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.

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?

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

Totally Crazy – My GF Got Her Dog to Let Her Into the Apartment

This just blew my mind today, I expect it will blow yours too.

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I fully expected to be going back home with my keys to let Jeannie in.


Oct 14

Are Newspaper Ads Really 25x More Effective Than Online?

I was working at DoubleClick back in 2000 during the dotcom bomb so I got to witness first hand as CPM prices crashed from $50 to $5.

In looking at CPMs today I found something that surprised me: newspaper CPMs are approximately 25 times more expensive than online ads.











That means businesses are paying a premium for static ads that are difficult to track. The only way that makes sense to me is if companies aren’t comfortable with the newer technology.

That might also explain why radio and TV are cheaper than their paper counterparts, it requires more technology and work to create a radio spot or TV commercial than a simple static Ad.

But, I’m a bit surprised by the fact that newspaper CPMs are so much more expensive than Magazines. Maybe it’s due to the fact that smaller papers have a tighter geographic focus and are therefore more attractive to local businesses?

But this 25x differential in pricing really can’t last. I expect that means that CPMs for traditional media are going to fall rather than online CPMs rising a great deal. This will be good for companies that buy advertising, but is only going to further injure traditional media.




Oct 14

POP – A Great Prototyping App

Last year I started teaching an entrepreneurship class at NYU Poly; while it has an official name we affectionally call it “Entrepreneurship for Hackers.” My co-teacher and I essentially teach tools similar to Steve Blank or the Lean Startup to engineering students over 13 weeks.

In our class on prototyping we cover a bunch of tools from crude sketches on paper to high fidelity mockups done in CSS. This is how POP, Prototyping on Paper, came to my attention. It is a brilliant way to do mobile mockups using only an iPhone; simply draw the app, take a picture, and then add links to sew your screens together and make a sample workflow.

One of our teams used this and I was really impressed with how simple yet powerful their prototype was. If you’ve got a great idea for an app this is a simple way to show it to your friends with only an hours work.

Sep 14

The Inner Game of the Boardroom


I’ve recently been reading the excellent book The Inner Game of Tennis; it is ostensibly about how to play tennis, but it is really about how to perform under pressure.

[T]he inner game. This is the game that takes place in the mind of the player, and it is played against such obstacles as lapses in concentration, nervousness, self-doubt and self-condemnation. In short, it is played to overcome all habits of mind which inhibit excellence in performance.

The book talks about how we each have two selves, conveniently titled Self 1 and Self 2 in the book. Self 1 is our conscious self, the ego; Self 2 is our unconscious mind that does most of the work in sports.

Trust the body to learn and to play, as you would trust another person to do a job, and in a short time it will perform beyond your expectations.

The book devotes a lot of time discussing how Self 1 talks to Self 2. If you’ve played a sport like Tennis or Golf then you’ve probably caught yourself saying things like “Play better.” At least I know that I often say things like “Come on Lucas, get it together.” That is Self 1 berating Self 2. What interests me most about this form of talking to myself is that I’d never speak to another person that way. If one of my teammates  in soccer made a bad pass I’d never say that to them, instead I’d offer positive encouragement. So why do I treat myself worse than I’d treat teammates or strangers?

I believe this isn’t just applicable to sports or physical activities, I think this same sort of internal dialogue happens in many pressure situations: giving a speech, pitching an investor, or running a difficult board meeting. Getting down on oneself and thinking: “Well that was a stupid thing to say.” isn’t going to help the situation.

Letting go of the judging process is a basic key to the Inner Game;

Instead, calmly acknowledge to yourself that whatever action didn’t have the desired outcome and then let go of the recrimination. This action will allow your natural coarse correction to take over which should get you back on track. Being calm and composed, either in sports or in the boardroom, gives you mind the ability to perform at it peak which will repair situations that have begun to go off the rails.

Aug 14

DEFCON Memories: That Time I Ran Away to Go to a Hacker Con

Mom: Wasn’t DEFCON the hacker event you went to when you were 15?

Me: Yes.

Mom: How did we allow that?

Me: You didn’t know because I didn’t tell you.

I went home to VT this past weekend to visit my parents and pick up this insanely cute kitten.

The kitten has nothing to do with this story, I just wanted to show her off.

Over dinner my father mentioned that he had heard an NPR story about DEFCON earlier that day. I was a part of the crew that put on DEFCON for 10 years, and I’ve been just an attendee more than a few times.

Comer TCPIPI had been at Purdue studying CS the summer before my senior year of High School. Ostensibly, it was to see how I liked the program, but I had hacker friends there and I mostly wanted to hang with them and read about the intricacies of the TCP/IP protocol.

I read this cover to cover that summer.

So that explained how they didn’t know that I went to Vegas. But then the question: how had I paid for the plane ticket. It took me a few minutes to remember; I sold t-shirts.

To finance my trip I created a t-shirt with two quotes.

Front: In this age of digital darwinism some of us are ones, you’re a zero.

On the back across the shoulders like a players name on a jersey, it said: 31337 

Which is Leetspeak for elite.

It also had a quote from the “famous” hacker Erik BloodAxe: I only hack for money

I borrowed enough money  from a friend to print a run, and then sold them at DEFCON. The proceeds were enough to cover my trip, and it was how I met the organizer, Jeff Moss, and became a Goon for the next 10 years.

I hadn’t thought about this in so long I had almost completely forgotten.

Aug 14

Confession: How Investments Are Like Pinball Machines

So I have a confession to make:  I own a pinball machine.  And not some little toy either, a full sized, modern, 300 pound piece of awesome. spiderman playfield And what makes this really ridiculous is that I live in a studio apartment. So what does this have to do with investing? If you live in a NYC apartment and you buy a pinball machine, then you buy your absolute favorite.  You only have room for one, so you don’t settle. I love that Spiderman machine; it is, by far, my favorite game.  Since I only have room for one I didn’t worry as much about price, I went for the best. Early stage investing is similar, there are only so many deals an investor can do since their time is a limiting factor. And since the big winners are worth many times the initial investment, price is not as important. If a partner can only do one or two deals a year they have to choose the best, their absolute favorites.