🦍 OBBB Play: Startup Founders and Investors Can Now Go (Half) Tax-Free in Just 3 Years
Who says you have to wait five years to cash out tax-free? Congress just threw founders and angels a banana with the new OBBB — and it’s the juiciest QSBS update in decades.
🚀 What’s New for QSBS? (Qualified Small Business Stock)
⏩ Faster Road to Tax-Free Gains
3 Years: 50% of your gain is tax-free
4 Years: 75% is tax-free
5+ Years: 100% exclusion (classic rule still applies)
This means founders and investors can hit a tax-free payday way sooner — perfect for that 3–5 year startup journey.
đź’° Bigger Lifetime Cap
New shares: $15 million lifetime gain exclusion (indexed after 2027)
Old shares: $10 million cap still applies
If you’re stacking big equity, or playing in multiple rounds, this change is a total game changer.
🦍 More Startups Qualify
The “small business” asset test jumps from $50M to $75M
Now, late-stage and VC-backed startups (even Series C) can qualify
More founders, more investors, more bananas for everyone
đź“ť Key Moves for Founders & Investors
1. Track Stock Dates Carefully:
New QSBS benefits only apply to shares acquired after July 2025
You’ll need to track each tranche separately (and so will your accountant)
2. Stack the Exclusion:
Each person gets their own cap, per company
Spouses, kids (via trusts or Trump Accounts), and even employees can multiply the benefit
3. Plan Your Exit:
You’ve got choices: 3 years for 50%, 4 for 75%, or hold for 5+ for the whole enchilada
Align with other big deductions — like NOLs, bonus depreciation, or Opportunity Zones
🦔 Why Use Hedgi for This?
Hedgi tracks all your QSBS acquisitions, holding periods, and breakpoints
Models what each possible exit year will save you (3, 4, or 5+)
Exports tax-ready reports for your CPA or investor
Helps you combine QSBS with OZs, R&D credits, and other exit strategies
⚠️ Don’t Forget the Fine Print
QSBS still requires a domestic C-Corp (no S corps or LLCs)
Stock must be original issue (not secondaries)
Company must be active — not just a shell or holding company
🎯 Bottom Line
If you’re a founder, angel, or early employee with big dreams — the OBBB QSBS reboot is your best chance for a life-changing, tax-free exit.
Want to see what a 3-year, 4-year, or 5-year plan looks like for your cap table?
Get on the Hedgi waitlist.
Let’s make sure the only thing you leave behind is your tax bill.