Do What You Love

Do what you love. Because you do what you love, you do it a lot. Because you do it a lot, you get good at it. Because you’re good, you can sell your skills and live well doing what you love. If you do anything else, you have sold your life for nothing in return.

(I realize the world isn’t this simple, but it’s the world I have dedicated myself to realizing.)


Notes from INNOVATE Boston

Ask questions only once you have completely exhausted your own resources. (Really?)

“VSnap” : for storytellers. Send short videos in lieu of emails. “90% of communication is nonverbal. So we want to enable full-body communication.”

  • “You’re about 40% more likely to do what I’m asking if I ask visually rather than solely through text.”
  • Make sure people know what’s at stake. So, what’s at stake for VSnap? The capacity to engage consumers, clients, and customers in more personal ways will have a huge impact on empowering them to make choices.
  • Balance confidence and humility: you need enough confidence to keep the vision, and enough humility to listen to your team and your customers.


  • Do fun stuff.
  • Do big stuff. Transformative stuff is hella fun.
  • Scratch your own itch.


  • Powerpoint sucks. Tell stories.
  • Budweiser, Coke, Frito-Lay: there to help retailers do well. (huh!)
  • Engage, involve, empower your customers / clients / consumers. They will reward you for it.
  • Try to walk away. If you can’t walk away from your idea, then it’s good.
  • Fail as fast as possible. Learn through failure. Recognize failure ASAP, and move on.


  • Focus! As a generalist, you have a wild perspective. Leverage it deeply.
  • Learn about something by writing about it.
  • Develop a framework for filtering the good advice from the bad advice.
  • Take your time with the hiring process. This is human relations, after all. Your margin for error is pretty low.


  • Mentors and coaches are critical. You can only teach yourself so much. (Hacker principle: never solve the same problem twice; if someone else did it first, learn from them.)
  • Valuable markets are those that let craftspeople stick to their craft; let the market handle marketing, vetting, etc.
  • Keep the vision. Stay true to the vision.
  • Don’t worry about secrecy. You need a team. You need friends. Solicit help. Talk to people. Meet your clients. Learn.
  • It’s important to spend a lot of time with the folks you’re going to bring onto your core team. Take time to meet them and learn them and build a great chemistry. Get to know them.


  • We call it “The Startup World”. Why? Because it’s so insular? Because it’s so different?
  • Most of the successful entrepreneurs I meet have really solid mentors and advisors.

Importance of Mentorship (I asked about this)

  • Every call could be the call that leads to something big.
  • Kiss a lot of frogs. Go down every path. You never know when you’ll find treasure.
  • Tap into the community. Help, and be helped.
  • Trust your team. Trust your mentors. Good relationships are built on trust.

Development lessons from my first three months at Matchbox

Development Workflow
1.) Understand the problem you’re solving. A user has requested a feature, but what problem are they trying to solve?

2.) Write a guide doc exploring the issue, and what the end solution achieves. This serves as high-level documentation for users and coworkers. (It also helps me remember what the heck I’m doing at any given moment)

3.) Write unit and integration tests that test whether the feature’s implementation (which you haven’t written yet) meets the specifications in the guide doc.

4.) Implement! Make sure your code is well-documented, so future-you doesn’t have to waste time becoming familiar with the problem all over again.

5.) Test and refine. Your tests should cover as much of the code as possible; my target is 90% coverage right now, since it’s often hard to test specific logical branches except through smoke tests.

Design Notes
1.) Color is weight. Real things are heavy. When we envision the future, it’s often in greyscale tones (such as Apple’s white and metal sheen) because those colors are ethereal and dreamlike. It reinforces the design’s futurism.

2.) Contrast is noise. Highly contrasting objects are loud, and will draw your audience’s attention. Turning up the volume too much will hurt their ears (or, in this case, their eyes), and turn them away.

3.) Audiences have a wealth of norms and codes with which they are familiar. Using these codes is like importing a library: it saves you the time of coding your own solution. Familiarity helps users navigate.

Cultural Notes
1.) Programming is hugely entrepreneurial, and in many ways the inverse of traditional entrepreneurship: First, we invent things. Then, we figure out how to monetize them (or we open source them and don’t worry).

2.) I’ve often heard, “Engineering is a practice of trade-offs.” Economics has a similar saying: “No free lunch: everything costs something.” I wonder if all disciplines could be reduced to “a practice of trade-offs”, differing only in the medium and context of the exchanged qualities.

3.) Entrepreneurship is mis-advertised as depending on bold ideas, but I contend it depends instead around diligence, determination, and passion. If you’ve got those, you could become an entrepreneur in fruit stands and still make it big.

Reflections on Post-Academia
1.) I consume books now. On design, on software patterns, on mathematics… These are books I would have read for classes, often. I want to read them now, because I know how they serve me.

2.) I wish there were more book clubs, or ways to find book clubs.

3.) I am not sure what I learned in school other than tidbits of knowledge. What economics I know, I learned from friends, family, and my own research. What technology I understand, I learned much the same way. Languages are the only thing I learned from academia that I would never have studied on my own.

Gerontocracy: Are the old hacking democracy?

After reading this article this morning, I began to wonder about the effects of population growth and decline on democracy. Baby boomers represent a huge lump in the nation’s population. Because of their age and their having been brought up around the same time, they’ll have similar perspectives on issues — and thus, similar interests. A politician who addresses the concerns of the baby boomers garners the support of an unusually large demographic. Because of their limited time horizon — as in, their interest in the world after they die is sentimental at best — pandering to them often comes at the expense of younger demographics. I’m sure this has been asked before, but do population fluctuations represent a structural exploit in even the most robust democracy?

Democracy theoretically spreads the power of government over all those it affects, in the hopes that spreading out power will make it hard for any one voice to dictate the nation’s course. Even if you were able to forge a majority out of some specific interest group, that majority’s constituents would still share plenty with the rest of the populace: a common interest in the nation’s continued improvement, for example. Accountants might fight for disclosure reform, but they would do so knowing that there will always be accountants, so they want their laws to be somewhat sustainable. When dealing with age-based coalitions, that concern evaporates: the old have no incentive to care for a future they will not live to see.

Population bubbles, thus, exploit democracy’s core weakness — the many may strong-arm the few — but poison it further: once the many get old and die, the few will inherit the mess that the many had no reason to deal with. Consider Japan’s aging population and its crusty government, or Europe’s similar predicament, or our own. Do the old represent democracy’s fatal flaw?

Most Startups Fail

I said to a friend, "Instead of going to college, why not join a startup, or better, why not start a business?" He replied, "Most startups fail."

So what?

Let’s pretend going to college is like starting a business. Every year, you pay tuition. Awesome; you’re already in the hole. Startups are usually the same: they require capital to get going. Whether that capital comes out of your pockets or the pockets of investors is up to you, but for the sake of comparison to college, let’s say it’s coming out of your pocket. So, exempting the possibility that the startup is paying you for your blood and sweat, both cost you money.

College purports to take your tuition and your time and convert it into knowledge, skills, and a social network. Startups purport to take your time (and any capital you invest) and convert it into… knowledge, skills, and a network. If you’re diligent, hard-working, insightful, and fortunate, you’ll get a fat bag of dollars out of the deal. If the startup fails, you’re no worse off than if you had graduated: you’re no longer pumping money into tuition / the company, you’re no longer bound by its schedule, and you’ve got experience to find your next gig with. For lots of folks, I would highly recommend foregoing college to start / join / volunteer for a young organization.

If you’re in college, or on your way to college, take time to prove to yourself why, for you, college is the best path for advancing your education. If nothing else, you’ll get more out of college for having been skeptical.

Email as To-Do

Taking a leaf out of Pivotal’s design notebook, and inspiration from Paul Graham’s hatred of e-mail, I’m drawing up designs for an email client that basically treats your emails as elements of several related to-do lists. The basic workflow is this:

  • You get an email. It goes into a list of emails that haven’t been dealt with in any other way.
  • Several other lists are also on the page, such as "Important", "Work", "Family", etc. Each list is defined by a filter, or set of filters.

    You can drag and drop emails between lists. Doing so applies the list’s filters to that email.
    You can assert that all emails similar to one or more selected emails should be filtered in a certain way.

  • Several lists are visible side-by-side on the page.
    You can edit which lists are visible, or add new lists.

Why is this awesome? Because email is just a giant to-do list, that anyone can add things to. We phrase requests and replies as traditional letters, but really, it boils down to "read me!", "respond to me!" and potentially "follow the directions I contain!". Providing better ways to consume its data, and decide how to tackle this to-do list, is something I’ve wanted personally for a while.

Of course, I won’t pitch it as "email as to-do" list, because the only way what I’ve suggested really differs from every major email client is that you can view multiple inboxes side by side, and drag items between them. I’m changing the interface, so you can organize your emails more easily. But email basically remains email.

Reflections on “The Big Short”

Sometimes I muse, “If I were a money manager, how would I invest?” Knowing that governments can be bought, and that governments are essentially power-vendors selling their wares wholesale, I imagine that I would invest in firms with strong ties to government. Buy when they seek government attention (and have the means to get it), sell before they mess up. Based on the available data, I’m relatively confident in this as a long-term strategy. Of course, I could never do this for a living. I can’t think of a more morally crushing career than profiting from the good fortune of firms I despise.

Books like “The Big Short” both strengthen my convictions and cast doubt on them. Given a grossly imperfect market, such as those for bonds, calamity is basically inevitable, as feedback loops try to work out inefficiencies. I loved reading that the big firms had retreated into bonds because the stock market had grown too competitive for them. They couldn’t take the heat. They should have bitten the dust.

But they were the ones who ultimately decided the course of the bailout, precisely because of their size. They bought power at wholesale prices from the state. They made out like bandits, just like I would expect them to.

And yet, for the most part, their stocks have remained low. The market might still be rife with structural inefficiencies, but slowly, slowly, it is learning. It knows these firms shouldn’t be trusted.

In essence, “The Big Short” has only affirmed what I already believed: that only by making markets more efficient can we really affect change. Government’s incentives to perform are awful and perverse, as are those of large firms in inefficient markets. No supervisor, bureaucrat, or regulator will save us from the idiocy of the powerful. Only our own ingenuity can do that.