Dre Griggs, Investment Advisor Representative with Obsidian Wisdom

Dre Griggs, Investment Advisor Representative with Obsidian Wisdom Wondering if your retirement strategy is truly tax-smart? Take the Tax-Smart Retirement Stage Assessment at https://obsidianwisdom.com/assessment

06/02/2026

The way I think about spending money is like playing Monopoly.

When I'm playing Monopoly, my goal is to get as many income producing assets as I possibly can.

If I land on a railroad, I'm buying it.

If I land on a property, I'm buying it.

If I land on free parking, I'm upset because I wasted my turn.

Passing Go and collecting $200 is our time for our money.

That's our paycheck.

But if we don't buy assets that start generating more money than the time it takes us to go around the board, you will lose in Monopoly.

No matter how much money you have.

No matter how lucky you've been.

The only way to win is to have something generating money for you that is quicker than you going around the board with your time.

That's how Monopoly works.

And that's how I think about retirement.

06/02/2026

I find that maybe our lifestyle is relatively expensive because we have a bunch of debt.

We are conditioned to get the job and then get the house to celebrate the fact that we got the job.

Then you get the car because you've been struggling, you've been trying to make it, and you finally made it.

But now we've built a lifestyle that requires us to keep working.

If you didn't have the debt and you were able to allocate more of your money towards your freedom fund and your separation of your time from your money, we would feel much different.

A lot of us are spending our money that is to purchase our freedom on semblances of freedom.

Things that make us feel like we're free.

But we're actually indebting ourselves to the system for another two years, another three years, another five years.

06/01/2026

When I use the word retirement, most people are like, "No, I'm not gonna retire for at least 10, 15, maybe 20 years. Dude, I got plenty of time."

But if retirement is separating your time from your money, what age do you think it's important to separate your time from your money?

You'd probably say, "As soon as possible."

You don't have to stop working.

You just don't have to work for money.

When wisdom equals freedom, now I work and volunteer and I travel and I do all the things I've always wanted to do.

Now all that time is mine.

That's freedom.

That's what the game is about.

That's what we're playing for.

And we're playing to win.

06/01/2026

I meet people all the time who are investing like they are 35.

But they are actually retiring in 10 or 15 months.

And that always leads to the same question.

How do we feel about the risk?

Because there are a handful of reasons people run out of money in retirement.

Some people are not invested aggressively enough.

So they are not outpacing inflation.

Some people are not planning for healthcare costs.

Some people outlive their money.

Some people pay too much in taxes.

And some become too dependent on Social Security.

The challenge is finding the balance.

Too much risk creates one problem.

Not enough risk creates another.

Think about a carton of eggs.

In 2001, a carton of eggs cost about $1.

Today, that same carton of eggs may cost $5 to $10.

If your retirement plan was built around $1 eggs.

How do you afford $5 to $10 eggs twenty years later?

That is why inflation matters.

That is why risk matters.

And that is why your retirement plan needs to address more than just investment returns.

05/31/2026

I meet people all the time on different ends of the spectrum.

Some people say.

My time is so valuable.

I have a chef.

I have someone who picks up my kids.

I have someone who takes out my trash.

Mows my grass.

I even have a private jet because I do not want to spend time standing in an airport.

Then there are people who do everything themselves.

The interesting thing is.

We all have a number in our head.

We all have an idea of what our time is worth.

And based on that number.

We make decisions.

If you are a business owner.

Think about the first employee you hired.

That was the moment you decided your time was too valuable to keep doing every task yourself.

That is really what time allocation is.

Deciding where your time creates the most value.

And saying no to the things that do not.

05/31/2026

Fees are one of the most overlooked parts of retirement planning.

There is a study that says 56% of people believe they pay no fees inside their 401(k).

I am here to tell you that is not the case.

There are layers of fees.

You have the fee for the 401(k) itself.

You have the fees for the fund managers.

You may have fees inside the investments being used.

And there can be other costs people never realize are there.

I remember reading about target date funds.

People like them because they rebalance automatically.

But the fees can end up being relatively high for the amount of service you are receiving.

The interesting thing is this.

I am not someone who believes the cheapest option is automatically the best option.

The real question is value.

What am I receiving for my money?

If the value is there.

And it saves me time.

Then the fee may make sense.

But first.

You need to know what you are paying.

05/30/2026

One of the biggest mistakes people make is investing money without asking one simple question.

How soon do I need this money?

If the money is for a down payment on a home in two years.

Then we should focus on capital preservation.

I do not want to invest it aggressively.

If the money is for a kid's college fund ten years from now.

That is a completely different conversation.

Time horizon matters.

Because we know recessions happen.

And if I have enough time, I can recover from that recession.

If I do not have enough time.

Then I need liquidity so I can wait it out.

What normally happens during those economic environments?

The government lowers interest rates.

Money becomes cheap.

Businesses start growing.

The stock market grows.

People can borrow money for homes more cheaply.

And money starts flowing through the economy again.

The goal is not predicting every recession.

The goal is making it through the economic environment.

That means having something outside of the market that benefits when the economy changes.

If interest rates go lower.

Who benefits from that?

And am I invested in it?

05/30/2026

Economics is always interesting.

There is never an economic situation where everyone loses.

And there is never an economic situation where everyone wins.

That means our job is to find the winning position.

And take advantage of it.

Think about the COVID recession.

Where would have been a horrible place to be invested.

Movie theaters.

Theme parks.

They were closed.

Now think about where the winning positions were.

Healthcare.

Anyone making COVID vaccines.

Masks.

Hand sanitizer.

Ventilators.

There was an economic winning position.

And there was an economic disadvantaged position.

That is why I spend so much time talking about asset allocation.

Because if the market is crashing.

We should already have positioned ourselves for different economic environments.

That is why the three buckets work.

The goal is not predicting the future.

The goal is being prepared for it.

05/27/2026

The moderate bucket is your middle bucket.

And the goal of this bucket is income.

Normally, this bucket holds between three to eight years of living expenses.

The goal is not being aggressive.

The goal is keeping up with inflation.

So we are usually targeting somewhere around a 3 to 5 percent return.

This bucket may include Treasury Inflation Protected Securities.

Investment grade bonds.

Or other income focused investments.

Bonds work a lot like a mortgage or a car payment.

You loan money to a business or the government.

And they promise to pay you back with interest.

But the important part is this.

We are not chasing the highest interest rate possible.

Because higher interest usually means higher risk.

Just like someone with a lower credit score pays higher interest rates.

A risky company has to offer higher returns to attract investors.

That is not the goal of the moderate bucket.

The goal is stability.

The goal is income.

And the goal is helping retirement keep up with inflation.

Real quick.

If you are 45 or older, I created a free Tax Smart Retirement Stage Assessment.

It tells you which of the seven stages you are in and what to focus on next.

Take it at obsidianwisdom.com/assessment.

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Fleming Island, FL
32003

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