Starting Today’s Business: My Entrepreneurial Journey

By Tom Ottaiano, CEO, Today’s Business

Everyone wants to be an entrepreneur, but not everyone has what it takes.

From Pizza Boy to Businessman

Starting a business was always in my blood. I grew up in a family that owned their own restaurant for over 40 years so hard work was ingrained in me from the start. When I was young, my weekends consisted of working as a busboy until I learned how to make pizza.

When my business partners and I started building Today’s Business, one of our first offices was above my family’s restaurant, Calabria Restaurant and Pizzeria. It was very fitting that my first step into the business world was under the roof of the business that my family had put so much of their blood, sweat, and tears into for so many years.

Today’s Business

In 2011, I was fresh out of college and chasing down a chance at playing in the NFL. Thankfully I always had the entrepreneurial gene and it wouldn’t let my NFL aspirations stop me from conceiving of Today’s Business simultaneously with my future business partners.

When you have the right business partners, the rest of the pieces have a much better chance of falling into place as they should. The three of us shared the same collective goal of connecting people and businesses, while carving out our own niche in the marketing world. As an athlete, I knew that success would live or die by whether or not we were able to surround ourselves with the right team. We were ready to build something amazing and I was ready to fully commit to Today’s Business. 

In the beginning, we didn’t have much. We had a desk, some notepads, three computers and one dream. That dream was to change the game. It’s now seven years later and we still haven’t stopped chasing that dream.  

Tackling Challenges

According to Bloomberg, 8 out of 10 businesses fail within the first 18 months. From my experience starting a business, I can now see why.

Today’s Business was a challenge from the very beginning. There is no aspect of the role of CEO that is easy and there’s no concise job description with expectations that you can refer back to.

What sets me apart is that I have always enjoyed challenges. I love going into the office every single day knowing that every day I’m going to be tackling something difficult. You can’t succeed in business or marketing if you avoid obstacles.

If I had allowed statistics to fuel fear, such as the Bloomberg one I referenced above, I would not be where I am today. Ultimately, there is nothing more rewarding than pushing away your doubts and being able to stand alongside the 20% of businesses that beat the odds. 18 months is now a distant memory.

Gaining Traction

The real reward of being a business owner is seeing your vision manifest right in front of you. There’s nothing better than taking a step back and thinking, “Wow, I am actually doing this. I’m living out my dreams.”

The first moment where I felt that during my journey was when we signed the Cleveland Cavaliers for a campaign back in 2013. That’s when I knew big things were in the works.

The second moment where I experienced that feeling was when one of our athletes, Chris Hogan, played in the Super Bowl and I was able to be by his side cheering him on.

Regardless of what we have accomplished in the seven years of Today’s Business, I am a firm believer of never taking your foot off the pedal. Gaining traction and seeing success in whatever you are doing should not warrant complacency. It should drive you to be better and to keep learning and achieving.

Stay Hungry

These days, everyone wants to be an entrepreneur, but not everyone has what it takes.

If there is one that I learned during my journey, it’s that you can’t get complacent. You gotta stay hungry and embrace change. My life consists of this company 24/7 and I wouldn’t have it any other way. Every single day I wake up with the unquenchable inner motivation to keep growing and keep building.

Entrepreneurial motivation can’t be taught, it’s something you’re born with.

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