Exhibit 10.1

DEBT SATISFACTION AGREEMENT

Contract Date: July 25, 2025

“Parties” (each a “Party”):

Premises:

Agreement:

“Agreement” identifies this Debt Satisfaction Agreement.

“Brantl Receivable” identifies an obligation of Beeline to pay One Hundred Eighty-One Thousand Nine Hundred Fifty Six Dollars ($181,956) to Brantl for services rendered and cash disbursed on behalf of Beeline.

“Buyers” identifies Brantl, Grammen and Gwin collectively.

“Common Stock” means the common stock of BSC, par value $0.001 per share.

Exchange Shares” identifies the 530,000 shares of BSC Common Stock that will be assigned by Beeline to the Buyers at the Closing.

“Grammen Receivable” identifies an obligation of Beeline to pay One Hundred Three Thousand Six Hundred Eighty Dollars ($103,680) to Grammen for services rendered as a member of Beeline’s Board of Directors.

“Gwin Receivable” identifies an obligation of Beeline to pay Eighty-One Thousand Seven Hundred Sixty-Eight Dollars ($81,768) to Gwin for services rendered as a member of Beeline’s management.

“Contingent Obligation” means, as to any Person, any direct or indirect liability, contingent or otherwise, of that Person with respect to any indebtedness, lease, dividend or other obligation of another Person if the primary purpose or intent of the Person incurring such liability, or the primary effect thereof, is to provide assurance to the obligee of such liability that such liability will be paid or discharged, or that any agreements relating thereto will be complied with, or that the holders of such liability will be protected (in whole or in part) against loss with respect thereto.

“Indebtedness” of any Person means, without duplication (A) all indebtedness for borrowed money, (B) all obligations issued, undertaken or assumed as the deferred purchase price of property or services (including, without limitation, any such obligations which, in accordance with GAAP, consistently applied for the periods covered thereby, is classified as a capital lease) (other than trade payables entered into in the ordinary course of business), (C) all reimbursement or payment obligations with respect to letters of credit, surety bonds and other similar instruments, (D) all obligations evidenced by notes, bonds, debentures or similar instruments, including obligations so evidenced incurred in connection with the acquisition of property, assets or businesses, (E) all indebtedness created or arising under any conditional sale or other title retention agreement, or incurred as financing, in either case with respect to any property or assets acquired with the proceeds of such indebtedness (even though the rights and remedies of the seller or bank under such agreement in the event of default are limited to repossession or sale of such property), (F) all monetary obligations under any leasing or similar arrangement which, in accordance with GAAP, consistently applied for the periods covered thereby, is classified as a capital lease, (G) all indebtedness referred to in clauses (A) through (F) above secured by (or for which the holder of such indebtedness has an existing right, contingent or otherwise, to be secured by) any mortgage, claim, lien, tax, right of first refusal, pledge, charge, security interest or other encumbrance upon or in any property or assets (including accounts and contract rights) owned by any Person, even though the Person which owns such assets or property has not assumed or become liable for the payment of such indebtedness, and (H) all Contingent Obligations in respect of indebtedness or obligations of others of the kinds referred to in clauses (A) through (G) above.

“Person” means any individual, corporation, partnership, limited liability company, joint venture, estate, trust, unincorporated association, any other person or entity, and any federal, state, county or municipal government or any bureau, department or agency thereof and any fiduciary acting in such capacity on behalf of any of the foregoing.

The remainder of this page is intentionally blank. The signature page follows.

IN WITNESS WHEREOF, the parties have executed this Agreement.

[Signature Page to Debt Satisfaction Agreement]

APPENDIX A

Form of Buyer’s Release

The undersigned, pursuant to the Debt Satisfaction Agreement dated July 24, 2025, does forever discharge Beeline Holdings, Inc. and its subsidiaries (“Beeline”) of and from all, and all manner of, action, cause of action, suits, debts, dues, sums of money, accounts, reckonings, notes, bonds, bills, specialties, covenants, contracts, controversies, agreements, promises, variances, trespasses, damages, judgments, executions, claims, and demands whatsoever, in law or in equity, that I ever had, now have, or that any personal representative, successor, heir, or assign of mine hereafter can, shall, or may have, against Beeline for, upon, or by reason of any matter, cause, or thing whatsoever, up to and including the date of this Release. The foregoing notwithstanding, however, I specifically do not release Beeline from any obligation, present or future, to indemnify me against liability, whether said right to indemnification arises under a contract, Beeline’s Bylaws, or the laws of the State of Nevada applicable to corporations organized in that state.

Dated: July 25, 2025

APPENDIX B

Senior Secured Original Issue Discount Promissory Note and Security Agreement

[Attached] 

Exhibit 10.2

Senior Secured Original Issue Discount Promissory Note And Security Agreement

The undersigned maker (“Maker”) promises to pay to the order of Beeline Holdings, Inc., a Nevada corporation (“Lender) the principal sum of $100,000. In exchange for the delivery of this Senior Secured Original Issue Discount Promissory Note and Security Agreement (this “Note”), Lender shall lend to Maker $75,000, net of an original issue discount of $25,000.

Maker shall repay the outstanding principal evidenced by this Note as follows: (i) the principal sum of $50,000 of principal shall be due and payable on April 24, 2026, and (ii) the remaining $50,000 of principal plus all other amounts owing hereunder (if any) shall be due and payable on the 12-month anniversary of the issuance date hereof.

Maker hereby grants, assigns and pledges, and this Note hereby creates, a lien on and a first priority security interest in and to all of Maker’s Accounts, Goods, Inventory, Equipment, Investment Property, General Intangibles, Instruments, Documents, and all other assets and personal property of Maker, wherever located and whether now owned or existing or hereafter acquired or coming into existence, together with all of Maker’s right, title and interest therein and the proceeds now or hereafter arising in connection therewith (the “Collateral”), as collateral security for the payment and performance when due of all obligations and liabilities of Maker arising under or in connection with this Note. This Note shall constitute a security agreement under the Nevada Uniform Commercial Code and other laws applicable to the creation of liens on personal property. Capitalized terms used in this paragraph shall have the meanings that are given to them under the Nevada Uniform Commercial Code. Maker acknowledges and agrees that Lender shall have the right to file one or more UCC-1 financing statements and any renewals and continuations thereof and such other documents as Lender may reasonably require with respect to this Note and the security interest granted hereunder, and Maker hereby authorizes such filings and other actions as may be taken by and on behalf of Lender relating thereto and the security interests hereunder. If a default occurs under this Note, Lender shall have all rights and remedies of a secured party under the Nevada Uniform Commercial Code.

The following shall constitute an event of default under this Note, upon the occurrence of which the full principal amount and all other amounts due and payable under this Note shall become immediately due and payable:

(i) any default in the payment of the principal of or any other amount payable hereunder as and when the same shall become due and payable;

(ii) Maker or a subsidiary shall: (A) apply for or consent to the appointment of, or the taking of possession by, a receiver, custodian, trustee or liquidator of itself or of all or a substantial part of its property or assets; (B) make a general assignment for the benefit of its creditors; (C) commence a voluntary case under the United States Bankruptcy Code (as now or hereafter in effect) or under the comparable laws of any jurisdiction (foreign or domestic); (D) file a petition seeking to take advantage of any bankruptcy, insolvency, moratorium, reorganization or other similar law affecting the enforcement of creditors’ rights generally; (E) acquiesce in writing to any petition filed against it in an involuntary case under United States Bankruptcy Code (as now or hereafter in effect) or under the comparable laws of any jurisdiction (foreign or domestic); (F) issue a notice of bankruptcy or winding down of its operations or issue a press release regarding same; or (G) take any action under the laws of any jurisdiction (foreign or domestic) analogous to any of the foregoing; or any corporate or other action is taken by Maker for the purpose of effecting any of the foregoing;

(iii) Maker shall fail to observe or perform any other covenant, condition, obligation or agreement contained in this Note or any other agreement entered into between Maker and Lender;

(iv) Maker or any of its subsidiaries shall (A) default in any payment of any amount or amounts of principal of or interest (if any) on $10,000 or more of any indebtedness other than this Note and shall have remained in default for thirty days or (B) default in the observance or performance of any other agreement or condition relating to any such indebtedness or contained in any instrument or agreement evidencing, securing or relating thereto, or any other event shall occur or condition exist, the effect of which default or other event or condition is to cause, or to permit the holder or holders of such indebtedness to cause, with the giving of notice if required, such Indebtedness to become due prior to its stated maturity;

(v) an action or proceeding shall be commenced in respect of Maker or any of its subsidiaries, without its application or consent, in any court of competent jurisdiction, seeking: (A) the liquidation, reorganization, moratorium, dissolution, winding up, or composition or readjustment of its debts; (B) the appointment of a trustee, receiver, custodian, liquidator or the like of it or of all or any substantial part of its assets in connection with the liquidation or dissolution of Maker or any of its subsidiaries; or (C) similar relief in respect of it under any law providing for the relief of debtors, and such proceeding or case described in clause (A), (B) or (C) herein shall continue undismissed, or unstayed and in effect, for a period of 30 days or any order for relief shall be entered in an involuntary case under United States Bankruptcy Code (as now or hereafter in effect) or under the comparable laws of any jurisdiction (foreign or domestic) against Maker or any of its Subsidiaries or action under the laws of any jurisdiction (foreign or domestic) analogous to any of the foregoing shall be taken with respect to Maker or any of its subsidiaries and shall continue undismissed, or unstayed and in effect for a period of 30 days; or

(vi) Maker grants a security interest (or similar concept under the Laws of any country) to any third party which gives such third party priority over Maker on any of its assets or personal property relative to Lender.

If at any time while this Note is outstanding, Maker directly or indirectly receives proceeds from any kind of financing transaction including through the issuance of any equity securities or indebtedness, Maker shall give written notice to Lender within one day, and Lender within 10 days after receipt of such written notice may request a prepayment of the principal and any other amounts payable hereunder in an amount up to 15% of the gross proceeds received by Maker from any such financing.

At any time Maker may prepay all or any portion of the principal amount of this Note and any other amounts payable hereunder without penalty.

At any time after the occurrence of any event of default, the indebtedness evidenced by this Note and/or any note(s) or other obligation(s) which may be taken in renewal, extension, substitution or modification of all or any part of the indebtedness evidenced thereby and all other obligations of Maker to Lender howsoever created and existing, which shall include all principal and any other amounts owing hereunder, shall immediately become due and payable without demand upon or notice to Maker, and Lender shall be entitled to exercise all remedies as provided by law and/or equity.

So long as any portion of this Note is outstanding, Maker will not directly or indirectly:

(i) enter into, create, incur, assume, guarantee or suffer to exist any indebtedness for borrowed money of any kind, other than (A) indebtedness evidenced by this Note, and (B) indebtedness incurred by Maker in the ordinary course of business, not to exceed $15,000 in the aggregate and which is subordinated in the right of payment to amounts payable to Maker pursuant to this Note on terms reasonably satisfactory to Maker;

(ii) enter into, create, incur, assume or suffer to exist any liens of any kind, on or with respect to any of its property or assets now owned or hereafter acquired or any interest therein or any income or profits therefrom, other than (A) liens created under this Note, (B) any lien for taxes not yet due or delinquent or being contested in good faith by appropriate proceedings for which adequate reserves have been established in accordance with United States generally accepted accounting principles, (C) any statutory lien arising in the ordinary course of business by operation of law with respect to a liability that is not yet due or delinquent, (D) any lien created by operation of law, such as materialmen’s liens, mechanics’ liens and other similar liens, arising in the ordinary course of business with respect to a liability that is not yet due or delinquent or that are being contested in good faith by appropriate proceedings;

(iii) amend its articles of incorporation, bylaws or other charter documents so as to adversely affect any rights of Lender, unless the sole and exclusive purpose of such amendment of the Maker’s articles of incorporation, bylaws or other charter documents is to increase the authorized capitalization of Lender;

(iv) repay, repurchase or offer to repay, repurchase or otherwise acquire more than a de minimis number of securities other than Lender subject to the prepayment provisions herein;

(v) pay cash dividends or distributions on any equity securities of Maker; or

(vi) enter into any agreement with respect to any of the foregoing.

Maker shall use the proceeds from the loan to which this Note relates solely for working capital and general corporate purposes. Maker shall continue to operate its business in the ordinary course in accordance with all applicable laws and shall not surrender or lose possession of (other than to Lender), sell, lease, rent or otherwise dispose of or transfer or encumber any of the Collateral or any right, title or interest therein, except for the sale of Inventory in the ordinary course of business consistent with past practice.

Upon the occurrence of a default or event of default under this Note and while any such default or event of default is continuing, Lender shall have and be entitled to, in addition to all other rights and remedies expressly granted to Lender in this Note, all rights and remedies of a secured party under the UCC and other applicable laws. Without limiting the generality of the foregoing, upon the occurrence and during the continuance of a default or event of default hereunder, Lender may sell, resell, lease, use, assign, license, sublicense, transfer or otherwise dispose of any or all of the Collateral in its then condition or following any commercially reasonable preparation or processing (utilizing in connection therewith any of Maker’s assets and personnel, without charge or liability to Lender therefor) at public or private sale, by one or more contracts, in one or more parcels, at the same or different times, for cash or credit, or for future delivery without assumption of any credit risk, all as Lender deems advisable; provided, however, that Maker shall be credited with the net proceeds of sale only when such proceeds are finally collected by Lender and after the obligations and liabilities of Maker hereunder owing to Lender shall have been satisfied therefrom. Lender shall have the right upon any such public sale, and, to the extent permitted by law, upon any such private sale, to purchase the whole or any part of the Collateral so sold, free of any right or equity of redemption, which right or equity of redemption the Grantor hereby releases, to the extent permitted by law. Maker hereby agrees that it will at its expense and upon request of Lender forthwith, assemble all or part of the Collateral as directed by Lender and make it available to Lender at a place to be designated by Lender that is reasonably convenient to both parties. Upon the occurrence and during the continuance of an event of default, Lender may (i) enter onto the property where any Collateral is located and take possession thereof with or without judicial process, (ii) prior to the disposition of the Collateral, store, process, repair or recondition the Collateral or otherwise prepare the Collateral for disposition in any manner to the extent Collateral Lender deems appropriate, (iii) take possession of Maker’s premises or place custodians in exclusive control thereof, remain on such premises and use the same and any of Maker’s equipment for the purpose of completing any work in process, taking any actions described in the preceding clause, and (iv) collecting any obligation or liability secured by the Collateral hereunder.

Maker hereby waives presentment for payment, demand, notice of dishonor and protest and agrees that (i) any collateral, lien or right of setoff securing any indebtedness evidenced by this Note may, from time to time, in whole or in part, be exchanged or released, and any person liable on or with respect to this Note may be released, all without notice to or further reservations of rights against Maker, any indorser, surety or guarantor and all without in any way affecting or releasing the liability of Maker, any indorser, surety or guarantor, and (ii) none of the terms or provisions hereof may be waived, altered, modified or amended except as Lender may consent thereto in writing.

Maker hereby agrees to pay all actual out-of-pocket costs and expenses, including reasonable attorneys’ fees, incurred by Lender in the collection of the indebtedness evidenced by this Note, in enforcing any of the rights, powers, remedies and privileges of Lender hereunder, or in connection with any further negotiations, modifications, releases, or otherwise incurred by Lender in connection with this Note and the enforcement of its rights hereunder. As used in this Note, the term “attorneys’ fees” shall mean reasonable actual out-of-pocket charges and expenses for legal services rendered to or on behalf of Lender in connection with the collection of the indebtedness evidenced by this Note at any time whether prior to the commencement of judicial proceedings and/or thereafter at the trial and/or appellate level and/or in pre-judgment and post-judgment or bankruptcy proceedings.

In no event shall the rate of interest charged under this Note as determined under applicable law exceed the rate that may legally be charged to Maker for obligations of this nature under the laws of the State of Nevada, and any interest that may be paid in excess of the legal limit shall, at the option of Lender, be refunded to Maker or shall be applied towards payment of the principal obligation under this Note.

All questions concerning the interpretation, construction, validity, and enforcement of this Note shall be governed by and construed and enforced in accordance with the internal laws of the state of Nevada, without regard to the principles of conflicts of law thereof. Each party agrees that all actions concerning the interpretation, construction, validity, and enforcement of the transactions contemplated by this Note (whether brought against a party hereto or its respective affiliates, directors, officers, shareholders, partners, members, employees or agents) shall be commenced exclusively in the state or federal courts located in Providence, Rhode Island. Each party hereby irrevocably submits to the exclusive jurisdiction of the state and federal courts sitting in Providence, Rhode Island for the adjudication of any dispute hereunder or in connection herewith or with any transaction contemplated hereby, and hereby irrevocably waives, and agrees not to assert in any action, any claim that it is not personally subject to the jurisdiction of any such court, that such action is improper or is an inconvenient venue for such action. Each party hereby irrevocably waives personal service of process and consents to process being served in any such action by mailing a copy thereof via registered or certified mail or overnight delivery (with evidence of delivery) to such party at the address in effect for notices to it under this Note and agrees that such service shall constitute good and sufficient service of process and notice thereof. Nothing contained herein shall be deemed to limit in any way any right to serve process in any other manner permitted by law. In any action, Maker and Lender hereby irrevocably waive any right it may have to, and agrees not to request, a jury trial for the adjudication of any dispute hereunder or in connection with or arising out of this Note or any transaction contemplated hereby. Each party hereto agrees that a final judgment in any such action, litigation, or proceeding shall be conclusive and may be enforced in other jurisdictions by suit on the judgment or in any other manner provided by law. Nothing herein shall affect any right that Lender may otherwise have to bring any action or proceeding relating to this Note against Maker or its properties in the courts of any jurisdiction.

To the extent that Lender receives any payment on account of any of Maker’s obligations or liabilities hereunder, and any such payment(s) or any part thereof are subsequently invalidated, declared to be fraudulent or preferential, set aside, subordinate and/or required to be repaid to a trustee, receiver or any other person or entity under any bankruptcy act, state or federal law, common law or equitable cause, then, to the extent of such payment(s) received, Maker’s obligations or liabilities hereunder or part thereof intended to be satisfied shall be revived and continue in full force and effect, as if such payment(s) had not been received by Lender and applied on account of Maker’s obligations and liabilities hereunder.

If any provisions of this Note shall be deemed unenforceable under applicable law, such provision shall be ineffective, but only to the extent of such unenforceability, without invalidating the remainder of such provision or the remaining provisions of this Note. All of the terms and provisions of this Note shall be applicable to and be binding upon each and every maker, indorser, surety, guarantor, all other persons who are or may become liable for the payment hereof and their heirs, personal representatives, successors or assigns.

All notices, approvals, requests, demands and other communications hereunder shall be delivered or made in the manner set forth in, and shall be effective in accordance with the terms of, the Debt Satisfaction Agreement. Maker or Lender may change their respective notice addresses by written notice given to each other party five days prior to the effectiveness of such change.

No failure on the part of Lender to exercise, and no delay in exercising, any right, remedy, power or privilege hereunder shall operate as a waiver thereof, nor shall any single or partial exercise of any such right, remedy, power or privilege preclude any other or further exercise thereof or the exercise of any other right, remedy, power or privilege. The rights and remedies under this Note are cumulative and not exclusive of any rights, remedies, powers and privileges that may otherwise be available to Lender.

Time is of the essence as to each provision of this Note which requires Maker to take any action within a specified time period.

MAKER AND LENDER (BY ACCEPTING THIS NOTE) HEREBY MUTUALLY WAIVE TRIAL BY JURY IN ANY ACTION, PROCEEDING OR COUNTERCLAIM BROUGHT BY EITHER MAKER OR LENDER AGAINST THE OTHER AND BASED UPON, ARISING OUT OF, OR IN CONNECTION WITH, THIS NOTE, OR OTHER DOCUMENTS SECURING OR EXECUTED IN CONNECTION WITH THIS NOTE.

All references to “$” herein shall refer to United States dollars.

[Signature page follows]

IN WITNESS WHEREOF, Maker has executed this Note as of July 25, 2025.

The Lender hereby agrees and accepts this Note as of July 25, 2025:

Exhibit 99.1

Beeline Completes Strategic Divestiture to Accelerate Digital Mortgage, Title, and Equity Product Expansion

Providence, Rhode Island—(Newsfile Corp. - July 29, 2025) - Beeline Holdings, Inc. (NASDAQ: BLNE) (“Beeline” or the “Company”), the fast-growing digital mortgage platform redefining the path to homeownership, today announced it has disposed of its majority ownership in Bridgetown Spirits Corp. (“Spirits”) in exchange for $367,404 pursuant to a Debt Satisfaction Agreement. As a result, Spirits is no longer a subsidiary of the Company. This asset was the last asset held as a result of its forward merger completed on October 7, 2024 with Beeline Financial Holdings, Inc. The move reaffirms Beeline’s focus on proptech, mortgage, alternative equity products and generating SAAS revenue while strengthening its balance sheet.

The transaction closed on Friday, July 25th in which the common stock of Spirits held by the Company was disposed of to a group led by the former CEO of the Company and the President of Spirits, Geoffrey Gwin. As part of the transaction, Beeline will write off certain related accounts payable it had assumed as part of the merger and eliminate the need to fund and account for Spirits. Beeline also funded a $75,000 one-year senior secured term loan to Spirits and in exchange received a secured promissory note in the principal amount of $100,000 from Spirits.

Said Chris Moe, CFO of Beeline, “Beeline continues to make moves designed to position itself to capitalize on its new products, an emerging platform and in a market that is expected to recover in 2026. We continue to see strong quarterly revenue growth outpacing the industry averages. We are now in a position to exclusively focus on our business and Bridgetown can move its business forward as a private company allowing itself to focus on its unique Oregon-themed brands.”

Geoffrey Gwin, commented, “I want to thank Chris Moe, CFO and Nick Liuzza, CEO for driving this transaction from the Beeline side. We view the transaction as a win for both sides. Our team is excited to dig in as the next chapter for the Bridgetown Spirits has officially started.”

Beeline expects to report its earnings for the second quarter on August 14, 2025. On July 16, 2025, Ladenberg Thalman & Co. Inc. initiated coverage of Beeline and issued a “Buy rating” with a $4.50 price target. The closing price on Monday, July 28, 2025, was $2.14.

Forward-Looking Statements

This press release contains forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995, including statements regarding the potential future growth prospects of Beeline’s business and trends in the mortgage industry generally. Forward-looking statements are prefaced by words such as “anticipate,” “expect,” “plan,” “could,” “may,” “will,” “should,” “would,” “intend,” “seem,” “potential,” “appear,” “continue,” “future,” believe,” “estimate,” “forecast,” “project,” and similar words. Forward-looking statements are based on our current expectations and assumptions regarding our business, the economy and other future conditions. Because forward-looking statements relate to the future, they are subject to inherent uncertainties, risks and changes in circumstances that are difficult to predict. We caution you, therefore, against relying on any of these forward-looking statements. Our actual results may differ materially from those contemplated by the forward-looking statements for a variety of reasons, including, without limitation, the possibility that estimates, projections and assumptions on which the forward-looking statements are based prove to be incorrect, the continued strength of the U.S. economy, changes in interest rates, the future of U.S. tariff policy, Beeline’s need for additional capital to meet its future goals and milestone targets, Beeline’s ability to attract homeowners to its products and services, the ability of Beeline and third parties on which it depends to comply with applicable regulatory requirements, the risk that software and technology infrastructure on which Beeline depends fail to perform as designed or intended, and the Risk Factors contained in our Form 10-K filed April 15, 2025 and other filings with the Securities and Exchange Commission. Any forward-looking statement made by us in this presentation speaks only as of the date on which it is made. Factors or events that could cause our actual results to differ may emerge from time to time, and it is not possible for us to predict all of them. We undertake no obligation to publicly update any forward-looking statement, whether as a result of new information, future developments or otherwise, except as may be required by law.

ir@makeabeeline.com