The first thing people ask me when they haven’t seen me in a while is “How’s StepOut?”. I find it playfully amusing that, to others, I’m the “Indian online dating guy”. Not because I have any particular special amused sentiment towards India, online dating, or the web itself, just because it’s something I never thought I’d be doing professionally.
Work as Self
I used to hate pitching the company. Especially when, after the thrilling highs and sky-high expectations of being an early Techstars company, we were in the trough of sorrow. Later, when we started to become more successful, pitching the company became a source of pride for me. Funny thing how it tickles your ego to brag about how successful your fledgling project is. It makes you feel competent. Successful. Prideful. Like a leader who, at a time when the economy is in trouble and uncertainty in the world is high, is lighting the way towards for a plausible 21st century for our country.
One thing I never expected when starting this company was how, when you’re the founder of a startup, so your personal identity is coupled with your project. What’s dangerous about that is that startups, by their very definition, are extremely volatile. If you’re not careful, you’ll be so filled with pride that you’ll be walking on sunshine on one day and the next you’ll be filled with seemingly insurmountable nervous energy and anxiety.
I guess that’s why it’s so important to be internally motivated. If your ego depends on your money, your success, or any other 21st century status symbols to construct your idea of yourself, you are going to end up manic depressive. Especially since people have such an ability to normalize their personal situation with their surroundings. The startup scene in a hot market like Palo Alto or New York is like “Keeping up with the Joneses” on crack.
Immutable Identity
I suppose who you end up as as an adult is not necessarily who you thought you would be when you were a child. When I was filled with the naivety of a child, I used to think that my identity as an adult was immutable. It wouldn’t ever change. I’d be a grown up, and that’d be who I was. I’d have a job. And a car. And I’d drive to work and work 8 hours, and then come home to my wife. And that’d be the way it was for 40 years. It’d be like in The Simpsons where Homer never gets any older, and Bart is always in the fourth grade.
But the thing is; life isn’t like that. Identity is immutable. It’s always changing. It ebbs and flows. Day over day. Month over month.
In Zen Buddhism they teach the concept of the Original Identity. A novice meditator, unable to clear his mind of thoughts, is trained to ask the question “What did your face look like before you were born?“. It’s a proxy exercise for teaching understanding of the ‘self’.
Richard Linklater, director of the cult classic indie movie Waking Life puts it way more articulately than I ever could:
You know that thing Benedict Anderson says about identity? No?
Well, he’s talking about like, say, a baby picture.
So you pick up this picture, this two-dimensional image, and you say, “That’s me.”
Well, to connect this baby in this weird little image…
with yourself living and breathing in the present,
you have to make up a story like, “This was me when I was a year old,
“and later I had long hair, and then we moved to Riverdale,
and now here I am.”
So it takes a story that’s actually a fiction…
to make you and the baby in the picture identical to create your identity.
And the funny thing is, our cells are completely regenerating every seven years.
We’ve already become completely different people several times over,
and yet we always remain quintessentially ourselves.
What did your facebook look like before you were born?
Do you ever feel like you’re looking in the mirror when you look at your facebook profile? Try it. Your facebook profile is who you *choose* to present to the world. Maintaining this page is the digital equivalent to doing your hair in the bathroom mirror in the morning.
The earth-shattering thing about Facebook timeline is the explicit recognition by a major tech company of an idea as fundamentally radical as immutable identity. The timeline interface gives you a cohesive view of your self over time. Behind the glowing navigation on their UI is the potential for a lifetimes worth of nostalgia.
No wonder people come back every day.
What does postmodern personal private identity look like?
If a postmodern consumer is trained to look at their Facebook profile for their public identity, where will they look to understand their personal private self?
That’s a good question.
Before you go to bed tonight. Ask yourself: What is your self?
One of the biggest challenges you’ll faces as a technical co-founder of a social startup is that of equanimity.
You sit at the intersection of product and technology. The contrast in approaches in those areas is often under-stated and always under-recognized. In product, as CTO, you’re injected into the thought-stream torrent that results in strategic decision making, yet have little-to-no influence on the decision making process. Contrast with the technical world, where a startup CTO is given the keys to the car in regards to roadmap, technologies, and process.
It’s a dichotomy of roles for sure.
One might think that the divide between product strategy and tech is characterized by a language barrier between those that speak bits and bytes vs. those who don’t. But I think characterizing such as a digital divide doesn’t do us justice. Speaking code means that I am thinking about different things than those who don’t live and breath the technical minutiae of html tags, http sockets, 1s and 0s, hex color codes, if/else statements, do/while loops, free memory, and cpu utilization .
When the edge cases have edge cases
I am obsessed with edge cases. What happens if feature X is used in Y way? I’m constantly grasping with one of the core problems with running a social technology company. There is one variable that is greatly unknown to the technologist: the user. One’s mind is consumed with exploring the various possibilities as the blinking cursor haunts the empty source code file displayed in your IDE.
Technological direction is a core challenge. Wouldn’t it be cool if we built this feature with the latest & greatest? HTML5. Node.js. There’s a new ruby gem out that does that. Can’t CSS3 do that? Oh wait, we’re still supporting IE7. Whats our browser penetration there? Shit, we have a delivery deadline to meeting. Better get coding. Better to be wrong and ship than right and not shop, right?
The other half
How does the strategy team consume their time? Your guess may be just as good as mine, but I’d like to think I’ve spent enough time with them to make an educated guess. There are shades of grey, but I don’t think they don’t think about various edge cases as much as we do. They speak in MBA-nglish. Financials, legal, market share. On one hand their work is entirely emotionally expressive of the vision of the team. On the other extreme, supremely bland and detail oriented. They’re immersed in e-mail, photoshop, word documents, excel spreadsheets, and management software. Will the company have enough money to reach it’s next milestone? Do we have enough mindshare amongst investors? Amongst consumers? Engineering needs to ship that *yesterday* or we’re going to go bankrupt, oh and don’t forget the reporting piece, we’ve got data to collect.
I hesitate to generalize about all artists and all technologists. Which marks me right there, as an engineer by training. Trained to obsess about edge cases and tiny details — missing the forest for the trees makes no sense, the forest is just many individuals trees, repeated, at scale.
Which strikes to the heart of one of the key differences I’ve experienced watching and collaborating with artists.
As an engineer my creative act begins by removing ambiguity. What’s the simplest possible thing we can do? What’s the core of the idea? What’s the minimal viable product? When you say pigs should fly, is that sustained flight? Self powered? Do you mean flapping or simply moving through the air? Does flight imply control? Or would a porcine trebuchet get us to a version 1 beta? Maybe we could do some testing by putting a pig on top of a tall tower?
Artists I’ve worked with often take the opposite approach. How can we remove all the walls around this idea? How do we make the possibility space of this idea infinite? Flying pigs are really just an example of the impulse towards freedom that we’re trying to address, let’s not get too caught up on the pigs, or the flight.
Additionally as a technologist I’m often driven by an inner fantasy life of utility (and utopia) with a secret hope of broad impact. Artists seem compelled by the innate desire to express the inexpressible, and a secret hope of widely inspiring. Basely, the difference between being right and being true.
What’s striking about web startups is, that as a web startup, your product *is* your art.
Since we founded StepOut, I’ve noticed that everyone cares deeply about the output of their time. To some degree your identity is shaped by your hard work. This is the same for designers, engineers, and the biz dev team. If you’re an engineer of any level of passion, you care deeply about the product you are building, and such, emotionally connected to the design, the use, cases, the *flow* of the app. It’s *hard* not to be extremely opinionated about it’s direction and the priorities associated with the vision.
Often, I try to remind myself of faith in my team to make the right decisions. During that process, I’m remind myself of a personal trait that I’ve found encountered in a completely differently avenue of life, my daily meditation practice:
Equanimity (n) : mental or emotional stability or composure, especially under tension or strain; calmness; equilibrium.
The key to equanimity as a startup CTO is to realize that you are building the knobs and levers that your co-founders are tweaking. You are building the starship enterprise as it is being flown, but you are *not* Captain Kirk. You’re Spock. You provide the data that decisions are based upon. Many times it’s delivered precisely. But sometimes the data is wrong. Sometimes a lever breaks. Other times, something gets lost in translation.
The curious thing about Spock is that as a Vulcan, he was *born* without emotions. As a technologist, you *learn* to be in control of yours, have faith in your team, and be equanimitous. It’s a skill that is not taught to engineers in trade school.
Be Spock, Not Kirk
It’s *hard* not to get emotionally attached to the results that the dozens of technical decisions you make daily deliver. At the end of the day. You’re tired. Remind yourself that this is when you have to be equanimitous.
Sometimes the data you’re presenting to your co-founders validates the vision you have for your business. Often times it doesn’t. When it doesn’t that’s when you have to be equanimitous.
We’ve made business strategy decisions based upon bad data before. Data that I provided. 4 months into execution of a business strategy that is unbearably flawed because of a bug you introduced, you need to hang your shame at the front door. Be equanimitous.
A member of your team is delivering good work. But they have personal traits that are abhorrable. Replacing them go would be hard. You must need to be equanimitous.
Feedback is delivered in less-than-constructive language. Take a deep breath and put the equanimity hat on.
Your job is to estimate specs so that your co-founders can decide what to build next. Resources are limited, but you strongly prefer one ticket over another. Equanimity up.
Long hours wear on you. Resources are thin. You’re at war, your team is your army, and you’re in a trench. Sometimes, it’s not easy to keep your cool. But it is essential . Or, as Spock would say, “You must learn to govern your passions or they will be your undoing.”.
Note: Any information of proprietary value to my employer has been removed or approved, and this post has been approved by my employer.
As we grow our business, I’m finding than the type of people that are worth my time follow this maxim, whether consciously or unconsciously.
Think about the traits of someone who creates more value than they capture..
charisma (social value)
intellect (informational value)
humility (social value)
generosity (societal value)
leadership (societal value)
abundance (monetary & otherwise)
as opposed to someone that doesn’t.
neediness (social non-value)
sloth (monetary non-value)
cheapness (monetary non-value)
envy (emotional non-value)
greed (emotional non-value)
Reads like a list of universally attractive / unattractive traits of human nature.
Take a look at businesses that create more value than they capture..
search engines
social networks
NGOs
doctors
retail stores
as opposed to ones that doesn’t.
cable companies
banks companies
insurance companies
Reads like a list of industries that are ripe for disruption huh?
I think that attraction to value must be something that’s deeply evolved into the psychology of all social animals.
After reading Steve Job’s biography this past week, I was struck at how much time he spent adding value to his products. According to the book, his successor, John Sculley, was more interested in attempting to milk profits from Apple’s products than Steve. When Steve came back in the late 90s, the turnaround was tremendous. Great product = value to the user = success.
