Trust Solutions · Sterling Foundations and Trusts

Advanced Planning for Appreciated Assets

Turn Large Gain Assets Into Lasting Legacies.

If you're planning to sell a business, concentrated stock, appreciated real estate, crypto, or any other appreciated capital asset, the planning decisions you make now will shape your legacy for decades to come.

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Overview

Trust Solutions for Sale of Business, Real Estate, Stock, and Crypto.

Sterling's Trust Solutions helps individuals and families turn large gain assets into lasting legacies. Through the expert use of tax-exempt trusts and advanced planning strategies, we help you:

  • Avoid capital gains tax when you sell your asset
  • Diversify into almost any investments
  • Compound investments tax deferred indefinitely
  • Defer income taxes
  • Receive flexible, lifetime income for multiple generations

Why clients come to Sterling

While others focus on transactions, Sterling focuses on transformation—offering clarity, control, and confidence in the face of life's biggest financial moments.

Real Clients. Real Results.

What Clients and Advisors Say.

Antonia Buban, Founder, Buban Financial Services

"As far as Assets Under Management [growth] is concerned... to give you a number: close to 30 million."

Barbara Bollard, Client

"What struck me was [Sterling's] ability to connect with me as an individual."

"I was already sold before I started."

Bruce Garratt

Bruce Garratt, Client

"We found the firm absolutely first class and excellent in our dealings."

"We can certainly commend the firm to those that wish to consider... long-term planning."

Bruce Popper, Financial Advisor, Lion Street Private Client Group

"I haven't found anybody better in my 40 years than the people I strategized with at Sterling."

"I've found Sterling to be an incredible resource."

Who It Helps

Solutions Designed Around the Asset You're Selling.

Below are four common situations where Trust Solutions can help clients move from concentration and tax drag to flexibility and long-term planning.

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Business Owners

Planning before a sale can help preserve more of the proceeds and create long-term flexibility around diversification, income, and legacy.

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Real Estate & Property Owners

Highly appreciated property can be repositioned through advanced trust planning instead of forcing a taxable sale and immediate capital gains exposure.

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Concentrated Stock Position

Clients with outsized exposure to a single stock may be able to diversify more efficiently while addressing tax, risk, and income goals together.

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Crypto Assets

Digital asset holders can explore planning strategies that address liquidity, volatility, tax impact, and multi-generational objectives.

Explore Case Studies

Real planning scenarios showing how tax-exempt trusts help clients preserve wealth, reduce taxes, and create lasting legacies.

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Case Study #101
Appreciated Stock
$12M Apple position · $3.48M tax savings
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Case Study #103
Appreciated Real Estate
$4M San Diego apartment · $1.42M tax savings
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Case Study #102
Selling a Business
$10.25M software company · $3.8M tax savings
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Case Study #105
Selling an S-Corp
$50M S-corp · $1.1M first-year income tax savings
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Case Study #106
Selling a Dental Practice
$7.8M dental practice · No capital gains tax
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Case Study #107
C-Corp Stock and Taxable Estate
$100M exit · $50M removed from taxable estate
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Case Study #108
Appreciated Stock, Charitable Goal
$100M C-corp · $30M capital gains tax savings
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Case Study #109
C-Corp Stock Sale to Minority Owner
$12M C-corp · Tax-efficient ownership transfer
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Case Study #110
Sell, Diversify, and Get Basis Step-Up
$5M Nvidia · Tax-free sale & basis step-up
Planning with Tax-Exempt Trusts for Clients  |  Case Study #101

Appreciated Stock

Situation

Stanley (“Stan”) is 65, and his wife Betty is 62. They have a daughter, Jessica, who is 32. Stan and Betty own $12,000,000 of Apple, with a basis of $400,000. Their total net worth is approximately $20,000,000, including other investments and real estate.

Stan and Betty’s Goals

  • Reduce the risk inherent in their 60% concentration in Apple
  • Avoid capital gains tax of $3,480,000 upon sale of the Apple stock
  • Benefit from $12,000,000 in value, instead of only $8,520,000 if they sell and pay tax
  • Ability to generate income
  • Ability to invest tax-deferred
  • Create the ability to transfer wealth to their daughter

Sterling’s Recommendation

  • Create a tax-exempt Stock Diversification Trust — beneficiaries are Stan and Betty for their lives; Jessica receives the income after Stan and Betty are gone
  • Contribute the Apple stock to the trust
  • The trust sells the stock and receives the entire $12,000,000
  • Stan and Betty’s advisor invests the $12,000,000 in an appropriate portfolio
► Capital gains tax savings
$3,480,000 in capital gains tax savings
► Net spendable income
2× expected net spendable income over the term of the trust vs. selling and paying tax
► Risk reduction
The stock is sold with no capital gains tax due. Proceeds reinvested in a diversified portfolio
► Lifetime income
Stan & Betty have income for life, or grow it tax-deferred
► Tax deferral
The trust serves as a tax-deferred investment vehicle
► Generational transfer
Daughter Jessica receives income after Stan and Betty
► Income tax deduction
$1,200,000 income tax deduction upon funding
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Planning with Tax-Exempt Trusts for Clients  |  Case Study #103

Appreciated Real Estate

Situation

Robert (“Bob”) is a widower, age 79, with three children: Andrea (49, married, 2 children), Lynne (47, married, no children), and Tony (44, married, 3 children). Bob’s net worth is $8 million, of which $4 million is in a 12-unit San Diego apartment building owned for decades. His basis is $180,000.

Bob’s Goals

  • Eliminate the risk of owning a 12-unit apartment building
  • Avoid capital gains tax of $1,417,220 upon sale of the property
  • Benefit from $4,000,000 in value, instead of only $2,582,780 if he sells and pays the tax
  • Increase available cash flow to Bob
  • Ability to invest tax-deferred
  • Create the ability to transfer wealth to Bob’s children and grandchildren

Sterling’s Recommendation

  • Create three tax-exempt Real Estate Shelter Trusts — Bob receives income for life; after Bob, each child receives income from one trust for life
  • Fund the trusts with the property
  • The trust sells the property and receives the entire $4,000,000
  • Bob’s advisor invests the $4,000,000 in an appropriate portfolio
► Capital gains tax savings
$1,417,220 in capital gains tax savings
► Net spendable income
2× expected net spendable income over the expected term of the trust vs. selling and paying tax
► Access to income
Bob, and eventually his children, can receive lifetime income
► Risk elimination
No longer bears the risk of owning a single property
► Tax deferral
The Real Estate Shelter Trusts serve as tax-deferred investment vehicles
► Generational transfer
Each child receives income from their own trust for life
► Income tax deduction
$400,000 income tax deduction upon funding
← Back to Case Studies
Planning with Tax-Exempt Trusts for Clients  |  Case Study #102

Selling a Business

Situation

Robert is 77, and his wife Laura is 67. They own an LLC software services company worth $10,250,000, including copyrights on software integral to the business. They have two daughters: Natalie (42), who has two teenage sons, and Jenna (40). Robert and Laura expect to need no more than $200,000 a year.

Robert and Laura’s Goals

  • Sell the company within the year
  • Avoid capital gains tax of $3,802,750 upon sale of the company
  • Benefit from $10,250,000 in value, instead of only $6,447,250, if they sell and pay the tax
  • Ability to generate income
  • Ability to invest tax-deferred
  • Create the ability to transfer wealth to their daughters and grandchildren

Sterling’s Recommendation

  • Create two tax-exempt Business Owner Trusts — Robert and Laura as lifetime beneficiaries; then Natalie and Jenna; then Natalie’s sons for a certain period
  • Contribute the company and intellectual property to the two trusts
  • The trust sells the assets and receives the entire $10,250,000
  • Robert and Laura’s advisor invests the $10,250,000 in an appropriate portfolio
► Capital gains tax savings
$3,802,750 in capital gains tax savings
► Net spendable income
2× expected net spendable income over the expected term of the trust vs. selling and paying tax
► Access to income
Robert & Laura, and eventually Natalie and Jenna, receive lifetime income
► Lifetime income
If not needed, income can remain in the trust and grow tax-deferred
► Tax deferral
The Business Owner Trusts serve as tax-deferred investment vehicles
► Generational transfer
Daughters and grandsons can receive income from the trusts
► Income tax deduction
$1,025,000 income tax deduction upon funding
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Planning with Tax-Exempt Trusts for Clients  |  Case Study #105

Selling an S-Corp

Situation

Joe is 58, his wife is 56, and their son, Matt, is 23. Joe owns 100% of an S-corp with annual pre-tax profits of approximately $5 million. Joe’s salary is $300,000. Joe and his wife live in New York, where their personal income tax rate approaches 50%. The estimated value of the company today is $50 million. Joe’s total net worth is about $58 million.

Primary Goals

  • Sell the company within approximately 3 years
  • Avoid capital gains tax upon sale of the company or assets
  • Minimize estate taxes
  • Minimize income taxes between now and the time of sale
  • Create a tax-deferred investment vehicle
  • Option for income from the trust

Sterling’s Recommendation

  • S-Corporations create a number of issues in planning.
  • Solutions depend on specific details, and because they are so dependent on details, we have not published the solution here because without the full context the solution might be misleading for cases with slightly different facts.
  • Please contact us to discuss your S-Corp cases.
► First-year income tax savings
$1,100,000 in first-year income tax savings by converting from S-corp to C-corp, reducing the rate from ~50% to ~28%
► No capital gains tax on sale
The trusts are tax-exempt, so no capital gains tax when the company is sold
► Dividends not taxed in trust
When the C-corp pays dividends to the trust, no tax is due
► Lifetime income
Joe & his wife have income for life; Matt receives income after them
► Estate tax reduction
Value of half the business removed from Joe’s taxable estate
► Tax-deferred growth
Each trust can invest tax-deferred in a wide range of assets
► Income tax deduction
$5,000,000 income tax deduction — approximately 10% of fair market value upon funding
← Back to Case Studies
Planning with Tax-Exempt Trusts  |  Case Study #106

Selling a Dental Practice

Situation

Tony is 57, and his wife Donna is 56. Tony owns a multi-location dental practice (LLC) producing approximately $1.2 million in EBITDA, worth $7,800,000 at a 6.5 multiple. Tony’s basis is effectively zero. They have twins: Ashley and Jennifer, both 32. Ashley has two sons. Jennifer is not married.

Primary Goals

  • Sell the practice to a DSO for at least 6.5x EBITDA
  • Avoid capital gains tax upon sale of the practice or assets
  • Create a flexible wealth preservation and growth legacy
  • Create a tax-deferred investment vehicle for their daughters
  • Maintain the ability to access income if needed
  • Retain the right to revoke a daughter’s interest if needed

Sterling’s Recommendation

  • Create two Business Owner Trusts — Tony and Donna as lifetime beneficiaries; then Ashley and Jennifer; then Ashley’s sons
  • Dental practices vary in their specific structure. The exact nature of what the dentist owns can affect the planning, and did in this case.
  • The dentist retained some assets, and contributed other asset to the trust
  • The dentist remained in control, and sold both his and the trust’s assets. The trust, being tax, free, received the full pre-tax proceeds.
► No capital gains tax on sale
The trusts are tax-exempt, so no capital gains tax when the practice is sold
► Income to Jennifer
Tony and Donna receive 5% of each year’s beginning trust balance for life
► Income to Ashley
After parents pass, Ashley receives income for her life
► Lifetime income
After parents pass, Jennifer receives income for her life
► Tax-deferred growth
Each trust can invest tax-deferred in a wide range of assets
► Option to defer income
~$390,000 available in year one; unreceived income compounds tax-deferred
► Income tax deduction
~$780,000 income tax deduction — approximately 10% of fair market value upon funding
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Planning with Tax-Exempt Trusts  |  Case Study #107

C-Corp Stock and Taxable Estate

Situation

Joe is 63, his wife Anne is 60. Son James is 35, daughter Hanna is 33. Joe owns stock in a closely held C-corp expecting a $100 million cash exit. Basis is under $2 million. Total net worth is ~$180 million. They have $26 million of lifetime estate tax exemption remaining.

Primary Goals

  • Avoid capital gains tax on the exit from XYZ
  • Reduce the size of their eventual taxable estate
  • Retain as much flexibility as possible with the exit wealth
  • Create a tax-deferred investment vehicle with optional income
  • Treat son and daughter fairly
  • Maintain liquidity despite irrevocable trust structure

Sterling’s Recommendation

► Estate reduction
$50M removed from taxable estate using only lifetime exemptions via layered discounting
► No capital gains tax on exit
The stock is sold with no capital gains tax due
► Option to eliminate estate tax
Note can fund a zeroed-out CLAT during life or at second death
► Access to income
Each spouse can access income from the other’s SLAT if needed
► Tax deferral
Trusts serve as tax-deferred investment vehicles
► Generational transfer
James and Hanna become income beneficiaries after parents
► Income tax deduction
$7,500,000 income tax deduction — approximately 10% of fair market value upon funding
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Planning with Tax-Exempt Trusts  |  Case Study #108

Appreciated Stock, Charitable Goal

Situation

Stanley (“Stan”) is 65, and his wife Betty is 62. They have a son, Dan (35), and daughter, Jessica (32). Stan owns $100 million of a closely held C-corp, Marwater Ventures, with a basis of $400,000. They do not need any of the MVI wealth. Stan anticipates selling his shares to a private equity firm.

Primary Goals

  • Avoid capital gains tax associated with sale of the stock
  • Retain potential access to the wealth
  • Create a tax-deferred investment vehicle with optional income
  • Grow the MVI proceeds tax-deferred for charity
  • Leave open the possibility to transfer some wealth to their children
  • Structured as a Liquidy Trust with option to borrow from the trust

Sterling’s Recommendation

  • Create a Master LLC; Stan and Betty contribute MVI stock to it; create two Stock Diversification Trusts (SBD and SBJ)
  • Stan and Betty are lifetime income beneficiaries; Dan and Jessica are revocable successor beneficiaries of their respective trusts
  • Fund each trust with half of the Master LLC units; sell the stock with no capital gains tax
  • Upon second death, remaining net assets fund a private foundation, with option to make charitable contributions while alive
► Capital gains tax savings
$30,000,000 in capital gains tax savings
► Tax-free growth for charity
Undistributed income grows tax-deferred; passes to charity tax-free
► Diversification
Portfolio reinvested in a diversified range of assets
► Retain access to income
Stan and Betty can receive income, or let it compound in the trusts
► Tax deferral
Trusts serve as tax-deferred investment vehicles
► Family option preserved
Dan and Jessica named as revocable successor beneficiaries
► Liquidity
Income rights can be sold; option to borrow from the trust
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Planning with Tax-Exempt Trusts  |  Case Study #109

C-Corp Stock Sale to Minority Owner

Situation

Mark, 63, owns 90% of RISI, a closely held C-corp worth $12 million total. The company generates ~$1.5M in annual net after-tax profit. Mark has two children: Sam (works in the business, owns 10%) and Amanda. RISI represents most of Mark and his wife Sharon’s net worth.

Primary Goals

  • Transfer ownership of RISI to Sam as tax-efficiently as possible
  • Treat Amanda as equally as possible
  • Avoid debt or other large fixed payment obligations
  • Have access to income after retirement
  • Maintain flexibility with no obligatory fixed payments
  • Retain liquidity despite irrevocable trust structure

Sterling’s Recommendation

► Tax-efficient stock transfer
Gains from RISI buybacks are not taxed at the trust level
► Sam gains full ownership
As RISI retires shares, Sam’s percentage grows to 100%
► No borrowing required
Corporation uses net profits to buy back stock when available
► Retirement income
Mark and Sharon entitled to 5% income (~$500,000 in year one)
► Tax deferral
Trusts serve as tax-deferred investment vehicles
► Fair treatment for both children
Sam gets the business; Amanda gets income from her trust
► Income tax deduction
~10% income tax deduction — approximately 10% of fair market value upon funding
← Back to Case Studies
Planning with Tax-Exempt Trusts  |  Case Study #110

Sell, Diversify, and Get Basis Step-Up

Situation

Tom Roberts and his wife Francine are both 65. Their only daughter, Julie, is 30. Combined net worth is $9.5 million, $5 million of which is in Nvidia. They have a modest lifestyle and don’t need liquidity or income, but their advisor has strongly suggested they diversify the position.

Primary Goals

  • Sell the Nvidia and diversify without paying capital gains tax
  • Reinvest the resulting $5 million in a diversified portfolio
  • Grow the diversified portfolio in a tax-deferred manner
  • Have the option to access income from the portfolio
  • Eventually allow Julie to benefit from a stepped-up basis
  • Maintain liquidity despite irrevocable trust structure

Sterling’s Recommendation

  • Create a tax-exempt Stock Diversification Trust — Tom and Francine as lifetime beneficiaries; Julie becomes beneficiary after them
  • Fund the trust with the Nvidia stock
  • The trust sells the Nvidia stock with no capital gains tax
  • The resulting $5 million is reinvested in a diversified portfolio by their advisor
► Tax-free stock sale
Nvidia sold with no capital gains tax; the trust is tax-exempt
► Retain the full $5,000,000
No tax due, allowing the entire amount to be invested and compounded
► Tax-deferred growth
Income and gains are not taxed unless distributed before basis step-up
► Optional income
Tom and Francine entitled to 5% income (~$250,000 in year one)
► Diversification
Nvidia proceeds reinvested in a diversified portfolio
► Basis step-up at death
Contact Sterling for explanation of basis step-up
► Continued deferral for Julie
Julie can continue the trust or exit tax-efficiently after parents
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"Any one may so arrange his affairs that his taxes shall be as low as possible."
Learned Hand
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