Dre Griggs, Investment Advisor Representative with Obsidian Wisdom

Dre Griggs, Investment Advisor Representative with Obsidian Wisdom https://obsidianwisdom.com/assessment | Take the Retirement Tax Leak Finder Assessment for Free.

10/01/2026

A paid-off house can lower the income you need in retirement. But if you empty your savings to get there, you may trade a mortgage payment for a cash problem.

09/27/2026

If I'm not going to touch my Social Security for the next five years until 67, that gives me five years to do these conversions.

We could do $50,000 a year.

We could probably get away with $100,000 a year.

But we would look at our income and the lifestyle that we want to have.

Then we would decide what makes the most sense for us.

The idea is that we typically have lower taxable income than we had when we were both working.

Now we find ourselves able to do these Roth conversions.

Have tax free income for retirement or our heirs.

And we're still paying less in taxes than we were because we have this low income window.

09/27/2026

How do we classify your rental income?

I'll ask questions.

How long have the people lived there?

Are you charging above market, at market, or below market?

What's the neighborhood like?

How long would it take to get a new person in there?

Then we can create a risk profile.

But I normally like to put plans together conservatively.

Because then we know if there is no one in the rental, we're still okay.

That was how the plan was designed.

Versus the stress and uncertainty where you're like...

"No, someone has to be in the rental. I need to find someone."

I normally put your rentals and your business in the nice to have.

We sell the business for a gazillion dollars?

Fantastic.

Nice to have.

The person lives in the rental for the next 20 years?

Wonderful.

Nice to have.

09/26/2026

The growth bucket is anything that's 10 plus years.

We're trying to be aggressive.

The cool thing is we have the wiggle room.

We can live off our safe bucket for one to three years.

We can live off our moderate bucket for another three to nine years.

And then by that time we're hoping the growth has recovered.

Real estate.

Stocks.

ETFs.

Your hunches.

Your personal business.

Commodities.

Crypto.

Bitcoin.

IPOs.

All of that stuff would be here.

And I know you're gonna be like...

"Dre, it's a sure thing."

I know.

We're still gonna put it in the growth.

09/26/2026

What's the difference between growth and value?

Without getting too technical...

Growth means I found something and it's not quite there yet.

I'm hoping to find it early.

The next Amazon, we'll say.

I am investing because I believe the future looks bright.

Value is different.

This company's already done phenomenal things.

I already see the value in this company.

I'm just trying to find a good price.

We think the stock is on sale, or at least we think it's at a fair price for all the value that is already evident.

Growth...

I believe it will happen one day.

Value...

It's already happened. I'm just trying to find a good price.

09/26/2026

"So I have about $1.2 million sitting inside of my 401K.

I have $100,000 in a Roth.

I have $250,000 inside of a taxable account."

Now I need to figure out what am I going to spend in this five year window to make sure that I have the most of my money that I can leave.

If you want to pass money on to different causes or your heirs, the most flexibility and freedom you have is the money inside of your Roth account.

Why?

You already paid taxes on it once.

Your 401K is different.

You have not paid taxes on it yet.

And Uncle Sam has been patiently waiting for decades.

Required minimum distributions.

The stretch IRA being removed when it goes onto your heirs.

Uncle Sam is pretty serious about making sure that someone is spending the money from that account.

09/26/2026

Most people think having a lower income right after retirement is a big problem.

But I have found that it might be a golden opportunity.

There's this window.

I haven't started my Social Security.

I just stopped working.

I left my highest income earning years.

For a few years, your taxable income might be unusually low.

And you can waste that window.

Or you can take advantage and use that time to move money from your traditional IRA or your 401K into a tax free Roth account.

Because the reality is we can make money and we can keep money.

Sometimes we focus more on the making than we do on the keeping.

The big question is not just...

"How do I lower my taxes this year?"

It's...

"How do I lower the taxes that I have to pay the rest of my life?"

I think that is where the magic ends up happening.

09/20/2026

"Should I pay off my mortgage before retirement?"

I would be cautious if I have a historically low interest rate.

Let's say it's 3% or 2.5%.

There is a math equation to decide.

How much does that money generate for me versus how much does my mortgage cost me?

If the money generates more, then I can take the income that my money generates, pay my mortgage, and have something extra left over.

But I do leave space for our uniqueness.

Some people are like...

"Debt keeps me up at night. It stresses me out."

Then it's like, okay, we need to accelerate the debt.

But my first thought is almost always to look at it from a math equation.

How much is that money worth in my hand today if I invest it versus how much is my money worth if I give it to someone else today and I don't owe them anything going forward?

09/20/2026

From your business's perspective, sometimes my cash flow is not very consistent.

We have seasons.

We have great times.

We have rough times.

Sometimes I don't know if we're gonna make payroll.

There's other times that I have extra money.

So then we would say, all right, we need to figure out how to create a more smooth consumption.

But there's another side.

If your position is not spending money, and then you have the money, and people are willing to borrow your money, it opens you up to a lot more opportunity to have your money give you a higher return.

Now I have so many more options.

I don't even have to take on as much risk because I'm able to get a good return just with a guaranteed interest income source.

09/19/2026

Normally when I talk about money, I talk about it from the perspective of cash flow.

How much money do you need to sustain your life every single month?

And how do we accomplish that?

Then I ask...

Are you comfortable with this amount?

Would you like to lower your monthly payment?

Are you cool increasing your monthly payment?

Because it matters.

The other portion is the money.

I need to make sure I have an emergency fund.

I need to make sure I have this bag of money for whatever experience that you wanna have.

You may have a pension that gives you cash flow, but then you don't have the emergency fund for healthcare expenses or a big unexpected emergency.

It's normally those two perspectives.

Cash flow and the big bucket.

Each of us is a little bit different.

It does matter and it depends for each of us.

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