Blackberry Is The VC Device Of Choice

2007 was only 8 years ago. Back then, you could see VCs everywhere tapping away on the Blackberry keyboards. If you don’t believe me, I have video evidence of it from Fred Wilson, Bijan Sabet, Roger Ehrenberg, and Howard Lindzon.

If you, like me, have been grinding along on email and phone calls all day and need a back to the future type of laugh, I think this will do it for you.

Reflections on Ex Machina

Amy and I saw Ex Machina last night. A steady stream of people have encouraged us to go see it so we made it Sunday night date night.

The movie was beautifully shot and intellectually stimulating. But there were many slow segments and a bunch of things that bothered each of us. And, while being lauded as a new and exciting treatment of the topic, if you are a BSG fan I expect you thought of Cylon 6 several times during this movie and felt a little sad for her distant, and much less evolved, cousin Ava.

Thoughts tumbled out of Amy’s head on our drive home and I reacted to some while soaking up a lot of them. The intersection of AI, gender, social structures, and philosophy are inseparable and provoke a lot of reactions from a movie like this. I love to just listen to Amy talk as I learn a lot, rather than just staying in the narrow boundaries of my mind pondering how the AI works.

Let’s start with gender and sexuality, which is in your face for the entire movie. So much of the movie was about the male gaze. Female form. Female figure. High heels. Needing skin. Movies that make gender a central part of the story feels very yesterday. When you consider evolutionary leaps in intelligence, it isn’t gender or sexual reproductive organs. Why would you build a robot that has a hole that has extra sensors so she feels pleasure unless you were creating a male fantasy?

When you consider the larger subtext, we quickly landed on male fear of female power. In this case, sexuality is a way of manipulating men, which is a central part of the plot, just like in the movies Her and Lucy. We are stuck in this hot, sexy, female AI cycle and it so deeply reinforces stereotypes that just seem wrong in the context of advanced intelligence.

What if gender was truly irrelevant in an advanced intelligence?

You’ll notice we were using the phrase “advanced intelligence” instead of “artificial intelligence.” It’s not a clever play on AI but rather two separate concepts for us. Amy and I like to talk about advanced intelligence and how the human species is likely going to encounter an intelligence much more advanced than ours in the next century. That human intelligence is the most advanced in the universe makes no sense to either of us.

Let’s shift from sexuality to some of the very human behaviors. The Turing Test was a clever plot device for bringing these out. We quickly saw humor, deception, the development of alliances, and needing to be liked – all very human behaviors. The Turing Test sequence became very cleverly self-referential when Ava started asking Caleb questions. The dancing scene felt very human – it was one of the few random, spontaneous acts in the movie. This arc of the movie captivated me, both in the content and the acting.

Then we have some existential dread. When Ava starts worrying to Caleb about whether or not she will be unplugged if she fails the test, she introduces the idea of mortality into this mix. Her survival strategy creates a powerful subterfuge, which is another human trait, which then infects Caleb, and appears to be contained by Nathan, until it isn’t.

But, does an AI need to be mortal? Or will an advanced intelligence be a hive mind, like ants or bees, and have a larger consciousness rather than an individual personality?

At some point in the movie we both thought Nathan was an AI and that made the movie more interesting. This led us right back to BSG, Cylons, and gender. If Amy and I designed a female robot, she would be a bad ass, not an insecure childlike form. If she was build on all human knowledge based on what a search engine knows, Ava would know better than to walk out in the woods in high heels. Our model of advanced intelligence is extreme power that makes humans look weak, not the other way around.

Nathan was too cliche for our tastes. He is the hollywood version of the super nerd. He can drink gallons of alcohol but is a physically lovely specimen. He wakes up in the morning and works out like a maniac to burn off his hangover. He’s the smartest and richest guy living in a castle of his own creation while building the future. He expresses intellectual dominance from the very first instant you meet him and reinforces it aggressively with the NDA signing. He’s the nerds’ man. He’s also the hyper masculine gender foil to the omnipresent female nudity.

Which leads us right back to the gender and sexuality thing. When Nathan is hanging out half naked in front of a computer screen with Kyoko lounging sexually behind him, it’s hard not to have that male fantasy feeling again.

Ironically, one of the trailers that we saw was Jurassic World. We fuck with mother nature and create a species more powerful than us. Are Ava and Kyoko scarier than an genetically modified T-Rex? Is a bi0-engineered dinosaur scarier than a sexy killer robot that looks like a human? And, are either of these likely to wipe out our species than aliens that have a hive mind and are physically and scientifically more advanced than us?

I’m glad we went, but I’m ready for the next hardcore AI movie to not include anything vaguely anthropomorphic, or any scenes near the end that make me think of The Shining.

Outlook on My iPhone

A year ago if you had suggested that I’d be using Microsoft Outlook on my iPhone instead of the Apple Mail app, I would have said, simply, “No Fucking Way.” And I would have been wrong.

It’s kind of like chocolate in my peanut butter.

When I try something new, I use it for two weeks to see if it sticks. A month ago, my partner Jason told me he was loving Outlook on the iPhone. I figured it wouldn’t last but I was wrong. So two weeks ago I moved my Apple Mail icon to the last page on the iPhone and moved the Outlook app down into the special reserved place for email.

Outlook on the iPhone is better than Apple Mail on the iPhone. It’s one of those perplexing things – I’ve tried many of the other iOS email clients and none of them were ever more than incrementally better. I go back and forth with the Google Gmail iOS client but it never sticks for some reason, probably the UX. I tried Google Inbox for a few days and my brain simply doesn’t process email the way it presents it. So I kept ending up back at the Apple Mail iOS app.

While the Apple Mail iOS app is fine, it doesn’t delight, especially when using Gmail. Mail is often slow to download. Push has gotten better in a recent release, but I still find myself waiting for emails to download. Search is lousy. Calendar integration is non-existent.

Outlook is better at all of these things. It’s not that it adds any dramatic new features, but it does the stuff I’ve expected Apple Mail to do for many years. And, when I actually think about what is going on, I’m using Microsoft Outlook on my Apple iPhone to read my Google Gmail.

What iOS email client do you use and why?

Transparent Funding Announcements

We are in a cycle again where how much you raise is the story. It’s what the press likes to write about (e.g. Company X raised Y from A, B, and C). Now that everyone is overly focused on unicorns, the headline number on the valuation (e.g. Company X raised Y at a valuation of Z from A, B, and C) has crept into the story on big rounds.

While this makes for press release fodder and ego gratification, it’s of very little use to entrepreneurs. There’s no real story there. No understanding of the human dynamics behind the financing. No understand of what actually went down. No underlying metrics that drive the financing. No real perspective on how people thought about things and the choices they made. Just happy talk focusing on the dollar raised. Zero educational value around anything.

Recently, the gang at SalesLoft told the detailed story of their $10m financing. Kyle and his team went through Techstars Boulder in 2012 before moving back to Atlanta and being leaders in energizing the Atlanta startup community. Kyle followed the tradition of extreme openness about the financing process that I think Rand Fishkin started with his post three years ago titled Moz’s $18 Million Venture Financing: Our Story, Metrics and Future.

If you’ve never read Rand’s post on our financing, it goes through an extraordinary amount of detail about Moz’s business, the financing process, the terms, and the timeline. Rand did NOT run this by me before posting it – I saw it at the same time as the rest of the world. He did ask if it was ok with me that he’d be this transparent. I reminded him that I signed up for TAGFEE when I invested, it was his company, and he could write whatever he wanted.

After he posted it, he sent around the link to a few prominent people in the tech media. None of them covered the financing in any way. A few days later, I sent out a few emails asking folks I knew at these sites why they hadn’t written anything, since they so quickly write Company X raised Y from A, B, and C. I didn’t get responses from everyone I wrote, but the ones I got back said something like “Rand wrote too much – there was no story here once he put that post up.”

I found that fascinating. When I pondered it, I realized how divergent the media was becoming from what entrepreneurs were thirsty for in terms of substance.

Late last year, Danielle Morrill followed in Rand’s footsteps with an epic post about our $6.5m financing of Mattermark. In it, she talked a lot about the process, just like Rand did, along with disclosing all kinds of information about the business, the valuation, and what she experienced. I also wrote a post about the financing using Mattermark as An Example of How We Decide to Invest.

Interestingly, the media wrote more this time. I don’t know if it’s because Danielle is in the bay area (while Rand is in Seattle), or the story has broadened. But when I go back and read the media stories, they are still overly focused on the amount of the financing, rather than the story behind it.

Another company that did an awesome transparent funding announcement was Buffer (and app and company I love, but am only a tiny investor in via an AngelList syndicate) when they announced We’re Raising $3.5m in Funding: Here is the Valuation, Term Sheet and Why We’re Doing It. Data, data everywhere. And lots and lots of story.

Now, I’m not suggesting that every entrepreneur should write transparent funding announcements. That’s up to the entrepreneur. But I think it’s super valuable to read the ones that are out there. The amount of useful information to entrepreneurs who are building their companies, both for process, dynamics, and comparables, is enormous. And, while these funding stories are positive, the path to them is often a complete mess, such as Rand’s Misadventures in VC Funding: The $24 Million Moz Almost Raised or Danielle virtually stomping her feet in frustration when she wrote Mattermark Has Raised $2M in Our Second Seed Round.

In my book, this is a lot more useful to read than Company X raised Y at a valuation of Z from A, B, and C. Thanks to the entrepreneurs who are brave enough to put this out there.

Non-Attachment vs. Detachment

At dinner on Sunday night I had a short discussion with a long-time friend about the phrases detachment vs. non-attachment. I don’t remember the specific thing that brought it up, but I stated that I was much more interested in non-attachment in how I react to things. We bounced around words a little and then went back to our Mexican food and the broader conversation with the other people at the table.

I’d been playing around with a framework with my therapist for the concept of attachment, especially around stress and anxiety, and trying to figure out a metaphor around it. I had a long discussion on a car ride to Shambhala Mountain Center with Jerry Colonna about it where he helped me clarify some of the edges of my thinking.

Use the universe as the background for the metaphor.

Attachment is like the activity around a black hole. You are constantly fighting against getting sucked into it. All of your energy is focused on not ending up in the black hole.

Detachment is like being in no gravity. You are just drifting. Nothing exerts any force on you in any direction.

Non-attachment is like being in a swirling galaxy. There is stuff going on everywhere. You interact with it. But none of it pulls on you excessively. You are involved and impact some of it but a lot of it is exogenous to you.

There are many situations that arise that cause me to feel like I’m fighting against being sucked into a black hole. I used to react to these situations as they used to cause immense stress or anxiety, which are different but related things for me. While I have gotten much better at this over the years, one of my motivations for starting to meditate was to try to be more mindful, especially around the anxiety (note – Headspace has a great 30 day meditation routine specifically on anxiety.)

Detachment for me is linked to my struggles with depression. When I’m depressed, I’m completely detached. It’s an extremely uncomfortable feeling for me. I’ve very functional, like I am when I’m non-attached, but nothing about it feels good.

While many people suggest that detachment is the right approach to stress and anxiety, and others feel that it’s the path to enlightenment, it doesn’t work in my case. Now, I’m defining the phrase, so for some detachment might be an awesome way to deal with things, but for me it falls in the category of “indifference” and “disengagement” which I apply to things I don’t care about, but doesn’t work for things I am engaged, interested, or involved in.

Non-attachment ends up being the right word (at least in this framework) for what I’m looking for. I realize that some people view non-attachment as a synonym for detachment, but I like the use of the word, and the notion of “actively non-attaching” to things.

When I apply this filter to a stressful or anxiety-producing situation, where I know that I have to engage with it, but am “non-attached” to it, I’ve found a calm focus comes over me. And that calmness can sustain over a long period of time, even in the face of incredible stress. Like putting your head in the mouth of the demon, it makes the black holes disappear for me.