The idea that executives could only be found wearing suits or golfing gear pretty much went out the window with Mark Zuckerberg and Steve Jobs. And while the image of the buttoned-up CEO is less pervasive these days -- especially in Silicon Valley -- it can be hard to picture yourself running a business. I certainly never saw myself as the president of a multi-million dollar company when I helped write my first business plan.
I started a business as a young, inexperienced college student, and it’s become one of the fastest growing software companies in real estate, pulling in $100 million in revenue every year. Here’s how being young and fearless took me from pre-law student to executive.
Dive in and work hard.
Technically, the first business I started with my partner, Dave Bateman, was charging people around town to paint their addresses on the curbs outside their homes. We were in college, but from day one, we had creative drive and were always entrepreneurial-minded, constantly looking for the next thing that would entertain us or make us money.
The next business we started sprang from our difficulties receiving mail as humanitarian volunteers in Honduras. It grew into an internet retail service that now sends hundreds of thousands of letters and packages per year. We were trying to solve a problem that we had at least a baseline experience with.
Conversely, when we started Entrata -- formerly known as Property Solutions -- all we had was an idea. We didn’t know anything about the real estate or property management world. We also knew very little about engineering or building a tech platform or product. We started by writing a business plan for a university competition -- which we won -- and from there, it was a long learning process to understand the space we were suddenly breaking into.
We started the company in 2003 but didn’t close our first really big deal until five years later. That slow ramp up was mainly due to our inexperience and lack of knowledge in the industry. As a naïve college student, I had no idea what a long process it would be. We often worked 14-plus hour days. It was grueling -- and it was fun -- but I woke up six years later, and we still had no money. We reinvested every last penny into the business and things were lean for a long time, but we put in the work to become experts in the industry, and eventually it paid off.
Leave fear at the door.
The best thing about being young and inexperienced was that it made us basically fearless. As kids, Dave and I were both avid pranksters; it was a main building block of our friendship. We even claim to be the originators of the poo-dollar prank (yes, it’s just what it sounds like). Thankfully our sense of humor has matured significantly since those days. And even though they were often a bit sophomoric in nature, these pranks taught us not to be afraid of restrictive social boundaries. This greatly influenced the fact that we weren’t afraid to take on those companies that had been in the industry for 30 years -- even though we were still in college.
I’m not proud of some of the things we did as teenagers, but there is something to be said about not being afraid to do something crazy and letting that propel you to success. When we won the business plan competition that launched us into starting a full-fledged company, we simply didn’t know enough to be scared. We were inexperienced undergraduates going up against MBA and Harvard students. On the surface, we didn’t have what it took to go against them, but we didn’t let that worry us, and it paid off big time.
When we decided to take our winning business plan and turn it into an actual company, we didn’t hesitate to question the status quo, take on the establishment and create technology that is revolutionizing the industry. We were just foolish enough to think we could go against the big guys. And it worked.
It wasn’t easy. There were times in the early days of the company when I almost felt like I was pretending to be the typical executive I thought was expected in the business world. It took me a while to figure out the type of leader I wanted to be and what kind of company we wanted to be. Eventually, we let that go and just decided to be ourselves.
In the beginning of the internet retail service before Entrata, we had to ask friends to help us fold letters. We paid them in pizza. It took a similar mentality to help us when Entrata was still so small that we were hardly noticeable. At our first tradeshows, we did whatever we could to stand out, even though we were a small business next to huge corporations. We wore classic, bright red Vans as we walked the tradeshow floor and hired break-dancers to get attention instead of spending thousands of dollars on sponsorships that got our name on a napkin. Later, we hired 100 temporary employees to walk a tradeshow floor and make it look like we were a much bigger company than we were at the time.
Since then, we’ve established a strong company culture centered on unique values, guerilla marketing and authenticity. Now, people know our company’s personality. Our customers are a part of our family and wear classic red Vans with us to every tradeshow and event. We like to have fun. But the one thing all CEOs of successful companies have in common is dedication. Realize what kind of executive you are and what kind of company you want to build. and stay true to that. If you work hard and go for it, anyone has the potential to make something big.