In praise of constraints in building a startup



Building a startup is daunting, an exercise in organization, prioritization, and execution. An endless number of tasks calls for a founder’s attention, none of which can be derived from a cookie-cutter blueprint. Believe me, I’ve looked.

So, how do my co-founder Paul and I work through the significant tasks that jump to the top of our Treatings to-do list? I’m talking about the vital items, those even more important than getting organic cotton t-shirts embroidered with our ever-changing logo and launching ice-cold emails asking Nick Bilton to write about us. (I don’t care what anyone says. “Hatching Treatings” is a concept for a story, opening with Paul and me in the middle of a high-stakes power struggle: whose turn it is to sleep in the top bunk.)

Our tool of choice in figuring out how the hell we’re supposed to build a startup: constraints.

Like any green entrepreneur, when I quit my investment banking job to start Treatings I wanted the product to have the broadest appeal. I figured, who wouldn’t benefit from a professional networking platform that facilitates one-on-one meetups over coffee? Instead of making the mistake of limiting ourselves to one demographic, let’s welcome everyone.

I’ll wait for the grizzled startup veteran’s eyes to complete their 360 degree roll.

We’ve learned that constraints play an integral role in building a startup, from defining the community, designing the user experience to determining an appropriate workplace culture. We’re still searching for the appropriate balance of imposing constraints without being oppressive, but here are some things we’ve learned.

Community definition

When we started, I agonized over every website copy change, fearing we’d alienate a potential user base. Paul and I have had countless conversations around whether we should explicitly say that Treatings is a networking platform for “young” professionals.

We’ve found that before defining what our community is, we need to be unequivocal about what it isn’t. We facilitate professional interactions; we aren’t a dating site. The goal is to facilitate mutually beneficial peer-to-peer conversations; we aren’t an expert network. The goal is for conversations to be taken offline; we aren’t a messaging app. Each artificial constraint reduces our market, which is actually good. It gets us closer to having a definable group of users.

Marketing to a specific demographic is the first challenge. Getting our target market to engage with the platform comes next. We need to overtly define our community’s reason for existence for the same reason dating sites need to. To propose a date with a stranger, you need to have comfort that everyone on the site is open to meeting new people.

I don’t think anyone would send a message to a stranger on Facebook saying “How about we put my archery license to good use and head over to an archery range.” That would be reason to alert the authorities. But that’s a real date proposal on the dating site How About We. It’s all about context.

If you’re going to reach out to a stranger, whether to ask them on a date or ask about their work, you want to know that everyone has opted into the platform for this singular purpose.

User Experience Design

I’m not an accomplished UX designer, which is why I’ve had to learn a lot of lessons the hard way. I was surprised to find that the more structured we made our framework, imposing artificial boundaries, the more engagement we saw.

In “The Design of Everyday Things,” author Donald Norman writes that when designing a product, “constraints are powerful clues, limiting the set of possible actions. The thoughtful use of constraints in design lets people readily determine the proper course of action, even in a novel situation.”

There’s uncertainty involved in asking a stranger out for coffee. In order to feel comfortable proposing a meeting on Treatings, individuals need to know that fellow members are expecting such requests. In the past we’ve considered lessening our emphasis on in-person meetings and just being the best way to contact professionals outside your network. In speaking with members, we found this would diminish their likelihood to engage since there would be less clarity on why fellow members were on the platform.

After making it clear that everyone in the community is open to meeting, we must provide social proof that others are utilizing the platform. This an area where online alumni networks fall down. While most alumni directories have a healthy supply of individuals open to sharing their insights, they are essentially static directories, which isn’t a good environment to spark conversation.

There is a danger of imposing too many constraints. In past iterations we mandated that when reaching out to someone for the first time you had to propose a place/time to meet. We reasoned that if we made it clear that these were the rules by which everyone abided then people would overcome their anxiety from appearing too forward. We found this was too restrictive and stopped some users from sending introductory messages.

Workplace Culture

I’m not an authority on creating an awesome workplace environment, given we’re a bootstrapped team of two. Our biggest focus is on not adopting the “culture” of our work environment, New York University’s Bobst Library, which is essentially a dormitory for stressed out students.

I do have first-hand experience on how not to create a healthy culture. In my prior job in finance there were way too many constraints: artificial deadlines passed down the ranks with little notice or reason, deliverables had to be done within the confines of pre-approved templates and face time was celebrated.

In the startup community, I have observed an appropriate balance between creating constraints and giving employees the flexibility to operate within them. The happiest employees I’ve spoken with work in a structured environment where success is clearly defined and goals are set. But, they are given flexibility to operate within that framework, evaluated based on execution and performance above all else.

According to my “research,” people’s appreciation of constraints doesn’t apply to employer-provided free food, beer and house cleaning.

[Image Credit: John S. Quarterman on Flickr]