Trump Accounts for Business Owners: Two Decisions, Not One
Trump Accounts hand business owners two separate decisions. See who can actually participate under the Section 128 employer rules, and
Establish QSBS eligibility and restructure concentrated founder equity through QSBS stacking across multiple trust entities to reduce future business sale taxes, reduce federal estate exposure, and build the foundation for a scalable family office structure.
Design a structure that creates meaningful tax savings and creditor protection while preserving control, access and flexibility for a founder whose net worth was largely tied to a privately held operating company.
A founder owned a large, highly appreciated position in a privately held business, with future liquidity likely over the next planning horizon.
However, the ownership and estate structure had not been designed for:
As a result, the founder faced a scenario where a future transaction could create an avoidable tax outcome, and long-term estate exposure could compound materially as the company value grew.
A comprehensive ownership and estate restructuring plan, designed and implemented before the liquidity even, with a focus on:
To maximize future exit flexibility and tax efficiency, we:
Established a clear QSBS eligibility framework for the founder’s ownership
Strategically transferred shares across multiple newly formed trust entities, including:
SLATs
SLANTs
Irrevocable trusts
Other Trusts
This structure was designed to concentrate future appreciation outside the taxable estate while maintaining practical control, access, and planning flexibility for the founder.
The estate plan was rebuilt around ownership strategy, not simply documents. We integrated:
A coordinated trust architecture designed for long-term transfer efficiency
Creditor protection features appropriate for a founder with concentrated business risk
An intentional path toward multi-generational planning and estate tax minimization
A structure that preserved founder influence over assets, even inside irrevocable trusts, through careful role design and entity coordination
Beyond tax planning, the objective was to build durable long-term infrastructure. We:
Assembled and integrated the advisory team across legal, tax, valuation, and investment coordination
Began building the governance foundation, including decision-making structure, trustee/advisor roles, and long-term stewardship planning
Laid the groundwork for a future family office structure that can scale with liquidity and complexity
The planning created immediate structural protection and long-term financial leverage.
Net results:
Over $19 million of projected business sale tax savings through QSBS planning and trust-based structuring
Millions of dollars of future federal estate tax avoided through appreciation removal and multi-entity trust architecture
Meaningful creditor protection for family wealth
A structure designed to preserve control and flexibility, even with assets held in trust
A coordinated advisory team and early governance framework supporting a future family office
This case highlights a key reality for founders: the biggest tax savings don’t come from last-minute tactics. They come from ownership structure built early, while options still exist.
QSBS stacking is rarely as straightforward as it looks on paper. Eligibility, timing, and trust design all have to work together. Below are some of the most common questions we get from founders navigating this process.
QSBS stacking distributes qualified shares across multiple taxpayers — the founder personally plus several irrevocable trusts — so that each entity can claim its own Section 1202 exclusion cap. Because the cap applies per taxpayer, more trusts can mean more total exclusion capacity on the same gain. That’s the structural logic behind the $19 million in projected tax savings in this case. See our QSBS Stacking for Founders guide for a full breakdown of how the mechanics work.
When shares are transferred to irrevocable trusts before a liquidity event, future appreciation generally leaves the founder’s taxable estate. In this case, repositioning shares into SLATs, SLANTs, and other irrevocable structures before the sale meant millions in future appreciation were no longer compounding inside the estate, reducing federal estate tax exposure alongside the capital gains benefit.
Significantly. Section 1202 offers 50%, 75%, or 100% exclusion rates depending on when shares were issued. Most founders today hold Tier 3 stock (issued after September 28, 2010), which qualifies for the full 100% federal exclusion, the tier that makes each additional trust in a stacking structure maximally efficient. Our article on the QSBS tiered system explains how tiers work and how they interact with stacking architecture.
Yes. QSBS eligibility isn’t locked in permanently at issuance. One underappreciated risk is the 5% passive income test – if more than 5% of the company’s gross receipts come from passive sources in any given year, shares outstanding during that period may be disqualified. Founders with minority portfolio stakes, excess cash in interest-bearing accounts, or royalty income face this risk without always knowing it. Our guide on the QSBS 5% passive income test covers how to calculate it and what to do before a breach becomes permanent.
Well before any formal sale process. Transfers made after a binding agreement exists are vulnerable to IRS challenge under the step transaction doctrine, which can attribute gain back to the original holder regardless of the transfer documents. The structures in this case were in place during the pre-sale window – when the full range of options was still available. Once an LOI is circulating, most of the cleanest moves have already closed.
Legal ownership, yes, since an irrevocable trust is genuinely irrevocable. But practical influence can be preserved through trustee selection, trust protector roles, and carefully designed distribution provisions. In this case, the structure was built to maintain access to liquidity for lifestyle and future investments while still achieving the estate and tax benefits that require a genuine transfer. Founders need to understand that distinction clearly before committing to any of these structures.
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