Serial entrepreneurs and multi-bet operators face a unique problem: every individual piece may be tax-managed, but nobody's looking at the system. S-corp comp on entity A doesn't talk to S-corp comp on entity B. K-1s from outside investments hit your 1040 without coordination. Inter-entity loans get treated as gifts. We take the seat at the top of the stack and run the whole picture.
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Multi-entity operators come to us with the same three problems: nobody's coordinating across the entities, post-exit complexity that the old CPA wasn't ready for, and partnership-shared structures that work in spirit but not on paper.
"I have 4 LLCs. They're all owned by me personally, all flow to my 1040. My CPA does each one separately. Nobody's looked at the system. I think there's massive inefficiency I can't see."
Serial founder · 4 entities · Apr 2026
"I sold my agency 18 months ago. Now I run a coaching business, hold 3 angel investments, own 2 rentals. Five tax personalities in one return. My CPA hasn't changed how he files since the sale."
Post-exit operator · $1.4M HHI · Mar 2026
"My main S-corp does $1.8M. Side LLC does $400K. My partner is in the side LLC but not the main one. Distributions are different. Books are separate but commingled in real life. It's a mess."
Multi-entity owner · $2.2M HHI · Feb 2026
Multi-entity owners often benefit from a holding company over multiple operating entities. Holdco gives you a single place for retained earnings, cleaner asset protection, simpler exit on any one piece. But it's not the right answer for everyone — we model the legal + tax cost vs. the structural benefit before recommending the rebuild.
Multi-entity operators routinely move money between entities. The IRS cares whether transfers are loans (interest required, documented) or capital contributions (basis adjustment). We rebuild the inter-entity transfer documentation so basis tracking holds up.
If you operate two S-corps, reasonable comp gets paid from each one. Most entrepreneurs underpay themselves on one and overpay on the other (or pay zero on both). We benchmark + harmonize across the entities.
Multi-entity operators have more retirement vehicle capacity than they realize. Solo 401(k) on each S-corp (capped collectively), Cash Balance across the W-2-equivalent income, mega-backdoor Roth. Properly coordinated, $80K–$150K/yr of tax-deferred contribution capacity is realistic.
When you receive K-1s from outside investments (syndications, funds, partnerships) on top of your own entities, the coordination becomes the bottleneck. We aggregate the K-1 timing, manage extensions, surface passive vs. non-passive characterization, and handle the basis tracking.
If you're considering selling any one entity in the portfolio, the structuring decisions are different than for a single-entity owner. QSBS may apply selectively. Personal goodwill allocation depends on which entity is being sold. We model the exit before the LOI lands.
Restructured into holdco / 4 disregarded subsidiaries. Inter-entity loans documented + interest set at AFR. Reasonable comp harmonized across the two S-corp-elected entities. Year-one savings $42K, plus a cleaner exit structure on any one piece.
Rebuilt the books to separate cleanly across coaching business, angel-investment K-1s, rentals, and operator income. Estimated tax restructured around the lumpy K-1 timing. Solo 401(k) + Cash Balance opened. Year-one savings $28K.
Reasonable comp set on both S-corps. Partner-shared LLC formalized as a partnership (was operating informally). Distributions documented + basis tracking rebuilt. Year-one savings $36K + audit-risk eliminated.
3-year scope · holdco / opco modeling · reasonable comp harmonization · K-1 portfolio coordination · inter-entity loan + capitalization audit · retirement vehicle stacking · bench-coordination calls · Tax Defense Plan included.
2-entity operators with $500K HHI or less: Comprehensive ($5K). Solo S-corp with one side hustle that's not yet a separate entity: Standard ($2.5K).
Not always. Holdco's add legal + filing cost (separate 1120 return, separate state filings, often Delaware franchise tax). The structure makes sense when (a) you have 3+ entities, (b) you want centralized retained earnings, (c) asset protection matters, or (d) you're planning to sell one piece without selling the others. We model the decision — not all entrepreneurs need one.
We aggregate the K-1s, coordinate the timing (most partnerships file extensions, which cascades), and handle the basis + passive-vs-non-passive characterization on your 1040. K-1 chaos is one of the most common problems we solve for multi-entity operators.
Yes. Higher-tier retainers include bench-coordination calls baked in. We get on the phone with your attorney, advisor, banker, or business partners. We translate. They stay in their lanes. You stop being the integration glue.
Most multi-entity owners with $500K+ HHI land at Strategic ($10K). Comprehensive ($5K) is fine for 2-entity operators under $500K HHI. The Tax Defense Plan included in Strategic is especially valuable for multi-entity owners because the audit risk surface area is wider. See Strategic.
Bring a list of every entity you own (LLCs, S-corps, partnerships, C-corps), every K-1 you receive from outside investments, and any exits you're considering. We'll quote the right tier and timeline before any work begins.
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