CWOs for Hire

08/27/2026

Could your investment portfolio generate a little more income without immediately selling the stocks you own?

One strategy worth understanding is a covered call.

The basic idea is relatively simple: you own a stock, sell a call option against it, and receive a premium.

Sell options when stocks are flat or up — not simply because a stock is down.

If you've ever wondered whether covered calls could play a role in your retirement income strategy, this episode is for you:

https://youtu.be/yigrFTJ4XMY

Listen to the full episode and let me know what you think!

08/25/2026

There are always two sides to an options trade:

1. one side is higher risk, higher reward

2. the other side is higher probability, lower return

"Never” and “always” are usually bad investing advice. Worth thinking about before you copy someone else’s strategy.

08/21/2026

Tax Fraud Is RARE.

But....

Here’s How to Protect Yourself:

https://youtu.be/-fQ4aoeC7G0

08/20/2026

I’m surprised by how many people never actually look at their completed tax return!

AI helps, but it shouldn’t replace your CPA.

But it can be another set of eyes.

When it comes to your taxes, trust—but verify.

08/18/2026

Could your tax return be wrong—and you not even know it?

One of the simplest things you can do?

Get a copy of your actual filed tax return.

Then go to IRS.gov and pull your tax transcript. You can compare the two to make sure what was filed with the IRS is actually what you expected.

And now, AI can even help you review the return, supporting documents, and transcript for inconsistencies.

You don’t have to be a tax expert to be vigilant.

Listen to this week’s episode of Retire with Peace to learn how:

https://youtu.be/-fQ4aoeC7G0

08/11/2026

One of the biggest mistakes I see in retirement planning:

Building a plan around ONE version of the future.

What if inflation is higher?

What if markets fall early in retirement?

What if taxes increase?

What if you spend more than expected?

What if you spend less?

What if something completely unexpected happens?

That’s where scenario planning becomes so valuable.

Instead of asking, “Will this plan work?”

I think a better question is:

“How does this plan hold up if the future looks different than we expect?”

The goal isn’t to predict the future.

It’s to build enough flexibility that you don’t have to.

That’s a big part of what I discuss in this week’s episode of Retire with Peace.

Because peace of mind doesn’t come from knowing exactly what will happen.

It comes from knowing you have options when it doesn’t:

What if retirement doesn’t go according to plan?What if inflation...

08/04/2026

Thinking about getting rid of an annuity?

Before you surrender it, there are a few things you need to understand.

1. The difference between an IRA annuity and a non-qualified annuity.

And perhaps most importantly: what benefits are you giving up?

2. An annuity might provide guarantees or income benefits that are valuable to you today—even if the annuity itself isn't something you would choose if you were building your portfolio from scratch.

3. The worst time to learn about surrender charges and tax consequences is after you've already made the decision.

I break down what to consider before moving or surrendering an annuity in this week's episode of Retire with Peace:

https://youtu.be/0dc5LP9aOJY

What questions would you want answered before deciding whether to keep or surrender an annuity?

07/31/2026

Financial Tip Friday 💡

Depreciation is one of the biggest tax advantages of owning rental real estate.

Before you sell, make sure you understand:

• Your adjusted basis

• How much depreciation you've claimed

• Potential depreciation recapture

• Capital gains taxes

• Whether a 1031 exchange could help defer taxes

If the property is held until death and inherited, the step-up in basis may significantly change the tax consequences for your heirs.

https://youtu.be/BDiGbPqLiTo

07/28/2026

One of the biggest tax benefits of owning rental real estate is depreciation.

But here's the part many investors don't think about:

**The tax benefit today can create a tax consequence tomorrow.**

Depreciation reduces your taxable income while you own the property.

But when you sell, some of that depreciation may be subject to recapture.

That's why a property that looks like a great investment on paper can produce a surprisingly large tax bill when you sell.

Before selling a rental property, consider:

→ How much depreciation have you claimed?
→ What is your adjusted basis?
→ How much capital gain could you have?
→ Could a 1031 exchange make sense?
→ What happens if you hold the property for life and it passes to your heirs?

The right strategy depends on your situation.

But one thing is certain:

**Don't wait until the property is under contract to start thinking about the taxes.**

Tax planning works best when you have options:

07/23/2026

The best retirement strategy isn't the one that's trending.

It's the one that's designed for your goals, taxes, investments, and lifestyle.

Too often people abandon a strategy that's working because someone else claims there's a better way.

A successful retirement isn't built by copying others.

It's built by following a plan that fits you.