How to Stay Motivated as an Entrepreneur

Editor’s Note: This blog post has been excerpted from an article that was originally published by Zvi Band on his blog. 

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 or observed, 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 in your heart – and 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, stagnant metrics, users deactivating, technical challenges, negative feedback), 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.

Now, I’ve learned that there are many things available to me to help avoid that:

Seek out friends and family. As with anything in life, your family (especially your significant other) plays a major role in keeping you motivated, just as you should do for them.

Connect with your local community. 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.

Celebrate every win. As we’re a SaaS business, the biggest driver is when someone upgrades and starts paying. Every time that happens, our web application posts a celebratory message into our team chat room, which every cofounder, 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 for them to interview and write up a one-pager, talking about how valuable Contactually is for them. I keep them around and read them regularly. Plus, case studies are excellent fodder for sales and marketing.

Review monthly progress. Venture-backed companies are strongly recommended, if not required, to regularly update investors. For us, 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. These monthly updates are not only a way to step back and review monthly progress, but also a moment in time to come back to later. I often find myself re-reading these.

What works for you?

Zvi Band is the CEO of DC-based Contactually, a CRM product that integrates directly into your email, backed by 500 Startups. He is heavily involved in the DC tech scene, including Proudly Made in DC and the DC Tech Meetup. You can follow him on Twitter @skeevis

Did you find this article helpful? Click on one of the following buttons
We're so happy you liked! Get more delivered to your inbox just like it.

We're sorry this article didn't help you today – we welcome feedback, so if there's any way you feel we could improve our content, please email us at

Written by:
Tech Cocktail is a literal "cocktail" of tech, startup, gadget, product and people news. If you are interested in writing for Tech Cocktail please apply here.
Back to top