Jul 14

Gmail’s March to World Domination: The Platform Strategy

Gmail plus Chrome Gmail is an app eco-system that has snuck up on me. I now can’t use Gmail without:

  • Assistant.io – An amazing little meeting scheduling app.
  • Boomerang – An app that lets me schedule emails to be sent later or returned to my inbox as a reminder.
  • Rapportive – Lets me see info on the people I’m emailling.
  • Relate IQ – Lets me update our CRM from within the email.

And thats not even getting to the useful Chrome extensions:

  • Honey Badger – A great tool to learn about the traffic and funding of a website.
  • Evernote – I use the web clipping to make articles easier to read even if I don’t plan to save them.
  • Ghostery – Tells me what cookies are being used to track me on a given page.
  • LastPass – Secure passwords, nuff said.
  • BufferApp – Allows me to schedule my social media posts.

Gmail is slowly building a platform that will be very difficult to migrate away from. I’m sure others said the same about Outlook in the past, but cloud platforms seem more powerful than their desktop ancestors since they so easily build upon the services provided by others.

Jul 14

Too Cheap To Count

hash marks

Fred Wilson has a great post about what technology was rare enough for one generation to count but ubiquitous for the next
• Electric Motors 
• Chips 
• Networked Devices 

He also talks about how the networked devices of the future will be dumb. 

So my bet is that most “things” will be dumb and the smarts will be in the phone or in the cloud.

But I respectfully disagree. In my post about computing paradigms swinging like a pendulum I stated that Moore’s Law means that dumb devices become smart over time.

via Intel presentation

via Intel presentation


While I expect Fred to be correct in the short term, dumb devices connected to smart hubs, over the long run I expect each of those devices to be imbued with more intelligence than Siri has today

I believe that while you and I know the number of “smart” devices we own, the next generation won’t be able to keep count. 

Jul 14

Forming New Habits: My Week of Awesome

Habits sign

Lately I’ve felt like I was in a bit of a rut so I decided to try an experiment to be more productive.

I started by making a list of things I wanted to do.

  1. Read more blogs
  2. Publish a blog twice a week
  3. Practice a skill for 10 min
  4. Drink less at social functions
  5. Exercise more

To do all this I decided to wake up an hour earlier each day and use the Streaks app to track my goals.

On the first day I woke up early, went to my local coffee shop and found this great video/article on forming habits my Pocket App. It must be a sign. One of the most interesting things Maneesh discusses is keystone habits; a change you make that cause other habits to naturally happen in your life. One of those is waking up early.

The thing about waking up early is that it is a keystone habit. A keystone habit is a single habit, a solitary act that once implemented it starts a chain reaction that begins other habits naturally.

I have to admit, I’m not a morning person but getting so much done before my day really starts makes me feel like a superhero. The reading is generating tons of new ideas and tracking is pushing me not to procrastinate.

So I challenge you to start your own Week of Awesome. Let me know what tools you use and how it turns out.


Jul 14

History is All Lies: The Pendulum of Computing Paradigms

As with many of these posts, I learned that history is often apocryphal when I go to link quotes. I started by trying to find the origin of this famous quote:

I think there is a world market for maybe five computers” – Thomas J. Watson

This is probably a misquote, but it is a great start to the pendulum that is the centralized  vs. decentralized computing model. Let’s walk through the 3 major computing paradigms: Big Iron, Enterprise Computing, and The Web, after which we will look at where we stand today with Mobile Computing.

Big Iron: In the beginning we had centralized computing. Giant machines with an army of attendants that fed in punch cards. Then we attached dumb terminals, teletypes, to it and called it Time Sharing. This was centralized.

Enterprise: Slowly the dumb terminals started getting things like storage. Moore’s law took effect. We got computers on the desktop and the model was Client Server. While there were some shared resources, computers generally had all their software and data locally. This was decentralized.

The Web: When the web was born we had light weight browsers that connected to powerful servers once more. Once again all the resources resided in the center, and the browsers were essentially dumb. With the innovation of AJAX the browser started doing more work for the user, but it was still essentially a dumb client. Centralized.

Mobile Computing: At first phones were dumb; but soon  Moore’s Law kicked in and the devices became powerful enough to do real work. We even renamed them Smart Phones. This gave rise to application paradigm. Once again, the phone ran software and much of the data needed was stored locally in case the network wasn’t accessible. Decentralized.

As long as Moore’s Law holds, which I believe it will, this pendulum will keep swinging back and forth as the dumb devices begin to have enough computing power that it becomes worth the effort to harness them. I believe this has some interesting implications about the different ecosystems that Apple and Google have created, the former being more device oriented and the later focusing more heavily on the cloud.

Jul 14

Security Paradigm Shift: The Attackers Have Won

cyber-attack The attackers have won.

This fact is at the center of a major paradigm shift in computer security. Hackers and security professionals have known forever that a sufficiently motivated attacker will always breach a system, but business leaders and the public thought that walls could keep attackers out.

No one is deluded anymore, Even Symantec has admitted that Anti Virus software doesn’t work. Though that is because they don’t think it will sell anymore and they are pushing a new solution. 😉

A real reason for this shift is that executives are now being held responsible for security; people getting fired and sued are big motivating factors. The CEO of Target was fired after their very public security breach.

We used to naively believe that security was actually possible, and that with firewalls and code reviews we could keep most attackers out.

Back at @Stake, we used to use the onion and the egg metaphor to explain defense in depth. broken-egg onion-layers-300x279An egg has a hard protective shell, but once it is broken, the inside is soft and gooey, like the network behind a firewall.

An onion has several protective layers. Try dropping both from six feet and the point is obvious.

So we promoted security audits, code reviews, and defense in depth. But all of these solutions assumed that a secure system could be built, that given enough layers a site would be secure.

We are now learning that it is a process for both security and response; moving faster than your attackers, not just building roadblocks in front of them.

So what’s next?

The future involves detection and response. If an attack can’t be prevented, we need to minimize the cost of losses and remediation. We should be able to quarantine and clean bad machines in seconds. “Big data” should tell us which machines have been compromised. Cloud File storage should allow us to actually protect important files since they only reside in one place, as opposed to having a copy on every laptop.

I’m thinking about three legs to the stool:

  1. Detection: their are multiple ways a system breach can be detected after the fact, this will bring down the time an attacker controls a machine.
  2. Remediation: the tools of forensics aren’t tuned to the quick quarantine and cleanup of a machine.
  3. Data Loss Protection: DLP has always sucked, but perhaps now that files are all stored in a single central spot we can make this really work. Perhaps we can prevent our IP from being sent out even if a machine is breached.

The attackers have won; now we may finally get secure systems.

Jul 14

MAWG – Middle Aged White Guy

From Pattern Recognition by William GibsonPattern Recognition

He reaches into a shirt pocket and pulls out a card. Stepping forward, he offers it to her. She takes it and squints, through the dust in her eyes and the hard white light, at



“SINCE 1967”

She looks up at him.

“Music business,” he says. “In Chicago, if you’re a certain type of musician, you need one.”

“One what?”

“M-A-W-G. Mawg.”

Middle Aged White Guy.

In a lot of way the job of a venture investor is similar to that of an A&R (Artist & Repertoire) scout in the music business.

You’re a talent scout looking for promising groups. When you find one, you give them money and advice to try to help them grow.

Early on A&R guys wade through the tapes submitted to labels by bands and spend a lot of time at clubs trying to discover something for themselves. VCs go though decks sent in and troll demo days and networking events.

Essentially I’m a talent scout that helps manage the band after they get a record deal; Middle Aged White Guy since 2011.

And yes, this analogy makes founders the Rock Stars.

Funny thing is I know some EX A&R guys. They love music, so its odd that they are hated as ‘The Man”.

Macklemore even wrote an entire song lambasting record exec Jimmy Iovine.

And VCS get the same wrap today.

And it is likely that this metaphor extends further. Music  discovery and financing was disrupted; Macklemore is the perfect example. That process is also happening in the venture world.

I’m looking forward to the upcoming changes, no one really wants to be known as a Middle Aged White Guy.