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.

09/08/2026

Everything is supply and demand.

We're telling everyone to go to college, and people are taking very general degrees and understandings.

They're not necessarily trying to find a niche in their career or in their skillsets.

And that opens you up to competing with everyone.

If you're a generalist, you're competing with people at a very high level.

Versus if you work your way down into a very specific skillset, now you're a big fish in a small pond.

So it's not as much whether college makes sense.

It's now a question of each individual degree.

Does that degree make sense for me?

If you want to be a lawyer or a doctor, that still makes sense.

If you want to be a chef, I don't know if you should go to college to be a chef.

It depends on what you're gonna do with that skill set.

Every single degree is not a, "Oh, for sure, this will definitely make me money."

09/08/2026

You don't go to college, but you have a specific trade that you now have mastered.

You're a plumber. You're an electrician.

Even I see very successful where they cut down trees.

You have a specific skill set.

When I need that particular problem solved, I need to know that that person exists.

Someone with that experience, certification, or training where I know they can solve that very specific problem.

AI is sort of what's causing this.

If you have general knowledge, AI has all the general knowledge that you can need.

If you have specific knowledge, a unique set of life experiences and skills that you've put together, you can create an economic value that gives you a leg up.

09/04/2026

If you're retiring at 62, it leaves you with one problem.

Medicare doesn't start till 65.

And so that is a three year gap.

Before I tell somebody that they're ready to retire, I want to know, where is your health insurance going to come from?

Whatever that answer is, I like to put an actual number on it.

Let's say your health insurance and out of pocket costs during that three year period adds up to about $15,000 a year.

That's $45,000.

That's definitely not a reason to say, "I can't retire till 65."

But it is a reason to say, "We need to bridge that."

Don't retire at 62 and then treat healthcare at 65 like future you's problem.

We're not supposed to worry about the future.

Doesn't mean we don't plan for the future.

Make the best decision with the information you have and move on.

09/04/2026

You get your FRS retirement options, and option one gives you the biggest monthly check.

And so you think, well, that's pretty easy. Give me the biggest check.

What is there really to overthink about?

But the reality is that bigger check comes with a cost.

If you're married, you have another question to answer.

What happens to my spouse if I pass first?

The survivor option may give you less income today in exchange for continuing income for your spouse.

Now, if you're someone that has already set up an additional income stream, then it gives you that unique ability to take the full amount on your life.

The thought is, if I was to give up, let's say, $500 a month, well, what if I had an insurance premium that was less than that?

Then I could take the largest amount.

That additional $6,000 a year is $60,000 every 10 years.

You can see how it adds up relatively quickly.

If you don't already have something in place to protect your spouse, then you really wanna think strongly about whether it makes the most sense to take what we call the love option, where it covers you and your spouse.

09/04/2026

So number one, you want to find your real income gap.

I only need $84,000 a year.

My pension already is generating $48,000 a year, so your retirement doesn't need to actually produce $84,000.

Your initial gap is just $36,000 a year.

And that's the number that I care about the most.

Then Social Security enters the picture.

Let's say your Social Security at 67 will be another $3,000 a month.

Now you have your FRS pension, which is $48,000.

You have your Social Security, which is $36,000.

That gives you a total guaranteed income floor of $84,000.

And that happens to equal our hypothetical spending goal.

The job of your portfolio has changed.

It doesn't have to fund your entire retirement.

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.

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