Reflecting on my first startup job: Part 3 - Lessons Learned

19 August 2014

(This is part three of my series reflecting on my first startup job. The first post was about surprises, and the second post was about regrets.)

Part 3: What I learned about the startup world (aka important lessons if I ever start my own company)

When I joined the company, it was already on the path to becoming profitable, so I missed a lot of the early, super-scrappy times. However, I still managed to learn a lot about how the startup world works. Here are some of the stronger lessons I learned, which will definitely be helpful if I ever began my own company.

The lean startup philosophy will save you time.

The lean startup philosophy emphasizes building out minimum viable products (MVPs) and testing these with real users as quickly as possible. It's meant to save time by providing real market feedback about your idea as quickly as possible, so that you don't waste lots of time building out a product that's ultimately not needed. There are lots of different, creative ways you can be scrappy in building out an MVP (a lot of them involve a low-tech or manual solution). I've talked about the pros and cons of this philosophy before, but I now agree, after countless hours saved not chasing ideas that proved unpopular with users, that it is definitely the right philosophy to have.

There is a difficult line to walk between quantitative and qualitative analysis.

In the previous post I mentioned how I wish that our company focused more on gathering and using qualitative user feedback. First off, I now appreciate that gathering either quantitative or qualitative feedback is hard. For quantitative data, you need to figure out which metrics are the right ones to focus on (keeping in mind that your choice will impact your actions), and then set up your systems to log the appropriate data. For qualitative feedback, you probably need to have somebody experienced in UX focusing a decent amount of their time on this one topic. And once you have the information, you have to figure out how to weigh all the data you're getting against each other. At some point, you will probably have to answer the question "This test shows that this feature improves core revenue metric X by 10%, but more users are emailing us saying they hate it. What do we do?". That is a very difficult question to answer.

People are super, super important to a startup (duh, but still).

During my almost-two years at this company, I saw a good number of people come or go. I think there are a lot of best practices around hiring, firing, and management processes that we were still trying to figure out, but overall the group of people I worked with made me appreciate how important finding good talent is to a startup's survival. You could always tell when a great new hire ramped up, because previously-backlogged projects would magically get done, and new, helpful best practices were introduced. Unfortunately, that also meant that when a strong coworker left, you could feel the sudden increased strain on the company's resources. Startups need a curious kind of employee, with some mix of skill, initiative, drive, and a critical eye, but when you find someone fitting the mold, you know it.

(Corollary) Morale is also super, super important to a startup.

If people are very important to a startup, so too is how those people feel about the company. When things are going well and employees feel great, there's a certain level of energy and excitement in the air, and people are not just happy to be at work, they're excited to be there. But when things aren't at their peak, either because of a surprise event (e.g. a firing) or a subtler change (e.g. a change in project management), then you can feel things starting to slip. Perhaps it's that people are quieter, or less productive, or willing to take more time off, but you can definitely feel the change in the air. Keeping great employees happy and engaged is just as challenging as finding them in the first place.

Partnerships and/or revenue can come from surprising places.

We spent a lot of time trying to increase certain metrics. These were usually ones in the engagement funnel for our product, so we would run tests on ideas to improve email open rates, click rates, conversion rates, etc. Improving any step of the funnel would lead to an incremental improvement in the ultimate goal: revenue. But, what would often have a disproportionate impact on revenue would be events like new partnerships, new revenue streams, or new content from our affiliate sources. In other words, many of the most impactful changes that helped us came from "outside" our company. Product work was important, yes, but from a revenue standpoint keeping an eye out for these kinds of surprising outside opportunities (or proactively creating them) can be even more valuable.

Communicating with parties in all directions is a skill that needs to be developed.

There are lots of parties that a startup has to deal with - users, employees, partners, and investors, just to name a few. Each has different motives, and wants to hear about different kinds of updates. Learning how to communicate with each type of party in the most effective way possible is a skill that requires some practice. A bit of preparation and thinking goes a long way. Before a conversation begins, you can think about what to communicate, what to not communicate, how a specific party will interpret a given statement, and how the conversation might proceed. Each type of party also needs to be updated at different frequencies and through different means of communication.

There's no one path to success in the startup world.

One great perk we had at this startup was that our cofounders would often invite in speakers from the startup world. These speakers would share stories about their own startups and the lessons they learned. What was surprising was that every story was incredibly different from those before it. Ranging from the bootstrapped startup with a tool that the team originally used for themselves, to a VC-backed startup that had already pivoted, each story presented fairly different lessons on how to start and run a company. It's heartening to know that starting a company is more about solving a problem with a solution you believe in and making that solution work, as opposed to following a set of norms set by the industry or investors.

Next and last in the series: what I'll be looking for in a future startup or tech job.

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