Building an Insanely Great Team
"Luck," she said, "lots of luck. And patience." I asked Sam, my girlfriend, for her thoughts on how we built our team. She's right - it definitely takes plenty of both.
There are also a few other important things: figuring out your weaknesses, thinking about the type of organization you want to build, and putting a process in place that allows you to find a broad number of potential candidates and screen them for the right set of skills and character.
It matters because there is little more fundamental to what you are as a startup than who you are. It's not the idea or the product or the brand or your bank account - those are all results of the people behind them.
Building a team that can execute on any idea can seem daunting to a solo founder with just an idea. Once you come to terms with the fact that you can't do it yourself, the process of figuring out what the right pieces are, and how you might possibly pull them together becomes your biggest challenge. This will become the crew you'll find your wave with, catch it and ride it, watch it come crashing down on your head, and then jump back on the board knowing that they've got your back and you've got theirs.
Who are you?
It begins with a deep self-examination, which often is caused by falling flat on your face over and over again. Why did your last project fail? What do you know about what you're trying to do and what will it take? And then you turn towards the mirror and ask a bunch of questions:
Can you code? Can you talk to customers? Can you build an audience? Can you do serious market research? Can you raise money? Can you recruit? Can you sell?
Now, many of us can do some of the above adequately, or can teach ourselves to get by on a couple of those. But keep in mind that any startup is built on the idea that you're going to achieve whatever you're aiming for with a fraction of the resources of any of your competitors - nowhere in that bargain is there room for anything adequate. So, which of all of those can you not do exceptionally well?
I knew I couldn't actually code, and we'd by now realized we didn't want to outsource key portions of our development. I enjoyed working with our customers and I could take on most of our fundraising efforts, and I'd done a good bit of market research and development. I thought the ideal founding team for us would then include an ex-journalist with an editorial appreciation for why a story's worth reading, and an engineer with an appreciation for how we could use data to identify stories worth reading and better match them to the people who need to read them.
Taking on a mission such as telling people what's worth reading - becoming a trusted product that helps them live their lives more effectively, that informs them, broadens their horizons, introduces new perspectives, new ideas - requires a certain worldview. I boiled it down to a few basic values that I looked for in anyone I considered as a potential partner:
Ask excellent questions: when you're starting a company, resumes and skills are just check boxes. Either they can or they can't. What makes all the difference is why you want to do this, and how you're curious about what we're doing. I quickly bonded with people who asked good questions about what we were doing, what was happening in journalism, what users were looking for, and in particular, why we were passionate about this specific thing right now.
Appreciate nuance: I deeply believe that there's very little in life that's black and white. It's rare that you're lucky enough to have a clear set of options on a decision, and the people who thrive in those situations are a better fit for a lead role in a startup. This requires an ability to break a situation down to its possibilities, quickly evaluate the options, and make the right call given the circumstances. You're rarely perfectly right, and you're rarely perfectly wrong, but in every case you have something to learn from what happened, and especially what didn't happen.
Look up at the world: I spent five months in the middle of 2010 on the road mostly by myself exploring much of North America because I wanted to know how the American energy industry worked. I learned a few things about energy, but I came to appreciate that the world is this massive, complicated place that's so much bigger than any of us will ever realize. I believe any organization that chooses to traffic in knowledge should appreciate that we'll never know or understand enough, and the only way to approach such a task is with humility.
Andy
Sam and I almost canceled on that evening at Healey's. We hadn't had much time together that week and a quiet night out sounded pretty good. But my dear high school friend Healey Cypher's tough to turn down, and we trekked over to his place in the Mission a few minutes late. Healey soon introduced me to a scruffy guy sitting on a stool in the kitchen, and said something like, "Deep - meet Andy, and tell him about what you're working on."
A few days later, Andy became our co-founder & Editor. We'd met a couple more times after initially having a good connection at Healey's, and we talked a few times on the phone. I went through in detail what I wanted to build (which was the initial plans for mycirQle at the time), and faced plenty of thorough cross-examination from a talented journalist. Though I had no doubts that Andy would be a skilled lead editor, I didn't expect that I'd come to trust and appreciate his judgment, thoughtfulness, and his desire to nail down the details before plowing ahead (I tend to just plow ahead and deal with the consequences).
The Process
I met Andy before I appreciated the process of recruiting.
When I was looking for the right co-founders (an Editor & a CTO), I came into it with a vague sense of the skills we were interested in, and slowly started to refine them as I met more people. I hadn't much of a clue of what a great editorial co-founder would've looked like. I had a pretty good sense right away that Andy's editorial values fit the type of organization I wanted to build, and that he was the type of person you can build an organization with, and I simply went for it.
On the other hand, finding the right CTO took us so long that by the end, we had a great process in place. We'd work our personal networks, mine certain job sites (mostly Whitetruffle), attend networking events (way too many), and have dozens of calls and meetings. Some people were clearly not ready to build a great product, some had a narrow skill set, others couldn't manage other people, and some we wouldn't have been able to work with. Through about 6 months of serious searching, we really liked only a couple of candidates, and things didn't work out with either.
But we'd learned a lot about what we were looking for: we wanted someone with a passion for data because we knew personalization and recommendation involved a heavy dose of it. We wanted someone who could communicate well, build a technical team, and someone who had an appreciation for news, for finding good stories and sharing them.
Tom
I walked into Grey Dog's that morning figuring there was no way he could live up to his resume. I was maybe a minute late, ordered a bagel and sat down. Within a couple of minutes, we realized he was sitting on the other side of the room. We sat down together and had a great chat. We clicked immediately, and he seemed to appreciate our vision for the product and the technical possibilities. The idea of starting a company and owning a product seemed to excite him, and we dove into the process as he'd lined up another major offer by then. Andy interviewed him that afternoon, after which the development team we were working with ran him through a series of questions. I sent him our deck & financial projections, and met him that night for what turned out to be a 3-hour meeting until 1am. Over the course of 15 hours that day, we'd spent roughly 8-9 of them with Tom.
Because we built a great process, we were able to immediately pull the trigger when we found an exceptional candidate. That was also the case when we found Nate, our Associate Editor, who we found through a fantastic recruiting process developed by our friends at HireArt, and Cara, our amazing Business Development Associate.
Who we are today
To my left sits Tom, our brilliant CTO whose energy and spirit buoy all of us when coffee isn't nearly enough. To my right is Cara, who takes tasks and devours them as diligently as I could've imagined, who's turned out to have a wonderful eye for design and details, and who has the most startup experience of the five of us - shocking when you realize she's still in college. Andy now sits across from me, in many ways a counterpoint to my weaknesses, especially my occasional tendency to put short-term survival over long-term development. Nate's with us from San Francisco, where his wit and vision and ability to put the team first has brought more life to our company than he'll ever take credit for. Among us, we've got a genius engineer with more social skills than many entire engineering teams combined, two thoughtful journalists with a real passion for finding and sharing great stories, and Cara, our Jane of all trades who shows up every day and just does everything asked of her really well. You could pair off any of us and we'd have a blast with each other and learn so much from each other.
And that leaves me, for whom the most that could be said is that I've brought together these exceptional people to work on one hell of a problem.
- Sandeep Ayyappan