Every choice you make now shows up at the liquidity event.
Going public, or raising on the way there, turns paper equity into real money and real tax. The planning that matters most happens well before the S-1 or the term sheet, and much of it can't be done afterward.
We put securities work and founder tax planning together, with the scrutiny of investors and regulators in mind from the start.
QSBS: the biggest number on the table.
Section 1202 can exclude a large part of the gain on qualified small business stock from federal tax. Eligibility depends on the type of corporation, its gross assets when the stock was issued, how the stock was acquired, the business it's in and how long it's held.
For stock acquired after July 4, 2025, the exclusion is 50% after three years, 75% after four and 100% after five, with a per-company cap generally of $15 million and a $75 million gross-asset limit. Earlier stock follows the older rules. We review eligibility, protect it through each financing, and document it so it holds up at the sale.
- C-corporation structure and conversion planning
- Gross-asset monitoring through each round
- Holding-period tracking and documentation
- Trust planning that can extend the exclusion across family members
Your equity: ISOs, NSOs and RSUs.
Each type of equity is taxed differently, and the timing of grants, exercises and vesting can change the bill a great deal. We review 83(b) elections, plan exercises and model what the liquidity event will mean for you personally.
Trusts before the value is obvious.
Transferring shares to family trusts is far more efficient while the company's value is still modest. Waiting until the valuation jumps can cost much more in gift and estate tax. We set up trusts and pre-IPO charitable transfers early enough to matter.
The raise and the public company.
On the securities side we handle Reg D, Reg A+ and Reg CF offerings, prepare for an S-1, and then the post-IPO obligations that apply to founders and insiders.
- Lock-up agreements and planning around them
- Section 16 reporting and Form 4 filings
- Rule 10b5-1 trading plans
“The difference in having one quarterback for both tax and legal is immeasurable.”
Pre-IPO Founders: common questions
When should pre-IPO tax planning start?
As early as possible, ideally before major financing rounds. QSBS eligibility, 83(b) elections and transfers to trusts all work best, and sometimes only work, before the company's value climbs.
Does my stock qualify for QSBS?
It depends on the corporation, its gross assets at issuance, how you acquired the shares, the company's business and how long you hold them. It's worth a careful review, because the benefit can be very large and some mistakes can't be undone.
Can I move shares into a trust before an IPO?
Often, yes. Transfers made while the company is valued lower use less of your gift and estate tax exemption. The shares need a proper valuation and the transfer has to respect any company restrictions and securities rules.
Preparing to raise or go public?
Tell us where the company is and what's coming. We'll review it and get back to you.