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Aaron.Bedrick

Finding Opportunities in Challenging Times: Leveraging Low Asset Values for Tax Planning



Challenging times in businesses may cause a lot of stress in the near term. However, there is a silver lining: the cornerstone of good planning is to take advantage of low asset values.


Think about tax loss harvesting - you sell stocks when they are down and buy them back, capturing the loss to offset other gains. You have benefited from a “down market.”


This concept carries over to estate and income tax planning for other types of assets as well.


There are 4 major struggles that I can think of in different industries that I deal with:


Merchant cash advance: the Yellowstone case has thrown the industry into panic mode



Home care: new legislation threatens to wipe out CDPAP in NY. This would erase many businesses entirely. 



Child Service advocacy: new legislation threatens to greatly reduce the margin for advocate firms. 



Multifamily real estate bought at low caps in the past few years has been reset to much higher cap rates, putting many syndicators underwater. 




All of these things, and likely many more out there, threaten the earning prospects of many businesses. 


This can be a good thing; if a business owner uses this high risk period to move their asset into a trust or other tax-advantaged vehicle at a low appraisal value, they can take home a massive tax win on a rebound in their business.


For example (I am ignoring IRS discounting in this example for those planning folks reading this): 


Home Care business A was projected to make $5M of EBITDA this year, and grow at 5% per year for the next 5 years. Let’s say the appraiser uses a 7x multiple and calls this a $35M business this year.


Now, EBITDA projections for 2025 have dropped to $2.5, and growth can’t be counted on any more. This business may be appraised for $17M. Perhaps lower, as growth will now be negative for 2025 and may be projected at flat into the future.


The estate exemption amount per couple is now $25M, meaning that you can move up to $25M of assets into an irrevocable trust, which takes it out of your estate for estate tax purposes.


You went from having a $10M estate tax problem to having an extra $8M of room in your exemption amount.


There are many other creative ways that tax planning attorneys can structure things for major wins for depressed asset prices.



Disclaimer: For informational purposes only. This is not legal or tax advice!

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