Lessons Learned from Shutting Down My Second Startup

posted in: Startup Life | 5

Two years ago, when I wrote a post-mortem for News Armada, I was an overly-ambitious first-time entrepreneur, chasing dreams of venture funding and changing the world on my first time up to bat. I learned two important lessons from that experience:

  1. Momentum is everything. Lost momentum isn’t just missed opportunity, it’s a weight that slows your startup down.
  2. Value before revenue. Don’t spend all your time working on a plan to generate revenue from a community / product before you’ve proven that it provides enough value to people that they’re willing to use / pay for it. Market traction first, revenue extraction later.

After that experience, I wasn’t eager to spend years creating something great and looking for funding before I ever saw a real dollar of profit come from it. Big ideas always go through multiple stages before they reach their real potential — I wanted to start with a business much more simple. Creating a product that solves a problem, that people will pay for.

My mother publishes a real estate magazine in the southeast, and has since I was a child. Some of my first efforts in web development was creating & maintaining websites for real estate agents in my hometown. In the ten+ years since then, it struck me that most Realtor websites weren’t much better than what I was able to create at 13. It seemed like a clear enough problem: agents have crappy websites that don’t effectively get them traffic, get them leads, or market their listings.

Some market research indicated that there were many services that provided agents with websites (a good sign that there was demand for it), and that almost all of them were doing a crummy job of it (by the standards of someone who uses the web on a regular basis). My co-founder Andrew mentioned he had a friend in California he’d worked with before who did a steady business creating websites for people with Drupal, a powerful CMS I was aware of (though I had worked more with WordPress).

And that’s how EasyImpress began. I won’t recount the next 2 years in detail; I want this post to provide actionable advice, not just narrative. So without further ado, here are my takeaways:

Do Not Start a Startup Without a Full-Time* Team

I don’t think I would ever start a business again without:

  1. Enough savings to keep me housed & fed for 6 months (and therefore no need to work on other things to meet basic needs), if not longer.
  2. Everyone on the founding team committed to work 20+ hours a week on starting the project, and a clear milestone at which they were willing to make it priority #1.

Startup culture idolizes people who quit everything and instantly commit 100% to a new venture. Realistically, many of us who want to start a business of our own aren’t in a position to do this, because of responsibilities we have to others. And rarely are the best potential co-founders unengaged with other projects. But I would never again want to be a founder of a startup I wasn’t able to bring 100% of my time to.

Carefully Consider Doing Anything You Are Not Passionate About

Startup life is very unstructured. It’s up to you to motivate yourself, and even if what your startup will bring you (stability? wealth? importance? credibility?) motivates you, you will find it much easier to work on the daily tasks and everyday challenges of building a business if the business itself is something you’re passionate about.

Self-motivation is not an ability that once you have it, you keep it. It’s a reservoir of will that’s filled with ambition, enjoyment, good humor, and small successes. It’s drained by mundanity, difficulty, failures, and fears. If you’re not refilling that reservoir on a regular basis, you will find yourself attempting to escape or avoid further drain.

There are many good business opportunities that I find interesting, though maybe I’m not inherently passionate about them. My new rule of thumb: if I can’t bring an opportunity to fruition (providing reservoir-refilling successes, emotional and/or financial) within 6 months, I’m not going to pursue it.

Don’t Use a Platform More Complex than Your Solution

One advantage we had was that I knew our market well. Most real estate agents are not web savvy, and one of the reasons so many agent websites were terrible was because the services providing the tools to create them were unintuitive and overly complex. Simple was one of our mantras from the beginning. We hid Drupal’s techie-focused control interface from the end user and provided an interface that started with 3 simple menus: Add, Edit, and Options.

Drupal was attractive because it provided all of the CMS functionality we needed, and had a thriving ecosystem of add-on modules that provided additional functionality. Surely it would be easy for us to pick-and-choose what we wanted, right? Wrong. Using Drupal was probably our worst mistake, because it reduced the efficiency of the time we were able to spend on the project significantly.

Instead of spending time creating or improving functionality, much of our development time was spent trying to figure out what in Drupal was causing something to happen, which module was interfering with another’s operation, or how to modify something Drupal simply didn’t provide a hook for. And Drupal itself provided tons of functionality that we didn’t need at all, and was just dead-weight in memory usage.

When it comes to technology platforms, it’s often easier to add things on than it is to take things out or untangle abstraction. Don’t start with a platform that does more than what you need.

If Things Aren’t Going Well, Persevere but Set Milestones to Sop

One of my biggest regrets after shutting the doors on EasyImpress is not doing it 3, maybe 6 months sooner. Our team had been feeling negative about the project for a while. Part of that is the ups and downs of the startup roller coaster. I don’t think anyone should quit their startup because they’re at a slow point or are feeling negative about its prospects. But I don’t think you should push blindly forward, either.

Set clear conditions (no sales after X months, fewer than X hours worked by team each week, unable to solve problem after X dollars more spent working on it, etc.) at which you’re going to cut your losses, and stick to them. Don’t get stuck worrying about sunk costs. If you keep working past your points of failure, you’re not just losing more money and effort; you’re losing time to put into other opportunities you could be pursuing.

The best part of shutting down our startup is that we’re now able to work on things that will reward us.