On the Edge

Twenty-somethings: PAY ATTENTION

Tue, 07 Sep 2010 09:59:24 -0400

correlationstonone:

evangotlib:

Don: That’s your job! I give you money, you give me ideas!

Peggy: And you never say thank you!

Don: That’s what the money is for! You are young. You will get your recognition. And honestly, it is absolutely ridiculous to be two years into your career and counting your ideas. Everything to you is an opportunity.

Really? So let your future stars stew? Diminish their initial accomplishments? Push the date of recognition out into the future instead of acknowledging progression?

30+ somethings: if you think being austere and distant while judiciously ladling subtle pats on the back once a lifetime is motivating us, you’re right in a sense. It is motivating us to leave. I’m not sticking around at a firm that doesn’t acknowledge my efforts expediently, and that’s a problem for you, because I’m good. Too much of this attitude and you’re going to look to the backbone of a firm full of grunts with no qualifications beyond an inability to move on. You’re supposed to cultivate strong personalities with big ideas, not let them starve! They’re your future leaders!

The whole point of Mad Men is that you aren’t supposed to be emulating these people. They are not examples, they are terrible warnings; Don Draper is an awful boss who doesn’t understand how to relate to people. That’s why he fails - because no one in his life gets what they need, and his individual brilliance is never quite enough to compensate. So the next time you do a side-part and put on a fedora, keep in mind you’re wearing a costume that says “I don’t understand my favorite television show.” And if you manage like him, you shouldn’t expect success.

First of all, a bit of context which may be helpful. I am 27. I’m somewhere in between my “twenties” and my “thirties.” I also run a company of about thirty people. So my opinion on this scene — and the relative merits of its “advice” — comes with that background. I have also at times sought praise too much (my first grade teacher actually commented on this on my first report card: “Michael seeks praise and reinforcement too often”) and I’ve had to readjust my approach.

I think that the scene is extremely valuable and contains real insight that should be helpful to people regardless of age. Here’s why: as an adult you should have the strength of character that allows you to determine, somewhat definitively, whether or not you are doing a good job. If you need constant pats on the back to know that you are doing a good job, or to stroke your ego, you need to spend more time developing your sense of self. Spending your life waiting for and relying on external validation is a very poor way to live.

Apart from that one central takeaway is this: as an employee — or, really, as a person — you should not need and you should not expect constant positive reinforcement. As an employer — or, really, as a person — you should not feel the need to offer constant positive reinforcement. That said, people should offer praise when it’s due and earned. Saying “good job” doesn’t cost anyone anything and it can in fact be very beneficial. But not for the sake of saying “good job” — instead praise should be offered for good work that you would like to see more of. Praise shouldn’t be given so much that it loses its meaning.

I think the reason why this scene resonates so much is that there are lot of people out there — many in their twenties — who rely on external positive input for their sense of self and achievement. These same people often seem to miss the subtle hints that they are not doing a good job. It’s almost like feedback has been cheapened: the norm is overwhelming positive feedback. If one does a really excellent job the praise must be turned up to 11. Even worse, when someone does a poor job — or just a middling job — the lack of praise isn’t enough to deliver the message that the job done is not good.

This generation does not do well with “you could have done that better.” The result of such feedback should be self-examination and questions about how to do the job better next time. Instead, too often, the result is “why don’t you like me?” or “why don’t you value me?” This should not be the takeaway: the takeaway should be “how can I do a better job next time?”

Again, this all comes back to having a healthy and strong sense of self. If your ego is in the “right” place you should be able to know that you’re doing a good job without other people telling you so… and you should be able to understand that you’re doing a poor job and can improve without too much prodding. The truth is that in a work environment you’re paid to do a good job, and your reward is your paycheck. It’s up to you to make the most of it. A good manager will also mentor you and tell you when you’re doing well and when you’re not… but it is not the job of your manager to be your ego stroker.

Much of this season of Mad Men has focussed on the generation gap between the older, established players (Don, Roger), the younger up-and-comers (Peggy, Pete) and those who sit between both worlds (Joan). It’s great to see the show’s thematic content used as fodder for discussion about today’s workplace. Clearly, the inter-generational push-and-pull is nothing new, but I think Mike brings up a really good point about the new “norm” of feedback: a baseline positive. It probably derives from an educational background of “good effort! that’s not quite right, but you should be proud of how hard you tried”, or something along those lines. When you reach a workplace environment where there’s just not enough time for such pleasantries, or stakes are too high for such feedback, a response like “this is wrong, go back and try again” becomes absolutely crushing - not because it’s particularly negative (like Don’s “You should be thanking me every morning when you wake up, along with Jesus, for giving you another day!”), but because anything LESS than positive feedback is negative.

It’s not a clearcut issue of young workers needing to re-evaluate their workplace expectations. I know I’ve been frustrated in the past for receiving less-than-positive feedback from a boss for whom I have little-to-no respect (ie a career middle manager). The interesting part of all this is that I actually CRAVE constructive criticism from a mentor or manager I admire - in order to improve my own skills. It’s why I’d really advocate an apprenticeship model for developers, since I think an association with a mentor could do more to improve someone’s coding and design thinking than any number of books, no matter how well presented.

Worthless iTV Conjecture

Wed, 25 Aug 2010 13:15:38 -0400

I figured I’d join in the wildly uninformed conjecture about Apple’s new iTV, specifically its user interface. Speculating about future Apple products is as fun (and inaccurate) as predicting plot outcomes on Lost, and since that show’s off the air, all I have left now is Apple keynotes. I hoped Rubicon might fill that gap, but that show’s turning out to be as boring as watching paint dry.

Anyway. Lots of speculation over the new iTV interface. (If you’re new to the iTV, the successor to Apple’s Apple TV, you can read up about it at Engadget.) With the iTV running iOS, how will the UI adjust to handle the lack of touch? I think a remote-controlled cursor system is WAY too inelegant for an Apple implementation… but what other option do they have?

They’ll simply add a requirement to the device: in addition to buying the $99 iTV, you’ll also need to own an iOS4 capable Apple touch device. This move would be so typical of Apple for a number of reasons:

They’re lowering the price of one product but requiring the purchase of another product, thus keeping the revenue stream level. Hell, they might even be taking a loss on iTV units (or breaking even)
Encourages the continued expansion of the iPhone
Adds a killer app for the iPad
Will annoy a LOT of people
Allows Apple to deliver a truly fantastic UX

In this scenario, your mobile device (iPhone, iPod Touch, iPad) has an iTV remote app. The app is simply a mirror of your iTV screen. Interacting with the iTV remote app alters the content on the screen. Changing the content on the remote changes the content of the tv screen. In such a scenario, for your primary interaction with the device (control), you’ll be looking just at the remote. You’ll only start looking at your tv screen once you’ve loaded content (ie selected a show, a movie, a song, whatever).

By requiring an iOS 4 device, the remote app can work in the background, so you can load content via the remote, start watching on the tv, switch to Mail or Safari on your iPhone, then pull the remote app back up from the tray when you want.

There’s also some opportunity for some amazing future expansion here. Imagine “pairing” apps for iTV and iPhone/iPad - for example, an MLB app that streams games to the iTV while showing matching content on your “remote”, ie statistics based on the current batter, pitcher, whatever. Or an IMDB app paired with a movie app. A music lyrics app paired with iTV iTunes. Etc. The ability to pair apps, for a developer, would lead to amazing creative opportunities AND an increased revenue stream.

This move would tick off a lot of people. But it would make for an incredible product.

What’s YOUR worthless iTV conjecture?

Just saw that Alfred, a free search and launcher app for Mac (a...

Wed, 25 Aug 2010 10:32:39 -0400

Just saw that Alfred, a free search and launcher app for Mac (a modern cousin to Quicksilver), has just released an early version of its PowerPack, a paid addon that begins to add real power to the base app. Check it out if you’re a fan of keyboard-driven productivity.

Looking pensive on Governors Island.

Wed, 25 Aug 2010 10:22:20 -0400

Looking pensive on Governors Island.

Maniacal Rage: The Problem with Facebook's "Places"

Tue, 24 Aug 2010 13:26:44 -0400

Maniacal Rage: The Problem with Facebook's "Places":

That’s the problem with Facebook. They are slowly destroying independent web applications with boring versions that immediately win due to Facebook’s population (which at this point is the 3rd largest country on earth). There’s no demand for excellence. Just make sure the feature list keeps growing.

Hopefully, though, independent web apps can maintain their own user base (and quality) while integrating with Facebook’s ecosystem. Sort of the Apple “it’s profit not market share” attitude.

merlin: theimpossiblecool: Ms. Hepburn in full...

Mon, 23 Aug 2010 15:17:31 -0400

merlin:

theimpossiblecool:

Ms. Hepburn in full color.

Jiminy.

Fascinating to me that this look is EXACTLY on trend right now.

I downloaded Calvetica earlier this week after reading an...

Fri, 20 Aug 2010 12:46:25 -0400

I downloaded Calvetica earlier this week after reading an explanation of the theory behind it from the app’s creator, Rob Foster. I didn’t want to post too soon about this, but after seeing the link from Dave, I wanted to add my $0.02.

This app is really, really good.

I’ve spent a lot of time (and money) experimenting with to-do methodologies. I’ve read Getting Things Done. I’ve tried Things (for Mac, iPhone, and iPad), Omnifocus (Mac and iPhone), RememberTheMilk, Taskpaper, a hipster PDA, pretty much everything you can thing of. And I didn’t stick with any of these approaches. I never felt as if they bought me that “peace of mind” that they advertise - sure, all my tasks were kept in one place, but I had to spend a good amount of time organizing the tasks, tagging the tasks, tracking the tasks, and being reminded of all the crap I hadn’t done yet, and don’t you feel like a failure you little twerp, you have 500 items across these four projects and you’ll never finish them all and you’ll die a miserable failure.

So yeah. My lack of success with these methodologies and apps might reflect more on me than on the apps themselves.

Calvetica changes all that. I bought in on a whim - it looked pretty, and was described as being quite fast, so I was curious to play with it if only from an iPhone development perspective. After entering my tasks for the rest of the week into it, I went through my day as normal. The shocking realization came the next morning: I had slept better. I felt less stressed.

The theory behind Calvetica works perfectly for me. It provides you with the storage medium - think of a task, get it out of your head immediately and into a trusted system - that GTD demands as the basis for any task management approach. It forces you to schedule time to perform or reflect on a task, which I think is particularly helpful for me as I switch between different roles during the day. But Calvetica wins over a traditional calendar system with its quick entry and quick deferment. If a reminder to perform a task comes up, and you’re busy with something else, just snooze it - for 10 min or 2 days, whatever makes sense. You know that you’ll still get that reminder, the task is still there, but you’re clear to continue your immediate work without having too much of a mental interruption.

Beyond that, you’re never presented with a master list of EVERYTHING you have to do. For me, that’s really important, since I’ve found myself intimidated by my to-do lists in the past.

If you’ve struggled with task management approaches, reach Rob’s methodology up above, and then try out Calvetica. I think you’ll like it.

Is the New Virb for Me?

Thu, 19 Aug 2010 14:12:24 -0400

Is the New Virb for Me?:

cameronmoll:

An excellent write-up by Virb design extraordinaire Ryan Sims. The new Virb, which launched Monday, focuses on building an elegantly simple website for $10/month.

I actually appreciate that they’ve launched with no theme previews or sites featured. While those are certainly important for convincing users to sign up, it shows the Virb team isn’t frightened by placeholders that would normally postpone a launch. There’s very little need to launch perfectly baked anymore.

For its intended audience (content creators beyond bloggers), Virb looks like a pretty fantastic resource.

"When people offer unpaid gigs by saying, it’s “good exposure,” I like to ask how much exposure they..."

Thu, 19 Aug 2010 10:19:54 -0400

“When people offer unpaid gigs by saying, it’s “good exposure,” I like to ask how much exposure they made last year.”

- Merlin Mann (via soupsoup)

daverosado: soupsoup: Facebook Places is basically a...

Wed, 18 Aug 2010 22:05:24 -0400

daverosado:

soupsoup:

Facebook Places is basically a Foursquare clone, as expected.

One really nice feature is your friends have to opt-out of you checking them in, awesome, and so Facebook. That’s right, your friends can check you in, even if you didn’t check in yourself. It’s almost as if Facebook wants you to hate them.

People can create a “Place” for your house. At first it’s private, but if enough people check in, it becomes public.

Because of Facebook’s size, it takes all privacy issues location apps have wrestled with for over 10 years (Dodgeball) and cranks them up to 11.

Think you hated seeing all those Foursquare check-ins in your stream, well get ready to see 500 million users checking into your stream on Twitter and Facebook.

Location based apps are great, if they stay in their silos. Facebook and Twitter streams shouldn’t have check in’s polluting the stream. Currently the only twitter app I know that lets you filter out location check ins is Tweet Deck.

Here’s an excellent, concise look into the just-announced Facebook Places, which is basically garbage, but is mainly a Foursquare clone. Why would anybody want to check into their own house? Why would anybody want to see a long series of Facebook updates that read “Johnathan Doeford just checked in at Jamba Juice and you totally care!”?

Now, people who know me know that I’m a Foursquare user and are currently sharpening their pitchforks and flags that say “hypocrite!” on them. Well, relax, because murder and public ridicule won’t solve anything, but really relax because I use Foursquare in its own isolated way. I like to read tips, get badges, and piss someone off when I take their mayorship. 99% of the time, unless I actually have a thought to share, I never tweet or Facebook update with my Foursquare check-ins, because you don’t care, trust me.

Therefore, Facebook Places, I already think, is a fail.

My first GPOYW! From a lobster bake in Eastham, MA. Picture...

Wed, 18 Aug 2010 10:19:46 -0400

My first GPOYW! From a lobster bake in Eastham, MA. Picture courtesy of cheeryobs.

"Only termites, naked mole rats and certain insects like ants and bees construct social networks as..."

Wed, 18 Aug 2010 09:48:35 -0400

“Only termites, naked mole rats and certain insects like ants and bees construct social networks as complex as those of human beings. In that elite little club, humans are the only ones who shop…Current research suggests that, unlike consumption of material goods, spending on leisure and services typically strengthens social bonds, which in turn helps amplify happiness. (Academics are already in broad agreement that there is a strong correlation between the quality of people’s relationships and their happiness; hence, anything that promotes stronger social bonds has a good chance of making us feel all warm and fuzzy.)”

- Consumers Find Ways to Spend Less and Find Happiness (via jayparkinsonmd)
I wonder if social bonds are strengthened when consumption isn’t generic (purchase from Amazon, or large brand like J. Crew) but is highly specialized (the boutique around the corner whose owner I know, the hardware store that’s had the same owners 50 years). I believe quite strongly that small businesses build and maintain the fabric of neighborhoods, but I’d be interested in the neurological ramifications of that belief (if they exist).

Private methods in Obj-C

Tue, 17 Aug 2010 13:42:00 -0400

Objective-C handles public/private/protected declarations differently than the languages of my current day-job (ActionScript3 and Java). I spent some time today looking into some differences with static accessors - namely, that “static” variables are class-specific declarations in Obj-C, whereas “extern” serves as a public static. Instance variables are by default protected, but can easily be marked @private or @public in a class’s header file.

Obj-C makes no difference among public/private/protected methods. I came across a really useful workaround for this language feature on StackOverflow. Basically, Obj-C 2.0 allows for the declaration of “empty categories” (categories are sort of like namespaced prototype changes) within a class implementation file, in which you can declare your “private” methods. Pretty useful!

The Perils of Follow-On Financing Decisions

Tue, 17 Aug 2010 10:32:31 -0400

caterpillarcowboy:

robgo:

I’ve been reading the book “The Black Swan” recently on the recommendation of my two partners. I had heard about the book for years, but it never made it off my “to-read” list until now.

One of the concepts that the book discusses is the way we think of risk differently when we are generating profits vs. when we are minimizing losses. The simple illustration goes something like this:

If someone gave you the offer of $100, no strings attached, vs. flipping a coin for the chance of winning $200, what would you choose? Although both options are mathematically equivalent, most folks would choose the $100.

On the flip side, if things were reversed, and you could either lose $100 for sure, or have a 50% chance of losing $200 or nothing, what would you choose? Most people in this situation tend to prefer the possibility of losing nothing, even though there is the 50% chance of a larger loss.

This illustrates a simple point that we tend to be irrationally risk tolerant in protecting capital. Social scientists call this loss aversion.

This has major implications for the venture business in the realm of follow-on investment decisions. It’s a part of the business that doesn’t get much attention, but consider this: I think it’s safe to say that well over 50% of a typical venture firm’s capital actually comes in after the initial investment round of financing for a company. So even if a fund is supposed to be “early stage” focused, the reality is that the bulk of their capital is going into the follow-on investments in the B, C, D and later rounds.

I didn’t realize this before I went into VC, but most VC firms are lifecycle investors, meaning that they have large reserves and expect to participate in most of the follow on rounds for companies that are doing reasonably well. One would think that the follow-on investing decision for VC’s would be an easy one. After all, no one has more information on a company than the existing investors and board directors. Therefore, they should be very well equipped in figuring out which companies deserve follow-on capital, and which ones don’t. Even though the follow-on capital is usually at a higher cost base than the earlier investments, this should be concentrated in the “best” companies, and should perform very well from a risk adjusted basis (even before considering the protection from being higher up in the preference stack).

Case closed right? Wrong. There are a lot of reasons why follow-on financings might happen when they shouldn’t, causing VC’s to “pour in good money after bad”.

Loss Aversion. As discussed above, the uber-reason this happens is that one is irrationally risk tolerant when trying to preserve capital. Or put another way, once you have a vested interest (time or money) into a company, you are willing to take irrational risks to protect your investment.

Delayed Gratification. No investor wants to see a “zero” on their track record, and no investor wants to report “zeros” to LP’s. This is true even though a small -100% return today might be much much better than a big -80% return in 5 years. The pressure of needing to raise a future fund, looking good in front of your partners, trying to get promoted, trying to look like a clever guy in the twitterverse, etc leads to unnecessary risk-taking in follow-on financing decisions. Even though almost every firm says they evaluate follow-on rounds like “new deals”, I think this is actually far from reality.

The Signaling Death Spiral. Let’s take the hypothetical case of a company raising a series B that is doing ok, but not great. The existing investors will often say they will support the company but have an outside lead price the round. The new investor will ask the existing investors if they are “in” for their pro rata as a signal that it’s worth investing. If an outside lead is willing to price and lead a round, it’s very very hard for the existing investor to say “you know what, I don’t believe in this. I’m going to pass on this investment and risk that the whole deal blows up” (note that this is different than the follow-on dynamics of VC led seeds, where the investor will have a much smaller % of capital at risk and knows that they are buying 5 options to make 1 true investment.) So in this scenario, a follow-on round gets done, and both parties are heavily influenced by the fact that the other is investing. Puzzling no?

Confirmation Bias. This is the tendency for people to favor information that confirms their preconceptions regardless of whether that information is true or complete. When layered in with Loss Aversion, it creates a deadly combination. Because an investor is averse to losses, he/she is biased against any data that suggests that the initial investment decision was a mistake and will gravitate towards information that supports a follow-on investment.

The Bridge to Nowhere. Even if a company is really struggling, the following logic is very appealing: wouldn’t you be willing to spend $2M to save the last $8M? Because investors usually buy preferred stock, they get paid first and so they only need the company to sell for the value of the preferred stock to get their money back. As a result, you often see struggling companies raise inside rounds under this logic (often crushing the employee’s equity in the process). But many times, this round of “bridge” financing ends up being a bridge to nowhere.

So, follow-on investing ends up being a much more complicated endeavor than it would first appear. Clearly, there are some firms out there that have a great deal of discipline about follow-on financing and have been very successful. But I think that this is a very very easy way to falter as an investor because it’s so natural to fall prey to these pitfalls. As some super-angel funds increase in size, it will be interesting to see how they deal with these hurdles as well. It’s easy to say that one will “pile in on their winners”, but the ability to do so will cut both ways.

Excellent post. (Again!)

Really good stuff here. I’ve slowly been realizing that people in general, and certainly individual persons, behave far differently than the relatively rational actors I would expect them to be. Also, The Black Swan is a fantastic book, even if Taleb’s writing occasionally veers into pontification mode.

All this mosque talk just makes me wonder.

Mon, 16 Aug 2010 17:10:45 -0400

jayparkinsonmd:

Can’t NYC just be our own country?

I’ve been wondering the same thing lately. It’s an interesting thought experiment, at least - how would NYC exist as a city-state? (Along the lines of Singapore, I’m thinking). If it included its surrounding foodshed, how self-sustaining could it be?

caterpillarcowboy: (via soupsoup) Amazing. That money could...

Mon, 16 Aug 2010 09:55:41 -0400

caterpillarcowboy:

(via soupsoup)

Amazing.

That money could definitely be put to some interesting uses.

Now, where’s my Hulu Plus invite, dammit?!

cheeryobservations: Justin’s Sunday morning breakfast: peach...

Mon, 16 Aug 2010 09:52:40 -0400

cheeryobservations:

Justin’s Sunday morning breakfast: peach pancakes w/raspberries and maple syrup. Served w/Stumptown coffee and OJ

Breakfast Sunday morning. We had picked up the maple syrup from Ledgenear Farm at New Amsterdam market a couple months ago, and it’s basically liquified crack.

I’ve been starting with iOS dev, which has led me to...

Thu, 12 Aug 2010 14:41:00 -0400

I’ve been starting with iOS dev, which has led me to learning xCode. All my previous development experience has been in Eclipse (for Flex and Java work) and various text editors, predominantly Textmate, for Ruby and HTML/JS/CSS etc, so it’s really interesting to start learning the ins-and-outs of a new IDE. Today I discovered conditional debugging… and wow. This feature could’ve saved me SO MUCH TIME when working on Flex debugging in Eclipse. Loving it.

msg: I was stalking my buddy Andy Weissman because I wanted to...

Thu, 12 Aug 2010 13:29:42 -0400

msg:

I was stalking my buddy Andy Weissman because I wanted to find his blog url and he called me out on it.

THIS is an absolutely FANTASTIC idea!

Analog Living in a Digital World

Thu, 12 Aug 2010 13:21:30 -0400

Analog Living in a Digital World:

jayparkinsonmd:

This has been my argument for quite some time. We’ve got 200,000 years of analog behavior ingrained in our hearts and souls. And then, literally all of a sudden within the course of a decade, something comes along that tries to treat our analog hearts and minds like highly streamlined digital communication machines, and we simply can’t keep up. And in fact, we’ll probably learn that we simply don’t even want “the future.” We’ll simply want what’s always been important for the past 200,000 years— the analog world of our close friends, family, wonderful experiences, creativity, and health. But I think we will want all of these analog worlds subtly augmented by interesting ways to connect our digital and analog lives.