Contents
- Rev. Rul. 99-5: SMLLC → partnership (purchase vs contribution)
- Admitting service partners: profits interests vs capital interests
- 704(c): book-ups, built-in gain, and the ceiling rule
- 754/743(b): basis step-ups in transfer events + SBIL rules
- LLC → C-Corp: Rev. Rul. 84-111 methods + QSBS implications
- 357(c): liabilities-over-basis trap + Peracchi note risk
- Blocker corporations for tax-exempt/foreign investors
- Compliance + state nonconformity (technical terminations, S elections)
1) Rev. Rul. 99-5: adding a member changes everything
When a single-member LLC becomes multi-member, it becomes a partnership for tax purposes. Rev. Rul. 99-5 says the pathway depends on how the new member enters—and the two pathways can have radically different tax outcomes. :contentReference[oaicite:2]{index=2}
Situation 1: buyer purchases from owner (“deemed asset sale”)
The IRS treats the owner as selling a slice of each underlying asset, then both parties contribute assets to a new partnership. This can trigger immediate gain (ordinary/capital based on asset character) and create stepped-up basis for the buyer. :contentReference[oaicite:3]{index=3}
Situation 2: buyer contributes to the LLC (“deemed formation”)
Generally structured as contributions under Section 721 (often nonrecognition), but creates built-in gain that must be tracked and allocated correctly under 704(c). :contentReference[oaicite:4]{index=4}
2) Service partners: profits interests vs capital interests
Granting equity for services is where Section 721 protection disappears. If the recipient gets current liquidation value, it can become ordinary compensation income under Section 83. A profits interest can be structured to be non-taxable at grant under IRS safe harbors—but valuation is the whole game. :contentReference[oaicite:5]{index=5}
Practical safeguard: file an 83(b) election
Even when using profits interest safe harbors, many practitioners file an 83(b) election as “cheap insurance” in case the IRS later argues the interest had value at grant. :contentReference[oaicite:6]{index=6}
3) 704(c): book-ups, built-in gain, and the ceiling rule
When a new member buys in at FMV, partnerships often “book up” capital accounts. But tax basis stays historical. Section 704(c) forces tax allocations that keep pre-contribution gain with the historic partners—yet the ceiling rule can block the allocation, creating distortions unless you choose a method (traditional, curative, or remedial). :contentReference[oaicite:7]{index=7}
Traditional
Respects the ceiling rule; distortions can persist (often founder-favorable deferral). :contentReference[oaicite:8]{index=8}
Curative
Uses other real tax items to “cure” distortions—works only if the partnership has the right items. :contentReference[oaicite:9]{index=9}
Remedial
Creates notional tax items to match economics; investor-friendly but accelerates income to historic partners. :contentReference[oaicite:10]{index=10}
4) 754/743(b): basis step-ups when interests are sold
Secondary sales create a mismatch between the buyer’s outside basis (what they paid) and their share of inside basis (historical). A 754 election can create a personal 743(b) adjustment for the buyer, allocated to underlying assets, often producing higher depreciation or lower gain later. TCJA also introduced mandatory adjustments in certain “substantial built-in loss” cases. :contentReference[oaicite:11]{index=11}
5) LLC → C-Corp: Rev. Rul. 84-111 methods (and QSBS consequences)
Converting to a corporation for fundraising or an IPO is often framed as “tax-free,” but the method matters. Rev. Rul. 84-111 outlines three pathways (assets over, assets up, interests up) with different friction and different implications for basis, holding periods, and QSBS planning. :contentReference[oaicite:12]{index=12}
Rule of thumb
“Assets over” is commonly viewed as the cleanest route for QSBS “original issuance” mechanics, and it’s often the default characterization for statutory conversions. :contentReference[oaicite:13]{index=13}
6) The 357(c) liability trap: “tax-free” can become taxable fast
In a Section 351-style incorporation, if liabilities assumed exceed asset basis, the excess can be recognized as gain under 357(c). Mature LLCs can be especially vulnerable due to depreciation and debt-financed distributions. Some taxpayers try to use personal note strategies (e.g., Peracchi-style) to increase basis, but the position can be aggressive and scrutinized. :contentReference[oaicite:14]{index=14}
7) Institutional capital: blocker corporations (UBTI / ECI)
Pass-through income can be a problem for tax-exempt and foreign investors (UBTI/ECI concerns). A common solution is inserting a C-Corp “blocker” between the investor and the LLC so the blocker absorbs the pass-through character and filing obligations. :contentReference[oaicite:15]{index=15}
8) Compliance and state nonconformity traps
Federal rules evolve (e.g., technical termination repeal), but states may not conform—creating short-year state return problems. Separately, S-election timing is unforgiving, and mid-year elections can create short tax years; late-election relief may be available if requirements are met. :contentReference[oaicite:16]{index=16}
Bottom line
The “best” LLC structure is not static. Growth events are where founders either preserve value through basis planning (704(c), 754) and clean conversion mechanics (84-111), or accidentally trigger tax acceleration (99-5 deemed sales, 357(c) traps) and compliance risk (state nonconformity). Treat lifecycle events as tax architecture—not paperwork. :contentReference[oaicite:17]{index=17}