5. Landing Your First Three Customers Is The Most Difficult Part

Getting businesses to put their reputations -- and possibly some people’s careers -- on the line to sign with a startup is a big deal, Chesonis said.

"Those are the accounts you want to make sure that you are saving them a ton of money and make them look phenomenal to their leadership and shareholders, that you go crazy servicing the living daylights out of them because they need to be your best referral customers," he said. "You cannot have (a) misfire on your first three contracts."

Even solution provider businesses that are established but trying to offer a different product or new solution will face the same challenges signing up the first three customers, he said.

"This is why I love the channel," Chesonis added. "Half the battle is having someone like a partner that is a trusted advisor to that client [to take] half the fear way."