Charles Vaccaro

Never give up.


Born and raised in Nassau County, Long Island, New York. Charles Vaccaro attended St John’s University and CW Post College. He started his professional career in the computer printer ribbon manufacturing business. This was his family business that he took over and grew it to over 100 employees. Under Charles’s leadership, the Business manufactured for the biggest names in the dot matrix printer business including Epson, Canon, and many others. He successfully executed his first leveraged buyout of a competitor at the age of 28. Charles then grew in his professional journey by starting and purchasing businesses, including a securities broker dealer and a proprietary trading firm that employed 2,000 traders. Today, Charles Vaccaro is the President of Sunny Isles Capital LLC, a private equity firm that specializes in providing capital to start up and growing OTC Listed companies, including consulting on mergers and acquisitions.

Where did the idea for Sunny Isles Capital come from?

The idea for Sunny Isles Capital LLC was born from my experience in running a small publicly traded firm and the need for working capital. A small company’s biggest challenge is having sufficient working and growth capital available when they need it. Sunny Isles Capital understands the landscape and will provide capital where banks will not.

What does your typical day look like and how do you make it productive?

A typical day at the office for me is consumed by reviewing new deals that come across my desk and managing positions in companies that we have funded. We are most productive by only reviewing deals that meet our requirements and quickly rejecting ones that do not. There is no time to waste on a maybe.

How do you bring ideas to life?

We supply capital to firms that have a management team in place that can execute their business plan and a product line that we believe will be the next best thing. My goal always is Identifying trends before they happen, not following them.

What’s one trend that excites you?

I am currently excited about the cannabis sector, and the crypto currency sphere. I believe we have a lot of growth yet to come in the cannabis game, and with crypto currency, the technology is still fresh and advancing.

What is one habit of yours that makes you more productive as an entrepreneur?

The will to work long hours and the ability to never give up. I have found persistence to be the key in achieving any goals you have. Luck can run out, but hard work always lasts.

What advice would you give your younger self?

Cash is king, and without it you are at a great disadvantage, so preserve and protect your cash reserves above all.

Tell us something that’s true that almost nobody agrees with you on.

Being successful is very hard and sometimes requires a great deal of suffering. At my lowest point basically everyone I knew thought I should take a job and give up my dream. I would not accept failure and continued on against everyone’s judgement and ultimately proved them all wrong.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Never ever give up.

What is one strategy that has helped you grow your business?

It starts from the very top of an organization, with effective leadership that can guide and navigate a company that others would recommend. Do what you say and soon your reputation will follow.

What is one failure you had as an entrepreneur, and how did you overcome it?

For me it was believing that others would actually help in times of need. False promises of capital investments from other private equity firms when I was on the side of needing capital. That experience ultimately led me to establish Sunny Isles Capital LLC. Know your space and communicate quickly and honestly with firms that need your help.

What is one business idea that you’re willing to give away to our readers?

My idea would be to develop an app that could monitor the speed of cars from your smart phone. If the app shows that a car in your area is speeding, it would send that data along with a picture of the car and license plate to the local municipality. The local municipality would issue the driver a speeding ticket via mail and the app holder would get a share in the ticket proceeds. It would effectively be like having millions of police and/or traffic cameras monitoring the roads with no infrastructure cost to the municipality.

What is the best $100 you recently spent? What and why?

Buying a Delta Airlines first class ticket vs coach. The coach tickets require you to pay for the second piece of luggage usually $25-$50, and if you have a third piece of luggage it could be an additional $75. First class tickets allow up to three free bags, priority boarding, a meal, drinks, and a much more comfortable seat.

What is one piece of software or a web service that helps you be productive?

Cam-Scan, I use it daily and allows me to be productive wherever I am.

What is the one book that you recommend our community should read and why?

The Little Blue Book that Beat Wall Street, written by Joel Greenblatt. It explains investing in stocks that anyone can understand and breaks it down to the simplest terms.

What is your favorite quote?

I was never rich enough to buy cheap.

Key Learnings:

  • Never Give Up
  • Protect your cash reserves.
  • Believe in yourself
  • Do as you say.