Cinder Wealth Advisors

08/24/2026

Employees get a fairly steady paycheck, which makes their tax picture predictable and their Roth conversion math relatively flat year to year. Business owners live in a different world, and it hands them an opportunity most never notice.

Your income moves with the business. A great year and a slow year can look nothing alike. And occasionally there is a genuine gap, the stretch after you sell or wind down one thing and before income from the next one starts coming in.

That gap is one of the best Roth conversion windows I see in this work. Your taxable income can fall dramatically below your normal, which means converting money into a Roth costs far less than it would in a typical year. Same conversion, same account, much smaller tax bill, entirely because of when it happened.

Here is the version that sticks with me. Two owners sell in the same year. The first reinvests immediately and never really has a low-income year, so the window never opens. The second takes real time before the next venture and gets a stretch where a conversion is cheaper than at almost any other point in their life. Nothing about their wealth is different. Only the timing.

The catch is that these windows are quiet. They do not announce themselves, and if you are not watching for them, they close before anyone notices.

If you have a transition coming, or you are in one now, it is worth knowing whether a window is open.

08/20/2026

Here is a way to think about your traditional IRA or 401(k) that changes how people plan. Every dollar in that account has a tax bill attached to it that has not been paid yet.

That is not a scare tactic. It is just how pre-tax accounts work. You deferred the tax when the money went in, which means the tax is still owed. It has not gone away. It is waiting.

And it does get paid. The only real questions are when, at what rate, and by whom. Pay it yourself during your lifetime, or leave it for whoever inherits the account to pay at whatever rates exist then, on top of their own income.

This is what a Roth conversion actually does. It does not eliminate taxes, and anyone who pitches it that way is selling you something. It moves the tax to a moment you choose, at a rate you can see today, rather than a rate your future self or your family will simply be handed.

For business owners, whose income swings from year to year, that ability to pick the timing is a real advantage. The bill is not optional. But when you pay it can be, and that choice is worth a lot.

If nobody has shown you the unpaid liability sitting inside your retirement accounts, it is worth a look.

08/19/2026

For years, the case for a Roth conversion came with a countdown. Do it before 2026, because tax rates were scheduled to rise. That deadline is gone.

The law that was going to raise those rates got rewritten. Under current law, the lower rates no longer expire on schedule. No sunset, no automatic jump.

I have had clients bring this up almost sheepishly, like they let a window close on them. They did not.

Here is the part worth sitting with: if a deadline was the whole reason to convert, it was never a very good reason. The real case for a Roth conversion has nothing to do with a date on a calendar and everything to do with your own income, your bracket, and where you expect both to go.

The urgency disappeared. The strategy did not. Those are two different things, and the deadline was only ever the weaker of the two.

If your only reason to consider a conversion was the 2026 cliff, it might be worth understanding the reason that actually holds up.

08/13/2026

Some financial problems happen because someone made a mistake. This one happens because of how the responsibilities are divided, which makes it far easier to miss and a lot more common than it should be.

There is a required filing tied to certain retirement plans. When it gets missed, it is almost never because someone dropped the ball. It is because no one was holding it in the first place.

Watch how the assumptions line up. Your CPA figures your plan administrator is tracking it. Your plan administrator figures it is already being handled somewhere else. Both are acting in good faith, and both are looking right past it.

The reason is that it does not cleanly belong to either of them. Your CPA prepares tax returns, and this is not a tax return. It is a separate retirement plan filing. Whoever administers your plan manages the plan documents and testing, but this particular form is not necessarily part of that scope. So it sits in the space between two professionals you would assume were both watching, until a letter from the IRS makes it everyone's problem at once.

There is a structural reason the gap exists. A company 401(k) with employees falls under ERISA, and ERISA brings a whole apparatus of oversight with it. A recordkeeper, a third-party administrator, sometimes an independent auditor. Layers of people whose job is to catch exactly this. A one-participant plan is generally exempt from most of that structure. The deduction and the simplicity are the upside. The missing safety net is the tradeoff, and most owners never hear about the second half.

This is what I mean when I talk about coordination being the real work. The individual pieces were handled. What was missing was one person making sure they connected.

If you have a solo plan and you are not certain who owns this filing, the answer might be no one. Worth confirming.

08/10/2026

There is a retirement plan filing a lot of business owners do not know exists until they get a letter about it. And that letter is the expensive way to find out.

Once a plan's assets cross a certain threshold, an annual filing is required. Miss it, and the penalty accrues daily. It adds up to real money quickly, and most owners have no idea the clock is even running because they assumed the plan administrator was handling it.

Here is the part worth knowing. There is a voluntary correction program for exactly this situation. If you come forward on your own, file the missing forms, and resolve it before the IRS identifies the problem, you can generally settle for a flat fee per late return with a cap per plan. That is a fraction of the full penalty. But the door on those favorable terms tends to close once the IRS gets there first.

Which means the entire thing usually comes down to one phone call.

Call whoever administers your plan and ask two specific questions. Did your combined plan assets cross the filing threshold last year, and was the required filing actually made. Do not accept "it should have been." Get it confirmed in writing.

This is one of those quiet issues where the difference between catching it yourself and getting caught is enormous, and the only thing standing between the two is a five-minute conversation nobody thought to have.

If you are not certain your filings are current, that is worth confirming this week.

08/07/2026

Your tax return can be perfectly filed while a completely separate retirement-plan filing is overdue.

That is what makes Form 5500-EZ dangerous.

Normal market growth can push a one-participant plan across the filing threshold without a new contribution or any obvious warning.

If you own a solo 401(k), ask one direct question:

Was Form 5500-EZ required, and was it filed?

08/06/2026

Business owners with a solo 401(k), an owner-only cash balance plan, or both: this week’s newsletter is for you.

Form 5500-EZ is separate from your income tax return. Depending on how your advisors’ responsibilities are divided, it can be easy for everyone to assume someone else handled it.

If the form was required and missed, the IRS can assess penalties of $250 a day, up to $150,000 for one plan year.

In the video, I explain the $250,000 year-end asset rule, why separate plan balances may need to be combined, and three questions to ask now.

Watch it here before assuming the filing is covered

If you have a solo 401(k) or a cash balance plan that covers only y...

08/03/2026

Most S-Corp owners have been told the same thing. Keep your W-2 wage as low as you can defend and take the rest in distributions. It saves on payroll tax and the math looks clean.

That advice ignores what else your wage controls.

That number sets your future Social Security benefit. It also determines how much you are allowed to contribute to a real retirement plan. Not how much you want to contribute. How much you are permitted to.

Here is what that looks like in practice. A $60,000 wage gets you a limited 401(k) and very little room in a cash balance plan. Take the same business, set the wage appropriately, and those contribution limits climb dramatically. I have clients putting away $200,000, $400,000, and in some cases $600,000 a year. Not because their businesses are different. Because their wage was set with retirement funding in mind instead of payroll tax alone.

The savings from a low salary are real, but they are annual and modest. The cost is compounding and permanent. Every year you cap your own contribution room is a year of tax-deferred growth you never get back.

I am not telling anyone to inflate their salary to chase a bigger number. That creates its own problems, and the wage still has to be reasonable for the work performed. There is a thoughtful range, and where you land inside it depends on your profit, your goals, and what kind of plan you are actually trying to fund.

The part that matters most: this decision usually gets made by the CPA in isolation, optimizing for the tax return, with nobody asking what it does to the retirement plan. Those two conversations need to happen in the same room.

If your salary was set years ago and nobody has revisited it, that is worth a look.

07/30/2026

Social Security planning for business owners begins before retirement.

One decision involves compensation and retirement-plan funding while you are still running the company. The other involves when to claim benefits and how that choice fits your retirement income and family plans.

Those decisions require separate analysis.

Watch the full video for Matt’s breakdown of both conversations and when each one matters.
https://youtube.com/shorts/Bchw8kHgq68?feature=share

07/29/2026

Nearly every piece of Social Security advice says the same thing. Wait until seventy. Get the biggest check. For one of my wealthiest clients, I told him to do the opposite, and I would make the same call again.

Here is the reasoning. He did not need the money. His portfolio already covered every dollar he and his wife could realistically spend. So the usual question, how do I maximize my monthly benefit, was never really the right one for him. Waiting would not have built anything. It would have delayed income he was going to turn around and reinvest anyway.

So we claimed as early as he was eligible and accepted the smaller check on purpose. The difference is what we did with it. Every payment went straight into the market, invested the same way you would steadily buy in over time, rather than spent. Each check stopped being income and became a deposit.

For him, the objective was never the largest possible benefit. It was the largest possible legacy. And every year he claims early is another year those dollars are compounding for his family instead of waiting to be collected down the road.

I want to be clear about something, because this is where people get into trouble. This is not general advice. For most retirees who need the income, waiting is still the stronger move, and claiming early would be a mistake. This worked because of his specific situation, his resources, and his goals. Change those inputs and the answer flips entirely.

That is the whole point. The right strategy is never the one that sounds right in a headline. It is the one that fits the actual person in front of you.

If your plan has only ever been run through the standard playbook, it might be worth a closer look.

Book a Tax Strategy Review: https://app.greminders.com/c/mattlosanno/tax-strategy-review