Dre Griggs, Investment Advisor Representative with Obsidian Wisdom

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

10/30/2026

As a business owner, your first thought might be, “As much as possible.” Or maybe, “Whatever keeps my taxes low.”

But I start with another question: What are you trying to accomplish?

Buying a home, saving for retirement and preparing to sell your business can each call for a different approach.

Your pay should reflect your goals, your business cash flow and the tax rules that apply to you.

Swipe through for the questions to ask before choosing your number.

As a business owner, your first thought might be, “As much as possible.” Or maybe, “Whatever keeps my taxes low.”But I s...
10/30/2026

As a business owner, your first thought might be, “As much as possible.” Or maybe, “Whatever keeps my taxes low.”

But I start with another question: What are you trying to accomplish?

Buying a home, saving for retirement and preparing to sell your business can each call for a different approach.

Your pay should reflect your goals, your business cash flow and the tax rules that apply to you.

Swipe through for the questions to ask before choosing your number.

10/30/2026

There are people that will do tactical rebalancing.

And I provide that for my clients as well.

The idea is simple.

I know what economic season we're in.

And I'm going to shift some of the portfolio to recognize that new climate.

Not all the way like I'm gambling.

Just some of the portfolio.

Think about high inflation.

When inflation is high, we expect the Fed to start raising interest rates to reduce inflation.

Who does that benefit?

Normally, banks.

Because they're the ones giving out the loans.

So maybe we add more banks to the portfolio.

But who does that hurt?

Probably real estate.

Because higher interest rates mean higher monthly payments.

You may not even be approved for that loan anymore.

And think about COVID.

It was a great time to be in healthcare because the government was paying them billions of dollars.

But it was a bad time for amusement parks and movie theaters.

Because they were closed.

There are different economic environments.

And the idea of tactical rebalancing is recognizing those different climates.

10/30/2026

At what point in time is having everything I own, everything I am, tied to the business a problem?

For me, when we're thinking about achieving financial freedom and separating our time from our money, we have to think about risk.

One of those risks is concentration risk.

If you went into the stock market and put all your money in one business, you'd recognize that's a very risky move.

There are so many businesses out there.

Why would you put everything in one?

Now, some people say being concentrated gives you the opportunity to make a higher return.

Which is true.

But when I build a diversified portfolio, I'm building it for a variety of economic climates.

During recessions, we look at things like utilities and consumer products.

Walmart.

Procter & Gamble.

Things you're gonna spend your money on even if you don't have a lot of it.

And then we think about industries that may struggle during recessions.

Luxury goods.

Cruises.

Jewelry.

But when we have economic growth, we look at opportunities in the tech industry.

Research and development.

Increasing productivity.

Because there are different economic climates.

And that's why I think about diversification when we're working toward financial freedom.

10/29/2026

What if you could limit your tax exposure without necessarily limiting your income?

That's what we do at Obsidian Wisdom.

We find ways for entrepreneurs to limit their taxable income.

Uncle Sam allows entrepreneurs to use different retirement accounts.

Solo 401Ks.

Traditional 401Ks.

SEP IRAs.

Even your own personal pension.

But here's where it gets interesting.

Depending on how you're going to use that income in crafting your retirement income, the answer can change.

If you want tax free income, there are limits on how much you can earn before you don't qualify for a Roth IRA.

But if you're trying to max out your solo 401K...

Those limits are tied to how much income you're generating.

So you may want to max out your income to contribute as much as possible.

Or you may want to limit your income to qualify for another retirement instrument.

It all depends on how you're going to use that income in crafting your retirement income.

10/28/2026

We're normally still thinking in a very linear perspective.

My paycheck is how much I receive.

But what if your money is working?

I'm someone who loves the idea of separating your time from your money through building multiple streams of income.

Because if we're playing the game right, your money is used to build multiple streams.

And that gives you the flexibility to make work optional.

Work optional in my business.

Where I can work on passion projects.

Work optional in business number one.

Because I want to start business number two.

Work optional with my real estate.

Because I want to take that money and start something on the side.

Or maybe you just wanna lay back in the shade and relax.

Then you can invest all of it in the stock market.

The idea is separating your time from your money.

Building multiple streams of income.

And giving yourself the flexibility to make work optional.

10/28/2026

I remember when I first entered the financial industry.

I was a credit manager at Wells Fargo.

Business owners would walk in and say...

"Hey, I have a business and I want to get a car loan."

I'd say, "Okay, cool. I'm gonna just need your last two pay stubs."

And they'd tell me...

"Well, I don't really pay myself. The business pays all of my bills."

Okay.

"Let's just use the last two years' tax returns."

And that's when they'd say...

"Oh, well, all of my tax returns, I write everything off, so I don't actually have any income on there either."

And I'd tell them...

"You have two choices available."

Start paying yourself a paycheck.

Or start claiming some of this income on your tax return.

We can't on paper say that we make no money and the business operates at a loss and then get approved for a loan.

So for me, the conversation almost always starts with one question.

What is the goal?

Is the goal to limit taxes?

Sell the business?

Get a loan to buy a new house, a new factory, or expand equipment?

The answer will adjust accordingly.

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.

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