Classical, coffee, and coding on a Saturday

Took this picture in the new but temporary Cloudbot “offices”.  Man, the weather is better here, but I can’t wait to get back to Chicago.

Why failing fast is a blessing in disguise

Photo graciously CC-licensed by Flickr user behruz.

My last startup idea, I’ve determined it can be revealed, was a mobile payments startup.  We wanted to handle mobile payments by smartphone in a totally different, way faster way than anybody’s done before.  We knew our tech would work, and we hoped we’d be able to probably get a decent number of customers in the SMB space.

Then, the hammer dropped.  My co-founder’s parents called and told him he really should focus on his schooling instead of building another company (he was already on the board of a national not-for-profit).  Quite literally, the next week we found out that Techcrunch was reporting that Apple, with more credit card numbers on file than PayPal, was sniffing around a mobile payments startup called Boku.  Our entire model hinged on storing credit cards easily, and we were starting from 0 — a heck of a lot less than 500 million or however many iTunes accounts there are globally.  The news meant that while we could still enter the space, one of our least-likely “what ifs”: The “What if Google does it?” that we’d assumed they never do because it seemed small-time for them to us — came to pass.

That doesn’t mean we couldn’t have done it.  It doesn’t mean our company wouldn’t have been profitable.  But for us, it was a sign that as two small-time college kids with no funding, we were playing with the big boys in a place we didn’t want to be.

But the experience was great, and it taught me tons of lessons about who would listen to kids with ideas in Chicago, how to get things done in a co-founder relationship, and many other lessons.  In other words, entrepreneurs know about mitigating risk.  At this stage in my life, “wasted time” = gained experience, so it’s really not a waste.  Even if you’re a seasoned expert, seeing that wasted time and failing fast as a learning experience, not a true failure, can help you immensely.

Your mom has to understand your startup

Photo is CC-licensed by Flickr user kkanouse.

As all of us entrepreneurs are with family either in person or in our thoughts this Thanksgiving weekend, don’t forget to ask yourself questions about your company or startup ideas in the context of that wider world:

• Do people in the “normal people” column, like my family, understand what I’m building?
• If they struggle, or can’t understand it, why?  Am I not pitching it well, or is the idea crap?
• Even if they’re not the target market for your startup, can you describe it to them in a few sentences and have them at least begin to understand it?

Special comment on that last one.  Even if you’re building high-frequency trading software or being a liaison between two obscure industries or something else “B2B”, it’s my personal opinion that you still need to be able to use a few sentences to describe what you’re doing to be successful.

At the very least, practice your elevator pitch on your family this weekend – just to gauge whether they think your idea could be important or useful, if nothing else.

Learning vs. building

Photo credit: flickr user joewatrach.

In all kinds of industries, there are systemic disconnects between what students are trained on, and what the actual industry demands. As a CS student who has made somewhat of a break from the academic world, I want to shed some light on the problem of why there are so many great programs teaching ostensibly useful things that just fail to turn out good devs.

At least from my experience at DePaul, students learn:

• physical computer science (lots of cryptic stuff from the 1980s that is certainly important but my god, does this really have to be all we learn?!);
• how to optimize loops and how to use the right data structure or algorithm at the right time;
• basic UNIX OS and network programming; and
• lastly, how to feel inferior to the game design majors, who do very little theory and tend to just get their hands dirty making games (at least from my limited experience).

Maybe my perception is skewed as a guy who’s a bit disconnected, but the real problem as I see it is that DePaul, and I think many CS programs in general, emphasize learning the ancient tenets handed down by the masters rather than breaking things and building things. Now I’m not saying theory isn’t important. I’m saying the working world doesn’t have time for it; if you wanted to think about fluffy topics and write essays, you wouldn’t have gone for CS. By one’s third year, we should be committing patches to open-source projects, building Twilio apps, or trying to white-hat scrape our online courses system.

Quite recently, in one of my final exams, I had to hand-write complex unix system calls over and over again as part of a code-completion exercise. The function documentation was printed right on to the test- I found myself simply flipping back and forth, literally just performing an arcane imitation of copy-and-paste that would have taken me 20x less time if I was at a computer. Did this help me learn the material? Of course not, I was in the middle of a test and sweating bullets.

I think CS programs need to teach the following:

• How to think independently as a coder and find answers yourself;
• How to sell what you’re doing as an idea or process to your boss or your team members so that everyone knows you can be trusted to deliver;
• How to hack; that is, how to **build real stuff** quickly and efficiently. In other words, why aren’t we having hackathons?
• How to work as a team! CS schools and workplaces alike have developers of all different skill sets. “Learning to learn” from and trust your peers is key to working successfully.

I leave you with this final anecdote that illustrates the problem quite nicely: I was in a class where the professor mentioned that the Django web framework was developed in a building across the street from our school. Only 3 people in the room knew what it was, but more importantly: nobody cared. I felt like rockstars were nearby or something but that passion was quickly stifled when I saw that nobody thought that was cool. There was just a total non-plussed reaction.

Anyway, that killed my excitement and we quickly moved on. Why aren’t these people our rockstars? Why wasn’t that more exciting? Why don’t almost any of my classmates know what Y Combinator is? Maybe I’m kind of a groupie. Still, I think our teachers could do a better job of instilling the spirit of learning by building. Build to learn, learn to build.

Be prepared for users

Earlier today, I did something as innocuous as setting up a profile on about.me, a profiles startup much like flavors.me.  When I signed up, it invited me to tweet my profile’s URL:

I set up my blog’s URL as part of this — but I didn’t have anything new on it at all. Surprisingly to me, a bunch of traffic came through, much more than usual, simply because of this one tweet and — apparently — how cool about.me is.

The takeaway is this: you’ve got a brand you’re showing to the world. If you give them some reason to come to your site, even a small one, you need to have something new for them. If you don’t, you’re only asking for dilution of your “personal brand”, something that’s been mused about frequently by my friend Ted Gonder — on his much more actively “branded” personal blog .

How to give feedback well

In the course of a well-lived life, you’ll hopefully be asked to give feedback on someone’s hard work.  Sometimes you’ll be an expert in the domain (this happens most often in the workplace, and is where you can get your best practice); and other times you’ll be armed only with extremely general knowledge to help someone out with something important, specific, and challenging even to them.

In the Web industry, we’re used to iterating on our own work — a concept that means we should always be revising and always squeezing the very best solution out of whatever problems we’re solving with that particular interface or interaction.  But I’m convinced that iterating on other people’s work builds the same sort of mental ‘muscles’ we need to be efficient at iterating on our own work, especially if we know nothing about their stuff, because you’re tasked with three things:

1. Quickly parsing and understanding as intimately as possible what they’re working on so you’ll be any good at all;
2. Testing, using, reading, sampling, or experiencing their creation with a critical eye, regardless of if you know nothing about it;
3. and lastly, trying to give feedback that will be meaningful and helpful.

On Hacker News yesterday there was an example of a woman who, when asked for help on a web design, responded back with an entire slide deck of extremely valuable copy-editing feedback.  I found myself amazed by not only the quality of what she’d produced, but her willingness to help just a simple acquaintance with so much hard work, for free.

She must have gotten something out of it, even as a clear professional in that field, or she wouldn’t have done it. I found myself thinking of the ways she must have benefited, but knew I was often reluctant to give feedback myself, and wanted to get the same benefits she was able to get.  So let’s go back up to the three tasks before and turn them into benefits:

1. Quickly parsing and understanding as intimately as possible what they’re working on so you’ll be any good at all; She tasked herself with learning his value proposition, business model, and key purpose as an outsider.  This kind of design review was invaluable because it provided the creator with both an outsider perspective and professional feedback; and being able to do that as a professional will make all your marketing better, because you’ve completed the arduous achievement of turning off the designer in you. Key Benefit: She was able to practice being a “normal”.
2. Testing, using, reading, sampling, or experiencing their creation with a critical eye, regardless of if you know nothing about it; This too is really hard for many professionals; snapping out of their one-track mode of common work (whether it be web design or something else) and into the challenge of critiquing something you know nothing about will force you to learn something new and, in the process, get your creativity flowing in your own work.  In order to give actual meaningful feedback, too, you’ll have to expand your own brain. Key Benefit: She was able to spike her creativity and learn lessons from someone else’s work.
3. and lastly, trying to give feedback that will be meaningful and helpful. Many people might think that they shouldn’t talk assertively or authoritatively when reviewing someone else’s work. The truth is that that’s really the only way critique should be given if it is to mean anything at all.  Giving critique passionately but genuinely will enable you to take critique better yourself, and to understand where people are coming from.  Key Benefit: Through critiqueing other people, you learn how to extract the best nuggets from other people’s criticism of your own work. However: Don’t critique someone’s work too confidently, either positively or negatively, unless you’ve done the former two steps.  If you haven’t, you might lead them down an erroneous path.

On the Restaurant Industry, the Newspaper Industry, and Other Symbiotic Industries

Every morning when I wake up, the news comes to me.  It doesn’t slap onto my front porch at some ungodly hour (I’ve seen the weary travelers who deliver these newspapers in the morning, always the sign of a good night out).  It’s not delivered by a person to me.  I don’t even take the paper; I don’t have to go down to the corner, tipping hats at friends and acquaintances on my way to the corner store or newsstand to buy a daily edition (of which I actually have at least 3 options within walking distance).

But like I said, the news comes to me.  It bleeps onto my iPhone and my waking-up procedure has gone from a quick check to make sure there’s been no texts or calls to reading the entire contents of the Chicago Tribune iPhone app.

From this...

...To this

I’m more informed, better at parties, et cetera.  But what I’m not doing, necessarily, is heading down to the neighborhood diner to discuss the news with my closest friends over coffee.  Now obviously, mostly retired people do that, but back in high school, I would occasionally meet friends at a very old-school diner right by our high school before going in for the day.  We didn’t always discuss news, and the only papers offered were lousy local ones, but I digress.  The point is, anybody can do it.  It’s a community thing, not a news thing, or a restaurant thing (those greasy spoons weren’t worth the trip without the friends).

Now I’m aware that social media and new tech have killed a lot of industries, but I’m not sure if people foresaw neighborhood diners and breakfast places closing because everybody reads the news alone on their smartphones nowadays. But it’s certainly true – there was one right by my old apartment that drastically cut its hours in response to fewer customers; right in front of the restaurant, there was a dozen-long row of (mostly full) periodical cases and newspaper machines.  The juxtaposition got me thinking, and here we are.

My point is not really to lament the death of coffee klatches, it’s to comment on the secondary and tertiary casualties in this ‘new’ economy, ‘new’ media, ‘new’-just-about-everything world.  As a web designer and computer science student, and a person that’s infatuated with old Americana and had family members who love to talk about days gone by, I see a conflict forming between what I do in my work and how rapidly the world changes.  So much of what ‘makes men men’ and made the good old days the good old days has shifted due to my industry.  Maybe I’m so interested in all that stuff because someone has to eulogize it as it goes down.

So, in sum: Investors need to be aware that there can be crazy, completely unforeseen, domino effects on industries as seemingly intrenched and immovable as a breakfast diner.  It’s not a ‘brave new world’ or anything — this is more of a reminder.  You probably should have gotten out of telegraph-machine manufacturers in the 20s.  It’s not hard.  You just have to look a lot harder as an investor today.  Allowing myself to even make wild guesses about what location services like Foursquare mean for nightlife and entertainment industries seems impossible, but if I was investing, I’d have to be doing it.