Six Months In

2 09 2011

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As I sit down to write this, it has been nearly six months since my first official day as an employee at Wistia.  Holy shit.  Before I start this post, let me lay out the scenario.  It’s mostly dark in the office (9:30pm), with just individual lamps highlighting desks.  After a day of work, a few of us descended on the turf room, played ping-pong and some CoD, and then they mostly left.  Now, it’s just me and Ben, churning away on the keyboards, eating hummous and chips for dinner, while the “hip hop – all eras” turntable room keeps the beat.  This, friends, is the life in a startup that I’ve experienced.

If you’re like me, you’ve probably spent a lot of time pouring over “life at a startup” posts on hacker news or some similar source.  For me, I always wanted to know more about this world, and how to succeed in it.  Luckily, startup folks are pretty (heathily) obsessed with sharing lessons learned.  I’ve done my best to add to this on topics I am familiar with, like getting hired at a sweet company.

There’s been many many “what it’s like to work at a startup” posts, and I’ve read almost every one I can get my hands on.  I’m hoping some of you will voraciously read this the way I’ve read others in the past.  

But, even after reading all of those posts, I’ll admit I was still completely unprepared for life in this world.  No amount of reading will make you ready.  There is no silver bullet to being a great member of a startup.  There is no perfect answer to the question “should I stick with my steady job, or join a startup?” Sorry about bursting those bubbles.

Despite all of that, I’m going to try to share some lessons I’ve learned in my short time at Wistia. If you love what I’m talking about below – a startup might be for you.

1. There is no Typical Day – And That’s What I Love About it

A bunch of people have asked me, “can you describe your typical day?”. At first, I tried to actually mock out a schedule, but there isn’t anything really “typical” about my days. There is one word to describe it: ‘action’. As my favorite professor, Pete Wilson says, “Get up and get and get ready to rock”.  This is universally true, no matter what role you are in – you’ve just got to move forward every day.  Endless to-do lists and forced prioritization is the name of the game.  For some, it could be making a connection at that email marketing company that is an integration target.  For others, it’s getting emails and calls out to customers for their feedback.  It could also be researching a new way of structuring the database, to scale to hundreds of thousands of users.  If we don’t move the product and customer experience forward, eventually you get run over by the next crop of more driven folks.  Don’t make the same mistakes twice, and don’t sit on something that needs to be done. That’s the typical day at a high level.  As far as the details…I’ve tried new caffeinated beverages (I now know the ins-and-outs of making an iced Americano), I’ve interacted with high-up folks at many large companies, and the few meetings I’ve had are the most productive I’ve ever experienced.  Other than that…every day is a totally new experience.

2. The Team Really Is What Matters Most

I was speaking with some grad students lately and one asked me, “how do you deal with the solitary experience of being an entrepreneur?”.  This was a bit flattering.  First of all, I’m no entrepreneur.  Brendan and Chris (and Adam and Ben and Jim) built this company long before I came along and started making a mess in the sandbox.  Compared to their experience, mine is one of blissful stability.  But I think I speak for them when I say that doing it alone would be no fun.  Sometimes, you might wish it was a solitary experience – startup employees are a bunch of type-A folks who will have an intense need to get their paws into every part of the business.  This is unavoidable.  It’s just what happens when you get a bunch of passionate and extremely intelligent individuals together and then actually give them a say in the future of the business. This was really hard for me at first – I found I had a pretty strong urge to ‘own’ my work (probably from my business school experience), and almost felt insulted when others stepped in.  This coming from a guy that would have said “works well in a team” was one of his key strengths.  I’ve learned to deal with this better over time.  While individually we each have our responsibilities and larger stuff that we cannot “drop”, we share the common experience of building an excellent product that just works for our customers.  So while we might get in each other’s face from time to time, it’s mostly because we don’t have time for bullshit and our customers deserve the best. There’s no team I’d rather be working with.

3. Attitude Wins Championships

You know the old saying, “just show up”? Totally true. Show up every day, ready to rock. Attitude is what helps you put serious effort into what you’re working on.  Attitude is what helps you respond the way you should when another team member disagrees with your opinion.  Attitude is what gives you the motivation to tackle that daunting project after others head home.  It’s also great to be around people with a great attitude and work ethic.  When folks come to the table ready to accept other opinions and inputs, the discussion goes so much better and more productive.  You’re going to be spending a lot of time with these guys in close quarters and in many situations.  Enjoying that time makes it easier to celebrate the wins and console each other on the losses (and there will be both). Remember when you are interviewing – attitude.  It’s that important.

4. Learnings => Evolving => Winning

Learning is made super important again at a startup. Simply put (and sorry if it seems callous) if you don’t learn, you’re unemployed.  Learning leads to breakthroughs ahead of the data.  Don’t get me wrong – data is still incredibly important to us – it drives most of our decisions. But there are way too many times when you have incomplete (or no) data on hand, and you simply need to make a move.  Learning leads to superior ‘intuition’, which is even better.  Learning is what makes the team faster, stronger, better.  It’s what puts you ahead of the slower, dumber competitors, even if they’ve got deep pockets. It is what lets you anticipate market demands and movements long before they show up in the data. What do I mean by learning?  Talking to customers, checking out the newest analytics software, spending a few hours playing around with a new javascript static asset controller (that’s for you, Max), getting on the phone with a genius in an area your team is weak in to get their thoughts – just learn something new and apply it.

5. What to Look For When Hiring? Curiosity.

Since I came on as sort of the beginning of a growth wave at Wistia, I’ve been able to participate in a fair amount of interviewing of candidates since then.  At first, I had no idea what I was looking for – just tried to ask some questions that were tough enough to see how folks would handle pressure.  But as I’ve gotten a bit more practice, I’ve learned to split the task into two separate (and equally important) parts.  The first part is the evaluation of intelligence and base knowledge related to their singular ‘responsibility’.  For marketing-focused people, it’s their ability to get their head around dicing analytics and getting some potential hypotheses (as an example).  Essentially, can they get the shit that they need to do done, and will they kill it in the process. The second part of the interview is around our ability to work together and their natural curiosity.  We chat about what interests them, what they might do on their first day, and then we do something like play Call of Duty.  The curious folks follow the same plotline – “I need/want to know what everyone is doing and how they do it…then I would probably start re-arranging my little piece of data to better feed those jobs”.  That means better arranging marketing performance data so that Joe can see which of his designs panned out best.  It might mean further distilling customer responses and helping the rest of the team prioritizing them.  Hell it might mean settings up a t-shirt shipping station.  Their brains need to understand how the whole thing works – and then they attack inefficiencies and question the status quo.

Curiosity is the asset that everyone I’ve ever met that worked well in a startup has.  I think that is what drives them to start/join one in the first place.  To some, it might appear like nerdiness – for example why almost all of us run MacVim off the same vimRC file – but it’s really just intensely wanting to see what happens with each experiment.  You see, curiosity is what leads us to tackle a new feature, even when we don’t know exactly how to build it.  We can’t help ourselves.  Curiosity is why marketing meetings at Wistia are attended by 100% of employees – everyone wants to see how we’re performing and try to tease out some of the reasons why.  I don’t know if you can just ‘get’ curious – I’m pretty sure it’s mostly built in – but I guess if you made it to this part of my rambling blog post, you’re probably the curious type (or my mother).

Six months is, in some ways, a lifetime at a small company.  We’ve released a ton of improvements to the product and tried a lot of different marketing and branding tactics since I’ve been around.  But in other ways, it’s such a small chunk of time.  I still know essentially nothing about helping to manage the team dynamic or grow and nurture the culture.  I still leave feeling like I’m not contributing enough most days.  But the amazing thing is, I’m still so pumped to wake up every morning. That is the most rewarding feeling of them all.

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