Staying Motivated

The question is not how far. The question is, do you possess the constitution, the depth of faith, to go as far as is needed? – Boondock Saints

As I think about the primary success factors in the first year of Contactually, and how it differs from previous ventures I’ve undertaken, been a part of, or witnessed as a third party, staying motivated is one of the most crucial factors. Given that your new venture is, by default, a failure, having the mental strength to keep the fire going not only in your heart, but in your team, is an incredible challenge.

Statistically, you’re going to crash and burn. Why get out of bed this morning?

In some of my past ventures, the moment I hit any serious doubt (competition, marketing issues, technical challenges), I could almost watch in the mirror as the passion for my idea slowly faded away, to be replaced by something else in my notebook of ideas. With the help of a team, good customer development, and sheer velocity, I was able to push beyond the “wantrepreneur” stage (Note: maybe I’m a bit too hard calling my past self a wantrepreneur – someone who talks about an idea rather than executing it. But there is a tangible difference between trying out different ideas and prototypes, and throwing every waking minute you have into your vision, which is what I do now).

However, the early hurdles are only replaced by bigger hurdles. Clawing to improve every metric, focusing on the vision, getting rejected by investors, users deactivating, negative feedback, and, in general, failing constantly. Now, on a macro level, Contactually is flying – everything “up and to the right” – the primary mantra pounded into my head at 500 Startups. But on a day-to-day level, showing up every morning, and just grinding ahead, is a psychological feat.

Now I’ve learned that there are many things available to me to help with that. As they should in anything in life, your family, especially your significant other, plays a major role in keeping you motivated, just as you should do for them. Your local community of like-minded entrepreneurs should be there for you too – the value of sitting down for lunch with someone, spilling your guts, and being told “yeah, I’ve been there too” is powerful.

As a web entrepreneur, there are a few specific things that I’ve found are a great way to keep the wind in your sails.

Celebrate every win – As we’re a SaaS business, the biggest driver is when someone upgrades and starts paying. We have our web application post a celebratory message every time someone upgrades into our team chat room, which every co-founder, employee, contractor, and intern keeps open all day. There’s always a quick (~5 second) interruption while everyone cheers or posts a funny avatar or animated GIF. No matter what’s going on at that time, it’s a moment of pure joy.

Keep user stories around – We’re fortunate to have a growing strong base of dedicated professionals using Contactually, and deriving serious value out of it. We’ve set up a process to interview and write up a one-pager, talking about how valuable Contactually is for them. I keep them around and read them regularly. Oh yeah, and these Case Studies also happen to be EXCELLENT fodder for sales and marketing.

Review monthly progress – As a venture backed company, it’s strongly recommended, if not required, to regularly update your investors. This takes the form of a rather long email, reviewing growth in KPIs and other metrics, press coverage, and other team/product news. I started out writing these mainly for my current and potential investors, but the value has extended far beyond. Those monthly updates serve both as a way for you to take a step back and review monthly progress, but a moment in time that you can come back to later. I often find myself re-reading these.

What works for you?