Lawless Capital Group LLC

05/18/2026

This is a good reminder that Roth conversions are not automatically good or bad.

Lately, the term gets thrown around like it is some universal retirement “hack,” but the reality is that a Roth conversion is simply a tool. Whether it helps or hurts depends entirely on the context of the overall plan.

The goal is not just to convert money to Roth because someone on the internet said taxes are going up. The goal is to understand whether the strategy actually improves your long term after tax net worth and creates a better outcome for your specific situation.

A conversion can impact your tax bracket, Social Security taxation, Medicare premiums, future RMDs, cash flow, and even legacy planning decisions.

Without understanding the rules and how the strategy fits into the bigger picture, there is no way to know whether it is actually the right move.

That is why I believe retirement planning works best when decisions are made as part of a coordinated strategy rather than reacting to headlines, opinions, or one-size-fits-all advice.

Sometimes a Roth conversion isn't right for you — or at least not right now. A financial adviser explains what you should consider before getting involved.

05/06/2026

“Delay Social Security if you can afford to.”

A lot of financial advisors say this.

And sometimes it’s good advice.

But the reality is a lot more complicated than that.

First, the breakeven math is usually oversimplified.

You’ll hear:
“You need to live until 80 for delaying to make sense.”

That ignores the Time Value of Money.

When you factor that in, breakeven is often much closer to your mid 80s.

Second, it ignores taxes.

Most retirees are pulling income from pre tax accounts like a 401(k).

That money is fully taxable.

Social Security is only partially taxable.

So what are you really doing?

In many cases, you’re replacing a more tax efficient income stream with a fully taxable one.

And here’s the part almost nobody talks about…

To delay Social Security, you still need income.

So you spend down your most flexible dollars first.

The money you can control.
The money you can plan around.

To delay an income stream you can’t control.

That doesn’t make delaying wrong.

It just means the decision is bigger than “take it early or late.”

It’s about:
• Where income comes from
• How it’s taxed
• How everything fits together over time

There are absolutely situations where delaying makes sense.

But if no one has shown you how it fits into your full plan…

You’re probably not making a strategy decision.

You’re following a rule of thumb.

Learn the rules and strategies that might be able to help boost your benefits.

04/30/2026

You wouldn’t ask a contractor why he owns a hammer or a screw gun.

They’re just tools.

What matters is what they are building… and how those tools are used to get there.

Financial products work the same way.

Annuities, 401(k)s, IRAs, life insurance… they’re not the plan.

They’re tools inside the plan.

The issue we see most often isn’t the product itself... it’s that no one ever showed how it all fits together.

That’s exactly what this post is about.

04/30/2026

The “safe” part of your portfolio… might not be safe.

Everyone is watching the Fed and waiting for rate cuts.

But right now… that’s uncertain.

And that matters more than people think.

Because bonds — where most people keep their conservative money — depend on interest rates.

That’s also where most people plan to generate cash for withdrawals in retirement.

So if rates are uncertain…

👉 bond markets become uncertain.

And that’s a problem.

Because that’s the money you’re relying on when the paycheck stops.

Not your growth portfolio.

This is where sequence risk can show up.

Not because the market crashes…

But because the “safe” money isn’t stable when you need it to be.

That’s how portfolios get hurt.

The Federal Reserve held its benchmark interest rate steady on Wednesday afternoon amid uncertainty over when the conflict in the Middle East will be resolved.

04/23/2026

The market has had a lot of movement lately.

We saw a pullback earlier this year… and now the S&P 500 is back near its highs.

Every time that happens, the same question comes up…
“Should I be doing something right now?”

The reality is, if changes were made based on emotion during that downturn,
you’re likely behind where you would be today.

That’s not a market issue…
that’s a planning issue.

When things are set up the right way, you already know:
• where your income is coming from
• how withdrawals are handled
• what happens if the market drops

That’s the difference between having investments…
and having a plan.

If you’re not sure how your situation would hold up, it’s worth taking a look.

– Brett Lawless
Lawless Capital Group

04/08/2026

Last week we were up in Minnesota hosting federal retirement seminars with US FEDS.

And one thing continues to stand out in every room…

These are people who have done the right things.

They’ve worked hard for decades.
They’ve saved.
They have benefits most people would be grateful to have.

But when it comes time to actually make decisions…

There’s still a lot of uncertainty.

When can I retire?
What will my income actually look like?
How do taxes factor into all of this?

Because federal retirement isn’t simple.

It’s not just a pension decision.
It’s not just Social Security.
It’s not just TSP.

It’s how all of those pieces work together.

And more importantly… when and how you use them.

That’s where most people get stuck.

Not because they didn’t prepare…

But because nobody ever showed them how to bring it all together into a real plan.

Appreciate everyone who came out last week. Looking forward to the next one.

04/08/2026

What Matters Right Now:

The biggest risk in retirement isn’t the market.

It’s needing income from it at the wrong time.

If you’re pulling money during a downturn, it can permanently damage a portfolio.

That’s called sequence of returns risk.

And it’s why retirement isn’t about having investments.

It’s about having an income plan.

Because if your income is tied to volatile funds or dividends that change month to month, your income isn’t stable.

Which means your decisions won’t be either.

You start questioning everything.

What you can spend
What you should do
Whether you’re actually okay

Retirement shouldn’t feel like that.

It should feel clear.

Not because everything is guaranteed…

But because you know where your income is coming from and when.

Built around your life.

Not a rule of thumb. Not someone else’s strategy.

As markets turn volatile, recent retirees and people on the cusp of retirement are uniquely vulnerable. If you’re concerned, here is what you should know.

04/06/2026

In our office, we constantly get asked:

“What number do I need to retire?”

The number always changes.

But the process doesn’t.

Because retirement isn’t about a number.

It’s about knowing:
What income you actually need
Where that income is coming from
And how taxes impact every decision along the way

Two people can have the same amount saved and end up in completely different positions.

That’s why we focus on building a plan around the person…

Not chasing a number from a headline.

Nearly half of Americans think it’s somewhat or very likely they will outlive their savings.

03/27/2026

We came across an interesting perspective this week.

The article highlights how uncertainty around Social Security, taxes, and healthcare is causing many people to delay financial decisions.

That aligns closely with what we see in conversations with clients.

Most people are not focused on day-to-day market movement or a specific investment.

They are trying to answer questions like:

When can I actually retire?
What will my income look like?
How do taxes factor into the bigger picture?

Uncertainty will always exist.

The real challenge is not having a clear understanding of how everything works together.

When income, taxes, and assets are viewed as part of a coordinated plan, decisions tend to become much clearer.

Workers and retirees are anxious when faced with unpredictable policies.

11/05/2025

It was great to be back in Minneapolis meeting with federal employees over the past few weeks. With the government shutdown, there have been more questions than ever... and it’s always rewarding to help lay out the options clearly so families can make confident decisions.

Looking forward to heading back this spring!

10/10/2025

Welcome to Lawless Capital Group — where financial clarity meets independence.
Our mission is simple: help families, federal employees, and business owners create lasting financial freedom through thoughtful planning, disciplined investing, and smart tax strategy.

We’re excited to share what we do, why we do it, and how it can help you live life on your terms.