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TIPT 10-K & 10-Q changes, risk factors and insider trading

Tiptree Inc. · Nasdaq · Fire, Marine & Casualty Insurance · CIK 1393726 · All filings on SEC.gov

Everything below is quoted or computed from Tiptree Inc.'s public SEC filings. It is not a recommendation to buy or sell. Automated comparisons can contain errors; confirm with the original filing.

At a glance

36 / 47risk-factor paragraphs added / removed in latest 10-K
14new risk-factor headings
1Form 4 filings reporting open-market purchases (last 180 days)
0Form 4 filings reporting open-market sales (last 180 days)

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What changed in the latest 10-K

Comparing 10-K filed 2026-03-09 (period ending 2025-12-31) with 10-K filed 2025-03-03 (period ending 2024-12-31).

Risk Factors (10-K Item 1A)

36new paragraphs
47removed paragraphs
37reworded paragraphs
22,861 → 23,963words in section

New heading “Risks Related to the Sale”

New heading “The announcement and pendency of the Sale and the other transactions contemplated by the Sale Agreement, whether or not completed, creates uncertainty about our future, which could have a material adverse effect on our business, financial condition and results of operations, including the Retained Business.”

New heading “Tiptree will incur significant transaction costs in connection with the Sale.”

New heading “Tiptree will have broad discretion in the use of the proceeds from the Sale and may use proceeds in ways that stockholders may not approve.”

New heading “Any Leakage will decrease the proceeds that Tiptree will receive in the Sale, and if there is additional leakage, Tiptree may not receive its pro rata portion of the leakage reserve holdback amount.”

New heading “Tiptree does not expect to distribute cash to its stockholders in connection with the Sale, and any return to its stockholders is expected to come, if at all, only from potential increases in the price of Tiptree common stock.”

New heading “If the proposed Sale is not completed, we may explore other potential transactions, but alternatives may be less favorable to us.”

New heading “The failure to complete the Sale may impact our business, financial condition and results of operations.”

New heading “Even if the Sale is completed, we cannot provide any assurances that we will realize the financial benefits we currently anticipate from the Sale.”

New heading “After completion of the Sale, Tiptree’s future results of operations will be dependent solely on the Retained Business, Tiptree will have substantially fewer assets, Tiptree may be more susceptible to adverse events, and Tiptree may not be able to use the proceeds from the Sale as intended.”

New heading “After completion of the Sale, the continuing costs and burdens associated with being a public company will constitute a much larger percentage of Tiptree’s revenues.”

New heading “Maintenance of our Investment Company Act of 1940 exemption imposes limits on our operations.”

New heading “The opinion obtained by the Fortegra Board from Barclays and relied upon by the Tiptree Board does not and will not reflect changes in circumstances after the date of such opinion.”

New heading “Securities class action and derivative lawsuits may be brought against Tiptree in connection with the Sale, which could result in substantial costs and may delay or prevent the Sale from being completed.”

Removed heading “Some of our investments are made jointly with other persons or entities, which may limit our flexibility with respect to such jointly owned investments and could, thereby, have a material adverse effect on our business, results of operations and financial condition and our ability to sell these investments.”

Removed heading “Certain of our and our subsidiaries’ assets are subject to credit risk, market risk, interest rate risk, credit spread risk, call and redemption risk and refinancing risk, and any one of these risks may materially and adversely affect the value of our assets, our results of operations and our financial condition.”

Removed heading “Our holding company structure with multiple lines of business, may adversely impact the market price of our common stock and our ability to raise equity and debt capital.”

Removed heading “Maintenance of our 1940 Act exemption imposes limits on our operations.”

Removed heading “We could be materially adversely affected by violations of the U.S. Foreign Corrupt Practices Act, the U.K. Bribery Act and anti-corruption laws in other applicable jurisdictions.”

Removed heading “Assessments and premium surcharges for state guaranty funds, secondary-injury funds, residual market programs and other mandatory pooling arrangements may reduce our insurance subsidiaries’ profitability.”

Removed heading “Operation of dry bulk vessels and product tankers is subject to complex laws and regulations, including environmental laws and regulations that, if any of our vessel owner subsidiaries are found guilty of violation, can result in substantial fines and costs to the Company.”

Largest changes (selected automatically by length and topic keywords; quoted verbatim, no commentary)

Removed text topics: default, impairment, downgrade, interest rate
“Credit risk is the risk that the obligor will be unable to pay scheduled principal and/or interest payments. Defaults by third parties in the payment or performance of their obligations could reduce our income and realized gains or result in the recognition of losses. The fair value of our assets may be materially and adversely affected by increases in interest rates, downgrades in our direct investments and by other factors that may result in the recognition of other-than-temporary impairments. Each of these events may cause us to reduce the fair value of our assets.”
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New text topics: lawsuit, class action
“Securities class action and derivative lawsuits may be brought against Tiptree in connection with the Sale, which could result in substantial costs and may delay or prevent the Sale from being completed.”
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Removed text topics: fine, regulation
“Operation of dry bulk vessels and product tankers is subject to complex laws and regulations, including environmental laws and regulations that, if any of our vessel owner subsidiaries are found guilty of violation, can result in substantial fines and costs to the Company.”
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New text topics: lawsuit, class action, liquidity
“Securities class action lawsuits and derivative lawsuits are often brought against public companies that have entered into acquisition, merger or other business combination agreements that could prevent or delay the completion of the Sale and result in significant costs to Tiptree, including any costs associated with the indemnification of directors and officers. Even if such a lawsuit is without merit, defending against these claims can result in substantial costs and divert management time and resources. …”
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Removed text topics: litigation, ai, regulation
“Additionally, there are significant risks involved in developing and deploying AI, such as an increase in intellectual property infringement or misappropriation, data privacy, cybersecurity, operational and technological risks, harmful content, accuracy, bias, toxicity and discrimination, any of which could affect our insurance subsidiaries’ further development, adoption, and use of AI, and may cause them to incur additional research and development costs to resolve such issues. …”
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Removed text topics: interest rate
“Certain of our and our subsidiaries’ assets are subject to credit risk, market risk, interest rate risk, credit spread risk, call and redemption risk and refinancing risk, and any one of these risks may materially and adversely affect the value of our assets, our results of operations and our financial condition.”
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Full comparison: every changed paragraph (120)

Green = added, red = removed. Unchanged paragraphs and tables are not shown. Read the complete text in the original filing.

Added

Risks Related to the Sale

Added

The announcement and pendency of the Sale and the other transactions contemplated by the Sale Agreement, whether or not completed, creates uncertainty about our future, which could have a material adverse effect on our business, financial condition and results of operations, including the Retained Business.

Added

The announcement and pendency of the Sale and the other transactions contemplated by the Sale Agreement may adversely affect the trading price of Tiptree common stock, our business and our relationships with clients, customers and employees. Third parties may be unwilling to enter into material agreements with respect to our businesses that remain after the Sale (the “Retained Business”) or may seek to change existing business relationships. New or existing customers and business partners may prefer to enter into agreements with our competitors who have not expressed an intention to sell their business because customers and business partners may perceive that such new relationships are likely to be more stable. Additionally, employees working in the Retained Business may become concerned about the future of the Retained Business, as applicable, and lose focus or seek other employment. In addition, while the completion of the Sale is pending, we may be unable to attract and retain key personnel and our management’s focus and attention and employee resources may be diverted from operational matters. The occurrence of any of these events, individually or in combination, could have a material adverse effect on our business, financial condition and results of operations. Additionally, we have incurred substantial transaction costs and diversion of management resources in connection with the Sale, and we will continue to do so until the final closing or termination of the Sale.

Added

Tiptree will incur significant transaction costs in connection with the Sale.

Added

Tiptree has incurred and is expected to continue to incur a number of non-recurring costs associated with the Sale. These costs have been, and will continue to be, substantial and, in certain cases, will be borne by Tiptree whether or not the Sale is completed. A substantial majority of non-recurring expenses will consist of transaction costs and include, among others, fees paid to legal and financial advisors. Any litigation that may result from the announcement, pendency or completion of the Sale has the potential to impose additional substantial expenses on Tiptree. If the Sale is not completed, Tiptree will have incurred substantial expenses for which no ultimate benefit will have been received. Tiptree has incurred out-of-pocket expenses in connection with the Sale for legal and accounting fees and financial printing and other costs and expenses, much of which will be incurred even if the Sale is not completed. If the board of directors of Tiptree has determined in good faith (after consultation with its outside legal counsel and financial advisors) that an acquisition proposal constitutes a Superior Proposal (as defined in the Sale Agreement), then Tiptree may terminate the Sale Agreement to enter into an agreement with respect to such Superior Proposal, subject to compliance with the procedures specified in the Sale Agreement and payment of a termination fee of $49.5 million.

Added

Tiptree will have broad discretion in the use of the proceeds from the Sale and may use proceeds in ways that stockholders may not approve.

Added

Tiptree will have broad discretion in the use of the net proceeds it receives from the Sale and may use proceeds in ways that some stockholders may not approve. Tiptree intends to use proceeds from the Sale for working capital and general corporate purposes, including to pay transaction expenses, to pay taxes on the transactions contemplated by the Sale Agreement, to repay existing debt of Tiptree, to engage in opportunistic stock repurchases and/or pay dividends, to purchase additional assets or businesses and/or for any other purpose that the Tiptree Board deems appropriate. Because of the number and variability of factors that will determine our use of the net proceeds from the Sale, their ultimate use may vary substantially from their currently intended use.

Added

Tiptree management may not spend the net proceeds in ways that improve Tiptree’s results of operations or enhance the value of Tiptree common stock. The failure by Tiptree’s management to apply these funds effectively could result in financial losses that could have a material adverse effect on Tiptree’s business or cause the price of Tiptree common stock to decline. Tiptree management may invest the net proceeds from this offering in a manner that does not produce income or that loses value.

Added

Any Leakage will decrease the proceeds that Tiptree will receive in the Sale, and if there is additional leakage, Tiptree may not receive its pro rata portion of the leakage reserve holdback amount.

Added

Any Leakage, including any Transaction Expenses (as defined in the Sale Agreement) but excluding permitted leakage that occurs after June 30, 2025, and at or prior to the closing will decrease the Aggregate Closing Purchase Price (as defined in the Sale Agreement) and therefore the proceeds that Tiptree will receive in the Sale. Moreover, if, following the closing, it is determined that there was additional leakage, Tiptree may not receive its pro rata portion of the leakage reserve holdback amount. Because Leakage is defined to include payments, liabilities or obligations of or by Fortegra and its subsidiaries, the amount of any Leakage may be influenced by factors outside of Tiptree’s control.

Added

Tiptree does not expect to distribute cash to its stockholders in connection with the Sale, and any return to its stockholders is expected to come, if at all, only from potential increases in the price of Tiptree common stock.

Added

Tiptree does not expect to distribute cash to its stockholders in connection with the Sale. Tiptree has previously repurchased, and may from time to time repurchase, shares of Tiptree common stock and/or pay cash dividends. Factors that may impact our decisions regarding the method, timing and amount of a return of capital, if any, include economic and market conditions, our financial condition and operating results, cash requirements, capital requirements of our operating subsidiaries, legal requirements, regulatory constraints, investment opportunities at the time any such payment is considered, and other factors Tiptree deems relevant. Furthermore, the specific timing and amount of any dividend payments are subject to declaration on future dates by the Tiptree Board in its sole discretion. There can be no assurances that we will complete any return of capital to our stockholders.

Added

If the proposed Sale is not completed, we may explore other potential transactions, but alternatives may be less favorable to us.

Added

Completion of the Sale will require significant time, attention, and resources of our senior management and others within Tiptree, potentially diverting their attention from other business opportunities that might benefit us. If the proposed Sale is not completed, Tiptree may explore other strategic alternatives with another party or parties. An alternative transaction may have terms that are less favorable to us than the terms of the proposed Sale, or we may be unable to reach agreement with any third-party on an alternate transaction that we would consider to be reasonable. Any future “transfer of assets” of Tiptree or other similar transaction may be subject to further stockholder approval, and there is no guarantee that Tiptree would be able to obtain such stockholder approval in favor of any such sale or other transaction.

Added

The failure to complete the Sale may impact our business, financial condition and results of operations.

Added

If the Sale is not completed for any reason, Tiptree’s business, financial condition and results of operations may be impacted. To the extent that the market price of Tiptree common stock reflects positive market assumptions that the Sale will be completed and the related benefits will be realized, the failure to complete the Sale may result in a decrease in the market value of Tiptree common stock and may impair Tiptree’s ability to achieve its objective of enhancing the value of its assets to Tiptree stockholders.

Added

Even if the Sale is completed, we cannot provide any assurances that we will realize the financial benefits we currently anticipate from the Sale.

Added

We cannot provide any assurances that we will realize the financial benefits we currently anticipate from the Sale. Any failure to realize the financial benefits we currently anticipate from the Sale could have a material adverse impact on our future operating results and financial condition and could materially and adversely affect the trading price or trading volume of Tiptree common stock. Our results of operations currently are not, and may not be in the future even if the Sale and the other transactions contemplated by the Sale Agreement are consummated, sufficient to service our indebtedness and to fund our other expenditures, and we may not be able to obtain financing to meet these requirements. Even if the Sale and the other transactions contemplated by the Sale Agreement are consummated, if we experience a default under Tiptree’s existing credit agreement or instruments governing our future indebtedness, our business, financial condition and results of operations may be adversely impacted.

Added

Tiptree also expects to recognize significant taxable gain upon completion of the Sale, which reflects expected treatment of the proposed Sale as a taxable sale of Fortegra common stock by Tiptree for U.S. federal income tax purposes.

Added

After completion of the Sale, Tiptree’s future results of operations will be dependent solely on the Retained Business, Tiptree will have substantially fewer assets, Tiptree may be more susceptible to adverse events, and Tiptree may not be able to use the proceeds from the Sale as intended.

Added

If the Sale is completed, Tiptree will no longer hold any Fortegra shares or have any interest in the future earnings or growth of Fortegra, and Tiptree’s future results of operations will be dependent solely on the Retained Business and differ materially from Tiptree’s previous results of operations. After completion of the Sale, Tiptree will be subject to concentration of the risks that affect our Retained Business and Tiptree will have substantially fewer assets and may experience significant decreases in earnings and cash flow and increases in operating costs or other expenses. Following the Sale, Tiptree will continue to be a public company with ongoing costs associated with public company operations, which will be a greater percentage of our revenues. The market price of Tiptree common stock may significantly decrease, and Tiptree common stock may be more susceptible to market fluctuations. In addition, if there are significant adverse changes in Tiptree’s business prospects, the industries in which Tiptree operates, or in market and economic conditions generally, Tiptree may not be able to use the proceeds from the Sale as currently intended because the proceeds may be required for operations or other needs that we do not currently anticipate. Any downturn in the Retained Business or future prospects following the closing of the Sale, or if Tiptree fails to bring overhead costs in line with our reduced operations following the closing of the Sale, could have a material adverse effect on Tiptree’s future operating results and financial condition and could materially and adversely affect the market price of Tiptree’s securities.

Added

After completion of the Sale, the continuing costs and burdens associated with being a public company will constitute a much larger percentage of Tiptree’s revenues.

Added

If the Sale is completed, Tiptree will remain a public company and will continue to be subject to the listing standards of the Nasdaq and SEC rules and regulations. While all public companies face the costs and burdens associated with being public companies, the costs and burden of being a public company will be a significant portion of Tiptree’s revenues, which will be reduced if the Sale is completed.

Added

Maintenance of our Investment Company Act of 1940 exemption imposes limits on our operations.

Added

We conduct our operations so that we are not required to register as an investment company under the Investment Company Act of 1940. Therefore, we must limit the types and nature of businesses in which we engage and assets that we acquire. We monitor our compliance with the Investment Company Act of 1940 on an ongoing basis and may be compelled to take or refrain from taking actions, to acquire additional income or loss generating assets or to forgo opportunities that might otherwise be beneficial or advisable, including, but not limited to selling assets that are considered to be investment securities or forgoing the sale of assets that are not investment securities, in order to ensure that we (or a subsidiary) may continue to rely on the applicable exceptions or exemptions. These limitations on our freedom of action could have a material adverse effect on our financial condition and results of operations.

Added

If we fail to maintain an exemption, exception or other exclusion from registration as an investment company, we could, among other things, be required to substantially change the manner in which we conduct our operations either to avoid being required to register as an investment company or to register as an investment company. Under the Investment Company Act of 1940, a company may be deemed to be an investment company if it owns investment securities with a value exceeding 40% of the value of its total assets (excluding government securities and cash items) on an unconsolidated basis, unless an exemption or safe harbor applies. We refer to this test as the “40% Test.” Securities issued by companies other than consolidated companies are generally considered “investment securities” for purposes of the Investment Company Act of 1940, unless other circumstances exist which actively involve the company holding such interests in the management of the underlying company.

Added

We currently maintain our exemption through the 40% test. Upon the completion of the Sale, we intend to invest in government securities, cash and other investments excluded from the 40% Test, but, may no longer be able to comply with the 40% Test. In that case, we would rely on a safe harbor exemption from the Investment Company Act of 1940 for so-called “transient investment companies.” Consistent with the “transient investment company” safe harbor, we will have to reduce our holdings of “investment securities to not more than 40% of our total assets as soon as is reasonably possible and in any event within one year from the earlier of (i) the date on which we own securities and/or cash having a value exceeding 50% of the value of our company’s total assets on either a consolidated or unconsolidated basis or (ii) the date on which we own or propose to acquire “investment securities” having a value exceeding 40% of the value of our company’s total assets (exclusive of U.S. government securities and cash items) on an unconsolidated basis.

Added

If we were required to register as an investment company under the Investment Company Act of 1940, we would become subject to substantial regulation with respect to, among other things, our capital structure (including our ability to use leverage), management, operations, transactions with affiliated persons (as defined in the Investment Company Act of 1940), portfolio composition, including restrictions with respect to diversification and industry concentration, and our financial condition and results of operations may be adversely affected. If we did not register despite being required to do so, criminal and civil actions could be brought against us, our contracts would be unenforceable unless a court were to require enforcement, and a court could appoint a receiver to take control of us and liquidate our business.

Added

The opinion obtained by the Fortegra Board from Barclays and relied upon by the Tiptree Board does not and will not reflect changes in circumstances after the date of such opinion.

Added

On September 24, 2025, Barclays Capital Inc. (“Barclays”) rendered its oral opinion (which was subsequently confirmed in writing) to the Fortegra Board that, as of the date of its written opinion and based upon and subject to the qualifications, limitations, assumptions and other matters stated in its opinion, the aggregate consideration of $1.65 billion in cash in the Sale is fair, from a financial point of view, to holders of Fortegra common stock. Changes in the operations and prospects of Fortegra, including financial forecasts relating to Fortegra, general market and economic conditions and other factors, many of which may be beyond Tiptree’s control, and on which the opinion of Barclays was based, may alter Fortegra’s value and affect the conclusions reached in the opinion. Fortegra has not obtained, and does not expect to request, an updated opinion from Barclays. Barclays’ opinion does not speak to the time when the Sale will be completed or to any date other than the date of such opinion. As a result, the opinion does not and will not address the fairness, from a financial point of view, of the consideration to be received by holders of Fortegra common stock in connection with the Sale at the time the Sale is completed or at any time other than the time the opinion was rendered.

Added

Securities class action and derivative lawsuits may be brought against Tiptree in connection with the Sale, which could result in substantial costs and may delay or prevent the Sale from being completed.

Added

Securities class action lawsuits and derivative lawsuits are often brought against public companies that have entered into acquisition, merger or other business combination agreements that could prevent or delay the completion of the Sale and result in significant costs to Tiptree, including any costs associated with the indemnification of directors and officers. Even if such a lawsuit is without merit, defending against these claims can result in substantial costs and divert management time and resources. An adverse judgment could result in monetary damages, which could have a negative impact on Tiptree’s liquidity and financial condition.

Added

Lawsuits that may be brought against Tiptree or Tiptree’s directors could also seek, among other things, injunctive relief or other equitable relief, including a request to enjoin Tiptree from consummating the Sale. It is a condition to the completion of the Sale that no temporary restraining order, preliminary or permanent injunction or other judgment or order, injunction, ruling, decision, assessment, award, administrative order, judicial decision or decree entered or issued by, or in agreement with, any governmental authority to which Fortegra or any of its Subsidiaries is a party or to which it is subject, issued by a court of competent jurisdiction that prevents the consummation of the transactions contemplated by the Sale Agreement has been issued and remains in effect, and no statute, rule, regulation or other law has been enacted, enforced or promulgated by any governmental authority which would restrain, enjoin or otherwise prohibit the consummation of the transactions contemplated by the Sale Agreement Consequently, if a plaintiff is successful in obtaining an injunction prohibiting completion of the Sale, that injunction may delay or prevent the Sale from being completed within the expected timeframe or at all, which may adversely affect Tiptree’s business, financial position and results of operation.

Reworded

Our assets include equity securities, real estate, non-controlling interests in credit assets and related equity interests which may be illiquid or have limited liquidity. It may be difficult for us to dispose of assets with limited liquidity rapidly, or at favorable prices, if at all. In addition, assets with limited liquidity may be more difficult to value and may be sold at a substantial discount or experience more volatility than more liquid assets. We may not be able to dispose of assets at the carrying value reflected in our financial statements. Our results of operations and cash flows may be materially and adversely affected if our determinations regarding the fair value of our illiquid assets are materially higher than the values ultimately realized upon their disposal.

Removed

•an increase in capital raising by companies in the industry, which could result in new entrants to the insurance markets and an excess of capital in the industry; and

Reworded

•an increase in capital raising by companies in the industry, which could result in new entrants to the insurance markets and an excess of capital in the industry; and the deregulation of commercial insurance lines in certain states and the possibility of federal regulatory reform of the insurance industry, which could increase competition from standard carriers.

Reworded

•our ability to realize the full extent of the benefits, synergies or cost savings that we expect to realize as a result of the completion and integration of an acquisition within the anticipated time frame, or at all;

Reworded

•receipt of necessary consents, clearances and approvals in connection with the acquisition;

Reworded

•diversion of management’s attention from other strategies and objectives;

Removed

•motivating, recruiting and retaining executives and key employees; and

Reworded

•motivating, recruiting and retaining executives and key employees; and conforming and integrating financial reporting, standards, controls, procedures and policies, business cultures and compensation structures.

Reworded

•if our insurance subsidiaries change their business practices from their organizational business plan in a manner that no longer supports A.M. Best’s or KBRA’s ratings; if unfavorable financial, regulatory or market trends affect our insurance subsidiaries, including excess market capacity; if our insurance subsidiaries’ losses exceed their loss reserves; if our insurance subsidiaries have unresolved issues with government regulators;

Removed

•if unfavorable financial, regulatory or market trends affect our insurance subsidiaries, including excess market capacity;

Removed

•if our insurance subsidiaries’ losses exceed their loss reserves;

Removed

•if our insurance subsidiaries have unresolved issues with government regulators;

Removed

•if our insurance subsidiaries are unable to retain their senior management or other key personnel;

Removed

•if our insurance subsidiaries’ investment portfolio incurs significant losses; or

Reworded

•if our insurance subsidiaries are unable to retain their senior management or other key personnel; if our insurance subsidiaries’ investment portfolio incurs significant losses; or if A.M. Best or KBRA alters its capital adequacy assessment methodology in a manner that would adversely affect our insurance subsidiaries’ ratings.

Reworded

•causing our insurance subsidiaries’ current and future distribution partners and insureds to choose other, more highly-rated competitors; increasing the cost or reducing the availability of reinsurance to our insurance subsidiaries; or severely limiting or preventing our insurance subsidiaries from writing new and renewal insurance contracts.

Removed

•increasing the cost or reducing the availability of reinsurance to our insurance subsidiaries; or

Removed

•severely limiting or preventing our insurance subsidiaries from writing new and renewal insurance contracts.

Reworded

Our insurance subsidiaries use reinsurance to reduce the severity and incidence of claims costs, and to provide relief with regard to certain reserves. Under these reinsurance arrangements, other insurers assume a portion of our losses and related expenses; however, we remain liable as the direct insurer on all risks reinsured. Consequently, reinsurance arrangements do not eliminate our obligation to pay claims and we assume credit risk with respect to our ability to recover amounts due from reinsurers. The inability or unwillingness of any reinsurer to meet its financial obligations could negatively affect our business, results of operations, financial condition and cash flows. As credit risk is generally a function of the economy, our insurance subsidiaries face a greater credit risk in an economic downturn. While our insurance subsidiaries attempt to manage credit risks through underwriting guidelines, collateral requirements and other oversight mechanisms, their efforts may not be successful. For example, to reduce such credit risk, our insurance subsidiaries require certain third parties to post collateral for some or all of their obligations to them. In cases where our insurance subsidiaries receive letters of credit from banks as collateral and one of their counterparties is unable to honor its obligations, our insurance subsidiaries are exposed to the credit risk of the banks that issued the letters of credit.

Added

While our insurance subsidiaries attempt to manage credit risks through underwriting guidelines, collateral requirements and other oversight mechanisms, their efforts may not be successful. For example, to reduce such credit risk, our insurance subsidiaries require certain third parties to post collateral for some or all of their obligations to them. In cases where our insurance subsidiaries receive letters of credit from banks as collateral and one of their counterparties is unable to honor its obligations, our insurance subsidiaries are exposed to the credit risk of the banks that issued the letters of credit.

Reworded

Our insurance subsidiaries use various modeling techniques, including Stochastic, Bayesian statistics, classification, regression, clustering and other advanced machine learning techniques along with data analytics to analyze and estimate loss trends and other risks associated with their underwriting and claims operations. Our insurance subsidiaries use the modeled outputs and related analyses to assist them in certain decisions involving underwriting, pricing, claims, reserving, reinsurance, and catastrophe risk. As with many technological innovations, AI and machine learning present risks and challenges that could affect their adoption, and therefore our insurance subsidiaries’ business. The assumptions used in deriving modeled outputs and related analyses are subject to uncertainties, model errors and the limitations of historical internal and industry data. In addition, the modeled outputs and related analyses may from time to time contain inaccuracies, which could have a material adverse effect on our insurance subsidiaries’ results of operations, if, based upon these models, they misprice their products, underestimate the frequency and/or severity of loss events, or overestimate the risks they are exposed to. Persistent inaccuracies may adversely impact new business growth and retention of our insurance subsidiaries’ existing clients which could have a material adverse effect on our insurance subsidiaries’ results of operations and financial condition.

Removed

Additionally, there are significant risks involved in developing and deploying AI, such as an increase in intellectual property infringement or misappropriation, data privacy, cybersecurity, operational and technological risks, harmful content, accuracy, bias, toxicity and discrimination, any of which could affect our insurance subsidiaries’ further development, adoption, and use of AI, and may cause them to incur additional research and development costs to resolve such issues. In addition, no assurance can be provided that the usage of such AI will enhance our insurance subsidiaries’ business or assist in being more efficient or profitable. The introduction of AI technologies into new or existing products may result in new or enhanced governmental or regulatory scrutiny, litigation, confidentiality or security risks, ethical concerns, or other complications that could adversely affect our insurance subsidiaries’ results of operations and financial condition. It is not possible to predict all of the risks related to the use of AI, and changes in laws, rules, directives and regulations governing AI may adversely affect our insurance subsidiaries’ ability to develop and use AI or subject them to legal liability.

Reworded

•pledge Fortegra common stock;

Reworded

•incur or guarantee additional debt;

Reworded

•incur liens;

Reworded

•make negative pledges;

Reworded

•make junior payments;

Showing the first 60 of 120 changed paragraphs. The complete comparison will be part of Pro (coming soon). Meanwhile you can read the full text in the original filing.

Management's Discussion & Analysis (MD&A) (10-K Item 7)

Heads-up: the two versions of this section differ a lot in length (12,813 vs 4,634 words). That can mean the company reorganized its report or that our automatic section detection picked up the wrong boundaries. Please check the original filings before relying on this comparison.
57new paragraphs
209removed paragraphs
16reworded paragraphs
12,813 → 4,634words in section

New heading “Summary of Consolidated Results”

New heading “Non Operating Income”

New heading “Income before taxes”

New heading “Net Income (Loss) from continuing operations”

New heading “Net Income (Loss) from discontinued operations”

New heading “HELD FOR SALE AND DISCONTINUED OPERATIONS:”

New heading “Cash Flows from Discontinued Operations”

New heading “Fair Value Measurement”

Removed heading “Selected Key Metrics”

Removed heading “Net Income (Loss) Attributable to common stockholders”

Removed heading “Adjusted net income & Adjusted return on average equity - Non-GAAP”

Removed heading “Results by Segment”

Removed heading “Components of our Results of Operations”

Removed heading “Key Performance Metrics”

Removed heading “Combined Ratio, Loss Ratio, Acquisition Ratio, Underwriting Ratio and Operating Expense Ratio”

Removed heading “Non-GAAP Financial Measures”

Removed heading “Underwriting and Fee Revenues and Underwriting and Fee Margin”

Removed heading “Results of Operations - Year Ended December 31, 2024 compared to 2023”

Removed heading “Revenues - Year Ended December 31, 2024 compared to 2023”

Removed heading “Expenses - Year Ended December 31, 2024 compared to 2023”

Removed heading “Gross Written Premiums and Premium Equivalents(1)”

Removed heading “Net written premiums”

Removed heading “Underwriting and Fee Revenues and Margin - Non-GAAP”

Removed heading “Return on Average Equity”

Removed heading “Adjusted Net Income and Adjusted Return on Average Equity - Non-GAAP”

Removed heading “Components of our Results of Operations”

Removed heading “Results of Operations”

Removed heading “Revenues - Year Ended December 31, 2024 compared to 2023”

Removed heading “Expenses - Year Ended December 31, 2024 compared to 2023”

Removed heading “Income (loss) before taxes”

Removed heading “Tiptree Capital - Other”

Removed heading “Results of Operations”

Removed heading “Income (loss) before taxes”

Removed heading “Adjusted net income - Non-GAAP(1)”

Removed heading “Non-GAAP Reconciliations”

Removed heading “Underwriting and Fee Revenues and Underwriting and Fee Margin — Non-GAAP (Insurance only)”

Removed heading “Adjusted Net Income — Non-GAAP”

Removed heading “Adjusted Return on Average Equity — Non-GAAP”

Removed heading “Goodwill and Intangible Assets, net”

Removed heading “Deferred Acquisition Costs”

Removed heading “Earned Premiums, net”

Removed heading “Service and Administrative Fees”

Largest changes (selected automatically by length and topic keywords; quoted verbatim, no commentary)

Removed text topics: default, interest rate
“Net Realized and Unrealized Gains (Losses) include gains on sale of mortgage loans and the fair value adjustment in mortgage servicing rights. Gains on the sale of mortgage loans represent the difference between the selling price and carrying value of loans sold and are recognized upon settlement. Such gains also include the changes in fair value of loans held for sale and loan-related hedges and derivatives. …”
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Removed text topics: liquidity, inflation, interest rate
“Our results of operations are affected by a variety of factors including, but not limited to, general economic conditions and GDP growth, market liquidity and volatility, consumer confidence, U.S. demographics, employment and wage growth, business confidence and investment, inflation, interest rates and spreads, the impact of the regulatory environment, and the other factors set forth in Part I, Item 1A in our Annual Report on Form 10-K. Generally, our businesses are positively affected by a healthy U.S. …”
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Removed text topics: impairment, liquidity
“Net Realized and Unrealized Gains (Losses) on investments are a function of the difference between the amount received by us on the sale of a security and the security’s cost-basis, as well as any “other-than-temporary” impairments and allowances for credit losses which are recognized in earnings. In addition, equity securities and certain other investments are carried at fair value with unrealized gains and losses included in this line. …”
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Removed text topics: goodwill
“Goodwill and Intangible Assets, net”
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Removed text topics: impairment, goodwill
“The initial measurement of goodwill and intangibles requires judgment concerning estimates of the fair value of the acquired assets and liabilities. Goodwill and indefinite-lived intangible assets are not amortized but subject to tests for impairment annually or if events or circumstances indicate it is more likely than not they may be impaired. Finite-lived intangible assets are subject to impairment if events or circumstances indicate a possible inability to realize the carrying amount. …”
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Removed text topics: inflation, interest rate
“Insurance results primarily depend on pricing, underwriting, risk retention and the accuracy of reserves, reinsurance arrangements, returns on invested assets, and policy and contract renewals and run-off. Factors affecting these items, including conditions in financial markets, the global economy and the markets in which we operate, fluctuations in exchange rates, interest rates and inflation, including the current period of inflationary pressures, may have a material adverse effect on our results of operations or financial condition. …”
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Full comparison: every changed paragraph (282)

Green = added, red = removed. Unchanged paragraphs and tables are not shown. Read the complete text in the original filing.

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•Overview

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•Results of Operations

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•Non-GAAP Measures and Reconciliations

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•Liquidity and Capital Resources

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•Critical Accounting Policies and Estimates

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Tiptree allocates capital to select small and middle market companies with the mission of building long-term value. Established in 2007, we have a significant track record investing in the insurance sector and across a variety of other industries, including mortgage, specialty finance and shipping. Our largest operating subsidiary, Fortegra, is a leading provider of specialty insurance products and related services. We also generate earnings from a diverse group of select investments that we refer to as Tiptree Capital, which includes our Mortgage segment and other, non-insurance businesses and assets. We evaluate performance primarily by the comparison of stockholders’ long-term total return on capital, as measured by growth in stock price plus dividends paid, in addition to Adjusted Net Income.

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Our 2024 highlights include:

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Overall:

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•Tiptree reported net income of $53.4 million for the year ended December 31, 2024, compared to $14.0 million in the prior year period, driven by growth in insurance operations. Return on average equity was 12.2%, compared to 3.4% in 2023.

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•Adjusted net income of $100.1 million increased from $61.9 million in 2023, driven by growth in insurance operations. Adjusted return on average equity was 22.9%, as compared to 15.2% in 2023.

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•Gross written premiums and premium equivalents were $3.1 billion for the year ended December 31, 2024, an increase of $320.3 million, or 11.7%, from the prior year period as a result of growth in E&S insurance lines in the U.S. and Europe.

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•Net written premiums were $1.4 billion for the year ended December 31, 2024, an increase of 9.0%, driven by growth in gross written premiums and increased retention on Fortegra’s whole account quota share reinsurance arrangement from 30% to 40%, effective April 1, 2023.

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•Total revenues were $2.0 billion, an increase of $380.6 million, or 23.9%, from 2023, driven by premium growth in specialty E&S and admitted insurance lines in the U.S. and Europe.

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•Combined ratio of 90.0%, driven by consistent underwriting performance and the scalability of Fortegra’s operating platform.

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•Income before taxes of $183.2 million as compared to $129.8 million in 2023. Return on average equity was 26.0% in 2024 as compared to 25.7% in 2023, with the increases driven by growth in underwriting and fee revenues.

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•Adjusted net income (before NCI) was $157.0 million, an increase of $41.3 million, or 35.7%, from 2023. Adjusted return on average equity was 29.1%, as compared to 29.2% in 2023.

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•Fortegra’s total stockholders’ equity was $625.5 million as of December 31, 2024, compared to $452.6 million as of December 31, 2023, with the increase driven by growth in retained earnings and the aggregate capital contribution from Tiptree, Warburg, and Fortegra independent directors of $40.0 million during 2024.

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Tiptree Capital:

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•Mortgage income before taxes was $4.7 million for the year ended December 31, 2024, as compared to loss of $3.3 million in 2023, with the increase driven by the positive fair value adjustments in mortgage servicing rights, higher origination volumes and loan servicing fees.

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Key Trends:

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Our results of operations are affected by a variety of factors including, but not limited to, general economic conditions and GDP growth, market liquidity and volatility, consumer confidence, U.S. demographics, employment and wage growth, business confidence and investment, inflation, interest rates and spreads, the impact of the regulatory environment, and the other factors set forth in Part I, Item 1A in our Annual Report on Form 10-K. Generally, our businesses are positively affected by a healthy U.S. consumer, stable to gradually rising interest rates, stable markets and business conditions, and global growth and trade flows. Conversely, rising unemployment, volatile markets, rapidly rising interest rates, inflation, changing regulatory requirements and slowing business conditions can have a material adverse effect on our results of operations or financial condition.

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Insurance results primarily depend on pricing, underwriting, risk retention and the accuracy of reserves, reinsurance arrangements, returns on invested assets, and policy and contract renewals and run-off. Factors affecting these items, including conditions in financial markets, the global economy and the markets in which we operate, fluctuations in exchange rates, interest rates and inflation, including the current period of inflationary pressures, may have a material adverse effect on our results of operations or financial condition. Fortegra designs, markets and underwrites specialty property and casualty insurance products for select target markets or niches. The business has historically generated significant fee-based revenues by incorporating value-add coverages and services. Underwriting risk is mitigated through a combination of reinsurance and sliding scale commission structures with agents, distribution partners and/or third-party reinsurers. To mitigate counterparty risk, Fortegra ensures its reinsurance receivables are placed with highly rated and appropriately capitalized counterparties or with our distribution partners’ captive insurance vehicles which are collateralized with highly liquid investments, cash or letters of credit. While Fortegra’s insurance operations have historically maintained a relatively stable combined ratio, initiatives to change the business mix along with these economic factors could generate different results than the business has historically experienced. In particular, inflation can have an impact on replacement costs associated with claims from our customers to the extent we are unable to pass the higher costs of claims through higher premiums. In addition, fluctuations of the U.S. dollar relative to other currencies, including the British pound and Euro, would have an impact on book value between periods.

Removed

Fortegra’s investment portfolio includes fixed maturity securities, loans, credit investment funds, and equity securities. Many of those investments are held at fair value. From 2021 to 2024, the U.S. fixed income markets experienced a significant rise in interest rates. Rising interest rates have and could continue to impact the value of Fortegra’s fixed maturity securities, with any unrealized losses recorded in equity, and if realized, could impact our results of operations. Offsetting the impact of a rising interest rate environment, new investments in fixed rate instruments from both maturities and portfolio growth have and could continue to result in higher net interest income on investments. The weighted average duration of our fixed income available for sale securities is less than three years. While our asset and liability mix is relatively matched, should we need to liquidate any of these investments before maturity to pay claims, any realized losses could materially negatively impact our results of operations. Changes in fair value for loans, credit investment funds, and equity securities in Fortegra’s investment portfolio are reported as unrealized gains or losses in revenues and can be impacted by changes in interest rates, credit risk, currency risk, or market risk, including specific company or industry factors. In addition, our equity holdings are relatively concentrated. General equity market trends, along with company and industry specific factors, can impact the fair value which can result in unrealized gains and losses affecting our results.

Removed

Elevated 10-year treasury yields, and the tapering of the Federal Reserve’s purchases of mortgage-backed securities, has resulted in substantial increases in mortgage interest rates. Low mortgage interest rates driven by the Federal Reserve intervention in mortgage markets, and rising home prices in certain markets, provided tailwinds to the mortgage markets in 2020 and 2021, which benefited our mortgage operations and margins. The substantial rise in rates resulted in a sharp reversal of those trends, with volumes and margins declining significantly. Only partially offsetting the declines in mortgage originations is an increase in the fair value of our mortgage servicing portfolio as rising rates slow prepayment speeds, with a resulting increase in servicing income. Continued elevated mortgage rates could have a negative impact on our mortgage operations, and is likely to be only partially mitigated by the improvement in mortgage servicing revenues. A sustained period of negative profitability in the mortgage industry could also impact the availability of funding sources for our mortgage business.

Removed

Rising interest rates can also impact the cost of floating interest rate debt obligations, while declining rates can decrease the cost of debt. Our secured revolving and term credit agreements, preferred trust securities and asset based revolving financing are all floating rate obligations.

Added

Non-GAAP Measures and Reconciliations

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Liquidity and Capital Resources

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Critical Accounting Policies and Estimates

Added

OVERVIEW

Added

Our 2025 key highlights include:

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On September 26, 2025, Tiptree entered into the Sale Agreement with Purchaser and Fortegra whereby Tiptree and Warburg will sell Fortegra to Purchaser for aggregate consideration of $1.65 billion in cash (subject to certain adjustments set forth in the Sale Agreement). As of December 31, 2025, Tiptree owns approximately 69.1% of Fortegra on a fully diluted basis. At the closing of the Sale, Purchaser will acquire complete common equity ownership of Fortegra and all of its subsidiaries. Due to the pending transaction, Fortegra is classified as held for sale and presented in discontinued operations on Tiptree’s financial statements at December 31, 2025. This pending transaction has had no impact on Tiptree’s financial statements at December 31, 2025 other than incurred transaction expenses of approximately $14.5 million for the year ended December 31, 2025. If the transaction had been completed as of December 31, 2025, Tiptree would have reflected the below:

Added

On October 31, 2025, Tiptree entered into the Reliance Purchase Agreement with Reliance Buyer and Reliance whereby Tiptree will sell all of the issued and outstanding shares of common stock of Reliance to Reliance Buyer for aggregate consideration of 93.5% of Reliance’s tangible book value, or an estimated $50 million of gross proceeds and an after-tax loss impairment recorded of $10.7 million as of December 31, 2025 (subject to certain adjustments set forth in the Reliance Purchase Agreement).

Reworded

The following is a summary of our consolidated financial results for the years ended December 31, 2025, 2024 and 2023. In addition to GAAP results, management uses the Non-GAAP measures Adjusted net income, Adjusted return on average equity andmeasure book value per share as measurementsmeasurement of operating performance. Management believes thesethis measuresmeasure provideprovides supplemental information useful to investors as theyit areis frequently used by the financial community to analyze financial performance and comparison among companies. The Company reclassified income and expenses attributable to Fortegra and Reliance to net income (loss) from discontinued operations for the years ended December 31, 2025, 2024 and 2023. Assets and liabilities attributable to Fortegra and Reliance have been reclassified to assets held for sale and liabilities held for sale, respectively, as of December 31, 2025 and 2024.

Added

Summary of Consolidated Results

Removed

Adjusted Net Income and Adjusted Return on Average Equity. Adjusted net income is defined as income before taxes, less provision (benefit) for income taxes, and excluding the after-tax impact of various expenses that we consider to be unique and non-recurring in nature, including merger and acquisition related expenses, stock-based compensation, net realized and unrealized gains (losses) and intangibles amortization associated with purchase accounting, all of which is reduced for non-controlling interests. The calculation of adjusted net income excludes net realized and unrealized gains (losses) that relate to investments or assets rather than business operations. Adjusted net income is presented before the impacts of non-controlling interests. Adjusted return on average equity represents adjusted net income expressed on an annualized basis as a percentage of average beginning and ending stockholders’ equity during the period. Management uses adjusted net income and adjusted return on average equity as part of its capital allocation process and to assess comparative returns on invested capital. We believe adjusted net income provides additional clarity on the results of the Company’s underlying business operations as a whole for the periods presented by excluding distortions created by the unpredictability and volatility of realized and unrealized gains (losses). We also believe adjusted net income provides useful supplemental information to investors as it is frequently used by the financial community to analyze financial performance between periods and for comparison among companies.

Removed

Adjusted net income and adjusted return on average equity are not measurements of financial performance or liquidity under GAAP and should not be considered as an alternative or substitute for GAAP net income. See “Non-GAAP Reconciliations” for a reconciliation of these measures to their GAAP equivalents.

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Selected Key Metrics

Reworded

(1) See “—Non-GAAP Reconciliations” for a discussion of non-GAAP financial measures. Adjusted net income is presented after the impacts of non-controlling interests.

Added

Revenues

Reworded

For the year ended December 31, 2024,2025, revenues were $2.0$0.5 billion,million, which increaseddecreased $393.8$1.0 million, or 23.9%,67.9%, compared to the prior year period. The changes were primarilyyear, driven by growtha decrease in earnedvessels premiums, net and service and administrative fees, higher investment income, net realized and unrealized gains, and an increase in other income, including interest income on cash equivalents, compared to the prior year period.revenue.

Added

For the year ended December 31, 2024, revenues were $1.5 million, which decreased $0.6 million, or 28.2%, compared to the prior year, driven by a decrease in vessels revenue.

Added

Total expenses include employee compensation and benefits, public company and other expenses. Employee compensation and benefits include the expense of management, legal and accounting staff. Other expenses primarily consisted of audit and professional fees, insurance, office rent, expenses for the run-off of our shipping operations and other related expenses.

Added

For the year ended December 31, 2025, expenses were $47.2 million, which increased $5.4 million, or 13.0%, compared to the prior year. Employee compensation and benefits, included incentive compensation expense which related to the performance of the Company’s continuing and discontinued operations. For the year ended December 31, 2025, employee compensation and benefits were $33.8 million compared to $29.2 million for the prior year, driven by the increase in accrued incentive compensation expense and one-time expenses associated with reduction in workforce. Of the incentive compensation expense in 2025, $6.7 million was stock-based compensation expense, compared to $8.7 million in 2024. Other expenses were $11.9 million, compared to $11.2 million in the prior year, driven by increased professional fees and run-off expenses associated with our shipping investments.

Added

For the year ended December 31, 2024, expenses were $41.8 million, which decreased $3.8 million, or 8.3%, compared to the prior year. For the year ended December 31, 2024, employee compensation and benefits were $29.2 million compared to $30.7 million, driven by a decrease in accrued cash incentive compensation expense. Of the incentive compensation expense in 2024, $8.7 million was stock-based compensation expense, compared to $6.3 million in 2023. Other expenses were $11.2 million, compared to $13.5 million in the prior year, driven primarily by decreased professional fees.

Added

Non Operating Income

Added

For the year ended December 31, 2025, net realized and unrealized losses were $1.5 million, which increased $0.6 million, as compared to the losses of $0.9 million in the prior year, driven by the change in fair value of certain equity and other investments carried at fair value. For the year ended December 31, 2024, net realized and unrealized losses were $0.9 million, which decreased $4.4 million, as compared to the losses of $5.3 million in the prior year, driven by the change in fair value of certain equity and other investments carried at fair value. For the year ended December 31, 2025, other income was $3.6 million, as compared to $2.6 million in the prior year, with the increase driven by higher interest income on cash and cash equivalents recorded in other income. For the year ended December 31, 2024, other income was $2.6 million, as compared to $5.3 million in the prior year, with the decrease driven by lower interest income on cash and cash equivalents recorded in other income.

Added

Income before taxes

Removed

The table below provides a break down between net realized and unrealized gains and losses from Invesque and other securities which impacted our consolidated results on a pre-tax basis. Many investments are carried at fair value and marked to market through unrealized gains and losses. As a result, we expect earnings related to these investments to be relatively volatile between periods. Fixed income securities are primarily marked to market through AOCI in stockholders’ equity and do not impact net realized and unrealized gains and losses until they are sold.

Removed

(1) Excludes Invesque, Maritime transportation and Mortgage realized and unrealized gains and losses.

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Net Income (Loss) Attributable to common stockholders

Removed

For the year ended December 31, 2024, the net income attributable to common stockholders was $53.4 million, compared to $14.0 million in the prior year period, driven by growth in insurance underwriting and fee income and growth in net investment income and net realized and unrealized gains on the investment portfolio.

Removed

Adjusted net income & Adjusted return on average equity - Non-GAAP

Reworded

Adjusted net income forFor the year ended December 31, 20242025, wasthe $100.1Company reported a pre-tax loss of $44.6 million, anas increasecompared to a loss of $38.1$38.6 million,million or 61.6%, fromin the yearprior endedyear, December 31, 2023,primarily driven by growthincreased inoperating our insurance operations.expenses. For the year ended December 31, 2024, adjustedthe returnCompany onreported averagea equitypre-tax wasloss 22.9%,of $38.6, as compared to 15.2%a forloss of $43.5 million in the yearprior endedyear, December 31, 2023,primarily driven by thedecreased increaseoperating in adjusted net income.expenses.

Added

Net Income (Loss) from continuing operations

Added

For the year ended December 31, 2025, the Company reported a net loss from continuing operations of $38.9 million, compared to a net loss of $32.3 million in the prior year, primarily driven by increased operating expenses. For the year ended December 31, 2024, the Company reported a net loss from continuing operations $32.3 million, compared to a net loss of $38.7 million in the prior year, primarily driven by decreased operating expenses.

Added

Net Income (Loss) from discontinued operations

Added

For the year ended December 31, 2025, the Company reported a net income from discontinued operations of $73.8 million, compared to a net income of $85.7 million in the prior year, with the decrease driven by the after-tax loss on disposal of Reliance. For the year ended December 31, 2024, the Company reported a net income from discontinued operations of $85.7 million, compared to a net income of $52.7 million, with the increase driven by underwriting and fee income growth at Fortegra.

Removed

Total stockholders’ equity was $656.8 million as of December 31, 2024 compared to $576.6 million as of December 31, 2023, with the increase driven by comprehensive income, partially offset by net changes in non-controlling interests and dividends paid. In the year ended December 31, 2024, Tiptree returned $18.3 million to common stockholders through dividends paid.

Reworded

Total stockholders’ equity was $752.4 million as of December 31, 2025 compared to $656.8 million as of December 31, 2024, with the increase driven by comprehensive income in 2025, partially offset by preferred dividends paid at Fortegra and common dividends paid by Tiptree. In 2025, Tiptree returned $9.1 million to common stockholders through dividends paid. Book value per share for the period ended December 31, 20242025 was $12.29,$13.45, ana 9.4% increase from book value per share of $11.34$12.29 as of December 31, 2023,2024, driven by comprehensive income per share, partially offset by dividends paid of $0.49$0.24 per share, net changes in non-controlling interests and preferred dividends paid at Fortegra.

Added

Total stockholders’ equity was $656.8 million as of December 31, 2024 compared to $576.6 million as of December 31, 2023, with the increase driven by comprehensive income, partially offset by net changes in non-controlling interests and dividends paid. In the year ended December 31, 2024, Tiptree returned $18.3 million to common stockholders through dividends paid. Book value per share for the period ended December 31, 2024 was $12.29, an increase from book value per share of $11.34 as of December 31, 2023, driven by comprehensive income per share, partially offset by dividends paid of $0.49 per share, net changes in non-controlling interests and preferred dividends paid at Fortegra.

Showing the first 60 of 282 changed paragraphs. The complete comparison will be part of Pro (coming soon). Meanwhile you can read the full text in the original filing.

What changed in the latest 10-Q

Comparing 10-Q filed 2026-07-29 (period ending 2026-06-30) with 10-Q filed 2026-04-30 (period ending 2026-03-31).

Risk Factors (10-Q Part II, Item 1A)

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The section in the latest 10-Q reads in full:

For information regarding factors that could affect the Company, results of operations and financial condition, see the risk factors discussed under Part I, Item 1A in Tiptree’s Annual Report on Form 10-K for the fiscal year ended December 31, 2025. There have been no material changes in those risk factors.

Full comparison: every changed paragraph (1)

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Reworded

For information regarding factors that could affect ourthe Company, results of operations and financial condition, see the risk factors discussed under Part I, Item 1A in ourTiptree’s Annual Report on Form 10-K for the fiscal year ended December 31, 2025. There have been no material changes in those risk factors.

Management's Discussion & Analysis (MD&A) (10-Q Part I, Item 2)

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26reworded paragraphs
2,887 → 3,432words in section

Largest changes (selected automatically by length and topic keywords; quoted verbatim, no commentary)

New text topics: impairment, goodwill
“On May 1, 2026, the Company completed the Reliance Transaction, its mortgage segment, to Carrington Mortgage Services, LLC. Total consideration from the transaction consisted of cash proceeds of $49.7 million, subject to customary post-closing adjustments. The disposal group incurred cumulative impairment losses of $9.1 million upon its initial classification as held for sale and as a discontinued operation in 2025 which was inclusive of a goodwill and intangible impairment of $1.7 million. …”
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New text topics: impairment, goodwill
“On May 1, 2026, the Company completed the Reliance Transaction, its mortgage segment, to Carrington Mortgage Services, LLC. Total consideration from the transaction consisted of cash proceeds of $49.7 million, subject to customary post-closing adjustments. The disposal group incurred cumulative impairment losses of $9.1 million upon its initial classification as held for sale and as a discontinued operation in 2025 which was inclusive of a goodwill and intangible impairment of $1.7 million. …”
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Reworded topics: impairment

Paragraph as it now reads, with added and removed wording marked:

The revenues were $15.9 million forFor the three months ended MarchJune 31,30, 2026, comparedrevenues from Reliance were $5.5 million, reflecting only one month of operating results prior to $15.2the million in 2025, an increasesale of 4.8%.the Tiptreebusiness on May 1, 2026. The Company reported a net incomeloss of $0.9$0.5 million from Reliance in discontinued operations forduring the period. For the three months ended MarchJune 31,30, 2026,2025, comparedrevenues tofrom Reliance were $16.2 million. The Company reported a net lossincome of $0.1$0.2 million from Reliance in 2025,discontinued driven by higher impairment expense.operations.
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Removed text topics: covenant
“On February 7, 2025, we entered into the Tiptree Credit Agreement, pursuant to which Tiptree Holdings borrowed $75.0 million to, among other things, fund working capital and general corporate purposes. The principal of, and all accrued and unpaid interest on, all credit agreements under the Tiptree Credit Agreement will mature on February 7, 2028. A covenant of the credit agreement requires full repayment from the proceeds of the sale of Fortegra.”
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Reworded

Paragraph as it now reads, with added and removed wording marked:

Cash usedprovided inby discontinued operating activities was $9.8$53.2 million, comparedand to cash used in operating activities of $21.0$1.6 million for the threesix months ended MarchJune 31,30, 2026 and 2025, respectively. TheCash provided by discontinued investing activities was $696.3 million, and $73.0 million for the six months ended June 30, 2026 and 2025, respectively, primarily related to the Fortegra and Reliance dispositions. Investing activities related to the Fortegra sale included deal proceeds of $1.12 billion, reduced by $402.7 million of cash held at Fortegra and expected escrow-related amounts, resulting in net proceeds of $713.4 million. Investing activities related to the Reliance sale included deal proceeds of $46.9 million, reduced by $14.6 million of cash held at Reliance and expected escrow-related amounts, resulting in net proceeds of $29.9 million. Cash provided by discontinued financing activities was $42.2 million for the six months ended June 30, 2026, compared with cash used in investingdiscontinued activities was $38.6 million, compared to cash used in investingfinancing activities of $6.2$10.2 million for the threesix months ended MarchJune 31, 2026 and 2025, respectively. The cash provided by financing activities was $24.0 million, for the three months ended March 31, 2026. The cash used in financing activities was $5.8 million for the three months ended March 31,30, 2025.
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Reworded

Paragraph as it now reads, with added and removed wording marked:

For the three months ended MarchJune 31,30, 2026, expenses were $9.0$9.1 million, which decreased $4.0$2.9 million, or 30.6%,24.3%, compared to the prior year. For the six months ended June 30, 2026, expenses were $18.0 million, which decreased $6.9 million, or 27.6%, compared to the prior year. For the three and six months ended MarchJune 31,30, 2026, employee compensation and benefits were $6.8$6.5 million and $13.3 million, compared to $9.3$7.0 million forand $16.3 million, in the respective prior year,year periods. The declines were driven by lower incentive compensation and payroll expense associated with the reduction in workforce. Employee compensation and benefits included incentive compensation expense accruals related to the performance of the Company’s continuing and discontinued operations. OfFor the six months ended June 30, 2026 and 2025, incentive compensation expense inincluded 2026, $1.5$2.9 million wasand $8.4 million of stock-based compensationcompensation, expense, compared to $2.3 million in 2025.respectively. Other expenses were $1.9$2.2 million,million and $4.1 million for the three and six months ended June 30, 2026, respectively, compared to $3.3$4.6 million inand $7.9 million for the priorcorresponding year,periods in 2025, primarily driven by declines in professional fees.
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Full comparison: every changed paragraph (48)

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Reworded

Our Management’s Discussion and Analysis of Financial Condition and Results of Operations are presented in this section as follows:

Added

On May 29, 2026, the Company completed the sale of Fortegra, its insurance segment, pursuant to the Sale Agreement entered on September 26, 2025. The total consideration received for the sale of Fortegra consisted of cash proceeds of $1.65 billion, less transaction expenses of $25.0 million in which the Company received consideration of $1.12 billion. The Company recognized an after-tax gain on the sale of $372.2 million, which is included in net income from discontinued operations for the three and six months ended June 30, 2026.

Added

On May 1, 2026, the Company completed the Reliance Transaction, its mortgage segment, to Carrington Mortgage Services, LLC. Total consideration from the transaction consisted of cash proceeds of $49.7 million, subject to customary post-closing adjustments. The disposal group incurred cumulative impairment losses of $9.1 million upon its initial classification as held for sale and as a discontinued operation in 2025 which was inclusive of a goodwill and intangible impairment of $1.7 million. During the six months ended June 30, 2026, the Company recognized a favorable adjustment of $0.5 million in discontinued operations related to subsequent changes in estimated fair value less costs to sell, resulting in a cumulative pre-tax loss of $8.6 million.

Added

Prior to the sales, the assets and liabilities of Fortegra and Reliance were classified as held for sale as of December 31, 2025. Upon completion of the transactions in the three months ended June 30, 2026, the Company transferred control of the respective subsidiaries to the buyers and derecognized the related assets and liabilities from its condensed consolidated balance sheet.

Removed

On September 26, 2025, Tiptree entered into the Sale Agreement with Purchaser and Fortegra whereby Tiptree and Warburg will sell Fortegra to Purchaser for aggregate consideration of $1.65 billion in cash (subject to certain adjustments set forth in the Sale Agreement). As of March 31, 2026, Tiptree owns approximately 69.0% of Fortegra on a fully diluted basis. At the closing of the Sale, Purchaser will acquire complete common equity ownership of Fortegra and all of its subsidiaries. Due to the pending transaction, Fortegra is classified as held for sale and presented in discontinued operations on Tiptree’s financial statements at March 31, 2026. If the transaction had been completed as of March 31, 2026, Tiptree would have reflected the below:

Removed

On October 31, 2025, Tiptree entered into the Reliance Purchase Agreement with Reliance Buyer and Reliance whereby Tiptree will sell all of the issued and outstanding shares of common stock of Reliance to Reliance Buyer for aggregate consideration of 93.5% of Reliance’s tangible book value, or an estimated $50.0 million of gross proceeds as of March 31, 2026 (subject to certain adjustments set forth in the Reliance Purchase Agreement).

Reworded

The following is a summary of ourTiptree’s consolidated financial results for the three and six months ended MarchJune 31,30, 2026 and 2025. In addition to GAAP results, management uses the Non-GAAP measure book value per share as a measurement of operating performance. Management believes this measure provides supplemental information useful to investors as it is frequently used by the financial community to analyze financial performance and comparison among companies. The Company has reclassified income and expenses attributable to Fortegra and Reliance to net income (loss) from discontinued operations for the three and six months ended MarchJune 31,30, 2026 and 2025. Assets and liabilities attributable to Fortegra and Reliance have been reclassified to assets held for sale and liabilities held for sale, respectively, as of March 31, 2026 and 2025.

Reworded

See Note (3) Dispositions, Assets Held for SaleDispositions & Discontinued Operations for further details.

Reworded

WeThe Company did not generate operating revenues from continuing operations during the three months ended MarchJune 31,30, 2026, compared to $0.4$0.1 million in the prior year, driven by lower other revenue. The Company did not generate operating revenues from continuing operations during the six months ended June 30, 2026, compared to $0.5 million in the prior year, driven by lower other revenue. Interest income from the Company’s cash and cash equivalents and marketable securities was recorded in other income within non-operatingnon operating income.

Reworded

Total expenses include employee compensation and benefits, public company expenses and other expenses. Employee compensation and benefits include the expense of management, legal, and accounting staff. Other expenses primarily consisted of audit and professional fees, insurance, office rent, expenses for the run-off of our shipping operations and other related expenses.

Reworded

For the three months ended MarchJune 31,30, 2026, expenses were $9.0$9.1 million, which decreased $4.0$2.9 million, or 30.6%,24.3%, compared to the prior year. For the six months ended June 30, 2026, expenses were $18.0 million, which decreased $6.9 million, or 27.6%, compared to the prior year. For the three and six months ended MarchJune 31,30, 2026, employee compensation and benefits were $6.8$6.5 million and $13.3 million, compared to $9.3$7.0 million forand $16.3 million, in the respective prior year,year periods. The declines were driven by lower incentive compensation and payroll expense associated with the reduction in workforce. Employee compensation and benefits included incentive compensation expense accruals related to the performance of the Company’s continuing and discontinued operations. OfFor the six months ended June 30, 2026 and 2025, incentive compensation expense inincluded 2026, $1.5$2.9 million wasand $8.4 million of stock-based compensationcompensation, expense, compared to $2.3 million in 2025.respectively. Other expenses were $1.9$2.2 million,million and $4.1 million for the three and six months ended June 30, 2026, respectively, compared to $3.3$4.6 million inand $7.9 million for the priorcorresponding year,periods in 2025, primarily driven by declines in professional fees.

Reworded

For the three months ended MarchJune 31,30, 2026, there were no net realized and unrealized lossesgains wereor $0.3 million,losses, as compared to the gainslosses of $0.7$1.5 million in the prior year, driven by the change in fair value of certain equity and other investments carried at fair value. For the three months ended MarchJune 31,30, 2026, other income was $1.0$3.9 million, as compared to $0.5$0.9 million in the prior year.year, primarily driven by higher interest income earned on U.S. Treasury securities held within cash and cash equivalents and marketable securities.

Added

For the six months ended June 30, 2026, net realized and unrealized losses were $0.3 million, as compared to the losses of $0.7 million in the prior year, driven by the change in fair value of certain equity and other investments carried at fair value. For the six months ended June 30, 2026, other income was $4.9 million, as compared to $1.4 million in the prior year, primarily driven by higher interest income earned on U.S. Treasury securities held within cash and cash equivalents and marketable securities.

Reworded

For the three and six months ended MarchJune 31,30, 2026, the Company reported a pre-tax loss of $8.3$5.1 million and $13.4 million, asrespectively, compared to a pre-tax loss of $11.3$12.5 million and $23.8 million, in the corresponding prior year,year withperiods. theThe periodimprovement overin periodboth changeperiods primarilywas driven by lower operating expenses.expenses and higher other income.

Reworded

For the three and six months ended MarchJune 31,30, 2026, the Company reported a net loss from continuing operations of $7.1$6.4 million and $13.6 million, respectively, compared to a net loss of $9.7$10.4 million and $20.1 million, in the corresponding prior year,year withperiods. theThe periodimprovement overin periodboth changeperiods primarilywas driven by lower operating expenses.expenses and higher other income.

Reworded

For the three and six months ended MarchJune 31,30, 2026, the Company reported a net income from discontinued operations of $21.4$395.7 million and $417.1 million, respectively, compared to net income of $15.3$29.4 million and $44.7 million, in the corresponding prior year,year drivenperiods. byThe higherincrease Fortegrain earnings.both periods was primarily attributable to the gain recognized on sale on Fortegra.

Reworded

Total stockholders’ equity was $750.5$907.1 million as of MarchJune 31,30, 2026 compared to $683.5$723.4 million as of MarchJune 31,30, 2025, with the increase driven by comprehensive income over the past twelve months, including the gain on sale of Fortegra, partially offset by share repurchases, preferred dividends paid at Fortegra,repurchases and common dividends paid by Tiptree.dividends. In the threesix months ended MarchJune 31,30, 2026, Tiptreethe Company returned $2.3$4.5 million to common stockholders through dividends paid and $5.0$10.3 million through share repurchases.

Reworded

Book value per share for the period ended MarchJune 31,30, 2026 was $13.42,$24.34, a 6.2%82.6% increase from book value per share of $12.63$13.33 as of MarchJune 31,30, 2025, primarily driven by comprehensive income per share, including the gain recognized on Fortegra transaction, partially offset by dividends paid of $0.06$0.12 per share, net changes in non-controlling interests and preferred dividends paid at Fortegra.

Reworded

HELD FOR SALEDISPOSITIONS AND DISCONTINUED OPERATIONS

Added

In connection with the sale of Fortegra and Reliance, the results of operations for these businesses are presented as discontinued operations in the condensed consolidated statements of operations for all periods presented. The results of discontinued operations include the operating results of Fortegra and Reliance through their respective disposal dates in the three months ended June 30, 2026 and the gain (loss) recognized upon disposition. See Note (3) Dispositions & Discontinued Operations for detailed financial information on each business sold. Following the completion of the sales in the three months ended June 30, 2026, the assets and liabilities associated with Fortegra and Reliance were derecognized and are no longer reflected on the Company’s condensed consolidated balance sheet as of June 30, 2026.

Added

On May 29, 2026, the Company completed the sale of Fortegra, its insurance segment, pursuant to the Sale Agreement entered on September 26, 2025. The total consideration received for the sale of Fortegra consisted of cash proceeds of $1.65 billion, less transaction expenses of $25.0 million in which the Company received consideration of $1.12 billion for its percentage ownership of the business. The Company recognized an after-tax gain on the sale of $372.2 million, which is included in net income from discontinued operations for the three and six months ended June 30, 2026.

Added

For the three months ended June 30, 2026, revenues from Fortegra were $341.6 million, reflecting two months of operating results prior to the sale of the business on May 29, 2026. For the three months ended June 30, 2026, the Company reported net income of $396.2 million from Fortegra in discontinued operations during the period, including $372.2 million after-tax gain on sale. For the three months ended June 30, 2025, revenues from Fortegra were $513.0 million. The Company reported income before taxes of $64.9 million and net income of $29.2 million from Fortegra in discontinued operations during the period.

Added

For the six months ended June 30, 2026, revenues from Fortegra were $820.0 million, reflecting five months of operating results prior to the sale of the business on May 29, 2026. For the six months ended June 30, 2026, the Company reported net income of $416.7 million from Fortegra in discontinued operations during the period, including $372.2 million net gain on sale. For the six months ended June 30, 2025, revenues from Fortegra were $993.6 million. The Company reported income before taxes of $101.8 million and net income of $44.7 million from Fortegra in discontinued operations during the period.

Removed

During 2025, Tiptree entered into two sale transactions that have been classified as discontinued operations within its consolidated financial statements. See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations for detailed financial information on each business sold.

Removed

On September 26, 2025, Tiptree entered into the Sale Agreement with Purchaser and Fortegra whereby Tiptree and Warburg will sell Fortegra to Purchaser for aggregate consideration of $1.65 billion in cash (subject to certain adjustments set forth in the Sale Agreement). As of March 31, 2026, Tiptree owns approximately 69.0% of Fortegra on a fully diluted basis. At the closing of the Sale, Purchaser will acquire complete common equity ownership of Fortegra and all of its subsidiaries. As a result of this agreement, and subsequent shareholder approval, Fortegra is now classified as held for sale and in discontinued operations on Tiptree’s financial statements as of March 31, 2026. The anticipated closing date, subject to customary regulatory approvals, is expected in mid-2026.

Removed

Total gross written premiums and premium equivalents for the three months ended March 31, 2026 were $761.1 million, compared to $753.2 million in 2025, an increase of 1.1% driven by growth in specialty E&S insurance lines. Net written premiums were $354.3 million for the three months ended March 31, 2026, compared to $357.7 million in 2025, a decrease of 0.9%. Tiptree reported net income of $20.5 million from Fortegra in discontinued operations for the three months ended March 31, 2026, compared to $15.5 million in 2025. Fortegra’s combined ratio for the three months ended March 31, 2026 was 87.0%, compared to 89.9% in 2025, down 2.9 percentage points, reflecting the consistent underwriting performance and scalability of Fortegra’s operations.

Removed

The total gross written premiums and premium equivalents of $761.1 million and $753.2 million for the three months ended March 31, 2026 and 2025, respectively, were comprised of gross written premiums of $643.0 million and $538.7 million, plus assumed premiums of $66.7 million and $127.9 million, plus gross service and administrative fee additions of $51.4 million and $86.6 million, respectively.

Added

On May 1, 2026, the Company completed the Reliance Transaction, its mortgage segment, to Carrington Mortgage Services, LLC. Total consideration from the transaction consisted of cash proceeds of $49.7 million, subject to customary post-closing adjustments. The disposal group incurred cumulative impairment losses of $9.1 million upon its initial classification as held for sale and as a discontinued operation in 2025 which was inclusive of a goodwill and intangible impairment of $1.7 million. During the six months ended June 30, 2026, the Company recognized a favorable adjustment of $0.5 million in discontinued operations related to subsequent changes in estimated fair value less costs to sell, resulting in a cumulative pre-tax loss of $8.6 million. Transaction costs associated with the sale were $2.8 million and are also included in discontinued operations for the three and six months ended June 30, 2026.

Removed

On October 31, 2025, Tiptree entered into the Reliance Purchase Agreement with Reliance Buyer and Reliance whereby Tiptree will sell Reliance to Reliance Buyer for aggregate consideration of 93.5% of Reliance’s tangible book value, or an estimated $50 million of gross proceeds as of March 31, 2026 (subject to certain adjustments set forth in the Reliance Purchase Agreement). As a result of this agreement, Reliance is now classified as held for sale and in discontinued operations on Tiptree’s financial statements as of March 31, 2026. The anticipated closing date, subject to customary regulatory approvals, is expected in the first half of 2026.

Reworded

The revenues were $15.9 million forFor the three months ended MarchJune 31,30, 2026, comparedrevenues from Reliance were $5.5 million, reflecting only one month of operating results prior to $15.2the million in 2025, an increasesale of 4.8%.the Tiptreebusiness on May 1, 2026. The Company reported a net incomeloss of $0.9$0.5 million from Reliance in discontinued operations forduring the period. For the three months ended MarchJune 31,30, 2026,2025, comparedrevenues tofrom Reliance were $16.2 million. The Company reported a net lossincome of $0.1$0.2 million from Reliance in 2025,discontinued driven by higher impairment expense.operations.

Added

For the six months ended June 30, 2026, revenues from Reliance were $21.4 million, reflecting four months of operating results prior to the sale of the business on May 1, 2026. The Company reported net income of $0.3 million from Reliance in discontinued operations during the period. For the six months ended June 30, 2025, revenues from Reliance were $31.4 million. The Company reported net income of $0.1 million from Reliance in discontinued operations.

Reworded

The income tax expense of $1.3 million and benefit $2.0 million from continuing operations of $1.2 million and $1.6 million for the three months ended MarchJune 31,30, 2026 and 2025, respectively, was reflected as components of net income (loss) from continuing operations. For the three months ended MarchJune 31,30, 2026 and 2025, the Company’s effective tax rate related to pre-tax income from continuing operations was equal to 13.9%(25.6)% and 14.2%,16.2%, respectively, with both lower than the U.S. statutory income tax rate of 21.0%, primarily due to the impacts of nontaxable and nondeductible items.

Added

The income tax expense of $0.2 million and benefit $3.6 million from continuing operations for the six months ended June 30, 2026 and 2025, respectively, was reflected as components of net income (loss) from continuing operations. For the six months ended June 30, 2026 and 2025, the Company’s effective tax rate related to pre-tax income from continuing operations was equal to (1.2)% and 15.2%, respectively, with both lower than the U.S. statutory income tax rate of 21.0%, primarily due to the impacts of nontaxable and nondeductible items.

Reworded

Tiptree signed agreements to sellsold its insurance and mortgage subsidiaries andduring the three months ended June 30, 2026. It had previously recorded deferred taxes on the outside basis on those investments which representsrepresented the tax that would be due, before consideration of loss carryforwards, when Tiptree sellssold its shares in these subsidiaries at their carrying values on Tiptree’s condensed consolidated balance sheet. AsThe ofbalance Marchjust 31,prior 2026,to the deferred tax liability relating to these investments, which remains on Tiptree’s balance since it is a parent-level tax attribute,sales was $122.0$130.0 million, an increase of $4.1$12.2 million from the year ended December 31, 2025, of which $3.5$1.8 million of benefit was recorded in OCI, and $7.6$14.0 million of expense was recorded as a provision for income taxes in discontinued operations. As of MarchJune 31,30, 2025,2026, the deferred tax liability relating to these investments washas $91.8been million,brought anto increasezero and a current tax payable of $7.1$204.8 million fromhas been established through the year ended December 31, 2024, of which $2.3 million of expense was recorded in OCI, and $4.7 million of expense was recorded as a provision for income taxes in discontinued operations.

Added

Tiptree’s total assets were 1.13 billion as of June 30, 2026, compared to 6.84 billion as of December 31, 2025. The decrease was primarily driven by the derecognition of the assets previously classified as held for sale in connection with the completed sales of Fortegra and Reliance during the three months ended June 30, 2026.

Removed

Tiptree’s total assets were $7.0 billion as of March 31, 2026, compared to $6.8 billion as of December 31, 2025. Tiptree's assets from continuing operations were $52.7 million and $71.7 million as of March 31, 2026 and December 31, 2025, respectively, a decrease of $18.9 million, driven by sales of marketable securities. Assets held for sale were $6.9 billion and $6.8 billion as of March 31, 2026 and December 31, 2025, respectively, an increase of $146.5 million, primarily driven by growth in Fortegra.

Removed

As of March 31, 2026, Tiptree had approximately $146.1 million in gross capital and operating loss carryforwards, primarily driven by the sale of 14.05 million shares of Invesque in 2024 for $0.5 million of proceeds.

Reworded

Total stockholders’ equity was $750.5$907.1 million as of MarchJune 31,30, 2026, compared to $752.4 million as of December 31, 2025, with the decreaseincrease primarily driven by comprehensive income forover the threepast monthssix endedmonths, Marchincluding 31,the 2026,gain on sale on Fortegra, offset by Fortegradividends preferred dividends, Tiptree common dividendspaid and share repurchases. As of MarchJune 31,30, 2026, there were 37,567,02437,266,005 shares of common stock outstanding as compared to 37,824,472 shares as of December 31, 2025, with the decrease driven by share repurchases.

Reworded

OurThe Company’s principal sources of liquidity are unrestricted cash, cash equivalents and other liquid investments, the Tiptree Credit Agreement and distributions from operating subsidiaries, including income generated from ourthe Company’s investment portfolio and salesproceeds from the sale of assets, investments and operatingother businesses.assets. WeThe intend to use ourCompany’s cash resources toare continueintended to fund ourcorporate operations, growpursue ourcapital businessesallocation opportunities and pursuereturn newcapital acquisitionto opportunities.shareholders, Weas appropriate. Management may seek additional sources of cash to fund acquisitions or investments. These additional sources of cash may take the form of debt or equity and may be at the parent, subsidiary or asset level. WeTiptree areis a holding company, and ourthe Company's liquidity needs are primarily for compensation, professional fees, office rent and insurance costs.

Reworded

As of MarchJune 31,30, 2026, cash and cash equivalents were $33.4$946.9 million, compared to $30.8 million as of December 31, 2025, an increase of $2.6$916.1 million.million, primarily reflecting the net proceeds received from the completed sales of Fortegra and Reliance. In addition, the Company held marketable securities of $0.6$158.2 million as of MarchJune 31,30, 2026, compared to $21.7 million in December 31, 2025, withas thea decreaseportion driven byof the sale ofproceeds equitieswere andinvested in U.S. Treasury securities.securities with a maturity date greater than 90 days at purchase. As of June 30, 2026, the Company had a current tax payable of $204.8 million primarily related to the Fortegra sale. The majority is expected to be paid prior to September 30, 2026.

Reworded

WeManagement believebelieves that cash and cash equivalents, marketable securities, and cash flow from operations and the proceeds of the Sale and Purchase Agreement will provide sufficient capital to continue to grow the businessbusiness, and pay down the outstanding debt,cover capital expenditures and other general corporate needs over the next several years. As wemanagement continuecontinues to expand ourTiptree’s business, including by any acquisitions wethe Company may make in the future, additional working capital for increased costs could be required.

Removed

On February 7, 2025, we entered into the Tiptree Credit Agreement, pursuant to which Tiptree Holdings borrowed $75.0 million to, among other things, fund working capital and general corporate purposes. The principal of, and all accrued and unpaid interest on, all credit agreements under the Tiptree Credit Agreement will mature on February 7, 2028. A covenant of the credit agreement requires full repayment from the proceeds of the sale of Fortegra.

Reworded

Refer to the Consolidated Statement of Cash Flow and Note (3) Dispositions, Assets Held for SaleDispositions & Discontinued Operations for additional details on cash flows related to discontinued operations.

Reworded

Cash used in operating activities for continuing operations for the threesix months ended MarchJune 31,30, 2026 and 2025 was $8.3$18.4 million and $12.3$13.7 million, respectively. This reflects the use of funds to support centralized management and ongoing corporate-level operating requirements.

Reworded

Investing activities from continuing operationsFor the threesix months ended MarchJune 31,30, 2026, generated net cash of $20.9, primarily due to proceeds from sales2026 and maturities of investments exceeding purchased of investments. For the three months ended March 31, 20252025, cash used in investing activities was $11.9$136.3 millionmillion, and $62.9 million, respectively, driven by purchases of investments outpacing the proceeds from sales and maturities of investments.

Reworded

Cash used in financing activities was $8.0$89.7 million for the threesix months ended MarchJune 31,30, 2026, primarily attributable to the principal paydown of borrowings at the holding company, repurchases of common stock, and payment of common dividends. Cash provided by financing activities was $67.1$64.7 million for the threesix months ended MarchJune 31,30, 2025, primarily attributable to proceeds from issuance of debt at the holding company, partially offset by the payment of dividends, cash paid in connection with vested or exercised stock awards, and payment of debt issuance costs.

Reworded

Cash usedprovided inby discontinued operating activities was $9.8$53.2 million, comparedand to cash used in operating activities of $21.0$1.6 million for the threesix months ended MarchJune 31,30, 2026 and 2025, respectively. TheCash provided by discontinued investing activities was $696.3 million, and $73.0 million for the six months ended June 30, 2026 and 2025, respectively, primarily related to the Fortegra and Reliance dispositions. Investing activities related to the Fortegra sale included deal proceeds of $1.12 billion, reduced by $402.7 million of cash held at Fortegra and expected escrow-related amounts, resulting in net proceeds of $713.4 million. Investing activities related to the Reliance sale included deal proceeds of $46.9 million, reduced by $14.6 million of cash held at Reliance and expected escrow-related amounts, resulting in net proceeds of $29.9 million. Cash provided by discontinued financing activities was $42.2 million for the six months ended June 30, 2026, compared with cash used in investingdiscontinued activities was $38.6 million, compared to cash used in investingfinancing activities of $6.2$10.2 million for the threesix months ended MarchJune 31, 2026 and 2025, respectively. The cash provided by financing activities was $24.0 million, for the three months ended March 31, 2026. The cash used in financing activities was $5.8 million for the three months ended March 31,30, 2025.

Reworded

The preparation of ourthe Company’s financial statements, which are in accordance with U.S. GAAP, requires management to make estimates and assumptions that affect the amounts reported in ourthe financial statements and accompanying notes. Actual results could differ materially from those estimates. There have been no material changes to the critical accounting policies and estimates as discussed in Part II, Item 7A in ourTiptree’s Annual Report on Form 10-K for the fiscal year ended December 31, 2025.

TIPT insider buying and selling (Form 4)

Since 2026-04-11, insiders reported open-market purchases in 1 Form 4 filing (1 insider, 1 trade date, 990 shares, about $17.3K) and open-market sales in 0 filings. Net open-market shares: 990 (purchases minus sales); net value about $17.3K.Totals add up every open-market (code P and S) line in those filings, using the prices reported in the filings. Awards, option exercises, tax withholding and gifts are listed below but not counted.

Trade dateInsiderTransactionSharesPriceValueOwned afterFiling
2026-10-06Smith Bradley E.
Director
Grant/award 1,807— —109,070 SEC
2026-10-06Goldwasser Lesley
Director
Grant/award 1,084— —117,699 SEC
2026-07-02Smith Bradley E.
Director
Grant/award 1,768— —107,263 SEC
2026-07-02Goldwasser Lesley
Director
Grant/award 1,061— —116,615 SEC
2026-05-27Ilany Jonathan
Director
Open-market purchase 990$17.45 $17.3K193,011 SEC

Well-known investors holding TIPT (13F)

InvestorQuarterSharesReported value% of their 13FChange vs prior quarter
AQR Capital Management (Cliff Asness) COM2026-06-30364,204$6.5M0.0%Added 164%
D. E. Shaw & Co. COM2026-06-30187,703$3.4M0.0%Added 1%
Millennium Management (Israel Englander) COM2026-06-30177,810$3.2M0.0%Reduced 45%
Renaissance Technologies COM2026-06-30172,600$3.1M0.0%New position
Two Sigma Investments COM2026-06-30110,658$2.0M0.0%Added 97%
Citadel Advisors (Ken Griffin) COM2026-06-3065,281$1.2M0.0%Reduced 49%
Point72 Asset Management (Steve Cohen) COM2026-06-3034,882$625.1K0.0%Reduced 43%

13F reports are filed up to 45 days after quarter end and show long U.S. equity positions only; options positions are omitted here.

Coming soon: email alerts when TIPT files, watchlists and downloadable comparisons.