Frequently Asked Questions.

The Oak Companies, Inc. (“Oak”) is a Charlotte, North Carolina–based, vertically integrated commercial real estate finance platform: it sponsors and manages a family of CRE credit funds, originates senior secured first-lien bridge loans of $2–$20 million on income-producing property, and services and asset-manages those loans through their full lifecycle.

The Company will serve as the parent company of the various operating businesses that make up the Company’s operating platform, which include a family of commercial real estate credit funds (the “Sponsored Funds”) that are sponsored by the Predecessor and originate senior secured, first-lien bridge loans; Red Oak Capital GP, LLC (“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, LLC (“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

Oak is headquartered in Charlotte, North Carolina.

The Company will operate under the direction of its Board of Directors, which is currently comprised of Gary R. Bechtel, Kevin P. Kennedy, and Raymond T. Davis. While the Board of Directors is ultimately responsible for the management and control of the Company’s affairs, the Company’s management team will oversee the day-to-day operations of the Company, including all aspects of the Company’s platform. The Company’s management team is comprised of Gary R. Bechtel, Kevin P. Kennedy, Raymond T. Davis, Paul Cleary, Thomas McGovern, and Matthew Webster.

The Company believes it is 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 SMAs at scale. The loans originated by the Company are 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. By targeting the $2 million to $20 million commercial real estate lending segment, the Company is 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 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.

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.

Oak intends to apply to have the Common Shares listed on the NYSE American (“NYSE American”) under the symbol “OKRE” but has yet to make an application with the exchange. If the Common Shares are not approved for listing on the NYSE American, Oak will not complete the listing contemplated hereby. No Assurance can be given that Oak’s application to list on NYSE American will be made and if made that it will be approved or that an active trading market for the Common Shares will develop.

The Oak Companies, Inc. (“Company” or “Oak”) is offering securities through the use of an Offering Statement that has been qualified by the U.S. Securities and Exchange Commission (the “SEC”) under Tier II of Regulation A. Digital Offering, member FINRA/SIPC is the broker-dealer of record for this offering. Before making any investment, you are urged to read the final Offering Circular that forms a part of the Offering Statement that has been filed with the SEC carefully for a more complete understanding of Oak and the offering.

You can purchase shares in public offering by visiting https://app.equidefi.com/offerings/TOCI/registration and hit the invest now button

Shares of Series R Convertible Preferred Stock (the "Preferred Shares").

$10.00 per Preferred Share.

$1,000 for 100 Preferred Share.

No, you do not need to be accredited

Up to $25 million, with the ability to increase to $35 million (if the maximum offering amount is increased in the sole discretion of the Board of Directors). However, the Company is not required to sell any specific number or dollar amount of Preferred Shares in this private offering. As such, the Company may sell less than the maximum number of Preferred Shares offered, and the Company may receive less than the maximum amount of proceeds referenced above.

Oak anticipates that up to 10.0% of the proceeds from the Offering will be used to pay placement agent fees and for other organizational and offering expenses related to the Offering. The remaining 90.0% of the offering proceeds will be used 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. See the “Estimated Use of Proceeds to Issuer” section of the Offering Circular for more information.

Yes, as described above, Oak Companies, Inc. (“Company” or “Oak”) is conducting this offering pursuant to Regulation A through the use of an Offering Statement that has been qualified by the U.S. Securities and Exchange Commission (the “SEC”) under Tier II of Regulation A. Digital Offering, member FINRA/SIPC is the broker-dealer of record for this offering. Please review the final Offering Circular for a detailed risks related to this offering.

There is currently no existing public trading market for the Series R Preferred Shares, and if a public market develops following the offering, it may not continue.

If the Company consummates its Public Listing, the Preferred Shares will be convertible into shares of Common Stock of the Company. Upon such conversion and subject to any additional adjustments as may be required pursuant to the anti-dilution provisions of the Preferred Shares, the Preferred Shares will be converted into a number of shares of common stock of the Company equal to the quotient obtained by dividing the then current conversion preference of the Series R Preferred Shares then outstanding, plus accrued but unpaid dividends not then included in the Conversion Preference, by seventy five percent (75%) of the price per share or deemed price per share to the public in the Qualified IPO, rounded to the nearest whole share. Oak intends to apply to have the Common Shares listed on the NYSE American (“NYSE American”) under the symbol “OKRE” but has yet to make an application with the exchange. If the Common Shares are not approved for listing on the NYSE American, Oak will not complete the listing contemplated hereby. No Assurance can be given that Oak’s application to list on NYSE American will be made and if made that it will be approved or that an active trading market for the Common Shares will develop.

Yes, the Preferred Shares will carry an annual dividend payment of 9% of the price per share. Each holder of the then outstanding Series R Preferred Stock shall be entitled to receive, when and as authorized by the Board, out of funds legally available for the payment of dividends, cumulative preferential cash dividends at the rate of 9.0% per annum of the Stated Value, plus an amount equal to all accumulated and unpaid dividends thereon. Dividends on the Series R Preferred Stock shall accrue annually, beginning from the date of the issuance of the shares, and will accrue until the conversion, redemption or liquidation of the shares. Accrued dividends will convert into shares of Class A voting Common Stock upon the occurrence of a Listing Event at a 25% discount to the Listing Price (as defined below) of the shares of Class A Common Stock. Notwithstanding the foregoing, in the event a conversion, redemption or liquidation occurs prior to the end of a year, the portion of dividends shall be paid with respect to such partial year. Dividends shall be calculated on the basis of a calendar year consisting of twelve 30-day months (or 360 days).

The Preferred Shares will be convertible into shares of Class A Common Stock of the Company (the "Class A Common Stock"), in accordance with the terms and subject to the conditions set forth in the Certificate of Designation for the Preferred Shares.

Liquidity Event: Upon the occurrence of a Liquidity Event, each holder of Series R Preferred Stock shall be entitled to be paid an amount equal to the greater of (i) the Stated Value, plus any accrued but unpaid dividends on the shares held by such holder and (ii) the Transaction Value. A “Liquidity Event” means the (i) acquisition by any person, including any syndicate or group deemed to be a “person” under Section 13(d)(3) of the Exchange Act, directly or indirectly, through a purchase, merger or other acquisition transaction or series of purchases, mergers or other acquisition transactions of shares of the Company’s capital stock entitling that person to exercise more than 50% of the total voting power of all shares of the Company’s capital stock entitled to vote generally in elections of directors (except that such person will be deemed to have beneficial ownership of all securities that such person has the right to acquire, whether such right is currently exercisable or is exercisable only upon the occurrence of a subsequent condition); or (ii) sale, lease, exclusive license, transfer or other disposition, in a single transaction or series of related transactions, of all or substantially all of the assets of the Company. For the avoidance of doubt, a Listing Event shall not be deemed a Liquidity Event. “Transaction Value” means the value per share of cash and other property, if any, a holder or holders of Series R Preferred Stock would receive upon a Liquidity Event had such holder or holders, immediately prior to such Liquidity Event, converted such shares of Series R Preferred Stock into shares of Class A Common Stock issuable upon conversion of the Series R Preferred Stock. The value of any property other than cash shall be determined by the Board of Directors based on the imputed value of the Common Stock in the Liquidity Event transaction, acting in good faith on the basis of such information as it considers, in its reasonable judgment, appropriate.

Optional Redemption by Company: Upon the day following the third anniversary of the date of commencement of this Offering, the Company will have the right (but not the obligation) to redeem all or some portion of outstanding Series R Preferred Stock at a redemption price equal to 100% of the Stated Value, plus an amount equal to accrued but unpaid cash dividends thereon, to but not including the date of redemption. Any such redemption may be made conditional on such factors as may be determined by the Board of Directors and as set forth in the notice of redemption. If fewer than all of the outstanding Series R Preferred Stock are to be redeemed pursuant to the Company’s redemption right, the Series R Preferred Stock to be redeemed will be redeemed pro rata (as nearly as may be practicable without creating fractional shares), by lot or by any other equitable method that the Company determines.

Mandatory Conversion: Upon a Listing Event (as defined below), each outstanding share of Series R Preferred Stock then outstanding, as well as all then existing accrued but unpaid dividends thereon, shall automatically convert into that number of shares of Class A Common Stock determined by dividing the then Stated Value of such shares by the Discounted Listing Price (as defined below).A “Listing Event” means the initial listing of the Company’s shares of Class A Common Stock, or any equity equivalent into which shares of Class A Common Stock may convert for purposes of the listing, on the New York Stock Exchange, NYSE MKT, NASDAQ Stock Exchange, or any other “national securities exchange," that is registered with the U.S. Securities and Exchange Commission pursuant to Section 6 of the Exchange Act. “Listing Price” means the (i) offering price per share of the Class A Common Stock or any other class of Common Stock approved for the Listing Event if the Listing Event is in connection with an underwritten public offering or (ii) the opening price per share of such Common Stock on the Listing Event if the Listing Event is not in connection with an underwritten public offering

The "Conversion Price" of a Preferred Share shall equal a price per share determined by applying a 25% discount to the Listing Price.

When you complete the subscription by hitting invest now, you will be able to make payment to the escrow agent by credit card, wire transfer or ACH transfer.

No, the costs are the same, regardless of how you invest. However, your bank may charge you outgoing wire fees.

All funds are to be sent to our escrow agent, Wilmington Trust, and NOT to the Company. If you are making payment by wire transfer, funds should be wired to:

Wilmington Trust, N.A.

ABA #: 031100092

A/C #: 186047-000

A/C Name: Oak Companies REG A Escrow

Attn: Joseph M. Gribaudo

International Wires:

M&T

Buffalo, New York

ABA: 022000046

SWIFT: MANTUS33

Beneficiary Bank: Wilmington Trust

Beneficiary ABA: 031100092

A/C #: 186047-000

A/C Name: Oak Companies REG A Escrow

Wires and ACH are preferred but if you plan to pay by check, mail your check to the following address:

Oak Companies REG A Escrow

c/o Wilmington Trust

1100 North Market Street

Wilmington, DE 19890

Attn: Workflow Management

Investing in private companies is risky and there is no guarantee you will get a return on your investment or that you may be able to sell the Preferred Shares. However, an "exit" event could open up the opportunity where you could convert your shares into cash or more liquid assets. "Exits" include going public or getting acquired by another company or a financial investor. If the value of the Company grows, then could have a higher potential of making a profit on your investment in the Preferred Shares in connection with a potential exit event. No public market currently exists for the Preferred Shares (or the common shares into which the Preferred Shares may be converted).

Any investment in the Preferred Shares involves a high degree of risk. You should consider carefully the risk factors information, together with the other information contained in the Company’s final Offering Circular for a detailed risks related to this offering, before you decide to buy any Preferred Shares.

Preferred Shares that you purchase will be held in your name, in electronic form at the transfer agent for this private offering. No stock certificates will be sent to you, but you will receive a Welcome Letter directly from the Company’s transfer agent with information on how to access and manage your account within 30 days after the Company accepts your proposed investment in Preferred Shares.

Generally, a transfer agent maintains a record of ownership, including contact information, of an issuer’s registered stockholders.

Equity Stock Transfer 237 W 37th Street, Suite 602 New York, NY 10018

Main: 212.575.5757 Fax: 347.584.3644

www.equitystock.com

There is currently no public trading market for the Preferred Shares or the common shares into which the Preferred Shares may be converted, and there can be no assurance that any such public market will develop in the foreseeable future, if at all. This private offering relies upon exemptions from the registration requirements of federal and state securities laws. Those exemptions require that the securities be purchased for investment purposes only, and not with a current view toward their distribution or resale. Unless the Preferred Shares, or the common shares into which the Preferred Shares may be converted, are subsequently registered or qualified with the SEC and any required state securities authorities, or appropriate exemptions from registration are available, you may be unable to liquidate your investment in the Company even if your financial condition makes such liquidation necessary. Accordingly, prospective investors who require liquidity in their investments should not invest in the Preferred Shares. An investment in the Preferred Shares should only be made by those who can afford the loss of their entire investment.

If the Company consummates its Public Listing, the Preferred Shares will be convertible into shares of Common Stock of the Company. Upon such conversion and subject to any additional adjustments as may be required pursuant to the anti-dilution provisions of the Preferred Shares, the Preferred Shares will be converted into a number of shares of common stock of the Company equal to the quotient obtained by dividing the then current conversion preference of the Series R Preferred Shares then outstanding, plus accrued but unpaid dividends not then included in the Conversion Preference, by seventy five percent (75%) of the price per share or deemed price per share to the public in the Qualified IPO, rounded to the nearest whole share. Oak intends to apply to have the Common Shares listed on the NYSE American (“NYSE American”) under the symbol “OKRE” but has yet to make an application with the exchange. If the Common Shares are not approved for listing on the NYSE American, Oak will not complete the listing contemplated hereby. No Assurance can be given that Oak’s application to list on NYSE American will be made and if made that it will be approved or that an active trading market for the Common Shares will develop.

For additional detailed information we encourage you to read the Form 1 A in its entirety. If you have additional questions you can email our investment banker at oak@digitaloffering.com and a representative will be in touch with you. Please be sure to include your best daytime phone number and other contact information.