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Here's A Great Philosophy On How To Build A Startup

Aimee Groth

There are hundreds of new startups that launch each year, but most will fail. At the end of the day, it's all about execution, not the idea.

So far online dating site HowAboutWe is a success, raising $18.5 million to date and hitting nearly one million users since launching in April 2010.

Co-Founder Aaron Schildkrout says it has everything to do with the process: "Really talented people just don’t like to work inside broken processes. It feels dumb to them."

We recently sat down with Schildkrout at his company's Dumbo, Brooklyn headquarters, and he shared with us how he and co-founder Brian Schechter scaled up the dating site, attracted top talent, and managed its explosive growth. Here's what he told us:

Hitting the ground running

"For startups, at the very beginning it’s incredibly easy. Brian and I did everything together. We were also working 90 hours a week, but if you're not willing to do that, you shouldn't launch a startup. We made all the decisions jointly. We got to the point where there was too much work to make every decision together, so we laid out every function on a table and basically split them in half, defining our respective purviews. We basically ended up with an org chart where he was running marketing and sales and operations and I was running product. Some things remained co-owned by each of us, like finance and the high-level strategy function.

The company grew, and early on it was very easy to create a deep collaboration on projects. Then you hit a situation where you have 6 – 10 developers, and people with expertise in marketing, business development, community engagement and content, so you've got 20 people on individual tracks. You want them laser-focused on achieving goals specific to their work, but you want a cohesive brand vision, with unified standards across the tech team.

Now we have 43 people and multiple teams working on different product lines."

Going from idea to execution

"The most important artery in the organization is that which leads from idea to final product. It has many, many steps, and can be elegant, with a beautiful flow. More concretely, how do you come up with ideas, how do you go through the design process, and how do you use data to inform decisions about what to build and assess the effectiveness of what you build?

You want to build a process where the right people are involved in innovating and coming up with creative ideas so everyone can do their jobs well. Where nobody ever gets blocked, or says, “I can’t move forward on this because I need x data," is very central to this.

As a company leader you have to work diligently to avoid excessive siloing, and yet the more collaborative your environment is, the more complex your structures have to be. You fall into the trap of a long meeting, with too many stakeholders on decisions. There's tension that you’re always managing as a company leader between deep organic cross-functional collaboration, and on the other hand, focused, clear prioritization, deep expertise, and efficient use of time. Mediating between those two forces to achieve maximum innovation and maximum efficiency is a fun workplace design project.

From a development perspective, you often run across intense specialization where developer Jack becomes your search guy — a single point of expertise and potential failure. With our tech team, we use a combination of rotation and pair programming to ensure that we don't have any single point of failure in our knowledge base. It's a collaborative process so the best possible code is being written. We run our development team on two week sprints.

You build things around the idea that they’re generalists, and it’s a very attractive way of doing things early on when you want multi-purpose players. Then people move more toward specialization, and you make sure they don't fall into the traps of expertise and excessive siloing. It’s a fine balance, there are pros and cons to both. And it's not always true that a happy medium is good. It has its cons. Those kinds of choices are relative to the moment. As companies change, goals change, and you need something quite different."

Finding top talent

"As CEO you have a number of responsibilities, [including] making sure you have the right people. This comment is very specific to early stage startups. You can do most things on your own, but you become a facilitator of other people doing amazing work. Make sure your personal contributions are the overall vision and overall company management. The obvious things are that you want people who are relentlessly driven and smart. There are many kinds of smart. Being a great communicator as a developer is essential. Work is inevitably challenging, and it should be. It’s part of what makes it beautiful and fun. When people encounter challenges, their potential to be reflective, and their capacity for self-awareness, is huge. So is flexibility, thoughtfulness and honesty. You want good people and it matters."

Scaling and developing hierarchy

"We have a flat overall structure. There are three levels of hierarchy. The whole point of any structure is to get it so anybody can do great work. That needs to rise to the surface immediately.

One thing I’ve experienced is that the number of people who have come here from other places that had bad processes — ineffective, broken processes — is tremendous. Many people have come here because their companies had bad processes. They had massive inefficiency.

On the other hand, people from Goldman Sachs know how to work hard and efficiently. These people have great process thinking. For example, our head of business development and our VP of acquisition, retention and revenue are both from Goldman.

When I talk to people who work at top startups around the country right now, they’re really effective about process. Really talented people just don’t like to work inside broken processes. It feels dumb to them. Building a great process is very hard. Another topic that’s sort of interesting is building processes inside an explosively-growing company. Building processes in linear-growing or stagnantly-growing company is completely different.

How to get things done: that’s what’s always been the purpose of the workplace. How to build value. And it will continue to be the purpose of the workplace. The nature of value changes and the workplace changes accordingly. Smart people adapt and innovate and build a process that truly works. So it's thinking of business as a value-creating product itself."

Now Tour HowAboutWe's Cool Brooklyn Office >

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