An offering statement pursuant to Regulation A relating to these securities has been filed with the United States Securities and Exchange Commission. Information contained in this Preliminary Offering Circular is subject to completion or amendment. To the extent not already qualified under Regulation A, or otherwise exempt, these securities may not be sold nor may offers to buy be accepted before the offering statement filed with the Commission is qualified. This Preliminary Offering Circular shall not constitute an offer to sell or the solicitation of an offer to buy nor may there be any sales of these securities in any state in which such offer, solicitation or sale would be unlawful before registration or qualification under the laws of any such state. We may elect to satisfy our obligation to deliver a Final Offering Circular by sending you, within two business days after the completion of our sale to you, a notice that contains the URL where the Final Offering Circular or the offering statement in which such Final Offering Circular was filed may be obtained.

PRELIMINARY OFFERING CIRCULAR DATED AUGUST 18, 2026

The Oak Companies, Inc.

5925 Carnegie Blvd, Suite 110, Charlotte, NC 28209

www.theoakcompanies.com

Up to 2,500,000 Shares of Series R Convertible Preferred Stock

An indeterminate number of shares of Class A Common Stock ($0.001 Par Value)

Issuable Upon Conversion of the Series R Preferred Stock

Selling Agent Warrants to Purchase up to 3% Shares of Common Stock

Minimum Investment: $1,000

The Company may, at its sole option, increase the size of this offering by 1,000,000 Shares ($10,000,000) for a total offering of 3,500,000 shares ($35,000,000)

See “Securities Being Offered” at Page 67

The Oak Companies, Inc., a Delaware corporation (which, together with its predecessor and the subsidiary companies described in this Offering Circular, is referred to as the “Company”) is offering up to 2,500,000 shares (the “Offering”) of the Company’s Series R Convertible Preferred Stock, par value $0.001 per share (the “Series R Preferred Stock”). The maximum offering amount may be increased up to 3,500,000 shares ($35,000,000) of Series R Preferred Stock in the sole discretion of the Company. The Series R Preferred Stock is being offered on a “best efforts” basis, which means that there is no guarantee that any amount will be sold in this Offering. The Offering will terminate at the earlier of: (a) the date at which the maximum offering amount has been sold, (b) the date at which we terminate the Offering, in our sole discretion or (c) the date that is one year from this Offering being qualified by the United States Securities and Exchange Commission (the “SEC”). The subscription funds tendered by prospective stockholders as part of the subscription process will be held in a non-interest-bearing escrow account with Wilmington Trust, National Association which is acting as the escrow agent (the “Escrow Agent”), and will not be commingled with our funds until, if and when there is a closing. See “Plan of Distribution.”

Investing in our Series R Preferred Stock is speculative and involves substantial risks. You should purchase these securities only if you can afford a complete loss of your investment. See “Risk Factors” beginning on page 9 to read about the more significant risks you should consider before buying these securities.  

Because there is no minimum dollar amount of Series R Preferred Stock that must be sold for the Offering to close, we may not receive sufficient proceeds from the Offering to execute fully and effectively on our business plan as described in this Offering Circular. If less than the maximum proceeds are available to us, our development and prospects could be adversely affected. See “Use of Proceeds to Issuer” and “Business” at pages 32 and 33, respectively, for additional details.

We intend to hold closings on no less than a monthly basis. Accordingly, the Escrow Agent will make the funds tendered available to us, and we will issue the shares of Series R Preferred Stock to investors, on no less than a monthly basis.

The SEC does not pass upon the merits of or give its approval to any securities offered or the terms of the Offering, nor does it pass upon the accuracy or completeness of any Offering Circular or other solicitation materials. These securities are offered pursuant to an exemption from registration with the SEC; however, the SEC has not made an independent determination that the securities offered are exempt from registration.

Generally, no sale may be made to you in this Offering if the aggregate purchase price you pay is more than 10% of the greater of your annual income or net worth. Different rules apply to accredited investors and non-natural persons. Before making any representation that your investment does not exceed applicable thresholds, we encourage you to review Rule 251(d)(2)(i)(c) of Regulation A. For general information on investing, we encourage you to refer to www.investor.gov.

Sales of these securities will commence on approximately ●, 2026.

The Company is following the “Offering Circular” format of disclosure under Regulation A.

If we become a reporting company under the Securities Exchange Act of 1934, as amended (the “Exchange Act”), we intend to take advantage of the provisions that relate to “emerging growth companies” under the Jumpstart our Business Startups (“JOBS”) Act of 2012. See “Ongoing Reporting and Where to Find Additional Information – Future Implications of Being an Emerging Growth Company.”

TABLE OF CONTENTS

The “Company,” “we,” “us,” “The Oak Companies,” and “our” means, collectively, The Oak Companies, Inc. and, when applicable, its predecessor company, Red Oak Capital Holdings, LLC (“ROCH” or the “Predecessor”).

This Offering Circular may contain forward-looking statements and information relating to, among other things, the Company, its business plan and strategy, its expectations regarding the additional revenues and the increased profit margins that might be achieved from facilities developed with the proceeds of this Offering and its industry. These forward-looking statements are based on the beliefs of, assumptions made by, and information currently available to our management. When used in the Offering materials, the words “estimate,” “project,” “believe,” “anticipate,” “intend,” “expect” and similar expressions are intended to identify forward-looking statements, which constitute forward looking statements. These statements reflect management’s current views with respect to future events and are subject to risks and uncertainties that could cause our actualsee results to differ materially from those contained in the forward-looking statements. Investors are cautioned not to place undue reliance on these forward-looking statements, which speak only as of the date on which they are made. We do not undertake any obligation to revise or update these forward-looking statements to reflect events or circumstances after such date or to reflect the occurrence of unanticipated events.

RISK FACTORS

 An investment in our Series R Preferred Stock involves various risks and uncertainties. You should carefully consider the following risk factors in conjunction with the other information contained in this Offering Circular before purchasing our Series R Preferred Stock. The risks discussed in this Offering Circular can adversely affect our business, operating results, prospects, and financial condition. These risks could cause the value of our Series R Preferred Stock to decline and could cause you to lose all or part of your investment. The risks and uncertainties described below are not the only ones we face but do represent those risks and uncertainties that we believe are material to our business, operating results, prospects, and financial condition. Additional risks and uncertainties not presently known to us or that we currently deem immaterial may also harm our business. The risks discussed below assume the Reorganization has been consummated and that the Company has succeeded to the business of the Predecessor.

Risks Related to this Offering and the Series R Preferred Stock

There is currently no public trading market for the Series R Preferred Stock and there may never be one; therefore, it will be difficult for you to sell your Series R Preferred Stock.

There is currently no public market for the Series R Preferred Stock and there may never be one. You may not sell your Series R Preferred Stock unless the buyer meets the requirements and can make the representations contained in “Plan of Distribution – Investment Limitations.” If you are able to sell your Series R Preferred Stock, you will likely have to sell them at a substantial discount to the price you paid for the Series R Preferred Stock. It also is likely that your Series R Preferred Stock would not be accepted as the primary collateral for a loan. You should purchase the Series R Preferred Stock only as a long-term investment because of the illiquid nature of the Series R Preferred Stock.

The SEC does not pass upon the merits of, or give approval to, the Series R Preferred Stock.

The Series R Preferred Stock is being offered pursuant to an exemption from federal securities registration under Regulation A. While the SEC reviews and qualifies Regulation A offering statements, the SEC does not pass upon the merits of or give its approval to any securities offered or the terms of the Offering, nor does it pass upon the accuracy or completeness of this Offering Circular. The SEC has not made an independent determination that the securities offered are exempt from registration. Therefore, prospective investors must assess the adequacy of disclosure and the fairness of the terms of this Offering on their own or in conjunction with their personal advisors.

We are not required to raise any minimum amount in this Offering before we may utilize the funds received in this Offering. Investors should be aware that there is no assurance that any monies beside their own will be invested in this Offering.

Because there is no minimum amount of subscriptions which we must receive before accepting funds in the Offering, you will not be assured that we will have sufficient funds to execute our business plan or satisfy its working capital requirements and will bear the risk that we will be unable to secure the funds necessary to meet our current and anticipated financial obligations.

This offering is being conducted on a “best efforts” basis without a minimum and we may not be able to execute our growth strategy if the maximum is not sold.

If you invest in this Offering and less than all of the offered Shares are sold, the risk of losing your entire investment will be increased. We are offering the Series R Preferred Stock on a “best efforts” basis without a minimum, and we can give no assurance that all of the offered Series R Preferred Stock will be sold. If less than maximum offering amount is sold, we may be unable to fund all the intended uses described in this Offering Circular from the net proceeds anticipated from this Offering without obtaining funds from alternative sources or using working capital that we generate. Alternative sources of funding may not be available to us at what we consider to be a reasonable cost, and the working capital generated by us may not be sufficient to fund any uses not financed by offering net proceeds. No assurance can be given to you that any funds will be invested in this Offering other than your own.

This Offering involves “rolling closings,” which may mean that earlier investors may not have the benefit of information that later investors have.

We may conduct a closing at any time and from time to time. At that point, investors whose Subscription Agreements have been accepted will become stockholders in the Company. From time to time, we may file supplements to our Offering Circular reflecting material changes and investors whose subscriptions have not yet been accepted will have the benefit of that additional information. These investors may withdraw their subscriptions and get their money back. Investors whose subscriptions have already been accepted, however, will already be stockholders of the Company and will have no such right.

We may terminate this Offering at any time during the Offering period.

We reserve the right to terminate this Offering at any time, regardless of the number of shares of Series R Preferred Stock sold. In the event that we terminate this Offering at any time prior to the sale of all of the Series R Preferred Stock offered hereby, whatever amount of capital that we have raised at that time will have already been utilized by the Company and no funds will be returned to investors.

Management has broad discretion in using the proceeds from this Offering.

We plan to use the proceeds from this Offering to retire bonds issued by ROCF IV Series and other select bond obligations of the Sponsored Funds, as well as to fund business operations and working capital of the Company generally. However, we have broad discretion in the application of proceeds and the timing of the expenditure of the proceeds of this Offering. If we fail to apply the proceeds effectively, we may not be successful in implementing our business plan. You will not have the opportunity to evaluate all of the economic, financial or other information upon which we base our decisions.

Using a credit card to purchase shares of Series R Preferred Stock may impact the return on your investment as well as subject you to other risks inherent in this form of payment.

Investors in this Offering have the option of paying for their investment with a credit card, which is not usual in the traditional investment markets. Transaction fees charged by your credit card company (which can reach 5% of transaction value if considered a cash advance) and interest charged on unpaid card balances (which can reach or exceed 25% in some states) add to the effective purchase price of the shares of Series R Preferred Stock you buy. The cost of using a credit card may also increase if you do not make the minimum monthly card payments and incur late fees.

Using a credit card is a relatively new form of payment for securities and will subject you to other risks inherent in this form of payment, including that, if you fail to make credit card payments (e.g. minimum monthly payments), you risk damaging your credit score and payment by credit card may be more susceptible to abuse than other forms of payment. Moreover, where a third-party payment processor is used, as in this offering, your recovery options in the case of disputes may be limited.

The increased costs due to transaction fees and interest may reduce the return on your investment. The SEC’s Office of Investor Education and Advocacy issued an Investor Alert dated February 14, 2018 entitled Credit Cards and Investments – A Risky Combination, which explains these and other risks you may want to consider before using a credit card to pay for your investment.

We may amend our business policies without stockholder approval.

Our Board of Directors (the “Board”) determines our growth, investment, financing, capitalization, borrowing, operations and distributions policies. Although our Board has no intention at present to change or reverse any of these policies, they may be amended or revised without notice to you as a holder of our Series R Preferred Stock. Accordingly, holders of our Series R Preferred Stock will not have any control over changes in our policies. We cannot assure you that changes in our policies will serve fully the interests of all holders of our Series R Preferred Stock.

We cannot assure you that dividends on, or any other payments in respect of, the Series R Preferred Stock will be made timely or at all.

We cannot assure you that we will be able to pay the accrued dividends on the Series R Preferred Stock or to redeem the Series R Preferred Stock. While dividends on the Series R Preferred Stock will accrue and are cumulative, dividends, if and when required to be paid, will be paid only from our funds legally available for such purpose. You should be aware that certain factors may influence our decision, or adversely affect our ability, to pay such accrued dividends on, or make other payments in respect of, the Series R Preferred Stock, including, among other things:

The Series R Preferred Stock are perpetual equity interests and are subordinate to our and our subsidiaries’ existing and future indebtedness and other liabilities, including the existing and future indebtedness and other liabilities of the Sponsored Funds.

The Series R Preferred Stock are perpetual equity interests and do not constitute indebtedness. As such, the Series R Preferred Stock will rank junior to all of our and our subsidiaries’ indebtedness and other liabilities (and any capital stock ranking senior to the Series R Preferred Stock we may issue in the future), including those of the Sponsored Funds, with respect to assets available to satisfy our claims, including in our liquidation, dissolution or winding up. Further, unlike indebtedness, where principal and interest would customarily be payable on specified due dates, in the case of preferred stock such as the Series R Preferred Stock, we are not obligated to redeem the Series R Preferred Stock or otherwise make any payments on the Stated Value of the Series R Preferred Stock until the occurrence of certain events. As a result, holders of the Series R Preferred Stock may be required to bear the financial risks of an investment in the Series R Preferred Stock for an indefinite period of time.

Holders of our Series R Preferred Stock will have no rights as common stockholders until such holders convert their Series R Preferred Stock into shares of our common stock.

Holders of our Series R Preferred Stock will have no rights with respect to the shares of our common stock underlying such shares, such as voting rights, unless and until such holders acquire the shares of our Class A common stock issuable upon conversion of such shares. Our Class A common stock is the only class or series of our stock carrying full voting rights. Holders of Series R Preferred Stock have no voting rights with respect to amendments to our certificate of incorporation (including the Designation establishing the Series R Preferred Stock) or with respect to any matter which could materially or adversely affects the rights of the holders of Series R Preferred Stock. Upon conversion, holders will be entitled to exercise the rights of a common stockholder only as to matters for which the record date occurs after the date on which the Class A Common Stock is deemed issued upon such conversion.

Holders of our Series R Preferred Stock will be subject to certain transfer restrictions following the conversion of their Series R Preferred Stock into shares of our common stock.

As a condition to the issuance of the Series R Preferred Stock, each purchaser of Series R Preferred Stock will be subject to certain lock-up provisions, which provisions will provide that, during the period commencing on the date of the final prospectus or offering circular relating to such Listing Event and ending on the date specified by the managing underwriter or lead placement agent (not to exceed 90 days from the date of such final prospectus or offering circular), such purchaser will not: (a) lend, offer, pledge, sell, contract to sell, sell any option or contract to purchase, purchase any option or contract to sell, grant any option, right or warrant to purchase, or otherwise transfer or dispose of, directly or indirectly, any shares of Common Stock received upon conversion of the Series R Preferred Stock held immediately prior to the effectiveness of the registration statement or offering statement for such Listing Event; or (b) enter into any swap or other arrangement that transfers to another, in whole or in part, any of the economic consequences of ownership of any shares of Common Stock received upon conversion of the Series R Preferred Stock. Accordingly, upon a Listing Event, holders of Series R Preferred Stock will not be able to freely sell the shares of Common Stock received in connection with such Listing Event for a period of up to 90 days, and will be subject to any market volatility with respect to such shares of Common Stock during such period with limited recourse as to ameliorative measures to protect their investment. For a more detailed description of the lock-up provisions and conversion rights, see “Securities Being Offered” and “Description of Capital Stock.”

The amount of the Stated Value is fixed and holders of Series R Preferred Stock will have no right to receive any greater payment.

The payment due upon liquidation is fixed at the Stated Amount, plus an amount equal to accrued dividends thereon, if any, to, but not including the date of payment. If, in the case of our liquidation, there are remaining assets to be distributed after payment of this amount, you will have no right to receive or to participate in these amounts.

The Series R Preferred Stock has not been rated.

The Series R Preferred Stock has not been rated by any nationally recognized statistical rating organization, which may negatively affect its value and your ability to sell your Series R Preferred Stock. No assurance can be given, however, that one or more rating agencies might not independently determine to issue such a rating or that such a rating, if issued, would not adversely affect the value of the Series R Preferred Stock. In addition, we may elect in the future to obtain a rating of the Series R Preferred Stock, which could adversely impact the value of the Series R Preferred Stock. Ratings only reflect the views of the rating agency or agencies issuing the ratings and such ratings could be revised downward or withdrawn entirely at the discretion of the issuing rating agency if in its judgment circumstances so warrant. Any such downward revision or withdrawal of a rating could have an adverse effect on the value of the Series R Preferred Stock.

You may owe taxes on “phantom” dividend income even if you do not receive any cash.

Under federal tax rules, if the amount you would receive when your shares are redeemed exceeds the price you paid for them by more than a minimal amount, you may be treated as receiving a taxable “deemed dividend” even though you have not actually received any cash. This deemed dividend would be spread out and taxed over the period you hold your shares. To the extent we have earnings and profits, this amount would be taxed as ordinary dividend income. If there are also unpaid dividends when your shares are redeemed, the IRS may treat those amounts as additional taxable income under these rules as well. We will determine whether a deemed dividend exists, and our determination is binding on you for tax purposes unless you disclose a different position on your tax return. You should consult your tax advisor about how these rules may apply to your investment.

Our Board has the authority, without stockholder approval, to issue common and preferred stock that could dilute the value of your Series R Preferred Stock and perpetuate their control over us.

Our certificate of incorporation allows us to issue shares of common or preferred stock without any vote or further action by our stockholders. Our Board has the authority to fix and determine the relative rights and preferences of preferred stock. Pursuant to this authority, our Board has authorized two other series of preferred stock and could authorize additional series of preferred stock in the future. Such preferred stock, if issued, would grant to holders the preferred right to our assets upon liquidation, the right to receive dividend payments before dividends are distributed to the holders of other securities and the right to the redemption of the shares, together with a premium, prior to the redemption of our other securities, including the Series R Preferred Stock. Such issuance also would dilute your ownership interest in the Company. See Dilution and Securities Being Offered.

We cannot assure you that we will be able to redeem or convert your Series R Preferred Stock.

Our ability to redeem your Series R Preferred Stock is dependent on our ability to operate profitably and to generate cash from our operations or from raising additional capital. We cannot guarantee that we will be able to redeem your Series R Preferred Stock or that we will list our common stock, which is the only time your Series R Preferred Stock will convert into shares of our common stock.

We may issue additional debt and equity securities, which are senior to your Series R Preferred Stock as to distributions and in liquidation, which could materially adversely affect the value of your Series R Preferred Stock.

In the future, we may attempt to increase our capital resources by entering into additional debt or debt-like financing that is secured by all or up to all of our assets, or issuing debt or equity securities, which could include issuances of commercial paper, medium-term notes, senior notes, subordinated notes or shares. In the event of our liquidation, our lenders and holders of our debt securities would receive a distribution of our available assets before distributions to our stockholders. Any preferred securities, if issued by us, may have a preference with respect to distributions and upon liquidation that is senior to the preference of the Series R Preferred Stock, which could further limit our ability to make distributions to our stockholders. Because our decision to incur debt and issue securities in our future offerings will depend on market conditions and other factors beyond our control, we cannot predict or estimate the amount, timing or nature of our future offerings and debt financing.

Further, market conditions could require us to accept less favorable terms for the issuance of our securities in the future. Thus, you will bear the risk of our future offerings reducing the value of your Series R Preferred Stock. In addition, we can change our leverage strategy from time to time without approval of our stockholders, which could materially adversely affect the value of your Series R Preferred Stock.

Certain provisions of Delaware law and our certificate of incorporation may make it more difficult for a third party to effect a change-of-control.

Our certificate of incorporation authorizes our Board to issue up to a certain number of shares of preferred stock. The preferred stock may be issued in one or more series, the terms of which may be determined at the time of issuance by our Board without further action by the stockholders. These terms may include voting rights including the right to vote as a series on particular matters, preferences as to dividends and liquidation, conversion rights, redemption rights and sinking fund provisions. The issuance of any preferred stock could diminish the rights of holders of existing shares, including the Series R Preferred Stock, and therefore could reduce the value of such shares. In addition, specific rights granted to future holders of preferred stock could be used to restrict our ability to merge with, or sell assets to, a third party. The ability of our Board to issue preferred stock could make it more difficult, delay, discourage, prevent or make it costlier to acquire or effect a change-in-control, which in turn could prevent our stockholders from recognizing a gain in the event that a favorable offer is extended and could materially and negatively affect the value of our securities. In addition, certain provisions of Delaware law, such as Section 203 of the Delaware General Corporation Law, also may make more difficult or discourage persons from attempting to acquire the Company and could adversely affect the value of the Series R Preferred Stock or the Class A Common Stock into which it might convert. See Securities Being Offered.

Risks Related to Our Business

We have incurred a net loss to date, have an accumulated deficit, and our operations will not be profitable in 2026.

We incurred a net loss attributable to our Predecessor of approximately $30.7 million for the fiscal year ended December 31, 2025. Our accumulated deficit was approximately $128.7 million as of December 31, 2025. We will not be profitable in 2026 and there is no guarantee that we will be profitable in the future.

We are a parent company and accordingly we are dependent upon distributions from our subsidiaries to pay taxes and other expenses.

We are a parent company and our principal assets are our direct and indirect subsidiaries, including the Sponsored Funds, ROGP, and Red Oak Financial. As a result, we are heavily reliant on our subsidiaries to generate revenues, and our ability to pay taxes and other expenses is dependent on the ability of such subsidiaries to make distributions or other payments to us. The obligations of the Sponsored Funds, ROGP, and Red Oak Financial, as well as certain laws and regulations that may apply to such entities, may result in restrictions on their ability to make distributions to us. To the extent that we need funds, and our subsidiaries are restricted from making such distributions or payments, we may not be able to obtain such funds on terms acceptable to us or at all and as a result could suffer an adverse effect on our liquidity and financial condition.

We are structurally subordinated to the existing and future indebtedness of our subsidiaries, including the Sponsored Funds.

The obligations of the Sponsored Funds, ROGP, and Red Oak Financial, as well as certain laws and regulations that may apply to such entities, may restrict their ability to make distributions to us. The Sponsored Funds are separate legal entities with their own independent third-party indebtedness or other contractual liabilities. As a result, our right to receive any cash or assets from a Sponsored Fund upon its liquidation, reorganization, or through standard operational distributions is structurally subordinated to the prior claims of that Sponsored Fund’s secured and unsecured creditors. In the event of financial distress, insolvency, or bankruptcy of a Sponsored Fund, its assets will be used to satisfy its own obligations first. The agreements entered into by our Sponsored Funds with respect to their indebtedness may contain strict financial covenants that prohibit or restrict the fund from making cash distributions, paying management fees, or returning capital to us if they fail to meet certain debt-service coverage ratios or if an event of default occurs. Our business model relies upon further sponsorship of additional Sponsored Funds and expanding our other product lines to grow fee revenues. If new Sponsored Funds are unable to successfully raise capital, or we are unable to expand our other product lines, we will not grow as anticipated, which would have a material adverse effect on our financial condition.

We may not realize the anticipated benefits from the Reorganization.

The benefits that we expect to achieve as a result of the Reorganization will depend, in part, on our ability to realize anticipated cost savings and synergies. Following the Reorganization, we believe that we will be able to, among other things, streamline administrative and general corporate functions and implement and maintain a capital structure designed to meet our specific needs. A variety of risks could cause us not to realize some or all of the expected benefits. These risks include the creation of a new organizational structure, changes in processes and information systems, dis-synergies from the Reorganization and changes to our operating model. Even if we are able to execute this transition successfully, this may not result in the full realization of the benefits that we currently expect, either within the expected time frame, or at all. In addition, the costs to achieve the anticipated benefits may be higher than we currently anticipate.

The historical combined financial information included in this Offering Circular is not necessarily representative of the results that we would have achieved as a reorganized company and may not be indicative of future results.

The historical combined financial information in this Offering Circular may not reflect our business’ results of operations, financial position and cash flows had the Reorganization occurred prior to the periods presented and may not be indicative of those that we will achieve following the Reorganization. Actual financial results that would have been achieved if the Reorganization occurred prior to the periods presented would depend on multiple factors, including the integration of functions and processes across our business, changes in our personnel needs, tax structure, financing and business operations, changes in our financial resources and sources and cost of capital and our need to enter into agreements as a reorganized company. As a result, such historical combined financial information is not necessarily representative of our results of operations or financial condition had the Reorganization occurred prior to the periods presented and may not be indicative of our results of operations or financial condition for any future period.

We have incurred, and expect to continue to incur, significant transaction costs in connection with the Reorganization.

In connection with the Reorganization, we have incurred and expect to continue to incur significant costs and expenses, including financial advisory, legal, accounting, consulting and other advisory fees and expenses, reorganization and restructuring costs and other related expenses. We are not able to quantify the exact amount of these expenses or the period in which they will be incurred. Some of the factors affecting the costs associated with the Reorganization include the timing of the completion of the Reorganization, the structure and execution of the Reorganization and the resources required to transition and integrate post-Reorganization. There may also be additional unanticipated significant costs in connection with the Reorganization that we do not currently anticipate. These costs and expenses could reduce the benefits we expect to achieve from the Reorganization.

We depend on information technology systems and face cybersecurity risks that could harm our business, result in the loss of confidential information, and expose us to significant legal and financial liability.

Our business operations rely on information technology systems to process, transmit, and store electronic information, and to manage or support our loan origination, underwriting, asset management, and servicing workflows. A failure, interruption, or breach of our information technology systems could result in failures or disruptions in our lending activities, borrower and investor relationship management, general ledger, and other systems. Our systems are vulnerable to damage or interruption from circumstances beyond our control, including fire, natural disasters, systems failures, viruses, and security breaches.

We collect, process, and retain sensitive and confidential information regarding our borrowers, investors, and business partners, including personally identifiable information, financial data, and proprietary business information. Despite our security measures, our systems may be vulnerable to cyberattacks or breached due to employee error, malfeasance, or other disruptions. Cyberattacks are becoming more sophisticated and include malicious software, unauthorized access attempts, denial of service attacks, and ransomware. The techniques used to obtain unauthorized access change frequently, and we may not be able to anticipate or implement adequate preventive measures against all such threats. Any security breach could expose us to litigation, regulatory investigations, significant fines and penalties, disruption of operations, reputational harm, and other material adverse effects. We rely on third-party service providers for certain information technology, data processing, and operational functions. Any failure or breach of these third parties’ systems could have a material adverse effect on our business, and we may not be fully indemnified for resulting losses. We are also subject to various federal, state, and local laws and regulations relating to the collection, use, retention, security, and transfer of personal information. These laws are evolving and may be interpreted in ways inconsistent with our current practices or require us to incur significant compliance costs. Failure to comply could result in civil or criminal penalties, litigation, and reputational harm. Although we maintain insurance coverage for certain cybersecurity risks, such coverage may be insufficient to cover all losses or claims that may arise, and we cannot be certain that coverage will continue to be available on economically reasonable terms.

Risks Related to Conflicts of Interest

Certain of our officers and key personnel will face competing demands relating to their time and will face conflicts of interest related to their obligations to affiliated entities, which could cause our business to suffer.

Certain of our officers and key personnel have interests in other programs and engage in other business activities, including with respect to certain of our affiliates such as White Oak Capital Holdings, LLC. As a result, they will have conflicts of interest in allocating their time between us and such other programs and activities in which they are involved. Because these persons have competing interests on their time and resources, they may have conflicts of interest in allocating their time between our business and these other activities. Should our officers and key personnel not balance these competing demands on their time and resources, our business could suffer. During times of intense activity in other programs and ventures, they may devote less time and fewer resources to our business than are necessary or appropriate to manage our business. We expect that as our activities expand, we will attempt to hire additional employees who would devote substantially all of their time to our business.

Our executive officers face conflicts of interest relating to the making of investments, and such conflicts may not be resolved in favor of the Sponsored Funds, which could limit investment opportunities in which we have an equity interest, impair our ability to make distributions and reduce the value of your investment.

We have sponsored, and may sponsor in the future, programs that have investment objectives similar to the Sponsored Funds. We rely on our executive officers to identify suitable investment opportunities for our SMAs and the Sponsored Funds, and we may be making investments on behalf of the SMAs at the same time as such Sponsored Funds. Therefore, our executive officers could be subject to conflicts of interest between the SMAs and the Sponsored Funds. Many investment opportunities would be suitable for the SMAs as well as the Sponsored Funds. Such events could result in our investing in assets that provide less attractive returns to the Sponsored Funds in which we have an equity interest, impairing the value of your investment.

We may from time to time acquire loans from existing or future entities or programs that we sponsor.

Part of our business strategy will likely include the purchase of existing and performing first mortgage loans, which could include loans held by entities or programs that we sponsor. In such an instance, we would anticipate that we would purchase the loan for the face amount of the principal then outstanding on the loan. We cannot guarantee that this is the lowest price for which the loan could be purchased. As a result, we may acquire these loans for a premium to fair market value.

Risks Related to Our Lending and Investment Activities

Our loans and investments expose us to risks associated with debt-oriented real estate investments generally.

We seek to invest primarily in debt instruments relating to real estate-related assets. As such, we are subject to, among other things, risk of defaults by borrowers in paying debt service on outstanding indebtedness and to other impairments of our loans and investments. Any deterioration of real estate fundamentals generally, and in the U.S. in particular, could negatively impact our performance by making it more difficult for borrowers of our mortgage loans, or borrower entities, to satisfy their debt payment obligations, increasing the default risk applicable to borrower entities, and/or making it more difficult for us to generate attractive risk-adjusted returns. Changes in general economic conditions will affect the creditworthiness of borrower entities and/or the value of underlying real estate collateral relating to our investments and may include economic and/or market fluctuations, changes in environmental, zoning and other laws, casualty or condemnation losses, regulatory limitations on rents, decreases in property values, changes in the appeal of properties to tenants, changes in supply and demand, fluctuations in real estate fundamentals, the financial resources of borrower entities, energy supply shortages, various uninsured or uninsurable risks, natural disasters, political events, terrorism and acts of war, changes in government regulations, changes in real property tax rates and/or tax credits, changes in operating expenses, changes in interest rates, changes in inflation rates, changes in the availability of debt financing and/or mortgage funds which may render the sale or refinancing of properties difficult or impracticable, increased mortgage defaults, increases in borrowing rates, negative developments in the economy and/or adverse changes in real estate values generally and other factors that are beyond our control.

We cannot predict the degree to which economic conditions generally, and the conditions for real estate debt investing in particular, will improve or decline. Any declines in the performance of the U.S. and global economies or in the real estate debt markets could have a material adverse effect on our business, financial condition, and results of operations.

Commercial real estate-related investments that are secured by real property are subject to delinquency, foreclosure, and loss, which could result in losses to us.

Commercial real estate debt instruments (e.g., mortgages) that are secured by commercial property are subject to risks of delinquency and foreclosure and risks of loss that are greater than similar risks associated with loans made on the security of single-family residential property. The ability of a borrower to repay a loan secured by an income-producing property typically is dependent primarily upon the successful operation of the property rather than upon the existence of independent income or assets of the borrower. If the net operating income of the property is reduced, the borrower’s ability to repay the loan may be impaired. Net operating income of an income-producing property can be affected by, among other things:

Specifically, changes in federal, state, and local laws and regulations may affect certain income producing properties more than others. Any change to the federal, state, and local regulations applicable to this industry may negatively affect the ability of the property owner to produce income and materially diminish the value of the property used to secure the loan. In addition, we are exposed to the risk of judicial proceedings with our borrowers and entities we invest in, including bankruptcy or other litigation, as a strategy to avoid foreclosure or enforcement of other rights by us as a lender or investor.

In the event that any of the properties or entities underlying or collateralizing our loans or investments experiences any of the foregoing events or occurrences, the value of, and return on, such investments could be reduced, which would adversely affect our results of operations and financial condition.

Fluctuations in interest rates and credit spreads could reduce our ability to generate income on our loans and other investments, which could lead to a significant decrease in our results of operations, cash flows and the market value of our investments and may limit our ability to pay distributions to our stockholders.

Our primary interest rate exposures relate to the yield on our loans and the financing cost of our debt. Changes in interest rates and credit spreads may affect our net income from loans, which is the difference between the interest and related income we earn on our interest-earning investments and the interest and related expense we incur in financing these investments. Interest rate and credit spread fluctuations resulting in our interest and related expense exceeding interest and related income would result in operating losses for us. Changes in the level of interest rates and credit spreads also may affect our ability to make loans or investments, the value of our loans and investments and our ability to realize gains from the disposition of assets. Increases in interest rates and credit spreads may also negatively affect demand for loans and could result in higher borrower default rates. The U.S. Federal Reserve began reducing rates in September 2024 as inflation concerns lessened. During 2025, the U.S. Federal Reserve made three additional interest rate reductions and has not made any projections of further rate changes for 2026; however, the forward yield curve indicates that further reductions are expected.

Our operating results depend, in part, on differences between the income earned on our investments and our financing costs. The yields we earn on our floating-rate assets and our borrowing costs tend to move in the same direction in response to changes in interest rates. However, one can rise or fall faster than the other, causing our net interest margin to expand or contract. In addition, we could experience reductions in the yield on our investments and an increase in the cost of our financing. Although we seek to match the terms of our liabilities to the expected lives of loans that we acquire or originate, circumstances may arise in which our liabilities are shorter in duration than our assets, resulting in their adjusting faster in response to changes in interest rates. For any period during which our investments are not match-funded, the income earned on such investments may respond more slowly to interest rate fluctuations than the cost of our borrowings. Consequently, changes in interest rates, particularly short-term interest rates, may immediately and significantly decrease our results of operations and cash flows and the market value of our investments, and any such change may limit our ability to pay distributions to our stockholders. In addition, unless we enter into hedging or similar transactions with respect to the portion of our assets that we fund using our balance sheet, returns we achieve on such assets will generally increase as interest rates for those assets rise and decrease as interest rates for those assets decline. 

We operate in a competitive market for lending and investment opportunities which may intensify, and competition may limit our ability to originate or acquire desirable loans and investments or dispose of assets we target and could also affect the yields of these assets and have a material adverse effect on our business, financial condition, and results of operations.

We operate in a competitive market for lending and investment opportunities, which may intensify. Our profitability depends, in large part, on our ability to originate or acquire our target assets on attractive terms. In originating or acquiring our target assets, we compete for opportunities with a variety of lenders and investors, including REITs, specialty finance companies, public and private funds (including funds managed by affiliates of our Sponsor), commercial and investment banks, commercial finance and insurance companies and other financial institutions. Some competitors may have a lower cost of funds and access to funding sources that are not available to us, such as the U.S. Government. Many of our competitors are not subject to the operating constraints associated with maintaining an exclusion from regulation under the Investment Company Act. In addition, some of our competitors may have higher risk tolerances or different risk assessments, which could allow them to consider a wider variety of loans and investments, offer more attractive pricing or other terms and establish more relationships than us. Furthermore, competition for originations of and investments in our target assets may lead to decreasing yields, which may further limit our ability to generate desired returns. Also, as a result of this competition, desirable loans and investments in our target assets may be limited in the future and we may not be able to take advantage of attractive lending and investment opportunities from time to time, thereby limiting our ability to identify and originate or acquire loans or make investments that are consistent with our investment objectives. We cannot assure you that the competitive pressures we face will not have a material adverse effect on our business, financial condition, and results of operations.

Prepayment rates and difficulty redeploying proceeds may adversely affect our financial performance.

Our borrowers may be able to repay their loans prior to their stated maturities. In periods of declining interest rates or credit spreads, prepayment rates on loans generally increase. If general interest rates or credit spreads decline at the same time, the proceeds of such prepayments may not be reinvested for some period of time or may be reinvested in assets yielding less than the prepaid assets. Prepayment rates may be affected by the current level of interest rates and credit spreads, availability of mortgage credit, economic vitality of the area in which properties are located, servicing of the loans, possible tax law changes, other investment opportunities, and other economic, social, geographic, demographic, and legal factors beyond our control. As our loans and investments are repaid, we will look to redeploy proceeds into new investments, but we may fail to identify reinvestment options that provide comparable returns or risk profiles. If we fail to redeploy proceeds effectively, our financial performance and our ability to fulfill our obligations related to the Series R Preferred Stock will suffer.

The lack of liquidity in certain of our assets may adversely affect our business.

The illiquidity of certain of our assets may make it difficult for us to sell such investments if the need or desire arises. Certain assets such as mortgages and other loans are relatively illiquid investments due to their short life, their potential unsuitability for securitization and the greater difficulty of recovery in the event of a borrower’s default. In addition, certain of our investments may become less liquid after our investment as a result of periods of delinquencies or defaults or turbulent market conditions, which may make it more difficult for us to dispose of such assets at advantageous times or in a timely manner. Moreover, many of the loans and securities we invest in are not registered under the relevant securities laws, resulting in limitations or prohibitions against their transfer, sale, pledge, or their disposition except in transactions that are exempt from registration requirements or are otherwise in accordance with such laws. As a result, many of our investments are illiquid, and if we are required to liquidate all or a portion of our portfolio quickly, for example as a result of margin calls, we may realize significantly less than the value at which we have previously recorded our investments. Further, we may face other restrictions on our ability to liquidate an investment to the extent that we have or could be attributed as having material, non-public information regarding the borrower entity. As a result, our ability to vary our portfolio in response to changes in economic and other conditions may be relatively limited, which could adversely affect our results of operations, financial condition, and ability to fulfill our obligations related to the Series R Preferred Stock.

We are subject to additional risks associated with priority loan participations.

Some of our loans may be participation interests in which we share the rights, obligations, and benefits of the loan with other lenders. From time to time these participations may be structured so that other participants have a priority to payments of interest and principal over us, or, in other words, our rights to payments of interest and principal will be subordinate to the satisfaction of the priority rights of those participants. In such cases, if a borrower defaults on a participation loan, or if the borrower is in bankruptcy, our interest in the participation loan will be satisfied only after the interests of the other lenders in the participation loan are satisfied. In those instances, our risk of loss is greater than the risk associated with those participants with priority over our other loans. If the underlying collateral is insufficient to pay-off the other participating lenders, then we may experience losses that would have a material adverse effect on our operations.

Any distressed loans or investments we make, or loans and investments that later become distressed, may subject us to losses and other risks relating to bankruptcy proceedings.

While our loans and investments focus primarily on “performing” real estate-related interests, our loans and investments may also include making distressed investments from time to time (e.g., investments in defaulted, out-of-favor or distressed loans and debt securities) or may involve investments that become “sub-performing” or “non-performing” following our acquisition thereof. Certain of our investments may include properties that typically are highly leveraged, with significant burdens on cash flow and, therefore, involve a high degree of financial risk. During an economic downturn or recession, loans or securities of financially or operationally troubled borrowers or issuers are more likely to go into default than loans or securities of other borrowers or issuers. Loans or securities of financially or operationally troubled issuers are less liquid and more volatile than loans or securities of borrowers or issuers not experiencing such difficulties. The market prices of such securities are subject to erratic and abrupt market movements and the spread between bid and ask prices may be greater than normally expected. Investment in the loans or securities of financially or operationally troubled borrowers or issuers involves a high degree of credit and market risk.

In certain limited cases (e.g., in connection with a workout, restructuring and/or foreclosing proceedings involving one or more of our investments), the success of our investment strategy will depend, in part, on our ability to effectuate loan modifications and/or restructure and improve the operations of our borrower entities. The activity of identifying and implementing successful restructuring programs and operating improvements entails a high degree of uncertainty. There can be no assurance that we will be able to identify and implement successful restructuring programs and improvements with respect to any distressed loans or investments we may have from time to time.

These financial or operating difficulties may never be overcome and may cause borrower entities to become subject to bankruptcy or other similar administrative proceedings. There is a possibility that we may incur substantial or total losses on our investments and in certain circumstances, become subject to certain additional potential liabilities that may exceed the value of our original investment therein. For example, under certain circumstances, a lender that has inappropriately exercised control over the management and policies of a debtor may have its claims subordinated or disallowed or may be found liable for damages suffered by parties as a result of such actions. In any reorganization or liquidation proceeding relating to our investments, we may lose our entire investment, may be required to accept cash or securities with a value less than our original investment and/or may be required to accept different terms, including payment over an extended period of time. In addition, under certain circumstances, payments to us may be reclaimed if any such payment or distribution is later determined to have been a fraudulent conveyance, preferential payment, or similar transaction under applicable bankruptcy and insolvency laws. Furthermore, bankruptcy laws and similar laws applicable to administrative proceedings may delay our ability to realize value from collateral for loan positions held by us, may adversely affect the economic terms and priority of such loans through doctrines such as equitable subordination or may result in a restructuring of the debt through principles such as the “cramdown” provisions of the bankruptcy laws.

Loans on properties in transition, including renovation and rehabilitation projects, involve greater risks of loss than conventional mortgage loans.

We may invest in transitional loans to borrowers seeking short-term capital for acquisition or rehabilitation of a property. The typical borrower has usually identified an undervalued asset that has been under-managed or is located in a recovering market. If the market fails to improve according to projections, or if the borrower fails to improve the asset’s management or value, the borrower may not receive a sufficient return to satisfy the loan, and we bear the risk of not recovering some or all of our investment.

Borrowers usually use conventional mortgage proceeds to repay transitional loans, subjecting us to the risk of a borrower’s inability to obtain permanent financing. Renovation and rehabilitation projects also involve risks of cost overruns and noncompletion, and estimates of improvement costs may prove inaccurate. If renovation is not completed timely or costs more than expected, the borrower may experience prolonged reduction of net operating income and may not be able to make payments on our investment. In addition, since such loans generally entail greater risk than loans collateralized by income-producing property, we may need to increase our allowance for loan losses. If a borrower fails to complete the project or experiences cost overruns, there could be adverse consequences including a decline in collateral value, borrower claims against us, increased costs the borrower cannot pay, bankruptcy, or abandonment of the collateral.

Our success depends on the availability of attractive investments and our ability to identify, structure, consummate, leverage, manage and realize returns on our debt investments.

Our operating results are dependent upon the availability of attractive investments and our ability to identify, structure, consummate, manage and realize returns on our debt investments. In general, the availability of favorable investment opportunities and, consequently, our returns, will be affected by the level and volatility of interest rates and credit spreads, conditions in the financial markets, general economic conditions, the demand for investment opportunities in our target assets and the supply of capital for such investment opportunities. We cannot assure you that we will be successful in identifying and consummating investments that satisfy our rate of return objectives or that such investments, once made, will perform as anticipated.

Real estate valuation is inherently subjective and uncertain.

The valuation of real estate and therefore the valuation of any collateral underlying our loans is inherently subjective due to, among other factors, the individual nature of each property, its location, the expected future rental revenues from that particular property and the valuation methodology adopted. In addition, where we invest in loans for renovation or rehabilitation projects, initial valuations will assume completion of the project. As a result, the valuations of the real estate assets against which we will make or acquire loans are subject to a large degree of uncertainty and are made on the basis of assumptions and methodologies that may not prove to be accurate, particularly in periods of volatility, low transaction flow or restricted debt availability in the commercial or residential real estate markets. This is true regardless of whether we internally perform such valuation or hire a third party to do so.

Our loans and investments may be concentrated in terms of geography, asset types, and sponsors.

We are not required to observe specific diversification criteria. Therefore, our investments may be concentrated in certain property types that may be subject to higher risk of default or foreclosure or secured by properties concentrated in a limited number of geographic locations.

To the extent that our assets are concentrated in any one region or type of asset, downturns generally relating to such type of asset or region may result in defaults on a number of our investments within a short time period, which could adversely affect our results of operations and financial condition. In addition, because of asset concentrations, even modest changes in the value of the underlying real estate assets could have a significant impact on the value of our investment. As a result of any high levels of concentration, any adverse economic, political or other conditions that disproportionately affects those geographic areas or asset classes could have a magnified adverse effect on our results of operations and financial condition, and the value of our bondholders’ investments could vary more widely than if we invested in a more diverse portfolio of loans.

The due diligence process that we undertake in regard to investment opportunities may not reveal all facts that may be relevant in connection with an investment and if we incorrectly evaluate the risks of our investments we may experience losses.

Before making investments, we conduct due diligence that we deem reasonable and appropriate based on the facts and circumstances relevant to each potential investment. When conducting due diligence, we may be required to evaluate important and complex business, financial, tax, accounting, environmental and legal issues. Outside consultants, legal advisors, accountants and investment banks may be involved in the due diligence process in varying degrees depending on the type of potential investment. Our loss estimates may not prove accurate, as actual results may vary from estimates. If we underestimate the asset-level losses relative to the price we pay for a particular investment, we may experience losses with respect to such investment.

Moreover, our investment analyses and decisions may frequently be required to be undertaken on an expedited basis to take advantage of investment opportunities. In such cases, the information available to us at the time of making an investment decision may be limited, and they may not have access to detailed information regarding such investment. Therefore, we cannot assure you that we will have knowledge of all circumstances that may adversely affect such investment.

We may be subject to risks associated with artificial intelligence and machine learning technology.

The Company uses a proprietary technology platform to facilitate the capture, monitoring, and reporting of loan portfolio data. Although this platform was developed with the assistance of artificial intelligence tools, it has little reliance on AI for its day-to-day functionality. Nonetheless, we may be exposed to risks if evolving AI regulations impose compliance obligations on us or if third-party service providers use AI in ways that create data privacy, data protection, or intellectual property concerns.

Insurance on loans and real estate securities collateral may not cover all losses.

There are certain types of losses, generally of a catastrophic nature, such as earthquakes, floods, hurricanes, terrorism or acts of war, which may be uninsurable or not economically insurable. Inflation, changes in building codes and ordinances, environmental considerations and other factors also might result in insurance proceeds insufficient to repair or replace a property if it is damaged or destroyed. Under these circumstances, the insurance proceeds received with respect to a property relating to one of our investments might not be adequate to restore our economic position with respect to our investment. Any uninsured loss could result in the corresponding nonperformance of or loss on our investment related to such property.

The impact of any future terrorist attacks and the availability of affordable terrorism insurance expose us to certain risks.

Terrorist attacks, the anticipation of any such attacks, and the consequences of any military or other response by the U.S. and its allies may have an adverse impact on the U.S. financial markets and the economy in general. We cannot predict the severity of the effect that any such future events would have on the U.S. financial markets, the economy or our business. Any future terrorist attacks could adversely affect the credit quality of some of our loans and investments. Some of our loans and investments will be more susceptible to such adverse effects than others, particularly those secured by properties in major cities or properties that are prominent landmarks or public attractions. We may suffer losses as a result of the adverse impact of any future terrorist attacks and these losses may adversely impact our results of operations.

In addition, the enactment of the Terrorism Risk Insurance Act of 2002, or TRIA, and the subsequent enactment of the Terrorism Risk Insurance Program Reauthorization Act of 2015 and the Terrorism Risk Insurance Program Reauthorization Act of 2019, which the latter extended TRIA through the end of 2027, requires insurers to make terrorism insurance available under their property and casualty insurance policies and provides federal compensation to insurers for insured losses. However, this legislation does not regulate the pricing of such insurance, and there is no assurance that this legislation will be extended after its expiration. The absence of affordable insurance coverage may adversely affect the general real estate lending market, lending volume and the market’s overall liquidity and may reduce the number of suitable investment opportunities available to us and the pace at which we are able to make investments. If the properties that we invest in are unable to obtain affordable insurance coverage, the value of those investments could decline and in the event of an uninsured loss, we could lose all or a portion of our investment.

We may need to foreclose on certain of the loans we originate or acquire, which could result in losses, subject us to the risks of owning real estate, or otherwise harm our results of operations and financial condition.

We may find it necessary or desirable to foreclose on certain of the loans we originate or acquire, and the foreclosure process may be lengthy and expensive. Borrowers may resist foreclosure actions by asserting claims, counterclaims, and defenses to prolong the action or force a loan modification. In some states, foreclosure actions can take several years to litigate. At any time during foreclosure proceedings, the borrower may file for bankruptcy, which would stay the foreclosure action and could result in reduction or discharge of the borrower’s debt. Foreclosure may also create a negative public perception of the property, resulting in a diminution of its value.

If we foreclose on an asset, we may take title to the property securing that asset and own and operate it as “real estate owned.” Owning and operating real property involves risks different from and more significant than owning an asset secured by that property, including: fluctuations in vacancy rates, rent schedules, and operating expenses; tenant bankruptcies; changes in local economic conditions; competition from similar properties; changes in interest rates and real estate tax rates; environmental legislation and zoning laws; and acts of God, terrorism, and civil disturbances. We may end up owning property we would not otherwise have acquired, and liquidation proceeds upon sale may not be sufficient to recover our cost basis in the loan, resulting in a loss.

The properties underlying our investments may be subject to unknown liabilities, including environmental liabilities, which could affect the value of these properties and as a result, our investments.

Collateral properties underlying our investments may be subject to unknown or unquantifiable liabilities that may adversely affect the value of our investments. Such defects or deficiencies may include title defects, title disputes, liens, servitudes or other encumbrances on the mortgaged properties. The discovery of such unknown defects, deficiencies and liabilities could affect the ability of our borrowers to make payments to us or could affect our ability to foreclose and sell the underlying properties, which could adversely affect our results of operations and financial condition.

Furthermore, to the extent we foreclose on properties securing loans we have made, we may be subject to environmental liabilities arising from such foreclosed properties. Under various U.S. federal, state and local laws, an owner or operator of real property may become liable for the costs of removal of certain hazardous substances released on its property. These laws often impose liability without regard to whether the owner or operator knew of, or was responsible for, the release of such hazardous substances.

If we foreclose on any properties underlying our investments, the presence of hazardous substances on a property may adversely affect our ability to sell the property and we may incur substantial remediation costs, therefore the discovery of material environmental liabilities attached to such properties could adversely affect our results of operations and financial condition.

We may be subject to lender liability claims, and if we are held liable under such claims, we could be subject to losses.

In recent years, a number of judicial decisions have upheld the right of borrowers to sue lending institutions on the basis of various evolving legal theories, collectively termed “lender liability.” Generally, lender liability is based upon the premise that a lender has either violated a duty, whether implied or contractual, of good faith and fair dealing owed to the borrower or has assumed a degree of control over the borrower resulting in the creation of a fiduciary duty owed to the borrower or its other creditors or stockholders. We cannot assure prospective investors that such claims will not arise or that we will not be subject to significant liability if a claim of this type did arise.

Any credit ratings assigned to our investments will be subject to ongoing evaluations and revisions and we cannot assure you that those ratings will not be downgraded.

Some of our investments issued in our securitization transactions for which we are required to retain a portion of the credit risk may be rated by rating agencies. Any credit ratings on our investments are subject to ongoing evaluation by credit rating agencies, and we cannot assure you that any such ratings will not be changed or withdrawn by a rating agency in the future if, in its judgment, circumstances warrant. If rating agencies assign a lower-than-expected rating or reduce or withdraw, or indicate that they may reduce or withdraw, their ratings of our investments in the future, the value and liquidity of our investments could significantly decline, which would adversely affect the value of our investment portfolio and could result in losses upon disposition or the failure of borrowers to satisfy their debt service obligations to us.

Investments in non-conforming and non-investment grade rated loans or securities involve increased risk of loss.

Many of our investments may not conform to conventional loan standards applied by traditional lenders and either will not be rated (as is typically the case for private loans) or will be rated as non-investment grade by the rating agencies. Private loans often are not rated by credit rating agencies. Non-investment grade ratings typically result from the overall leverage of the loans, the lack of a strong operating history for the properties underlying the loans, the borrowers’ credit history, the underlying properties’ cash flow or other factors. As a result, these investments should be expected to have a higher risk of default and loss than investment-grade rated assets. Any loss we incur may be significant and may adversely affect our results of operations and financial condition. There are no limits on the percentage of unrated or non-investment grade rated assets we may hold in our investment portfolio.

We must manage our portfolio so that we do not become an investment company that is subject to regulation under the Investment Company Act.

We conduct our operations so that we avail ourselves of the statutory exclusion provided in Section 3(c)(5)(C) for companies engaged primarily in investment in mortgages and other liens on or interests in real estate. In order to qualify for this exclusion, we must maintain, on the basis of positions taken by the SEC’s Division of Investment Management, or the “Division,” in interpretive and no-action letters, a minimum of 55% of the value of our total assets in mortgage loans and other related assets that are considered “mortgages and other liens on and interests in real estate,” which we refer to as “Qualifying Interests,” and a minimum of 80% in Qualifying Interests and real estate-related assets. In the absence of SEC or Division guidance that supports the treatment of other investments as Qualifying Interests, we will treat those other investments appropriately as real estate-related assets or miscellaneous assets depending on the circumstances.

Because registration as an investment company would significantly affect our ability to engage in certain transactions or be structured in the manner we currently are, we intend to conduct our business so that we will continue to satisfy the requirements to avoid regulation as an investment company. If we do not meet these requirements, we could be forced to alter our investment portfolio by selling or otherwise disposing of a substantial portion of the assets that do not satisfy the applicable requirements or by acquiring a significant position in assets that are Qualifying Interests. Any such investments may not represent an optimum use of capital when compared to the available investments we and our subsidiaries target pursuant to our investment strategy and present additional risks to us. We continue to analyze our investments and may make certain investments when and if required for compliance purposes. Altering our portfolio in this manner may have an adverse effect on our investments if we are forced to dispose of or acquired assets in an unfavorable market.

If it were established that we were an unregistered investment company, there would be a risk that we would be subject to monetary penalties and injunctive relief in an action brought by the SEC, that we would be unable to enforce contracts with third parties, that third parties could seek to obtain rescission of transactions undertaken during the period it was established that we were an unregistered investment company. In order to comply with provisions that allow us to avoid the consequences of registration under the Investment Company Act, we may need to forego otherwise attractive opportunities and limit the manner in which we conduct our operations. Therefore, compliance with the requirements of the Investment Company Act may hinder our ability to operate solely on the basis of maximizing profits.

DILUTION

Dilution means a reduction in value, control, or earnings of the shares the investor owns.

Immediate Dilution

Developing companies typically sell shares (or grants options over its shares) to its founders and early-stage employees at a low cash cost because they are, in effect, putting their “sweat equity” into the company. When we seek cash investments from outside investors, like you, new investors typically pay a larger amount for their shares than the founders or earlier investors, which means that the cash value of your stake is diluted because all the shares are worth the same amount, and you paid more than earlier investors for your shares. No shares in the Predecessor have been acquired during the past year by any of officers, directors, promoters or affiliated persons.

The table set forth below illustrates the dilution that new investors will experience upon an investment in the Company relative to existing holders of our securities. In the table, we present four scenarios for the convenience of the reader: a fully subscribed $25,000,000 raise from this Offering, an $18,750,000 raise from this Offering, a $12,500,000 raise from this Offering, and a $6,250,000 raise from this Offering.

In the table, we did not calculate dilution based on the net book value (member’s deficit) of Predecessor of $(116,269,326) as of December 31, 2025 as set forth on page F-2 of Predecessor’s audited financial statements, instead using an adjusted net book value (member’s deficit) of Predecessor of $(15,484,304) as of December 31, 2025, as presented in the Supplementary Information found on page F-36 of Predecessor’s financial statements. We did not use former amount because it includes in the deficit amounts attributable to our subsidiary and other affiliated companies for obligations for which Predecessor (and now, Company) has no liability. The holders of these obligations do not have recourse to the general credit of Predecessor (and now, the Company), but they are nevertheless required to be consolidated in our financial statements.

Because the supplemental adjusted measure of book value (members’ equity) is considered a non-GAAP financial measure, we have prepared the following reconciliation showing how that number is derived, as of December 25, 2025, from the GAAP number:

We believe that this presentation is  meaningful to investors because it reflects the legal reality of the Company and its subsidiaries and reflects management’s view of the operation and the metrics that they use to make internal strategic decisions.

Future Dilution

Another important way of looking at dilution is the dilution that happens due to future actions we may take. If we issue additional shares, your stake could be diluted. In other words, when we issue more shares, the percentage of the Company that you own will go down, even though the value of the Company may go up. You will own a smaller piece of a larger company. This increase in number of shares outstanding could result from a stock offering (such as an initial public offering, another crowdfunding round, a venture capital round, or an angel investment), employees exercising stock options, or by conversion of certain instruments (e.g., convertible bonds, preferred shares or warrants) into common stock.

If we decide to issue more shares, an investor could experience value dilution, with each share being worth less than before, and control dilution, with the total percentage an investor owns being less than before. There may also be earnings dilution, with a reduction in the amount earned per share (though this typically occurs only if we offer dividends, and most early-stage companies are unlikely to offer dividends, preferring to invest any earnings into the company).

The type of dilution that hurts early-stage investors most often occurs when the company sells more shares in a “down round,” meaning at a lower valuation than in earlier offerings. An example of how this might occur is as follows (numbers are for illustrative purposes only):

This type of dilution might also happen upon conversion of convertible securities into shares. Typically, the terms of convertible securities issued by early-stage companies provide that in the event of another round of financing, the holders of the convertible securities get to convert their securities into equity at a “discount” to the price paid by the new investors, i.e., they get more shares than the new investors would for the same price. Additionally, convertible securities may have a “price cap” on the conversion price, which effectively acts as a share price ceiling. Either way, the holders of the convertible securities get more shares for their money than new investors. If the financing is a “down round” the holders of the convertible securities will dilute existing equity holders, and even more than the new investors do, because they get more shares for their money. Investors should pay careful attention to the amount of convertible securities that we have issued (or have authorized and may issue in the future), and the terms of those securities.

If you are making an investment expecting to own a certain percentage of the Company or expecting each share to hold a certain amount of value, it is important to realize how the value of those shares can decrease by actions we take. Dilution can cause drastic changes to the value of each share, ownership percentage, voting control, and earnings per share.

PLAN OF DISTRIBUTION

The Company is offering up to 2,500,000 shares of Series R Preferred Stock on a “best efforts” basis at a price of $10.00 per Share. The maximum offering amount may be increased up to 3,500,000 shares ($35,000,000) of Series R Preferred Stock in the sole discretion of the Company. There is no minimum number of shares of Series R Preferred Stock that we must sell in order to conduct a closing in this Offering.

The Company intends to market the Series R Preferred Stock in this Offering using both online and offline means. Online marketing may take the form of contacting potential investors through electronic media, electronic advertising and posting our Offering Circular on an online investment platform. All advertising will direct investors to the online investment platform. This Offering Circular will be furnished to prospective investors via download from the Company’s website (www.invest.oakrealestate.com ) on a landing page that relates to the Offering.

The Offering will terminate at the earliest of the date at which the maximum offering amount has been sold, one year from the date upon which the SEC qualifies the Offering Statement of which this Offering Circular forms a part or the date at which the Offering is earlier terminated by the Company, in its sole discretion.

We intend to complete multiple closings for this Offering on a rolling basis until the maximum offering amount is raised or this Offering is terminated. Until we complete a closing, the amounts invested by investors in this Offering will be kept in an escrow account maintained at Wilmington Trust, National Association. 

Engagement Agreement with Digital Offering

We are currently party to an engagement agreement dated March 9, 2026, with Digital Offering. Digital Offering has agreed to act as our lead managing selling agent for the Offering. Digital Offering has made no commitment to purchase all or any part of the Series R Preferred Stock but has agreed to use its best efforts to sell such Series R Preferred Stock in the Offering. As such, Digital Offering is an “underwriter” within the meaning of Section 2(a)(11) of the Securities Act of 1933, as amended (the “Securities Act”). Digital Offering is under no obligation to purchase any of the Series R Preferred Stock or arrange for the sale of any specific number or dollar amount of Series R Preferred Stock. The term of the engagement agreement will continue until the earliest to occur of: (a) the date that either party gives the other at least ten (10) days written notice of the termination of the engagement agreement, which termination may occur with or without cause, (b) June 30, 2027, and (c) the date that the Offering is consummated (such applicable date, the “Termination Date”). The engagement agreement provides that Digital Offering may engage other Financial Industry Regulatory Authority (“FINRA”) member broker-dealers that are registered with the SEC to participate as soliciting dealers for this Offering. We refer to these other broker-dealers as soliciting dealers or members of the selling group. Upon engagement of any such soliciting dealer, Digital Offering will be permitted to re-allow all or part of its fees and expense allowance as described below. Such soliciting dealer will also be entitled to receive the benefits of our engagement agreement with Digital Offering, including the indemnification rights arising under the engagement agreement upon their execution of a soliciting dealer agreement with Digital Offering that confirms that such soliciting dealer is so entitled. As of the date hereof, we have been advised that Digital Offering has retained Crescent Securities, Inc. to participate in this Offering as a soliciting dealer. We will not be responsible for paying any placement agency fees, commissions or expense reimbursements to any soliciting dealers retained by Digital Offering. None of the soliciting dealers is purchasing any of the Series R Preferred Stock in this Offering or is required to sell any specific number or dollar amount of Series R Preferred Stock but will instead arrange for the sale of Series R Preferred Stock to investors on a “best efforts” basis, meaning that they need only use their best efforts to sell the Series R Preferred Stock. In addition to the engagement agreement, we plan to enter into a definitive selling agency agreement with Digital Offering prior to the commencement of the Offering.

Offering Expenses

We are responsible for all Offering fees and expenses, including the following: (i) fees and disbursements of our legal counsel, accountants, and other professionals we engage; (ii) fees and expenses incurred in the production of Offering documents, including design, printing, photograph, and written material procurement costs; (iii) all filing fees, including those charged by FINRA; (iv) all of the legal fees related to FINRA clearance; and (v) costs relating to background checks of the Company’s officers and directors (in the specific invoiced amount of $760, which amount has already been paid by us and will not be exceeded) and $25,000 in accountable due diligence expenses of Digital Offering. This $25,000 has already been paid to Digital Offering by us and will be reimbursed to us to the extent not actually incurred, in compliance with FINRA Rule 5110(g)(4)(a). We have also agreed to reimburse Digital Offering for up to $100,000 in legal expenses, $25,000 of which we have already paid. The $25,000 payment for legal fees already made will be reimbursed to us to the extent not actually incurred, in compliance with FINRA Rule 5110(g)(4)(a).

Reimbursable Expenses in the Event of Termination

In the event the Offering does not close, or the selling agency agreement is terminated for any reason, we have agreed to reimburse Digital Offering for its legal fees not to exceed $100,000.

Other Expenses of the Offering

The Company has engaged EquiDeFi Ltd. (“EquiDeFi”) to create and maintain the online subscription processing platform for the Offering. After the Company’s Offering Statement of which this Offering Circular is a part is qualified by the SEC, the Offering will be conducted, in part, using EquiDeFi’s online subscription processing platform through the Company’s website at www.invest.oakrealestate.com, whereby investors will receive, review, execute and deliver subscription agreements electronically as well as make purchase price payments through a third-party processor by ACH debit transfer, wire transfer or credit card to an account we designate. We will hold closings upon the receipt of investors’ subscriptions and our acceptance of such subscriptions.

The Company will pay EquiDeFi an advance of $7,500. Starting once the offering is open to accepting investors, the Company will also pay EquiDeFi $6,000 monthly in account maintenance fees (up to a maximum of $31,000 during the duration of the offering). In addition, the Company will pay EquiDeFi credit card processing fees (3.9% + $0.30 per swipe) plus any charge back fees or expenses and 1.00% + $5.00 for each ACH transfer fee to all purchasers in lieu of charges to investors and a KYC/AML verification fee of $30.00 for each investor.

Please be advised that different payment methods take different amounts of time to clear.

The Company maintains the right to accept or reject subscriptions in whole or in part, for any reason or for no reason, including, but not limited to, in the event that an investor fails to provide all necessary information, even after further requests, in the event an investor fails to provide requested follow up information to complete potential background checks or fails background checks, and in the event the Offering is oversubscribed in excess of the maximum offering amount. If a subscription is rejected, funds will not be accepted by wire transfer or ACH, and payments made by debit card or check will be returned to subscribers within 30 days of such rejection without deduction or interest.

Selling Agents’ Commission

We have agreed that the definitive selling agency agreement will provide for us to pay a cash commission of 7.5% of the gross proceeds received by us in the Offering, which shall be allocated by Digital Offering to members of the selling group and soliciting dealers in its sole discretion (we sometimes refer to Digital Offering and such members and dealers collectively as the “Selling Agents”).

The following table shows the total commissions payable to Digital Offering on a per-share basis in connection with this Offering, assuming a fully subscribed offering.

Selling Agent’s Warrant

Upon each closing of the Offering, we have agreed to issue an Agent Warrant to the Selling Agents to purchase a number of shares of Series R Preferred Stock equal to 3% of the total number of shares of Series R Preferred Stock sold in that closing of the Offering. The Agent Warrant will be immediately exercisable upon issuance and will be exercisable until the fifth anniversary of the date of commencement of sales in the Offering (in compliance with FINRA Rule 5110(e)(1)). The exercise price for the Agent Warrant will be the amount that is 25% greater than the public offering price, or $10.00 per share. The Agent Warrant will not be redeemable. The Agent Warrant will provide for cashless exercise in the event there is not a qualified offering statement covering the shares underlying the Agent Warrant, and immediate “piggyback” registration rights, with a duration of seven years from the date of commencement of sales in the Offering (in compliance with FINRA Rule 5110(g)(8)(D)), with respect to the registration of the shares underlying the warrants. We have qualified the shares underlying the Agent Warrant in this Offering. Under certain circumstances, we may enter into an agreement with the Selling Agents to provide the Selling Agents with a demand registration right. Pursuant to FINRA Rule 5110(g)(8)(B)-(D), under any such agreement, the Selling Agents shall not be entitled to more than one demand registration right and the duration of this registration right shall not exceed five years from the effective date of the related registration statement.

The Agent Warrant and the shares underlying the Agent Warrant have been deemed compensation by FINRA and are therefore subject to a 180-day lock-up pursuant to Rule 5110(e)(1) of FINRA. The Selling Agents or permitted assignees under such rule, may not exercise, sell, transfer, assign, pledge, or hypothecate the Agent Warrant or the shares underlying the Agent Warrant, nor will the Selling Agents or permitted assignees engage in any hedging, short sale, derivative, put, or call transaction that would result in the effective economic disposition of the Agent Warrant or the underlying shares for a period of 180 days from the date of commencement of sales in the Offering, except that they may be transferred, in whole or in part, by operation of law or by reason of our reorganization, or to any Selling Agent or selected dealer participating in the Offering and their officers, partners or registered representatives if the Agent Warrant or the underlying shares so transferred remain subject to the foregoing lock-up restrictions for the remainder of the time period. The Agent Warrant will provide for adjustment in the number and price of such warrants (and the shares underlying such Agent Warrant) to prevent dilution in the event of a stock dividend, stock split or other reclassification of such underlying shares.

Indemnification

We have agreed to indemnify the Selling Agent, its affiliates and controlling persons and members of the selling group against certain liabilities, including liabilities under the Securities Act. If we are unable to provide this indemnification, we will contribute to the payments the Selling Agent, its affiliates and controlling persons as may be required to make in respect of these liabilities.

Our Relationship with the Lead Selling Agent

The Selling Agent and its affiliates are engaged in various activities, which may include securities trading, commercial and investment banking, financial advisory, investment management, investment research, principal investment, hedging, financing and brokerage activities. The Selling Agent and its affiliates may in the future perform various financial advisory and investment banking services for us, for which they received or will receive customary fees and expenses.

In the ordinary course of their various business activities, Digital Offering and its affiliates may make or hold a broad array of investments and actively trade debt and equity securities (or related derivative securities) and financial instruments (including bank loans) for their own account and for the accounts of their customers, and such investment and securities activities may involve securities and/or instruments of the Company. Digital Offering and its affiliates may also make investment recommendations and/or publish or express independent research views in respect of such securities or instruments, or recommend to clients that they acquire, long and/or short positions in such securities and instruments. 

Investment Limitations

As set forth in Title IV of the JOBS Act, for individuals who are not accredited investors, no sale may be made to you in this Offering if the aggregate purchase price you pay is more than 10% of the greater of your annual income or net worth (please see below under “How to Calculate Net Worth”). Different rules apply to accredited investors and non-natural persons. Before making any representation that your investment does not exceed applicable thresholds, we encourage you to review Rule 251(d)(2)(i)(C) of Regulation A. For general information on investing, we encourage you to refer to www.investor.gov.

Because this is a Tier 2, Regulation A offering, most investors in the case of trading on the over-the-counter markets must comply with the 10% limitation on investment in this Offering. The only investors in this Offering exempt from this limitation are “accredited investors” as defined under Rule 501 of Regulation D under the Securities Act (each, an “Accredited Investor”). If you meet one of the following tests you should qualify as an Accredited Investor:

(i) You are a natural person who has had individual income in excess of $200,000 in each of the two most recent years, or joint income with your spouse or spousal equivalent in excess of $300,000 in each of these years, and have a reasonable expectation of reaching the same income level in the current year;

(ii) You are a natural person and your individual net worth, or joint net worth with your spouse or spousal equivalent, exceeds $1,000,000 at the time you purchase Series R Preferred Stock (please see below under “How to Calculate Net Worth”);

(iii) You are an executive officer or general partner of the issuer or a director, executive officer or general partner of the general partner of the issuer;

(iv) You are a holder in good standing of the General Securities Representative license (Series 7), the Private Securities Offerings Representative license (Series 82), and the Licensed Investment Adviser Representative (Series 65), each as issued by FINRA;

(v) You are a corporation, limited liability company, partnership or are an organization described in Section 501(c)(3) of the Internal Revenue Code of 1986, as amended, a corporation or similar business trust or a partnership, not formed for the specific purpose of acquiring the Series R Preferred Stock, with total assets in excess of $5,000,000;

(vi) You are a bank or a savings and loan association or other institution as defined in the Securities Act, a broker or dealer registered pursuant to Section 15 of the Exchange Act, an insurance company as defined by the Securities Act, an investment company registered under the Investment Company Act of 1940 (the “Investment Company Act”), or a business development company as defined in that act, any Small Business Investment Company licensed by the Small Business Investment Act of 1958 or a private business development company as defined in the Investment Advisers Act of 1940;

(vii) You are an entity (including an Individual Retirement Account trust) in which each equity owner is an accredited investor;

(viii) You are a trust with total assets in excess of $5,000,000, your purchase of Series R Preferred Stock is directed by a person who either alone or with his purchaser representative(s) (as defined in Regulation D promulgated under the Securities Act) has such knowledge and experience in financial and business matters that he is capable of evaluating the merits and risks of the prospective investment, and you were not formed for the specific purpose of investing in the Series R Preferred Stock;

(ix) You are a plan established and maintained by a state, its political subdivisions, or any agency or instrumentality of a state or its political subdivisions, for the benefit of its employees, if such plan has assets in excess of $5,000,000;

(x) You are a Commission or state-registered investment adviser or a federally exempt reporting adviser;

(xi) You are a Rural Business Investment Company as defined in section 384A of the Consolidated Farm and Rural Development Act;

(xii) You are an entity not listed above that that owns “investments,” in excess of $5 million and that was not formed for the specific purpose of investing in the securities offered; or

(xiii) You are an Investor that certifies that (A) it is a “family office” as defined in Rule 202(a)(11)(G)-1 under the Investment Advisers Act of 1940 (i) with at least $5 million in assets under management, (ii) not formed for the specific purpose of acquiring the securities offered and (iii) whose investment is directed by a person who has such knowledge and experience in financial and business matters that such family office is capable of evaluating the merits and risks of the prospective investment or (B) that it is a “family client” as defined in Rule 202(a)(11)(G)-1, of a family office meeting the criteria specified above.

For the purposes of the foregoing, “spousal equivalent” is defined as a cohabitant occupying a relationship generally equivalent to that of a spouse.

This Offering will start on or after the date that the Offering is qualified by the SEC and will terminate on the earliest of the date at which the maximum offering amount has been sold, one year from the date upon which the SEC qualifies the Offering Statement of which this Offering Circular forms a part and the date at which the Offering is earlier terminated by the Company, in its sole discretion.

Procedures for Subscribing

Investors may subscribe through www.invest.oakrealestate.com by tendering funds by wire, credit, or debit card or ACH transfer to the escrow account to be set up Wilmington Trust, National Association, the escrow agent. Tendered funds will remain in escrow until the closing has occurred. Upon the closing, funds tendered by investors will be made available to us for our use. We will not cover credit card fees on behalf of investors.

Procedures for subscribing directly through the Company’s website

The subscription procedure is summarized as follows:

Escrow Account

Investors will be required to deposit their funds to the Wilmington Trust Escrow Account. The Company intends to complete multiple closings of this Offering on a rolling basis. Any such funds that the Company receives shall be held in escrow until the closing of the Offering or such other time as mutually agreed between the Company and Digital Offering, and then used to complete securities purchases, or returned if this Offering fails to close. All subscribers will be instructed by the Company or its agents to transfer funds by wire or ACH transfer directly to the Wilmington Trust Escrow Account established for this Offering.

Right to Reject Subscriptions

After we receive your complete, executed subscription agreement (forms of which are attached to the Offering Statement, of which this Offering Circular forms a part, as Exhibits 4.1 and 4.2) and the funds required under the subscription agreement have been transferred to the Wilmington Trust Escrow Account, we have the right to review and accept or reject your subscription in whole or in part, for any reason or for no reason. We will return all monies from rejected subscriptions immediately to you, without interest or deduction.

Acceptance of Subscriptions

Upon our acceptance of a subscription agreement, we will countersign the subscription agreement and issue the Series R Preferred Stock at a closing. Once you submit the subscription agreement and it is accepted, you may not revoke or change your subscription or request your subscription funds. All accepted subscription agreements are irrevocable.

Under Rule 251 of Regulation A, unless a company’s offered securities are listed on a national securities exchange, non-accredited, non-natural person investors are subject to the investment limitation and may only invest funds which do not exceed 10% of the greater of the purchaser’s revenue or net assets (as of the purchaser’s most recent fiscal year end). As a result, non-accredited, natural person may only invest funds in our Series R Preferred Stock which do not exceed 10% of the greater of the purchaser’s annual income or net worth (please see below on how to calculate your net worth).

How to Calculate Net Worth

For the purposes of calculating your net worth, it is defined as the difference between total assets and total liabilities. This calculation must exclude the value of your primary residence and may exclude any indebtedness secured by your primary residence (up to an amount equal to the value of your primary residence). In the case of fiduciary accounts, net worth and/or income suitability requirements may be satisfied by the beneficiary of the account or by the fiduciary, if the fiduciary directly or indirectly provides funds for the purchase of the Series R Preferred Stock.

In order to purchase the Series R Preferred Stock and prior to the acceptance of any funds from an investor, an investor in our Series R Preferred Stock will be required to represent, to the Company’s satisfaction, that he or she is either an accredited investor or is in compliance with the 10% of net worth or annual income limitation on investment in this Offering.

No Minimum Offering Amount

There is no minimum offering amount in this Offering and we may close on any funds that we receive. Potential investors should be aware that there can be no assurance that any other funds will be invested in this Offering other than their own funds.

No Selling Security Holders

No securities are being sold for the account of security holders; all net proceeds of this Offering will go to the Company.

Transfer Agent and Registrar

The Company has engaged Equity Stock Transfer, LLC, a registered transfer agent with the SEC, who will serve as transfer agent to maintain stockholder information on a book-entry basis.

USE OF PROCEEDS TO ISSUER

We are offering up to 2,500,000 shares of our Series R Preferred Stock in this Offering.

The table below provides a summary of our estimated net proceeds, depending upon the ultimate size of this Offering:

The Company anticipates that approximately 90% of the offering proceeds will be available to retire bonds issued by the Sponsored Funds, as well as to fund business operations and working capital of the Company generally.

The following table sets forth the estimated sources and uses of proceeds of this offering of Series R Preferred Stock assuming that we sell the maximum offering amount of $25,000,000 in Series R Preferred Stock and that the Board does not expand the maximum offering amount to $35,000,000. There is also no minimum offering amount to break escrow, meaning we can accept subscriptions immediately. Many of the figures set forth below represent our best estimate since they cannot be precisely calculated at this time.

Although a substantial portion of the amount available for investment presented in this table is expected to be used to retire bonds issued by ROCF IV Series and other select bond obligations of the Sponsored Funds, we may use a portion of such amount for other corporate purposes, including, but not limited to, payment of distributions to stockholders, or payments of organization and offering expenses in connection with future offerings pending the receipt of offering proceeds from such offerings. We may use an unlimited amount of proceeds for other corporate purposes, including to fund distributions. If we use any net offering proceeds for any purposes other than making investments in properties or reducing debt, it may negatively impact the value of your investment.

We reserve the right to change the above use of proceeds if management believes it is in our best interests.

BUSINESS

 Overview

The Company is a newly-formed Delaware corporation that was formed by Red Oak Capital Holdings, LLC (“ROCH” or the “Predecessor”) solely for the purpose of entering into a business combination with ROCH and its affiliated companies. The Company is the successor to ROCH, a Charlotte, North Carolina based commercial real estate finance company specializing in the acquisition, processing, underwriting, operational management and servicing of commercial real estate debt instruments. On or prior to the date that this Offering is qualified by the SEC, the Company will acquire the Predecessor by way of a merger, in which the Predecessor will merge with and into the Company, with the Company continuing as the surviving entity and succeeding to the business of the Predecessor (the “Reorganization”). The Company will continue the Predecessor’s business of sponsoring and managing a family of commercial real estate credit funds (the “Sponsored Funds”), originating senior secured, first-lien bridge loans. Through its affiliates, Red Oak Capital GP, LLC (“ROGP”) and Red Oak Financial, LLC (“Red Oak Financial”), the Company will earn offering-related fees, asset management fees, loan origination fees, loan servicing fees, loan disposition fees, and equity distributions from the Sponsored Funds and their lending activities.

Corporate Formation and Company Reorganization

On or prior to the date that this Offering is qualified, the Company will complete the Reorganization,. As a result, the equity holders of the Predecessor will receive either shares of voting Class A Common Stock or shares of non-voting Class B Common Stock of the Company in exchange for their membership interests depending on the class of membership interests held in the Predecessor, and the Company will succeed to the assets, liabilities, rights and obligations of the Predecessor. The Reorganization is intended to simplify the Company’s organizational structure and to provide a corporate form to better position the Company to access the capital markets and potentially become an exchange-listed public company.

In connection with the Reorganization, Red Oak Holdings Management, LLC (“ROHM”) also will be merged with and into the Company, and all investment management, origination, and operational functions previously handled by ROHM will be internalized within the Company. This internalization will eliminate certain external management fees, align management economics directly with stockholder outcomes, and further simplify the corporate and reporting structure of the Company.

Below is a summary of the steps involved in the reorganization:

Corporate Structure

Following the Reorganization, the Company will serve as the parent company of the various operating businesses that make up the Company’s operating platform. These include the Sponsored Funds, which will be the Company’s core commercial lending entities, though the Company intends to originate loans from its own balance sheet as well; ROGP, which serves as the managing member of the Sponsored Funds and receives offering-related fees, asset management fees, loan disposition fees, and distributions from the Sponsored Funds; and Red Oak Financial, which originates the commercial loans for the Sponsored Funds and receives loan origination fees and loan servicing fees in connection with loans made by the Sponsored Funds. Each of the entities in the Company’s platform is described in more detail below.

Sponsored Funds

The Sponsored Funds are commercial lending programs that originate senior loans collateralized by commercial real estate in the United States. The investment approach of the Sponsored Funds is to originate short-term, high-yielding senior loans collateralized by income producing commercial real estate assets to established and qualified real estate investors and operators at reasonable loan-to-value ratios which will be vetted through the Company’s underwriting process. The Sponsored Funds focus on transactions that meet the Company’s underwriting risk parameters, but do not meet the typical conforming standards of traditional banks and lenders. The Sponsored Funds follow specific lending guidelines including, but not limited to, senior lien position, concentration, asset classes, geography, natural disaster regions, zoning, borrower structure and guarantee, loan-to-value and loan-to-cost, term, fees and interest income and interest reserves.

The Sponsored Funds have conducted a series of securities offerings to fund their lending activities. As of the date of this Offering Circular, the Sponsored Funds have raised an aggregate of $352.6 million through their offerings and have deployed approximately $491.6 million in commercial real estate loans.

Through the Sponsored Funds, the Company may also acquire opportunistic properties and distressed loans from the Sponsored Funds, or other third-party sellers, upon which our management team expects to acquire the underlying real property via foreclosure or similar process.

As of the date of this Offering Circular, there are five Sponsored Funds: Red Oak Capital Fund III, LLC; Red Oak Capital Fund VI, LLC; Red Oak Capital Fund VII, LLC; Red Oak Income Opportunity Fund II, LLC; and Red Oak Capital Fund Series, LLC, each of which is described in more detail below:

Red Oak Capital GP, LLC

Red Oak Capital GP, LLC (“ROGP”) is our wholly owned subsidiary and serves as the managing member of the Sponsored Funds.

In connection with the Sponsored Funds, ROGP collects various fees from the Sponsored Funds that consist of offering-related fees, asset management fees, and loan disposition fees, although not all fee types are collected from each Sponsored Fund. In addition, ROGP is the sole equity holder in the Sponsored Funds capitalized by debt offerings, or “Debt Funds.” ROGP may receive distributions on its equity in the Sponsored Funds following the payment of required interest and principal payments to bondholders in the Debt Funds. As the sole equity holder, the activities of the Sponsored Funds are consolidated on our financial statements included herein.

In connection with each offering conducted by a Sponsored Fund, ROGP collects an organizational and offering fee equal to 2.0% of the gross offering proceeds from such offering, though the organizational and offering fee is reduced by the actual organization and offering costs for the offering incurred by such Sponsored Fund.

ROGP will also be paid certain fees by the Sponsored Funds related to their operating activities. While the fees paid by each Sponsored Fund vary, such fees are generally comprised of quarterly asset management fees, acquisition fees, and disposition fees. The quarterly asset management fees generally equal either (i) 1.00% per annum of (a) all capital invested by investors in a Sponsored Fund, net of any amounts invested at that time by the Sponsored Fund in loans or debt instruments, plus (b) the outstanding principal amount of each loan or real estate debt instrument then held by a Sponsored Fund, including loans secured by real estate then owned as a result of borrower default or (ii) 0.25% to 1.75% per annum of the gross principal outstanding of all bonds offered by a Sponsored Fund. Acquisition fees generally equal 0.50% of a Sponsored Fund’s gross mortgage loans receivable, inclusive of any closing costs. Disposition fees generally equal 0.50% to 1.00% of proceeds received from the repayment of the principal amount of debt investments to a Sponsored Fund or any other disposition of the underlying real estate by a Sponsored Fund. As noted above, not all Sponsored Funds pay the same types of fees, and even if two Sponsored Funds pay the same type of fee, the amount of such fee may vary.

Red Oak Financial, LLC

Red Oak Financial, LLC (“Red Oak Financial”) is our wholly owned subsidiary and originates the commercial real estate loans for the Sponsored Funds. Red Oak Financial operates within an extensive network of contacts with expansive market reach to source meaningful deal flow. Red Oak Financial will seek mortgage loan originator licenses in various states as required. Red Oak Financial will earn origination fees on the loans it sources. These origination fees are typically based on a percentage of the principal amount of the applicable loan, most commonly 1.0% or 2.0% of principal. Origination fees paid to Red Oak Financial are paid by the borrower of any loan originated by Red Oak Financial and not the Sponsored Fund making the loan. Red Oak Financial may also charge such borrowers asset management fees, servicing fees, special servicing fees, and merchant banking fees.

Loan Portfolio

As of December 31, 2025, through certain of the Sponsored Funds and direct holding company participations, the Company held 28 senior secured loans, providing $178.4 million of senior secured loans to various borrowers, which is gross of approximately $7.5 million of participation loans payable and excludes one related party loan between Red Oak Capital Fund III, LLC (borrower) and Red Oak Income Opportunity Fund II, LLC (lender) with principal of approximately $1.7 million. Such related party loan is included in the table below but eliminated upon consolidation, as further described in the footnotes to the table. The portfolio of loans possessed a weighted average interest rate of 11.24% and a weighted average additional paid-in-kind (“PIK”) interest rate of 0.65%. The portfolio loans have maturities ranging from June 2024 to November 2027. The following table outlines the major terms of each outstanding loan at December 31, 2025:

Competitive Strengths

The Company believes it will be well positioned in the commercial real estate lending and financial services market due to its competitive strengths and capabilities that differentiate it from other participants in the space. The Company is among a small number of sub-$20 million commercial real estate lenders that have built the infrastructure, regulatory understanding, and track record necessary to originate and service insurance-quality separately managed accounts (“SMA”) at scale. The loans originated by the Company will be structured to weather a range of economic scenarios by utilizing a combination of floating interest rates, short loan terms, senior secured first-lien positions, and conservative loan-to-value ratios. Further, the Company’s vertically integrated operating platform allows the Company to control each stage of the lifecycle of a loan from origination to disposition, eliminating third-party service provider risks and promoting efficiencies. The Company will generate revenue through six integrated and self-reinforcing business lines that span the full commercial real estate credit lifecycle. Each business line strengthens the others: origination produces loans that asset management and servicing preserve and monetize; the SMA platform amplifies origination volume beyond what the Company’s balance sheet can support; and special servicing experience improves underwriting discipline across every new loan. Further, to the extent the Company engages with and consummates a potential acquisition of its affiliate, White Oak Capital Holdings, LLC, and builds out its Federal Housing Administration (“FHA”) platform and, such platform will convert short-duration bridge relationships into long-duration, fee-generating financing partnerships. The result is a flywheel, not a pipeline—a platform whose competitive advantages compound with scale rather than erode under it.

A central element to the Company’s operations will be the use of a proprietary technology platform used to facilitate the capture, monitoring and reporting on the loan portfolio using a Straight-Through-Processing concept. This platform will utilize tools developed with the assistance of artificial intelligence (“AI”) to aid in the extraction of salient data received from potential borrowers, third-party service providers and external information vendors to present consistent, auditable information for each loan opportunity. Although the technology platform was developed with the assistance of AI, the technology platform will have little reliance on AI for its day-to-day functionality. The use of the platform will facilitate rapid pricing, credit and underwriting, loan servicing, and asset management, significantly shortening the business origination, loan execution, and loan servicing processes, with all output of the technology platform subject to a “Review and Challenge” concept where each transaction is reviewed and challenged by experienced underwriting staff. The technology platform will also enforce layered approvals and fund disbursement procedures to ensure each loan drawing obtains multiple levels of review and approval prior to the remittance of any funds to a borrower or project. The utilization of the platform will reduce the overall cost of procuring and monitoring a loan and reduce the potential for data entry errors, providing growth economies of scale.

By targeting the $2 million to $20 million commercial real estate (“CRE”) lending segment, the Company will be able to take advantage of a structurally underserved market, providing a deep, selective pipeline that supports consistent, high-quality loan production. These competitive strengths, coupled with the Company’s experienced leadership team, have provided the Company, as successor to the Predecessor, with a proven track record through multiple market cycles, originating approximately $560 million in cumulative commercial real estate loans since inception, including 33 full-cycle loans totaling approximately $200 million in aggregate principal.

Market Opportunity

The $2 million to $20 million commercial real estate lending market is structurally complicated. The loans provided are too small to be efficiently served by large-cap platforms, and the market is too complex to be profitably underwritten by community banks operating at scale and too lightly capitalized to attract the institutional origination infrastructure the segment requires. The result is a persistent yield premium. Where large-balance CRE loans clear at SOFR plus 375–525 basis points, the loan segment to be underwritten by the Company regularly clears at SOFR plus 450–750 basis points — a spread advantage of 100 to 300 basis points that institutional insurers and allocators are actively seeking and is available precisely because the market lacks the organized, creditworthy counterparties to supply it consistently. The Company has developed the origination infrastructure, underwriting systems, servicing capabilities, and institutional relationships required to operate as a first-tier lender in this segment at national scale and be the counterparty these investors require.

At the same time, the market environment in which the Company will operate is shaped by a convergence of structural and cyclical forces that the Company believes will sustain demand for its financial services and managed lending platform over the medium term, including the following:

Growth Strategy

General

The Company intends to continue to expand on its track record and successes by scaling its platform and capabilities by:

Proceeds of Offering

Historically, revenue received from the Sponsored Funds has consisted of loan origination fees, asset management fees, loan servicing fees, and disposition fees associated with deploying the capital raised in the Sponsored Funds’ offerings; however, the interest revenue received from the Sponsored Funds’ borrowers has historically been used to provide for the interest and maturity obligations associated with the Sponsored Funds’ bond offerings. By using proceeds from this Offering to pay down certain maturing bond obligations of the Sponsored Funds, the Company aims to capture the full cash spread between the all-in yield on such loans and the cost of equity capital raised in the Sponsored Funds’ offerings. The Company estimates this spread to be between 800 and 1000 basis points. The Company anticipates that this will result in accretion in revenue and earnings for the Company and will help to position it to have greater access to the capital markets and greater flexibility in raising additional capital to fund its growth in the near term.

Expansion of SMA Platform

The Company will also originate, underwrite, and service separately managed accounts (“SMAs”) on behalf of insurance company counterparties, producing assets rated CM1 (highest quality commercial mortgages) or CM2 (high quality commercial mortgages) under National Association of Insurance Commissioners regulatory capital standards. The Company also anticipates producing assets rated CM3, CM4, and CM5 as it expands its platform. As part of its business, the Company will manage all originated loans through their full lifecycle, encompassing active borrower surveillance, loan modifications and extensions, construction draw oversight, payoff strategy, and comprehensive third-party reporting. It will also provide primary and special servicing for its own portfolio and, selectively, for third-party mandates, and where workout strategies result in foreclosure, the Company will hold, manage, and monetize the acquired real estate on behalf of its investors. While the Company has not yet entered into a definitive agreement with the insurance counterparty, it is currently operating under a letter of intent on a limited basis in providing the foregoing services to these SMAs. The Company anticipates entering into a definitive agreement in the near term and expanding the SMA business.

Potential Strategic Acquisition

From time to time, the Company may evaluate strategic acquisition opportunities to expand its platform in furtherance of its growth strategy. The Company has identified White Oak Capital Holdings, LLC, an affiliate of the Company and a national provider of structured financing solutions for commercial real estate, as such a potential opportunity due, in part, to its majority ownership of Johnson Capital Multifamily, LLC (“Johnson Capital Multifamily”). Johnson Capital Multifamily is an FHA-approved multifamily accelerated processing lender that originates long-duration, government-backed permanent financing for multifamily, affordable housing, senior living and healthcare properties. For each loan it closes, Johnson Capital Multifamily receives upfront structuring fees of up to 3.5% of the principal amount of such loan and an ongoing loan servicing fee of about 0.25% of the outstanding principal amount of such loan per annum. Each loan can have a term of up to 40 years, providing lasting revenue for Johnson Capital Multifamily. Johnson Capital Multifamily provides the Company with the ability to convert certain of the bridge loans provided by the Sponsored Funds into FHA-backed term loans, allowing the Company to maintain the full economic relationship within the Company’s platform from origination to long-term loan servicing. The Company believes approximately 25% of its current portfolio of bridge loans could be eligible for conversion to FHA-backed term loans.

To date, the Company has only identified White Oak Capital Holdings, LLC as a potential strategic acquisition opportunity. No definitive terms, valuation, or structure for such an acquisition have been proposed or discussed by either party. There can be no assurance that the Company will ultimately pursue such an acquisition nor that such an acquisition would be consummated if pursued.

UNAUDITED PRO FORMA FINANCIAL INFORMATION

On August 21, 2026, we completed our reorganization in which our Predecessor companies were merged into The Oak Companies, Inc. (the “Reorganization”).

The following unaudited pro forma financial information is presented for illustrative purposes only with respect to the effect of the Reorganization, as if it had been completed at an earlier date. This information is derived from the historical consolidated financial statements of the Company and Predecessors, and has been adjusted as described in the accompanying notes. The Company has prepared the Statements based on available information using assumptions that it believes are reasonable. The assumptions, estimates, and adjustments described in the notes are preliminary and have been made solely for purposes of developing the pro forma information set forth below. The Reorganization generally resulted in no change to the assets and liabilities of the Company, including its predecessors. The primary changes to the financial statements that would have resulted from the Reorganization relate to the stockholders equity section (to reflect that the Reorganization results in the Company having stockholders rather than members) and to reflect that the Company will become a tax-paying rather than a pass-through entity. Furthermore, the information set forth below does not purport to project the financial position or results of the Company as of the current or any future date.

The pro forma financial information combines the historical consolidated financial statements of the Company and Predecessors, have been prepared assuming the Reorganization closed on December 31, 2025, and includes preliminary adjustments to reflect the events that are directly attributable to the Reorganization and factually supportable. The actual results reported by the combined company in periods following the Reorganization may differ significantly from the information set forth below, including the fact that the information does not account for the cost of any restructuring activities or synergies resulting from the Reorganization or other costs relating to the Reorganization.

In part, because the pro forma financial information has been condensed so as not to separately reflect certain balance sheet items that comprise less than 10% of total assets and certain statement of income items that comprise less than 20% of revenues, it should be read in conjunction with the Predecessors’ historical consolidated financial statements and accompanying notes included in this Offering Circular at pages F-1 through F-37, as well as Management’s Discussion and Analysis of Financial Condition and Results of Operation, beginning at page 45.

UNAUDITED PRO FORMA CONDENSED COMBINED BALANCE SHEET

As of December 31, 2025

UNAUDITED PRO FORMA CONDENSED COMBINED STATEMENT OF INCOME

For the year ended December 31, 2025

NOTES TO UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL STATEMENTS

Note 1 – description of the Reorganization

The Oak Companies, Inc. (the “Company”) was formed by Red Oak Capital Holdings, LLC on June 12, 2026 solely for the purpose of engaging in a business combination transaction pursuant to which Red Oak Capital Holdings, LLC and its subsidiaries (the “Predecessors”) would be merged into the Company.

The Company has had no business activity or operations other than in preparation for the consummation of the business combination transaction, and preparation for offerings Series H-Preferred Offering and Series A Preferred Stock pursuant to Securities Act Rule 506(b) and this Offering.

Note 2 – basis of Presentation

The unaudited pro forma condensed combined balance sheet as of December 31, 2025 sets forth the historical consolidated balance sheet of the Predecessor and has been prepared as if the Reorganization occurred on December 31, 2025. The unaudited pro forma combined statement of operations is prepared as if the Reorganization occurred on January 1, 2025. The unaudited pro forma condensed combined financial statements have also been adjusted to give effect to pro forma events that are directly attributable to the Reorganization, factually supportable and expected to have a continuing impact on the combined results.

NOTE 3 – ADJUSTMENTS TO UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL INFORMATION

Prior to the Reorganization and merger, the Predecessor has historically operated as a limited liability company taxed as a partnership for U.S. federal and state income tax purposes. For purposes of the Offering Statement of which this Offering Circular is a part, the accompanying pro-forma financial information reflects the income tax effects as if the business combination had occurred, resulting in the Company having operated as a taxable C-corporation for the year ended December 31, 2025. The pro forma income tax provision has been prepared using the asset and liability method in accordance with ASC 740, Income Taxes.

MANAGEMENT’S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION
AND RESULTS OF OPERATIONS

The following discussion and analysis of our financial condition and results of operations should be read together with the audited financial statements of our predecessor company, Red Oak Capital Holdings, LLC, along with the related notes to those financial statements that appear at pages F-1 through F-37 of this Offering Circular (the “Consolidated Financial Statements”). This discussion and analysis contains forward-looking statements reflecting our current expectations that involve risks and uncertainties. Actual results and the timing of events may differ materially from those contained in these forward-looking statements due to a number of factors, including those discussed in the section entitled “Risk Factors” as disclosed in this Offering Circular, as it may be amended or supplemented from time to time, and as they may be updated from time to time by our future filings under Regulation A.

The following discussion includes information from the audited financial statements for the year ended December 31, 2025, compared to the year ended December 31, 2024. References in this discussion to “2025” and “2024” mean, respectively, our fiscal years ended December 31, 2025 and December 31, 2024.

General

The Oak Companies, Inc. (the “Company”) is a newly-formed Delaware corporation established by Red Oak Capital Holdings, LLC the “Predecessor”) solely to enter into a business combination with and be the successor to the Predecessor, a Charlotte, North Carolina based commercial real estate finance company specializing in the acquisition, processing, underwriting, operational management and servicing of commercial real estate debt instruments.

Our merger with the Predecessor is intended to further streamline our various businesses and, through converting to a corporation, enhance our ability to raise capital. Prior to the merger, the Company will have had no business activities or operations other than in preparation for the merger and to prepare for certain capital raising activities that are expected to take place immediately following the effectiveness of the merger.

We sponsor and manage a family of CRE credit funds, originating senior secured, first-lien bridge loans focusing on the $2–$20 million CRE lending segment. We historically derive our revenues primarily from (i) the net cash flows from consolidated loans made to borrowers by the Sponsored Funds, and (ii) management fees, origination fees, servicing fees and disposition fees from the CRE loans that we originate, service and manage on our various platforms.

Conversion to Corporation

The Predecessor is a limited liability company that has historically been taxed as a partnership whereby no provision for income taxes was made at the entity level and tax consequences flowed to its members. The Company, conversely, will be subject to income taxes at the corporate level as a c-corporation and as such will need to record a provision for income taxes going forward. Assuming the Predecessor had been taxed as a corporation in 2025, we expect it would have recognized a tax benefit which would have offset the net operating loss and given rise to a deferred tax asset. This deferred tax asset would be offset by a valuation allowance reflective of the expected ability of the predecessor to utilize the net operating loss (NOL) carry forward to reduce taxable income in future periods.

Trends

The Predecessor’s loan portfolio experienced elevated credit stress during 2025, consistent with broader pressures across the commercial real estate sector, including elevated interest rates, tighter credit conditions, and softer valuations in certain property types. The number of loans on non-accrual status increased to nine as of December 31, 2025 from four as of December 31, 2024, and gross mortgage loans receivable that were 90 or more days past due totaled approximately $59.2 million at year-end. The weighted average interest rate on the portfolio declined to 11.24% at December 31, 2025 from 12.00% at December 31, 2024, and the loan count declined to 28 from 33, primarily reflecting payoffs, note sales, and the transfer of defaulted loans to real estate owned.

Management responded to these conditions by accelerating the resolution of non-performing assets. During 2025, the Predecessor and its consolidated funds transferred approximately $33.6 million of loans to real estate owned through foreclosure, completed a number of borrower payoffs and settlements (including The Oaks Senior Living and Patio Theater Holdings), and executed note and property sales to recover capital. These resolution activities reduced mortgage interest income in the near term but are intended to convert non-performing exposures into realizable value.

Two of the Predecessor’s consolidated funds warrant specific mention: Red Oak Capital Fund III, LLC (“ROCF III”) and Red Oak Capital Fund Series, LLC (“ROCFS”). ROCF III adopted the liquidation basis of accounting effective December 1, 2025 and, on November 21, 2025, executed a forbearance agreement with its bond trustee while it pursues an orderly plan of liquidation, including the completion and stabilization of two operating hotels, the Vue Hotel and the Bridges Hotel, both located in Natchez, Mississippi. Under the terms of the agreement, the maturity date of the ROCF III Series B Bonds, with outstanding principal of approximately $44.0 million, has been extended from December 31, 2025, to October 31, 2027, coinciding with the end of the forbearance period. ROCF III’s investments were 100% sourced by the legacy management team that was in place prior to the 2022 buyout led by Gary Bechtel and Ray Davis. With respect to ROCFS, Series II, the successor to Red Oak Capital Fund II, was also initiated by prior management and suffered significant impairment. All of the Series II legacy investments, however, have been realized. Also, in ROCFS, the Series IV Series B Bonds (8.25%) and Series Rb Bonds (9.00%) mature on June 30, 2026 and management has notified bondholders of its intent to extend that maturity to December 31, 2026.

Substantially all of the loans currently in workout or foreclosure were originated under the Predecessor’s legacy underwriting framework. During 2025, management implemented significant enhancements to its underwriting and credit process, including upgrades to credit analysis, collateral valuation, loan structuring, and ongoing portfolio monitoring, together with a shift toward variable-rate loan structures priced at SOFR plus a margin. Management believes these enhancements have strengthened the credit profile of loans originated under the current framework, and that newer originations, which are underwritten to these enhanced standards, are better positioned to perform across a range of market conditions.

Looking to 2026, management expects continued, though moderating, workout activity as remaining non-accrual loans are resolved through payoffs, note sales, or foreclosure. Several material resolutions have already occurred subsequent to year-end, including the full payoff of the Princeton Development loan in June 2026, the payoff of the Prime Realty Ventures loan in February 2026, and the approximately $8.7 million payoff of the Sharif Capital loans in April 2026. Management also expects to complete the renovation of, and stabilize occupancy at, the two Natchez, Mississippi hotels during 2026. Management intends to use a substantial portion of the net proceeds of this Offering to retire maturing fund debt, principally the ROCF IV Series Bonds; to the extent the Offering is successful, management anticipates a corresponding reduction in consolidated interest expense in the second half of 2026.

Management maintains a robust pipeline of loan origination opportunities within its target $2 million to $20 million commercial real estate bridge-lending segment, and expects origination activity to grow as capital becomes available through the Offering, the Cross River Bank facility, and the institutional participation program described below. There can be no assurance as to the volume or timing of any future originations.

In addition, the Predecessor has identified, and has begun working with, multiple institutional partners to establish a loan participation program. Under this program, an institutional partner holds a majority of the loan principal in an ‘A’ note or priority position, while one or more of the Sponsored Funds hold a minority ‘B’ note or subordinate position. To facilitate these arrangements, the Series Funds formed dedicated holding and special-purpose entities during 2025. Because the interest rate payable to the institutional A-note holder is generally lower than the interest rate paid by the borrower, the resulting excess interest spread accrues to the Sponsored Fund holding the subordinate B note, and the A-note holder generally retains a smaller share of the related fee income. As a result, a Sponsored Fund can earn an enhanced yield on a smaller amount of invested capital, which management believes is accretive to the returns of the participating Sponsored Funds while also freeing fund capital to support additional originations. Management believes this program enhances the flexibility and liquidity of the Oak lending platform and is expected to increase loan origination volume. No assurances can be made that these participations with institutional partners will be successful or will continue.

Consolidation Matters

The Consolidated Financial Statements present Red Oak Capital Holdings, LLC together with the Sponsored Funds and related special-purpose entities that it controls. Under ASC 810, the Predecessor has determined that all consolidated entities other than Red Oak Capital Holdings, LLC, Red Oak Capital GP, LLC, and Red Oak Financial, LLC are variable interest entities (VIEs) of which it is the primary beneficiary, principally through Red Oak Capital GP, LLC’s role as managing member or general partner. As a result, the assets, liabilities, revenues, and expenses of the Sponsored Funds are presented on a consolidated, gross basis.

This consolidation has a significant effect on the presentation of the loan portfolio and the related bonds. The mortgage loans receivable held by the Sponsored Funds (approximately $163.9 million, net, at December 31, 2025) and the foreclosed real estate held by those funds (approximately $67.6 million at December 31, 2025) are reflected as assets of the consolidated group, while the bonds issued by the funds (approximately $294.1 million, net, at December 31, 2025) and the Cross River Bank credit facility are reflected as consolidated liabilities. Importantly, these bonds and the credit facility are obligations solely of the respective issuing or borrowing funds, are secured by the assets of those funds, and are non-recourse to Red Oak Capital Holdings, LLC, which does not guarantee them. The assets of each consolidated VIE may be used only to settle the obligations of that VIE.

Consolidation also affects the presentation of revenues. Management, origination, servicing, and disposition fees earned by the Predecessor and Red Oak Capital GP, LLC from the Sponsored Funds, together with inter-fund loan participations and intercompany interest, are eliminated in consolidation because they represent transactions among entities under common control. Consequently, fee revenue that the Predecessor earns at the management-company level is substantially eliminated against the corresponding expense recorded by the funds and is not separately visible in the consolidated statements of operations. The standalone results of Red Oak Capital Holdings, LLC and its direct subsidiaries are presented in the Supplementary Information accompanying the Consolidated Financial Statements and are discussed under “Holding Company (Standalone) Results” below.

Sponsored Funds (VIEs)

As of the date of this Offering Circular, there are five Sponsored Funds: Red Oak Capital Fund III, LLC; Red Oak Capital Fund VI, LLC; Red Oak Capital Fund VII, LLC; Red Oak Income Opportunity Fund II, LLC; and Red Oak Capital Fund Series, LLC, each of which is described in more detail below:

Red Oak Capital GP, LLC

Red Oak Capital GP, LLC (“ROGP”) is our wholly owned subsidiary and serves as the managing member of the Sponsored Funds.

In connection with the Sponsored Funds, ROGP collects various fees from the Sponsored Funds that consist of offering-related fees, asset management fees, and loan disposition fees, although not all fee types are collected from each Sponsored Fund. In addition, ROGP is the sole equity holder in the Sponsored Funds capitalized by debt offerings, or “Debt Funds.” ROGP may receive distributions on its equity in the Sponsored Funds following the payment of required interest and principal payments to bondholders in the Debt Funds. As the sole equity holder, the activities of the Sponsored Funds are consolidated on our financial statements included herein.

In connection with each offering conducted by a Sponsored Fund, ROGP collects an organizational and offering fee equal to 2.0% of the gross offering proceeds from such offering, though the organizational and offering fee is reduced by the actual organization and offering costs for the offering incurred by such Sponsored Fund.

ROGP will also be paid certain fees by the Sponsored Funds related to their operating activities. While the fees paid by each Sponsored Fund vary, such fees are generally comprised of quarterly asset management fees, acquisition fees, and disposition fees. The quarterly asset management fees generally equal either (i) 1.00% per annum of (a) all capital invested by investors in a Sponsored Fund, net of any amounts invested at that time by the Sponsored Fund in loans or debt instruments, plus (b) the outstanding principal amount of each loan or real estate debt instrument then held by a Sponsored Fund, including loans secured by real estate then owned as a result of borrower default or (ii) 0.25% to 1.75% per annum of the gross principal outstanding of all bonds offered by a Sponsored Fund. Acquisition fees generally equal 0.50% of a Sponsored Fund’s gross mortgage loans receivable, inclusive of any closing costs. Disposition fees generally equal 0.50% to 1.00% of proceeds received from the repayment of the principal amount of debt investments to a Sponsored Fund or any other disposition of the underlying real estate by a Sponsored Fund. As noted above, not all Sponsored Funds pay the same types of fees, and even if two Sponsored Funds pay the same type of fee, the amount of such fee may vary.

Red Oak Financial, LLC

Red Oak Financial, LLC (“Red Oak Financial”) is our wholly owned subsidiary and originates the commercial real estate loans for the Sponsored Funds. Red Oak Financial operates within an extensive network of contacts with expansive market reach to source meaningful deal flow. Red Oak Financial will seek mortgage loan originator licenses in various states as required. Red Oak Financial will earn origination fees on the loans it sources. These origination fees are typically based on a percentage of the principal amount of the applicable loan, most commonly 1.0% or 2.0% of principal. Origination fees paid to Red Oak Financial are paid by the borrower of any loan originated by Red Oak Financial and not the Sponsored Fund making the loan. Red Oak Financial may also charge such borrowers asset management fees, servicing fees, special servicing fees, and merchant banking fees.

Loan Portfolio

As of December 31, 2025, through certain of the Sponsored Funds and direct holding company participations, the Company held 28 senior secured loans, providing $178.4 million of senior secured loans to various borrowers, which is gross of approximately $7.5 million of participation loans payable and excludes one related party loan between Red Oak Capital Fund III, LLC (borrower) and Red Oak Income Opportunity Fund II, LLC (lender) with principal of approximately $1.7 million. Such related party loan is included in the table below but eliminated upon consolidation, as further described in the footnotes to the table. The portfolio of loans possessed a weighted average interest rate of 11.24% and a weighted average additional paid-in-kind (“PIK”) interest rate of 0.65%. The portfolio loans have maturities ranging from June 2024 to November 2027. The following table outlines the major terms of each outstanding loan at December 31, 2025:

Real Estate Owned Portfolio

As of December 31, 2025, through certain of the Sponsored Funds and direct holding company ownership, the Company held eight properties, with an aggregate net carrying value of $67.6 million. All properties were acquired through foreclosure. The Angler Hotel was effectively acquired through foreclosure by ROCF II Series and subsequently transferred to Red Oak Capital Properties, LLC prior to that entity’s merger with and into Red Oak Capital Holdings, LLC. The following table outlines the Company’s real estate owned portfolio as of December 31, 2025:

Results of Operations for the years ended December 31, 2025 and December 31, 2024

Overview

On a consolidated basis, the Predecessor recorded a net loss of approximately $31.4 million for the year ended December 31, 2025, compared to a net loss of approximately $30.1 million for the year ended December 31, 2024. As discussed under “Consolidation Matters,” the consolidated net loss is driven predominantly by the Sponsored Funds. The funds’ non-recourse bond interest expense and credit- and real-estate-related losses are consolidated on a gross basis.

Management believes that a substantial portion of the 2025 consolidated net loss is attributable to items that are non-recurring or non-cash in nature, or that relate to the transitional ownership and resolution of foreclosed assets, and that are not representative of the ongoing earnings capacity of the business. The following table reconciles the reported consolidated net loss to a management-adjusted net loss. The adjusted measure is a non-GAAP financial measure, is presented for supplemental informational purposes only, and should not be considered in isolation from, or as a substitute for, net loss determined in accordance with GAAP.

Reconciliation of Consolidated Net Loss to Management-Adjusted Net Loss — Year Ended December 31, 2025

Foreclosed properties held for sale may continue to generate net operating losses until they are sold, and provisions for loan losses are an inherent and recurring feature of a commercial real estate lending business. These adjustments are presented to illustrate the magnitude of items that management views as outside its normalized operating performance and are subject to the more detailed discussion in the line-item analysis below and in the notes to the Consolidated Financial Statements.

Net Interest Spread

Net interest spread — total interest income (mortgage interest income plus paid-in-kind interest income) less interest expense — was approximately $(13.3) million for the year ended December 31, 2025. Two factors are relevant to an assessment of this figure. First, consolidated interest expense includes a significant non-cash component: amortization of debt issuance costs (DIC) of approximately $4.7 million for 2025 (2024: approximately $4.5 million), which is recorded within interest expense but requires no current cash outlay. Second, because nine loans were on non-accrual status as of December 31, 2025, interest income excludes contractual interest on those loans, a portion of which management estimates could be recovered upon resolution.

The following table presents net interest margin on a GAAP basis and, on an illustrative basis, after adjusting for the non-cash DIC amortization and for management’s estimate of potential recoveries of interest on non-accrual loans. The cash-basis and adjusted figures are non-GAAP measures presented for supplemental informational purposes only.

Net Interest Spread — Year Ended December 31, 2025

Mortgage Interest Income

Total mortgage interest income for the years ended December 31, 2025 and 2024 were approximately $16.7 million and $20.8 million, respectively. The reduction in mortgage interest income of approximately $4.1 million was primarily attributable to the placement of additional loans on non-accrual status and the transfer of defaulted loans to real estate owned during 2025. The number of loans on non-accrual status increased to nine at December 31, 2025 from four at December 31, 2024, and approximately $33.6 million of loans were transferred to real estate owned through foreclosure during the year. In addition, the weighted average interest rate on the portfolio declined to 11.24% from 12.00%, the loan count declined to 28 from 33, and approximately $0.5 million of previously accrued interest was reversed in connection with loans placed on non-accrual status. The decline in the weighted average interest rate was also influenced by the market-wide decrease in SOFR during 2025, as the Predecessor’s variable-rate loans are priced at SOFR plus a margin.

Paid-in-Kind Interest Income

Total paid-in-kind interest income for the years ended December 31, 2025 and 2024 were approximately $0.8 million and $1.9 million, respectively. The reduction in paid-in-kind interest income of approximately $1.1 million was primarily attributable to the continued runoff of the Predecessor’s legacy loans that carried a paid-in-kind interest feature. The Predecessor discontinued originating loans with a paid-in-kind interest feature several years ago and now originates loans bearing a variable interest rate based on SOFR plus a margin. As the remaining legacy paid-in-kind loans are repaid, paid off, or placed on non-accrual status, paid-in-kind interest income has correspondingly declined, and the weighted average paid-in-kind interest rate on the portfolio decreased to 0.65% from 0.86%.

Property Income

Total property income for the years ended December 31, 2025 and 2024 was approximately $2.4 million and $0.5 million, respectively. The increase in property income is attributable to the increased number of foreclosed properties owned and operated during 2025. The Predecessor owned three hotels at December 31, 2025: The Angler (HLLT), which was in operation throughout 2025, and two hotels located in Natchez, Mississippi, one of which reopened in the second quarter of 2025 following renovation and the other of which is expected to return to service in 2026. Property income is derived from these operating hotels, with the year-over-year increase driven by the full-year operation of The Angler together with the reopening of one of the Natchez hotels during 2025.

Loan Service Fee Income

Total loan service fee income for the years ended December 31, 2025 and 2024 was approximately $0.9 million and $0.2 million, respectively. The increase in loan service fee income is attributable to increased loan servicing and special-servicing activity during 2025, including fees earned in connection with the workout, modification, and resolution of defaulted and non-performing loans.

Management Fee Income

Total management fee income for the years ended December 31, 2025 and 2024 was approximately $33,000 and $44,000, respectively. Total management fee income represents the net amount of management fee income remaining after the elimination, in consolidation, of management fees paid by the consolidated Sponsored Funds to Red Oak Capital GP, LLC. Because the Sponsored Funds are consolidated, the management fees they pay are eliminated against the corresponding fee revenue earned by Red Oak Capital GP, LLC. On a standalone basis, Red Oak Capital GP, LLC and the Predecessor earned approximately $4.7 million of management fee income during 2025, substantially all of which was eliminated in consolidation; the residual amount reflected in the consolidated statements of operations relates to fees earned from entities that are not consolidated.

Other Income

Total other income for the years ended December 31, 2025 and 2024 was approximately $0.5 million and $0.4 million, respectively. Total other income consists primarily of late fees, extension and other ancillary charges assessed to borrowers, and miscellaneous income. The increase in total other income was attributable to higher late-fee and ancillary-charge activity associated with the increased volume of loan defaults and workouts during 2025.

Interest Expense

Total interest expense for the years ended December 31, 2025 and 2024 was approximately $30.8 million and $29.2 million, respectively. The increase in total interest expense of approximately $1.6 million was attributable to the full-year effect of bonds issued in late 2024 and during 2025 (including the ROCF II Series C Bonds issued in December 2024 and the ROIOF II Series B Bonds), together with borrowings under the Cross River Bank credit facility and notes payable entered into during 2025. Interest expense for 2025 includes approximately $4.7 million of non-cash amortization of debt issuance costs (2024: approximately $4.5 million); cash interest paid on the bonds was approximately $22.3 million for 2025. Net proceeds from this Offering, together with other potential sources of liquidity, are expected to be used to pay down the bonds outstanding for ROCF IV, which we anticipate will reduce interest expense in the second half of 2026.

Professional Fees

Total professional fees for the years ended December 31, 2025 and 2024 were approximately $3.2 million and $3.2 million, respectively. Total professional fees consist of legal, audit, accounting, tax, and other advisory fees. Professional fees remained elevated in 2025, consistent with 2024, reflecting costs associated with loan workouts and restructurings, the Red Oak Capital Fund III forbearance, the merger of Red Oak Capital Properties, LLC into the Predecessor, and preparation for the Company’s planned capital-raising activities.

General and Administrative

Total general and administrative expenses for the years ended December 31, 2025 and 2024 were approximately $5.9 million and $6.7 million, respectively. The decrease of approximately $0.8 million in general and administrative expenses during 2025 was primarily related to reductions in compensation and other operating costs as the Predecessor streamlined its operations. Substantially all general and administrative expense is incurred at the holding-company level; on a standalone basis, Red Oak Capital Holdings, LLC incurred approximately $5.9 million of general and administrative expense during 2025.

Provision for Credit Losses

Total provision for credit losses for the years ended December 31, 2025 and 2024 was approximately $2.0 million and $9.1 million, respectively. The lower provision recorded in 2025 should not be read as a reduction in credit reserves; the allowance for credit losses in fact increased by approximately $2.0 million, to approximately $13.8 million at December 31, 2025 from approximately $11.9 million at December 31, 2024. During 2025, the Predecessor recorded gross additions to the allowance of approximately $5.8 million as conditions in portions of the portfolio deteriorated, which were partially offset by approximately $2.3 million of recoveries and approximately $1.6 million of charge-offs recognized as previously impaired loans were resolved through foreclosure, payoff, or sale. The provision reflected in the consolidated statement of operations represents the net increase in the allowance during the year.

Depreciation Expense

Total depreciation expense for the years ended December 31, 2025 and 2024 was approximately $0.4 million and $0.3 million, respectively. The increase in depreciation expense during 2025 was due to the increase in the number of foreclosed operating properties, principally hotels, that were in service during the year.

Property Expenses

Total property expenses for the years ended December 31, 2025 and 2024 were approximately $5.7 million and $2.6 million, respectively. The increase in property expenses during 2025 was due to the operating costs of foreclosed properties held for sale, principally the operating hotels in Natchez, Mississippi, including costs associated with renovation and reopening activities during the year.

Due Diligence Expense

Total due diligence expenses for the years ended December 31, 2025 and 2024 were approximately $6,700 and $0.2 million, respectively. The decrease in due diligence expenses during 2025 was due to fewer Sponsored Fund offerings conducted through the retail broker-dealer channel during the year.

Realized and Unrealized Losses on Investments

For the year ended December 31, 2025, the Predecessor recognized a net loss on realized and unrealized investments of approximately $(4.6) million, consisting of a realized gain on extinguishment of debt of approximately $0.6 million, a realized loss on investments of approximately $(10.0) million, and net unrealized appreciation of approximately $4.8 million. The realized loss on investments was driven principally by the 2025 dispositions of foreclosed real estate, including the sale of the property formerly held by ROCFII La Scarola, LLC (realized loss of approximately $3.3 million) and the sale of the hotel formerly held by ROCFIII OM, LLC (realized loss of approximately $5.7 million). The net unrealized appreciation primarily reflects fair-value recoveries on investments held by Red Oak Capital Properties, LLC prior to its merger into the Predecessor on June 30, 2025.

Reconciliation of Cumulative (Inception-to-Date) Net Loss — Consolidated VIEs

The cumulative inception-to-date losses presented below are concentrated in the Predecessor’s legacy inherited funds — Red Oak Capital Fund II and Red Oak Capital Fund III — which were underwritten under the prior management team’s framework and account for the substantial majority of the deficit. The current lending platform (Funds IV, V, ROIOF, VI, VII, ROIOF II and ROCFS) reflects a materially smaller cumulative loss, a significant portion of which is non-cash or subject to recovery, as shown in the table and notes below.