where I believe we part ways. In his book he argues that skill is the dominant factor and he stories about people like Elon Musk and Steve Jobs to back up this claim. He also mentions people who believe luck is dominant; after mentioning folks like Bill Gates and Warren Buffet he decides to ignore their opinions that luck plays a large factor. Without taking anything away from the brilliance of the people who believe skill is dominant, I think it also behooves us to recognize that good timing and luck also play huge roles in their stories. Skill and hard work can make you a millionaire, to become a billionaire you have to get a bit lucky.

I see two benefits to this worldview, the first is that it says that hard work is rewarded and we can take credit for some of our success, but it also tells us to be humble around our greatest achievements since there are probably external factors that have helped us along.

Mar 15

Seedcamp Podcast

Carlos brought the latest batch of Seedcamp companies by the office on Monday, they are an impressive group, and afterwards we sat down and recorded an episode for his podcast. In it we discuss a bit about my background, security funding, technical founders, and the CTO summits; it isn’t too long at 24 minutes. I hope you enjoy it.