FR EA
1023-00003 · Ironside Capital Management LP · IDR Responses
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CALDERWOOD & HARKNESS LLP Attorneys at Law

1251 Avenue of the Americas, 40th Floor New York, New York 10020

Telephone: (212) 558-4000 Facsimile: (212) 558-3588 www.calderwoodharkness.com

August 18, 2023

VIA CERTIFIED MAIL AND IRS SECURE MESSAGING

Revenue Agent Timothy J. Albrecht, GS-13 Badge No. 74-28193 Internal Revenue Service Large Business & International Division Pass-Through Entities Practice Area 290 Broadway New York, New York 10007

Re: Ironside Capital Management LP EIN: 83-2741956 Form 1065, Tax Year Ended December 31, 2021 Response to Information Document Request #4 (8 Items)

Dear Revenue Agent Albrecht:

I am Leila Nazari, Lead Associate in the Tax Department of Calderwood & Harkness LLP, and I write on behalf of our client, Ironside Capital Management LP ("ICM" or the "Partnership"), in connection with the above-referenced examination. Pursuant to Form 2848 (Power of Attorney and Declaration of Representative) filed with the Internal Revenue Service (the "Service") on April 14, 2023, Sylvia Hartwell and Leila Nazari have been designated as ICM's authorized representatives in this matter. A copy of the executed Form 2848 was previously provided to you in connection with our response to Information Document Request #1 on May 5, 2023, and remains in full force and effect.

This letter constitutes ICM's complete response to Information Document Request #4 ("IDR #4"), which was received by our office on August 4, 2023. IDR #4 consists of eight (8) items, each of which relates to the organizational and syndication cost deductions claimed on ICM's United States Return of Partnership Income (Form 1065) for the tax year ended December 31, 2021. For each of the eight items requested, we have provided a detailed narrative response below and have enclosed supporting documentation as specifically identified herein.

This response is submitted under the direction and supervision of Sylvia Hartwell, Responsible Partner in the Tax Department of Calderwood & Harkness LLP. We trust that the documentation and explanations provided below will fully address the Service's inquiries. Should any questions remain following your review, we are available to discuss them at your convenience.

I. BACKGROUND — ORGANIZATIONAL AND SYNDICATION COSTS

A. Formation of Ironside Capital Management LP

Ironside Capital Management LP was formed as a Delaware limited partnership on June 14, 2016, pursuant to the Delaware Revised Uniform Limited Partnership Act, 6 Del. C. § 17-101 et seq. The Certificate of Limited Partnership was filed with the Delaware Secretary of State on that date and assigned File Number 6142857.

The sole general partner of ICM is Ironside Capital GP LLC, a Delaware limited liability company (EIN: 83-2741890), which was organized under the Delaware Limited Liability Company Act on May 27, 2016, for the purpose of serving as the general partner and investment manager of ICM. Ironside Capital GP LLC is managed by its two managing members, Desmond R. Calloway (Founder and Chief Investment Officer) and Priya Venkatesh (Chief Operating Officer and Chief Financial Officer), who together exercise full authority over the day-to-day management and investment activities of the Partnership.

ICM's registered agent in the State of Delaware is Capitol Statutory Services LLC, located at 1209 Orange Street, Wilmington, Delaware 19801. The Partnership is also qualified to do business in the State of New York, having filed its Application for Authority with the New York Department of State on July 8, 2016.

ICM operates as a multi-strategy hedge fund employing three principal investment strategies: (i) global macro, encompassing directional and relative-value positions across global equity, fixed income, currency, and commodity markets; (ii) event-driven equity, focusing on merger arbitrage, activist situations, spin-offs, and corporate restructurings; and (iii) credit strategies, encompassing long/short positions in investment-grade and high-yield corporate bonds, distressed debt, and structured credit instruments. The Partnership's investment activities have been continuous and uninterrupted since its inception in 2016.

The fund's third-party administrator is Greystone Fund Administration LLC, which has been responsible for net asset value calculations, investor accounting, and financial statement preparation since ICM's inception. Greystone provides monthly NAV statements to ICM's limited partners and supports the preparation of annual audited financial statements and Schedule K-1s.

B. Costs Incurred in Connection with Formation

In connection with the formation and organization of ICM in 2016, the Partnership incurred total organizational and startup costs of approximately $1,420,000 (the "Formation Costs"). These Formation Costs were incurred during the period from approximately March 2016 through August 2016 and encompassed a range of legal, accounting, tax advisory, and filing expenses that were directly incident to the creation and establishment of the Partnership as a going concern.

ICM made a timely election under Section 709(b) of the Internal Revenue Code of 1986, as amended (the "Code" or "IRC"), to deduct organizational expenses. In accordance with IRC § 709(b)(1)(A), ICM deducted the first $5,000 of qualifying organizational expenses in the tax year of formation (the short tax year ended December 31, 2016), subject to the phase-out for organizational expenses exceeding $50,000. The remaining qualifying organizational expenses were amortized ratably over a 180-month period beginning with the month in which the Partnership began business, as required by IRC § 709(b)(1)(B). The election statement was attached to ICM's initial Form 1065 for the short tax year ended December 31, 2016.

The organizational expense deductions reflected on ICM's 2021 Form 1065 — the return year under examination — represent the ongoing annual amortization of these Formation Costs over the applicable 180-month period. Specifically, the 2021 amortization deduction represents the sixth full calendar year (January through December 2021) of the amortization period, which commenced in June 2016.

ICM's 2021 Form 1065 was prepared and filed by Borwick Craine & Associates LLP, a certified public accounting firm with offices in New York and Boston. The engagement partner for tax services was Elliot Navarro, CPA. The return was filed on September 15, 2022, on extension pursuant to a timely-filed Form 7004, Application for Automatic Extension of Time to File Certain Business Income Tax, Information, and Other Returns.

C. The IRS's Area of Inquiry

Based on our understanding of IDR #4 and our prior communications with the examination team, the Service's inquiry centers on whether $680,000 of the total $1,420,000 in Formation Costs was properly classified as deductible organizational expenses under IRC § 709(b), or whether those costs should instead be reclassified as non-deductible syndication costs under IRC § 709(a). The $680,000 at issue consists principally of legal fees for drafting, structuring, and negotiating the Partnership's Limited Partnership Agreement, legal fees for filing and registration, and accounting and tax advisory fees for establishing the Partnership's initial accounting and tax reporting infrastructure.

ICM maintains — and the contemporaneous documentation enclosed herewith confirms — that the entire $1,420,000 claimed under IRC § 709(b) was properly classified as organizational expenses. The $680,000 subset questioned by the Service consists of legitimate organizational expenses that were incident to the creation of the Partnership itself, not to the marketing or sale of partnership interests. As detailed in Sections III and IV below, ICM's position is supported by the plain language of the applicable Code provisions and Treasury Regulations, the contemporaneous classification decisions made by the Partnership's general partner at the time of formation, detailed legal invoices with narrative time entries, and an independent classification memorandum prepared by Borwick Craine & Associates LLP in 2016.

II. LEGAL FRAMEWORK — IRC §§ 709 AND 195

A. Organizational Expenses Under IRC § 709

Section 709(b)(1) of the Internal Revenue Code permits a partnership to elect to deduct organizational expenses in accordance with a specific statutory framework. Under IRC § 709(b)(1)(A), a partnership may elect to deduct up to $5,000 of organizational expenses in the taxable year in which the partnership begins business. This $5,000 amount is reduced (but not below zero) by the amount by which the total organizational expenses exceed $50,000. Under IRC § 709(b)(1)(B), any remaining organizational expenses not deducted in the first taxable year are amortized ratably over a period of not less than 180 months, beginning with the month in which the partnership begins business.

The term "organizational expenses" is defined in Treasury Regulation § 1.709-2(a) as expenditures that satisfy all three of the following requirements:

(1) The expenditure is incident to the creation of the partnership;

(2) The expenditure is chargeable to capital account; and

(3) The expenditure is of a character which, if expended incident to the creation of a partnership having an ascertainable life, would be amortized over such life.

Treasury Regulation § 1.709-2(a) further provides illustrative examples of expenses that qualify as organizational expenses. These include, but are not limited to:

• Legal fees for services incident to the organization of the partnership, such as negotiation and preparation of a partnership agreement;

• Accounting fees for services incident to the organization of the partnership; and

• Filing fees paid to state or local jurisdictions in connection with the formation of the partnership.

The regulation makes clear that organizational expenses are those expenditures that relate to the creation and structuring of the partnership entity, as distinguished from expenditures that relate to the conduct of the partnership's business or the marketing of partnership interests. To qualify, the expenditure must be directly connected with the establishment of the partnership as a legal entity and the establishment of the framework within which the partnership will operate.

Importantly, the legislative history and administrative guidance confirm that Congress intended the definition of organizational expenses to be applied broadly to encompass the full range of costs necessary to bring a partnership into existence as a functioning legal and economic entity. The costs of negotiating and drafting the partnership agreement — including provisions governing capital contributions, allocations of income and loss, distributions, management authority, admission and withdrawal of partners, fiduciary duties, and dissolution — are paradigmatic organizational expenses because they define the fundamental structure and governance of the partnership entity.

B. Syndication Costs Under IRC § 709(a)

In contrast to the favorable treatment afforded to organizational expenses, Section 709(a) of the Code provides that "no deduction shall be allowed under this subtitle to the partnership or to any partner for any amounts paid or incurred to organize a partnership or to promote the sale of (or to sell) an interest in such a partnership." While the second clause of this sentence broadly disallows deductions for organizational expenses (subject to the election under § 709(b)), the critical language for present purposes is the prohibition on deductions for amounts paid or incurred "to promote the sale of (or to sell) an interest in such a partnership." These amounts — commonly referred to as "syndication costs" — are permanently non-deductible.

Treasury Regulation § 1.709-2(b) defines syndication costs as "expenditures connected with the issuing and marketing of interests in the partnership." The regulation provides the following illustrative, but non-exhaustive, list of syndication costs:

• Brokerage fees;

• Registration fees (including fees under federal or state securities laws);

• Legal fees of the underwriter or placement agent and the issuer (the partnership or the general partner) for securities advice and for preparation of selling and compliance documents;

• Printing costs of the prospectus, placement memorandum, and other selling and promotional materials; and

• Accounting fees for preparation of representations to be included in the offering materials.

The regulatory framework draws a stark line: syndication costs may not be deducted or amortized under any provision of the Code. They must be permanently capitalized as part of the cost of raising capital. This treatment reflects the policy determination that costs of marketing and selling partnership interests are capital in nature and are not properly viewed as startup or organizational expenditures susceptible to recovery through amortization.

C. The Critical Distinction

The distinction between organizational expenses (deductible under the § 709(b) election) and syndication costs (permanently non-deductible under § 709(a)) turns on a fact-intensive inquiry into the purpose and nature of each expenditure. The key question is whether the expenditure relates to the creation and structuring of the partnership entity itself — in which case it is an organizational expense — or to the marketing and sale of interests in the partnership to investors — in which case it is a syndication cost.

This distinction is well established in the case law and administrative guidance. In Surloff v. Commissioner, T.C. Memo. 1995-279, the Tax Court examined the characterization of various formation-related expenses and emphasized that the determination must be based on the specific nature of the services rendered, rather than on broad, undifferentiated categorizations. Similarly, in Johnsen v. Commissioner, T.C. Memo. 1996-56, the court reiterated that the touchstone of the analysis is whether the expenditure serves the purpose of bringing the partnership into existence as a legal entity (organizational) or serves the purpose of selling interests in the partnership to prospective investors (syndication).

Where costs serve a dual purpose — for example, where a single engagement letter encompasses both the drafting of the partnership agreement (organizational) and the preparation of a private placement memorandum (syndication) — the costs must be allocated between organizational and syndication categories based on the primary purpose of each component and the factual circumstances surrounding the expenditure. The Treasury Regulations do not prescribe a specific allocation methodology; rather, the allocation must be reasonable and supported by contemporaneous documentation.

In the case of ICM, as described in detail below, the Partnership and its advisors undertook a careful, contemporaneous analysis at the time of formation to identify and classify each category of expenditure as either organizational or syndication. That classification was memorialized in formal board resolutions, reflected in detailed legal invoices with narrative time entries, and independently documented in a memorandum prepared by Borwick Craine & Associates LLP. The result of that analysis was a clear segregation of organizational expenses from syndication costs, with syndication costs separately capitalized and excluded from the amounts deducted under IRC § 709(b).

III. FACTUAL BASIS FOR ICM'S CLASSIFICATION OF THE $680,000

A. Nature of the Costs at Issue

The $680,000 in formation-year costs that are the subject of the Service's inquiry consists of three principal categories of professional fees, all of which were incurred during the period from approximately March 2016 through August 2016 in direct connection with the creation and organization of ICM as a Delaware limited partnership. Each category is described below.

1. Legal Fees for Drafting and Negotiating the Limited Partnership Agreement

The largest component of the $680,000 consists of legal fees paid to outside counsel for the drafting, negotiation, and finalization of the Amended and Restated Limited Partnership Agreement of Ironside Capital Management LP (the "LPA"), dated June 14, 2016. These legal services encompassed the full scope of work necessary to establish the foundational governance and economic framework of the Partnership, including the following specific areas of the LPA:

• Structural and Governance Provisions (LPA §§ 1–12): Counsel prepared and negotiated the provisions establishing the Partnership's name, purpose, term, principal place of business, and fiscal year; the respective rights, duties, and obligations of the general partner and the limited partners; the authority and powers of the general partner in managing the affairs of the Partnership; restrictions on the limited partners' participation in management; and the procedures for meetings and consents.

• Fiduciary Duty Provisions: Counsel drafted provisions defining the fiduciary duties owed by the general partner to the limited partners, including the standards of care, exculpation, and indemnification provisions applicable to the general partner and its affiliates. These provisions required extensive negotiation to balance the interests of the general partner with those of the limited partners and to conform to the requirements of the Delaware Revised Uniform Limited Partnership Act.

• Capital Account Maintenance Rules: Counsel worked closely with Borwick Craine & Associates LLP to draft capital account maintenance provisions in compliance with Treasury Regulation § 1.704-1(b)(2)(iv), including the rules governing capital contributions, book-ups and book-downs, and the maintenance of individual capital accounts for each partner in a manner consistent with the substantial economic effect safe harbor.

• Allocation and Distribution Waterfall Provisions: Counsel prepared the Partnership's income, gain, loss, and deduction allocation provisions (LPA §§ 5.1–5.7), which include a multi-tier waterfall governing the allocation of net profits and net losses among the partners. These provisions include the management fee structure under LPA § 4.1 (providing for a management fee of 2% per annum calculated on committed capital) and the carried interest/performance allocation provisions under LPA § 5.2. The performance allocation provisions entitle the general partner to a performance-based allocation equal to 20% of net profits above an 8% preferred return to the limited partners, subject to a full catch-up provision in favor of the general partner. These allocation provisions were the subject of extensive negotiation and required careful drafting to ensure compliance with IRC §§ 704(b) and 704(c), as well as the then-applicable guidance on carried interest arrangements.

• Admission and Withdrawal Mechanics: Counsel drafted the provisions governing the admission of new limited partners (including the general partner's right to admit new limited partners at subsequent closings), the transfer of partnership interests, the withdrawal and redemption procedures (including gate provisions and lock-up periods), and the dissolution and winding-up of the Partnership.

These legal fees are quintessential organizational expenses under Treasury Regulation § 1.709-2(a), as they were incurred for "services incident to the organization of the partnership, such as negotiation and preparation of a partnership agreement." The LPA is the constitutive document of the Partnership — it creates the Partnership's legal structure, defines the economic relationship among the partners, and establishes the governance framework within which the Partnership conducts its business. The costs of preparing and negotiating this document are, by their very nature, incident to the creation of the Partnership.

2. Legal Fees for Filing, Registration, and Registered Agent

A second component of the $680,000 consists of legal fees incurred in connection with the preparation and filing of the Certificate of Limited Partnership with the Delaware Secretary of State, the filing of the Application for Authority to do business in the State of New York, and the establishment of the registered agent relationship with Capitol Statutory Services LLC at 1209 Orange Street, Wilmington, Delaware 19801. These fees include counsel's time in preparing the requisite filings, state filing fees, and the initial annual fee paid to the registered agent.

These costs fall directly within the examples of organizational expenses set forth in Treasury Regulation § 1.709-2(a), which specifically identifies "filing fees" as a qualifying organizational expense. The filing of the Certificate of Limited Partnership is the legal act by which the Partnership is brought into existence under Delaware law; the filing of the Application for Authority is the act by which the Partnership is qualified to do business in its principal state of operations. These are costs incident to the creation of the Partnership in the most literal sense.

3. Accounting and Tax Advisory Fees

The third component of the $680,000 consists of accounting and tax advisory fees paid to Borwick Craine & Associates LLP (Engagement Partner, Audit: Sandra Whitmore, CPA) for services rendered in establishing the Partnership's initial accounting and tax reporting framework. These services included, but were not limited to:

• Designing the Partnership's chart of accounts to accommodate the multi-strategy investment activities of the fund and to facilitate accurate tracking of realized and unrealized gains and losses, management fees, carried interest allocations, and operating expenses by strategy and by partner;

• Establishing the capital account methodology in accordance with Treasury Regulation § 1.704-1(b)(2)(iv), including the mechanics for tracking individual partner capital accounts, book-tax differences, and § 704(c) allocations;

• Advising on and preparing initial tax elections, including the IRC § 709(b) election to amortize organizational expenses, the election of the Partnership's taxable year and accounting method, and the consideration and documentation of elections under IRC §§ 754 and 704(c); and

• Establishing the framework for the Partnership's ongoing tax compliance obligations, including the preparation of Schedule K-1s and the reporting of allocations to partners in accordance with the terms of the LPA and applicable tax law.

These accounting and tax advisory fees are organizational expenses under Treasury Regulation § 1.709-2(a), which expressly includes "accounting fees for services incident to the organization of the partnership." The services performed by Fenwick Craine were directly related to establishing the Partnership's foundational accounting and tax infrastructure — the systems and methodologies without which the Partnership could not function as a taxable entity. These services were performed at the time of formation, were one-time in nature (as distinguished from ongoing recurring compliance services), and were incident to the creation of the Partnership.

B. Costs That Are NOT at Issue

ICM wishes to make clear for the record that costs incurred for the preparation of the private placement memorandum ("PPM"), investor presentation materials, subscription documents (including the subscription agreement and investor questionnaire), investor due diligence materials, and any fees paid to placement agents or brokers in connection with the marketing and sale of limited partnership interests were separately identified and capitalized as syndication costs under IRC § 709(a) at the time they were incurred. These syndication costs are not included in the $1,420,000 deducted under IRC § 709(b), and they have been permanently capitalized on the Partnership's books and records.

The fund's contemporaneous accounting records and the workpapers prepared by Borwick Craine & Associates LLP clearly and unambiguously segregate organizational expenses from syndication expenditures. The classification schedule enclosed as part of Exhibit D demonstrates, on a line-by-line basis, the designation of each formation-related cost as either organizational or syndication. There is no overlap, and no syndication cost has been included — whether intentionally or inadvertently — in the amounts amortized under IRC § 709(b).

C. Contemporaneous Documentation Supporting Classification

The classification of the $680,000 as organizational expenses (and, correspondingly, the classification of all syndication costs as such) was not determined after the fact or on an ex post basis. Rather, the classification was made contemporaneously with the incurrence of the costs in 2016, based on a disciplined analysis of each category of expenditure against the standards set forth in IRC § 709 and Treasury Regulation § 1.709-2. The contemporaneous nature of the classification is evidenced by the following documentation, each of which is enclosed with this response:

Board Resolutions. At the time of ICM's formation in June 2016, Ironside Capital GP LLC's managing members — Desmond R. Calloway, Founder and CIO, and Priya Venkatesh, COO and CFO — adopted formal board resolutions classifying each category of formation-related expense as either organizational or syndication. The resolutions reflect a deliberate and informed decision by the Partnership's principals to comply with the requirements of IRC § 709 and to ensure that only qualifying organizational expenses were elected for amortization under § 709(b). The resolutions are enclosed as Exhibit E.

Detailed Legal Invoices. The invoices from outside counsel retained in connection with ICM's formation contain detailed time entries and narrative descriptions of the services rendered by each attorney and paralegal on each date of service. These detailed entries permit a line-by-line classification of services rendered, distinguishing between time spent on LPA drafting and negotiation (organizational) and time spent on PPM preparation or securities compliance (syndication). The invoices are enclosed as Exhibit A and have been annotated by Borwick Craine & Associates LLP to reflect the organizational/syndication classification of each time entry.

Fenwick Craine Classification Memorandum. Borwick Craine & Associates LLP prepared a contemporaneous memorandum in 2016 (the "Classification Memorandum") documenting the allocation methodology used to classify each category of formation-related cost. The Classification Memorandum analyzes each category of expenditure against the requirements of Treasury Regulation § 1.709-2(a) and § 1.709-2(b), explains the rationale for the classification of each category, and concludes that the costs classified as organizational expenses satisfy all three requirements of the regulatory definition. The Classification Memorandum and the supporting workpapers are enclosed as Exhibit D.

The existence and quality of this contemporaneous documentation is significant. The case law has consistently recognized that contemporaneous documentation of the allocation between organizational and syndication costs is a strong indicator that the classification was made on a principled basis and is entitled to deference. See, e.g., Surloff v. Commissioner, T.C. Memo. 1995-279 (examining the quality and contemporaneity of the taxpayer's documentation in evaluating the classification of formation costs). Here, the contemporaneous documentation is extensive, detailed, and internally consistent, and it fully supports ICM's position.

IV. ITEM-BY-ITEM RESPONSE TO IDR #4

Set forth below is ICM's response to each of the eight items requested in IDR #4, together with identification of the enclosed exhibits responsive to each item.

Item 1. Request: Copies of all invoices from legal counsel relating to the formation of ICM in 2016.

Response: Enclosed as Exhibit A are copies of all invoices from outside legal counsel relating to the formation of ICM in 2016. These invoices total the relevant portion of the $1,420,000 in Formation Costs attributable to legal services. The invoices are organized chronologically, covering the period from March 2016 through August 2016, and include detailed time entries setting forth the date of service, the name and billing rate of each timekeeper, the hours expended, and a narrative description of the services rendered.

Each time entry in the enclosed invoices has been reviewed and annotated by Borwick Craine & Associates LLP to indicate whether the services described therein constitute organizational expenses or syndication costs under IRC § 709 and Treasury Regulation § 1.709-2. Entries relating to the drafting and negotiation of the LPA, the preparation of formation documents, and state filings have been designated as organizational. Entries relating to PPM preparation, securities compliance, and investor marketing materials have been designated as syndication. This annotation is consistent with the classification schedule included in Exhibit D.

We note that certain time entries have been redacted to the extent necessary to preserve attorney-client privilege and attorney work product protection, as noted in the Reservation of Rights below. In each instance, sufficient information has been provided to identify the general nature of the services rendered and to permit classification as organizational or syndication.

Item 2. Request: Copies of all invoices from accounting or financial advisors relating to the formation of ICM in 2016.

Response: Enclosed as Exhibit B are copies of all invoices from Borwick Craine & Associates LLP for accounting and tax advisory services rendered incident to the organization of ICM in 2016. These invoices cover services including, but not limited to:

• Design and implementation of the Partnership's chart of accounts, tailored to the multi-strategy investment activities of the fund;

• Preparation of tax election memoranda, including the memorandum supporting the IRC § 709(b) election, the selection of the Partnership's taxable year, and the analysis of potential elections under IRC §§ 754 and 704(c);

• Establishment of the initial capital account framework, including the methodology for tracking individual partner capital accounts in compliance with Treasury Regulation § 1.704-1(b)(2)(iv); and

• Coordination with outside counsel regarding the tax-related provisions of the LPA, including the allocation and distribution waterfall provisions.

The invoices are organized chronologically and include narrative descriptions of the services performed. All invoiced services were incident to the organization of the Partnership and are properly classified as organizational expenses.

Item 3. Request: Copy of the Limited Partnership Agreement of Ironside Capital Management LP, including all amendments.

Response: Enclosed as Exhibit C is a complete copy of the Amended and Restated Limited Partnership Agreement of Ironside Capital Management LP, dated June 14, 2016 (the "LPA"), together with all subsequent amendments thereto through the date of this response. For the Service's convenience, we draw particular attention to the following provisions of the LPA, which are referenced throughout this response and which are directly relevant to the organizational expense classification:

• LPA § 4.1 — Management Fee: Provides for a management fee payable to the general partner equal to 2% per annum, calculated on committed capital, payable quarterly in advance.

• LPA § 5.2 — Performance Allocation: Provides for a performance-based allocation (commonly referred to as "carried interest") equal to 20% of net profits above an 8% preferred return (compounded annually) to the limited partners, subject to a full catch-up provision in favor of the general partner. The performance allocation is calculated on a per-partner, per-annum basis and is subject to a high-water mark.

• LPA §§ 1–12 — Structural and Governance Provisions: Establish the formation, purpose, term, management authority, fiduciary duties, capital account maintenance, allocation and distribution mechanics, admission and withdrawal procedures, transfer restrictions, dissolution, and other fundamental terms of the Partnership.

The LPA is the constitutive document of the Partnership, and the legal fees incurred in its preparation and negotiation are the paradigmatic example of organizational expenses under Treasury Regulation § 1.709-2(a).

Item 4. Request: Any internal memoranda, analyses, or workpapers documenting the classification of formation costs as organizational expenses vs. syndication costs.

Response: Enclosed as Exhibit D are the following documents:

(i) The Borwick Craine & Associates LLP contemporaneous classification memorandum prepared in 2016 (the "Classification Memorandum"), which sets forth the methodology used to classify each category of formation-related cost, analyzes each category against the requirements of Treasury Regulation § 1.709-2(a) and (b), and documents the rationale for the organizational/syndication designation of each category;

(ii) An internal classification schedule prepared by Borwick Craine & Associates LLP (the "Classification Schedule"), which identifies each line item of formation cost by payee, invoice number, amount, date, description of services, and designation as organizational or syndication, and which reconciles the total organizational expenses to the $1,420,000 claimed under IRC § 709(b) and the total syndication costs to the amount capitalized; and

(iii) Borwick Craine & Associates LLP workpapers cross-referencing each invoice line item to the applicable provisions of IRC §§ 709 and 195 and Treasury Regulation § 1.709-2, with explanatory notes justifying the classification of each entry.

These documents constitute the Partnership's contemporaneous record of the classification analysis and provide a complete audit trail from the individual invoice line items through the aggregate amounts reported on the tax return. The Classification Memorandum, Classification Schedule, and workpapers are internally consistent and fully support ICM's position that the $680,000 at issue consists of qualifying organizational expenses.

Item 5. Request: Resolutions or minutes of the general partner approving the deduction of organizational expenses and/or the capitalization of syndication costs.

Response: Enclosed as Exhibit E are copies of the Ironside Capital GP LLC board resolutions dated June 14, 2016, signed by Desmond R. Calloway and Priya Venkatesh in their capacities as managing members of Ironside Capital GP LLC. These resolutions formally:

(a) Classify each category of formation-related expense incurred in connection with the organization of ICM as either an organizational expense or a syndication cost, consistent with the analysis set forth in the Fenwick Craine Classification Memorandum;

(b) Authorize the Partnership to make the election under IRC § 709(b)(1) to deduct and amortize organizational expenses;

(c) Direct Borwick Craine & Associates LLP, as the Partnership's tax preparer, to reflect the IRC § 709(b) election on the Partnership's initial Form 1065 and to calculate the annual amortization deduction in accordance with the 180-month amortization schedule; and

(d) Direct that all costs classified as syndication costs be permanently capitalized on the Partnership's books and records and not deducted or amortized for federal income tax purposes.

The resolutions reflect the considered judgment of the Partnership's principals, made at the time of formation and informed by the analysis and advice of the Partnership's professional advisors.

Item 6. Request: Copy of ICM's IRC § 709(b) election and the schedule of amortization of organizational expenses.

Response: Enclosed as Exhibit F are the following documents:

(i) The IRC § 709(b) election statement that was attached to ICM's initial Form 1065 for the short tax year ended December 31, 2016, in which the Partnership elected to deduct and amortize organizational expenses in accordance with IRC § 709(b)(1); and

(ii) The 180-month amortization schedule prepared by Borwick Craine & Associates LLP, which sets forth the total organizational expenses of $1,420,000, the initial $5,000 deduction taken in the year of formation (2016), the remaining balance of $1,415,000 subject to amortization, and the annual amortization deduction for each year from 2016 through 2031 (the final year of the 180-month amortization period). The schedule specifically identifies the portion of the annual amortization deduction reflected on the 2021 Form 1065, which corresponds to the twelve-month period from January 1, 2021, through December 31, 2021.

The amortization schedule demonstrates the mechanical calculation of the annual deduction and confirms that the amount reported on the 2021 Form 1065 is mathematically consistent with the 180-month amortization of the total organizational expenses.

Item 7. Request: Documentation of any private placement memorandum, subscription documents, or marketing materials prepared in connection with ICM's formation and initial capital raising.

Response: Enclosed as Exhibit G are copies of the following documents, which are provided for reference purposes only:

(i) The Confidential Private Placement Memorandum of Ironside Capital Management LP, dated June 2016;

(ii) The form of Subscription Agreement used by limited partners in connection with the initial and subsequent closings; and

(iii) The form of Investor Questionnaire used to confirm investor eligibility and suitability.

ICM emphasizes that the costs of preparing these documents — including all legal fees, printing costs, and related expenses — were classified as syndication costs under IRC § 709(a) and were permanently capitalized on the Partnership's books and records. These costs are NOT included in the $1,420,000 organizational expense deduction claimed under IRC § 709(b). The Classification Schedule enclosed as part of Exhibit D specifically identifies the costs attributable to the preparation of the PPM, subscription documents, and marketing materials and confirms their separate treatment as capitalized syndication costs.

These documents are provided solely to enable the Service to verify the segregation of syndication costs from organizational expenses and to confirm that no costs associated with the marketing or sale of partnership interests have been included in the amounts amortized.

Item 8. Request: Schedule identifying each limited partner admitted at formation and the capital commitment of each.

Response: Enclosed as Exhibit H is a schedule of the initial limited partners admitted to ICM at formation during the period from June 2016 through December 2016, showing the name of each limited partner, the date of admission, and the aggregate initial capital commitment. Certain limited partner names have been redacted in accordance with the Partnership's confidentiality obligations under the LPA; however, sufficient identifying information has been provided to enable the Service to verify the number and aggregate commitments of the initial partners.

For context, ICM's current partner roster as of December 31, 2021 — the tax year under examination — includes forty-seven (47) limited partners plus the general partner, Ironside Capital GP LLC. As of December 31, 2021, total assets under management were approximately $3.82 billion, and average committed capital for the 2021 calendar year was approximately $3.58 billion.

Consistent with information previously provided in our responses to IDRs #1 through #3, the following key limited partners are identified by name with their respective capital commitments:

• Northgate Public Employees' Retirement System — $412,000,000 commitment

• Bramblewood Family Office LLC — $95,000,000 commitment

• Marlowe Asset Management Horizon Endowment Fund — $175,000,000 commitment

These limited partners were among the initial investors admitted at formation and remain limited partners of the Partnership as of the date of this response. Their commitments are reflected on the schedule enclosed as Exhibit H.

V. SUMMARY OF ICM'S POSITION

Based on the foregoing analysis and the documentation enclosed herewith, ICM respectfully submits that the $1,420,000 in formation-year costs claimed as organizational expense deductions under IRC § 709(b) was properly classified in all respects. The entirety of the amounts claimed consists of costs incident to the creation of the Partnership itself — principally legal fees for drafting and negotiating the Limited Partnership Agreement, filing and registration fees for the formation and qualification of the Partnership, and accounting and tax advisory fees for establishing the Partnership's initial tax and accounting infrastructure. Each of these categories falls squarely within the definition of "organizational expenses" set forth in Treasury Regulation § 1.709-2(a).

The $680,000 subset questioned by the Service relates specifically to: (i) legal fees for the drafting, negotiation, and finalization of the LPA, including the structural, governance, fiduciary duty, capital account, allocation and distribution waterfall, and admission/withdrawal provisions; (ii) legal fees for the preparation and filing of the Certificate of Limited Partnership, the qualification in New York, and the establishment of the registered agent relationship; and (iii) accounting and tax advisory fees for the design of the chart of accounts, the establishment of the capital account methodology, and the preparation of initial tax elections. Each of these categories constitutes an expenditure that is (1) incident to the creation of the Partnership, (2) chargeable to capital account, and (3) of a character that would be amortized over the life of a partnership with an ascertainable life. Accordingly, each category satisfies all three requirements for classification as an organizational expense under Treasury Regulation § 1.709-2(a).

Syndication costs — including all costs related to the preparation of the private placement memorandum, subscription documents, investor marketing materials, and any placement agent or brokerage fees — were separately identified, properly classified as syndication costs under IRC § 709(a), and permanently capitalized on the Partnership's books and records. These syndication costs are not included in, and have never been included in, the $1,420,000 deducted under IRC § 709(b).

The Partnership's position is supported by multiple layers of contemporaneous documentation: formal board resolutions adopted by the general partner at the time of formation; detailed legal invoices containing narrative time entries that permit line-by-line classification; and an independent Classification Memorandum and supporting workpapers prepared by Borwick Craine & Associates LLP in 2016, documenting the allocation methodology and the rationale for the classification of each category of expense. This contemporaneous record is consistent, detailed, and unambiguous.

Accordingly, ICM respectfully submits that no reclassification of the $680,000 — or any portion thereof — from organizational expenses to syndication costs is warranted, and that the organizational expense deduction claimed on the Partnership's 2021 Form 1065 is correct as filed.

RESERVATION OF RIGHTS

ICM expressly reserves all rights, claims, and defenses available to it under applicable law, including but not limited to the right to raise additional arguments, legal theories, and factual contentions, and to submit additional documentation in support of its position, at any stage of this examination or in any subsequent administrative or judicial proceeding. Nothing in this response shall be construed as a concession, admission, or waiver of any right, claim, or defense, whether or not specifically addressed herein.

This response is not intended to waive, and shall not be deemed to waive, any applicable privilege, including without limitation the attorney-client privilege, the tax practitioner-client privilege under IRC § 7525, and the work product doctrine. Privileged materials have been excluded from the documents enclosed herewith. To the extent that any document produced in connection with this response contains or reflects information that is subject to attorney-client privilege, work product protection, or any other applicable privilege, the production of such document is inadvertent, and such inadvertent disclosure shall not constitute a waiver of the applicable privilege with respect to the disclosed document or any other document or communication. ICM requests that the Service promptly notify undersigned counsel in the event that any document produced appears to contain privileged material, so that ICM may evaluate the disclosure and take appropriate steps to preserve its privileges.

EXHIBIT LIST

The following exhibits are enclosed with this response:

We trust that the foregoing narrative responses and enclosed documentation fully address the eight items set forth in IDR #4. We remain available to discuss any questions that may arise from your review of these materials or to arrange a conference call or in-person meeting at a mutually convenient time. Please do not hesitate to contact me directly at (212) 558-4127 or lnazari@calderwoodharkness.com, or to contact Sylvia Hartwell at (212) 558-4002 or shartwell@calderwoodharkness.com.

We appreciate your professionalism and courtesy throughout this examination and look forward to resolving this matter.

Very truly yours,

CALDERWOOD & HARKNESS LLP

By: ________

Leila Nazari Lead Associate, Tax Department

Under the direction and supervision of:

________________________________________

Sylvia Hartwell Responsible Partner, Tax Department

cc: Sylvia Hartwell, Esq., Calderwood & Harkness LLP Dawn M. Petrovic, Revenue Agent, IRS Large Business & International Division Marcus Trent, Esq., General Counsel, Ironside Capital Management LP Elliot Navarro, CPA, Borwick Craine & Associates LLP

Enclosures: Exhibits A through H (as described above)

CONFIDENTIAL — This document and its enclosures contain confidential information pertaining to the federal tax examination of Ironside Capital Management LP. Distribution is limited to the addressee and persons identified in the distribution list above.

ExhibitDescription
Exhibit ALegal counsel invoices relating to the formation of ICM (March 2016 – August 2016), annotated with organizational/syndication classification
Exhibit BBorwick Craine & Associates LLP accounting and tax advisory invoices relating to the formation of ICM (2016)
Exhibit CAmended and Restated Limited Partnership Agreement of Ironside Capital Management LP (June 14, 2016), with all subsequent amendments
Exhibit DBorwick Craine & Associates LLP contemporaneous Classification Memorandum, Classification Schedule, and supporting workpapers (2016)
Exhibit EIronside Capital GP LLC board resolutions — formation expense classification and authorization of IRC § 709(b) election (June 14, 2016)
Exhibit FIRC § 709(b) election statement and 180-month amortization schedule
Exhibit GPrivate placement memorandum, form of subscription agreement, and form of investor questionnaire (provided for reference only; costs capitalized as syndication costs under IRC § 709(a))
Exhibit HSchedule of initial limited partners and capital commitments at formation (June – December 2016)