Dre Griggs, Investment Advisor Representative with Obsidian Wisdom

Directions Website Contact the business

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

10/23/2026

Your business is doing very well.

It's generating more money.

But is your money being used efficiently?

If you have all your money in one business, there is a level of risk tied to that industry.

That leadership team.

Key man risk.

All of these things.

But if you're invested in the stock market, you can invest in hundreds of companies.

In dozens of industries.

Having a million dollars in a portfolio is different than having another million dollars inside your business.

Now, that doesn't mean you should always do that right away.

There is a point in time when growing your company is the best thing.

But when you're ready to start separating your time from your money...

That's when we start diversifying our income streams from the business.

Why not invest in real estate?

Why not invest in the stock market?

Why not invest in additional businesses you can acquire?

Because things do happen.

The world does change.

And things do get a little bit crazy very quickly.

10/23/2026

When the internet was created, it created jobs and it took away jobs.

When automation was created, it created jobs and it took away jobs.

And when AI is created, it's going to create jobs and it's going to take away jobs.

So are we positive that having all of our eggs in this one basket of our business is the best choice forward?

For me, I like the idea of diversifying our income streams.

Multiple streams of income.

Separating some of my streams from my business.

And we can take a very steady approach.

Just start taking some money out of the business.

That could be as simple as setting up retirement accounts.

Maybe a SEP.

Maybe a solo 401K.

Maybe a SIMPLE or traditional 401K.

You even have the option of setting up your own pension program inside your company.

So if something did happen to the business...

You've already created an additional stream of income.

Someone might say...

"I have a net worth in my business of $3 million. Can I retire?"

Yes, but we're gonna start taking some of the money from the business and using that to generate tax efficient retirement income.

Now you have something over here.

And you still have the business going.

10/23/2026

I remember when I first was retiring from corporate America.

I was looking at buying a business before I ended up opening Obsidian Wisdom.

And I came across someone selling a photo booth business for maybe $40,000.

He was gonna give me the relationships.

Show me how to do things.

But when I really started looking at it...

"You're just giving me a list of names and phone numbers."

"You're not actually giving me the relationship."

Most of the customers were people getting married.

Sweet sixteens.

Bar mitzvahs.

People having one time events.

It was very rare to have repeat customers.

So I decided I wasn't gonna buy the business.

I just bought a photo booth and started building those relationships myself.

And when it was time to let that business go...

I just let it go.

I didn't sell anything.

Because I hadn't built something that could live without me.

I went to every single event.

Those people knew me.

They knew the quality of my work.

But it was always me.

And that ended up taking away a lot of the value of that business.

10/22/2026

"I'm gonna sell the business. It's worth $2 million."

"I'm gonna be able to go into retirement, live off of that the rest of my life."

"It's gonna be fantastic. I'll send you a postcard."

And I'm like...

"Okay, I have some questions."

There's normally gonna be one of three choices when it comes to your business and retirement.

You can sell the business.

You can keep the business and separate it from your time.

Or you can transition the business over an extended period of time.

Maybe you sell it to a partner.

Maybe you sell it to your key employees.

Or maybe you sell it to all your employees.

The thought is...

"If you paid me over an extended period of time, five, 10, 20 years, maybe this funds my entire retirement."

Or at least it becomes one of my income streams.

I'm a big fan of multiple income streams.

So when it comes to your business and retirement, what makes the most sense for you?

10/16/2026

Your business is your number one asset.

It is a phenomenal asset.

Great job building it over the years.

It helps people, your family, your loved ones, and even strangers.

It is a beautiful thing, entrepreneurship.

But there's another side.

Because you're constantly reinvesting in your business, a lot of the times we don't end up with very much in our retirement accounts or investment accounts.

We don't have a diversification of our income.

We don't have multiple streams.

And 65% of self made millionaires have at least three streams of income.

So what if we start taking some of the income from the business and building other incomes?

Now the business becomes less important.

Not to say we don't wanna keep it.

Not to say we don't wanna sell it.

It just becomes less critical.

And as you purchase more and more of your time, you start looking at your business a little bit differently.

10/16/2026

For a lot of my clients, it's not that they don't wanna work at all.

They just wanna do something different.

Maybe they wanted to be a musician.

Maybe they wanted to be an educator.

But the salary wasn't enough.

They had to choose what put food on the table.

And I find that once you separate time from your money, that is when the dream starts.

But when I meet entrepreneurs, they have a number in mind.

What they expect the business to sell for.

Will that number be accurate?

We don't know.

We have to find someone willing to pay that price.

And Uncle Sam is waiting to tax us.

So how do I count my business income in my retirement plan?

All of these things come into consideration.

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.

Address

Fleming Island, FL
32003

Website

Alerts

Be the first to know and let us send you an email when Dre Griggs, Investment Advisor Representative with Obsidian Wisdom posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Contact The Business

Send a message to Dre Griggs, Investment Advisor Representative with Obsidian Wisdom:

Shortcuts

Share

Category