OBBB Strategy: Generational QSBS Gifting

With the 2025 tax reform officially supercharging Qualified Small Business Stock (QSBS), founders and investors now have a golden window to build generational wealth — tax-free.

If you’re holding early-stage stock in a C-Corp, especially if it qualifies as QSBS under the new law, now is the time to think long-term: Who else in your family should hold some of this tax-free rocket fuel?

The Play: Gift QSBS Early. Stack the Exclusions. Build a Dynasty.

The updated law (Section 1202, post-OBBB) lets each taxpayer exclude up to $15 million in QSBS gains per company, indexed for inflation. That means:

  • You get $15M

  • Your spouse gets $15M

  • Your kids each get $15M

  • Your irrevocable grantor trusts each get $15M

…all with the same stock.

Gifting QSBS Transfers the Holding Period, Not the Cap

Here's the kicker: when you gift QSBS, the holding period carries over to the recipient (e.g., your child, spouse, or trust)… but they get their own lifetime $15M gain exclusion.

So if you’ve held the stock for 2 years, and you gift it to your 18-year-old daughter today, she only has to wait another 3 years to unlock the 50% exclusion at 3 years, 75% at 4, or 100% at 5 — and she gets her own $15M exclusion on that same company.

Build the Stack: Family + Trusts = Mega Exclusions

Let’s say you’re the founder of a fast-growing tech startup and your QSBS is currently worth $1/share.

If you gift 2M shares now (FMV = $2M) to each of the following:

  • Your spouse

  • Two kids

  • Two intentionally defective grantor trusts (IDGTs)

They each get their own $15M cap, plus your holding period. If the company exits at $10/share, the $20M gain in each account could be 100% tax-free.

That’s $120 million in tax-free gains, legally — just by planning ahead.

Add Valuation Discounts for Gifting Efficiency

When gifting to family or trusts:

  • Use valuation discounts (e.g., lack of marketability or minority interest) to reduce gift tax exposure

  • File a protective Form 709 gift tax return to lock in the valuation

This allows you to transfer more equity with less estate/gift tax impact, while preserving the QSBS status.

Sample Scenario

Emma, a startup founder, owns 5M QSBS shares currently worth $1M (pre-raise).

She gifts:

  • 1M shares to her spouse

  • 500k each to two kids

  • 1M each to two IDGTs

Her holding period is 2 years.

Total tax-free gain: $45M+
(Far more if value grows and they hold longer)

Timing Matters

To qualify for the new $15M cap and accelerated timeline (3–5 years), you must acquire the stock after the law’s enactment (2025).

Already have older QSBS? You still get the original $10M exclusion — but that’s stackable too.

Bottom Line

This strategy is a powerful combo of:

  • QSBS gain exclusion

  • Gift and estate tax planning

  • Family wealth transfer

  • Startup equity optimization

It’s one of the most efficient, legal, and future-focused tax plays available right now.

Want to Run the Numbers?

We help founders:

  • Audit their cap tables for QSBS eligibility

  • Structure gifts to family and trusts

  • Coordinate with legal and valuation teams

  • File the right forms to preserve benefits

Let’s talk about how your equity today can unlock tax-free wealth for generations.