Jorey Ramer

The most rewarding aspect of entrepreneurship is seeing what started as a vague idea become a very specific reality. I knew what I was looking for on day one, and I knew what it would look like. It took me time to figure out how to articulate it, how to get there, and who to work with to get there. But what we are doing today is exactly what I originally envisioned. The frustration is that I know where I want us to be in the future, and it will take time to get there. But once we get through those challenges and investments, the business will be that much more fulfilling.

First, to your previous question about what makes entrepreneurship fulfilling and frustrating, everything takes longer than you expected; there are always more details to be covered than what was anticipated when you first envisioned the idea. Second, every day I feel like entrepreneurship is about having the patience to endure taking two steps forward and one step back; folks might find me to be surprisingly calm with both good news and bad news because I know something different is likely coming next. Third, don’t get discouraged by having to kiss many frogs to find your investors; the investors that do invest are usually the ones who are surprisingly the most logical in hindsight.

Jumptap was at the center of everything emerging in mobile for almost a decade because app developers either needed to advertise with us or receive advertising from us. The businesses that I always envied the most were the subscription businesses because they, more so seemingly than any other businesses, knew their lifetime customer value and their cost of customer acquisition. They had seemingly unlimited budgets to spend as long as you could achieve a particular customer acquisition cost. I was always fascinated by those businesses. This was an ingredient in my aha moment with Super. I was experiencing the pains of homeownership. I had nostalgia for my days of renting. And it occurred to me that there needed to be a subscription business that could recapture that renter-like experience.

Whenever people ask me for advice related to entrepreneurship, I always make the analogy to Bill Murray in Groundhog Day (or Tom Cruise in Edge of Tomorrow). You’ll face challenges and setbacks, as you would expect, but you must continue to put yourself in a position where you continue to face the possibility of failure and diligently learn from each of those events to improve your process. If you do, you will have already encountered virtually every obstacle and attempted every way of handling such issues. After that, you know you have the right approach moving forward.