Our Blog
Gain clarity and confidence in your financial future. The SSG Companies Blog shares expert insights on wealth transfer, succession planning, and business transitions—helping high-net-worth families preserve and grow their legacies.
Wealth Transfer
How a coordinated wealth transfer strategy protected a family’s business, equalized their children’s inheritances, and prepared for whatever Congress does next.
The permanent exemption didn’t fix the liquidity gap—and it’s the gap that kills plans.
A high exemption changed the math. It didn’t change the risk.
The exemption went up. The case for ILITs didn’t go away.
A resource for financial advisors, CPAs, and attorneys serving business owner clients.
Business Transition
A business transition story that protected the owner’s retirement, preserved the business, and treated every family member fairly.
What happens when a business owner doesn’t plan their exit—and why it costs more than you think.
Your buy-sell agreement is only as good as the money behind it.
If your business can’t survive without you, it isn’t worth what you think it is.
A self-assessment for business owners—and a resource for the advisors who serve them.
ESOP Repurchase Liability Funding
Your company made a promise to every participant. Here’s how companies like yours are making sure they can keep it.
The warning signs every ESOP board and trustee should be watching for.
The warning signs every ESOP board and trustee should be watching for.
Which repurchase liability strategy actually works for ESOP companies?
A resource for ESOP trustees, fiduciaries, and the advisors who serve ESOP companies.
Executive Benefits
The executive benefit strategy that turns retention from a hope into a structure.
They know the 401(k) won’t get them there. The question is whether you’ll close the gap—or their next employer will.
The retention gap is not about generosity. It’s about math.
Which executive benefit strategy fits your company? A comparison guide.
A resource for business owners, CFOs, and the advisors who serve them.
For Advisors
How CPAs, attorneys, and financial advisors can reopen the estate planning dialogue in a post-sunset world.
The gaps that CPAs, attorneys, and financial advisors can identify before the deal falls apart.
How ESOP advisors, CPAs, and attorneys can add value by surfacing the funded obligation gap.
How CPAs, attorneys, and financial advisors can introduce executive benefit solutions to retention-challenged clients.
Life Insurance
It's Not About What You Make. It's About What You Keep.
Privately held business owners spend years optimizing revenue, margin, and growth. Far fewer spend the same energy optimizing the structure that sits underneath all of it — the one that decides how...
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ESOP Repurchase Liability: Why the Funding Gap Widens if You Don't Address It
Every ESOP company owes departing employee-owners cash for their vested shares. That much is well understood. What's less well understood is how predictably — and how quietly — the gap between that...
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Executive Benefit Plans: Why Salary and a Standard 401(k) Aren't Enough to Retain Key Talent
Ask a closely held business owner what they're doing to retain their most critical executives and key employees, and the answer is often some version of "we pay competitively and we have a good 401...
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Business Transition Planning: Why Your Exit Is an Estate Plan and a Tax Plan, Not Just a Sale
Ask a business owner what their "transition plan" is, and most describe a transaction: a target price, a rough sense of who might buy the company, maybe a timeline. Ask a handful of follow-up...
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Whole Life vs. Indexed Universal Life: Which Policy Is Right for You?
When it comes to permanent life insurance, two popular options often compete for attention: whole life insurance and indexed universal life (IUL) insurance. Both offer lifelong coverage and a cash...
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Why Consider COLI for ESOP Repurchase Liability Funding?
Corporately owned life insurance (COLI) can be an essential component of long‑term ESOP repurchase liability planning. For business owners focused on sustainable business transition planning,...
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Turning the ESOP Repurchase Obligation Into a Strategic Advantage
Most ESOP companies see the Repurchase Obligation (RO) as a cost they have to manage and nothing more. It shows up as a line item, a future drain on cash, and a compliance requirement to check off...
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Management Services Organization (MSO) Tax Strategy
It's Not About What You Make. It's About What You Keep. Privately held business owners spend years optimizing revenue, margin, and growth. Far fewer spend the same energy optimizing the structure...
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Premium Financed Life Insurance: How High-Net-Worth Families Use Leverage for Wealth Transfer
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Is It More Efficient to Leave a Charitable Legacy with Life Insurance?
Giving back is more than a gesture for many high-net-worth individuals (HNWIs); it reflects their enduring values. Whether supporting a long-time cause or a nonprofit aligned with their legacy,...
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Charitable Giving with Life Insurance: Enhancing Your Legacy
Charitable giving through life insurance offers a strategic way to enhance your legacy while benefiting from various tax advantages. This approach allows you to make significant contributions to...
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ESOP Sustainability
ESOP Sustainability Brief An ESOP succeeds over decades only when its capital structure, cash flow, and repurchase obligations are managed with discipline. Most companies wait too long to confront...
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Generation-Skipping Trusts: How to Protect Family Wealth for Three Generations
There's an old saying in wealth management circles: "shirtsleeves to shirtsleeves in three generations." The first generation builds the wealth, the second maintains it, and the third — having...
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Spousal Lifetime Access Trusts (SLATs): Locking In Today's Gift Tax Exemption
For many couples, lifetime gifting strategies raise an immediate, practical objection: what if we need that money later? A Spousal Lifetime Access Trust (SLAT) is one of the few wealth transfer...
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The Use of Corporately Owned Life Insurance to Fund Corporate Liabilities
Executive SummaryCorporately owned life insurance (COLI) has long been used by organizations to fund future liabilities, stabilize benefit programs, and manage long-term financial risks. Over the...
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Whole Life vs. Indexed Universal Life: Which Policy Is Right for You?
When it comes to permanent life insurance, two popular options often compete for attention: whole life insurance and indexed universal life (IUL) insurance. Both offer lifelong coverage and a cash...
Read more
ESOP Sustainability
ESOP Sustainability Brief An ESOP succeeds over decades only when its capital structure, cash flow, and repurchase obligations are managed with discipline. Most companies wait too long to confront...
Read more
Charitable Giving with Life Insurance: Enhancing Your Legacy
Charitable giving through life insurance offers a strategic way to enhance your legacy while benefiting from various tax advantages. This approach allows you to make significant contributions to...
Read more
Is It More Efficient to Leave a Charitable Legacy with Life Insurance?
Giving back is more than a gesture for many high-net-worth individuals (HNWIs); it reflects their enduring values. Whether supporting a long-time cause or a nonprofit aligned with their legacy,...
Read more
Understanding the One Big Beautiful Bill Act
The “One Big, Beautiful Bill” (OBBBA) represents a significant shift in U.S. tax policy, bringing a mix of permanent and temporary changes. This is more than just political rhetoric; it has real...
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