I was chatting with a friend the other night at our holiday party. She said she’d been hearing more and more young people idolizing startups. It seemed everyone she was talking to was going to start their own company or join a startup. She lamented that many of them had no idea what a startup was, or what their (venture-backed) business would do. This got me thinking…if someone had sat me down a few years ago and told me I’d be working at a “startup”, would I have had any idea what that meant?

When I was working on the draft for this post, I came across a post by the same title (“What is a Startup?” by Daniel Tenner: http://swombat.com/2011/12/17/what-is-a-startup). I recommend checking it out – it’s excellent analysis on defining a “startup”. His definition is really well-thought out and inclusive:

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.

The “investment experts” hate on Tesla Motors quite frequently. Every quarter since the stock launched, I’ve read the death knell articles. “Here comes the slide,” they normally say.  Here is one of my recent favorites: Buy The Car, Avoid The Stock. I feel like Paul Graham’s oldie but goodie applies here: Return of the Mac.

I have remained steadfast in my support (purchased a decent amount of stock just after the lockout period ended). I originally wrote a far more detailed post to explain my feelings, but after this recent stock market insanity, things need to be boiled down (the numbers don’t really make a lot of sense right now).  In any case, here is my investment philosophy here:

First, I’m investing from a long-term perspective. Most of these investment experts are coming at it from a more short-term view (here was one of my favorites: “buy the car, sell the stock”. As a long-termer, that has me excited to buy!). I’m not expecting to make money quickly, but I think over the long-haul my returns will be superior to holding Ford or GM.

We will continue to demand vehicles for a long time. Sooner or later, we must fully abandon fossil fuel-powered cars. Tesla is one of the few that is actually built for “the new way” (see, didn’t expect any “Wet Hot American Summer” references when you started reading, did you).

I take the Warren Buffet approach and imagine that I have the opportunity to buy the whole company. So I call them all into my office (I have an office in this scenario).  A few of them have deeper pockets, but are only willing to sink a small percentage of their total worth into this electric car future. These companies have grown fairly complacent, fairly lazy, and fairly distanced from the end consumer. Then imagine a young, whip-smart and driven Tesla motors striding into my office. Yes, they are flying by the seat of their pants, but they are going for it all the way. And this isn’t their first rodeo, either. They’ve demonstrated perserverance and the ability to generate traction too. Who are you going to invest in?

Note: I am not an investment professional, nor do I pretend to be one in this blog. I certainly haven’t sunk a huge percentage of my net worth into Tesla, and I’m not recommending anyone else to, either. But if you’re willing to put make one risky investment in your portfolio, Tesla is my bet.

We’ve mailed out a lot of shirts over the past few weeks – well over a hundred now, in all shapes and colors.  It involved a lot of carefully printed shipping labels, trips back and forth to the Post Office, and a lot of t-shirt folding.  It’s been incredible to read the tweets and see the photos that stream in of smiling people wearing Wistia shirts.  I’ve started a rolling set of them on our Flickr page.  We also did a blog post to show where all the shirts ended up.

Most people, after hearing that story, ask me if all the money we spent on the t-shirts was really necessary.  After all, when we could have gone with the standard cotton issue, we instead chose premium American Apparel t’s from the amazing Uberprints.  To answer their question, I refer them to a great post by Alexis Ohanian from Hipmunk that stuck with me.  In the post, he described the competitive advantage companies can get from doing things way beyond the “just enough”.  He says, “if you’re ever feeling like you’re doing something a normal person wouldn’t bother doing, you’re on to something.”  Sending out these t-shirts accomplishes so much more than just “sending out swag”.  It allows us to tell our customers how much we appreciate them, how hard we will work to help them achieve success in their endeavors.  

Sending out t-shirts isn’t just a side activity we passively work on – it’s a serious part of our marketing strategy.  And what is marketing: it’s attempting to get in front of potential customers at the best time and with the most relevant message for them.  Connecting with your paying customers is a practice that is well-documented.  Read any blog from a startup marketing sensei and you are guaranteed to get loads of better advice than I can give.  But sending out the t-shirts also gives us the chance to connect with a segment of people I think stable startups neglect far too often: the knowledgeable user who is not a potential customer.

We recognize that some people we come in contact with are just not a good fit, and we think there is some value in telling them that up front, before they have spent a dime with us.  With most companies, that’s it – if you are deemed a poor fit as a customer you will never hear from them again.  You’re a bad lead because you won’t convert.  To us, that isn’t so, and that’s why we’d like you to have a t-shirt.  

Today, I sent out two more shirts to a couple guys we met at a bar last week.  They aren’t Wistia customers, nor is it very likely that they will become customers in the future.  But they are smart guys who are now Wistia fans, and I would argue that in the long-run, that sort of “social karma” can be just as important.

http://www.flickr.com/apps/slideshow/show.swf?v=71649

http://embed.wistia.com/flash/embed_player_v1.1.swf

The other day I did something I haven’t done much of in my life. In fact, I could probably count on both hands the instances in which this has happened. Sure, I’ve thought about it, even imagined what it would be like, but I’d hardly ever followed through. I might have even been a little nervous, to be honest.

I bought an app.

Sure, I’ve bought some iPhone apps – those $0.99 deals that I hardly even think about. But never more than maybe $10 at a time.  So when I dropped $50 on Pixelmator and Sparrow, it was a pretty major event.  Having spent my entire computing history trying to avoid paying fees, I thought it’s worth mentioning.  I remember spending hours in the late 90′s learning C++ in the hopes of evading the ‘registration requirements’ of some of my early computer games. I may have even experienced some pirated software (a high school kid with a valet gig cannot afford anything Adobe puts out…I’m just saying). But I’ve almost never really bought anything.  So why the change? And more than that – why do I feel so good about it?

It’s not because I’m making more dough, and it’s definitely not because I’m more mature (no way!).  I think it’s because now I know what apps are going to provide me value.  Having a good idea what I’m going to get from a full-version of the product is a huge step to getting me to buy.

A few key changes have made this possible:

first, Google search made all sorts of content findable. Anytime I think about purchasing something, I always Google it to see if there are any reviews out there. Quora is doing this as well – lots of comparison topics out there.  You can be sure that before a customer drops dough on your product, they are searching to see how everyone feels about it.

second, the Apple “store” format brought reviews to software. This goes for both the iTunes store and the Mac App store. Before these were in place, buying software was a relatively closed-box experience. Today, there are hundreds of reviews for any popular app – if I don’t see any reviews, I run the other way.

third, Google made “freemium” products real. Because Google product’s revenue impact has nothing to do with purchasing licenses and everything to do with how you use the product, they could put a reasonable amount of resources into developing ‘free’ software. If a paid app couldn’t beat their free offerings, they were eventually killed in the market. In my mind, this pushed development teams forward, and made resources (read: talent and investment capital) more available for the teams hell-bent on creating a valuable piece of software.

This became more clear to me in a recent demo I was giving a friend on web analytics tools.  His employer has been using google analytics, and he was wondering if there was more out there for him to look at.  While I was showing off the good stuff Performable can do, and how we us Clicky at Wistia, it dawned on me – if these apps couldn’t beat Google Analytics, they’d be dead.  The pressure of a ‘free’ competitor is pushing their development forward in a positive way.

There are other reasons too – as development costs and time come down, it becomes possible to iterate on an app quickly to reward customers. Marco Arment, creator of Instapaper, has done a great job delivering additional value through product updates. Sure, he knew charging was going to eliminate some percentage of the potential pool of customers, but those customers that have paid have been rewarded with a simple product that does some amazing things.

A blog post by David Humphrey entitled, “Dear Twitter” highlights this behavior change quite well. He’s tired of Twitter’s buggy interface and slow speeds – and he’s willing to pay to get better service. He recognizes the value Twitter brings to his business and his personal brand…he just wants it to work better.  We can collectively vote with our wallets much easier and share ratings much faster (thanks to the iStores). We can also build products that are better than the free apps we can’t stand (like Feedly rather than RSS reader).

So where does this lead us? While it’s too soon to say for certain, I can say in my own world our subscription fees are allowing us to spend time building features to delight our customers. In my daily life, apps are also making it easier to access and digest information, accomplish tasks, and communicate with others. I get genuinely excited when I see upgrades available on the App Store, because I know it means a slew of improvements on top of a product for no additional costs to me. In short – life is good, even if I’m a bit lighter in my digital wallet.

take the MBA “road less traveled”.  Many of my classmates are now competing for jobs at terrific investment banks and mutual funds, and I wish them all the best, but I’ve learned during my short career that the big business path isn’t for me.  I wanted to work at a startup, where the risk was real, the people hungry, and the learning constant.  I had no idea how I was going to do it, but I was convinced I could make my ambition a reality.

Today is my eighth day as the official Director of Customer Happiness at Wistia, a professional video hosting and distribution platform.  I get paid a salary that I am happy with, I love the job, and the team is amazing.  I can say that I’m excited to get out of bed every morning.  When I solve problems for our customers, I create value for Wistia, and the knowledge I’ve been able to add to the company has already made a real impact.  But I’ll have more time to talk about the details of my job in a later post – this is a story about how I accomplished the first step of my dream; today, I work at a startup.  Now it’s time for me to share how I made that happen.

To Get Started, Make it Public:

In my mind, there was a clear moment when I started down the startup path.  That moment was when I hit the “post” button on “My Life’s Work”.  I had dabbled in pursuing a job at a startup in the past and was already an avid reader of sites like Hacker News, TechCrunch, Venture Beat, Bostinnovation, etc., but now I was fully committed. Once I publicly announced my desire to work at a startup, I knew I couldn’t go back.  l simply couldn’t end up with t  The typical “MBA factory” job burns through newly minted grads and assigns tasks that are sometimes menial at best. Now, if my (meager) blog following found out I had joined the masses at a job like that, what type of role model would I be?  Looking back, this was my first lesson learned: Get your goal in writing.  Only then can it be measurable, and then you WILL be held accountable.

Hustle:

So, I dove headfirst into startups.  I spent all of my free time reading posts by entrepreneurs/investors/gods like Paul Graham, Dave McClure, and Steve Blank.  I connected (however briefly) with startup superstars like Jason Shen and Micah Baldwin.  I attended startup events. I listened to Jason Calacanis and Mark Suster constantly (favorite episodes: Mo Koyfman and Brad Feld). In school, I focused on excelling in areas that would get me in front of startup-connected people.  I presented to VCs as part of a business plan project and worked as an MBA mentor for an undergraduate startup competition.  It was a never ending and somewhat exhausting process, but entering the world of startups is similar to what people say about coding – to really learn, you need to drink from the fire hose (I’m currently trying to learn that on the fly as well – another post!). Lesson number two: First know your stuff, and then get active.  Really active.

Seize the Carp:

This is where things get interesting.  In early December, I was performing a harmless search when I came across Wistia.  Very cool product, I thought.  Good blog with a fun culture, I thought.  AMAZING job posting, I thought!  Although I was a long time from graduating and in the middle of the finals week from hell, I quickly replied to the posting through their website.  “Off into the great unknown,” I said to myself, thinking I would never hear back.  I was floored when I received a response from Chris Savage, co-founder of Wistia. Over the next three days, we scheduled a phone and in-person interview. Despite showing up at the office fraying at the edges after an all-nighter, I was excited to be there and open to doing whatever they wanted me to do. Looking back, this was key to my interview success. If you aren’t willing to jump in on any task, no matter how different from your background or expected paygrade, then you need to re-evaluate whether you are really interested in joining a startup. Furthermore, I strongly believe that if I had hesitated and not made time for that in-person interview right away, I wouldn’t be here today. Things move too fast at a startup, and here in Boston they have way too many talented applicants to wait for me. I had to strike when the iron was hot.  I found out later that Bostinnovation had recently named the position one of the hottest startup jobs in town, so I was up against even steeper odds than I thought. Lesson number three: Seize your opportunity and run like the wind with it.

Get Psyched:

Following my interview, there were several weeks of radio silence from the Wistia team as everyone departed for the holidays. Self doubt crept in, and I began to wonder if they had moved on. So I reached out, and I quickly got a response…they liked me, but needed to see more. So I made an unorthodox offer that may have changed my career forever: I offered to work out of the Wistia offices part-time while I completed my prior internship commitments. That is, I offered to trek an hour to Wistia every morning and work with no certainty of ever receiving a full-time offer. Let me be clear: everyone thought I was crazy. But to me, this was an easy decision to make – this was a strong team working on a great product in a cool environment. My skills, and even more so my personality, lined up perfectly with the job opportunity. And maybe most importantly, it was just a bit more than I could handle.  I am going to grow into this role and continue to be challenged for a long time (hopefully forever).  Over the next few weeks, I ground it out, working and learning and barely finding time to study or eat. But when you know what you’re doing is worth it, you find huge reserves of energy. Lesson number four: Be excited to make some sacrifices, as long as you love what you are doing. That’s right, be excited, not just willing.

I won’t bore you with all the details (in this particular post anyway), but the ending of the story is a happy one (but you already knew that). I was lucky enough to receive a full time job offer after three or four weeks of my pro-bono part-time work. My (hardly used) title is Director of Customer Happiness at Wistia, Inc. We work hard, drink beer, and play lots of ping-pong (seriously, come challenge me). My job comes with all the typical startup benefits: long commute, longer hours, and lower base pay than many of my colleagues at business school. But you know what? I haven’t stopped grinning since I got here.

many many thanks to Amanda for proof-reading this!