Are You SquaredOut?
“Tomorrow never knows.” To most, this is better known as a malapropism that famously became a Beatles song, but for Robert Rodrigues, co-founder of SquaredOut, it entails a different meaning. It’s a mental framework of innovative entrepreneurs. It is the summation of a visionary’s journey for a new startup business that most would be afraid to embark on.
However, for Robert it was different; for him it was about taking risks in such a competitive market. It was about not knowing where his product will end up. It was about dipping his feet into a market pool filled with large businesses—the Googles, Apples and Microsofts—and breaking out in the tech world with his product: a social calendar called SquaredOut. It began as a ploy to take social media to the future, but then it moved to the B2B space, eventually targeting small businesses, and it is now geared towards media publications. SquaredOut’s journey consisted of major pivotal changes that led to a complete 180 from its initial standpoint based on market reception.
As with most startups, SquaredOut’s platform development wasn’t established overnight. It took Robert and his team of co-founders countless late hours at the office, white board disagreements, disputes over changes and the hardships of searching for funding to get the business going.
“Making the decisions that we did garnered a lot of mixed reviews. We heard a lot of things—that we’re crazy, stupid or that this is never going to work. I’ve heard it all. There were mixed emotions from friends and family, some encouraging and others not so much,” Robert reveals. “But that’s what being an entrepreneur is about. You take whatever criticism and transform it into fuel to drive your business.”
He concedes the same sentiments of other new startups. The sacrifices that he and his team made mostly concerned financial issues. “Bleeding money is tough. You’re not making any money, and furthermore, you’re putting your own money into the business every day. I didn’t know where my business was going or what tomorrow would bring.”
Being raised by entrepreneurs drove Robert to dive into the business world. The dream was further pursued during his undergraduate career at the University of Arizona where he first met his current team that helped write business ideas for the future. Interestingly, Robert initially didn’t see himself running a social media/tech business. “What I really wanted to be was a restaurateur,” he reveals. “I just wanted to eventually be a billionaire, then start a restaurant, maybe manage a corporate, but more so turn it into a hobby.”
The early stages of developing SquaredOut made Robert feel like giving up, or as he puts it, “at least a million times.” However, thanks to his team, his perseverance prevailed. “Every person has those days, but on different times. But, it’s about lifting each other up when one of us wants to quit.”
That’s the main ingredient required to make business visions come true—the careful selection of a team consisting of like-minded individuals that share the same goals and could contribute on different levels of expertise. SquaredOut employs a small team; co-founders A.J. Mitchell and John Correa, along with a few other members whom, as Robert claims, “wear multiple hats from business to financing to development and sales. We all live, sweat, and breathe this product every day.”
While Robert is happy with an agreeable team, he also acknowledges that having only a “yes” team has its ramifications. “If you don’t disagree on certain things, you’re going to go in every direction. It’s because you don’t know! You have a blank piece of paper to draw a picture, that’s why people use pencils–so you can erase things. Unfortunately with entrepreneurship, you’re writing more with a pen, but that doesn’t mean it’s the end all be all.”
Despite the early struggles of creating SquaredOut, Robert reveals his biggest win of all—next to seeing his product become a reality—“having a great team is a major reward that will never be discounted,” he states. “A.J. was actually the one who came up with the idea. He realized there was a void in social media, a lack of sites that customized schedules, mingle events and personal life. He wanted to find a way to integrate all those aspects. The name even comes from squares of calendar dates… ‘Are you squared out? Are you busy today? What’s coming up tomorrow?’”
Questioning tomorrow indeed, Robert happily accepts this challenge common to startups everywhere, making plans every day and wondering what the future will bring, whether it be another major pivot or developing new features. He has turned his business vision into a reality. Having no prior experience with social media/tech didn’t stop Robert, and having the right team to collaborate with helped immensely. SquaredOut currently has 110 percent of Robert’s attention and “that won’t change anytime soon. I have a lot of belief in my product and future plans for SquaredOut.” Whether that is another pivot or feature that may be implemented, this social calendar has successfully branded itself as a product that could give big businesses a run for their money.