Wealth management after selling a business, as Apollon Wealth Management does it, puts the proceeds, your IRAs and Medicare premiums on one deadline list for owners whose company was most of what they owned. You receive one page listing each decision from closing to your first RMD, with its date and estimated tax cost, updated at every progress meeting.
What does wealth management after selling a business cover once the wire arrives?
It covers four decisions after closing that carry a tax cost: the estimated tax on the gain, where the proceeds sit and how their income counts for Medicare, how much IRA money to convert before RMDs at 73, and who inherits the IRAs.
Owners whose company was most of their net worth, and who now hold cash for the first time, usually need it. One detail surprises widowed sellers: you file single, so the first Medicare surcharge starts above $109,000 of MAGI, not $218,000.
Same question, two answers: is now the time to convert the IRA?
Merle (a hypothetical client) is 68, widowed, and just sold the machine shop his father started. He holds $900,000 in IRAs, with RMDs at 73. His two daughters, one of whom works in the shop, would need to drain whatever IRA money they inherit within ten years of his death, possibly while they earn the most. His answer: yes, in measured amounts from 69 to 72, never in the sale year.
Latoya (also hypothetical) is 51, has about $550,000 in a solo 401(k), and asks the same thing while earnout payments are still arriving. Her answer: wait. Each payment lifts her income, she's under 59½, so the conversion's tax cost has to come from outside cash, and the college aid forms for her daughter count income too.
The rule of thumb behind both answers: a conversion saves tax only if the rate on the converted dollars today is lower than the rate when they would otherwise come out. Otherwise it just moves the same tax cost to an earlier year.
How long do a sale's tax effects keep showing up?
Estimated tax is due April 15, June 15, September 15 and January 15. If your prior-year AGI was over $150,000, the IRS safe harbor is paying 110 percent of last year's tax to avoid the underpayment penalty. A closing in the fourth quarter still needs a January 15 payment.
Medicare follows MAGI with a two-year lag, so the sale year shows up in your Part B bill two years later. A sale-year MAGI over $500,000 for a single filer means $689.90 a month for Part B instead of $202.90 in that later year, or $5,844 extra. A voluntary sale is generally not a listed life-changing event on Form SSA-44 (stopping work is), so an appeal rarely helps.
RMDs start at 73 (75 if you were born in 1960 or later). A Roth conversion can't be undone once it's done.
That's why Merle skips conversions in the sale year. His MAGI is already high, and a conversion can add the 3.8 percent net investment income tax on top of ordinary rates.
If you're 63 or older and the sale year is behind you, size each year's Roth conversion so MAGI stops at or just under an IRMAA threshold ($109,000 single, $218,000 joint for the standard Part B premium). The premium reflects that income two years later.
How much IRA money can Merle convert before 73 without a higher Part B?
Merle can convert about $49,000 a year for four years, $196,000 in all, and keep the standard Part B premium of $202.90 per month. That assumes the hypothetical $60,000 of other MAGI he has from 69 to 72. The Medicare figures are the 2026 CMS tiers.
Here is the arithmetic for a hypothetical person. Merle, 68, closes the sale for $2.5 million and keeps $900,000 in IRAs. Converting $49,000 a year holds MAGI at $109,000. Converting $111,000 a year moves $444,000 but lands at $171,000, where Part B is $405.80. That's $202.90 more per month: $2,434.80 a year and $9,739.20 across four years, before the income tax on the larger conversions.
We lean toward a middle pace, and it's a judgment call. At $77,000 a year, MAGI stops at $137,000, in the $284.10 tier. That's $974.40 more per year, $3,897.60 over four years, and it moves $308,000. It's worth it only if the daughters' future rates look higher than Merle's.
Timing trips people up. A conversion at 69 sets the premium at 71, and one at 72 sets it at 74. The plan counts the surcharge years, not the conversion years.
Careful sellers make one mistake: buying municipal bonds to keep the proceeds' income tax-free. Tax-exempt interest is added back into the MAGI Medicare uses. For Merle, $1.5 million yielding 3 percent, for illustration, is $45,000 per year, which takes him from $60,000 to $105,000 before any conversion. His planned $49,000 conversion then lands at $154,000, in the $405.80 tier, costing $2,434.80 a year more for Part B.
Roth balances and invested proceeds can lose value, and no return is certain.
The surcharge years, not the conversion years
The municipal bond trap
If you're widowed, past 63, or a few years from RMDs
Each of these makes the work worth doing now. Widowhood moves you to single brackets and single Medicare thresholds. From 63 on, the income you report this year decides what Medicare charges you at 65 and beyond, two years later. Between 69 and 72 you have the last window before RMDs at 73. And if your children are entering peak earning years, they'll pay more on the IRA money they inherit.
What a good answer sounds like when you ask a firm about the proceeds
Ask any firm, Apollon Wealth Management included, what happens in the first year after closing. A good answer names dates and dollar amounts: the January 15 estimated payment, a conversion sized to an IRMAA threshold, who updates the IRA beneficiary forms. A weak answer only describes a portfolio mix. Also ask where every fee is written down. Ours are all in the client agreement, and nothing outside it is charged.
Papers to bring to Apollon Wealth Management, and why each matters
The closing statement and the purchase price allocation (Form 8594 in an asset sale) show how much of the price is capital gain and how much is ordinary income. Your last two tax returns and Social Security's yearly premium letter set the estimated-tax safe harbor and show which Part B tier you're paying now.
IRA year-end statements and beneficiary forms size the conversions and RMDs and confirm who inherits. A brokerage statement showing tax-exempt interest matters too, because that interest counts in Medicare's MAGI.
Find the closing statement row first. Most items come from the deal attorney, the CPA or a custodian, not from your own files, so ask for them early. We meet by phone or video, and we work with clients who have $500K or more in investable assets.
One limit: if closing is still more than a year away, the bigger tax decisions (deal structure, price allocation, timing) belong to sale tax planning, and this work can wait. Nothing here picks investments sure to grow.
| Item | Why it matters | Where to find it |
|---|---|---|
| Closing statement | Gross price, escrow, holdbacks | Deal attorney at closing |
| Price allocation (Form 8594) | Splits ordinary and capital gain | Purchase agreement exhibit |
| Last two tax returns | Sets 110% safe harbor | Your CPA |
| Social Security premium letter | Shows current Part B tier | Mailed by Social Security yearly |
| IRA year-end statements | Sizes conversions before 73 | Each custodian |
| IRA beneficiary forms | Confirms who inherits | Custodian website or office |
A conversion at 69 sets the premium at 71. The plan counts the surcharge years, not the conversion years.
Your questions about wealth management after selling a business, answered
Municipal bonds or a taxable bond fund for sale proceeds: which leaves more after tax and Medicare premiums?
Neither wins automatically. Municipal interest escapes federal income tax but still counts in the MAGI Medicare uses, so it can push you into a higher Part B tier. Compare after-tax yield plus the premium cost for your own income. Bonds can also lose value, and returns are never certain.
Can I undo a Roth conversion if my income after the sale turns out higher than I planned?
No. A Roth conversion can't be undone once it's done, and the tax cost stays. That's why Apollon Wealth Management sizes conversions in measured amounts, one year at a time, after the sale year's income is known.
How much should I pay in estimated tax after closing the sale of my business?
Estimated payments are due April 15, June 15, September 15 and January 15. If your prior-year AGI was over $150,000, paying 110 percent of last year's tax avoids the IRS underpayment penalty. A fourth-quarter closing still needs the January 15 payment, so size it from your closing statement.
Do my daughters pay income tax on an IRA they inherit from me?
Yes, on a traditional IRA. Withdrawals are taxed as ordinary income to them, and most adult children must empty the account by the end of the tenth year after your death. Roth money they inherit generally comes out income-tax-free, which is why conversions matter.
What age do my required minimum distributions start if I was born in 1958?
Age 73. RMDs start at 73 for people born before 1960 and at 75 for anyone born in 1960 or later. Your custodian sends an RMD notice, but the withdrawal is your responsibility, so the dates go on the deadline list.
Will consulting income from the buyer reduce my Social Security benefits?
It can if you're under full retirement age, which is 67 for people born in 1960 or later. The SSA earnings test withholds benefits above $24,480 a year for 2026, or $65,160 in the year you reach full retirement age. Consulting pay also raises MAGI for Medicare.
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This content is general information only and does not constitute investment, tax or legal advice tailored to your circumstances. Investing involves risk, including possible loss of principal. Past performance is no guarantee of future results. Consult a qualified professional before making any financial or legal decision.