dealing with the imperfections

One of the things that drove me to entrepreneurship was my constant frustration with the inadequacy of the products & services that I encountered. From the long wait times on customer service calls to the shoddy service at a local diner, to the poorly organized shelves at a local department store, everywhere I looked I saw ways that the businesses I interacted with could be better.

For a long time I wondered, why don't the owners or managers of these businesses take more pride in their work? How can they stand by and deliver this sub-standard service to their customers? I wanted to be in charge, so that I could achieve the perfection that was so lacking in the world as I found it.

Now that I run my own business, I've discovered the truth on the other side of the coin: that given the explicit constraint in resources, a business owner has no choice but to decide which parts of the business will remain imperfect, and indeed must remain imperfect for the business to succeed.

Creating a business requires mastery of prioritization. Given a list of a thousand things we could be spending our time on, we have to pick a few of them to actually execute. Especially early on, we must, must make the decision to do a few things exceedingly well, rather than doing many things satisfactorily. We thus organize our resources so that majority of our effort focuses on the minority of initiatives that matter most.

This can be frustrating. There are about ten thousand things about CourseHorse that I would like to be better. I have great long lists of them in my head, and each time I experience them in our product, I cringe. Then, I remind myself that it's a choice we've made. That today, we are specifically abandoning perfection in nearly every aspect of the business, in order to pursue it on one particular front. That we care deeply, but that it's a tough love, that requires tough decisions.

As my thinking on the subject has matured, I've realized that one ethos that can vary from business to business is the question of how to prioritize. At CourseHorse we learned to intimately understand the needs of the end-user, and to use those needs as the organization's guiding light.

Yet different users have different needs, forcing a business to decide which needs matter most, and how it will deliver against those needs. These decisions come from the organization's values, which reside within the DNA of the founders. For instance, in a restaurant , does the founder care more about having the best tasting burger in town, or the fastest meal in town, or the kindest, most helpful servers in town? Each of these meets a specific customer need, yet a deep focus on any of them can negatively impact the others.

Now, when I encounter businesses, I try to understand the mind of the founders, based on what the company excels at, and where it falls short. How did they undergo that impossible task of carving out priorities? I take it for granted that they know the flaws & issues I'm encountering, and I empathize in solidarity - the imperfections are hard to stomach, but they make the pursuit of perfection possible.

leaping off rocks

I am afraid of heights.

I think it began when I was about ten years old. I was swinging on a vine over a steep hill in my backyard, and (of course) it snapped. I plummeted maybe about 20 feet and broke my wrist. If I put my mind to it, it's possible for me to imagine the feeling just before the fall. My sudden, unsupported weight, and the wild fear that accompanied it. I have been afraid of heights since that day.

In September, our team went on its first 'company retreat'. We spend labor day weekend in Westport Massachusetts, sharing a house near the beach. It was a fantastic weekend. Beautiful weather, incredible food, lots of healthy brainstorming, strategy and soul searching about who we want to become as a company, and as people.

We started every day by biking/running to the beach and diving into the Long Island Sound. On the coastline of Westport, there's a famous rock about 100 yards into the water. It's named Elephant Rock because from a certain angle, it looks uncannily like - you guessed it - an elephant bathing in the water. Upon swimming out to the rock, we discovered that there were places to jump from the rock into the water. There were three heights to jump from, and on the first day, without thinking about it, I ran off the lowest ledge into the water, and swam back to shore.

Immediately upon reaching the beach, I knew.
I had to jump from that middle height.

The whole day, the thought kept surfacing, until the next morning, it was all I could think. I swam out to the rock in anticipation, and of course, as I stared over the edge, my courage failed me. I hemmed and hawed, practiced the steps I would take before leaping, felt slightly sick. And then with a slow exhale, I made the mental leap and then made the physical one.

The moment I surfaced, again I knew.
I couldn't walk away without leaping off the precipice.

And so the next morning, I found myself back. This leap was actually a bit dangerous. The cliff of the rock was not sheer - it sloped out into the water. That meant you really needed to build a bit of momentum before jumping, or you'd hit the rock on the way down, which would almost certainly break a bone before you plunged into deep water. To make matters worse, the 'runway' was slippery, dusty with seagull droppings, and uneven. Hard to find good secure steps to build speed with.

Fear is a difficult thing to empathize with. Many fears are shared by everyone, but when people have fears that you genuinely don't share, it's nearly impossible to step into their shoes. Realistically, it was just a rock, and some water. I had probably jumped from higher heights as a child. And yet. I could feel my uneasiness spiking, the nausea swirling in my stomach as I peered off the edge.

What if I slipped? While running off the ledge, I lost my footing and slipped off the side, hit my head and collapsed into the water? There wasn't a lifeguard, and my friends could hardly be called strong swimmers. What if I jumped too soon and hit the rock on the way down? Why the heck was I doing this? There's no shame in walking away, you're not proving anything to anyone. Yes, it's ok, let's not split our head open.

There is a point in all our lives when we define our relationship with fear. There is nearly no pain that the external world can cause us like the pain we cause ourselves, and fear is one of our own biggest antagonists. It is not real. It is in our heads. And at some point, anyone searching for freedom has to step into the fire of their fear to discover that it doesn't burn.

And so I leaped.

I think about that moment whenever I encounter fear. Hell, if I leaped off that rock, then I can deal with this bullshit. Leap again, son. Like an anthem it has defined my approach to the things I'm uncomfortable with. Oh, you're worried about this? Time to leap. Time to leap, let's go. I find myself constantly searching for the next, higher rock to leap off of, actually searching for fears so that I can go put them to rest.

What sweet liberation, from a single moment.
It is incredible to think that we face such moments every day.
That the opportunity to change everything presents itself every day.

"This man leaped off a rock once."

I think I'd be alright with that on my tombstone.

taking ownership

I've been thinking about what it means to take ownership over something.

As a consultant, I learned that one of the key steps in strong project management is to ensure that every workstream or project had someone designated as the "Owner". It was this person's job to break down all the barriers in the way of getting that specific item accomplished successfully. At the end of the day, that person was responsible for making sure that piece of work was completed, and was accountable for any delays and errors in the work.

Until you take ownership over something, you will always find yourself to be a bit detached from the success of the project or initiative. Even as a competent employee, it's easier to be careless because the buck stops somewhere else. You have the luxury of waiting to be told what to do, of asking before you take any next steps, of letting someone else follow up on the details and worry about quality of the deliverable. When the day ends, you unplug completely and forget about the work until the next day.

Yet there's a point in every ambitious person's career when they must stop waiting for directions to be issued to them, and must start looking at the canvas on their own to decide which lines to paint next. They must stop asking for permission to take the next steps, stop letting others decide what 'done well' means, and move boldly ahead to do whatever it takes to execute.

Owners act differently in several ways:

• They take ownership of things they have not been specifically assigned ownership over
• They set deadlines for themselves, even when no one calls for a deadline to be set
• They move Heaven and Earth to hit those deadlines
• They seek measurement and structure for the milestones and make sure to get outside feedback when necessary, even when not specifically instructed to do so
• When they hit a wall, they explore all possible solutions until the problem is solved
• They are unafraid to stand up and ask for (or demand) help
• The owner never leaves things 'up to someone else', unless that person has been clearly established as the owner of the specific task
• When necessary, they pick up someone else's work and get it done properly
• When no one else has the bandwidth to own a task, the owner adds it to their own list
• They are excellent at keeping everyone aware of the progress of the project & the barriers preventing it from getting done
• The project they own is always on their minds; like a chess game, they are constantly thinking several steps ahead to what is coming and how they will accomplish it, as well as the weak points in their current strategy

As I look through this list, 'ownership' sounds a lot like 'leadership'.

And, as with leadership, very rarely is it specifically assigned; most often, it must be assumed by the leader. Luckily, when someone steps up, the rest recognize and respect it immediately.

Have you started taking ownership yet, or are you still taking orders?

#sandy

All week I've been thinking about how impossible it is to learn something without experiencing it. Even with all the hurricane tips we read on the web (and learned last year for Irene), we couldn't properly prep for losing power for a week in the city. In the end we fared just fine, but now that we know that devastating hurricanes are a New York reality, I can't help feeling like we'll be so much better prepared for the next one.

From little things like having backup matches and batteries, to charging all electronics, cleaning all the dishes and doing the laundry before the storm hits, and of course knowing which groceries make the most sense to buy - it's funny how you can be told a dozen times what to do but it doesn't sink in until you live through it once. Next time we'll have confidence that we can light the stove with just a match and flush a toilet with a pot of water from the bathtub. We'll be prepared for a week without working cell phones, which was a big surprise this time around.

Ultimately, we were prepped enough that I didn't venture out till Tuesday evening. Exploring the powerless cityscape was itself instructive, aside from seeing just how much impact electricity has on the aesthetics of a city. The street gossip and little games of 'telephone' spreading rumors were marvelous to watch and take part in. The most interesting rumor I heard came from the 7-11 guy who said that the transformer on 14th street exploded because someone stole the sandbags protecting it. Still don't know whether that's true. Most of the rumor hotspots were stores like 7-11 - miraculously open, with owners delivering goods to customers outside, balancing their desire to move product without risking theft within their darkened aisles.

I stayed in Stuytown until Wednesday morning, and getting out to the upper west side held yet another set of revelations. To be clear, aside from a fallen tree and the lack of power, not a single thing was different about my street - there were no massive pools of water and no apparent destruction when I emerged, making me wonder just how bad the hurricane had been. Then, jumping on the internet, I found pictures of 14th street and Stuytown that showed the area entirely underwater, saw a youtube video of the transformer explosion and finally understood the urgent nature of messages that had come my way. Incredible that you can be so close to the disaster without being touched by it. People I spoke with later asked whether I had escaped Stuytown by boat (I caught a cab).

This weekend was, I'm ashamed to admit, the first time I've ever volunteered for disaster relief. My biggest lesson was to start helping way sooner - in any disaster, the least help is available early, when it's perhaps needed the most. Then everyone gets power back and there's a flood of supplies and volunteers, so much so that community centers and outposts were literally turning people away. I used Twitter's #sandyvolunteer hashtag and biked around to help who I could. In Manhattan, we ran food and water up 30 flights to elderly folks in powerless buildings. They needed the supplies just as much as they needed someone to talk to, to bring them news and assure them that they'd be ok. In Staten Island, we delivered food and clothing from Manhattan by bike and then helped organize it. I've only ever thought about the act of donating the goods, but so much effort has to go into organizing the assets for efficient distribution. Little things like labeling the bags of clothes as "Women's pants" or "Hats and gloves" make a huge difference.

Finally made it to the south shore of Staten Island on Sunday, and I don't have the words for it. The water had flushed through people's homes, destroyed every single one of their possessions, and then dumped everything in their yards and on the street. Every house had a green, yellow or red sign on it to let people know which homes were still inhabitable. I saw no green. Help cleaning up was and likely still is the number one thing that volunteers are needed for. You just put on gloves and start carrying destroyed stuff from people's houses into the street and eventually into the garbage trucks. The unsung heroes I saw there were the garbage men. They were kind and gentle with the victims, but relentless in their clearing of the streets and homes - no breaks, no complaints - they simply did not stop, and they were literally moving mountains (it's also incredible to watch a hydraulic garbage truck swallow a washer, dryer and refrigerator without missing a beat).

It's weird to say, but I didn't see many openly unhappy people. There was only work to be done and people doing it. Everyone was looking to the next step, the next day until things are right again, and they will be. Sandy hurt us badly, but we'll be back.

What's scarier to think about is that we knew weeks in advance that it was coming, and had plenty of time to prepare, and still got hit hard. Makes me want to get seriously prepped for the disaster that's going to come without any warning.

how to say nothing in 500 words: a startup guide

Last post was about a great essay, how to say nothing in 500 words.

As I reread it, I realized that it also reads as a guide to startups.
Allow me to reinterpret the following rules:

"Avoid the Obvious Content"
Marketing 101. Make a list of 'what types of content everyone else is writing' and then willfully do the opposite. You will never stand out by copying others.

"Take the Less Usual Side"
No one ever created a revolution by doing things the 'normal way'. Disagree, often. When industry says, 'this is the way we do business', do it differently anyway. But, do not compromise on the basics, like integrity.

"Slip out of Abstraction"
No pitch ever convinced anyone with abstraction. Never say 'game-changing' (tell us what's unique), 'huge opportunity' (tell us how huge), or call yourself a 'rockstar' (show us what you've created).

"Get Rid of Obvious Padding"
I fall short here. I actually find that more padding (with time/cost estimates & financial projections) is actually a better thing. Everyone sees through it, but it's an unfortunately reality that people have been trained to expect it - they automatically adjust downwards no matter what numbers you show them.

"Call a Fool a Fool"
Be direct. No one has time to beat around the bush. Address the hardest issues first. Provide feedback often (but in private). Fire quickly. Be open about the problems facing the company, and confront them as a team, head on.

"Beware of Pat Expressions"
Beware of "common knowledge". Axioms we held true about usage, engagement, virality are changing so fast that yesterday truths are tomorrow's icebergs. Test everything, find your own truth.

"Colorful Words"
Stand out. Drive memorability by delivering a stellar, unique experience.

"Colored Words"
Be aware of your universe. Know what your customers are used to, and take this into account when you build for them.

"Colorless Words"
Quit your day job. Start a company.