A number of people expressed surprise at my choice to work with a data science startup instead of some of my other options. I admit I would be surprised too if you told me three months ago. So I want to document my rationale (sprinkled with premortem notes e.g. worse-case-scenarios), to see how good my reasoning turns out to be a year from now.

The Lens

There were roughly five different lens I evaluated my options through. They were:

• Meaningfulness (or Do-gooder-ness)
• Kind and Gracious People
• Risk and Upside
• Scariness (or oh-shit-will-I-make-it)
• Realness

Meaningfulness

Meaningfulness in my mind is the question, “will my work benefit the less privileged members of society?” It stems from a haunting awareness of my incredible and underserved privilege in society. There were a number of do-gooder options i.e. going to work for non-profits. The clear leader of the pack here was IDEO.org. It was clear from their mandate that they were working very directly on alleviating poverty and lifting up the developing world through design. There were other places i.e. education startups where I felt their mandate was clearly good for a large number of people in the world.

Of the five lens, this is the one through which Sift Science makes the least sense. I will freely admit I still have trouble reconciling this one, except to commit to working on non-profit work in my spare hours. As a premortem note, if I am unhappy at Sift in a year’s time, my prediction is that difficulty reconciling my day-to-day work with societal meaning will be a big part of it.

Kind and Gracious People

When I reflect upon what made graduate school so pleasurable, I found it was always the kindness and graciousness of the people I was working with everyday. I wanted to find an environment where I believe the people will be as awesome as my mentors and classmates. 

This is very much a gut judgement. I was lucky that quite a few of the places had people who seemed kind and gracious, but Sift was among the best of them. Every person on the team I interacted with (and I interacted with quite a few of them) came off as sincere and earnest. They ask interesting questions, and were open and enthusiastic to unexpected questions of mine. Indeed, I doubt I am wrong about this one.

Risk and Upside

Having read Antifragile recently, I have been asking myself, “Am I taking the right kind of risks?” It’s kind of an obvious idea that one should take bets with small downsides and big upsides. The antifragile idea is to look for upsides with unpredictable/combinatorial upper limits. This is where a lot of the bigger corporations I spoke to started looking less interesting. Big corporations are places where the downsides are minimal, but upsides are quite predictable, and capped.

In my mind, this is where Sift Science felt really promising. Sift Science sit at the intersection of two macrolevel trends in the world. One is the rise of applied data science, and two is the rise of online commerce. Sift, or something like it, will create a ton of value, and Sift being a YC and USV company gives me a lot of confidence that this is a good bet. I am taking a bit more of a risk than if I were to go to a bigger corporation, but, really, just coming out of school it is a small enough bet that I can afford.

What’s the premortem here? We find out Sift is too early in bringing data science fraud detection to the mass market, I learn a bunch of things, and take another job somewhere else in the YC or USV network. Really can’t go wrong here.

Scariness

Related to the idea of risk is the feeling of subjective scariness. How afraid am I of taking on a particular set of responsibilities? (e.g. how often do I feel like “Oh shit oh shit will I live up to their expectations of me?”) There were a number of options that didn’t scare me at all, which to me means I likely won’t be stretched as much as I ought to be. Whereas at Sift (and some of the other startups I considered) I felt a bit more nervous. Will I really be able to advocate for good design in a startup environment where I am the only designer? Will I be able to make design sensitivity and language a part of the organization’s culture? I felt like I have a very real, non-zero chance of failure, and the thought was invigorating.

Premortem: That I cannot adequately articulate the value of design to an engineering-centric company, end up being a front-end design implementer, and don’t bring a lot of value to the team. This would be the nightmare scenario, and will teach me that I am a poor judge of company culture. Fortunately, if this is the case I suspect I will know rather quickly, and can go beg for a job elsewhere.

Realness

Realness has been my short hand for the combination of these three questions:

• Am I making something real that people can use in the near term?
• Is there a way for me to frequently measure/understand whether my design was effective? (i.e. real feedback)
• Is there an opportunity to iterate based on that feedback in a focused and in depth manner?

I understand this is a luxury. There are lots of worthy projects out there where this kind of short feedback loop is not possible. Nonetheless I felt that inorder to develop a better intuition for how people respond to interaction design, I want to live in a rapid and sustained feedback loop. I want to be exposed to real constraints, e.g. user whims, limited time, and limited money. Albert at USV put it succinctly when he said, “I think you will learn a lot from (dealing with) market discipline.”

Sift has a functioning product with a strong value proposition, and some customers who undertand that proposition. It’s also evident to me that interaction design and data visualization will substantially affect the effectiveness of the product. The circumstances are ripe for doing this kind of in depth product design iteration that I’ve been itching to do. This is frankly what I am most excited about.

Premortem: I suspect of the five lens this might be the one that I am overweighing the most. At graduate school I was perfectly happy working on theoretical projects. I was also perfectly happy hopping from project to project without diving really deep. It may turn out that in 18 months I will be sick of working on the same problem all the time, and long for the variety that comes from a consultancy like IDEO.org.

Probably Overthinking It

All these were the overwought thoughts of the rational mind. Ultimately, I had to ask myself, in my gut which options did I feel good about? At the end of alcohol infused evenings, when the rational mind loosens its grip, I noticed I was most excited to talk about Sift Science and IDEO.org - and those were my final two contenders.

The final tie-breaker was the idea of optionality. Would it be easier to leave Sift Science to go work at a place like IDEO.org? Or to go from IDEO.org to find a fit like Sift Science. It certainly seemed like a promising, early stage startup like Sift would be harder to find, so the choice became Sift Science.

That’s the rationale. I am really quite excited to see how it plays out.