Southern Tax Wisdom with CPA Jason Toole

Some people make taxes feel heavy.
Jason Toole is not one of them.

Sitting in his Atlanta office, we covered everything from kids’ summer jobs to Roth conversions to scalloping in St. Joseph Bay. And somewhere between the laughs and the stories, Jason delivered the most approachable tax conversations we have had on Southern Character. And that’s no easy lift.

This is Southern tax wisdom at its finest.
Clear. Practical. Human.

Welcome to Southern Character with CPA Jason Toole.

Roots, Relationships and the Road to Accounting

Jason grew up in Albany, Georgia, home of Luke Bryan and Buster Posey. He fell in love with the Bulldogs early and only applied to one school. The Hope Scholarship took him to Athens, where he earned his accounting degree.

Like many of us, he did not discover his calling in a straight line. Accounting was hard. One of his professors told him he should probably go into sales. But Jason kept showing up, breaking complex ideas into simple parts until they made sense. He used that same skill years later in client meetings when explaining tax strategy to attorneys and business owners who walk away thinking he made the impossible easy.

After graduation, he joined the firm that would eventually become Kelly Salmons Toole & Ellison. He thought he would stay a couple years, earn his CPA, and maybe move on. Instead, he fell in love with helping entrepreneurs navigate their numbers. He made partner at thirty two.

And then there is Christina. Originally from Miami, raised partly in Albany, she and Jason met the summer before he left for college. They built their life through long distance, graduate school, marriage in 2001, and eventually three daughters: Kiki, Lola, and Nina.

Their family stories alone could be an episode. Nina wants to be a dermatologist and spends her free time in the trauma unit at Grady Hospital. Lola is famously polite and helpful. Kiki is full of energy. Their home is a lively place.

And their dog’s names, Nestle and Libby, round out a full house.

Family is the anchor that shapes how Jason sees his work.

Making Taxes Understandable: What Families Really Need to Know

We opened with a simple question. If your teenager makes money babysitting or running a small camp, do they need to file a tax return?

Jason did not talk in code sections. He talked like a human.

If kids make enough, yes. And most people forget about self employment tax, which kicks in lower than income tax. A teen making four or five thousand dollars may owe no income tax but may still owe self employment tax.

Then he shifted to what matters most:
If a child has earned income, they can start a Roth IRA.
Even a few thousand invested early becomes lightning in a bottle over time.

From teenagers to forty somethings, the same principle holds.
Put money away. Build discipline. Use the tax system as a tool, not a burden.

Jason explained the real tradeoff between traditional and Roth 401k contributions. He described it the way clients actually think:

Should I kick the tax can down the road or pay it now?

The answer depends on cash flow, lifestyle and whether you can stomach the hit today. But his view is simple. If you can afford to pay tax now to fund a Roth, the long term benefit is real.

Still, the most important thing is saving something. Traditional, Roth or a blend. Do what you can.

From there we explored backdoor Roth contributions, small business income, the Secure Act 2.0, IRA limits and why most people never get advice on the moments that matter most: low income years where Roth conversions can be transformational.

Jason brings the same clarity to every topic. He strips away fear and helps people make decisions that fit their lives.

Retirement, Tax Buckets and the Second Half of Life

Jason has watched a generational shift unfold.
His parents’ generation retired and often struggled with purpose.
Today’s retirees are approaching life differently.

He described the second half as a chance to reinvent yourself after a business sale, career transition, or inheritance. And taxes show up in all of it.

He explained how people who retire at sixty have a thirteen year window before required minimum distributions begin. That window is a strategic gift. Families can manage income intentionally, convert portions of IRAs to Roth IRAs at lower tax brackets, and plan ahead for healthcare costs like Medicare premiums.

The theme is simple:
Take advantage of the gaps in your working life.
The tax code rewards planning.

Where to Retire in the South: Tax Friendliness Across States

This is where Jason lit up.
He has prepared thousands of multi state returns and knows the Southern map as well as anyone.

Highlights from our conversation:

• No Southern state taxes Social Security.
• Florida, Texas and Tennessee have no state income tax.
• Georgia is exceptionally friendly with retirement exclusions of $35,000 per person starting at 62 and $65,000 per person after 65.
• Many Georgia retirees pay federal tax but pay zero Georgia tax.
• Pension income rules vary widely from Mississippi to Alabama to South Carolina.
• Property taxes, insurance costs and access to healthcare matter as much as income tax rates.

The data may say Florida.
Jason’s heart still leans toward Georgia.
But he respects the tradeoffs.

Life on the Forgotten Coast: Mexico Beach and the Places That Shape Us

Jason and Christina keep a home in Mexico Beach, Florida. It was their family anchor for years until Hurricane Michael destroyed it in 2018. They rebuilt and now cherish the place even more.

He described the Forgotten Coast as the old Florida many people forgot existed. Quiet. Slow. Community driven. More about the people you bring with you than the places you go.

He lit up talking about Shell Shack seafood spreads, Mango Marley’s wings, and scalloping in St. Joseph Bay. It is not Rosemary Beach. It is not Seaside. It is something different.

It is a place for focus, connection and rest.
A place where memories outnumber distractions.

The Heart of the Work

Jason is proudly Southern.
Albanian by birth. Bulldog by choice.
A CPA who breaks complexity into simple steps.

But more than anything, he is someone who sees taxes as a way to help people build a life with options. A life with margin. A life with purpose.

Those are the stories we share on Southern Character.

This information is provided to you as a resource for informational purposes only and is not to be viewed as specific recommendations. This information is being presented without consideration of the financial circumstances of any individual and might not be suitable for everyone. This information is not intended to, and should not, form a primary basis for any decision that you make. Always consult your own legal, tax, or investment advisor before making any financial planning considerations or decisions. The views and opinions expressed are for educational purposes only as of the date of production and may change without notice at any time based on numerous factors.