Snapchat: Platform of the Now

Last year I went from skeptic to admirer, and ultimately fervent user of Snapchat. 

Yesterday’s app update brings disappearing text conversations, and real-time video chat to the platform - and while I’ve struggled a bit to get it to work (no doubt some initial scaling challenges) when it does it’s quite fun.

Snapchat is deepening a very meaningful position for itself in the world of messaging. Namely they nail “the now.”

At first, self-destructing images seem like a gimmick, but as I argue in my link above, it creates real psychological “oomph” to every message, no matter how inane, that focuses user attention squarely on something that feels like it’s happening right now; do not blink, you will miss this.

That differentiator (or ‘gimmick’ if you can possibly still be skeptical) has allowed Snapchat to achieve the kind of scale and network that grants real staying power.

And in a world of me-too messaging apps, Snapchat is doubling down on that feeling of “the now” by moving that oomph from images into temporary chat convos, subtle (and not so subtle notifications) about who is interacting with you in this moment, and real-time video. Instead of using their scale to justify “generifying” their offering to fall in line with other messaging apps & feature expectations (a plausible path), they are continuing to carve out novel features for their messaging platform of “the now.” There is no history, like real-life, what happens in Snapchat happens but once, and we all move on.

Heartbleed and the Fragile Physics of Software

One of the underlying principles of the Internet’s design is that of robustness and decentralization - large parts of our physical infrastructure might fail, and yet the packets will still flow. The great irony is that the fragility of the Internet comes from somewhere else entirely: the winner-take-all dynamics of software itself.

Heartbleed highlights this to the extreme. While a handful of different open-source TLS libraries exist, one in particular, OpenSSL, protects the majority of the Internet. This is because it is the default SSL library for the two most popular web-servers, Apache and Nginx, which run 70+% of the busiest sites on the web.

So why such concentration? The world of software isn’t constrained by locality - multiple libraries that don’t serve particular ideological or technical niches are truly wasteful and duplicative effort. And this brings us to the brutal reality of software-physics : open-source efforts tend towards collaboration & concentration (ideological & technical concerns being equal) resulting in concentration of important libraries, and thus concentration of usage in the wild.

The unfortunate side-effect is a fragile internet. Vulnerabilities can, do, and will exist in any given library. If we had a multitude of libraries, we’d have a multitude of vulnerabilities, but no single attack would be so devastating. However, software-physics push us towards fewer, higher-quality libraries with devastating consequences when they are compromised.

Heartbleed is indeed one such terrifying vulnerability, and it won’t be the last as long as the physics of software development & deployment remain the same.

Joining Venrock to do VC in Boston

I’ve had a few months downtime since I left Boundless, and go figure, I decided to spend most of my time meeting and helping other entrepreneurs. You’d think I was hooked.

Well, I am, and so I’m excited to share that I’ve joined Venrock as a Vice President in the Cambridge office, working locally with Mike Tyrrell, to help make more investments in the Boston ecosystem.

I first met team Venrock when they invested in our Series A at Boundless; Mike joined our board, and it’s been great getting to know him over the past year or so -  I jokingly called him the “rock”: Mike is a stable, no non-sense, straight-shooter with deep experience, so when he offered me the opportunity to join team Venrock I considered it seriously. After thinking about the role, and meeting the rest of the investment team, I was blown away by the degree of aggregated-smarts - and totally convinced.

Ultimately, I love people, ideas, technology and learning - so I can’t think of a better way to combine my passions than a job that enables me to meet smart entrepreneurs, learn about the their big ideas & novel technology, with the added bonus that perhaps Venrock can help them realize their vision for change.

Win/win/win… s

Dear Boston Entrepreneurs,

     I’m really looking forward to working with you! If nothing else, I pride myself on being approachable and helpful. Let’s think big, and do great things together! 

- Aaron

How I Beat the World High Score in Dots (hint: I cheated)

Nothing unlocks your inner hacker like some friendly competition between friends. So when friend Brian Balfour threw down a Dots gauntlet with a high score of 479 I knew I had to end him. And not just him, but I wanted to shame ALL Dots competitors.

The first obvious strategy for dots is to only focus your efforts on forming squares, which eliminate all dots of the same color from the board, and tend to form new squares. That combined with smart use of the shrinker power-up puts you in a good place to strike around 350 to 400 consistently. (Yes, you’ll most definitely have to purchase dots to be competitive)

The next step is to ruthlessly restart games until the starting board presents a good square or two, and then coldly abandon games where lady-luck doesn’t keep the chains flowing. When lady-luck runs out in an otherwise excellent game, that’s when you deploy your ‘expander’ power-up. Finally, executing your games carefully is also immensely easier on an iPad. Now you can approach 500, but with considerable time investment.

So how was I able to score 928?


Simple, I cheated.

As it turns out, pausing and un-pausing (by pressing the timer in the upper left) the game doesn’t effect the clock properly. In fact, you’re given ‘free time’ to examine the state of the board while it slides in and out. With epilepsy-inducing rapid fire of pause/un-pause, you remove all time spent thinking from counting against the clock, and only your deliberate hand motions to execute your choices count against you.

However, before you get your hopes of public glory too high, the smart folks at Betaworks (owner of Dots) recently (& thankfully!) became aware of this cheat and are now filtering out scores server-side that were achieved this way - expect more changes to the leader-board. (And what a shame, my mother would have been so proud)

Still, you can tweet & text your outsized score directly to friends if you’re looking to upset them into pursuing some sisyphean pursuit.

Thanks, and until next ‘hack’.

- Aaron

Big Changes

It’s hard to imagine a time more intense or enjoyable than the last few years I’ve spent building Boundless with Ariel & team. We took a bold idea, partnered with bold investors, had the good fortune to assemble one of the smartest teams in Boston, and willed into existence an important and transformative education company - one that will continue to shape the landscape for a very long-time. And we’re on a tear, Boundless is now used by students at over half of US colleges. Our open textbooks were recently released under Creative Commons open licenses, and since then have helped over half a million people

There is a great irony in Boundless accomplishing so much so quickly. We have put in place an incredible team that is executing down our ambitious multi-year roadmap, and for the experimental & techie startup-er that is my core, this presents a challenge: what do you do when you’ve carefully & consistently hired amazing people who can really lead and scale each facet of the organization?

In this particular circumstance, and after careful consideration, I’ve decided to step down as CTO and my day-to-day work. I leave engineering running as it has already been for the last year: in the incredibly capable hands of our VP Engineering, Matt Hodgson. While I’ll certainly miss being a part of the daily energy in the office, I will continue to assist and advise the company strategically as both a member of the board, and as a passionate advocate for our team & our mission to dramatically improve the state of higher education in the US - there’s much to be done! 

As for what else may come next for me, I’m still burdened by an intense passion for making the world better through software, and since the world isn’t perfect just yet, I suspect there are plenty of areas left to explore :)

Hiring and Leading a Superpowered Team

This Intelligently class, run by Boundless’s own Nick Ducoff, should not be missed. Nick is an incredible manager/operator/entrepreneur, and has taught us tons - building out a killer team, getting everyone on the same page, and executing down complex projects without missing a heartbeat, paradoxically hitting outrageous goals with reliable predictability. A great deal of his success comes down to his team management process - set goals, get aligned, be humane, and run like hell.

He’s given me a sneak preview of the outline, and I’m excited for the talk - if you want to learn how to create & run killer teams, you’ll want to attend. See you there!

Boundless Engineering just cooked up an awesome internal change-log dashboard for the company. 
Naturally, seeing the gift icon causes quick adrenaline bursts :)

Boundless Engineering just cooked up an awesome internal change-log dashboard for the company. 

Naturally, seeing the gift icon causes quick adrenaline bursts :)

Gave a quick in office-presentation on how students should think about getting a job at a startup. Hope some of you find it useful! 

Links and slides are available on the Boundless Blog over here.

Whiteboard or Die

I have a theory: “He who controls the whiteboard controls the conversation.” There’s a certain level of implied command when you’re standing in front of the room putting your ideas into writing, or real-time editing the thoughts of others (no matter how subtlety)

If you’re an introvert, it may be extremely hard to combat this extrovert-controlled reality.

At Boundless, we do our best to make sure everyone is a capable “whiteboard warrior”, allowing the best ideas to surface. The best way to ensure such equality, is by hiring folks who are comfortable communicators - one of the reasons we screen all candidates by asking them to give a full-team presentation. Can they hold the companies attention and make a point?

If they can’t, how likely are they to do so in the next group meeting? Or the one after that?

What’s Your Superpower?

When I get to know someone, I make it a point to identify their superpower: what’s the one thing they truly excel at? And once you know someone’s singular, superlative-strength, great things can happen! Over the past few years, I’ve met and worked with some exceptional people. I’d like to share a few super-hero friends/colleagues & their powers with you:

Ariel Diaz: Vision

Ariel has strong, detailed, and vivid visions of how the world ought to be. This gives him exceptional perspective on what can-be, should-be, and what it will take to get there.

Brian Balfour: Insight

Brian has the uncanny ability to both actively and passively ingest large amounts of data, reflect privately for a while, and then drop some serious insight bombs that are truly mind-blowing.

Christopher O’Donnell: Product

Is there someone in Boston who is the spiritual successor to Steve Jobs? Tough to say, but if you asked me to cast my vote, I’d hand it too happily to Christopher. His no-BS, this-is-exactly-what-we-need-to attitude makes him a phenomenal product person

Patrick Campbell: Execution

The youngest in this list, Patrick’s ability to STFU and GSD is inspiring. This guy just cranks, unabashedly and without hesitation. 

Chris Keller: Networking

Ever wonder how to network to someone who is important to you? Chances are Chris Keller already knows them, hang/vacations with them, and is more than ready to make a friendly intro; he’s the best startup-connector I know.

Nick Ducoff: Management

TIme and time again, Nick has show the team at Boundless what exceptional management is truly about: recruiting, nurturing, planning & delivering. I can’t imagine building our company without him.

Matt Hodgson: Making Stuff

Matt can build anything, and build it well. He sees past the nuance, past the unimportant, and cuts straight to the core of how software should be made. This allows him to skip to the chase on construction, and lead a team to conquering the heart of a problem, producing beautiful results along the way.


What’s your superpower? What are those of your closest colleagues & friends? It’s worth answering explicitly for every exceptional person that you meet.