Writing

150 published LinkedIn feed entries through November 2, 2026.

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Would you give up the capital gains rate on part of a gain to deduct your interest this year?

November 2, 2026David Rosen

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An opportunity zone fund can remain illiquid when tax on the client’s original deferred gain becomes payable. A client who invested all available cash…

November 2, 2026David Rosen

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The replacement property is available, but the property you plan to sell is still on the market.

November 1, 2026David Rosen

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Bloomberg reports that the office-property slump is producing losses for investors in commercial mortgage-backed securities, the investments backed by…

November 1, 2026David Rosen

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Estate values may fall after someone dies.

October 31, 2026David Rosen

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The term “family office” is often muddled in today’s professional and investment communities. Many families hold investment assets through holding…

October 31, 2026David Rosen

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A real-estate loan workout can leave you with a tax bill even when you receive no cash.

October 30, 2026David Rosen

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One spouse can earn the family’s salary while the other works in real estate. Yet, the rental losses on their joint return may still be passive.

October 30, 2026David Rosen

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Opportunity zones are one of my favorite topics. The rules changed, so we added the new rules from the OBBBA to our next book.

October 30, 2026David Rosen

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Charging any interest on a loan to a private foundation is self-dealing if you are a substantial contributor or another disqualified person. A low rate or…

October 29, 2026David Rosen

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Most families spend years educating children on how to be productive members of society. Few spend time educating them on how to own the family's actual…

October 29, 2026David Rosen

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If the family does not want to maintain the complex wealth system, what does the simplified alternative look like?

October 29, 2026David Rosen

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A gift of 20% of your business may use more of your exemption than you expected if the IRS increases its value.

October 28, 2026David Rosen

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You buy a commercial property for $4 million. How much can you deduct this year? How much will that deduction reduce your tax?

October 28, 2026David Rosen

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Every family defines their own family office. They turn it into their own business.

October 28, 2026David Rosen

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You can retain a priority return from a family partnership while transferring its future upside. But the preferred return has to be supportable, and the…

October 27, 2026David Rosen

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Senator Wyden wants to tax the investments inside private placement life insurance as though the policy were not there. For the families that use it, that…

October 27, 2026David Rosen

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There is a gap between what the family thinks it owns and what it actually owns.

October 27, 2026David Rosen

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You can contribute property to a partnership and still trigger a taxable sale when cash comes back to you.

October 26, 2026David Rosen

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A few years ago a client asked whether he should give an $18 million partnership interest to charity. The gift would have cost him $2.7 million in tax.

October 26, 2026David Rosen

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WHAT WILL OUR CHILDREN END UP WITH AFTER DEATH?

October 26, 2026David Rosen

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Your family foundation's annual payout is based on its assets, not just the cash it earns.

October 25, 2026David Rosen

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Washington became an income-tax state this year. The people who built businesses there because it was not one now have a decision to make.

October 25, 2026David Rosen

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When an S corporation owner leaves, who buys the shares matters.

October 24, 2026David Rosen

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What we create today, we restructure tomorrow.

October 24, 2026David Rosen

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Your business income may qualify for a deduction of up to 20%. But the type of income and your total taxable income can change how much you receive.

October 23, 2026David Rosen

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PPLI is the perfect asset - if you are looking at tax consequences. Life insurance is the only asset that can make the following claims: it grows…

October 23, 2026David Rosen

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The family that would not sell when it could choose the timing ends up selling when the timing chooses them.

October 23, 2026David Rosen

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An irrevocable trust may have outdated provisions even when the family still wants the assets to remain in trust.

October 22, 2026David Rosen

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We should be able to price the cost of complexity directly. The family already pays every component. It just never sees them added up.

October 22, 2026David Rosen

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A family that will not simplify has to manage. A family that will not manage should simplify.

October 22, 2026David Rosen

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My webinar with Family Business Magazine is tomorrow, October 22.

October 21, 2026David Rosen

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Your business may be able to pay state income tax and deduct it before the income reaches your return.

October 21, 2026David Rosen

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A business can borrow money and distribute the cash to its owners, with very different tax consequences depending on whether it is a partnership or an S…

October 21, 2026David Rosen

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Get the after-tax proceeds calculation before you become attached to the price.

October 21, 2026David Rosen

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Your foundation may be able to keep only 2% of the family business, even if you give it much more.

October 20, 2026David Rosen

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The IRS is seeking about $736 million in gift tax and penalties from the Elcan family, which used GRATs to transfer wealth to its children.

October 20, 2026David Rosen

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Taxes, relationships and skills all influence how long we hold assets. Selling also requires a plan for the proceeds and the willingness to do the work.

October 20, 2026David Rosen

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A trust for your children and grandchildren may need a separate plan for generation-skipping transfer tax. The gift-tax return, trust terms and timing of…

October 19, 2026David Rosen

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How you structure an Opportunity Zone investment can give you more time to put the money to work.

October 19, 2026David Rosen

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Beyond the tax consequences covered in the first post, there is a human element that does not appear in any financial model.

October 19, 2026David Rosen

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Selling an interest in an LLC taxed as a partnership does not necessarily produce only capital gain.

October 18, 2026David Rosen

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If you haven't left California yet, it's probably too late (for tax purposes).

October 18, 2026David Rosen

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A real estate business may be able to deduct more interest by making a tax election. But the cost can be slower depreciation on the property.

October 17, 2026David Rosen

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Saturday is tax day - here is one of my favorite articles.

October 17, 2026David Rosen

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An estate tax bill can create pressure to sell a family business. Some estates can spread the business portion of that tax over time, but the payment plan…

October 16, 2026David Rosen

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Family offices and wealthy families with trusts have to deal with a second taxpayer with its own rules - how are fees deductible for trusts?

October 16, 2026David Rosen

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People fight over schedules more than distributions.

October 16, 2026David Rosen

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One partner wants cash from a real estate sale. The others want to reinvest through a section 1031 exchange. Taking the cash inside the partnership can…

October 15, 2026David Rosen

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Does the founder's wealth personality impact your family office?

October 15, 2026David Rosen

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Why don't people sell assets? Why do they hold them instead of selling them? The main reason people select investments is economic; they believe those…

October 15, 2026David Rosen

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A private foundation may be able to pay a professional-services fee to a family office while being prohibited from paying that office $1 in rent. What the…

October 14, 2026David Rosen

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How can a wealthy family loan money to family members and grow investment assets outside of their estate? What about loans for other purposes?

October 14, 2026David Rosen

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A large tax bill does not make every proposed tax investment a good investment.

October 14, 2026David Rosen

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Leaving S corporation shares in trust takes more than naming the beneficiaries. The wrong ownership structure or a missed election can put the company's S…

October 13, 2026David Rosen

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A donor advised fund is an unusual concept - it was created to avoid long-term charitable arrangements that avoided the self-dealing rules. The approach…

October 13, 2026David Rosen

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When you need someone for a job, you put out a search and find the best employee. But in family planning, we are delivering the assets to designated…

October 13, 2026David Rosen

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A gift to a SLAT can allow distributions to your wife during her lifetime, subject to health, education, maintenance and support (HEMS) under the…

October 12, 2026David Rosen

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Giving art to charity? You cannot just give it away to any charity. You have to give it away to the right one.

October 12, 2026David Rosen

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Wealthy families run headfirst into accounting, tax and legal challenges as their wealth grows.

October 12, 2026David Rosen

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Two partners can own a property equally, receive the same cash and report different amounts of taxable income.

October 11, 2026David Rosen

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For forty years, leaving New York was a tax strategy. Starting this year, those that left become a new tax base.

October 11, 2026David Rosen

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An appreciated asset can provide fixed payments during your lifetime or for a term, with a gift to charity afterward.

October 10, 2026David Rosen

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Family goals, financial goals and social goals. The family office framework describes how to think about a multigenerational family:

October 10, 2026David Rosen

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An investment loss can reduce taxes on gains elsewhere in your portfolio, or from a business sale.

October 9, 2026David Rosen

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A C corporation holding investments can owe a 20% personal holding company tax in addition to its regular corporate income tax. I do not come across…

October 9, 2026David Rosen

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Good estate planning is sometimes bad income tax planning.

October 9, 2026David Rosen

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A renovation budget that fails the usual Opportunity Zone test may work for a qualifying rural property.

October 8, 2026David Rosen

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Why do so many family offices use a complicated carried interest structure?

October 8, 2026David Rosen

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Complex assets do not always have an obvious exit.

October 8, 2026David Rosen

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Keeping equity when you sell your business may defer part of the gain, but it does not erase the tax.

October 7, 2026David Rosen

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Will your short-term rental losses offset your other income?

October 7, 2026David Rosen

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Opportunity zones are one of my favorite topics.

October 7, 2026David Rosen

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Selling a $5 million business interest to a grantor trust does not remove $5 million from your estate. You have exchanged the business interest for a $5…

October 6, 2026David Rosen

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Article introduction

The Buyer Wants Assets. Who Owns the Goodwill?

October 6, 2026David Rosen

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Complexity does not arrive all at once. It accumulates in layers, each one added for a perfectly rational reason at the time, and together they create a…

October 6, 2026David Rosen

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How does the US economic and tax system effect what you leave to your children?

October 5, 2026David Rosen

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What is your domicile? What is your legal home? Is it that easy to move to Florida or Texas and state taxes?

October 5, 2026David Rosen

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Your S corporation can lose money without giving you a current tax deduction.

October 5, 2026David Rosen

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You can sell a property for $3 million, buy another for $3 million and still recognize $300,000 of gain in a section 1031 exchange.

October 4, 2026David Rosen

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The IRS wants to know why the losses are ordinary and the gains are capital.

October 4, 2026David Rosen

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A family office can exist for years before anyone calls it one.

October 3, 2026David Rosen

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Start with the giving plan, not the name of the vehicle.

October 3, 2026David Rosen

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Watch our Mobena demo from FinovateFall 2026.

October 2, 2026David Rosen

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The installment sale is not something you elect into. It applies automatically, if the sale qualifies. This post on installment sale rules just covers the…

October 2, 2026David Rosen

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A $2.5 million basis increase can include a basis reduction.

October 2, 2026David Rosen

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We created the entities, made the elections, and drafted the trusts. Do families understand their complex world? Do we understand what we are creating for…

October 1, 2026David Rosen

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The agreement exists and the allocation is never run.

October 1, 2026David Rosen

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A gift can save estate tax and still cost your family more tax.

October 1, 2026David Rosen

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Most wealth planning begins with an unspoken objective - maximize the family's after-tax wealth.

September 30, 2026David Rosen

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A stock sale can produce millions of dollars of tax-free gain. And you don't have to do anything but choose the right structure. That is the power of…

September 30, 2026David Rosen

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The partnership borrowed the money. That does not make all the interest deductible.

September 30, 2026David Rosen

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It is very hard to be wealthy in today's world. A wealthy family cannot buy freedom from complexity.

September 29, 2026David Rosen

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Article introduction

Your Opportunity Zone Bill Comes Due December 31

September 29, 2026David Rosen

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Deferring $1 million in a qualified opportunity fund does not necessarily mean recognizing $1 million in 2026.

September 29, 2026David Rosen

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Most wealth planning begins with an unspoken objective - maximize the family's after-tax wealth. We pursue it with tax-efficient structures, long holding…

September 28, 2026David Rosen

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The tax you deferred when you invested in qualified opportunity zones is due soon. Do you have cash for your tax bill?

September 28, 2026David Rosen

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A $32.9 million trading year with hundreds of trades was not enough to be considered a trader.

September 28, 2026David Rosen

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Cash from an S corporation can be treated as tax-free basis recovery, dividend income or capital gain. Distributions in excess of basis are taxable, and…

September 27, 2026David Rosen

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The corporate tax rate is only part of the story when a C corporation is involved. How you take money out, what you leave in the business and how you…

September 26, 2026David Rosen

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A grantor trust that is excluded from the taxable estate is one of the most powerful estate planning tools in the planner's arsenal. Paying the trust’s…

September 25, 2026David Rosen

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Today's Daily Tax Planning Strategy explains cost segregation planning.

September 24, 2026David Rosen

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A trust is a different kind of owner.

September 24, 2026David Rosen

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A high-income year may be an opportunity to claim a deduction now for charitable payments made over time.

September 23, 2026David Rosen

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Today's Daily Tax Planning Strategy explains private placement life insurance planning.

September 22, 2026David Rosen

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Article introduction

Turning Ordinary Income into Capital Gain for Real Estate Developers

September 22, 2026David Rosen

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Are you ready for the tax from your qualified opportunity zone investments to come due this year? We show how the investor, fund and business can plan…

September 21, 2026David Rosen

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A loss on your tax return does not always mean a deduction you can use. We look at funding, financing and activity grouping that may help release…

September 20, 2026David Rosen

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Today's Daily Tax Planning Strategy explains planning partnership distributions of property.

September 19, 2026David Rosen

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Today's Daily Tax Planning Strategy explains state tax planning before selling a business.

September 18, 2026David Rosen

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Today's Daily Tax Planning Strategy looks at deducting family-office expenses.

September 17, 2026David Rosen

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Before your family buys the airplane, put the tax savings to the test.

September 17, 2026David Rosen

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Today's Daily Tax Planning Strategy looks at planning for the 2026 Opportunity Zone tax bill. This is one of my favorite topics - and one we discuss at…

September 16, 2026David Rosen

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Article introduction

No Benefit At All: When Charitable Contribution Deductions Don’t Save Tax

September 15, 2026David Rosen

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Today's Daily Tax Planning Strategy explains charitable contributions of appreciated artwork.

September 15, 2026David Rosen

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Today's Daily Tax Planning Strategy explains how to preserve capital gain on appreciated land before development.

September 14, 2026David Rosen

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Today's Daily Tax Planning Strategy explains installment sales and how to plan when you sell now but get paid later.

September 13, 2026David Rosen

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Today's Daily Tax Planning Strategy looks at accumulated earnings tax.

September 12, 2026David Rosen

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Today's Daily Tax Planning Strategy explains how a testamentary charitable lead unitrust can add a family benefit to the charitable portion of your estate…

September 11, 2026David Rosen

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Today's Daily Tax Planning Strategy explains qualified small business stock, or QSBS. Eligible founders and investors may be able to exclude significant…

September 10, 2026David Rosen

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Document post

Every entity had a reason. Does the overall structure still make sense?

September 10, 2026David Rosen

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Today's Daily Tax Planning Strategy looks at tax planning for founders selling stock. Who owns the shares, how the deal is structured, and when you act…

September 9, 2026David Rosen

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Today's Daily Tax Planning Strategy tells you about state residency - how to plan before a move to Florida.

September 8, 2026David Rosen

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Article introduction

PPLI: The Only Asset Without a (Tax) Tradeoff

September 8, 2026David Rosen

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In honor of Labor Day, today's Daily Tax Planning Strategy is on employee compensation and benefit planning.

September 7, 2026David Rosen

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Today's Daily Tax Planning Strategy features the the 65-day election for trust and estate distributions.

September 6, 2026David Rosen

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Today's Daily Tax Planning Strategy: short-term rental losses and material participation.

September 5, 2026David Rosen

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Here is your Daily Tax Planning Strategy.

September 4, 2026David Rosen

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Most families never put real return expectations on the people investing their money. The relationship just has to stay good enough.

September 3, 2026David Rosen

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Article introduction

Kicking the (Tax) Can Into a Corporation

September 1, 2026David Rosen

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Repost with commentary

Mobena is looking for a Founding GTM Person to join as the company continues to grow.

September 1, 2026David Rosen

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The documents provided that when the first brother dies, he is replaced by no one. When the second dies, no one. The survivor governs a family office…

August 27, 2026David Rosen

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Three brothers control a family office worth hundreds of millions. When the first dies, he is replaced by no one. When the second dies, no one. Last man…

August 27, 2026David Rosen

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Article introduction

The Year We Paid the Tax on Purpose

August 25, 2026David Rosen

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The family that came to us had over three hundred K-1s - and no structure at all.

August 20, 2026David Rosen

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Article introduction

Bought the houses, moved the kids, still paid the tax

August 18, 2026David Rosen

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What goes on behind the unmarked office doors inside of a family office? It's not so secret and it's probably not that exciting either - but these offices…

August 13, 2026David Rosen

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Article introduction

How a Gift to Charity Left My Client's Family $1.4 Million Ahead

August 11, 2026David Rosen

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When you are five years out from potentially selling your business, what planning should you be starting right now?

August 10, 2026David Rosen

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My new article with Jeffrey Rosen, CPA, CGMA, MBA : a framework for thinking about a wealthy family from every angle.

August 6, 2026David Rosen

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Article introduction

Millions Less in Tax Than They Expected

August 4, 2026David Rosen

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Article introduction

Opportunity Zone Planning for Family Businesses

August 1, 2026David Rosen

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Document post

There is no single definition of a family office. Everyone seems to have a different version. I wrote a really long my own for the Bloomberg Tax portfolio…

July 29, 2026David Rosen

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Do you take tax planning seriously enough? That is the subject of my latest article "Tax Planning Should be Your Business".

July 27, 2026David Rosen

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Many investors will not pay all of the tax when the bill from their investments in Qualified Opportunity Funds comes due at the end of this year. You may…

July 24, 2026David Rosen

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Document post

I am excited to be presenting at the Notre Dame Tax and Estate Planning Institute on October 30 in South Bend, IN. It is always tax planning season for…

July 21, 2026David Rosen

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Repost with commentary

I am excited that Mobena, the innovative tax planning platform for complex families, is now testing with family offices, tax professionals, RIAs and…

July 8, 2026David Rosen

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Repost

Pre-tax estimates with footnotes don't cut it anymore when planning for complex families.

July 2026 · day unconfirmedMobena

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We are excited to share the next chapter for RS&F, our team and our clients. As we continue our mission to create the premier UHNW and family office…

November 5, 2025David Rosen

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Check out my new "Book on Qualified Opportunity Zones", the most comprehensive guide to qualified opportunity zones issued to date.

July 15, 2019David Rosen

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