02/01/2013 04:21 pm ET Updated Apr 03, 2013

Lessons Learned

I joined my first startup about four years ago, in what I thought was early in the life of the company. We had about 50 paying enterprise customers using the company's product who were willing and eager to share feedback to make the product better. At the time, I assumed the company was in its infancy, and I was going to help build it from the ground up. But I overlooked one glaring fact; that company already had a product people were paying for and actively using. It turns out this is more like adolescence rather than infancy and while I was there, we were lucky enough to grow our user base and add customers to our subscription service.

The company grew to the point where we were actually profitable on a monthly basis. This was a big step from where we were earlier, when we were not generating enough revenue to cover our costs. I analogize my time at the company to revving a car up from 20 miles per hour to 100 miles per hour, 20 being consistently generating revenue and, after you've continued to work really hard and really step on the gas, 100 being profitable and growing. In getting from 20 to 100, we faced many high-level challenges in a variety of areas including sales, marketing, pricing and product development. Many of these presented themselves as symptoms of larger problems. Since we were trying to cure them one at a time, it often felt like we could die from a thousand cuts and never make it to the promised land.

Essentially, we were facing a "scaling problem," but I didn't realize it at the time since I did not go to business school and this was my first startup experience. In my naïve mind, all startups were equal in the sense that we were young companies trying to grow. As we grew and overcame the challenges of scaling a product that our customers needed and loved, I put those lessons learned away for the next start-up -- preferably one I founded myself. I honestly thought the hardest challenge of my professional life was behind me.

Eventually, I left the first startup with the dream of building my own startup, TheSquareFoot. I learned everything I needed to know, right? Wrong.

I had no appreciation for the work that it took to get from the idea stage to the paying-customers-who-loved-the-product stage, or to continue our car metaphor: from zero to 20 miles per hour. I completely glossed over all the things it took to get a good idea off the ground (assuming we even had a good idea). We had to determine if there was product-market fit, the size of the market, what people were willing to pay... and this was just the beginning of a list that grows and grows each day.

What I learned was that getting a business from the idea stage to something people would actually pay for was a whole different ballgame (and much harder) than it was to take a business with existing customers and grow into a sustainable business. Even the lessons that I thought I learned at the first company may not be terribly useful in my new startup.

One lesson that I have definitely learned going through both of these experiences was that you never know as much as you think you know. And the most important lesson learned -- enjoy the ride.