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.

08/28/2026

Anything that I'm able to hold as a long term investment, ideally, I would like those investments to be in my taxable account.

That gives me the opportunity to have capital gains taxes, which is about half of ordinary income tax.

I would then look at my highest appreciation investments, and I'll put that in my tax free account.

One of the things I think sometimes people overlook is the benefit of your taxable account.

Inside your taxable account, you have the ability to offset some of your losses with some of your gains, so that way you pay less in taxes.

You also have the opportunity for a step up in basis for your heirs.

Do you ever feel like your money's working more for Uncle Sam than it is for you?

I built a free assessment called the Tax Leak Finder.

In less than five minutes, you can have a personalized plan that gives you the next steps that you should take so that you pay yourself more and the IRS less.

08/27/2026

You can be someone that invests in your REITs purely for aggressive investment growth.

You're someone that's focusing on the appreciation more.

And if that is what we're doing, then we would put that inside of our tax free.

The thought is, I'm gonna buy them low and I'm going to sell them high when I'm in retirement.

But all of that growth in between is not gonna be taxed to me.

Don't you think your money should pay you more than it pays Uncle Sam?

I built a free assessment called the Tax Leak Finder.

In less than five minutes, you'll find out where you might be paying Uncle Sam too much.

It'll give you the strategies you need to implement so that you can keep more of your hard earned money.

08/26/2026

When you're thinking about your taxable account, the goal of our taxable account is to have it taxed at capital gains.

If it's capital gains, it's a 0 to 20% rate.

My tax deferred is gonna be taxed at ordinary income, so that's 0 to 37%.

So you can see it's already about half of the taxable income to have it as capital gains.

But here's where it gets interesting.

You actually want to have your highest growth inside of your tax free account because it's 0%.

If I found my Amazon and I put it inside my tax free account, and the stock grows by 3,000%, all of that growth is tax free.

Don't you think your money should pay you more than it pays Uncle Sam?

When we're thinking of taxes, that is how much I get to keep from Uncle Sam.Most people I see have their money in their ...
08/25/2026

When we're thinking of taxes, that is how much I get to keep from Uncle Sam.

Most people I see have their money in their pre tax account.

If most of your money is in those accounts, then you haven't paid taxes on it yet, and it will be taxed as ordinary income.

I don't know what taxes will be in the future.

Is Uncle Sam about to take more of my money than I was planning?

We would like our money.

We have to have a coordinated strategy to be able to keep the money.

08/25/2026

If something crazy goes on, historically speaking, there has not been a time where after a few years, it’s still going down.

COVID was a handful of months. The Great Recession was really bad for a couple years. 9/11 was bad for about a year.

If I have something to hold me over for a year to three, I’m probably gonna be able to ride out that recession.

And I won’t lose the money for my investments. They will recover.

Retirement isn’t just about how much money you have.It’s about how your money is working for you.I think about retiremen...
08/21/2026

Retirement isn’t just about how much money you have.

It’s about how your money is working for you.

I think about retirement income in three buckets:

Safe. Moderate. Growth.

The goal isn’t to put everything in one place.

It’s to have money working in different ways so you can separate your time from your money.

Because ultimately, retirement is about purchasing your time back.

Plan today. Live tomorrow.

08/21/2026

What is the difference between value and growth?

Value means you've already generated the money.

You're a very successful company. You've been around. You've done this for a long time.

I just want to get a good value.

I just want a good price for this investment.

I'm not investing in growth.

Growth means you haven't done it yet.

But I have a good feeling about your future.

That's growth.

So that would be aggressive.

Moderate means you've done it.

I'm not taking a huge risk.

I'm just trying to get a good price.

If you wanna see where you stand, I built a free tool called the Tax Leak Finder.

20 questions in less than five minutes.

You'll get a personalized report showing you whether your retirement tax plan is on track or leaking.

Go to Obsidian Wisdom.com to learn more.

08/20/2026

7 out of 10 people 65 and older will have at least one long term care need.

On average, it's three years over the life of your retirement.

And the average cost is about $60,000 a year.

That means you have to think about how you're going to handle those costs.

Healthcare costs outpace normal inflation.

It's about 6% every year, while normal inflation is about 3% every year.

So I need some of my investments to, at a minimum, keep up with healthcare costs.

Or I get long term care insurance.

Those are your two options.

08/19/2026

If you could go back in time and leave yourself something in a safe, what would you choose?

$100,000 in cash?

$100,000 worth of property?

Or $100,000 that they bought in the stock market 100 years ago?

I think we all recognize if it's $100,000 of cash that we're in trouble.

That is probably the worst of the options available.

Because everything else has exponentially increased because its value is exponentially greater than our money.

You start seeing this and you're like, "I have to invest my money in something, otherwise I won't be able to afford anything in my life."

You have to.

Do you ever feel like your money's working more for Uncle Sam than it is for you?

If you have that question, I have a free assessment called the Tax Leak Finder.

In less than five minutes, you can have a personalized plan that gives you the next steps that you should take so that you pay yourself more and the IRS less.

Go to obsidianwisdom.com or the link below.

08/18/2026

Would you have guessed that a dozen eggs cost about a dollar in 2000?

Someone who retired in 2000 would be sitting here today needing five to $10 for a carton of eggs.

And that's the problem with inflation.

If I just put all my money in a bank account and got paid 3 or 4%, you and I both know that isn't sustainable.

We have to invest the money in something that outpaces inflation.

Otherwise, I am progressively just losing money every single year.

Think about car payments.

There was a point in time that having a three year car payment was normal.

Then five years was normal.

Now people are talking about six and seven year car payments.

There was a point in time that having a $250 monthly car payment was normal.

Now it's normal to have an $800 to $1,000 car payment.

If you just live, inflation requires you to keep up with it.

Otherwise, you can't afford your lifestyle.

Your money has to keep up.

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