Tax-free reorganization, QSBS strategy, and Delaware 368(a) walkthrough for VC-backed startups
Timing your conversion correctly can save hundreds of thousands in taxes and preserve QSBS benefits. Here's how to decide.
| Scenario | When to Convert | Why |
|---|---|---|
| Pre-Product / Idea Stage | NOW (form as C-Corp instead) | Zero assets = clean conversion. Start QSBS clock immediately. |
| MVP Built, Pre-Revenue | NOW (before revenue) | Low valuation makes 368(a) reorganization straightforward. Minimal tax risk. |
| Generating Revenue ($50K-500K/yr) | Before hitting $1M ARR | Still manageable valuation. Convert before VC talks start. |
| Profitable or High Revenue | ASAP, but with tax advisor | Higher valuation means more complex. May need 409A valuation. |
| In Fundraising Talks | Too late—should have converted 3-6 months ago | Rushed conversion can delay funding, miss QSBS benefits, or trigger taxes. |
Qualified Small Business Stock (QSBS) under IRC §1202 can exclude up to $10M or 10x your investment (whichever is greater) from capital gains tax. But the clock starts when the C-Corp issues stock—not when your LLC was formed.
Exit at $50M: You own 20% = $10M
Investment: $100K
Gain: $9.9M
Long-term capital gains tax (23.8%): -$2,356,200
Net: $7,543,800
Exit at $50M: You own 20% = $10M
Investment: $100K
Gain: $9.9M
QSBS exclusion: $9.9M (up to $10M limit)
Tax: $0
Net: $10,000,000
Save $2.36M in taxes! 🎉
The IRS treats LLC-to-C-Corp conversion as a taxable event unless you follow specific rules. Here's how to convert tax-free.
| Method | Section 351 Exchange | Section 368(a) Reorganization |
|---|---|---|
| Best For | Simple conversions, same members become shareholders | Complex situations, changing ownership, preparing for VC funding |
| How It Works | LLC members contribute LLC interests to new C-Corp in exchange for stock | LLC merges into new C-Corp (statutory merger under state law) |
| Control Requirement | Transferors must own 80%+ of C-Corp immediately after | No specific control requirement |
| State Law Merger? | No (tax election only) | Yes (formal merger under Delaware/state law) |
| Complexity | Lower (mostly tax filings) | Higher (legal merger + tax treatment) |
| Cost | $2,500-$7,500 | $5,000-$15,000 |
| VC Preference | Acceptable for simple cases | Preferred (cleaner for future rounds) |
The preferred method for VC-backed startups. This is the cleanest path from LLC to Delaware C-Corp.
Create a new Delaware C-Corporation that will be the surviving entity.
Timeline: 1-2 weeks
Cost: $89 filing fee + $50-150 registered agent
Create formal merger agreement between LLC and C-Corp.
Timeline: 3-5 days (with attorney)
Cost: Included in legal fees
LLC members vote to approve the merger (check your Operating Agreement for required vote percentage).
Timeline: 1-7 days (depending on member availability)
C-Corp board of directors and shareholders approve merger.
Timeline: 1-2 days
File Articles/Certificate of Merger with Delaware and LLC's home state (if different).
Timeline: 3-10 business days (state processing)
Cost: $200-500 per state (filing fees)
C-Corp issues stock to former LLC members per conversion schedule.
Timeline: 1-3 days after merger effective
If stock is subject to vesting, file 83(b) elections within 30 days.
Timeline: Must complete within 30 days of merger
Cost: $0 (DIY) or $200-500 (attorney preparation)
Transfer contracts, IP, accounts, and other assets to C-Corp. Dissolve LLC.
Timeline: 2-4 weeks
Cost: $50-200 (state dissolution fees)
File final LLC tax return and begin C-Corp tax filings.
Timeline: At tax filing deadlines
Cost: $1,500-5,000 (accountant fees)
Wyoming LLCs are popular for privacy and low costs, but VCs require Delaware C-Corps. Here's the conversion path.
Create new Delaware C-Corp (this will be the surviving entity).
Wyoming LLC merges into Delaware C-Corp (cross-jurisdictional merger).
Wyoming LLC members vote to approve merger (per Operating Agreement).
File Certificate of Merger in Delaware and Wyoming.
Delaware C-Corp issues stock to former WY LLC members. File 83(b) elections if needed. Dissolve WY LLC.
Wyoming LLCs don't require member names on public filings (privacy benefit). But C-Corps require shareholder lists, and VCs will conduct full diligence on ownership.
Solution: Privacy benefits end when you take VC funding anyway. VCs require full transparency.
Wyoming has the strongest charging order protection for LLCs. C-Corps don't have this protection.
Solution: If asset protection was your goal, consider keeping a separate Wyoming LLC for asset holding, separate from your operating C-Corp.
Get your LLC-to-C-Corp conversion done right. Includes tax planning, legal documentation, and QSBS optimization.
Simple LLC with 1-2 members, no significant assets
Multiple members, revenue-generating, pre-funding
High valuation, multiple classes, in fundraising
Get a consultation to discuss your conversion timeline, tax implications, and QSBS strategy.