One page to rule them all.

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A little about me...

I’m Carole Jackson.

After a short stint in commercial banking in Miami, a full career as a U.S. diplomat (Foreign Service Officer), and a lifetime informally advising friends, colleagues, and family about their personal finances, I founded Tradewinds in 2016 as a Registered Investment Advisor (Florida).  My goals: to help reduce the wealth gap through better financial decisionmaking, and to help guide those seeking Financial Independence or to Retire Early (FI/RE).

However, I came to realize that my view as a holistic financial planner encompassed much more than investments — actually, most people can do just as well using the brokerage firms’ robo-advisers — but they needed help balancing their goals against their income, as well as understanding and making decisions about the rest of their financial life.  That’s my strength!s

Services

Income Tax Planning and Tax Return Preparation

Do you understand your tax return? You shouldn't be surprised at tax time if you've been adequately counseled. In addition to preparing your tax return, we make sure to advise you as to future actions you might consider in order to lessen your tax burden legally, and to improve your future financial position.


Retirement Planning

Your retirement plan can't be made in a vacuum. We'll look at your entire financial situation -- who you need to take care of, and when, and help you figure out how.







Business Services

Starting a new business? Do you have a business problem you need help addressing?

With 30+ years experience advising businesses of all kinds in the U.S. and abroad, we can help. From business formation and new business advice to helping you research business and investment possibilities, why not talk to us?

All the bells and whistles

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What people are saying...

Carole was referred to me with only 3 days before the October tax extension deadline. She came to my home, reviewed my documents, and figured out a capital gains question I was worried about. With that question answered, she found a way to file my return free of charge. charging me only for the tax advice.
Trina C
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Carole was able to quickly and efficiently answer all my questions and complete my federal and two state income tax returns -- with business income -- in record time!

Kevin C.
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Carole is a long-time friend, but I've consulted her for years about issues related to various tax return issues. This year was the first time she completed and e-filed my entire return. She's thorough and caring and I will use her again!
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Doris M.
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Contact Us

Click below to book a no-obligation 15-minute consultation so we can see if it makes sense to work together.  We won’t spam you and won’t save your name or contact information unless you become a client.

If we’ve talked and you want us to prepare your federal and selected state income tax return(s), please click here to start registering and uploading your documents.

ADDRESS: Office hours by appointment only.  

We’re in Cutler Bay, FL but most of our work is done virtually.  We can meet at your home or office, at a cafe (like Starbucks or Panera), at a library, or at my home for established clients.

We participate in the IRS’s Annual Filing Season Program.

We prepare Federal income tax returns and most state returns.  We do not generally prepare returns for residents of the following 7 states: California, Connecticut, Illinois, Maryland, Nevada, New York, or Oregon returns except by prior agreement on an individual return basis.

 

Let's talk -- or meet!

Book a free, 20-minute, no-obligation consultation with us so we can both find out whether it makes sense for us to work together!

 

Our contact info

Office Hours

Monday – Friday:

Saturday:

Sunday:

10:00 AM – 5:00 PM

By prior arrangement

Closed

Office hours are by appointment.  We do not take “walk-ins.”  After we talk during our discovery call, we can make an appointment at a date and time convenient for all of us.

Most appointments are virtual, but we can also meet at a nearby cafe, library, or coworking space.  At your convenience, we can also meet at your office (or at your home, if you were referred by a friend or current client) for a modest additional service charge based on round trip mileage from Cutler Bay.