Costume Store or S & M shop

Vision Alignment in Early Stage Start-ups

Prior to joining General Catalyst, I did a few things, largely in the venture capital world at Insight & Accel. Most recently, however, I founded a mobile software company called Spontaneously. To an outsider, the simplest way of describing our ambition was to build a better mobile-first calendar. Over the course of a little less than two years, we went through our own twists & turns and ups & downs. Our company was born in the womb of TechStars NYC, in it’s second batch (summer 2011). Seven or Eight major product iterations later, we shut the company down. I’ve tried to crystallize my learnings across a number of dimensions from that tough period, and thought that I’d begin to share them here.

The focus of this post is on the importance of vision alignment among a founding team. People often say that starting a company is an irrational act. What’s even more peculiar about it, is that to do it successfully, you often need to combine that irrationality with incredible self-awareness. Why are you starting a company? Are you really the right person to start the company you are working on? And how confident are you that the people you’re working with are your occupational soulmates, cut out for the specific challenges at hand.

I had the pleasure of starting Spontaneously with a talented and passionate pair, brothers Josh and Dave Keay. Josh is a product designer, with training in graphics. Dave is a full stack engineer, with a focus on mobile. Prior to our company, they’d together built about two dozen iOS apps, several of which made it to the top 25 of the AppStore in its early days — talented guys. My background prior was in the venture capital world, working with companies from early stages on hiring, partnerships, capital raises, and broader strategic thinking. My role at Spontaneously was product management and operations.

The brothers were introduced to me via a mutual friend. The friend had heard that the brothers Keay were starting to build a mobile calendaring application, and were looking for a third leg to their stool who shared a passion for their space and could help them build a larger venture-backable company beyond the bootstrapped studio environment that they’d built successfully on their own.

My interest in calendars was deeply personal. When I got to college, I was miserable. Some how, I convinced myself that I did not belong. I worked in the library 16 hours a day, had no friends and no fun. My dad called me up one day and said the simplest of things that would stick with me forever: “this is your life.” When I complained to him about how I was eating junk, feeling alone, not taking care of my body, and in a taxing romantic relationship, he empowered me to make changes. But to do that, I needed to make time. And to make time, I needed to make manage my calendar more carefully, giving prominence to my priorities. So, I began to schedule everything, and made it my mission then to try to use technology to help me get more out of the time that I had.

My cofounders thought about things a bit differently. They considered the calendar as an inherently social tool that, with better visibility into a users’ availability and interests, could help its users see the people they care about more often — a noble and inherently more social motivation.
At the time, we looked at our differences in skills as an asset; little redundancy meant more productivity. We looked at our differences in vision as temporary and also as a source of strength. We felt that each one of us ultimately only answered to empirical arguments, that debate would push us to be better, and that we’d be able to persuade one another of the proper road ahead as each situation required. Ultimately, we’d end up with one true north.

What we wound up with, however, follows a metaphor which I’ve dubbed “S&M Store or Costume Shop?” If you stand on the corner of 11th & University in Greenwich Village in NYC and look East, you’ll see a massive window display with manicans bearing wild gothic outfits. One bystander might see a Halloween costume shop, where outlandish outfits are worn for comedy and entertainment, and another might see an S&M shop, where outfits are used for another form of entertainment. At the distance, the two look quite similar. But when you walk East on 11th Street, you quickly see one of two quite different realities.

Josh, Dave, and I did not bother to “walk East.” We were optimistic. And we were not self-aware. I wanted to use calendars to solve social coordination problems, but only as a pierce of a broader utility. Josh and Dave wanted to focus on the social, requiring deeper work from an early stage on things like social etiquette and content recommendations, which I was unprepared to wrangle with.

Neither of our visions were ‘right’, but they were different, and if I trace back the true source of many of our disagreements and set-backs as a team, I can attribute a great deal of frustration and likely our ultimate demise to this.

When I spend time with very early stage teams this time around as a VC, I look very differently at the notion of vision alignment. After all, being 95% on the same page as your cofounder(s), but thinking you are or will get to 100% will mean that you each could wind up at very different types of custom parties ☺