The Reality of Starting a Business With Your Best Friends

By Tom Ottaiano, CEO, Today’s Business

Before Today’s Business

My business partner, Chaz, and I played football together at Hofstra University way before we had the idea to start Today’s Business. From the get-go it was obvious that we were both competitive people by nature. We carried that into our business partnership years later. After graduation, we knew we wanted to carry on the tradition of being part of a team, but this time we wanted to lead the team from top to bottom.

Billy came into the picture when we were in the early days of figuring out how we were going to start the business. He had a passion for everything digital and he was the missing piece of the puzzle that jump-started our journey. Billy and I couldn’t be more opposite in every way, and that’s what makes our dynamic within Today’s Business great. I always say we’re like oil and vinegar, separated at first, but when you shake it up into dressing, something special happens.

And just like that, Today’s Business was born, along with our roles as CEO, President, and CDO.

Don’t Listen to the Negativity

There are many people out there that will tell you that going into business with your best friends is a bad idea. They will tell you that it won’t work out, that your friendship won’t last, or the business will cave in.

Put aside that negativity and push through your goals. If you and your friends believe in your dream, now is the time for action, not hesitation. A real entrepreneur is able to take the doubt and turn it into fuel, and further down the line…success.

Are You Ready?

Here are some factors to consider for both your partners and yourself before taking the leap and starting your own business:

  • Do you know your partner very well?

You need to know who your partner is better than anyone else. Make sure that you’ve known them long enough and you are close enough to be able to know how they react to things, how they think, and what type of worker they are.

  • Do you each have a clear understanding of your responsibilities within the company?

Establishing roles early on is one of the keys to a successful business partnership. You each need to know your responsibilities from the start or else nothing will get done and your company won’t grow.

  • Are they someone that you will be okay with talking to day in and day out for the long haul?

Your potential business partner can’t be someone you’re going to get sick of easily, because you will end up spending more time with them than your immediate family. In many ways, a business partnership is like a marriage. Are you ready for that commitment?

  • Are you able to make decisions with a clear mind that isn’t clouded by emotions?

Friendship raises the stakes of all business decisions that you make. It often blurs judgments. As business partners, you all need to possess the ability to make level-headed business decisions that are based on what is best for the company, not what is best for the friendship.

  • Do you each have skill sets that are different and balance each other out?

It’s important for everyone to have their own expertise that they bring to the table. Knowing each other’s strengths and weaknesses is crucial when it comes to building a business plan.

If you’ve answered yes to these questions, chances are a successful business partnership is on the horizon.

Always Put the Business First

It takes a strong core team to stay together.

When you start a company with your friends, you all need to have a clear understanding that no matter what happens or what problems come up, no one is bigger than the business.

I wholeheartedly believe that one of the reasons that Chaz, Billy, and I have all had such a harmonious and successful business partnership is because at the end of the day, we put the business before our friendship.

Coming to work alongside your closest friends every day might sound like a fun hangout, but it’s not all sunshine and rainbows. You need to be the types of people that can draw clear lines between the business and the friendship and effectively iron out each of your roles.

Most importantly, we made a pact that no matter what happens in our professional and personal lives, we are ultimately going to get things done and have fun doing it as a team.